Encyclopedia / Herbal Extract / Food Additives / Pharmaceutical Intermediates

L-(-)-Malic Acid

CAS：97-67-6
MW:134.09
MF：C4H6O5

Active ingredient in many sour or tart foods.

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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: L-(-)-Malic Acid

1.2 Synonyms: (±)-1-Hydroxy-1,2-ethanedicarboxylic Acid; (±)-Malic Acid; (S)-2-hydroxysuccinic acid; 2-Hydroxy-succinic acid; a-Hydroxysuccinic Acid; alpha-Hydroxysuccinic acid; alpha-hydroxysuccinicacid; Butanedioic acid, 2-hydroxy-; Butanedioic acid, 2-hydroxy-, (2S)-; Butanedioic acid, hydroxy-; Butanedioicacid,hydroxy-,(S)-; DL(+/-)-MALIC ACID; DL-Hydroxybutanedioic acid; DL-MALIC ACID; EINECS 202-601-5; hydroxy-,(S)-Butanedioicacid; Hydroxybutandisaeure; hydroxy-butanedioic acid; L(-)-Malic Acid; L-(-)-Malic acid, CP; l-(ii)-malicacid; L-Gydroxybutanedioicacid; L-Mailcacid; L-Malic acid; Malic acid; MALIC ACID, (DL); Malic acid, dl-; MFCD00064213; pinguosuan; R,S(±)-Malic acid; R,S-Malic acid; UNII:817L1N4CKP;

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1.3 CAS No.: 97-67-6

1.4 CID: 222656

1.5 EINECS: 202-601-5

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)/t2-/m0/s1

1.8 InChkey: BJEPYKJPYRNKOW-REOHCLBHSA-N

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

1.10 Isomers Smiles: C([C@@H](C(=O)O)O)C(=O)O

2. Properties

2.1 Solubility: H2O: 0.5?M at?20?°C, clear, colorless

2.2 Appearance: White Powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: L-Malic acid is nearly odorless (sometimes a faint, acrid odor). This compound has a tart, acidic, nonpungent taste.

2.5 Color/Form: White

2.6 PH: 2.2 (10g/l, H2O, 20℃)

2.7 pKa: (1) 3.46, (2) 5.10(at 25℃)

2.8 Water Solubility: H2O: 0.5?M at?20?°C, clear, colorless

2.9 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.10 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: An optically active form of malic acid having (S)-configuration.

3.2 Description

L-Malic acid is nearly odorless (sometimes a faint, acrid odor). This compound has a tart, acidic, nonpungent taste. clear colourless solution

OtherSolid|Solid|white crystalline powder, granules, or needles; acid taste; odourless or having a very faint caramellic acrid odour and a tart aciduous taste

(S)-malic acid is an optically active form of malic acid having (S)-configuration. It is a conjugate acid of a (S)-malate(2-). It is an enantiomer of a (R)-malic acid.

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3.3 Methods of Manufacturing: Malic acid exists widely in nature, is the product of animal and plant metabolism, and is the main acid component in apples.?Boil the juice of unripe apples, grapes and peaches, add lime water to form calcium salt precipitate, and then convert it to lead salt, and then generate free acid by treatment to obtain L-malic acid.?The fermentation method is also possible to achieve industrialization. Fermentation using mutated yeasts can obtain special bacteria based on L-malic acid for acidification, or special bacteria based on production of malic acid for fermentation. L-malic acid, but the process is more complicated than the synthesis method, and the cost is higher.?Japan uses biosynthesis to produce L-malic acid.?First, Bredacterium ammoni-agenes cells were fixed with polyacrylamide.?The suspension of cells in physiological saline is mixed with acrylic amide, an appropriate cross-linking agent and a polymerization accelerator, and the resulting gel is made into particles with a diameter of 3 mm.?After washing, it was soaked in sodium fumarate containing about 0.3 bovine bile, and the solution was kept at 37°C for 20 hours.?The treated cells are used as the packing of the reaction column.?1L containing 1mol of sodium fumarate passes through the reaction column at 37°C, and malic acid is separated from the effluent by the usual method, and L-malic acid pharmaceutical grade product is produced from fumaric acid with a yield of about 70% .

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3.4 Purification Methods: Crystallise S-malic acid (charcoal) from ethyl acetate/pet ether (b 55-56o), keeping the temperature below 65o. Or dissolve it by refluxing in fifteen parts of anhydrous diethyl ether, decant, concentrate to one-third volume and crystallise it at 0o, repeatedly to constant melting point. [Beilstein 3 IV 1123.] L-(-)-Malic Acid Preparation Products And Raw materials Raw materials

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3.5 Usage: Active ingredient in many sour or tart foods.

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 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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4.6 Protective Equipment and Clothing: A skin and eye irritant

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

4.8 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: ON7175000
HS Code: 29181980

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4.9 Specification: Storage
It should be stored in a tightly closed container and keep container closed when not in use. It should be stored in a cool and dry area away from incompatible substances.
Handling
Wash thoroughly after handling.Avoid contact with eyes, skin, and clothing. Remove contaminated clothing and wash before reuse. Wash clothing before reuse. Avoid ingestion and inhalation. Use with adequate ventilation.
Personal Protection
Wear appropriate protective chemical safety goggles or eyeglasses. Wear appropriate protective gloves to prevent skin exposure.Wear suitable protective clothing to prevent skin exposure.
Small spills/leaks
Clean up spills right away, using the suitable protective equipment. Sweep up, then place into a container for disposal. Avoid generating dusty conditions. Provide ventilation.

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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

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

1H NMR : 90 MHz in D2O

1H NMR : Predict

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

97-67-6Total: 65 Synthesis Route

68-04-2 308 Suppliers

97-67-6 339 Suppliers

64-17-5 396 Suppliers

97-67-6 339 Suppliers

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8. Precursor and Product

precursor:

64-17-5

68-04-2

56-84-8

110-17-8

50-99-7

70-47-3

57-50-1

584-98-5

product:

3972-40-5

52079-23-9

5469-16-9

691-84-9

87-69-4

77-92-9

923-06-8

328-42-7

617-55-0

59025-03-5

9. Computed Properties

Molecular Weight：134.09g/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：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYBgOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACBSggAIACAAAAgAIAACQCAIAAAAAAAAAAAFAAAABEBQAAAAAQAAFIAABAABDAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: L-(-)-Malic acid is used as Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece. It also acts as active ingredient in many sour or tart foods. It is used as synthesizing disincrustant and fluorescent whitening agent. It aids in the production of polyester and alcohol acid resins.

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Usage: 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.

Merck: 14,5707

BRN: 1723541

Description: ι-Malic acid is nearly odorless (sometimes a faint, acrid odor) with a tart, acidic taste. It is nonpungent. May be prepared by hydration of maleic acid; by fermentation from sugars.

Chemical Properties: L-Malic acid is nearly odorless (sometimes a faint, acrid odor). This compound has a tart, acidic, nonpungent taste.

Chemical Properties: clear colourless solution

Occurrence: Occurs in maple sap, apple, melon, papaya, beer, grape wine, cocoa, sake, kiwifruit and chicory root.

Uses: 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.

Uses: 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

Uses: Intermediate in chemical synthesis. Chelating and buffering agent. Flavoring agent, flavor enhancer and acidulant in foods.

Definition: ChEBI: An optically active form of malic acid having (S)-configuration.

Preparation: By hydration of maleic acid; by fermentation from sugars.

General Description: L-(-)-Malic acid is an organic acid that is commonly found in wine. It plays an important role in wine microbiological stability.

Storage Conditions: Malic acid exists widely in nature, is the product of animal and plant metabolism, and is the main acid component in apples.?Boil the juice of unripe apples, grapes and peaches, add lime water to form calcium salt precipitate, and then convert it to lead salt, and then generate free acid by treatment to obtain L-malic acid.?The fermentation method is also possible to achieve industrialization. Fermentation using mutated yeasts can obtain special bacteria based on L-malic acid for acidification, or special bacteria based on production of malic acid for fermentation. L-malic acid, but the process is more complicated than the synthesis method, and the cost is higher.?Japan uses biosynthesis to produce L-malic acid.?First, Bredacterium ammoni-agenes cells were fixed with polyacrylamide.?The suspension of cells in physiological saline is mixed with acrylic amide, an appropriate cross-linking agent and a polymerization accelerator, and the resulting gel is made into particles with a diameter of 3 mm.?After washing, it was soaked in sodium fumarate containing about 0.3 bovine bile, and the solution was kept at 37°C for 20 hours.?The treated cells are used as the packing of the reaction column.?1L containing 1mol of sodium fumarate passes through the reaction column at 37°C, and malic acid is separated from the effluent by the usual method, and L-malic acid pharmaceutical grade product is produced from fumaric acid with a yield of about 70% .

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Collision Cross Section: 118.8 ?2 [M-H]- [CCS Type: DT, Method: stepped-field]|116.3 ?2 [M-H]-

Production: 25,000 - 100,000 lb

Manufacturing Info: Butanedioic acid, 2-hydroxy-, (2S)-: ACTIVE

Use Classification: Food additives -> Flavoring Agents|Cosmetics -> Buffering

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12. Related Questions

: What Are the Characteristics and Applications of L-Malic Acid?Introduction L-Malic acid, a dicarboxylic acid with the chemical formula C4H6O5, is essential in various industries due to its versatile properties and wide-ranging applications. Found naturally in fr..; What are the applications and benefits of L-(-)-Malic Acid?L-(-)-Malic Acid is widely used as a functional acidulant in the beverage and food industry. Its tartness is long-lasting and 20% stronger than citric acid. It not only preserves the flavor of natural..; What are the benefits of L-malic acid and its applications? L-malic acid, a natural organic acid with a taste similar to that of natural apple, is widely found in plant, animal, and microbial cells. It has been recognized as a safe and edible organic acid by ..; What is the new extraction process of L-(-)-Malic Acid?Background technologyMalic acid, also known as 2-hydroxysuccinic acid, has an asymmetric carbon atom in the molecule, including L-malic acid, D-malic acid and D L-(- )-Malic Acid 3 isomers. Naturally ..

13. Realated Product Infomation