Basic information
- CAS
636-61-3- Standard SMILES
O=C(O)C[C@@H](O)C(=O)O- InChIKey
BJEPYKJPYRNKOW-UWTATZPHSA-N- Molecular formula
- C4H6O5
- Average molar mass
- 134.09 g/mol
- Monoisotopic mass
- 134.02152329
Names & identifiers
- Preferred name
- D-Malic acid
- IUPAC
- (2R)-2-hydroxybutanedioic acid
- English name
- D(+)-Malic acid
- Molecular formula
- C4H6O5
- Molecular weight
- 134.09
Names & synonyms
D-(+)-malic acidD-malic acid(R)-malic acidMalic acid, D-Malic acid D-(+)-form(+)-D-malic acidL(+)-Malic acidButanedioic acid, hydroxy-, (2R)-(R)-2-hydroxybutanedioic acid(r)-(+)-hydroxysuccinic acidMalic acid, L(+)-EINECS 211-262-2
Show more names
(2R)-2-Hydroxybutanedioic acid(R)-HYDROXYSUCCINIC ACIDD-(+)-MaLD(+)-MalicD-APPLE ACID(R)-malicacil(+)-malicaci
CHEBI:30796P750Y95K96MALIC ACID D-(+)-FORM [MI]BUTANEDIOIC ACID, 2-HYDROXY-, (2R)-2-HYDROXY-SUCCINIC ACIDDMalic acidMalic acid, DMalic acid D(+)form
Database identifiers
- CAS
636-61-3- PubChem CID
- 92824
- DTXSID
DTXSID90892496- ChEMBL
CHEMBL225986- ChEBI
CHEBI:30796- UNII
- P750Y95K96
- EC Number
- 211-262-2
- Nikkaji
- J14.674I
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
Experimental & physicochemical properties
LogP-1.26
Solubility364 mg/mL at 20 °C
Melting Point101 °C
Physical Description
Solid; [Merck Index] White powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
120.68 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
116.3 Ų [M-H]-
Physicochemical properties
- Melting point
- 98 · 98-102 °C (lit.)
- alpha
- 2.2 · 2.2 º (c=3, H2O)
- Boiling point
- 167.16 °C · 167.16°C (rough estimate)
- Density
- 1.6 · 1.60
- bulk density
- 600 kg/m3 · 600kg/m3
- refractive index
- 6.5 ° · 6.5 ° (C=10, Acetone)
- storage temp.
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.1% (3 of 98) of reports.
Danger
H315 (93.9%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (91.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H335 (92.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 98 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 3 of 98 reports by companies.；There are 12 notifications provided by 95 of 98 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Status: Active Update: 14-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/30537
D-(+)-Malic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant that may cause serious eye injury; [Alfa Aesar MSDS] See Malic acid.
Hazard Classes and CategoriesSkin Irrit. 2 (93.9%)；Eye Dam. 1 (91.8%)；STOT SE 3 (92.9%)
Regulatory information
Regulatory Information
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm；Extracellular
Uses & manufacturing
UsesUsed as an intermediate, chelating agent, buffering agent, and food additive; [Merck Index]
Applications
UsesThe 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
UsesD-(+)-Malic acid used as an acidulant and flavoring agent, food additive. And it is also used in the place of the less sour citric acid in sour sweets.
UsesD-(+)-Malic acid can be used: As a starting material for the enantioselective total synthesis of ()-erinapyrone B.As a chiral organocatalyst in the synthesis of α-aminophosphonates from various aldehydes, aniline, and diethyl phosphite.
Upstream & downstream products
Upstream raw materials
Related reactions
18 records
Compound notes
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