1-(2H-1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

• ChemBase ID: 154586
• Molecular Formular: C14H18O3
• Molecular Mass: 234.29092
• Monoisotopic Mass: 234.12559444
• SMILES: CC(C)(C)C(/C=C/c1ccc2c(c1)OCO2)O
• Canonical SMILES: OC(C(C)(C)C)/C=C/c1ccc2c(c1)OCO2
• InChI: InChI=1S/C14H18O3/c1-14(2,3)13(15)7-5-10-4-6-11-12(8-10)17-9-16-11/h4-8,13,15H,9H2,1-3H3
• InChIKey: IBLNKMRFIPWSOY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2H-1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol; (1E)-1-(2H-1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
• IUPAC Traditional name: 1-(2H-1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol; stiripentol
• Synonyms: 4,4-dimethyl-1-[3,4(methylenedioxy)-phenyl]-1-penten-3-ol; Diacomit; Stiripentol; 1-(1,3-Benzodioxol-5yl)-4,4-dimethyl-1-penten-3-ol; 4,4-Dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-ol; BCX 2600; Stiripentol

Database IDs

• CAS Number: 49763-96-4
• EC Number: 256-480-9
• MDL Number: MFCD00869310
• PubChem SID: 162248724
• PubChem CID: 5311454

CALCULATED PROPERTIES

• Acid pKa: 14.337275
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1211164
• LogD (pH = 7.4): 3.1211162
• Log P: 3.1211164
• Molar Refractivity: 66.7719 cm^3
• Polarizability: 26.129786 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO: ≥20 mg/mL; Ethyl Acetate; Methanol
• Apperance: White Solid; white to beige powder
• Melting Point: 73-74°C

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H18O3

DETAILS

Sigma Aldrich - S6826

Biochem/physiol Actions
Anti-convulsant drug

Toronto Research Chemicals - S686825

An epilepsy drug. It has been used as co-therapy for treatment of epilepsy. It inhibits the enzymes responsible for metabolism of other anti-convulsant agents.

REFERENCES

• Laurie, D., et al.: J. Neurosci., 12, 4151 (1992)
• Smith, A., et al.: J. Pharmacol. Exp. Therap., 311, 601 (1992)
• Trojnar, M., et al.: Pharm. Rep., 57, 154 (1992)
• Drafts, B., et al.: J. Pharm. Exp. Ther., 318, 1094 (1992)
• Picton, A., et al.: Brain Res.