2-methylbut-2-enedioic acid

• ChemBase ID: 103125
• 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)
• InChIKey: HNEGQIOMVPPMNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methylbut-2-enedioic acid
• IUPAC Traditional name: 2-methyl-2-butenedioic acid
• Synonyms: Citraconate; cis-Methylbutenedioic acid; MESACONIC ACID; Citraconic acid; Methylmaleic acid; CITRACONIC ACID; Methylfumaric acid; Mesaconic acid; 甲基马来酸; 柠康酸; 甲基富马酸; 中康酸

Database IDs

• CAS Number: 498-23-7; 498-24-8
• EC Number: 207-859-2; 207-858-7
• MDL Number: MFCD00078086; MFCD00002653
• Beilstein Number: 1722679; 1722680
• PubChem SID: 162102999; 24893036; 24856571; 24882979; 24847989
• PubChem CID: 643798; 638129
• CHEBI ID: 17626
• Chemspider ID: 553689
• DrugBank ID: DB04734
• Wikipedia Title: Mesaconic_acid; Citraconic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.7223003
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.3959503
• LogD (pH = 7.4): -5.7258286
• 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

PROPERTIES

Physical Property

• Solubility: Freely soluble in water
• Apperance: Monoclinic crystals
• Melting Point: ~90 °C (decomposition); 200-202 °C(lit.); 202-204 °C; 204-205 °C; 88-94 °C(lit.); 88-94°C; 91-95 °C
• Boiling Point: 250 °C (decomp.)
• Density: 1.31 g/cm^3; 1.62 g/cm3

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• RTECS: GE6650000; OX5075000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38; R:22; R22
• Safety Statements: 26-36; 36; S:36/37/39; S36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0% (T); 98%; 99%
• Grade: purum
• Ignition Residue: ≤0.1%
• Linear Formula: CH3C(CO2H)=CHCO2H; HOOCCH=C(CH3)COOH

DETAILS

MP Biomedicals - 05202144

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150694

Purity: 99+%

Sigma Aldrich - C82604

Packaging
100 g in poly bottle
5 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C82604.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C82604.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 131040

Packaging
10, 50 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 131040.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.