4-hydroxybut-2-enoic acid

• ChemBase ID: 129685
• Molecular Formular: C4H6O3
• Molecular Mass: 102.08864
• Monoisotopic Mass: 102.03169405
• SMILES: O=C(O)/C=C/CO
• Canonical SMILES: OC/C=C/C(=O)O
• InChI: InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h1-2,5H,3H2,(H,6,7)
• InChIKey: RMQJECWPWQIIPW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxybut-2-enoic acid; (2E)-4-hydroxybut-2-enoic acid
• IUPAC Traditional name: 4-hydroxy-2-butenoic acid; 4-hydroxycrotonic acid
• Synonyms: ''trans''-4-hydroxycrotonic acid; T-HCA; trans-4-Hydroxycrotonic Acid; trans-γ-Hydroxycrotonic Acid; (E)-4-Hydroxycrotonic Acid

Database IDs

• CAS Number: 24587-49-3
• PubChem SID: 162223974
• PubChem CID: 6155526
• CHEMBL: 507046
• Chemspider ID: 4825947
• Wikipedia Title: T-HCA

CALCULATED PROPERTIES

• Acid pKa: 4.4451327
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.451284
• LogD (pH = 7.4): -3.2139952
• Log P: -0.36118886
• Molar Refractivity: 24.7396 cm^3
• Polarizability: 9.090525 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H925000

γ-Hydroxybutyric acid (GHB) analog.

REFERENCES

• Castelli, M., et al.: J. Neurochem., 87, 722 (2003)
• Wellendorph, P., et al.: J. Pharmacol. Exp. Ther., 315, 346 (2003)