L-Malic Acid

HCID 222656CAS 6915-15-7

Basic information

Standard SMILES
O=C(O)C[C@H](O)C(=O)O
InChIKey
BJEPYKJPYRNKOW-REOHCLBHSA-N
Molecular formula
C4H6O5
Average molar mass
134.09 g/mol
Monoisotopic mass
134.02152329

Names & identifiers

Preferred name
L-Malic Acid
IUPAC
(2S)-2-hydroxybutanedioic acid
English name
Malic acid
Molecular formula
C4H6O5
Molecular weight
134.09

Names & synonyms

L-Malic acid(2S)-2-Hydroxybutanedioic acid(-)-Malic acid(-)-Hydroxysuccinic acidS-(-)-Malic acidMalic acid, L-Malic acid L-(-)-formHydroxysuccinnic acid (-)Butanedioic acid, 2-hydroxy-, (2S)-Hydroxybutanedioic acid, (S)-J3TZF807X5NSC9232
Show more names
malicDL-Malic2-hydroxybutanedioic acid-MaLE 296DL-MALATEPomalus acidDeoxytetraric acidMALIC ACID, DL-(P)hydroxy-butanedioicaci
2-Hydroxybutanedioic acid, (S)-NSC 9232EINECS 202-601-5L-MALIC ACID [FHFI]L-MALIC ACID [WHO-DD]DTXSID30273987MALIC ACID L-(-)-FORM [MI]MALIC ACID, L-(II)

Database identifiers

CAS
6915-15-7、97-67-6
PubChem CID
222656
DTXSID
DTXSID30273987
ChEMBL
CHEMBL1234046
ChEBI
CHEBI:30797
UNII
J3TZF807X5
EC Number
202-601-5
Nikkaji
J74.430A

Properties

Computed structural properties

XLogP
-1.3
Topological polar surface area
94.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
9

Physicochemical properties

Melting point
131 · 131-133 °C (lit.)
Boiling point
167.16 °C · 167.16°C (rough estimate)
alpha
20 · [α]D20 -0.5~+0.5° (c=5, H2O)
bulk density
800 kg/m3 · 800kg/m3
Density
1.609 · 1.609
vapor density
4.6 · 4.6 (vs air)

Safety & regulation

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
ON7175000
hs_code
29181980
Toxicity
LD50 orally in Rabbit: > 3200 mg/kg

Chemistry & industry

Applications · 4 items

UsesMalic 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.

UsesMalic 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

Usesmalic 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.

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

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东艾斯曼新材料有限公司13698626386 13698626386
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Malic acid is a 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group. It has a role as a food acidity regulator and a fundamental metabolite. It is a 2-hydroxydicarboxylic acid and a C4-dicarboxylic acid. It derives from a succinic acid. It is a conjugate acid of a malate(2-) and a malate.

Related reactions

125 records

Linked notes

Loading…