Citramalic acid, (+)-

HCID 441696
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Basic information

CAS
6236-09-5
Standard SMILES
C[C@](O)(CC(=O)O)C(=O)O
InChIKey
XFTRTWQBIOMVPK-YFKPBYRVSA-N
Molecular formula
C5H8O5
Average molar mass
148.11 g/mol
Monoisotopic mass
148.03717336

Overview

L-citramalic acid is the L-enantiomer of citramalic acid. It has a role as a plant metabolite. It is a conjugate acid of a L-citramalate(2-).

Names & identifiers

Preferred name
Citramalic acid, (+)-
IUPAC
(2S)-2-hydroxy-2-methylbutanedioic acid
English name
(S)-(+)-Citramalic acid
Molecular formula
C5H8O5
Molecular weight
148.11

Names & synonyms

(S)-2-Hydroxy-2-methylsuccinic acid6236-09-5(S)-(+)-Citramalic acidL-citramalic acid(+)-citramalic acid(S)-Citramalic acid(2S)-2-hydroxy-2-methylbutanedioic acidCitramalic acid, (+)-B3FC6PA80I(2S)-2-hydroxy-2-methylsuccinic acid(+)-METHYLMALIC ACIDCHEBI:29003
Show more names
2-HYDROXY-2-METHYLBUTANEDIOIC ACIDL-citramalicaci(S)-2-Methylmalate2-METHYLMALIC ACIDL-(+)-CITRAMALIC ACIDL-(+)-2-METHYLMALIC ACID(+)-2-Methyl-L-malic acid(S)-(+)-2-MethylmalicAcid
DTXSID901017263EINECS 228-350-1Butanedioic acid, 2-hydroxy-2-methyl-, (2S)-RefChem:577450DTXCID601475458228-350-1S-citramalic acid(S)-2-methylmalic acid

Database identifiers

CAS
6236-09-5
PubChem CID
441696
DTXSID
DTXSID901017263
ChEBI
CHEBI:29003
UNII
B3FC6PA80I
EC Number
228-350-1
Nikkaji
J73.969C

Properties

Computed structural properties

XLogP
-0.9
Topological polar surface area
94.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
10

Physicochemical properties

Melting point
109 · 109-111 °C(lit.)
Boiling point
188.68 °C · 188.68°C (rough estimate)
Density
1.2336 · 1.2336 (rough estimate)
refractive index
1.392 · 1.3920 (estimate)
solubility
Methanol (Slightly), Water (Slightly)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationButanedioic acid, 2-hydroxy-2-methyl-, (2S)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Hazard statements
H335-H319-H315

Chemistry & industry

Applications

Uses(+)-Citramalic Acid, is an analog of Malic Acid (M159510) that is produced from the condensation reaction of pyruvate and acetyl CoA catalyzed by (R)-citramalate synthase.

Suppliers11 total

北京华美互利生物化工010-56205725 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]

Additional notes

DefinitionChEBI: L-citramalic acid is the L-enantiomer of citramalic acid. It is a conjugate base of a L-citramalate(2-).

Related reactions

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Compound notes

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