L-Malic acid is the naturally occurring isomer of malic acid, found mainly in sour and unripe fruits.
L-Malic acid is the most typical acid occurring in fruits, L-Malic acid contributes to sour tastes.
L-Malic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.
CAS Number: 97-67-6
EC Number: 202-601-5
Molecular Formula: C4H6O5
Molecular Weight (g/mol): 134.087
L-Malic acid is an organic compound with the molecular formula C4H6O5.
L-Malic acid is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive.
L-Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
The salts and esters of malic acid are known as malates.
The malate anion is an intermediate in the citric acid cycle.
L-Malic acid is the naturally occurring isomer of malic acid, found mainly in sour and unripe fruits.
L-Malic acid is the most typical acid occurring in fruits, L-Malic acid contributes to sour tastes.
L-Malic acid is commonly used in beverages, confectionary and personal care products.
L-Malic acid, a hydroxydicarboxylic acid, is found in all forms of life.
L-Malic acid exists naturally only as the L-enantiomer.
L-Malic acid should not be confused with the similar sounding maleic and malonic acids.
L-Malic acid gives many fruits, particularly apples, their characteristic flavor.
L-Malic acid is often referred to as “apple acid”.
The word malic is derived from the Latin mālum, for which Malus, the genus that contains all apple species, is also named.
The global market size for malic acid (natural and manufactured1) is ≈US$200 million; the US market is ≈$35 million.
The primary end use in the United States is for flavoring beverages, foods, and confectionaries, with much smaller quantities used in cosmetics and personal care products.
The price of malic acid ranges from US$0.90 to $10.00/kg, depending on the purity, quantity, and end use.
L-Malic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.
Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.
L-Malic acid is a relevant component of the citric acid cycle that is found in animals, plants and microorganisms.
L-Malic acid is one of the most important fruit acids found in nature and L-Malic acid is the acid present in highest concentrations in wine.
L-Malic acid may be used in food production because L-Malic acid is a stronger acid than citric acid.
Microbial decomposition of L-Malic acid leads to the formation of L-lactate; this can be a desirable reaction in the wine industry, where the level of L-Malic acid is monitored, along with L-lactic acid, during malolactic fermentation.
L-Malic acid may be used as a food preservative (E296) or flavour enhancing additive.
L-Malic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
L-Malic acid is used at industrial sites.
L-Malic acid is a dicarboxylic acid and organic compound made by all living organisms.
L-Malic acid is responsible for the sour taste of most fruits and is utilized as a food additive.
Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
L-Malic acid is nearly odorless with a tart, acidic taste.
L-Malic acid is nonpungent.
L-Malic acid is an organic acid that is commonly found in wine.
L-Malic acid plays an important role in wine microbiological stability.
L-Malic acid can be prepared by hydration of maleic acid; by fermentation from sugar.
Occurs in maple sap, apple, melon, papaya, beer, grape wine, cocoa, sake, kiwifruit and chicory root.
L-Malic acid is an organic compound with the molecular formula C4H6O5.
L-Malic acid is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive.
L-Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
The salts and esters of L-Malic acid are known as malates.
The malate anion is an intermediate in the citric acid cycle.
L-Malic acid, a hydroxydicarboxylic acid, is found in all forms of life.
L-Malic acid exists naturally only as the L-enantiomer.
L-Malic acid should not be confused with the similar sounding maleic and malonic acids.
L-Malic acid is L-hydroxysuccinic acid, by enzyme engineering method or fermentation method and separation and purification.
The content of C4H6Os shall not be less than 99.0% calculated as anhydrous.
L-Malic acid gives many fruits, particularly apples, their characteristic flavor.
L-Malic acid is often referred to as “apple acid”.
The word malic is derived from the Latin mālum, for which Malus, the genus that contains all apple species, is also named.
L-Malic acid is a dicarboxylic acid that is found in many fruits and vegetables.
L-Malic acid is the substrate for the enzyme malate dehydrogenase, which catalyzes the oxidation of L-malate to oxaloacetate.
L-Malic acid is used to study mitochondrial function, as L-Malic acid can be used as an alternative energy source.
The L-Malic acid monosodium salt (LAM) has been shown to be effective in preventing muscle damage caused by exercise.
This may be due to L-Malic acid's ability to decrease oxidative stress and increase ATP production through increased mitochondrial activity.
L-Malic acid also has been shown to promote photoreceptor cell survival and improve retinal function in animals with damaged photoreceptors, although L-Malic acid does not have any effect on normal animal eyes.
L-Malic acid, is an alpha-hydroxy organic acid, is sometimes referred to as a fruit acid.
L-Malic acid is found in apples and other fruits.
L-Malic acid is also found in plants and animals, including humans.
In fact, L-Malic acid, in the form of L-Malic acid anion malate, is a key intermediate in the major biochemical energy-producing cycle in cells known as the citric acid or Krebs cycle located in the cells' mitochondria.
L-Malic acid is used in many food products and is a very popular product in beverages and sweets.
L-Malic acid, also known as apple acid and hydroxysuccinic acid, is a chiral molecule.
L-Malic acid, disodium salt is a dicarboxylic acid used to differentiate microorganisms based on their varying metabolic properties.
L-Malic acid is a source of CO2 in the Calvin cycle and an intermediate of the citric acid cycle.
L-Malic acid, is a naturally occurring carboxylic acid abundantly present in the human body.
This acid is not only found in the human body but also occurs naturally in a wide range of foods.
Moreover, L-Malic acid is produced during the fermentation of carbohydrates.
Beyond L-Malic acid biological significance, L-Malic acid finds application in diverse industrial sectors.
L-Malic acid contributes to the production of plastics, solvents, and detergents.
However, the precise mechanism of action of L-Malic acid remains partially understood.
L-Malic acid is hypothesized to be involved in ATP production and the transport of electrons within the electron transport chain.
Furthermore, L-Malic acid is believed to partake in the metabolism of carbohydrates, fats, and proteins.
L-Malic acid is a dicarboxylic acid found in fruits and vegetables, especially apples.
The name malic acid comes from the Latin word for apple, mālum.
Many fruits owe their tart and sour flavors to malic acid.
The salts and esters of malic acid are known as malate.
Many supplements bond to malate to improve their bioavailability, such as citrulline malate and magnesium malate.
Malate is also part of the citric acid cycle (CAC), sometimes referred to as the Krebs cycle or the tricarboxylic acid cycle (TCA).
The CAC is the primary pathway that delivers energy to all areas of the body.
The CAC uses malate to produce NADPH, which then converts to NADH.
NADH is essential for producing adenosine triphosphate (ATP), also known as the energy currency for cells.
ATP provides the necessary energy for various chemical reactions and biochemical processes that occur throughout the body.
L-Malic acid has many uses in food, beverage, pharmaceutical, chemical and medical industries.
L-Malic acid can be produced by one-step fermentation, enzymatic transformation of fumaric acid to L-malate and acid hydrolysis of polymalic acid.
However, the process for one-step fermentation is preferred as L-Malic acid has many advantages over any other process.
The pathways of L-Malic acid biosynthesis in microorganisms are partially clear and three metabolic pathways including non-oxidative pathway, oxidative pathway and glyoxylate cycle for the production of L-Malic acid from glucose have been identified.
Usually, high levels of L-malate are produced under the nitrogen starvation conditions, L-malate, as a calcium salt, is secreted from microbial cells and CaCO3 can play an important role in calcium malate biosynthesis and regulation.
However, L-Malic acid is still unclear how L-Malic acid is secreted into the medium.
To enhance L-malate biosynthesis and secretion by microbial cells, L-Malic acid is very important to study the mechanisms of L-Malic acid biosynthesis and secretion at enzymatic and molecular levels.
L-Malic acid is formed as a by-product of the metabolic processes of sugars and occurs under several names, such as:
Hydroxysuccinic acid,
2-hydroxybutanedioic acid,
Acidum malicum,
Malic acid,
Acidity regulator E296.
L-Malic acid is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive.
KEYWORDS:
97-67-6, 202-601-5, 2-Hydroxybutanedioic acid, hydroxysuccinic acid, Butanedioic acid hydroxy-, Malic acid DL-, Pomalus acid, Deoxytetraric acid, alpha-Hydroxysuccinic acid, Caswell No. 537
Malic acid belongs to the group of natural hydroxy acids.
This means that the molecule contains a hydroxyl group, consisting of oxygen (O) and hydrogen (H).
The structural formula of acidum malicum is as follows:
HOOC–CH(OH)–CH2–COOH.
The molecular formula for malic acid is: C4H6O5.
As an optically active compound, this acid is classified into two forms:
L-Malic acid (left-handed form, found in fruits),
D-malic acid (right-handed form, does not occur in nature).
As a result of industrial treatment of hydroxysuccinic acid, a mixture in the form of a racemate (DL-Malic acid), which has no optical activity, is formed.
Applications of L-Malic acid:
L-Malic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.
Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.
L-Malic acid may be used to prepare:
Diethyl (S)-malate
Ethyl (R)-2-hydroxyl-4-phenylbutanoate
Ethyl (S)-2-hydroxyl-4-phenylbutanoate
D-homophenylalanine ethyl ester hydrochloride
Furo[3,2-i]indolizines
Uses of L-Malic acid:
L-Malic acid may improve dry mouth, dry mouth caused by medication in particular.
L-Malic acid helps produce more saliva due to L-Malic acid sour flavor.
One six-week study examined the effects of a L-Malic acid spray solution on dry mouth compared to a placebo.
The L-Malic acid group had noticeably improved dry mouth symptoms and better saliva flow than the placebo group.
Another two-week trial produced similar results.
Most individuals tolerate malic acid well, given that L-Malic acid’s a common compound in many fruits and vegetables.
L-Malic acid may cause mild side effects, including nausea, diarrhea, and headaches.
Individuals taking medications to lower their blood pressure should consult with a physician before taking malic acid supplements, as they may lower blood pressure.
Kidney stones are painful and can affect many people.
L-Malic acid has been researched for L-Malic acid potential role in preventing and treating kidney stones.
In one preliminary study set in a lab, L-Malic acid was found to increase urine pH levels, making kidney stone formation less likely.
The researchers concluded that L-Malic acid supplementation might help treat calcium kidney stones.4
A 2016 review on the importance of a healthy diet to prevent kidney stones suggested pears could be a potential treatment option.
Per the review, the L-Malic acid in pears may be used to prevent the formation of kidney stones.
This is because L-Malic acid is a precursor for citrate, a compound that inhibits crystal growth in the kidneys.
L-Malic acid contains natural emollient ingredients, which can remove wrinkles on the skin surface, make the skin become tender and white, smooth and elastic, so in the cosmetic formula favored; L-Malic acid can be formulated a variety of flavors, spices, for a variety of daily chemical products, such as toothpaste, shampoo, etc.
L-Malic acid is used abroad to replace citric acid as a new type of detergent additive for the synthesis of high-grade special detergents.
L-Malic acid can be used in pharmaceutical preparations, tablets, syrup, can also be mixed into the amino acid solution, can significantly improve the absorption rate of amino acids; L-Malic acid can be used for the treatment of liver disease, anemia, low immunity, uremia, hypertension, liver failure and other diseases, and can reduce the toxic effect of anticancer drugs on normal cells; Can also be used for the preparation and synthesis of insect repellents, anti-Tartar agents.
In addition, L-Malic acid can also be used as industrial cleaning agent, resin curing agent, synthetic material plasticizer, feed additive, etc.
L-Malic acid is used to resolve α-phenylethylamine, a versatile resolving agent in L-Malic acid own right.
L-Malic acid is found in unripe apples and other fruit.
L-Malic acid is used to make wine, stucco (plaster), cosmetics, pharmaceuticals, dentifrices, and coumarin derivatives.
L-Malic acid is also used as a chelating agent, metal cleaner, electroplating chemical, acidulant, discoloration inhibitor, food flavor, and antioxidant for fats and oils.
L-Malic acid is naturally occurring biochemical that can be converted into citric acid in the citric acid cycle.
L-Malic acid is used as a preservative in animal feeds.
L-Malic acid is used as a flavoring agent and acidity regulator in food.
L-Malic acid is permitted for use as an inert ingredient in non-food pesticide products
L-Malic acid is intermediate in chemical synthesis.
L-Malic acid is chelating and buffering agent.
L-Malic acid is flavoring agent, flavor enhancer and acidulant in foods.
L-Malic acid is manufacture of various esters and salts, wine manufacture, chelating agent, food acidulant, flavoring.
Natural acids of organic origin have long been used in industry.
L-Malic acid serves, among others, as a preservative and acidity regulator – such as the popular E296 – that’s added to:
Preserves,
Jams,
Marmalade,
Candy,
Jellies, etc.
In food production, an ingredient called E296 is used as one of the best citric acid substitutes.
L-Malic acid makes the products stay fresh and attractive for longer.
The acid is effective in impeding the appearance of clouding and the loss of colour of various substances.
In chemical industry, L-Malic acid is also useful in the process of organic synthesis.
Thanks to this, L-Malic acid is possible to obtain, among others, esters used in the production of cleaning agents and cosmetics.
Manufacturers in the pharmaceutical industry make good use of the beneficial properties of acidum malicum.
Organic acid is a healthy stimulant for the digestive system and improves the condition of the epidermis, and therefore L-Malic acid is used as an ingredient in medicinal rinses, capsules and dietary supplements.
Use in cosmetics and the beauty industry:
The antibacterial, stabilising, preserving and brightening properties of acidum malicum are appreciated especially by manufacturers from the cosmetic and beauty industries.
Malic acid is used as an ingredient in many cosmetics for everyday use, such as:
Moisturising and anti-wrinkle creams,
Brightening masks for face and hair,
Shampoos and hair rinses (including bleaches, colour fixers),
Regenerating and cleansing milks and tonics (soothing, brightening, anti-acne),
Natural rinses for hair and nails.
In recent years, people associated with the beauty industry have also become interested in malic acid.
This antibacterial and antioxidant compound is more and more often used for specialised cosmetology treatments for skin and hair.
Among others, these are:
Brightening masks,
Exfoliating scrubs for the face and body,
Aesthetic anti-ageing treatments.
Treatments with malic acid are aimed at improving the condition of the epidermis, inhibiting bacterial growth and the ageing of cells.
Exposing the skin to intense acid action also helps to get rid of discolouration, blemishes and shrink unattractive-looking pores.
Uses at industrial sites:
L-Malic acid is used in the following products: laboratory chemicals and pharmaceuticals.
L-Malic acid is used for the manufacture of: chemicals.
Release to the environment of L-Malic acid can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Industry Uses:
Cleaning agent
Not Known or Reasonably Ascertainable
Other (specify)
Preservative
Process regulators
Consumer Uses:
Not Known or Reasonably Ascertainable
Other (specify)
Preservative
Process regulators
Industrial Processes with risk of exposure:
Acid and Alkali Cleaning of Metals
Electroplating
Farming (Feed Additives)
Plant defense of L-Malic acid:
Soil supplementation with molasses increases microbial synthesis of MA.
This is thought to occur naturally as part of soil microbe suppression of disease, so soil amendment with molasses can be used as a crop treatment in horticulture.
Benefits of L-Malic acid:
Potential L-Malic acid Benefits For Exercise Performance:
L-Malic acid may improve exercise performance by boosting energy and decreasing muscle fatigue.
L-Malic acid also enhances the absorption of other sports performance enhancers like creatine and citrulline.
One study found that a creatine-malate combination improved several aspects of athletes’ running performance, including peak power, distance traveled, hormone levels, and total work.
Bonding malic acid with citrulline produces citrulline malate.
L-Malic acid enhances citrulline’s innate ability to improve nitric oxide levels, remove muscle waste, increase energy, and reduce muscle soreness.
Potential Malic Acid Benefits For Dry Mouth:
L-Malic acid may improve dry mouth, dry mouth caused by medication in particular.
L-Malic acid helps produce more saliva due to L-Malic acid sour flavor.
One six-week study examined the effects of a malic acid spray solution on dry mouth compared to a placebo.
L-Malic acid group had noticeably improved dry mouth symptoms and better saliva flow than the placebo group.
Another two-week trial produced similar results.
Biochem/physiol Actions of L-Malic acid:
L-Malic acid is a part of cellular metabolism.
L-Malic acid's application is recognized in pharmaceutics.
L-Malic acid is useful in the treatment of hepatic malfunctioning, effective against hyper-ammonemia.
L-Malic acid is used as a part of amino acid infusion.
L-Malic acid also serves as a nanomedicine in the treatment of brain neurological disorders.
A TCA (Krebs cycle) intermediate and partner in the L-Malic acid aspartate shuttle.
L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically.
Malate plays an important role in biochemistry.
In the C4 carbon fixation process, malate is a source of CO2 in the Calvin cycle.
In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate.
L-Malic acid can also be formed from pyruvate via anaplerotic reactions.
L-Malic acid is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves.
L-Malic acid , as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell.
The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.
General Manufacturing Information of L-Malic acid:
Industry Processing Sectors:
All Other Basic Inorganic Chemical Manufacturing
Computer and Electronic Product Manufacturing
Food, beverage, and tobacco product manufacturing
Not Known or Reasonably Ascertainable
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Biochemistry of L-Malic acid:
L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically.
L-Malic acid plays an important role in biochemistry.
In the C4 carbon fixation process, malate is a source of CO2 in the Calvin cycle.
In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate.
L-Malic acid can also be formed from pyruvate via anaplerotic reactions.
L-Malic acid is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves.
L-Malic acid, as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell.
The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.
In food:
L-Malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785.
Antoine Lavoisier in 1787 proposed the name acide malique, which is derived from the Latin word for apple, mālum—as is L-Malic acid genus name Malus.
In German L-Malic acid is named Äpfelsäure (or Apfelsäure) after plural or singular of a sour thing from the apple fruit, but the salt(s) are called Malat(e).
Malic acid is the main acid in many fruits, including apricots, blackberries, blueberries, cherries, grapes, mirabelles, peaches, pears, plums, and quince and is present in lower concentrations in other fruits, such as citrus.
L-Malic acid contributes to the sourness of unripe apples.
Sour apples contain high proportions of the acid.
L-Malic acid is present in grapes and in most wines with concentrations sometimes as high as 5 g/L.
L-Malic acid confers a tart taste to wine; the amount decreases with increasing fruit ripeness.
The taste of malic acid is very clear and pure in rhubarb, a plant for which L-Malic acid is the primary flavor.
L-Malic acid is also the compound responsible for the tart flavor of sumac spice.
L-Malic acid is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips.
In citrus, fruits produced in organic farming contain higher levels of malic acid than fruits produced in conventional agriculture.
The process of malolactic fermentation converts malic acid to much milder lactic acid.
Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism.
L-Malic acid, when added to food products, is denoted by E number E296.
L-Malic acid is sometimes used with or in place of the less sour citric acid in sour sweets.
These sweets are sometimes labeled with a warning stating that excessive consumption can cause irritation of the mouth.
L-Malic acid is approved for use as a food additive in the EU, US and Australia and New Zealand (where L-Malic acid is listed by its INS number 296).
L-Malic acid contains 10 kJ (2.39 kilocalories) of energy per gram.
Pharmacology and Biochemistry of L-Malic acid:
Bionecessity:
L-Malic acid is an intermediate in the citric acid cycle.
L-Malic acid is formed from fumaric acid and is oxidized to oxaloacetic acid.
L-Malic acid is also metabolized to pyruvic acid by malic enzyme which is present in many biologic systems, including bacteria and plants.
L-Malic and dL-Malic acid are both rapidly metabolized in the rat.
Orally or ip administered l- or dL-Malic acid was extensively eliminated as carbon dioxide (83 to 92%).
No differences between the two forms were found in the rates (90 to 95% in 24 hr) or routes of excretion.
Malate occurs in all living organisms as an intermediate in the citric acid cycle.
L-Malic acid occurs in relatively high amounts in many fruits and vegetables.
L-Malic acid has two stereoisomeric forms (L- and D-enantiomers), although only the L-isomer exists naturally.
Production and Main Reactions of L-Malic acid:
Racemic malic acid is produced industrially by the double hydration of maleic anhydride.
In 2000, American production capacity was 5,000 tons per year.
The enantiomers may be separated by chiral resolution of the racemic mixture.
S-Malic acid is obtained by fermentation of fumaric acid.
Self-condensation of malic acid in the presence of fuming sulfuric acid gives the pyrone coumalic acid.
Note that this scheme is incorrect. 4 H2O and 2 CO (carbon monoxide, not carbon dioxide) are liberated during the condensation.
Malic acid was important in the discovery of the Walden inversion and the Walden cycle, in which (−)-malic acid first is converted into (+)-chlorosuccinic acid by action of phosphorus pentachloride.
Wet silver oxide then converts the chlorine compound to (+)-malic acid, which then reacts with PCl5 to the (−)-chlorosuccinic acid.
The cycle is completed when silver oxide takes L-Malic acid back to (−)-malic acid.
Etymology of L-Malic acid:
The word 'malic' is derived from Latin 'mālum', meaning 'apple'.
The related Latin word mālus, meaning 'apple tree', is used as the name of the genus Malus, which includes all apples and crabapples; and the origin of other taxonomic classifications such as Maloideae, Malinae, and Maleae.
Handling and storage of L-Malic acid:
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed.
Dry.
Storage class:
Storage class (TRGS 510): 11: Combustible Solids
Stability and reactivity of L-Malic acid:
Reactivity:
The following applies in general to flammable organic substances and mixtures:
In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.
Chemical stability:
L-Malic acid is chemically stable under standard ambient conditions (room temperature).
Possibility of hazardous reactions:
Violent reactions possible with:
Bases
Oxidizing agents
Reducing agents
Alkali metals
Conditions to avoid:
Heat.
First aid measures of L-Malic acid:
General advice:
Show L-Malic acid safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Fresh air.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
If swallowed
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
Firefighting measures of L-Malic acid:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from L-Malic acid or mixture:
Carbon oxides
Combustible.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental release measures of L-Malic acid:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel:
Avoid inhalation of dusts.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions,
Take up dry.
Dispose of properly.
Clean up affected area.
Avoid generation of dusts.
Identifiers of L-Malic acid:
CAS Number: 6915-15-7
ChEBI:
CHEBI:6650
CHEBI:30796 D-(+)
CHEBI:30797 L-(–)
ChEMBL: ChEMBL1455497
ChemSpider:
510
83793 D-(+)-malic acid
193317 L-(–)-malic acid
ECHA InfoCard: 100.027.293
EC Number: 230-022-8
E number: E296 (preservatives)
IUPHAR/BPS: 2480
KEGG:
C00711
C00497 D-(+)
C00149 L-(–)
PubChem CID:
525
92824 D-(+)
222656 L-(–)
UNII: 817L1N4CKP
CompTox Dashboard (EPA): DTXSID0027640
InChI: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N
InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
Key: BJEPYKJPYRNKOW-UHFFFAOYAM
SMILES: O=C(O)CC(O)C(=O)O
CAS: 97-67-6
Molecular Formula: C4H6O5
Molecular Weight (g/mol): 134.087
MDL Number: MFCD00064213
InChI Key: BJEPYKJPYRNKOW-REOHCLBHSA-N
PubChem CID: 222656
ChEBI: CHEBI:30797
IUPAC Name: (2S)-2-hydroxybutanedioic acid
SMILES: C(C(C(=O)O)O)C(=O)O
Synonym(s): (S)-(−)-2-Hydroxysuccinic acid, L-Hydroxybutanedioic acid
Linear Formula: HO2CCH2CH(OH)CO2H
CAS Number: 97-67-6
Molecular Weight: 134.09
Beilstein: 1723541
EC Number: 202-601-5
MDL number: MFCD00064213
PubChem Substance ID: 24896463
NACRES: NA.22
CAS number: 97-67-6
EC number: 202-601-5
Hill Formula: C₄H₆O₅
Chemical formula: HOOCCH(OH)CH₂COOH
Molar Mass: 134.08 g/mol
HS Code: 2918 19 98
Properties of L-Malic acid:
Chemical formula: C4H6O5
Molar mass: 134.09 g/mol
Appearance: Colorless
Density: 1.609 g⋅cm−3
Melting point: 130 °C (266 °F; 403 K)
Solubility in water: 558 g/L (at 20 °C)
Acidity (pKa): pKa1 = 3.40
pKa2 = 5.20
Quality Level: 200 - 300
Assay: ≥95% (titration)
form: powder
pKa (25 °C): (1) 3.46, (2) 5.10
mp: 101-103 °C (lit.)
solubility: water: 100 mg/mL, clear to very slightly hazy, colorless
SMILES string: O[C@@H](CC(O)=O)C(O)=O
InChI: 1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI key: BJEPYKJPYRNKOW-REOHCLBHSA-N
Boiling point: 140 °C (decomposition)
Density: 1.60 g/cm3 (20 °C)
Melting Point: 98 - 103 °C
pH value: 2.2 (10 g/l, H₂O, 20 °C)
Bulk density: 600 kg/m3
Solubility: 160 g/l
Molecular Weight: 134.09 g/mol
XLogP3: -1.3
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Rotatable Bond Count: 3
Exact Mass: 134.02152329 g/mol
Monoisotopic Mass: 134.02152329 g/mol
Topological Polar Surface Area: 94.8Ų
Heavy Atom Count: 9
Complexity: 129
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of L-Malic acid:
Assay (acidimetric): ≥ 99.0 %
Melting range (lower value): ≥ 98 °C
Melting range (upper value): ≤ 104 °C
Spec. rotation [α²0/D (c=5 in pyridine): -30.0 - -27.0 °
Identity (IR): passes test
Melting Point: 100°C to 106°C
Color: White
Density: 1.6
Flash Point: 220°C (428°F)
Quantity: 2.5 kg
Beilstein: 1723541
Merck Index: 14,5707
Solubility Information: Soluble in water(363g/L).
Optical Rotation: −26° (c=5.5 in pyridine)
Formula Weight: 134.09
Percent Purity: 99%
Physical Form: Crystalline Powder
Chemical Name or Material: L-(-)-Malic acid
Related compounds of L-Malic acid:
Butanol
Butyraldehyde
Crotonaldehyde
Sodium malate
Other anions:
Malate
Related carboxylic acids:
Succinic acid
Tartaric acid
Fumaric acid
Related Products of L-Malic acid:
2,3-Dichlorophenoxyacetic Acid
D674580
rac Geosmin
Germacrene D (~90%) (Stabilized with Hydroquinone)
Germacrene D-d3
Names of L-Malic acid:
Regulatory process names:
(-)-Hydroxysuccinic acid
(-)-Malic acid
2-Hydroxybutanedioic acid, (S)-
Apple acid
Butanedioic acid, 2-hydroxy-, (2S)-
Butanedioic acid, hydroxy-, (2S)-
Butanedioic acid, hydroxy-, (S)-
Butanedioic acid, hydroxy-, (S)- (9CI)
Hydroxybutanedioic acid, (S)-
Hydroxysuccinnic acid (-)
L-(-)-Malic acid
L-malic acid
L-malic acid
Malic acid L-(-)-form
Malic acid, L-
S-(-)-Malic acid
S-2-Hydroxybutanedioic acid
IUPAC names:
(2S)-2-hydroxybutanedioic acid
(S)-(−)-2-Hydroxysuccinic acid
2-hydroxybutanedioic acid
Butenedioic acid
L(-)-Malic acid
L-(-)-Malic Acid
L-(-)-Äpfelsäure
L-Hydroxybutanedioic acid
L-Hydroxysuccinic acid
l-hydroxysuccinic acid
L-Malic Acid
L-Malic acid
L-malic acid
L-malic acid
malic acid
S-2-Hydroxybutanedioic acid
S-HYDROXYBUTANEDIOIC ACID
Preferred IUPAC name:
2-Hydroxybutanedioic acid
Trade names:
Acido Malico
L-(-)-Malic acid
Other names:
Hydroxybutanedioic acid
2-Hydroxysuccinic acid
(L/D)-Malic acid
(±)-Malic acid
(S/R)-Hydroxybutanedioic acid
Other identifiers:
124501-05-9
498-37-3
6294-10-6
84781-39-5
97-67-6
Synonyms of L-Malic acid:
malic acid
DL-malic acid
6915-15-7
2-Hydroxybutanedioic acid
2-Hydroxysuccinic acid
617-48-1
malate
hydroxysuccinic acid
Butanedioic acid, hydroxy-
Malic acid, DL-
Kyselina jablecna
hydroxybutanedioic acid
Pomalus acid
Deoxytetraric acid
Hydroxybutandisaeure
Musashi-no-Ringosan
alpha-Hydroxysuccinic acid
Caswell No. 537
Monohydroxybernsteinsaeure
Succinic acid, hydroxy-
FDA 2018
R,S(+-)-Malic acid
Malicum acidum
Pomalous acid
DL-2-hydroxybutanedioic acid
d,l-malic acid
FEMA Number 2655
2-Hydroxyethane-1,2-dicarboxylic acid
Kyselina jablecna [Czech]
Malic acid [NF]
(+-)-Malic acid
Aepfelsaeure
FEMA No. 2655
CCRIS 2950
CCRIS 6567
(+/-)-Malic acid
EPA Pesticide Chemical Code 051101
HSDB 1202
Kyselina hydroxybutandiova
Kyselina hydroxybutandiova [Czech]
AI3-06292
H2mal
EINECS 210-514-9
EINECS 230-022-8
UNII-817L1N4CKP
NSC 25941
NSC-25941
817L1N4CKP
CHEBI:6650
INS NO.296
DTXSID0027640
E296
INS NO. 296
INS-296
Malic acid, L-
(+-)-Hydroxysuccinic acid
L-Malic acid-1-13C
MLS000084707
DTXCID107640
E-296
(+-)-1-Hydroxy-1,2-ethanedicarboxylic acid
Hydroxybutanedioic acid, (+-)-
dl-Hydroxybutanedioic acid
EC 210-514-9
EC 230-022-8
NSC25941
Malic acid (NF)
(+/-)-HYDROXYSUCCINIC ACID
DL-MALIC-2,3,3-D3 ACID
SMR000019054
DL-Apple Acid
HYDROXYBUTANEDIOIC ACID, (+/-)-
MALIC ACID (II)
MALIC ACID [II]
(R)-Hydroxybutanedioic acid
(S)-Hydroxybutanedioic acid
MALIC ACID (USP-RS)
MALIC ACID [USP-RS]
BUTANEDIOIC ACID, HYDROXY-, (S)-
R-Malic acid
MALIC ACID (EP MONOGRAPH)
MALIC ACID (USP IMPURITY)
MALIC ACID [EP MONOGRAPH]
MALIC ACID [USP IMPURITY]
Butanedioic acid, 2-hydroxy-, (2S)-
CAS-6915-15-7
L-(-)-MalicAcid
DL-hydroxysuccinic acid
C4H6O5
Hydroxybutanedioic acid, (-)-
MFCD00064213
(+/-)-2-Hydroxysuccinic acid
Racemic malic acid
180991-05-3
MFCD00064212
.+-.-Malic acid
Opera_ID_805
2-hydroxyl-succinic acid
DL-Malic acid, 99%
MALIC ACID [MI]
MALIC ACID,(DL)
2-Hydroxydicarboxylic acid
MALIC ACID [FCC]
SCHEMBL856
2-hydroxy-butanedioic acid
bmse000046
bmse000904
D03WNI
MALIC ACID [INCI]
MALIC ACID [VANDF]
Malic acid-, (L-form)-
DL-Malic acid, >=99%
HYOSCYAMINEHYDROBROMIDE
Oprea1_130558
Oprea1_624131
MALIC ACID [WHO-DD]
butanedioic acid, 2-hydroxy-
DL-HYDROXYSUCOINIC ACID
Butanedioic acid, (.+-.)-
DL(+/-)-MALIC ACID
GTPL2480
2-HYDROXY-SUCCINIC ACID
DL-HYROXYBUTANEDIOIC ACID
CHEMBL1455497
BDBM92495
DL-Malic acid, FCC, >=99%
HMS2358H06
HMS3371C13
(C4-H6-O5)x-
DL-Malic acid, analytical standard
HY-Y1311
STR03457
Tox21_201536
Tox21_300372
s9001
STL283959
HYDROXYBUTANEDIOIC ACID [HSDB]
AKOS000120085
AKOS017278471
(+/-)-HYDROXYBUTANEDIOIC ACID
AM81418
Butanedioic acid, hydroxy-, (.+.)-
CCG-266122
DB12751
LS-2394
DL-Malic acid, ReagentPlus(R), 99%
NCGC00043225-02
NCGC00043225-03
NCGC00254259-01
NCGC00259086-01
78644-42-5
DL-Malic acid, >=98% (capillary GC)
LS-88709
SY003313
SY009804
DL-Malic acid, ReagentPlus(R), >=99%
DL-Malic acid 1000 microg/mL in Methanol
DL-Malic acid, USP, 99.0-100.5%
CS-0017784
E 296
EU-0067046
FT-0605225
FT-0625484
FT-0625485
FT-0625539
FT-0632189
M0020
DL-Malic acid, SAJ first grade, >=99.0%
EN300-19229
A19426
C00711
C03668
D04843
DL-Malic acid, Vetec(TM) reagent grade, 98%
M-0825
AB00443952-12
Malic acid, meets USP/NF testing specifications
4-ethoxyphenyltrans-4-propylcyclohexanecarboxylate
L023999
Q190143
Q-201028
0C9A2DC0-FEA2-4864-B98B-0597CDD0AD06
F0918-0088
Z104473230
MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION)
Malic acid, United States Pharmacopeia (USP) Reference Standard
MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
Malic acid, Pharmaceutical Secondary Standard; Certified Reference Material
DL-Malic acid, meets analytical specification of FCC, E296, 99-100.5% (alkalimetric)
L-(−)-Malic acid
(-)-(S)-Malic acid
(-)-L-malic acid
(-)-Malic acid
(2S)-2-Hydroxybernsteinsäure [German] [ACD/IUPAC Name]
(2S)-2-hydroxybutanedioic acid
(2S)-2-Hydroxysuccinic acid [ACD/IUPAC Name]
(S)-(-)-2-Hydroxysuccinic acid
(S)-(−)-2-Hydroxysuccinic acid
(S)-(-)-Hydroxysuccinic acid
(S)-(-)-Malic acid
(S)-hydroxy-Butanedioic acid
(S)-Hydroxybutanedioic acid
(S)-Malate
(S)-malic acid
1723541 [Beilstein]
202-601-5 [EINECS]
97-67-6 [RN]
Acide (2S)-2-hydroxysuccinique [French] [ACD/IUPAC Name]
Butanedioic acid, 2-hydroxy-, (2S)- [ACD/Index Name]
Butanedioic acid, hydroxy-, (2S)-
L-(-)-Malic Acid
L-Hydroxybutanedioic acid
L-Hydroxysuccinic acid
l-malic acid
Malic acid, L-
MFCD00064213 [MDL number]
S-(-)-Malic acid
S-2-Hydroxybutanedioic acid
(-)-(S)-Malate
(-)-Hydroxysuccinate
(2S)-2-hydroxybutanedioate
(S)-(-)-Hydroxysuccinate
(S)-hydroxy-Butanedioate
(S)-Hydroxybutanedioate
L-Hydroxybutanedioate
L-Hydroxysuccinate
S-(-)-Malate
S-2-Hydroxybutanedioate
(-)-Hydroxysuccinic acid
(??)-Malic acid
(S)-(-)-Hydrosuccinic acid
(S)-2-hydroxysuccinic acid
[97-67-6] [RN]
210-514-9 [EINECS]
617-48-1 [RN]
6915-15-7 [RN]
99-98-9 [RN]
APPLE ACID
BUTANEDIOIC ACID, HYDROXY-, (S)-
D-malate
FLC
l-(-)-malic acid, ???
L-(-)-Malic acid|(2S)-2-Hydroxybutanedioic acid
l-(-)-malic acid-cp
L-2-Hydroxybutanedioic acid
laevo-malic acid
L-Apple acid
l-malicacid
LMR
M-0850
mal
MALATE ION
MALIC ACID, (L)
MLT
Oxaloacetate Ion
UNII:J3TZF807X5
UNII-817L1N4CKP
UNII-J3TZF807X5
pinguosuan
L-Mailcacid
L-malic acid
L(-)-Malic acid
l-(ii)-malicacid
L-(-)-Malic acid
L-(-)-Malic acid, CP
L-Hydroxysuccinic acid
L-Gydroxybutanedioicacid
(2S)-2-hydroxybutanedioate
(S)-(-)-Hydroxysuccinic acid
hydroxy-,(S)-Butanedioicacid
Butanedioicacid,hydroxy-,(S)-
(2S)-2-hydroxybutanedioic acid
Butanedioic acid, 2-hydroxy-, (2S)-