2-(2-methylidenecyclopropyl)acetic acid

• ChemBase ID: 157553
• Molecular Formular: C6H8O2
• Molecular Mass: 112.12652
• Monoisotopic Mass: 112.0524295
• SMILES: C=C1CC1CC(=O)O
• Canonical SMILES: OC(=O)CC1CC1=C
• InChI: InChI=1S/C6H8O2/c1-4-2-5(4)3-6(7)8/h5H,1-3H2,(H,7,8)
• InChIKey: QJBXAEKEXKLLLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-methylidenecyclopropyl)acetic acid
• IUPAC Traditional name: (2-methylidenecyclopropyl)acetic acid
• Synonyms: (RS)-(Methylenecyclopropyl)acetic acid

Database IDs

• CAS Number: 1073-00-3
• MDL Number: MFCD11558999
• Beilstein Number: 1927126
• PubChem SID: 162251690
• PubChem CID: 10214381

CALCULATED PROPERTIES

• Acid pKa: 4.65723
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.21573602
• LogD (pH = 7.4): -1.9933933
• Log P: 0.6844253
• Molar Refractivity: 28.9441 cm^3
• Polarizability: 11.343062 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-38
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C6H8O2

DETAILS

Sigma Aldrich - 63978

Application
Hypoglycin A is metabolized by means of transamination and oxidative decarboxylation to methylene cyclopropyl acetic acid (MCPA). MCPA forms nonmetabolizable carnitine and coenzyme A (CoA) esters, thereby depressing tissue levels of these cofactors and making them less available for other biochemical reactions.