Citraconic acid

Citraconic acid: Citraconic acid

IUPAC name

(2Z)-2-Methylbut-2-enedioic acid

Other names

Citraconate; Methylmaleic acid; cis-Methylbutenedioic acid

Identifiers

CAS number 498-23-7^Y

PubChem 643798

ChemSpider 553689^Y

DrugBank DB04734

ChEBI CHEBI:17626^Y

Jmol-3D images Image 1

SMILES

O=C(O)\C=C(/C(=O)O)C

InChI

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-^Y
Key: HNEGQIOMVPPMNR-IHWYPQMZSA-N^Y

Properties

Molecular formula C₅H₆O₄

Molar mass 130.1 g mol⁻¹

Appearance Monoclinic crystals^[1]

Density 1.62 g/cm3^[1]

Melting point
~90 °C (decomposition)^[1]

Solubility in water Freely soluble^[1]

Hazards

R-phrases R22^[2]

S-phrases S36^[2]

Y acid (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Citraconic acid is one of the pyrocitric acids formed upon the heating of citric acid.^[1] It is the cis-isomer of mesaconic acid.

References

^ ^a ^b ^c ^d ^e Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123

^ ^a ^b Citraconic acid

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Academic Dictionaries and Encyclopedias

Citraconic acid

IUPAC name (2Z)-2-Methylbut-2-enedioic acid
Other names Citraconate; Methylmaleic acid; cis-Methylbutenedioic acid
Identifiers
CAS number	498-23-7^Y
PubChem	643798
ChemSpider	553689^Y
DrugBank	DB04734
ChEBI	CHEBI:17626^Y
Jmol-3D images	Image 1
SMILES O=C(O)\C=C(/C(=O)O)C
InChI InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-^Y Key: HNEGQIOMVPPMNR-IHWYPQMZSA-N^Y
Properties
Molecular formula	C₅H₆O₄
Molar mass	130.1 g mol⁻¹
Appearance	Monoclinic crystals^[1]
Density	1.62 g/cm3^[1]
Melting point	~90 °C (decomposition)^[1]
Solubility in water	Freely soluble^[1]
Hazards
R-phrases	R22^[2]
S-phrases	S36^[2]
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references