2-methylpropanedioic acid

• ChemBase ID: 3800
• Molecular Formular: C4H6O4
• Molecular Mass: 118.08804
• Monoisotopic Mass: 118.02660867
• SMILES: CC(C(=O)O)C(=O)O
• Canonical SMILES: CC(C(=O)O)C(=O)O
• InChI: InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
• InChIKey: ZIYVHBGGAOATLY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methylpropanedioic acid
• IUPAC Traditional name: methylmalonic acid
• Synonyms: Methylmalonic acid; 2-methylmalonic acid; Methylpropanedioic Acid; 1,1-Ethanedicarboxylic Acid; Isosuccinic Acid; NSC 25201; Methylmalonic Acid; 2-Methylpropanedioic acid; 甲基马来酸; 甲基丙二酸

Database IDs

• CAS Number: 516-05-2
• EC Number: 208-219-5
• MDL Number: MFCD00002656
• Beilstein Number: 1756084
• PubChem SID: 46506625; 24896996; 24885379; 160967237
• PubChem CID: 487
• CHEBI ID: 30860
• MeSH Name: Methylmalonic+acid
• Wikipedia Title: Methylmalonic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4752705
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.7650728
• LogD (pH = 7.4): -4.472135
• Log P: 0.21186902
• Molar Refractivity: 23.5623 cm^3
• Polarizability: 9.383458 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.17
• LOG S: 0.1
• Solubility (Water): 1.49e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 128-130 °C(lit.); 131-134 °C; 134-136°C
• Density: 1.455 g/ml

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: OO1400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 97%; 99%
• Grade: purum
• Linear Formula: CH3CH(CO2H)2

DETAILS

MP Biomedicals - 02151661

Crystalline
Increased urinary excretion of this compound occurs in cyanocobalamin deficiency

MP Biomedicals - 05203516

MP Biomedicals Rare Chemical collection

DrugBank - DB04183

• Drug Groups: experimental
• Description: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. [PubChem]

Sigma Aldrich - M54058

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - M318860

Binds with coenzyme A to form methylmalonyl-CoA, also a metabolic intermediate transformed to succinic acid (SA) by a vitamin B12-dependent catalytic step, and is broadly used as a clinical biomarker of functional vitamin B12 status.

REFERENCES

• Pedersen, T., et al.: J. Chromatogr., B: Anal. Technol. Biomed. Life Sci., 879, 1502 (2011)