Lauric acid or systematically, dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids, is a bright white, powdery solid with a faint odor of bay oil or soap.
The salts and esters of lauric acid are known as laurates.
Lauric acid is an inexpensive, non-toxic and safe to handle compound often used in laboratory investigations of melting-point depression.
Lauric acid is a solid at room temperature but melts easily in boiling water, so liquid lauric acid can be treated with various solutes and used to determine their molecular masses.
Lauric acid, C12H24O2, also known as dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain.
The powdery, white crystalline acid has a slight odor of oil of bay and occurs naturally in various plant and animal fats and oils.
Lauric acid is a major component of coconut oil and palm kernel oil. Lauric acid is used as an intermediate and surface active agent in industry and in the manufacture of personal care products in the consumer market.
Lauric acid is the most abundant fatty acid present in coconut oil. It is also one of the main flavor constituents of Chinese rice wine and sweet cream butter.
Lauric acid is commonly used in lubricants and also in edible-coating formulations.
A fatty acid with a 12 carbon chain. Lauric acid occurs naturally in Coconut oil and Laurel oil. At room temperature, lauric acid is a solid. The waxy compound is used to make alkyd resins, wetting agents, soaps, detergents, and insecticides.
IUPAC name: Dodecanoic acid
Other names: n-Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers)
Lauric acid or systematically, dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids, is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and esters of lauric acid are known as laurates. It is found in many vegetable fats, particularly in coconut and palm kernel oils. People use it as medicine.
Synonyms: Deodecanoic Acid, Lauric Acid, Lauric Fatty Acid
INCI: Lauric Acid
Chemical formula: C12H24O2
CAS #: 143-07-7
CAS Number: 143-07-7
C12 fatty acid
Coconut oil fatty acids
Origin(s): Vegetal, Animal
Other languages: Acide laurique, Acido laurico, Laurische Säure
INCI name: LAURIC ACID
EINECS/ELINCS number: 205-582-1
Comedogenic potential (pc): 4
Bio-compatible (COSMOS Reference)
Its functions (INCI)
Cleansing : Helps to keep a clean surface
Emulsifying : Promotes the formation of intimate mixtures between immiscible liquids by modifying the interfacial tension (water and oil)
Surfactant : Reduces the surface tension of cosmetics and contributes to the even distribution of the product when it is used
Dodecanoic acid, also known as dodecanoate or lauric acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutra
Lauric Acid (dodecanoic acid, N-Dodecanoic acid, Dodecylic acid) is a saturated medium-chain fatty acid with a 12-carbon backbone. Lauric acid is found naturally in various plant and animal fats and oils, and is a major component of coconut oil and palm kernel oil.
Lauric acid is a saturated fat. Lauric acid is found in many vegetable fats, particularly in coconut and palm kernel oils. People use it as medicine.
Lauric acid is used for treating viral infections including influenza (the flu); swine flu; avian flu; the common cold; fever blisters, cold sores, and genital herpes caused by herpes simplex virus (HSV); genital warts caused by human papillomavirus (HPV); and HIV/AIDS. It is also used for preventing the transmission of HIV from mothers to children.
Other uses for lauric acid include treatment of bronchitis, gonorrhea, yeast infections, chlamydia, intestinal infections caused by a parasite called Giardia lamblia, and ringworm.
In foods, lauric acid is used as a vegetable shortening.
In manufacturing, lauric acid is used to make soap and shampoo.
USES AND APPLICATIONS FOR LAURIC ACID
Lauric acid uses include acid chlorides, amphoteric surfactant intermediate, anti ageing creams & lotions, antiperspirants, bar soap, betaines, body wash, cosmetics, deodorants, emollient, emulsifier, exfoliant scrub, facial cleaner, foundations, glycerol esters, hair care, hair colorants, imidazolines, lip balm, liquid hand soap, lubricant, moisturizing cream formulations, organic peroxides, sarcosinates, shaving cream, shower gels, skin care products, etc
Food and Nutrition: Lauric acid is used as a vegetable shortening.
Personal Care: Its natural bay leaf-like scent can be used in high amounts to add fragrance to products, but it's more often used as a base for cleansing agents, and, increasingly, for its skin-soothing actions.
Pharmaceutical: Lauric acid is used for treating viral infections including influenza (the flu); swine flu; avian flu; the common cold; fever blisters, cold sores, and genital herpes caused by herpes simplex virus (HSV); genital warts caused by human papillomavirus (HPV); and HIV/AIDS.
Cosmetics and Pharmaceuticals use: Oil base for creams, lotions, lipsticks, powders, skin ointments, face cleaners, body shampoos, soaps etc,.
Use: Flavours and Fragrances, Cosmetics and Personal Care, Industrial, Inks and Coatings
A 12 carbon length fatty acid that can be found naturally in coconut milk, coconut oil, laurel oil, and palm kernel oil. It's also in breast milk. As a skincare ingredient, it can be used as an emulsifier or as a cleansing agent.
What's more, there is emerging research about lauric acid being a good anti-acne ingredient. A 2009 study found that the lowest concentration to prevent evil acne-causing P. acnes growth of lauric acid is over 15 times lower than that of gold standard anti-acne ingredient benzoyl peroxide.
Lauric Acid is a saturated medium-chain fatty acid with a 12-carbon backbone.
Lauric acid is found naturally in various plant and animal fats and oils, and is a major component of coconut oil and palm kernel oil.
Lauric acid is a white solid with a slight odor of bay oil.
Lauric acid, CAS 143-07-7, chemical formula C12H24O2, is produced as a white crystalline powder, has a slight odor of bay oil, and is soluble in water, alcohols, phenyls, haloalkanes, and acetates.
It is non-toxic, safe to handle, inexpensive, and has a long shelf life.
It is mainly used in the manufacture and production of soaps and other cosmetics as well as scientific laboratory uses.
Lauric acid is mainly used in the manufacturing of soaps and other cosmetics.
In scientific laboratories, lauric acid is often used to investigate the molar mass of unknown substances via freezing-point depression.
In industry, lauric acid is used as an intermediate and as a surface active agent.
The consumer market uses lauric acid in the cleaning, furnishing, and production of personal care products.
In medicine, lauric acid is known to increase total serum cholesterol more than many of the other fatty acids.
As a natural biochemical, lauric acid from coconut and palm kernel oils comprises 44 to 53 percent of their total fatty acid contents.
Newly genetically engineered laurate canola (rapeseed) oil provides about 36 percent lauric acid, while the milk fat and butter from ruminant animals, such as cows, offers about 3 percent.
Synthesized or extracted for the pharmaceutical industry, lauric acid is known for its antimicrobial properties, and as the precursor to monolaurin, a more powerful antimicrobial agent that is able to fight lipid-coated RNA and DNA viruses, several pathogenic Gram-positive bacteria, yeasts, and various pathogenic protozoa.
Most recently, lauric acid derived from coconut oil, and the related monolaurin, have been examined as part of the drug therapy for treating HIV infections by reducing the patient's viral load.
However, pure lauric acid cannot be ingested because it is severally irritating, but when lauric acid is chemically bound to glycerol (trade name lauricidin), there are no gastrointestinal problems.
At one time, coconut and palm fats and oils received negative press because of their high levels of saturated fats.
Unlike the long chain triglycerides found in seed oils and hydrogenated coconut fat, medium chain triglycerides featured in unadulterated coconut and coconut milk do not raise serum cholesterol nor contribute to heart disease.
Known as dodecanoic acid to a biochemist, lauric acid features 12 carbons, 24 hydrogens, and 2 oxygen atoms, and a molecular weight of 200.32.
As a solid, lauric acid forms colorless or white needle-like crystals with a faint odor of bay oil, melts at about 44 degrees Celsius, and boils at 225 degrees Celsius.
While it is soluble in ether and other organic solvents, lauric acid is insoluble in water.
Usually coconut oil is highly modified in cosmetics, food products, and animal feeds to prevent rancidity and extend shelf life, but as a result, the lauric acid is converted from a beneficial substance into a probable carcinogen.
Industrial applications of lauric acid and its derivatives include the fatty acid as a component of alkyd resins, wetting agents, a rubber accelerator and softener, detergents, and insecticides.
Lauric acid, as a component of triglycerides, comprises about half of the fatty-acid content in coconut milk, coconut oil, laurel oil, and palm kernel oil (not to be confused with palm oil), Otherwise, it is relatively uncommon.
It is also found in human breast milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).
Lauric acid is an inexpensive, non-toxic and safe to handle compound often used in laboratory investigations of melting-point depression.
Lauric acid is a solid at room temperature but melts easily in boiling water, so liquid lauric acid can be treated with various solutes and used to determine their molecular masses.
Lauric acid, or dodecanoic acid, is the main acid in coconut oil and in palm kernel oil, and is believed to have antimicrobial properties.
The detected values of half maximal effective concentration (EC(50)) of lauric acid on P. acnes, S. aureus, and S. epidermidis growth indicate that P. acnes is the most sensitive to lauric acid among these bacteria.
In addition, lauric acid did not induce cytotoxicity to human sebocytes.
This data highlight the potential of using lauric acid as an alternative treatment for antibiotic therapy of acne vulgaris. Lauric acid is used in the manufacture of soaps, detergents, cosmetics, and lauryl alcohol.
The primary fatty acid of coconut oil is lauric acid, which is present at approximately 45–53 %.
The metabolic and physiological properties of lauric acid account for many of the properties of coconut oil.
Coconut oil is rapidly metabolized because it is easily absorbed and lauric acid is easily transported.
Detailed studies have shown that the majority of ingested lauric acid is transported directly to the liver where it is directly converted to energy and other metabolites rather than being stored as fat.
Such metabolites include ketone bodies, which can be used by extrahepatic tissues, such as the brain and heart, as an immediate form of energy.
Studies on the effect of lauric acid on serum cholesterol are contradictory.
Among saturated fatty acids, lauric acid has been shown to contribute the least to fat accumulation.
Lauric acid and monolaurin have demonstrably significant antimicrobial activity against gram positive bacteria and a number of fungi and viruses.
Today there are many commercial products that use lauric acid and monolaurin as antimicrobial agents.
Because of the significant differences in the properties of lauric acid relative to longer chain fatty acids, they are typically differentiated as medium-chain fatty acids covering C6–C12, and long-chain fatty acids covering C14 and longer
In various plants
The palm tree Attalea speciosa, a species popularly known in Brazil as babassu – 50% in babassu oil
Attalea cohune, the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) – 46.5% in cohune oil
Astrocaryum murumuru (Arecaceae) a palm native to the Amazon – 47.5% in "murumuru butter"
Coconut oil 49%
Pycnanthus kombo (African nutmeg)
Virola surinamensis (wild nutmeg) 7.8–11.5%
Peach palm seed 10.4%
Betel nut 9%
Date palm seed 0.56–5.4%
Durio graveolens (a species of durian) 1.31%.
Macadamia nut 0.072–1.1%
Watermelon seed 0.33%
Viburnum opulus 0.24-0.33%
Citrullus lanatus (egusi melon)
Pumpkin flower 205 ppm, pumpkin seed 472 ppm
Black soldier fly Hermetia illucens 30-50 mg/100 mg fat.
Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through it.
Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle.
Lauric acid is used mainly for the production of soaps and cosmetics.
For these purposes, lauric acid is reacted with sodium hydroxide to give sodium laurate, which is a soap.
Most commonly, sodium laurate is obtained by saponification of various oils, such as coconut oil.
These precursors give mixtures of sodium laurate and other soaps.
In the laboratory, lauric acid may be used to investigate the molar mass of an unknown substance via the freezing-point depression.
The choice of lauric acid is convenient because the melting point of the pure compound is relatively high (43.8°C).
Its cryoscopic constant is 3.9°C·kg/mol.
By melting lauric acid with the unknown substance, allowing it to cool, and recording the temperature at which the mixture freezes, the molar mass of the unknown compound may be determined.
Potential medicinal properties
Lauric acid increases total serum cholesterol more than many other fatty acids, but mostly high-density lipoprotein (HDL) (the "good" blood cholesterol).
As a result, lauric acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid [examined], either saturated or unsaturated".
In general, a lower total/HDL serum cholesterol ratio correlates with a decrease in atherosclerotic risk.
Nonetheless, an extensive meta-analysis on foods affecting the total LDL/serum cholesterol ratio found in 2003 that the net effects of lauric acid on coronary artery disease outcomes remained uncertain.
A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease risk.
Lauric acid or systematically dodecanoic acid is saturated fatty acids with a 12 carbon atom chain thus falling into the medium chain fatty acids.
This acid is formed in many vegetables, fats particularly in coconut oil and palm kernel oil. Lauric acid a twelve (12) carbon chain acids, is one of the medium chain fatty acids gotten from some plants oil particularly coconut oil and others related oil such as palm kernel oil which has been known as one of the most active ingredient and is more predominant in the total saturated fat present. Lauric acid has been known as one of the most active ingredient and composed over 52% of the total 92% saturated fats present in the coconut oil and is claimed to play a significant role in the healing miracle that is revealed in coconut oil. Virgin coconut oil, a potent nondrug or natural yeast fighter, contains three medium chain fatty acids, i.e. lauric acid (50% to 53%), caprylic acid, and capric acid, all of which have antibacterial and antifungal effect against lipid coated bacteria and fungi such as Candida spp. Medium-chain free fatty acids have been found to have a broad spectrum of microbicidal activity though the mechanisms by which the lipids kill bacteria is not known, but electron microscope studies indicate that they disrupt cell membranes.
On the other hand, free fatty acids (FFA) of various chain lengths (C8- C18) have antibacterial activity against a range of Grampositive bacteria, but not against a number of Gram-negative bacteria. Lauric acid is a minor sebum component (1% to 2% of total sebum FFA) Bach and Babayan, but it is the most active antimicrobial FFA [1-6].
Variations in composition plant and genetic disparity among bacteria and fungi of the same or different species have been found to be responsible for the few inconsistencies in the antibacterial and antifungal properties of plant extract. The esterification of coconut oil which yielded a carbon chain has proved beyond reasonable doubt that, lauric acid 12-carbon chain fatty acid is more biological active and has the highest antiviral activities than coconut oil which is the parent substance. This resulted from the medium chain triglycerides (MCTs) present in coconut oil which anti-bacterial influence because it has the ability to disintegrate bacterial cell walls;
MCTs are also presenting the ability to treat severe bacterial infections that are antibiotic resistant.
This acid is used for the treatment of viral infections, bacterial infections, fungal infection and protozoal infections and it is traditionally used for the production of soap and cosmetics as such, it is neutralize with sodium hydroxide (NaOH) and give sodium laurate by saponification.
Some previous studies demonstrated that lauric acid (sodium laurate) has antimicrobial efficacy against both E. faecalis biofilms and multispecies biofilms. Several claims have been made on the use of lauric acid and its parent substance coconut oil on its health benefits and medicinal effect
Chemical formula: C12H24O2
Molar mass: 200.322 g·mol−1
Appearance: White powder
Odor: Slight odor of bay oil
1.007 g/cm3 (24 °C)
0.8744 g/cm3 (41.5 °C)
0.8679 g/cm3 (50 °C)
Melting point: 43.8 °C (110.8 °F; 316.9 K)
297.9 °C (568.2 °F; 571.0 K)
282.5 °C (540.5 °F; 555.6 K) at 512 mmHg
225.1 °C (437.2 °F; 498.2 K) at 100 mmHg
Solubility in water
37 mg/L (0 °C)
55 mg/L (20 °C)
63 mg/L (30 °C)
72 mg/L (45 °C)
83 mg/L (100 °C)
Solubility: Soluble in alcohols, diethyl ether, phenyls, haloalkanes, acetates
Solubility in methanol
12.7 g/100 g (0 °C)
120 g/100 g (20 °C)
2250 g/100 g (40 °C)
Solubility in acetone
8.95 g/100 g (0 °C)
60.5 g/100 g (20 °C)
1590 g/100 g (40 °C)
Solubility in ethyl acetate
9.4 g/100 g (0 °C)
52 g/100 g (20°C)
1250 g/100 g (40°C)
Solubility in toluene
15.3 g/100 g (0 °C)
97 g/100 g (20°C)
1410 g/100 g (40°C)
log P 4.6
2.13·10−6 kPa (25 °C)
0.42 kPa (150 °C)
6.67 kPa (210 °C)
Acidity (pKa) 5.3 (20 °C)
0.442 W/m·K (solid)
0.1921 W/m·K (72.5 °C)
0.1748 W/m·K (106 °C)
Refractive index (nD)
1.423 (70 °C)
1.4183 (82 °C)
6.88 cP (50 °C)
5.37 cP (60 °C)
Triclinic, aP228 (γ-form)
P21/a, No. 14 (α-form)
P1, No. 2 (γ-form)
Point group 2/m (α-form)
a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form)
α = 90°, β = 129.22°, γ = 90°
Heat capacity (C)
Std enthalpy of
Std enthalpy of
7425.8 kJ/mol (292 K)
Aliphat No. 4
C12 fatty acid
Ninol AA62 Extra
Hydrofol acid 1255
Hydrofol acid 1295
Lauric acid, pure
Lauric acid (natural)
Coconut oil fatty acids
Dodecanoic Acid Anion
Lunac L 70
DODECANOIC ACID (LAURIC ACID)
Lauric acid, 99%
FEMA No. 2614
Dodecanoic acid(Lauric acid)
Lauric acid (NF)
Lauric Acid 652
Lauric Acid, Reagent
Nissan NAA 122
Lunac L 98
Univol U 314
Dodecanoic acid, 98%
Dodecanoic acid, 99%
Dodecanoic (Lauric) acid
dodecanoic acid ester group
4-02-00-01082 (Beilstein Handbook Reference)
Dodecanoic acid (lauric acid)
Dodecanoic acid, >=99.5%
Edenor C 1298-100
Dodecanoic acid, analytical standard
Lauric acid, >=98%, FCC, FG
Dodecanoic acid, >=99% (GC/titration)
Dodecanoic acid, purum, >=96.0% (GC)
Lauric acid, natural, >=98%, FCC, FG
oconut oil is all the rage in natural beauty and health regimens. Countless blogs and natural health websites tout it as a miracle product, able to do everything from soothe cracked skin to reverse cavities.
However, when you break coconut oil down into its active parts, things start to look less miraculous and more like science.
Lauric acid is one of those active parts. It’s a medium-length long-chain fatty acid, or lipid, that makes up about half of the fatty acids within coconut oil.
Where to find lauric acid
Lauric acid is a powerful substance that’s sometimes extracted from the coconut for use in developing monolaurin. Monolaurin is an antimicrobial agent that’s able to fight pathogens such as bacteria, viruses, and yeasts.
Because it’s irritating and not found alone in nature, you can’t ingest lauric acid on its own. You’re most likely to get it in the form of coconut oil or from fresh coconuts.
FAST FACTS ABOUT COCONUT OIL
Coconut oil is white and solid below 75℉ (23.9°C). It’s liquid above that.
It’s over 80 percent saturated fat.
It contains caprylic acid, which can help treat yeast infections.
What the research says
Though coconut oil is being studied at a breakneck pace, much of the research doesn’t pinpoint what in the oil is responsible for its reported benefits. Because coconut oil contains much more than just lauric acid, it would be a stretch to credit lauric acid with all of coconut oil’s benefits.
Still, a 2015 analysis proposed that many of the benefits tied to coconut oil are directly linked to lauric acid. They suggest that lauric acid could aid in weight loss and protect against Alzheimer’s disease, among other benefits. Its effects on blood cholesterol levels still need to be clarified.
This research suggests that the benefits of lauric acid are a result of how the body uses the acid.
The majority of lauric acid is sent directly to the liver, where it’s converted to energy rather than stored as fat. When compared with other saturated fats, lauric acid contributes the least to fat storage.
Lauric acid for acne
Because lauric acid has antibacterial properties, it’s been found to effectively combat acne. The bacteria Propionibacterium acnes are found naturally on the skin. When they overgrow, they lead to the development of acne.
The results of a 2009 study found that lauric acid could reduce inflammation and the number of bacteria present. Lauric acid worked even better than benzoyl peroxide, a common acne treatment. A 2016 study also reconfirmed the acne-fighting properties of lauric acid.
This doesn’t mean you should put coconut oil on your acne. The researchers used pure lauric acid and suggested that it could be developed into an antibiotic therapy for acne in the future.
How to use it
To reap the topical benefits of lauric acid and coconut oil, apply it directly to your skin. While this isn’t recommended for people with acne, the risks are minimal when it comes to addressing issues such as skin hydration and psoriasis.
Coconut oil can be used in cooking as well. Its sweet, nutty flavor makes it the perfect addition to desserts, including double chocolate paleo brownies and paleo banana bread.
You can also use it to sauté vegetables or to add flavor to mashed sweet potatoes or a Caribbean curry soup.
Long-chain fatty acid(s)
Medium-chain fatty acid(s)
1-Monolaurin, 1-monolauryl glyceride
2-Monolaurin, 2-monolauryl glyceride
Lauric oils have in common that their main fatty acid is lauric acid, 12:0, or dodecanoic acid.
In addition, they contain larger amounts of 8:0 (caprylic acid or octanoic acid), 10:0 (capric or decanoic acid), and especially 14:0 (myristic or tetradecanoic acid) than the common seed oils like soybean oil, rapeseed oil, and sunflower seed oil.
Historically, the main lauric oil is coconut oil, an oil produced from copra, the meat inside a coconut.
Annual production has been around 3 million tons for some decades but has now increased to 3.5 million tons.
However, with the growing production of palm oil, which is now the predominant vegetable oil at more than 60 million tons per annum, more and more palm kernels have become available.
Palm kernels contain a lauric oil, and the annual production of palm kernel oil is now close to 6 million tons and thus exceeds the annual coconut oil production.
In addition to these two major lauric oils, there are also several South American palm kernel oils in which lauric acid is the main fatty acid.
Table 1 summarizes their fatty acid compositions and compares these with those of coconut oil and palm kernel oil and Laurical, a genetically modified rapeseed plant.
Oil 6:0 8:0 10:0 12:0 14:0 16:0 18:0 18:1 18:2
Coconut oil 0.4 7.3 6.6 47.8 18.1 8.9 2.7 6.4 1.6
Palm kernel oil 0.2 3.3 3.5 47.8 16.3 8.5 2.4 15.4 2.5
Babassu oil 6 4 45 17 9 3 13 3
Cohune oil 8 7 46 16 9 3 10 1
Murumuru oil 1 1 42 37 5 2 11 1
Ouricury oil 2 10 8 46 9 8 2 13 2
Tucum oil 1 4 49 22 6 2 13 3
Laurical 38.8 4.1 2.7 1.6 32.8 11.2
Table 1 gives the overall fatty acid composition, irrespective of the position of the fatty acid on the glycerol backbone.
When lauric oils are analyzed stereospecifically, it becomes clear that the fatty acid composition of the 2-position differs from that of the outer sn-1,3-positions.
This is illustrated for coconut oil and palm kernel oil in Table 2.
Table 2. Stereospecific fatty acid analysis of coconut oil and palm kernel oil
Fatty acid Coconut oil Palm kernel oil
TAG 2-Position 1,3-Positions TAG 2-Position 1,3-Positions
6:0 0.6 – 0.9 0.4 – 0.6
8:0 9.4 0.3 13.9 5.7 2.7 7.2
10:0 7.0 3.0 9.0 4.7 2.5 5.8
12:0 50.0 80.4 34.8 52.8 62.7 47.9
14:0 17.4 8.6 21.8 16.2 15.8 16.4
16:0 7.5 1.6 10.4 7.6 2.9 9.9
18:0 2.0 0.6 2.7 2.2 0.3 3.1
18:1 4.7 3.5 5.3 9.2 11.8 7.9
18;2 1.3 1.5 1.2 1.2 1.3 1.2
Source: Table 3.162 in Gunstone, F. D., Harwood, J. L. and Padley, F. B. (eds.) The lipid handbook (2nd ed.). London: Chapman & Hall.
The fatty acid values in Table 2 are slightly different from those in Table 1 because they originate from different sources.
The fatty acid composition of the 1,3-positions has been calculated from the values in the two previous columns.
They show that palmitic acid (16:0) and stearic acid (18:0) have a strong preference for the outer, 1,3-positions.
This feature is common to most other vegetable oils. It is also valid for myristic acid (14:0), but lauric acid (12:0) on the other hand has a strong preference for the middle position of the glycerol backbone.
The preference for the 2-position of linoleic acid (18:2) that is common with seed oils is not present in the lauric oils.
Given the fatty acid compositions of the 1,3-positions and the 2-position, it is possible to calculate a triglyceride composition according to the 1,3-random, 2-random theory.
According to this theory, the molar concentration of a certain triglyceride in an oil equals the product of the mole fractions of the three fatty acids concerned.
So, if the molar fraction of palmitic acid (P) at the 1,3-positions were to be 40% and the molar fraction of linoleic acid at the 2-position were to be 50%, the triglyceride PLP would have a concentration of 0.4 × 0.5 × 0.4 × 100 = 8%.
This holds for symmetric triglycerides.
If the fatty acid at the 1-position were to differ from the fatty acid at the 3-position, there would be two positional isomers that can be listed separately or together and shown as a group.
In the latter case, the calculated percentage has to be multiplied by a factor of 2.
Because lauric oils are so rich in lauric acid and myristic acid, their saponification values are much higher than those of the common seed oils: 245–265 vs. 185–195 mg KOH per g oil.
The free fatty acid content of these seed oils is usually expressed as wt% oleic acid, but in the case of lauric oils, it is more common to express it as wt% lauric acid by assuming a molar mass of 200 instead of 282 for oleic acid.
The low unsaturated fatty acid content of the lauric oils is reflected by their low iodine values.
It also retards the formation of rancid off-flavors.
However, the presence of medium-chain fatty acids makes the oil more susceptible to hydrolysis, resulting in the formation of free fatty acids and a soapy taste.
The bottom row of Table 1 gives the fatty acid composition of Laurical, the oil of a genetically modified rapeseed developed by Calgene in 1996.
The aim of this development was to provide a cheap and reliable source of lauric acid, away from the Philippines, where typhoons frequently damage crops.
However, the growth of palm oil production increased the availability of the lauric palm kernel oil so that there was less need for alternative sources.
Consequently, the entire stock of this oil was sold for use as fuel in 2001.
Lauric acid and myristic acid are saturated fatty acids. Their formal names are dodecanoic acid and tetradecanoic acid, respectively.
Both are white solids that are very slightly soluble in water.
Lauric acid esters (principally triglycerides) are found only in vegetable fats, primarily from coconut milk and oil, laurel oil, and palm kernel oil.
In contrast, myristic acid triglycerides occur in plants and animals, notably in nutmeg butter, coconut oil, and mammalian milk.
The active substance of the biocidal product is lauric acid.
Synonyms of this fatty acid are dodecanoic acid, laurostearic acid and dodecoic acid.
The substance is CAS and EC listed (CAS-No. 143-07-7, EC-No 205-582-1).
No isomerism of lauric acid is known.
The concentration of lauric acid is in the range of 98 – 100 %.
Lauric acid is a solid waxy white substance with a weak characteristic acid odour.
The melting point is 44 °C and it’s thermally stable at room temperature.
The vapour pressure is determined to 0.0012 Pa at 25 °C.
Lauric acid shows a very low solubility in water at 20 °C with a typical solubility profile.
Only weak temperature dependence was determined.
Because of the formation of micelles at pH > 7, the solubility is determined at pH-values 3, 5 and in an un-buffered system.
In double distilled water as the test system an increase of the water solubility is observed due to extended preincubation time (48 h: 12.0 mg/l, 96 h: 21.1 mg/l, T = 20°C).
The variations could not be minimised using extended preincubation times and are comparable for the different used temperatures.
The partition coefficient n-octanol/water is dependent on the pH-value.
For the unionised form of the substance at pH = 3 and 5 the log Pow is determined to 5.2 (4.98).
The surface tension of 53.48 mN/m of a 90 % saturated test solution confirms the surface activity of the substance..
Lauric acid (CAS No. 143-07-7) is to be used as a repellent (PT 19).
Its intended use is in lotions (10% w/w of lauric acid (purity 98 – 100%) in the biocidal product) to be applied on human skin with the aim of repelling hard ticks (Ixodes ricinus).
Acceptable laboratory studies have been submitted indicating a sufficient efficacy of lauric acid in repelling the target organisms for the inclusion into Annex I of the directive 98/8/EC to be recommended.
The assessment of the data provided in support of the effectiveness of the accompanying product establishes that the product may be expected to display efficacy.
However, all claims made for the product will need to be supported at product authorisation stage
Lauric acid is a saturated fatty acid naturally occurring in plants, animals, and humans.
Natural sources of lauric acid in human food are e.g. coconut oil (48 % lauric acid), palm kernel oil (45 %), yeast extract (12 %) and butter (2.6 % lauric acid).
It is also present in human mothers’ milk.
For saturated fatty acids including lauric acid, the intake cited in the DAR under 91/414/EEC (2007, RMS IE, Table B.6-1) was 32.5 g/d for males and 23.3 g/d for females.
The mean daily per capita intake of lauric acid as food additive has been estimated to be 0.6 and 1.2 mg/d in Europe and the USA, respectively, based on production statistics (WHO 1998). In another publication (Stofberg and Grundschober 1987), the intake of lauric acid from natural food sources in the USA is assumed to exceed that from the use as food additive by a factor of approx. 1250.
By combining this information, one would arrive at an estimated daily consumption of about 1-1.5 g/person/d. For German population (age 14 – 80 yr), results of national dietary consumption study (‘Nationale Verzehrsstudie II’) were used to estimate the mean daily intake of lauric acid.
This representative study (N = 15371 persons) used dietary history method during a four week interval to survey mean dietary intake.
Based on the answers of consumed meals, using standard recipes for preparation of such meals and composition of ingredients (taken from literature or food analyses), it was possible to calculate the mean daily intake of lauric acid: mean: 36.3 mg/kg bw/d (2.7 g/d; for combined sexes) (m: 38.9 mg/kg bw/d (3.1 g/d), f: 33.7 mg/kg bw/d (2.2 g/d)) and 95th percentile: 82.1 mg/kg bw/d (5.9 g/d; for combined sexes) (m: 89.5 mg/kg bw/d (6.7 g/d), f: 72.5 mg/kg bw/d (4.5 g/d)).
(Remark: due to the employed method, the 95th percentile is no acute intake but represents the mean intake of high consumers; body weights derived from the data set of the NVS II.)
In contrast, in the context of the current dossier, the normal volume of biocidal product (containing 0.1 g lauric acid/mL) to be applied to a forearm is given by the applicant as 200 µl (cf. exposure assessment section, Doc IIB-3), which would be equivalent to 0.02 g lauric acid.
Therefore, even if the b.p. would be applied to a larger part of the body surface, the resulting maximum additional exposure to lauric acid could still be assumed to be significantly lower than baseline exposure of the general population.
The generally low systemic toxicity profile of lauric acid has been established by a variety of international bodies/regulatory programs:
Lauric acid has been evaluated by the 49th meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA) in 1997 together with other saturated aliphatic acyclic linear primary acids.
The committee concluded that “...the substances in this group would not present safety concerns at the current levels of intake” (JECFA 1997, IPCS 1998). JECFA reviewed the available data for acute toxicity, short-term and chronic toxicity, genotoxicity and reproductive toxicity.
Irritation and sensitisation were not covered be the report.
The U.S. Food and Drug Administration (FDA) issued a statement that – subject to certain conditions not relevant in the context of this dossier – “...the food additive fatty 13 acids may be safely used in food and in the manufacture of food components...” (FDA 2005).
The FDA assessment itself is not available to the German competent authorities.
In 1987, an expert panel of the Cosmetic Ingredients Review (CIR), a US program funded by the Cosmetic, Toiletry, and Fragrance Association (CTFA), concluded that lauric acid and the other evaluated fatty acids were “...safe in present practices of use and concentration in cosmetics”.
According to this publication, such practice would cover uses of up to 25 % lauric acid in cosmetic products (Anonymous 1987).
Lauric acid is widely used and regarded as safe in household cleaning products as an emulsifier, soap or detergent according to an evaluation initiated by industry organisations CEFIC and A.I.S.E (HERA 2002).
The CEFIC evaluation on C10-C22 fatty acids and its salts addressed acute toxicity, irritation/corrosion, sensitisation, repeated-dose toxicity, genotoxicity, carcinogenicity, reproduction and developmental toxicity
Lauric acid is intended for use in lotions to be applied externally on human skin to repel hard ticks.
Acceptable laboratory studies have been submitted indicating a sufficient efficacy of lauric acid in repelling the target organisms (Ixodes ricinus) for Annex I-inclusion to be recommended.
The assessment of the data provided in support of the effectiveness of the accompanying product establishes that the product may be expected to display efficacy.
However, all claims made for the product will need to be supported at product authorisation stage.
Lauric acid is a solid waxy white substance with a weak characteristic acid odour and an endogenous fatty acid of generally low toxicity.
It is, however, considered to be a skin and eye irritant.
Due to the low toxicity of lauric acid, and as exposure is estimated to be clearly below baseline exposure of the general population via food, derivation of any toxicological reference dose was considered unnecessary.
No residues in food are likely to arise from the foreseen use of the biocidal product.
Therefore, neither an ADI nor an ARfD have been set.
The active substance has no hazardous physico-chemical properties.
The physico-chemical data of the substance are acceptable.
No risk for the air compartment could be identified.
Moreover, there is no risk for the aquatic compartment including sediment and for the terrestrial compartment including groundwater considering the KOC range between 10 and 4900 related to the use of lauric acid.
Additionally, the risk for secondary poisoning is assumed to be low via ingestion of contaminated food by birds or mammals.
Lauric acid is readily biodegradable, shows no considerably potential for bioaccumulation based on physicochemical properties under pH-neutral conditions and meets none of the PBT criteria.
Furthermore, all criteria for Annex I, inclusion are fulfilled and the PEC/PNEC ratios for all environmental compartments are < 0.1.
Lauric acid is not considered as having endocrine-disrupting properties in the sense of Article 5(3), second and third subparagraphs.
Lauric acid is an endogenous fatty acid of generally low systemic toxicity.
Due to the low systemic toxicity of lauric acid, and as exposure is estimated to be clearly below baseline exposure of the general population via food, derivation of any toxicological reference dose was considered unnecessary.
No residues in food are likely to arise from the foreseen use of the biocidal product, therefore neither an ADI nor an ARfD have been set.
Lauric acid is a medium-chain saturated fatty acid. It has been found at high levels in coconut oil.
Lauric acid induces the activation of NF-κB and the expression of COX-2, inducible nitric oxide synthase (iNOS), and IL-1α in RAW 264.7 cells when used at a concentration of 25 µM.
Health, growth, immunity and development of infants depend on their breast milk consumption.
Lauric acid is one important constituent among the various nutritional factors that complex together to form the breast milk.
This medium chain triglyceride with 12-carbon atom chain component has many medicinal values.
Lauric acid has been found to have present in 6.2% of human breast milk, 3.1% of goat milk and 2.9% in cow milk.
Besides being present in milk its presence has been recognized in plant sources (mainly oil)-coconut, cohune and palm kernel oil in common.
Coconut oil extracted from a single one contains approximately 50% of Lauric acid.
The isolation of Lauric acid from plant sources hence is easier and convenient than animal sources with increase in the percentage of component extracted.
Researchers conducted study on Lauric acid suggested, it to be a non-toxic, safe to handle component with long shelf-life. It is even easily absorbable and digestible by the body.
This component has many therapeutic properties in human’s health as such – prevention from various skin diseases, decrease in the bad cholesterol level, body weight deduction.
Even antioxidant, antibacterial, antifungal, antiviral and anticancer capabilities are present in this Lauric acid.
But, till date the evidence is currently ambiguous as to whether Lauric acid supplementation has a significant effect on body.
Lauric acid (LA) (Fig. 1) - a medium-chain triglyceride (MCT) is widely acknowledged as a “healthier” saturated fat.
MCT molecules can be rapidly absorbedby body because of their ability to hydrolyze completely into fatty acids and glycerol by pancreatic lipase.
Hence being an MCT itself lauric acid’s specific chemicalstructure also allows body to absorb them as whole which makes them more easily digestible .
Even when pancreatic juice secretion is reduced due to diseases,medium chain fatty acids have the ability to get easily digested and absorbed .
Lauric acid is also used as source of direct energy because body processes them as carbohydrates .
Found in abundance from natural resources it is inexpensive, has a long shelf-lifeis non-toxic and safe to handle.
Like other fatty acids, Lauric acid is also said toincrease total serum cholesterol but it is mainly attributed to increase the "good" blood cholesterol i.e.high-density lipoprotein (HDL) which helps to decrease atherosclerotic risk in the body3, 4.
This is because medium chain fatty acids are notreadily re-synthesized to triacylglycerol like long chain fatty acids.
Instead these MCT are mostly bound with albumin as free fatty acids, transferred into portal blood, and transported to the liver, where they are transported to mitochondria and rapidly degraded through oxidation2 .
Although the net effects of Lauric acid, to decrease therisk of coronary artery disease till date remains uncertain3 .
The saturated fatty acid, Lauric acid consist of 12-carbon atom chain, also known as n- Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1- ISSN 2320-5407 International Journal of Advanced Research (2016), Volume 4, Issue 7, 1123-1128 1124 Undecanecarboxylic acid and Duodecylic acid.
It is a white, powdery solid with a faint odor of bay oil that is insoluble in water5 .
If a type of carboxylic acid donates hydrogen ions and a base is present to accept them it forms neutralization between acid and base that produces water plus a salt as byproducts.
This neutralization process is mainly used for the production of soaps and cosmetics.
LA when neutralized with sodium hydroxide produces sodium laurate, which is soap6 .
It is also used for molar mass identification ofunknown substances via the freezing-point depression method where LA mixes with unknown substance by melting and cooling process.
And then the molar mass of the unknown substances may be determined by recording the temperature at which the mixture freezes.
Lauric acid is thought to be convenient because its melting point when pure is relatively high (43.8 °C) 7 .
Among the plant sources, many vegetables fats contain LA, particularly in coconut and palm kernel oils.
The amount of Lauric acid found in foods is safe for health but there isn’t enough information whether it can be used as medicine.
Among animal resources Lauric acid is found in human breast milk, cow’s milk and goat’s milk5 too.
But the mechanism of extraction from plant resources is much efficient than that from animal resources.
The mechanism by which Lauric acid is consumed by the body is - more amount of it gets converted into monolaurin (glyceryl laurate).
Finally, this monolaurin gets converted into HDA (2-Hexadecynoic acid) version of cholesterol and prevent body from bacterial infection.
Monolaurin is commonly used in deodorants .
This review of Lauric acid, studied by us is the very first of its kind besides it has depicting the numerous essential medicinal values.
This paper also aims to bring researchers time and attention on chemical and biological properties along with identification of natural sources to isolate and applications of lauric acid for future drug development process.
Chemical Properties of lauric acid:- Being a component of triglyceride, lauric acid is the type of MCT component foundin human breast milk and helps boosting metabolism of the body.
At normal roomtemperature, a MCT component looks colorless, transparent and low viscous “waterlike” liquid oil and odorless components .
With unique chemical and biochemicalproperties this fatty acid is used for neutralization and molar mass identification ofunknown substances via the freezing-point depression method.
This dodecylic acidcontaining numerous medicinal values may cure many diseases with its unique ability of being easily absorbed and digested by the body .
Table 1 represents the chemical properties of Lauric acid in tabular form.
Lauric acid is an insoluble carboxylic acid that can donate hydrogen ions if a base ispresent to accept them.
The reaction of Lauric acid with bases form neutralization, areaccompanied by the evolution of substantial amounts of heat.
This neutralization process is mainly used for the production of soaps and cosmetics.
Lauric acid when neutralized with sodium hydroxide produces sodium laurate, which is soap 7 .
In an aqueous solution, carboxylic acids may react with active metals to form gaseoushydrogen and a metal salt.
This phenomenon alsogenerate flammable or toxic gases along with heat by reacting with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2).
They can even generate a harmless gas (carbon dioxide) but still heat when they react with carbonates and bicarbonates. Other chemical properties of carboxylic acids are they may initiate polymerization reactions and they often catalyze (increase the rate of) chemical reactions like other acids14 .
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Table 1:- Chemical properties of lauric acid Sl. No. Details of Chemical properties of Lauric Acid.
Chemical name Lauric Acid 2. IUPAC name Dodecanoic acid 3.
Other names n-Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid .
Molecular formula C12H24O2 5.
Molar mass 200.32 g mol−1 6. Appearance White powder 7.
Odor Slight odor of bay oil 8. Density 1.007 g/cm3 (24 °C) 11,0.8744 g/cm3 (41.5 °C) 12,0.8679 g/cm3 (50 °C)13 9.
Thermal conductivity 0.442 W/m·K (solid) 10, 0.1921 W/m·K (72.5 °C), 0.1748 W/m·K (106 °C) 11 10.
Refractive index(nD) 1.423 (70 °C) 9 , 1.4183 (82 °C) 13 11.
Viscosity 6.88 cP (50 °C), 5.37 cP (60 °C) 12 12.
Melting point 43.8 °C (110.8 °F; 316.9 K)13 13.
Boiling point 297.9 °C (568.2 °F; 571.0 K),282.5 °C (540.5 °F; 555.6 K) at 512 mmHg9 , 225.1 °C (437.2 °F; 498.2 K)at 100 mmHg13, 14 14.
Solubility in water Insoluble 15.
Solubility Soluble in alcohols,(C2H5)2O, phenyls, haloalkanes, acetates15 16.
Solubility in methanol 12.7 g/100 g (0 °C),120 g/100 g (20 °C),2250 g/100 g (40 °C) 15 17.
Solubility in acetone 8.95 g/100 g (0 °C),60.5 g/100 g (20 °C),1590 g/100 g (40 °C) 15 18.
Solubility in ethyl acetate 9.4 g/100 g (0 °C),52 g/100 g (20 °C),1250 g/100 g (40 °C) 15 19.
Solubility in toluene 15.3 g/100 g (0 °C),97 g/100 g (20 °C),1410 g/100 g (40 °C) 15 20. log P 4.616 21.
Vapor pressure 0.42 kPa (150 °C)13,2.13·10-6 kPa (25 °C) 15, 6.67 kPa (210 °C) 17 22
Acidity (pKa) 5.3 (20 °C) 16 23 Stability Stable.
Combustible. Incompatible with bases, oxidizing agents, reducing agents.
Biological properties of Lauric Acid:-
Lauric Acid may be used in the daily diet for appreciable amount to prevent many diseases.
But the only way one could receive Lauric Acid is from natural sources.
Table 2 illustrates the list of natural sources with approximate percentage of lauric acid in them.
Because of its easily absorbable and digestible properties by body a new breakthrough in research may be found that a natural lauric acid is very safe to consume.
Lauric Acid is mostly found in plant material such as vegetables, coconut oil, cohune oil, palm kernel oil etc.
They can be easy natural sources for isolating the acid in huge amount to study its biological activity for the development of new drug in future.
Now a day’s medium chained fatty acid have attracted more attention as being part of a healthy diet, because they are absorbed directly into the portal vein, transported rapidly to the liver for β-oxidation, and thus increase diet-induced thermo genesis.
By β-oxidation process Lauric acid is directly metabolized with successive removal of two carbon (acetyl) fragments from the carboxyl terminal end of the molecule.
This acid may also be metabolized by a route involving hydroxylation of its twelfth (ω) carbon atom by certain cytochrome P45023 4A isoforms, followed by the oxidation of ω hydroxyl group to a carboxylic acid by cytosolic alcohol and aldehyde dehydrogenases.
In the 1950s for the first time MCT was recommended as clinical dietary supplements of malnutrition syndromes, because of its rapid absorption and solubility.
In the 1970s, started it’s utilization as edible oil and currently used as additive for foods, base material of pigments, and mold and lubricating oil in food production .
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Table 2:- List of natural source of lauric acid Identified Natural Sources Quantity of lauric acid found in respective natural source in percentage In Animal source Human Breast Milk 6.2% of total fat Cow’s milk 2.9% of total fat Goat’s milk 3.1% of total fat In Plant source Palm kernel oil 50% Cohune oil 46.5% Coconut oil 49% Murumuru butter 47.5% wild nutmeg 7.8–11.5% Peach palm seed 10.4% Betel nut 9% Date palm seed 0.56–5.4% Macadamia nut 0.072–1.1% Plum 0.35–0.38% Water melon seed 0.33% Lauric acid (a major component of coconut oil and an important MCT fatty acid) possesses many types of therapeutic properties:-
Antibacterial activity:- Laurostearic acid’s use may prevent skin diseases becauseit has the ability to fight against various types of bacterial infections.
As par example, from many decades’people have been using coconut oil as a cure for fungal and bacterial infections on skin.
Lauric Acid is one of the main ingredients of coconut oil (approx ~ 50%) but study on use of pure lauric acid directly to cure skin diseases is less evidenced.
Recently Teruaki Nakatsujiet al.(2009) reported that lauric acid shows the inhibitory effect on the growth of skin bacteria such as Propionibacterium acnes isolated from the most common disorder of human skin i.e. acne vulgaris that affects up to 80% of individuals in their lives20 .
Atopic Dermatitis (AD) is again a chronic skin disease where the skin turns dry and is readily infected and colonized by Staphylococcus species with an increased penetration of allergens.
This is characterized by defects in the epidermal barrier function and cutaneous inflammation.
In this phenomenon there is an increased transepidermal water loss where the ability of the stratum corneum to hold water is impaired thus causing decreased skin capacitance and hydration.
However, researches have reported that Virgin Coconut Oil [(VCO) containing ~50 % of lauric acid] shows effect on AD compared to mineral oil and virgin olive oils.
Thus, the excellent antimicrobial properties of Lauric acid may increase the demand of it in the pharmaceutical industries.
Moreover monolaurin, the monoglyceride derivative of Lauric acid have even more potent antimicrobial properties against lipid-coated RNA and DNA viruses, numerous pathogenic gram-positive bacteria, and various pathogenic protozoa reported by Paul May (2012)8 .
In addition, James and Rahman (2005) 24 reported that coconut oil can be used as a skin moisturizer, as engine lubricant and even transformer oil.
Even the acids derived from coconut oil may be used as an herbicide was also reported .
Antifungal activity:- In a recent study, Ogbolu DO et al.(2007) reported that coconut oil had also shownantifungal activity against Candida species at 100% concentration isolated from clinical specimen compared to fluconazole.
Coconut oil hence should also be used in the treatment of fungal infections in view of emerging drug-resistant Candida species.
Shari Lieberman et al. in 2006 reported that monolurin- a derivative of lauric acid may have the ability to kill or inactivate a number of fungi (several species of ringworm), yeasts, and protozoa26.
Even several studies have also reported that Candidaalbicansand the protozoan parasite Giardia lambliamay be killed by monolaurin .
Antiviral activity:- Enig M. (1998) 30 reported that Lauric acid derivatives- monolaurin may deactivatesome of the viruses that include Human Immune-deficiency Virus (HIV), measles,Herpes simplex-1, cytomegalovirus, visna virus, and vesicular stomatitis.
A studyconducted by Tayag E et al (2000) 31 where the objective was to document the viral loadof HIV viruses in patients using monolaurin at two doses (2.4 g versus 7.2 g) with 50mL of coconut oil as doses.
There were ISSN 2320-5407 International Journal of Advanced Research (2016), Volume 4, Issue 7, 1123-1128 1127 groups with 15 patients in each group.
The study was conducted for 6 months with documentation of virus present at the beginning of the study, after 3 and 6 months respectively.
At the end of the study the presence of virus was found significantly low in three patients, two from coconut-oil group and one from lower dose (2.4g) of monolaurin group.
Monolaurin can also be held responsible for inactivation of opportunistic infections and other illnesses such as chronic fatigue syndrome and immune dysfunction syndrome in HIV-positive individuals26 .
Anticancer activity:- Lauric acid is known to show anticancer activity by reducing glutathione level in cells whichis exactly what the cancer cells needs to protect themselves from- the increased oxidative stress which induces apoptosis.
Recently Fauser JK et al.(2013) 32 reportedthat Lauric acid induced apoptosis in Caco-2 (p < 0.05) and IEC-6 cells (p < 0.05) bymodifying glutathione (GSH) levels.
This occurred when lauric acid modified the phases ofcell cycle in Caco-2 and IEC-6 intestinal cell lines and generated reactive oxygenspecies (ROS) compared to butyrate, a short chain fatty acids.
Decreases Total Cholesterol level and Cardiovascular Disease:- Saturated fats have the ability to increase cholesterol level in our body and soconsumption of it in daily life should be avoided. In the recent world, hence all thepeople are suggested by doctors to avoid consummation of saturated fats as much aspossible in food staff for living healthy life.
However, MCT saturated fats have thepower to increase good cholesterol i.e. high-density lipoprotein (HDL) in blood.
Thus consumption of MCT products by people who are sensitive to cholesterol maydecrease the risk of coronary artery disease in them and even may actually help todecrease level of total blood cholesterol1 , in contrast to long chain triglyceridesaturated fat that enhances blood bad cholesterols i.e. low-density lipoprotein (LDL)and increase the level of triglycerides in blood serum.
Some studies also suggested that VCO shows the potential beneficiary effect in lowering lipid levels in serum andtissues and LDL oxidation by physiological oxidants33 .
Decreases Body weight:- Although many recent studied reported that use of coconut oil as dietetics upplementation does not cause dyslipidemia and seems to promote a reduction inabdominal obesity of women presenting waist circumferences (WC) >88 cm(abdominal obesity).
However lauric acid directly used as dietetic supplement decreases thebody weight.
An article form nutrition review suggested that MCTs have fewercalories per serving, roughly 8.3 calories per gram rather than the standard 9 caloriesper gram compared to long-chain triglycerides, the type of other saturated fats1 .
Many researchers also suggested that a diet rich in MCTs may potentially help todecrease body weight as a result of choosing to consume fewer calories, as well as areduction in waist circumference compared to a diet rich in long chain triglycerides .
Conclusion:- Lauric acid being one of the major components of coconut oil and a MCTcomponent which may be having the ability to decrease cholesterol level and decreasebody weight.
Even lauric acid may be effective against many microorganisms and can be takenon a daily basis, given that evidence suggests it does not create antiviral orantibacterial resistance like coconut oil because approximately 50% of total fat ofcoconut oil consist of LA.
The main point of this review is that lauric acid is very commonsource of food, inexpensive, non-toxic, safe to handle and easily found from naturalsource. To isolate in huge amount can be very cost efficient and may be used as drugas active agent against various disease in future.
But more clinical studies are needed to approve lauric acid as supplement for human health.
Compounds with biological roles [BR:br08001]
Saturated fatty acids
C02679 Lauric acid (12:0)
FA Fatty acyls
FA01 Fatty Acids and Conjugates
FA0101 Straight chain fatty acids
C02679 Dodecanoic acid
Phytochemical compounds [BR:br08003]
Fatty acids related compounds
Saturated fatty acids
C02679 Lauric acid
Cardiac risk factors and prevention
Lauric acid-rich medium-chain triglycerides can substitute for other oils in cooking applications and may have limited pathogenicity
Mark F McCarty and James J DiNicolantonio
Correspondence to Dr Mark F McCarty
Recently, medium-chain triglycerides (MCTs) containing a large fraction of lauric acid (LA) (C12)—about 30%—have been introduced commercially for use in salad oils and in cooking applications.
As compared to the long-chain fatty acids found in other cooking oils, the medium-chain fats in MCTs are far less likely to be stored in adipose tissue, do not give rise to ‘ectopic fat’ metabolites that promote insulin resistance and inflammation, and may be less likely to activate macrophages.
When ingested, medium-chain fatty acids are rapidly oxidised in hepatic mitochondria; the resulting glut of acetyl-coenzyme A drives ketone body production and also provokes a thermogenic response.
Hence, studies in animals and humans indicate that MCT ingestion is less obesogenic than comparable intakes of longer chain oils.
Although Lauric acid tends to raise serum cholesterol, it has a more substantial impact on high density lipoprotein (HDL) than low density lipoprotein (LDL) in this regard, such that the ratio of total cholesterol to HDL cholesterol decreases.
Lauric acid constitutes about 50% of the fatty acid content of coconut oil; south Asian and Oceanic societies which use coconut oil as their primary source of dietary fat tend to be at low cardiovascular risk.
Since ketone bodies can exert neuroprotective effects, the moderate ketosis induced by regular MCT ingestion may have neuroprotective potential.
As compared to traditional MCTs featuring C6–C10, laurate-rich MCTs are more feasible for use in moderate-temperature frying and tend to produce a lower but more sustained pattern of blood ketone elevation owing to the more gradual hepatic oxidation of ingested laurate.
This is an Open Access article distributed in accordance with the Creative Commons Attribution Non Commercial (CC BY-NC 4.0) license, which permits others to distribute, remix, adapt, build upon this work non-commercially, and license their derivative works on different terms, provided the original work is properly cited and the use is non-commercial.
Triglycerides synthesised from coconut oil
Standard medium-chain triglycerides (MCTs) are produced by hydrolysing coconut oil and esterifying the fatty acids shorter than lauric acid (LA) (C12) with glycerol; the resulting triglycerides are rich primarily in caprylic (C8) and capric (C10) acids.
The exclusion of LA reflects the fact that this fatty acid has high commercial value as a precursor for antibacterial pharmaceuticals (eg, monolaurin) and other worthwhile compounds. Coconut oil is one of the richest available sources of LA—constituting about half of its total fatty acid content—and so is used to produce LA; the shorter chain fats are hence by-products of this process and then are used for production of MCTs.
As contrasted with coconut oil, standard MCTs are consistently fluid at room temperature; their utility for cooking applications, however, is limited by their low smoke point, which makes them unsuitable for use in frying.
Recently, however, manufacturers have started to produce a novel type of MCT that contains a high fraction of LA—typically 30%.
A tablespoon of this MCT—containing 14 g of fat—is said to contain 12 g of medium-chain fatty acids (lauric 4.45 g, caprylic 3.35 g, capric 4.00 g) and 1 g of unsaturates (presumably largely oleic acid). Hence, the content of longer chain saturated fatty acids is extremely low and of questionable physiological significance.
Fatty acids | Omega-3 fatty acids | Omega-6 fatty acids | Omega-9 fatty acids |
Alpha-linolenic acid | Caprylic acid | Gadoleic acid |
Myristic acid | Lauric acid | Linoleic acid | Oleic acid |
Palmitic acid | Palmitoleic acid | Stearic acid
Fatty acids are lipid components that play a major role in cell energy and construction, particularly in cell membranes.
There are many types of fatty acids: saturated fatty acids, monounsaturated fatty acids and polyunsaturated fatty acids.
Saturated fatty acids are mainly of animal origin, and are found in butter, cream, lard and pork fat. Some vegetable oils, like palm oil, also contain these acids. They facilitate cholesterol deposits in the arteries and, as a consequence, cardiovascular disease.
Unsaturated fatty acids are mainly found in vegetable products as well as oily fish like salmon, sardines or tuna. They are especially healthy and help protect the cardiovascular system.
Fatty acids are divided into sub-categories:
- Monounsaturated fatty acids, or omega-9
- Polyunsaturated fatty acids, or omega-3 and -6
Omega-3 fatty acids
Omega-3 fatty acids are essential fatty acids. These are lipid components that the body is unable to produce, or produces in insufficient quantities. They must therefore be obtained from food.
Although they are highly useful in preventing cardiovascular disease and inflammation, omega-3 fatty acids often require the assistance of omega-6 fatty acids.
Three acids are listed in the omega-3 category:
- Alpha-linoleic acid
- Eicosapentanoic acid
- Docosahexaenoic acid
Omega-6 fatty acids
Omega-6 polyunsaturated fatty acids play a role, among other things, in constructing immune cells, improving the skin healing process, reducing inflammatory reactions and protecting the cardiovascular system.
In order for omega-6 fatty acids to be effective, they must be combined with a sufficient supply of omega-3.
Four acids are listed in the omega-6 category:
- Linolenic acid (the only essential omega-6 fatty acids)
- Gamma-linoleic acid
- Dihomo-gamma-linoleic acid
- Arachidonic acid
Omega-9 fatty acids
Omega-9 fatty acids are non-essential and monounsaturated fatty acids that the human body can synthesize in sufficient amounts using the saturated fats found in food.
Omega-9 fatty acids are composed of several acids including oleic acid, the most commonly known. It helps prevent cardiovascular diseases as well as some cancers, and also helps reduce cholesterol and hypertension.
In the omega-3 family, alpha-linoleic acid is tha only acid considered “essential” since it cannot be synthesized by the body.
In the cosmetic industry, alpha-linoleic acid is known for its hydrating power, which adds suppleness to the skin. It is anti-inflammatory and thus soothes redness and irritations in the skin.
Caprylic acid is known for its antifungal properties
A saturated fatty acid naturally present in dairy products, and also in breastmilk, caprylic acid is also found in coconut oil and palm kernel oil.
In cosmetics, it is used for its emollient and hydrating properties, as well as its antifungal properties.
In the omega-9 family, gadoleic acid is an unsaturated fatty acid present in several vegetable oils and animal fats. Similar to human sebum, it has a high absorption power in the skin and can therefore moisturize without a greasy effect.
Myristic acid is a saturated acid naturally found in dairy products, and in coconut oil and palm kernel oil.
It is used in cosmetics for its cleansing, smoothing and protective properties.
Lauric acid is a saturated fatty acid mainly found in coconut oil and used in cosmetics for its cleansing, emulsifying and surfactant properties (reduces surface tension and facilitates even distribution of the product during use).
Lauric acid also has antimicrobial action and helps harden balms, soaps and body butters.
Linoleic acid is found in several vegetable oils, and is one of the essential fatty acids in the omega-6 family.
The human body is unable to synthesize this acid, and it must be obtained from food.
Linoleic acid helps produce cell membranes. It is the precursor to all omega-6 fatty acids, meaning that all other fatty acids in this category can be produced from linoleic acid.
In the skin, linoleic acid is found in ceramides, which are found in lipid bonds, forming a truly protective epidermal barrier.
Omega-6 deficiency results in severe skin dryness, a dull complexion and brittle, lackluster hair among other things.
In the omega-9 family, oleic acid makes up 55% to 80% of the fatty acids found in olive oil. Found in high levels in the human body, it protects the cardiovascular system and lowers cholesterol.
In cosmetics, oleic acid is a very frequently used ingredient. Known for its nourishing properties, it helps strengthen the hydrolipidic film which helps the skin preserve its elasticity and suppleness. It also has repairing and skin healing properties.
Please note that the saturated form of this acid is called stearic acid.
Palmitic acid is a saturated fatty acid of animal origin and found in some vegetable oils such as palm oil or coconut oil.
An important part of the skin barrier and the acidic epidermal layer, it has emollient, emulsifying and cleansing properties.
It is also used to make certain perfumes.
Especially present in macadamia nut oil, palmitoleic acid is a monounsaturated fatty acid with extremely high absorption power in the skin.
Similar to human sebum, it hydrates and strengthens the epidermis without being harsh on the skin.
Naturally present in butter and vegetable oils, stearic acid is a saturated fatty acid that is very popular in the beauty industry.
It can be used to enrich emulsions to add a creamier consistency, stabilize formulas or even harden certain cosmetic balms and butters.
Its emollient properties allow it to hydrate and protect the epidermis or hair thanks to its filmogenic effect.
Food sources of lauric acid
Lauric acid, as glycerol ester, is found in high amount in some tropical oils.
Lauric acid is present in high quantity in coconut oil and palm kernel oil, approximately 45 g/100 g edible portion.
It should be noted that palm kernel oil is extracted from the seeds of oil palms, while palm oil from the pulp of the fruit of oil palms.
In the other vegetable fats and oils, tropical or not, such as extra virgin olive oil, corn oil, palm oil, soy oil, sesame oil, margarine, peanut butter, and so on, it is absent or present in low amount (e.g., margarine, 0.76 g/100 g edible portion).
Lauric acid is also virtually absent in the fat of red and white meat, eggs, and fish products. Small amounts are found in the lard, 0.23 g, and smoked eel, 0.28/g/100 g edible portion.
Lauric acid is present in low concentrations, <2.5 g/100 g edible portion, in milk and dairy products (the highest content is found in butter, 2.4 g/100 g edible portion).
In fruit, Lauric acid is abundant only in coconut, both fresh and dried, with respectively 16 g and 29 g/100 g edible portion. It is not present in the other fruit.
Lauric acid is not found in cereals and legumes.
Stearic Acid, Lauric Acid, Myristic Acid, Oleic Acid and Palmitic Acid are fatty acids that occur naturally in some foods.
In cosmetics and personal-care products, fatty acids and mixtures of fatty acids such as Stearic Acid, Oleic Acid, Lauric Acid, Palmitic Acid and Myristic Acid are used in a variety of cosmetic creams, cakes, soaps and pastes.
Why is it used in cosmetics and personal care products?
The following functions have been reported for these ingredients.
Opacifying agent - Myristic Acid, Palmitic Acid
Surfactant cleansing agent - Stearic Acid, Lauric Acid, Myristic Acid, Oleic Acid, Palmitic Acid
Surfactant emulsifying agent - Stearic Acid, Palmitic Acid
Stearic Acid, also known as Octadecanoic Acid, is obtained from animal and vegetable fats and oils. Humans have the ability to synthesize Stearic Acid.
In general, fatty acids are used in the production of hormones that regulate a variety of functions, including blood pressure, blood clotting and immune response.
Other names: n-Dodecanoic acid; Neo-fat 12; Aliphat no. 4; ABL; Dodecylic acid; Lauric acid; Laurostearic acid; Neo-fat 12-43; Ninol aa62 extra; Univol U-314; Vulvic acid; 1-Undecanecarboxylic acid; Duodecylic acid; C-1297; Hydrofol acid 1255; Hydrofol acid 1295; Wecoline 1295; Dodecoic acid; Hystrene 9512; Lunac L 70; Emery 650; Philacid 1200; Prifrac 2920; Undecane-1-carboxylic acid; Acide Laurique; Emery 651; Lauric acid (dodecanoic acid); Dodecanoic (Lauric) acid; dodecanoic acid (lauric acid)
Measuring the Antimicrobial Activity of Lauric Acid against Various Bacteria in Human Gut Microbiota Using a New Method
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Miki Matsue, Yumiko Mori, Satoshi Nagase, ...
First Published October 30, 2019 Research Article Find in PubMed
Article has an altmetric score of 23 Open AccessCreative Commons Attribution, Non Commercial 4.0 License
Lauric acid (LA) has a broad spectrum of anti-microbiological activities against enveloped viruses and various bacteria, and might be useful to protect against microbial infection and control the balance and distribution of bacteria in human gut microbiota.
It is not necessarily more difficult to measure antimicrobial activity the traditional way, but it is, however, more laborious.
In the present study, we developed a new method to measure the antimicrobial activity of Lauric acid in multiple samples with a microplate reader.
A “test complex” (TC) was produced consisting of 100 μL of agar medium with Lauric acid in the bottom layer and 300 μL of broth in the top layer in 96-well deep-well microplates.
Afterward, analysis of the broth in the top layer showed that the antimicrobial activity was the same as that of the “control complex,” (CC) which consisted of 100 μL of agar medium in the bottom layer and 300 μL of broth with Lauric acid in the top layer.
Furthermore, evaluation of the antimicrobial effect of the TC when using a microplate reader was the same as that with the use of the colony counting method.
The colony counting method has confirmed that the antimicrobial activity of Lauric acid when bacteria are inoculated into the broth was equivalent between CC and TC, and we validated this by correlating the number of bacteria with absorbance.
In addition, the broth itself in TC was transparent enough that the turbidity of broth can be used as an index of the number of bacteria, which enabled the use of a microplate reader for multiple samples.
For human gut microbes, Lauric acid was shown to have low antimicrobial activity against commensal lactic acid bacteria, but high antimicrobial activity against pathogenic Bacteroides and Clostridium, suggesting that Lauric acid might modulate intestinal health, as confirmed by the proposed method.
Keywords screening, human gut microbiome, antimicrobial activity, lauric acid (LA), antimicrobial method
In conclusion, the proposed method for measuring the antimicrobial effect of Lauric acid can be used to quickly and simultaneously evaluate a large number of types of FAs with very simple preparation steps as compared with more conventional methods.
In addition, the antimicrobial activity of Lauric acid against human gut microbes was determined with the proposed method, which showed that Lauric acid has low antimicrobial activity against lactic acid bacteria, but not Bacteroides and Clostridium.
These results suggest that Lauric acid might contribute to intestinal health, as confirmed by the proposed method.
Lauric acid is a saturated fatty acid found in coconut milk, laurel oil, palm kernel oil and - most famously - coconut oil, one of the health and beauty world's favourite ingredients of the past decade.
What is it used for?
Lauric acid makes up around half of the fatty acid content of coconut oil, and many people will use the same coconut oil they'd find in their kitchen cupboard as a make-up remover, moisturiser and cleanser. However, lauric acid can also be used in its extracted form - primarily in soaps and cosmetics due to its antibacterial and anti-inflammatory properties and its long shelf life.
Clinical trials to test the effects of extracted lauric acid as a skincare ingredient are still relatively minimal, but it is thought that it could be useful in treating acne due to its anti-fungal and anti-microbial actions. As well as preventing the bacteria that cause spots from spreading, it is thought to help reduce the inflammation caused by existing blemishes too.
Lauric acid as feed additive – An approach to reducing Campylobacter spp. in broiler meat
Katrin Zeiger,Johanna Popp ,André Becker,Julia Hankel,Christian Visscher,Guenter Klein †,Diana Meemken
Published: April 18, 2017https://doi.org/10.1371/journal.pone.0175693
The increasing prevalence of Campylobacter spp. within broiler populations is a major problem for food safety and consumer protection worldwide.
In vitro studies could already demonstrate that Campylobacter spp. are susceptible to lauric acid.
The purpose of this study was to examine in vivo the influence of lauric acid as a feed additive on slaughter parameters, muscle fatty acid profile, meat quality traits and the reduction of Campylobacter coli in inoculated meat of Ross 308 (R308) and Hubbard JA 757 (HJA) broilers in three independent trials (n = 3).
Although slaughter parameters did not show any significant differences, the fatty acid profile of both breeds revealed significantly higher lauric acid concentrations (P < 0.0001) in the Musculus pectoralis superficialis of treated broilers.
Comparing both tested breeds, R308 test broilers had significantly higher lauric acid concentrations than HJA test broilers (P < 0.0001), indicating a higher conversion rate in those animals. The meat quality traits showed no differences in the R308 breed (P > 0.05), but HJA test broilers had higher values for drip loss, electrical conductivity, CIE color values L* and b*, and lower pH values.
The inoculation trials of R308 showed that initial bacterial loads of 5.9 log10 cfu/g were reduced during six days of storage (4°C) to approximately 4.3 log10 cfu/g in the control groups compared to 3.5 log10 cfu/g in the treatment groups (P = 0.0295), which could be due to antimicrobial effects of lauric acid within the muscle.
This study therefore suggests that lauric acid as a feed additive has the potential to improve food safety by reducing the numbers of Campylobacter coli in broiler meat.
However, this effect seems to be dependent on the breed determining the feed intake capacity, the fat deposition and therefore the ability to incorporate lauric acid in the muscle.
We therefore conclude that lauric acid as a feed additive could possibly improve the food safety of broiler meat because of its ability to reduce the bacterial load with Campylobacter coli.
However, broiler breed specific characteristics have to be taken into account as there were considerable differences between the breeds tested in the present study.
Further research has to investigate these influences and clarify whether these observations are transferable to other food-borne pathogens like Salmonella spp. or Listeria spp. which are able to grow during refrigerated storage .
dodecanoic acid has parent hydride dodecane
dodecanoic acid has role algal metabolite
dodecanoic acid has role antibacterial agent
dodecanoic acid has role plant metabolite
dodecanoic acid is a medium-chain fatty acid
dodecanoic acid is a straight-chain saturated fatty acid
dodecanoic acid is conjugate acid of dodecanoate
LAURIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.
Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.
Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.
Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.
A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
This compound can react with oxidizing materials. (NTP, 1992)
ALIPHAT NO. 4
HYDROFOL ACID 1255
HYDROFOL ACID 1255 OR 1295
HYDROFOL ACID 1295
LUNAC L 70
LUNAC L 98
NINOL AA62 EXTRA
UNIVOL U 314
The numerous Lauric Acid uses include:
Plastics: In plastics manufacturing applications, Lauric Acid serves as an intermediate, which is substance formed during the middle stages of a chemical reaction between the reactants and the finished product.
Food and Beverage: One of the more common uses of Lauric Acid is as raw material for emulsifiers in various food and beverage additives, particularly in the manufacturing of vegetable shortening.
Its nontoxicity also makes Lauric Acid safe for use in food production.
Surfactants and Esters: When used as anionic and nonionic surfactants, Lauric Acid has the ability to reduce surface tension between liquids and solids.
Textiles: Lauric Acid works well as a lubricant & process agent in textile manufacturing applications, as it has the ability to help water mix with oil.
Personal Care: One of the more common Lauric Acid uses is as an emulsifier for facial creams and lotions, as it possesses a strong ability to cleanse skin and hair.
It is also easy to wash away after use. You can find it in many personal care products such as shampoos, body washes and shower gels.
Soaps and Detergents: When used as a base in the production of liquid and transparent soaps, Lauric Acid can control the level of lathering, add conditioning properties and enhance overall cleaning ability.
Medical: Lauric Acid can be found in a variety of medicines used for treating viral infections, certain forms of influenza, fever blisters, cold sores, bronchitis, yeast infections, gonorrhea, genital herpes and many others.
However, there is insufficient evidence to determine its overall effectiveness in treating these conditions.
Preliminary research also indicates that Lauric Acid may aid in the treatment of acne as well.