Encyclopedia / Acidity Regulators / Organic Intermediate / Pharmaceutical Intermediates

Malic acid

CAS：6915-15-7
MW:134.08744
MF：C4H6O5

Malic acid, HOOCCH(OH).CH2COOH, also known as hydroxysuccinic acid, is a colorless solid. It is soluble in water and alcohol. Malic acid exists in two optically active forms and a racemic mixture. It is used in medicine and found in apples and other fruits.The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Malic acid

1.2 Synonyms: (±)-1-Hydroxy-1,2-ethanedicarboxylic Acid; 2-Hydroxy-succinic acid; a-Hydroxysuccinic Acid; alpha-Hydroxysuccinic acid; alpha-hydroxysuccinicacid; Butanedioic acid, 2-hydroxy-; Butanedioic acid, hydroxy-; commonmalicacid; Deoxytetraric acid; deoxytetraricacid; DL(+/-)-MALIC ACID; DL-Hydroxybutanedioic acid; DL-MALIC ACID; EINECS 210-514-9; femanumber2655; Hydroxybutandisaeure; hydroxy-butanedioic acid; hydroxy-butanedioicaci; MALIC ACID, (DL); Malic acid, dl-; MFCD00064212; R,S(±)-Malic acid; R,S-Malic acid; UNII:817L1N4CKP;

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1.3 CAS No.: 6915-15-7

1.4 CID: 525

1.5 EINECS: 210-514-9

1.6 Molecular Formula: C4H6O5

1.7 Inchi: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

1.8 InChkey: BJEPYKJPYRNKOW-UHFFFAOYSA-N

1.9 Canonical Smiles: C(C(C(=O)O)O)C(=O)O

1.10 Isomers Smiles: C(C(C(=O)O)O)C(=O)O

2. Properties

2.1 Vapour pressure: 4.6 (vs air)

2.2 Solubility: methanol: 0.1?g/mL, clear, colorless

2.3 Viscosity: 6.5 mPa.s (= cP) 50% aqueous solution at 25 °C

2.4 VaporDensity: 4.6 (vs air)

2.5 Appearance: White to nearly white crystals or crystal powder

2.6 Storage: Ambient temperatures.

2.7 Chemical Properties: White to nearly white crystals or crystal powder

2.8 Color/Form: Powder

2.9 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.10 Heat of Combustion: -1.340 MJ/mol at 20 °C

2.11 Odor: Characteristic

2.12 PH: pH of a 0.001% aqueous solution is 3.80, that of 0.1% solution is 2.80, and that of a 1.0% solution is 2.34

2.13 pKa: 3.4(at 25℃)

2.14 Water Solubility: methanol: 0.1?g/mL, clear, colorless | 558 g/L (20 oC)

2.15 Stability: Stable under recommended storage conditions.

2.16 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.

3.2 Description: White to nearly white crystals or crystal powder White or nearly white, crystalline powder or granules having aslight odor and a strongly acidic taste. It is hygroscopic. Thesynthetic material produced commercially in Europe and the USA isa racemic mixture, whereas the naturally occurring material foundin apples and many other fruits and plants is levorotatory.

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3.3 Produe Method: Malic acid is manufactured by hydrating maleic and fumaric acidsin the presence of suitable catalysts. The malic acid formed is thenseparated from the equilibrium product mixture.

3.4 Purification Methods: Crystallise the acid from acetone, then from acetone/CCl4, or from ethyl acetate by adding pet ether (b 60-70o). Dry it at 35o under 1mm pressure to avoid formation of the anhydride. [Beilstein 3 IV 1124.]

3.5 Usage: Malic acid, HOOCCH(OH).CH2COOH, also known as hydroxysuccinic acid, is a colorless solid. It is soluble in water and alcohol. Malic acid exists in two optically active forms and a racemic mixture. It is used in medicine and found in apples and other fruits.The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece

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4. Safety and Handling

4.1 Exposure Standards and Regulations: Substance added directly to human food affirmed as generally recognized as safe (GRAS).
Malic acid used as a general purpose food additive in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

4.2 Octanol/Water Partition Coefficient: log Octanol/water partition coefficient: -1.26

4.3 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

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4.4 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.5 Safety Profile: A poison by intraperitoneal route. Moderately toxic by ingestion. A skin and severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

4.6 Formulations/Preparations: UVA URSI, THIS IS VOLATILE OIL CONTAINING A GLUCOSIDE, ARBUTIN, TANNIN, & GALLIC & MALIC ACIDS.
Grades: technical, active and inactive; FCC. The natural material is levorotatory, but the synthetic material is /optically/ inactive
Food grade: powder, fine granular, and granular
Granules and powder grades

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4.7 Incompatibilities: Malic acid can react with oxidizing materials. Aqueous solutionsare mildly corrosive to carbon steels.

4.8 Protective Equipment and Clothing: A skin and eye irritant

4.9 Skin, Eye, and Respiratory Irritations: A skin and eye irritant

4.10 Toxicity: LD50 orally in Rabbit: > 3200 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in D2O

1H NMR : 90 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Mass

7. Computed Properties

Molecular Weight：134.08744g/mol
Molecular Formula：C₄H₆O₅
Compound Is Canonicalized：True
XLogP3-AA：134.02152329
Monoisotopic Mass：134.02152329
Complexity：129
Rotatable Bond Count：3
Hydrogen Bond Donor Count：3
Hydrogen Bond Acceptor Count：5
Topological Polar Surface Area：94.8
Heavy Atom Count：：9
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：1
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYBgOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACBSggAIACAAAAgAIAACQCAIAAAAAAAAAAAFAAAABEBQAAAAAQAAFIAABAABDAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

8.Other Information

Usage: DL-Malic acid is used as a food additive. It is a component of some artificial vinegar flavors. Further, it is used in the preparation of chiral compounds, including κ-opioid rece. It is utilized for chiral resolution by ligand-exchange capillary electrophoresis.

Merck: 14,5707

BRN: 1723539

Chemical Properties: White to nearly white crystals or crystal powder

Chemical Properties: White or nearly white, crystalline powder or granules having a slight odor and a strongly acidic taste. It is hygroscopic. The synthetic material produced commercially in Europe and the USA is a racemic mixture, whereas the naturally occurring material found in apples and many other fruits and plants is levorotatory.

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Uses: Malic acid, HOOCCH(OH).CH2COOH, also known as hydroxysuccinic acid, is a colorless solid. It is soluble in water and alcohol. Malic acid exists in two optically active forms and a racemic mixture. It is used in medicine and found in apples and other fruits.
The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece

View all

Uses: malic acid is the third smallest alpha hydroxy acid in terms of molecular size. Although it is used in numerous cosmetic products, particularly those indicating a “fruit acid” content and generally designed for anti-aging, unlike glycolic and lactic acids, its skin benefits have not been extensively studied. Some formulators consider it difficult to work with, particularly when compared to other AHAs, and it can be somewhat irritating. It is rarely used as the only AHA in a product. It is found naturally occurring in apples.

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Uses: Malic Acid is an acidulant that is the predominant acid in apples. it exists as white crystalline powder or granules and is considered hygroscopic. as compared to citric acid, it is slightly less soluble but is still readily soluble in water with a solubility of 132 g/100 ml at 20°c. it has a stronger apparent acid taste and has a longer taste retention than citric acid which peaks faster but does not mask the aftertaste as effectively. a quantity of 0.362–0.408 kg of malic acid is equivalent to 0.453 kg of citric acid and to 0.272–0.317 kg of fumaric acid in tartness. at temperatures above 150°c it begins to lose water very slowly to yield fumaric acid. it is used in soft drinks, dry-mix beverages, puddings, jellies, and fruit filling. it is used in hard can- dies because it has a lower melting point (129°c) than citric acid which improves the ease of incorporation.

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Definition: ChEBI: A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.

Production Methods: Malic acid is manufactured by hydrating maleic and fumaric acids in the presence of suitable catalysts. The malic acid formed is then separated from the equilibrium product mixture.

Definition: A colorless crystalline carboxylic acid that is found in unripe fruits. It tastes of apples and is used in food flavorings.

Biotechnological Production: DL-malic acid as well as L-malic acid can be used in beverage, food, and animal nutrition. DL-malic acid is mainly derived from chemical synthesis, whereas L-malic acid is produced biotechnologically by enzymatic or fermentative processes.
Fumaric acid can be converted to L-malic acid using fumarases. Different microorganisms (e.g. Brevibacterium flavum, Brevibacterum ammoniagenes, and Corynebacterium species) are able to form naturally high amounts of fumarase intracellularly. For example, B. flavum has been immobilized in j-carrageenan and polyethyleneimine for whole-cell biocatalysis. A fumarase activity of 2.16 mmol.ml(gel)-1.h -1 at 55 C has been reported. This process has been used to produce 30 metric tons of L-malic acid per month in a continuous process with a 1,000 L column fed at a flow rate of 450 L.h-1 of 1 M sodium fumarate solution. Genetic engineering has been used to improve productivity, by which S. cerevisiae is modified to overexpress fumarase. With this method, a conversion rate of 65 mmol.g-1.h -1 has been observed.
Another possibility is the cultivation of an L-malic acid forming microorganism (e.g. Aspergillus flavus or Schizophyllum commune). The best results have been achieved by cultivation of A. flavus on glucose.Afinal product concentration of 113 g.L-1 with a yield of 1.26 mol of malic acid per mole of glucose and a productivity of 0.59 g.L-1.h-1 has been measured. Moreover, new biotechnological routes have been described using metabolically engineered S. cereviciae. In batch cultivations, concentrations up to 59 g.L-1 with a yield of 0.42 mol of malic acid per mole of glucose and a productivity of 0.19 g.L-1.h-1 have been observed.

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General Description: The chiral resolution of DL-malic acid by ligand-exchange capillary electrophoresis was studied.

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10. Related Questions

: What are the Various Applications and Quantification Methods of Malic Acid?General Description Malic acid, a key organic acid found in fruits and vegetables, plays essential roles in different industries. Its versatility is highlighted by its use as a food additive and in co..; What are the uses and safety considerations of malic acid in various industries?Description Malic acid (MA) is an organic compound also known as "apple acid" and "fruit acid," commonly found in many prepared foods. It occurs naturally in apples, particularly in the skin, and othe..; What is Malic Acid and How is it Prepared? Malic acid is a colorless, odorless, crystalline substance that is highly soluble in water, methanol, ethanol, acetone, ether, and other polar solvents. It is a dibasic acid with two dissociation con..; What are the benefits of malic acid for energy levels and skin health?As an organic compound, you can find Malic acid in things you regularly eat, such as apples. It is also found in wine and several other food sources. Is Malic acid natural? Yes, it occurs naturally in..

11. Realated Product Infomation