(2Z)-2-methylbut-2-enedioic acid

• ChemBase ID: 4283
• Molecular Formular: C5H6O4
• Molecular Mass: 130.09874
• Monoisotopic Mass: 130.02660867
• SMILES: C/C(=C/C(=O)O)/C(=O)O
• Canonical SMILES: OC(=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-
• InChIKey: HNEGQIOMVPPMNR-IHWYPQMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-2-methylbut-2-enedioic acid
• IUPAC Traditional name: citraconic acid
• Synonyms: 2-Methyl-2-butenedioic acid; mesaconate; mesaconic acid; Methylfumaric acid; 2-methylfumarate; 2-Methylfumaric acid; METHYLMALEIC ACID; cis-Methylbutenedioic acid; Kyselina mesakonova [Czech]; trans-2-Methyl-2-butenedioic acid; Citraconate; (2E)-2-METHYLBUT-2-ENEDIOIC ACID; Citraconic acid; 2-Methylmaleic acid; Citraconic acid; 柠康酸

Database IDs

• CAS Number: 498-23-7
• EC Number: 207-858-7
• MDL Number: MFCD00078086
• Beilstein Number: 1722679
• Merck Index: 142321
• PubChem SID: 46505839; 160967715
• PubChem CID: 643798

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4984426
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.7134767
• LogD (pH = 7.4): -4.7702465
• Log P: 0.35463616
• Molar Refractivity: 28.9641 cm^3
• Polarizability: 10.915229 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.21
• LOG S: -0.91
• Solubility (Water): 1.59e+01 g/l

PROPERTIES

Physical Property

• Melting Point: 88-91°C
• Density: 1.620

Safety Information

• Storage Warning: Hygroscopic; IRRITANT
• RTECS: GE6650000
• European Hazard Symbols: X
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS06
• GHS Hazard statements: H301
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A

Product Information

• Purity: 98%; 98+%

DETAILS

DrugBank - DB04734

• Drug Groups: experimental
• Description: Citraconic acid is one of the isomeric dicarboxylic acids produced by the distillation of citric acid, or as metabolites by microorganisms, cis-CH3-C(CO2H)=CHCO2H; the trans-isomer is mesaconic acid.