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
Show more names
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
- Formal charge
- 0
- Complexity
- 129
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)
- vapor pressure
- 0.1 mm · <0.1 mm Hg ( 20 °C)
- refractive index
- 1.392 · 1.3920 (estimate)
- FLAVIS Number
- 8.017 · 08.017 | l-Malic acid
- Flash point
- 203 °C · 203 °C
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 g/mL, · methanol: 0.1 g/mL, clear, colorless
- pka
- 3.4 · 3.4(at 25℃)
- form
- Solid
- color
- White to Almost white
- Odor
- 100 % · at 100.00 %. odorless
- PH
- 3.33 · 3.33(1 mM solution);2.74(10 mM solution);2.21(100 mM solution);
- Odor Type
- odorless
- biological source
- synthetic
- optical activity
- 0.1 to · [α]/D 0.10 to +0.10°
- Water Solubility
- 558 g/L · 558 g/L (20 ºC)
- Merck
- 14 · 14,5707
- BRN
- 1723539 · 1723539
- Henry's Law Constant
- 2.7 · 2.7×108 mol/(m3Pa) at 25℃, Compernolle and Müller (2014)
- Major Application
- pharmaceutical (small molecule)
- Cosmetic Ingredient Review (CIR)
- Malic acid (6915-15-7)
- InChI
- 1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
- InChIKey
- BJEPYKJPYRNKOW-UHFFFAOYSA-N
- SMILES
- OC(CC(O)=O)C(O)=O
- LogP
- -6.14 at · -6.14 at 20℃
- CAS DataBase Reference
- 6915 · 6915-15-7(CAS DataBase Reference)
- FDA 21 CFR
- 184.1069 · 184.1069; 582.1069
- SCOGS (Select Committee on GRAS Substances)
- Malic acid
- EWG's Food Scores
- 1 · 1-4
- FDA UNII
- 817 L1N4CKP · 817L1N4CKP
- NIST Chemistry Reference
- Hydroxybutanedioic acid(6915-15-7)
- EPA Substance Registry System
- Malic acid (6915-15-7)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-37/38-41-36/37/38-42/43-34
- Safety Statements
- 26 · 26-39-37/39-36-36/39
- WGK Germany
- 1 · 1
- RTECS
- 7175000 · ON7175000
- Autoignition Temperature
- 644 °F · 644 °F
- TSCA
- TSCA listed
- HS Code
- 29181980 · 29181980
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- Hazardous Substances Data
- 6915 · 6915-15-7(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 3200 mg/kg
- REACH Registrations
- Active
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
- risk_code
- 22-37/38-41-36/37/38-42/43-34
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-39-37/39-36-36/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Autoignition Temperature
- 644 °F
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
- Hazardous Substances Data
- 6915-15-7(Hazardous Substances Data)
Chemistry & industry
Applications
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
Downstream products
Suppliers50 total
Additional notes
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
Linked notes
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