2-HYDROXYBENZOIC ACID (SALICYLIC ACID)

Salicylic acid = 2-Hydroxybenzoic acid

CAS Number: 69-72-7
EC Number: 200-712-3
Chemical formula: C7H6O3
Molar mass: 138.122 g·mol−1

2-Hydroxybenzoic acid (Salicylic acid) is an organic compound with the formula HOC6H4CO2H.
A colorless, bitter-tasting solid, 2-Hydroxybenzoic acid (Salicylic acid) is a precursor to and a metabolite of aspirin (acetylsalicylic acid).

2-Hydroxybenzoic acid (Salicylic acid) is a beta-hydroxy acid (BHA) that helps promote the skin’s natural exfoliation process.
2-Hydroxybenzoic acid (Salicylic acid) is originally derived from the bark of certain plants—such as white willow and wintergreen leaf—salicylic acid is most often created in a lab today.

2-Hydroxybenzoic acid (Salicylic acid) has long been used to target various concerns, including rough and bumpy skin (also known as keratosis pilaris), clogged pores, and skin conditions like psoriasis.
When used as part of your skincare regimen, 2-Hydroxybenzoic acid (Salicylic acid)’s mild yet effective exfoliating properties can help leave your skin feeling softer and smoother.

2-Hydroxybenzoic acid (Salicylic acid) is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen.
The name is from Latin salix for willow tree.

2-Hydroxybenzoic acid (Salicylic acid) is an ingredient in some anti-acne products.
Salts and esters of salicylic acid are known as salicylates.

2-Hydroxybenzoic acid (Salicylic acid) is an important organic synthetic raw material, widely used in medicine, pesticides, dyes, rubber, food and perfumes.
2-Hydroxybenzoic acid (Salicylic acid) is a beta hydroxy acid that occurs as a natural compound in plants.
2-Hydroxybenzoic acid (Salicylic acid) has direct activity as an anti-inflammatory agent and acts as a topical antibacterial agent due to its ability to promote exfoliation.

In the pharmaceutical industry, the main drug productions of salicylic acid are sodium salicylate, wintergreen oil (methyl salicylate), aspirin (acetylsalicylic acid), salicylic acid amine, phenyl salicylate.
In dye industry, 2-Hydroxybenzoic acid (Salicylic acid) is used for production mordant pure yellow , direct yellow 3GN, direct yellow GR, direct brown 3GN, acid mordant brown G, acid mordant yellow GG, acid yellow dye complex.

In pesticide production, 2-Hydroxybenzoic acid (Salicylic acid) is used for the synthesis of organic phosphorus pesticide Isocarbophos, intermediate isopropyl salicylate isofenphos methyl and Rodenticide warfarin, coumatetralyl intermediate 4-hydroxycoumarin.
In rubber industry, 2-Hydroxybenzoic acid (Salicylic acid) is used as anti scorching agent and production of ultraviolet absorbent and foaming agent.

2-Hydroxybenzoic acid (Salicylic acid) is perfume material, used for the preparation of methyl salicylate, salicylic acid ethyl ester; food preservatives, its sodium Salt is mostly used, now a number of countries have been banned; methyl salicylate can be used as oral cleaning agents, such as toothpaste flavor.
2-Hydroxybenzoic acid (Salicylic acid) is a beta hydroxy acid that occurs as a natural compound in plants.

2-Hydroxybenzoic acid (Salicylic acid) has direct activity as an anti-inflammatory agent and acts as a topical antibacterial agent due to its ability to promote exfoliation.
2-Hydroxybenzoic acid (Salicylic acid) is an odorless white to light tan solid.
Sinks and mixes slowly with water.

What is 2-Hydroxybenzoic acid (Salicylic acid)?
First off, let's establish what 2-Hydroxybenzoic acid (Salicylic acid) is.
2-Hydroxybenzoic acid (Salicylic acid) is derived from willow bark, says cosmetic chemist Ron Robinson, and it belongs to a class of ingredients called salicylates.
2-Hydroxybenzoic acid (Salicylic acid)'s structure is a little complicated, but understanding it is important to learning why (and how) it works so well.

When 2-Hydroxybenzoic acid (Salicylic acid) comes to skin-care products, there are two classes of acids you'll see often: beta hydroxy acids (BHAs) and alpha hydroxy acids (AHAs).
2-Hydroxybenzoic acid (Salicylic acid) is a beta hydroxy acid.
This means the hydroxy part of the molecule is separated from the acid part by two carbon atoms, as opposed to an alpha hydroxy acid where they're separated by one carbon atom."

What does 2-Hydroxybenzoic acid (Salicylic acid) do for the skin?
2-Hydroxybenzoic acid (Salicylic acid) can get deep into your skin to do its job.
This quality is precisely what makes it such a potent ingredient for targeting acne — especially for blackheads and whiteheads.

2-Hydroxybenzoic acid (Salicylic acid) is also an exfoliant.
This breaking down of skin cells promotes exfoliation.
2-Hydroxybenzoic acid (Salicylic acid) is considered a keratolytic medication, which means that it's perfect for supreme exfoliation.
Keratolytic medications cause softening and sloughing of the top layer of skin cells.

2-Hydroxybenzoic acid (Salicylic acid) also loosens and breaks apart desmosomes (attachments between cells in the outer layer of skin).
This 'desmolytic' action encourages exfoliation of skin and unclogging of pores.

"One thought etiology of acne is that the skin cells do not behave normally, and rather than sloughing off through a healthy skin cell cycle, they stick together and clog the pores, creating cysts and blackheads," says Dr. Nazarian.
"2-Hydroxybenzoic acid (Salicylic acid) aids in removing and loosening these skin cells and helps to dissolve the blackheads."

2-Hydroxybenzoic acid (Salicylic acid) works best on blackheads and whiteheads.
Schueller says there are three factors that contribute to acne: an abnormal sloughing off of skin cells, excessive oiliness, and the action of P. acnes bacteria. "2-Hydroxybenzoic acid (Salicylic acid) helps with the first cause by dissolving the type of skin debris that clogs pores and causes acne," he says.
Therefore, 2-Hydroxybenzoic acid (Salicylic acid) is ideal for treating blackheads and whiteheads.

"2-Hydroxybenzoic acid (Salicylic acid) can directly dissolve the keratin plugs and regulate the skin cells," says Dr. Nazarian.
"2-Hydroxybenzoic acid (Salicylic acid) does have some effectiveness against cystic acne due to its antibacterial activity, but less so than the classic blackheads and whiteheads."

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
Medicine:
2-Hydroxybenzoic acid (Salicylic acid) as a medication is commonly used to remove the outer layer of the skin.

As such, 2-Hydroxybenzoic acid (Salicylic acid) is used to treat warts, psoriasis, acne vulgaris, ringworm, dandruff, and ichthyosis.
Similar to other hydroxy acids, 2-Hydroxybenzoic acid (Salicylic acid) is an ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts.

Uses in manufacturing of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is used as a food preservative, a bactericide, and an antiseptic.
2-Hydroxybenzoic acid (Salicylic acid) is used in the production of other pharmaceuticals, including 4-aminosalicylic acid, sandulpiride, and landetimide (via salethamide).

2-Hydroxybenzoic acid (Salicylic acid) has long been a key starting material for making acetylsalicylic acid (aspirin).
Aspirin (acetylsalicylic acid or ASA) is prepared by the esterification of the phenolic hydroxyl group of 2-Hydroxybenzoic acid (Salicylic acid) with the acetyl group from acetic anhydride or acetyl chloride.

ASA is the standard to which all the other non-steroidal anti-inflammatory drugs (NSAIDs) are compared.
In veterinary medicine, this group of drugs is mainly used for treatment of inflammatory musculoskeletal disorders.

Bismuth subsalicylate, a salt of bismuth and 2-Hydroxybenzoic acid (Salicylic acid), is the active ingredient in stomach-relief aids such as Pepto-Bismol, is the main ingredient of Kaopectate, and "displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic".
Other derivatives include methyl salicylate used as a liniment to soothe joint and muscle pain and choline salicylate used topically to relieve the pain of mouth ulcers.
Aminosalicylic acid is used to induce remission in ulcerative colitis, and has been used as an antitubercular agent often administered in association with isoniazid.

Sodium salicylate is a useful phosphor in the vacuum ultraviolet spectral range, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.
It fluoresces in the blue at 420 nm. It is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.

Mechanism of action:
2-Hydroxybenzoic acid (Salicylic acid) modulates COX-1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins.
Salicylate may competitively inhibit prostaglandin formation.
Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms.

2-Hydroxybenzoic acid (Salicylic acid) works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth.
2-Hydroxybenzoic acid (Salicylic acid) inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenine dinucleotide and noncompetitively with UDPG.

2-Hydroxybenzoic acid (Salicylic acid) also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid to the phenolic acceptor.
The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.

Preferred IUPAC name:
2-Hydroxybenzoic acid

Identifiers of 2-Hydroxybenzoic acid (Salicylic acid):
CAS Number: 69-72-7
CHEBI:16914
ChEMBL: ChEMBL424
ChemSpider: 331
DrugBank: DB00936
ECHA InfoCard: 100.000.648
EC Number: 200-712-3
IUPHAR/BPS: 4306
KEGG: D00097
PubChem CID: 338
RTECS number: VO0525000
UNII: O414PZ4LPZ
CompTox Dashboard (EPA): DTXSID7026368

2-Hydroxybenzoic acid (Salicylic acid) is a beta-hydroxy acid (BHA) that helps promote the skin’s natural exfoliation process.

KEYWORDS:
69-72-7, 200-712-3, Benzoic acid 2-hydroxy-, o-Hydroxybenzoic acid, Phenol-2-carboxylic acid, Psoriacid-S-Stift, Retarder W, Salicylic acid collodion, Orthohydroxybenzoic acid, Duoplant

2-Hydroxybenzoic acid (Salicylic acid) is a beta hydroxy acid.
2-Hydroxybenzoic acid (Salicylic acid)’s well-known for reducing acne by exfoliating the skin and keeping pores clear.

You can find 2-Hydroxybenzoic acid (Salicylic acid) in various over-the-counter (OTC) products.
2-Hydroxybenzoic acid (Salicylic acid)’s also available in prescription-strength formulas.

2-Hydroxybenzoic acid (Salicylic acid) works best for mild acne (blackheads and whiteheads).
2-Hydroxybenzoic acid (Salicylic acid) can also help prevent future breakouts.
Keep reading to learn how 2-Hydroxybenzoic acid (Salicylic acid) helps to clear acne, what form and dosage to use, and what potential side effects to be aware of.

How does salicylic acid work on acne?
When your hair follicles (pores) get plugged with dead skin cells and oil, blackheads (open plugged pores), whiteheads (closed plugged pores), or pimples (pustules) often appear.

2-Hydroxybenzoic acid (Salicylic acid) penetrates your skin and works to dissolve the dead skin cells clogging your pores.
2-Hydroxybenzoic acid (Salicylic acid) can take several weeks of use for you to see its full effect.

What form and dosage of 2-Hydroxybenzoic acid (Salicylic acid) is recommended for acne?
Your doctor or dermatologist will recommend a form and dosage specifically for your skin type and your skin’s current condition.
They might also recommend that, for 2 or 3 days, you only apply a limited amount to a small area of affected skin to test your reaction before applying to the entire area.

Products with higher concentrations of salicylic acid may be used as exfoliants
2-Hydroxybenzoic acid (Salicylic acid) is also used in higher concentrations as a peeling agent for the treatment of:
-acne
-acne scars
-age spots
-melasma

Does 2-Hydroxybenzoic acid (Salicylic acid) have any side effects?
Although 2-Hydroxybenzoic acid (Salicylic acid) is considered safe overall, it may cause skin irritation when first starting.
It may also remove too much oil, resulting in dryness and potential irritation.

Other potential side effects of 2-Hydroxybenzoic acid (Salicylic acid):
-skin tingling or stinging
-itching
-peeling skin
-adhesives

How does 2-Hydroxybenzoic acid (Salicylic acid) work?
2-Hydroxybenzoic acid (Salicylic acid) works by softening keratin, a protein that forms part of the skin structure.
This helps to loosen dry scaly skin making it easier to remove.
When 2-Hydroxybenzoic acid (Salicylic acid) is used in combination with other medicines it takes off the upper layer of skin allowing the additional medicines to penetrate more effectively.

In acne, topical 2-Hydroxybenzoic acid (Salicylic acid) helps slow down shedding of the cells inside the follicles, preventing clogging.
2-Hydroxybenzoic acid (Salicylic acid) also helps break down blackheads and whiteheads.
2-Hydroxybenzoic acid (Salicylic acid) is an odourless slightly off-white powder or needle-shape crystal compound with the formula C7H6O3.

With many uses spanning a variety of industries including chemical intermediates, pharmaceuticals and cosmetics, 2-Hydroxybenzoic acid (Salicylic acid) is probably most widely known as the main ingredient in cosmetic face washes, cleaners and exfoliants.
With its ability to safely help remove the outer layer of skin and dissolve skin debris 2-Hydroxybenzoic acid (Salicylic acid) is found in a wide range of medicines used to treat a range of dermatological conditions including acne, psoriasis and dermatitis.

2-Hydroxybenzoic acid (Salicylic acid) is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position.
2-Hydroxybenzoic acid (Salicylic acid) is obtained from the bark of the white willow and wintergreen leaves.

2-Hydroxybenzoic acid (Salicylic acid) has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone.
2-Hydroxybenzoic acid (Salicylic acid) is a conjugate acid of a salicylate.

2-Hydroxybenzoic acid (Salicylic acid) is classified as :
-Antidandruff
-Hair conditioning
-Keratolytic
-Masking
-Preservative
-Skin conditioning

CAS Number: 69-72-7
EINECS/ELINCS No: 200-712-3
Restriction (applies to EU only): III/98 VI/3
INN Name: salicylic acid
PHARMACEUTICAL EUROPEAN NAME: acidum salicylicum
Chem/IUPAC Name: Salicylic acid

2-Hydroxybenzoic acid (Salicylic acid) is a lipophilic monohydroxybenzoic acid, a type of phenolic acid, and a beta hydroxy acid (BHA).
2-Hydroxybenzoic acid (Salicylic acid) is widely used in organic synthesis and functions as a plant hormone.
2-Hydroxybenzoic acid (Salicylic acid) is derived from the metabolism of salicin.

In addition to serving as an important active metabolite of aspirin (acetylsalicylic acid), which acts in part as a prodrug to salicylic acid, 2-Hydroxybenzoic acid (Salicylic acid) is probably best known for its use as a key ingredient in topical anti-acne products.
The salts and esters of 2-Hydroxybenzoic acid (Salicylic acid) are known as salicylates.

It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system.
2-Hydroxybenzoic acid (Salicylic acid) is a beta hydroxy acid.
2-Hydroxybenzoic acid (Salicylic acid)’s well-known for reducing acne by exfoliating the skin and keeping pores clear.

2-Hydroxybenzoic acid (Salicylic acid) is found in a variety of over-the-counter (OTC) products.
2-Hydroxybenzoic acid (Salicylic acid) is also available in prescription-strength formulas.
2-Hydroxybenzoic acid (Salicylic acid) works best for mild acne (blackheads and whiteheads) and it can also help prevent future breakouts.

2-Hydroxybenzoic acid (Salicylic acid) has sterilization ability, 2.5% alcohol solution (called spiritus) is used as a topical medicine in the treatment of tinea manus and tinea pedis, also can be made into ointment.
Sodium salicylate can be used for food preservative or preservatives, also can be used for the preparation of toothpaste, mouthwash.

2-Hydroxybenzoic acid (Salicylic acid) has antipyretic and analgesic effects, can cure rheumatism and so on.
2-Hydroxybenzoic acid (Salicylic acid)'s all esters can be used as drug and spices.

Methyl salicylate has pleasant aromas of holly, is used for the preparation of perfume and soap flavor.
The methyl salicylate is coated on the skin, can penetrate into the muscle and let out of 2-Hydroxybenzoic acid (Salicylic acid) to release local pain, so it also can be used for the treatment of pain, contusion, sprain and other medication.

Isoamyl salicylate has orchid aroma, benzyl salicylate has weak ester aroma, both can prepare perfume or soap flavor.
The common name of phenyl salicylate is Salo, was hydrolyzed into phenol and 2-Hydroxybenzoic acid (Salicylic acid) in the intestine , is a kind of effective enteral preservatives.

Another Kind drug related to 2-Hydroxybenzoic acid (Salicylic acid) is para aminosalicylic acid.
2-Hydroxybenzoic acids (Salicylic acid) sodium and calcium salts are used as anti TB drugs for acute exudative pulmonary tuberculosis (TB) and mucosal tuberculosis, is a weak antimicrobial drug, the effect is only 2% of streptomycin, often combined with streptomycin and isoniazid, in order to enhance the curative effect.
2-Hydroxybenzoic acid (Salicylic acid) can be acetylated to the aspirin.

Chemical properties of 2-Hydroxybenzoic acid (Salicylic acid):
1.white needle crystal or crystalline monoclinic edge, spicy.
2-Hydroxybenzoic acid (Salicylic acid) is slightly soluble in water, soluble in acetone, turpentine oil, ethanol, ethyl ether, benzene and chloroform.

2.The acidity of 2-Hydroxybenzoic acid (Salicylic acid) is stronger than benzoic acid, it becomes darker in color in the sun.
In the case of iron ion, 2-Hydroxybenzoic acid (Salicylic acid) becomes into purple chelate.

2-Hydroxybenzoic acid (Salicylic acid) reacts with ferric chloride to show purple, is unstable to heat, easy to decarboxylation to produce phenol heating to 200 ℃.
In Nature salicylic acid mostly is in the form of methyl existing in birch bark oil, content is up to 96%.
There are existing in cinnamon oil, violet oil, wintergreen oil.

Free 2-Hydroxybenzoic acid (Salicylic acid) only a few exist in plants.
2-Hydroxybenzoic acid (Salicylic acid) has double property of phenol and carboxylic acid.

When heated, it is sublimation, and rapid heated, it decomposites to phenol and carbon dioxide.
When react with sodium hydroxide, hydroxyl and carboxyl groups were neutralized to produce the double salt; but with sodium carbonate, only the carboxyl groups are neutralized and build a single salt.

When reacts with alcohol or phenol, 2-Hydroxybenzoic acid (Salicylic acid) can generate the corresponding carboxylic acid ester.
2-Hydroxybenzoic acid (Salicylic acid) is toxic and irritating to the skin, mucous membrane, and reaction with the body tissue protein, so it is corrosive, from another aspect, it can be sterilized

2-Hydroxybenzoic acid (Salicylic acid) belongs to a group of medicines known as keratolytics.
2-Hydroxybenzoic acid (Salicylic acid) is used in the treatment of scaly skin diseases where the skin has become thickened, scaly and flaky.

Topical preparations of 2-Hydroxybenzoic acid (Salicylic acid), either alone or in combination with other medicines, can be used to treat the following common scaly skin conditions:
-Viral warts
-Psoriasis
-Seborrhoeic dermatitis
-Chronic atopic dermatitis
-Lichen simplex
-Ichthyosis
-Acne

Chemical formula: C7H6O3
Molar mass: 138.122 g·mol−1
Appearance: Colorless to white crystals
Odor: Odorless
Density: 1.443 g/cm3 (20 °C)[2]
Melting point: 158.6 °C (317.5 °F; 431.8 K)
Boiling point: 200 °C (392 °F; 473 K) decomposes 211 °C (412 °F; 484 K) at 20 mmHg

Sublimation conditions:
Sublimes at 76 °C

Solubility in water:
1.24 g/L (0 °C)
2.48 g/L (25 °C)
4.14 g/L (40 °C)
17.41 g/L (75 °C)
77.79 g/L (100 °C)

Solubility of 2-Hydroxybenzoic acid (Salicylic acid):
Soluble in ether, CCl4, benzene, propanol, acetone, ethanol, oil of turpentine, toluene

Solubility in benzene:
0.46 g/100 g (11.7 °C)
0.775 g/100 g (25 °C)
0.991 g/100 g (30.5 °C)
2.38 g/100 g (49.4 °C)
4.4 g/100 g (64.2 °C)

Solubility in chloroform:
2.22 g/100 mL (25 °C)
2.31 g/100 mL (30.5 °C)

Solubility in methanol:
40.67 g/100 g (−3 °C)
62.48 g/100 g (21 °C):

Solubility in olive oil: 2.43 g/100 g (23 °C)
Solubility in acetone: 39.6 g/100 g (23 °C)
log P: 2.26
Vapor pressure: 10.93 mPa

Acidity (pKa)
1 = 2.97 (25 °C)
2 = 13.82 (20 °C)

UV-vis (λmax): 210 nm, 234 nm, 303 nm (4 mg % in ethanol)
Magnetic susceptibility (χ): −72.23·10−6 cm3/mol
Refractive index (nD): 1.565

2-Hydroxybenzoic acid (Salicylic acid) is an organic acid often used as the active ingredients in Anti-Acne skin care preparations.
The active of choice when you're looking to clear the skin of almost any build up, whether in the pores, or in the tissues.

2-Hydroxybenzoic acid (Salicylic acid) is a Beta Hydroxy Acid (BHA) and it's activity is completely different from the Alpha Hydroxy Acids (AHA) used in Anti-Aging Skin Care lines.
While the AHA's are small molecules that can get down into the pores quickly, and efficiently, offering enhanced and rapid cellular turn over, BHA's are a larger molecule which doesn't get through the pores as quickly.
The result is that they stay in the pore and continue to work, functioning to break down the build up that is responsible for enlarged pores, acne and inflammatory conditions.

Significantly improve the appearance of acne, Rosacea, & crow's feet as well as being an excellent agent for pore refinement and any condition that is the result of oil build up in the pores and tissues.
2-Hydroxybenzoic acid (Salicylic acid) as a medication is used most commonly to help remove the outer layer of the skin.

As such, 2-Hydroxybenzoic acid (Salicylic acid) is used to treat warts, psoriasis, acne, ringworm, dandruff, and ichthyosis.
Similar to other hydroxy acids, 2-Hydroxybenzoic acid (Salicylic acid) is a key ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis and warts.

Uses in manufacturing of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is used in the production of other pharmaceuticals, including 4-aminosalicylic acid, sandulpiride, and landetimide.
2-Hydroxybenzoic acid (Salicylic acid) was one of the original starting materials for making acetylsalicylic acid (aspirin) in 1897.
Aspirin (acetylsalicylic acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of 2-Hydroxybenzoic acid (Salicylic acid) with the acetyl group from acetic anhydride or acetyl chloride.

Bismuth subsalicylate, a salt of bismuth and salicylic acid, is the active ingredient in stomach relief aids such as Pepto-Bismol, is the main ingredient of Kaopectate and "displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic".
Other derivatives include methyl salicylate used as a liniment to soothe joint and muscle pain and choline salicylate used topically to relieve the pain of mouth ulcers.

Other uses of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is used as a food preservative, a bactericide and an antiseptic.

2-Hydroxybenzoic acid (Salicylic acid) is a useful phosphor in the vacuum ultraviolet spectral range, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.
2-Hydroxybenzoic acid (Salicylic acid) fluoresces in the blue at 420 nm.
2-Hydroxybenzoic acid (Salicylic acid) is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.

Mechanism of action of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) modulates COX1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins.
Salicylate may competitively inhibit prostaglandin formation.

Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms.
2-Hydroxybenzoic acid (Salicylic acid) works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth.

2-Hydroxybenzoic acid (Salicylic acid) inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG.
2-Hydroxybenzoic acid (Salicylic acid) also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor.
The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.

Safety:
17% to 27% 2-Hydroxybenzoic acid (Salicylic acid) used in the form of a paint, and 20% to 50% in plaster form, which are sold for wart and corn removal should not be applied to the face and should not be used for acne treatment.
Even for wart removal, such a solution should be applied once or twice a day – more frequent use may lead to an increase in side-effects without an increase in efficacy.
If high concentrations of salicylic ointment are applied to a large percentage of body surface, high levels of salicylic acid can enter the blood, requiring hemodialysis to avoid further complications.

Chemistry and production of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) crystals under the microscope.
2-Hydroxybenzoic acid (Salicylic acid) has the formula C6H4(OH)COOH, where the OH group is ortho to the carboxyl group.

2-Hydroxybenzoic acid (Salicylic acid) is also known as 2-hydroxybenzoic acid.
2-Hydroxybenzoic acid (Salicylic acid) is poorly soluble in water (2 g/L at 20 °C).

2-Hydroxybenzoic acid (Salicylic acid) is biosynthesized from the amino acid phenylalanine.
In Arabidopsis thaliana it can be synthesized via a phenylalanine-independent pathway.

Sodium salicylate is commercially prepared by treating sodium phenolate (the sodium salt of phenol) with carbon dioxide at high pressure (100 atm) and high temperature (115°C) – a method known as the Kolbe-Schmitt reaction.
Acidification of the product with sulfuric acid gives 2-Hydroxybenzoic acid (Salicylic acid).

2-Hydroxybenzoic acid (Salicylic acid) can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid) or methyl salicylate (oil of wintergreen) with a strong acid or base.
2-Hydroxybenzoic acid (Salicylic acid) degrades to phenol and carbon dioxide at 200 - 230°C:
C6H4OH(CO2H) → C6H5OH + CO2

History of 2-Hydroxybenzoic acid (Salicylic acid):
White willow (Salix alba) is a natural source of 2-Hydroxybenzoic acid (Salicylic acid).
Hippocrates, Galen, Pliny the Elder and others knew that willow bark could ease pain and reduce fevers.

It was used in Europe and China to treat these conditions.
This remedy is mentioned in texts from ancient Egypt, Sumer and Assyria.
The Cherokee and other Native Americans use an infusion of the bark for fever and other medicinal purposes.

In 2014, archaeologists identified traces of salicylic acid on 7th century pottery fragments found in east central Colorado.
The Reverend Edward Stone, a vicar from Chipping Norton, Oxfordshire, England, noted in 1763 that the bark of the willow was effective in reducing a fever.

The active extract of the bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated and named by the German chemist Johann Andreas Buchner in 1828.
A larger amount of the substance was isolated in 1829 by Henri Leroux, a French pharmacist.
Raffaele Piria, an Italian chemist, was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid.

2-Hydroxybenzoic acid (Salicylic acid) was also isolated from the herb meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839.
While their extract was somewhat effective, 2-Hydroxybenzoic acid (Salicylic acid) also caused digestive problems such as gastric irritation, bleeding, diarrhea and even death when consumed in high doses.

Dietary sources of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) occurs in plants as free salicylic acid and its carboxylated esters and phenolic glycosides.
Several studies suggest that humans metabolize 2-Hydroxybenzoic acid (Salicylic acid) in measurable quantities from these plants.

High-salicylate beverages and foods include beer, coffee, tea, numerous fruits and vegetables, sweet potato, nuts, and olive oil, among others.
Meat, poultry, fish, eggs, dairy products, sugar, and breads and cereals have low salicylate content.
Some people with sensitivity to dietary salicylates may have symptoms of allergic reaction, such as bronchial asthma, rhinitis, gastrointestinal disorders, or diarrhea, and so may need to adopt a low-salicylate diet.

Plant hormone:
2-Hydroxybenzoic acid (Salicylic acid) is a phenolic phytohormone and is found in plants with roles in plant growth and development, photosynthesis, transpiration, ion uptake and transport.
2-Hydroxybenzoic acid (Salicylic acid) is involved in endogenous signaling, mediating plant defense against pathogens.
It plays a role in the resistance to pathogens (i.e. systemic acquired resistance) by inducing the production of pathogenesis-related proteins and other defensive metabolites.

The volatile methyl ester of 2-Hydroxybenzoic acid (Salicylic acid) -- methyl salicylate -- can also diffuse through the air, facilitating plant-plant communication.
Methyl salicylate is taken up by the stomata of the nearby plant, where it can induce an immune response after being converted back to 2-Hydroxybenzoic acid (Salicylic acid).

Signal transduction:
A number of proteins have been identified that interact with SA in plants, especially salicylic acid binding proteins (SABPs) and the NPR genes (Nonexpressor of pathogenesis related genes), which are putative receptors.

History of 2-Hydroxybenzoic acid (Salicylic acid):
It was first discovered in 1979 that salicylates are involved in induced defenses of tobacco against tobacco mosaic virus.
In 1987, salicylic acid was identified as the long-sought signal that causes thermogenic plants such as the voodoo lily, Sauromatum guttatum, to heat up.

SPECIFICATIONS of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is a very fine white crystalline powder.
assay 99.5% pure
2-Hydroxybenzoic acid (Salicylic acid) is oil soluble.
2-Hydroxybenzoic acid (Salicylic acid) is alcohol soluble.
Store 2-Hydroxybenzoic acid (Salicylic acid) tightly closed, away from heat sources.
Shelf life of 2-Hydroxybenzoic acid (Salicylic acid) is 3yrs when properly stored.

USAGE GUIDELINES of 2-Hydroxybenzoic acid (Salicylic acid):
-add to the oil phase
-0.5 to 1.0% for sensitive skin products
-2.0% for active treatment products

APPLICATIONS of 2-Hydroxybenzoic acid (Salicylic acid):
-acne / oily skin care lines
-clarifying scalp / hair product lines
-treatment lines
-Rosacea
-dandruff
-warts
-calluses
-crusty skin

TIPS:
When creating water based serums / gels / toners, you may pre-dissolve salicylic acid in NatureSilk, or alcohol, to solubilize it before mixing with water or other liquid

2-Hydroxybenzoic acid (Salicylic acid) is not coated or enhanced.
2-Hydroxybenzoic acid (Salicylic acid) will not dissolve, into alcohol, instantly or without effort.

2-Hydroxybenzoic acid (Salicylic acid) does require mixing in all cases and regardless of solution levels.
2-Hydroxybenzoic acid (Salicylic acid) will incorporate approximately 10% almost instantly.

Beyond a 10% solution you will need to mix it into your alcohol and allow it to rest for approximately one hour or more to incorporate the excess.
This process will vary based on the circumstances of your alcohol and equipment.
Testing to determine the threshold as it relates to your specific conditions is required.

CAUTION :
POWDER IS AIRBORNE - USE AN APPROPRIATE DUST FILTER. IF VENTILATION IS INSUFFICIENT USE AN EFFICIENTLY RATED RESPIRATOR
DO NOT HANDLE WITH BARE HANDS. USE PROTECTIVE GLOVES.
WEAR PROTECTIVE EYE GEAR, TIGHTLY SEALED GOGGLES, WHEN WORKING IN AN ENVIRONMENT WITH EXCESSIVE AIR MOVEMENT

CAUTION :
As with all of the acids, 2-Hydroxybenzoic acid (Salicylic acid) is important to let your skin acclimate to their use.
For those who's skin is not used to the acids a slight stinging and redness may result.

If this occurs, reduce usage to every other day for 2 weeks, before resuming daily application.
If irritation persists, discontinue use.

If you experience anything more than a slight stinging, or redness, discontinue use immediately.
Any time that you experience discomfort, you can apply a 10% solution of sodium bicarbonate (baking soda) to neutralize the acid, then wash with soap and water to thoroughly remove any acid residue.

If irritation develops, or persists, seek medical advise.
Nothing on the Ingredients To Die For website should be considered, or construed, as medical advise.

IT IS THE SOLE RESPONSIBILITY OF THE USER TO READ AND UNDERSTAND THE MSDS PRIOR TO PURCHASING OR USING SALICYLIC ACID USP.
DO NOT APPLY DIRECTLY TO THE SKIN AS CHEMICAL BURNING MAY RESULT.

2-Hydroxybenzoic acid (Salicylic acid) is used on the skin to treat common skin and foot (plantar) warts.
2-Hydroxybenzoic acid (Salicylic acid) helps cause the wart to gradually peel off.

2-Hydroxybenzoic acid (Salicylic acid) is also used to help remove corns and calluses.
2-Hydroxybenzoic acid (Salicylic acid) should not be used on the face or on moles, birthmarks, warts with hair growing from them, or genital/anal warts.
2-Hydroxybenzoic acid (Salicylic acid) is a keratolytic.

2-Hydroxybenzoic acid (Salicylic acid) works by increasing the amount of moisture in the skin and dissolving the substance that causes the skin cells to stick together.
This makes 2-Hydroxybenzoic acid (Salicylic acid) easier to shed the skin cells.

Warts are caused by a virus.
2-Hydroxybenzoic acid (Salicylic acid) does not affect the virus.

How to use 2-Hydroxybenzoic acid (Salicylic acid) topical:

2-Hydroxybenzoic acid (Salicylic acid) preparations:
2-Hydroxybenzoic acid (Salicylic acid) preparations come in many forms and strengths.
Available dosage forms include cream, gel, lotion, ointment, pads, plaster, shampoo, cleanser and topical solution.

Strengths of 2-Hydroxybenzoic acid (Salicylic acid) preparations range from 0.5% up to 30%.
The form and strength chosen depends on the condition that is being treated.

2-Hydroxybenzoic acid (Salicylic acid) topical is used to treat many skin disorders, such as acne, dandruff, psoriasis, seborrheic dermatitis of the skin and scalp, calluses, corns, common warts, and plantar warts, depending on the dosage form and strength of the preparation.
2-Hydroxybenzoic acid (Salicylic acid) is available without a prescription.
Some of these preparations are available only with your doctor's prescription.

2-Hydroxybenzoic acid (Salicylic acid) is available in the following dosage forms:
-Gel/Jelly
-Solution
-Soap
-Pad
-Liquid
-Cream
-Ointment
-Foam
-Lotion
-Patch, Extended Release
-Bandage
-Shampoo

Physical properties of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is white crystalline powder, odorless, first bitter taste then sweet.
2-Hydroxybenzoic acid (Salicylic acid) exists in the nature of willow bark, the leaves and sweet birch.

The chemical formula is C6H4 (OH) (COOH), the melting point is 157-159 ℃.
In the light, 2-Hydroxybenzoic acid (Salicylic acid) gradually discolorated.
The relative density is 1.44.

The boiling point is about 211℃/2.67kPa.
Sublimation at 76℃.

Under the common pressure, 2-Hydroxybenzoic acid (Salicylic acid) rapid thermal decomposited to phenol and carbon dioxide.
2-Hydroxybenzoic acid (Salicylic acid) is soluble in ethanol, ethyl ether, chloroform, benzene, acetone, turpentine oil, insoluble in water.

1g salicylic acid was dissolved in 460ml water, 15ml boil water, 2.7ml ethanol, 3ml acetone, 3ml ether, 42ml chloroform, 135ml benzene, 52ml glycerol turpentine, about 60ml glycerol and 80ml petroleum ether.
Adding sodium phosphate, borax can increase the solubility of 2-Hydroxybenzoic acid (Salicylic acid) in water.

PH of 2-Hydroxybenzoic acid (Salicylic acid) aqueous solution is 2.4.
Alicylic acid reacts with ferric chloride aqueous solution to generat special purple.

Active Ingredients for Acne Medications:
2-Hydroxybenzoic acid (Salicylic acid)—a beta hydroxy acid that also sloughs dead cell buildup within the follicle, acts as a mild antibacterial, and has soothing properties.
2-Hydroxybenzoic acid (Salicylic acid) is regarded to be less irritating than benzoyl peroxide and has less allergy potential, but it is also less aggressive in treating acne.

2-Hydroxybenzoic acid (Salicylic acid) is often used for treating milder forms of acne.
The concentration in OTC drugs is limited to 2 percent.
2-Hydroxybenzoic acid (Salicylic acid) is also used as a performance ingredient exfoliant in smaller concentrations, without making a drug claim.

Pharmacological action:
2-Hydroxybenzoic acid (Salicylic acid) is widely used, eczema, psoriasis, salicylic acid can be used in acne, dandruff.
The concentration of 3%~6% can be used to horny, higher than 6% of salicylic acid can damage to tissue.

Below 40% of concentration is suitable for the treatment of thick cocoon, corns and warts.
2-Hydroxybenzoic acid (Salicylic acid) can also be added in the treatment of acne and dandruff.

Contrast with the beauty effect of acid:
2-Hydroxybenzoic acid (Salicylic acid) (BHA) is extracted from willow bark , holly leaf, also called plant acid; Tartaric acid (AHA) was extracted from sugarcane; two different raw materials extract acid.
The two can control the oil, cutin, remove acne, shrink pores, light print.

More than 50% concentration of the acid change skin can be operated by only the doctor of Department of Dermatology, and no matter how much concentration of salicylic acid, skins are classified as medical treatment, it is worth noting that a few people are not suitable for the use of any concentration of salicylic acid, so the general beauty salon is not executed, below 40% of salicylic acid in the acid skin beauty salon is allowed in law, in contrast, Tartaric acid is safer than salicylic acid.
As for the effect of salicylic acid, salicylic acid only locked in the superficial stratum corneum, just play a simple treatment and blocking effect, changing the skin is only temporary, while the tartaric acid into the true cortex changed fundamentally.

The skin can be cured, the dermal damage formation pox pits, salicylic acid becomes incapable of action, so it can not be called salicylic acid skin, can only be called salicylic acid treatment.
The safety of salicylic acid and tartaric acid and skin effect are different, because tartaric acid is not toxic, use from low to high (8%-15%-20%-30%-40%), slowly adaption is not burn the skin, disfigured and any side effects.
While 2-Hydroxybenzoic acid (Salicylic acid) is toxic, high concentration is not suitable for use in the face, there are certain restrictions on the concentration, the concentration can be used to the skin in the 3%-6%, higher than 6% salicylic acid is corrosive to the skin, a high concentration of 40% salicylic acid has strong corrosion properties of keratin.

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
1.) 2-Hydroxybenzoic acid (Salicylic acid) namely ortho hydroxy benzoic acid (o-hydroxybenzoic acid) is a kind of important organic synthetic raw material.
In pesticide production, 2-Hydroxybenzoic acid (Salicylic acid) is used for synthetic organic phosphorus pesticide Isocarbophos, isofenphos methyl intermediates isopropyl salicylate and Rodenticide warfarin, kill rats ether intermediate 4-hydroxy coumarin; in the pharmaceutical industry, salicylic acid was used as antiseptics, also as intermediates of acetylsalicylic acid (aspirin) and other drugs; it is also an important raw material of dye, spices, such as rubber industry.

2.) 2-Hydroxybenzoic acid (Salicylic acid) is mainly used as raw materials of aspirin feedstock and pesticide aqueous amine and phosphorus products, can also be used in dye industry, refining and chemical reagent, etc.

3.) 2-Hydroxybenzoic acid (Salicylic acid) is used in the pharmaceutical industry for the antipyretic, analgesic, anti-inflammatory, diuretic drugs, industrial dye used for direct of azo dyes and acid mordant dyes, but also for spices, etc.

4.) 2-Hydroxybenzoic acid (Salicylic acid) is used as complexing indicator and preservative.

5.) Verification for aluminum, boron, cerium, copper, iron, lead, manganese, mercury, nickel, silver, titanium, tungsten, vanadium, sulfite, nitrate and nitrite.
Determination of aluminum, copper, iron, thorium, titanium and uranium.
Alkali method and iodometry titration standard.
The fluorescent indicator.
Complexometric indicator.

6.) 2-Hydroxybenzoic acid (Salicylic acid) is an important raw material of medicine, spices, dyes, rubber auxiliaries and other fine chemicals.
In the pharmaceutical industry, 2-Hydroxybenzoic acid (Salicylic acid) itself is used as antiseptics, for local cutin hyperplasia and skin fungal infection.
As for pharmaceutical intermediates, 2-Hydroxybenzoic acid (Salicylic acid) is used for production of ethenzamide, diuretin, acetylsalicylic acid (aspirin), sodium salicylate and salicylamide, glibenclamide niclosamide, salicylic acid, phenyl ester, ethyl p-hydroxybenzoate, bismuth subsalicylate, sulfasalazine and other drugs. In the dye industry, it is used for the production of direct yellow GR, direct grey BL, direct light brown RT, acid mordant brown G, acid mordant yellow GG dye.
2-Hydroxybenzoic acid (Salicylic acid) esters are used as spice, for example, methyl salicylate can be used as toothpaste and other oral spices and other spices and food spices.
2-Hydroxybenzoic acid (Salicylic acid) is used in rubber industry production antiscorching agent, ultraviolet absorbent and foaming agent and water.
2-Hydroxybenzoic acid (Salicylic acid) can also be used as a phenolic resin curing agent, textile printing and dyeing pulp preservatives, synthetic fiber dyeing of the expansion agent (agent) and so on.

Methods of production:
1. The phenol and sodium hydroxide react to produce phenol sodium, distillation and dehydration, CO2 carboxylation reaction to obtain sodium salicylate, then using sulfuric acid and produce crude product.
The crude product through the sublimation refined to the finished product.
Raw materials consumption quota: phenol (98%) 704kg/t, alkali burn (95%) 417kg/t, sulfate (95%) 500kg/t, carbon dioxide (99%) 467kg/t.

2.The preparation method of the method is that the sodium salt of phenol and carbon dioxide can be obtained by acidification.
phenol and liquid caustic soda are produced into solution of the sodium salt of phenol, vacuum drying, and then to 100℃, slowly put to the dry carbon dioxide, when the pressure reaches 0.7~0.8MPa, stop passing carbon dioxide, warming up to 140 to 180℃.
After the reaction with water, sodium salicylate dissolved and decolorization, filtering, coupled with the sulfuric acid, namely precipitation salicylic acid, after filtering, washing and drying to obtain the product.

Description of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) (from Latin salix, willow tree, from the bark of which the substance used to be obtained) is a mono hydroxy benzoic acid, a type of phenolic acid and a beta hydroxy acid.
This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone.

2-Hydroxybenzoic acid (Salicylic acid) is derived from the metabolism of salicin.
In addition to being an important active metabolite of aspirin (acetylsalicylic acid), which acts in part as a prod rug to salicylic acid, it is probably best known for its use in anti-acne treatments.
The salts and esters of 2-Hydroxybenzoic acid (Salicylic acid) are known as salicylates.

Chemical Properties of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) has the formula C6H4(OH) COOH, where the OH group is ortho to the carboxyl group.
2-Hydroxybenzoic acid (Salicylic acid) is also known as 2- hydroxybenzoic acid.

2-Hydroxybenzoic acid (Salicylic acid) is poorly soluble in water (2 g / L at 20 °C).
Aspirin (acetyl salicylic acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride.

Chemical Properties of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is odorless or has a slight phenolic odor with an acrid taste.

Chemical Properties of 2-Hydroxybenzoic acid (Salicylic acid):
Also known as o-hydroxybenzoic acid,C6H4(OH)(COOH) is a white powder with an acrid taste that is stable in air but gradually discolored by light.
2-Hydroxybenzoic acid (Salicylic acid) is soluble in acetone, oil of turpentine, alcohol, ether,benzene; slightly soluble in water,and combustible.
Derived by reacting a hot solution of sodium phenolate with carbon dioxide and acidifying the sodium salt thus formed. Used in the manufacture of aspirin and salicylates, resins, dyestuff intermediate, prevulcanization inhibitor, analytical reagent,and fungicide.

Chemical Properties of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is a white to tan crystalline solid; needles.

Occurrence of 2-Hydroxybenzoic acid (Salicylic acid):
Unripe fruits and vegetables are natural sources of 2-Hydroxybenzoic acid (Salicylic acid), particularly blackberries, blueberries, cantaloupes, dates, raisins, kiwi fruits, guavas, apricots, green pepper, olives, tomatoes, radish and chicory; also mushrooms.
Some herbs and spices contain quite high amounts, although meat, poultry, fish, eggs and dairy products all have little to no salicylates.
Of the legumes, seeds, nuts, and cereals, only almonds, water chestnuts and peanuts have significant amounts.

History of 2-Hydroxybenzoic acid (Salicylic acid):
The Greek physician Hippocrates wrote in the 5th century BC about a bitter powder extracted from willow bark that could ease aches and pains and reduce fevers.
The active extract of the bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated and named by the German chemist Johann Andreas Buchner in 1826.
Raffaele Piria, an Italian chemist was able to convert 2-Hydroxybenzoic acid (Salicylic acid) into a sugar and a second component, which on oxidation becomes salicylic acid.

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is known for its ability to ease aches and pains and reduce fevers.
These medicinal properties, particularly fever relief, have been known since ancient times, and 2-Hydroxybenzoic acid (Salicylic acid) is used as an antiinflammatory drug.

In modern medicine, 2-Hydroxybenzoic acid (Salicylic acid) and its derivatives are used as constituents of some rubefacient products.
For example, methyl salicylate is used as a liniment to soothe joint and muscle pain, and choline salicylate is used topically to relieve the pain of mouth ulcers.
As with other beta hydroxy acids, 2-Hydroxybenzoic acid (Salicylic acid) is a key ingredient in many skin-care products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, and warts.

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
Although toxic in large quantities, 2-Hydroxybenzoic acid (Salicylic acid) is used as a food preservative and as bactericidal and an antiseptic.
For some people with salicylate sensitivity even these small doses can be harmful .

Sodium salicylate is a useful phosphor in the vacuum ultraviolet with nearly flat quantum efficiency for wavelengths between 10 to 100 nm.
2-Hydroxybenzoic acid (Salicylic acid) fluoresces in the blue at 420 nm.
2-Hydroxybenzoic acid (Salicylic acid) is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is a beta-hydroxy acid with keratolytic and antiinflammatory activity.
2-Hydroxybenzoic acid (Salicylic acid) helps dissolve the top layer of stratum corneum cells, improving the look and feel of the skin.

2-Hydroxybenzoic acid (Salicylic acid) is an effective ingredient in acne products and as such is widely used in acne soaps and lotions.
Because it is lipid soluble, 2-Hydroxybenzoic acid (Salicylic acid) can more easily reduce sebaceous follicle blockage by penetrating the pores and exfoliating the cellular buildup.

2-Hydroxybenzoic acid (Salicylic acid) is antimicrobial, anti-septic, enhances the activity of preservatives, and can be used to adjust the pH of products.
For the treatment of aging skin, 2-Hydroxybenzoic acid (Salicylic acid) appears to help improve skin wrinkles, roughness, and tone.

In addition, Salicylic is a useful ingredient for products formulated to treat psoriasis, callouses, corns, and warts-cases where there is a buildup of dead skin cells.
When applied topically, it is reported to penetrate 3 to 4 mm into the epidermis.

A small amount of salicylic acid can convert to copper salicylate, a powerful anti-inflammatory.
When used at high concentrations, 2-Hydroxybenzoic acid (Salicylic acid) may cause skin redness and rashes.
This is a naturally occurring organic acid, related to aspirin.
2-Hydroxybenzoic acid (Salicylic acid) is found in some plants, particularly the leaves of wintergreen, willow bark, and the bark of sweet birch.
2-Hydroxybenzoic acid (Salicylic acid) is also synthetically manufactured.

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is an Impurity of Acetylsalicylic Acid (A187780).
Acetylsalicylic acid Impurity B.

Uses of 2-Hydroxybenzoic acid (Salicylic acid):
non-steroidal anti-inflammatory drugs

Definition of 2-Hydroxybenzoic acid (Salicylic acid):
ChEBI: A monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position.
2-Hydroxybenzoic acid (Salicylic acid) is obtained from the bark of the white willow and wintergreen leaves.

Molecular Weight: 138.12
XLogP3: 2.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 1
Exact Mass: 138.031694049
Monoisotopic Mass: 138.031694049
Topological Polar Surface Area: 57.5 Å²
Heavy Atom Count: 10
Formal Charge: 0
Complexity: 133
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Definition of 2-Hydroxybenzoic acid (Salicylic acid):
A crystalline aromatic carboxylic acid.
2-Hydroxybenzoic acid (Salicylic acid) is used in medicines, as an antiseptic, and in the manufacture of azo dyes.
2-Hydroxybenzoic acids (Salicylic acid) ethanoyl (acetyl) ester is aspirin.

Production Methods of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) may be obtained (1) from oil of wintergreen, which contains methyl salicylate, or (2) by heating dry sodium phenate C6H5ONa plus carbon dioxide under pressure at 130 °C (266 °F) and recovering from the resulting sodium salicylate by adding dilute sulfuric acid.

Indications of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is a β-hydroxy acid that penetrates into the sebaceous gland and has comedolytic and anti-inflammatory properties.
2-Hydroxybenzoic acid (Salicylic acid) can be used as an adjunctive therapy and is found in cleansers, toners, masks, and peels.

2-Hydroxybenzoic acid (Salicylic acid) is keratolytic and at concentrations between 3% and 6% causes softening of the horny layers and shedding of scales.
2-Hydroxybenzoic acid (Salicylic acid) produces this desquamation by solubilizing the intercellular cement and enhances the shedding of corneocytes by decreasing cell-to-cell cohesion.

In concentrations >6%, 2-Hydroxybenzoic acid (Salicylic acid) can be destructive to tissue.
Application of large amounts of the higher concentration of salicylic acid can also result in systemic toxicity.

2-Hydroxybenzoic acid (Salicylic acid) is used in the treatment of superficial fungal infections, acne, psoriasis, seborrheic dermatitis, warts, and other scaling dermatoses.
When 2-Hydroxybenzoic acid (Salicylic acid) is combined with sulfur, some believe that a synergistic keratolytic effect is produced.
Common preparations include a 3% and 6% ointment with equal concentration of sulfur; 6% propylene glycol solution (Keralyt); 5% to 20% with equal parts of lactic acid in flexible collodion for warts (Duofilm, Occlusal); in a cream base at any concentration for keratolytic effects; as a 60% ointment for plantar warts; and in a 40% plaster on velvet cloth for the treatment of calluses and warts (40% salicylic acid plaster).

Preparation of 2-Hydroxybenzoic acid (Salicylic acid):
Prepared by heating sodium phenolate with carbon dioxide under pressure

Production Methods of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is biosynthesized from the amino acid phenylalanine.
In Arabidopsis thaliana it can also be synthesized via a phenylalanine - independent pathway.

Sodium salicylate is commercially prepared by treating sodium phenolate ( the sodium salt of phenol ) with carbon dioxide at high pressure (100 atm ) and high temperature (390K) -a method known as the Kolbe-Schmitt reaction.
Acidification of the product with sulfuric acid gives 2-Hydroxybenzoic acid (Salicylic acid).
2-Hydroxybenzoic acid (Salicylic acid) can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid) or methyl salicylate (oil of winter green) with a strong acid or base.

General Description of 2-Hydroxybenzoic acid (Salicylic acid):
-Odorless white to light tan solid.
-Sinks and mixes slowly with water.

Air & Water Reactions of 2-Hydroxybenzoic acid (Salicylic acid):
Sublimes and forms vapor or dust that may explode.

Reactivity Profile of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic 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 with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.

Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.

Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble 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 Salicylic acid 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.

Hazard:
Respiratory alkalosis, hyperkalemia, hyperthermia, dehydration, convulsions, shock, res- piratory paralysis, respiratory acidosis, lesions and death from respiratory collapse; fetotoxic.

Health Hazard:
Inhalation of dust irritates nose and throat.
Vomiting may occur spontaneously if large amounts are swallowed.

2-Hydroxybenzoic acid (Salicylic acid) contact with eyes causes irritation, marked pain, and corneal injury which should heal.
Prolonged or repeated skin contact may cause marked irritation or even a mild burn.

Purity / Analysis Method: >99.5%(T)
Molecular Formula / Molecular Weight: C7H6O3 = 138.12
Physical State (20 deg.C): Solid
CAS RN: 69-72-7
Reaxys Registry Number: 774890
PubChem Substance ID: 87570635
SDBS (AIST Spectral DB): 1149
Merck Index (14): 8332
MDL Number: MFCD00002439

Mechanism of action of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) has been shown to work through several different pathways.
2-Hydroxybenzoic acid (Salicylic acid) produces its anti - inflammatory effects via suppressing the activity of cyclo oxygenase (COX), an enzyme which is responsible for the production of pro - inflammatory mediators such as the prostaglandins.

Notably, it does this not by direct inhibition of COX, unlike most other non-steroidal anti-inflammatory drugs (NSAIDs), but instead by suppression of the expression of the enzyme (via a yet-un elucidated mechanism).
2-Hydroxybenzoic acid (Salicylic acid) has also been shown to activate adenosine monophosphate-activated protein kinase (AMPK), and it is thought that this action may play a role in the anticancer effects of the compound and its prod rugs aspirin and salsalate.

In addition, the anti diabetic effects of 2-Hydroxybenzoic acid (Salicylic acid) are likely mediated by AMPK activation primarily through allosteric conformational change that increases levels of phosphorylation.
2-Hydroxybenzoic acid (Salicylic acid) also uncouples oxidative phosphorylation which leads to increased ADP:ATP and AMP:ATP ratios in the cell.

Consequently, 2-Hydroxybenzoic acid (Salicylic acid) may alter AMPK activity and subsequently exert its anti-diabetic properties through altered energy status of the cell.
Even in AMPK knock - out mice, however, there is an anti-diabetic effect demonstrating that there is at least one additional, yet - unidentified action of the compound.

Solubility of 2-hydroxybenzoic acid (salicylic acid, with measured melting point of 432 K) in water, 1-propanol, 2-propanol, and 2-propanone was determined at (298.2 to 338.2) K and atmospheric pressure.
Also, the solubility of 2-Hydroxybenzoic acid (Salicylic acid) in binary mixtures of 1-propanol (1) + water (2), 2-propanol (1) + water (2), and 2-propanone (1) + water (2) at 298.2 K and atmospheric pressure was investigated.

Phase separation occurred in x1= 0.114, 0.167 of 1-propanol (1) + water (2) and x1= 0.171, 0.237 of 2-propanone (1) + water (2) mixtures.
The van’t Hoff and Grant equations were used to correlate the solubility of 2-Hydroxybenzoic acid (Salicylic acid) in monosolvents at different temperatures.

The solubility values of 2-Hydroxybenzoic acid (Salicylic acid) in binary mixtures of solvents were calculated using the Jouyban–Acree model.
The mean deviation was used as an error criterion.
The overall mean deviation of correlated solubility data in monosolvents at different temperatures, and in mixed solvents at 298.2 K were 1.0 % and 8.3 %, respectively.

Side effects of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acids (Salicylic acid) side effects include erythema and scaling.

Safety Profile of 2-Hydroxybenzoic acid (Salicylic acid):
Poison by ingestion, intravenous, and intraperitoneal routes.
Moderately toxic by subcutaneous route.

An experimental teratogen.
Human systemic effects by skin contact: ear tinnitus.

A skin and severe eye irritant.
Experimental reproductive effects.

Incompatible with iron salts, spirit nitrous ether, lead acetate, iodine.
2-Hydroxybenzoic acid (Salicylic acid) is used in the manufacture of aspirin.
When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) is used as a topical keratolytic agent; in manufacture of aspirin, salicylates, resins, as a dyestuff intermediate; prevulcanization inhibitor; analytical reagent; fungicide, antiseptic, and food preservative.

Veterinary Drugs and Treatments:
Often combined with sulfur, 2-Hydroxybenzoic acid (Salicylic acid) shampoos are often employed to treat patients with seborrheic disorders (seborrhea sicca and oleosa) exhibiting mild to moderate scaling, with mild waxy and keratinous debris.
2-Hydroxybenzoic acid (Salicylic acid) has mildly antipruritic, antibacterial (bacteriostatic), keratoplastic and keratolytic actions.
Lower concentrations are primarily keratoplastic and higher concentrations, keratolytic.

2-Hydroxybenzoic acid (Salicylic acid) lowers skin pH, increases corneocyte hydration and dissolves the intercellular binder between corneocytes.
2-Hydroxybenzoic acid (Salicylic acid) and sulfur are thought to be synergistic in their keratolytic actions.

Purification Methods of 2-Hydroxybenzoic acid (Salicylic acid):
2-Hydroxybenzoic acid (Salicylic acid) has been purified by steam distillation, by recrystallisation from H2O (solubility is 0.22% at room temperature and 6.7% at 100o), absolute MeOH, or cyclohexane and by sublimation in a vacuum at 76o.
The acid chloride (needles) has m 19-19.5o, b 92o/15mm, the amide has m 133o (yellow needles from H2O), the O-acetyl derivative has m 135o (rapid heating and the liquid resolidifies at 118o), and the O-benzoyl derivative has m 132o (aqueous EtOH).

2-Hydroxybenzoic acid (Salicylic acid) is involved in endogenous signaling, mediating in plant defense against pathogens.
2-Hydroxybenzoic acid (Salicylic acid) plays a role in the resistance to pathogens by inducing the production of pathogenesis-related proteins.

2-Hydroxybenzoic acid (Salicylic acid) is involved in the systemic acquired resistance (SAR) in which a pathogenic attack on one part of the plant induces resistance in other parts.
The signal can also move to nearby plants by salicylic acid being converted to the volatile ester, methyl salicylate.

Incompatibilities of 2-Hydroxybenzoic acid (Salicylic acid):
Iron salts; lead acetate; iodine.
Forms an explosive mixture in air.

Precautions to be aware of before using 2-Hydroxybenzoic acid (Salicylic acid):
Even though salicylic acid is available in OTC products you can pick up at your local grocery store, you should talk with your doctor before using it.

Considerations to discuss include:

Allergies:
Let your doctor know if you’ve experienced allergic reactions to 2-Hydroxybenzoic acid (Salicylic acid) or other topical medications before.

Use in children:
Children may be at more risk of skin irritation.
Speak with a doctor before your child starts using 2-Hydroxybenzoic acid (Salicylic acid) products.

Drug interactions:
Certain medications do not interact well with 2-Hydroxybenzoic acid (Salicylic acid).
Let your doctor know what medications you’re currently taking.
You should also tell a doctor if you have any of the following medical conditions, as these may affect their decision to prescribe 2-Hydroxybenzoic acid (Salicylic acid):
-liver disease
-kidney disease
-blood vessel disease
-diabetes
-chickenpox (varicella)
-flu (influenza)

Other names:
Benzoic acid, 2-hydroxy-
o-Hydroxybenzoic acid
Phenol-2-carboxylic acid
Psoriacid-S-Stift
Retarder W
Rutranex
Salicylic acid collodion
Salonil
2-Hydroxybenzoic acid
Acido salicilico
Keralyt
Kyselina 2-hydroxybenzoova
Kyselina salicylova
Orthohydroxybenzoic acid
Duoplant
Freezone
Ionil
Saligel; Compound W
2-Hydroxybenzenecarboxylic acid
2-Carboxyphenol
o-Carboxyphenol
2-Hydroxybenzoic acid
Benzoic acid, 2-hydroxy-
Salicylic acid
Salicylsäure
200-712-3 [EINECS]
200-835-2 [EINECS]
2-Hydroxybenzenecarboxylic acid
2-hydroxybenzoic acid
2-hydroxy-benzoic acid
69-72-7 [RN]
774890 [Beilstein]
Acid, 2-Hydroxybenzoic
Acid, o-Hydroxybenzoic
Acid, ortho-Hydroxybenzoic
Acid, Salicylic
Acide salicylique [French] [ACD/IUPAC Name]
Acido o-idrossibenzoico [Italian]
Acido salicilico [Italian]
Benzoic acid, 2-hydroxy- [ACD/Index Name]
Benzoic acid, o-hydroxy-
Duofilm [Trade name]
Duoplant [Trade name]
Hydroxybenzenecarboxylic acid
Keralyt [Trade name]
Kyselina 2-hydroxybenzoova [Czech]
Kyselina salicylova [Czech]
o-hydroxybenzoic acid
ortho Hydroxybenzoic Acid
ORTHO-HYDROXYBENZOIC ACID
Salicylic acid [ACD/IUPAC Name] [Wiki]
Salicylsäure [German] [ACD/IUPAC Name]
Verrugon [Trade name]
4-10-00-00125 [Beilstein]
63-36-5 [RN]
78646-17-0 [RN]
Aroall
benzoic acid, hydroxy-
DB00936
Domerine
Entrosalyl
Fostex [Trade name]
Freezone [Trade name]
Glutosalyl
hydroxy benzoic acid
hydroxybenzoic acid
Ionil
Ionil plus
Ionil Plus shampoo
Ionil-Plus
Kerasalicyl
Kerosal
monohydroxy benzoic acid
Nadisal
Neo-salicyl
o-carboxyphenol
Occlusal
o-hydroxy-benzoic acid
Orthohydroxybenzoic acid
ortho-salicylic acid
Pernox
Phenol-2-carboxylic acid
PHENOLIC ACID
PHENOXY, 2-CARBOXY-
QVR BQ [WLN]
Retarder W
Rutranex
sal
salicylic
Salicylic acid 100 Âµg/mL in Methanol
Salicylic acid ACS grade
Salicylic acid, 99%
Salicylic acid, BP, Ph. Eur grade
Salicylic Acid-d4
Saligel
Salisod
Salonil
Salsonin [Trade name]
SAX
Sebucare
Sebulex
Stridex
Stri-Dex
Trans-Ver-Sal
TS-03583
水楊酸 [Chinese]
salicylic acid
2-Hydroxybenzoic acid
69-72-7
o-hydroxybenzoic acid
2-Carboxyphenol
o-Carboxyphenol
Rutranex
Salonil
Retarder W
Keralyt
Duoplant
Freezone
Saligel
Ionil
Psoriacid-S-stift
Benzoic acid, 2-hydroxy-
Stri-Dex
Salicylic acid soap
Salicylic acid collodion
Verrugon
Phenol-2-carboxylic acid
Acidum salicylicum
Trans-Ver-Sal
Orthohydroxybenzoic acid
2-Hydroxybenzenecarboxylic acid
Acido salicilico
Ionil-Plus
Salicylic acid, tech.
Kyselina salicylova
Clear away wart remover
Duofil wart remover
Domerine
Sebucare
Duofilm
Sebulex
Salicyclic acid
Ionil plus
Dr. Scholl's corn removers
Kyselina salicylova [Czech]
Dr. Scholl's callus removers
Dr. Scholl's wart remover kit
Kyselina 2-hydroxybenzoova
Occlusal
Acido salicilico [Italian]
Advanced pain relief corn removers
Caswell No. 731
2-hydroxy-benzoic acid
Kyselina 2-hydroxybenzoova [Czech]
Advanced pain relief callus removers
Acido o-idrossibenzoico [Italian]
NSC 180
Salicylic acid & Sulfur Soap
CCRIS 6714
HSDB 672
AI3-02407
UNII-O414PZ4LPZ
MFCD00002439
EPA Pesticide Chemical Code 076602
BRN 0774890
CHEBI:16914
CHEMBL424
O414PZ4LPZ
MLS000069653
NSC180
Salicylic acid inclusion complex
K 537
NSC-180
ATA fraction 10, ammonium salt
NCGC00159447-05
SMR000059163
Mediplast pads
Salicylic acid, 99+%
Akurza Lotion
Hydrisalic Gel
Akurza Cream
Salex Lotion
Salex Cream
DSSTox_CID_6368
DuoPlant Gel
DHS Sal Shampoo
DSSTox_RID_78106
P&S Shampoo
DSSTox_GSID_26368
Salicylic acid [USAN:JAN]
Acido o-idrossibenzoico
Durasal
Salicylic acid, 99+%, ACS reagent
salicylicum acidum
CAS-69-72-7
Propa pH Peel-Off Acne Mask
NSC629474
phenol derivative, 7
Salicylic acid (TN)
Benzoic acid, 2-hydroxy-, ion(1-)
Benzoic acid, hydroxy-
EINECS 200-712-3
Salicylic acid [USP:JAN]
Azurechelin
Salicylic acid (6CI,8CI)
Anti-blemish
Salicylic acid rs
hydroxy-benzoic acid
ortho-salicylic acid
CMC_13852
Fostex (Salt/Mix)
Pernox (Salt/Mix)
Duofilm Wart Remover
Phenol-2-carboxylate
Duofilm (Salt/Mix)
Salicylic Acid,(S)
Sebulex (Salt/Mix)
2-hydroxobenzoic acid
Domerine (Salt/Mix)
Sebucare (Salt/Mix)
2-Hydroxybenzoate, I
Natural Salicylic Acid
o-hydroxy benzoic acid
2-hydroxy benzoic acid
Spectrum_000948
Salicylic acid,medicinal
ACMC-1AZIK
Opera_ID_582
Sulfasalazine Impurity H
Salicylic acid ACS grade
[O]C(=O)c1ccccc1O
WLN: QVR BQ
Benzoic acid, o-hydroxy-
Bazuka Extra Strength Gel
2-Hydroxybenzenecarboxylate
bmse000252
Epitope ID:124929
Retarder SAX (Salt/Mix)
UPCMLD-DP126
EC 200-712-3
SCHEMBL1967
Oprea1_040343
KBioSS_001428
KSC203I1R
ARONIS27188
BIDD:ER0602
DivK1c_000301
Salicylic acid (JP17/USP)
2-Hydroxybenzoic Acid, Natural
FEMA3985