2-methylidenebutanedioic acid

• ChemBase ID: 102550
• Molecular Formular: C5H6O4
• Molecular Mass: 130.09874
• Monoisotopic Mass: 130.02660867
• SMILES: OC(=O)CC(=C)C(=O)O
• Canonical SMILES: OC(=O)CC(=C)C(=O)O
• InChI: InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
• InChIKey: LVHBHZANLOWSRM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methylidenebutanedioic acid
• IUPAC Traditional name: itaconic acid
• Synonyms: 3-Carboxy-3-butenoic acid; Methylenesuccinic acid; ITACONIC ACID; 2-methylenesuccinic acid; Itaconic acid; Methylenebutanedioic acid; 亚甲基琥珀酸; 衣康酸

Database IDs

• CAS Number: 97-65-4
• EC Number: 202-599-6
• MDL Number: MFCD00004260
• Beilstein Number: 1759501
• Merck Index: 145242
• PubChem SID: 162089924; 24881763; 24896018
• PubChem CID: 811
• CHEBI ID: 30838
• CHEMBL: 359159
• Chemspider ID: 789
• KEGG ID: C00490
• Wikipedia Title: Itaconic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.6521044
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.8351188
• LogD (pH = 7.4): -6.119271
• Log P: 0.052824683
• Molar Refractivity: 27.9149 cm^3
• Polarizability: 10.915229 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 g/12 mL in water; 1 g/5 mL in ethanol
• Apperance: White crystals
• Melting Point: 162 - 164 °C with decomposition; 162 - 164°C (decomp.); 165-167 °C; 165-168 °C(lit.); 165-169°C
• Boiling Point: 268 °C with decomposition; 268°C
• Auto Ignition Point: 1472 °F
• Density: 1.573 g/mL at 25 °C(lit.); 1.63 g/cm^3; 1.630; 1.632 g/cm^3 at 20 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-36; 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99%; ≥99.0% (T); 99%
• Grade: puriss.
• Ignition Residue: ≤0.05%
• Linear Formula: HO2CCH2C(=CH2)CO2H
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05214066

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102107

Crystalline
Purity: 99+%

Sigma Aldrich - I29204

Packaging
1 kg in poly bottle
100 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. I29204.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.