4-(prop-2-en-1-yl)benzene-1,2-diol

• ChemBase ID: 119197
• Molecular Formular: C9H10O2
• Molecular Mass: 150.1745
• Monoisotopic Mass: 150.06807956
• SMILES: c1(c(ccc(c1)CC=C)O)O
• Canonical SMILES: C=CCc1ccc(c(c1)O)O
• InChI: InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
• InChIKey: FHEHIXJLCWUPCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(prop-2-en-1-yl)benzene-1,2-diol
• IUPAC Traditional name: 4-allylpyrocatechol; 4-(prop-2-en-1-yl)benzene-1,2-diol
• Synonyms: 4-allylbenzene-1,2-diol; 1,2-Dihydroxy-4-allylbenzene; 4-(2-Propenyl)-1,2-benzenediol; 4-Allyl-1,2-benzenediol; 4-Allylcatechol; Allylpyrocatechol; 4-Allylpyrocatechol; 3,4-Dihydroxyallylbenzene; Hydroxychavicol

Database IDs

• CAS Number: 1126-61-0
• MDL Number: MFCD01548379
• Beilstein Number: 1937030
• PubChem SID: 162107413
• PubChem CID: 70775

CALCULATED PROPERTIES

• Acid pKa: 9.280201
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.4646144
• LogD (pH = 7.4): 2.459038
• Log P: 2.464686
• Molar Refractivity: 44.3071 cm^3
• Polarizability: 16.816748 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Oil
• Flash Point: 141 °C; 285.8 °F

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Antioxidant

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard
• Biological Source: Present in betel leaves
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antimutagen; Antioxidant; Antitumour
• Empirical Formula (Hill Notation): C9H10O2

REFERENCES

• Mitsui, S. et al., Chem. Pharm. Bull., 1976, 24, 2377, (synth)
• Rajashekkar, B. et al., J. Biol. Chem., 1984, 259, 6925, (synth)
• Chowdhury, A.K.A. et al., Pharmazie, 1993, 48, 786, (synth)
• Watanabe, N. et al., Biosci., Biotechnol., Biochem., 1995, 59, 1566, (di-Ac, isol, pmr, cmr, activity)