5-[(Z)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol

• ChemBase ID: 177411
• Molecular Formular: C14H12O3
• Molecular Mass: 228.24328
• Monoisotopic Mass: 228.07864424
• SMILES: c1(cc(cc(c1)/C=C\c1ccc(cc1)O)O)O
• Canonical SMILES: Oc1ccc(cc1)/C=C\c1cc(O)cc(c1)O
• InChI: InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1-
• InChIKey: LUKBXSAWLPMMSZ-UPHRSURJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(Z)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
• IUPAC Traditional name: cis-resveratrol
• Synonyms: 5-[(1Z)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol; cis-3,4',5-Trihydroxystilbene; Z-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol; (Z)-Resveratrol; cis-Resveratrol

Database IDs

• CAS Number: 61434-67-1
• PubChem SID: 164233321
• PubChem CID: 1548910

CALCULATED PROPERTIES

• Acid pKa: 8.993489
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.4022524
• LogD (pH = 7.4): 3.3914592
• Log P: 3.402391
• Molar Refractivity: 67.4555 cm^3
• Polarizability: 25.321121 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: >135°C (dec)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Light, Moisture, Temperature Sensitive and Hygroscopic; Stor

DETAILS

Toronto Research Chemicals - R150005

Minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associa

REFERENCES

• Powell, R.G., et al.: Phytochemistry, 35, 335 (1994)
• Jeandet, P., et al.: J. Phytopathol., 143, 135 (1994)
• Mattivi, F., et al.: J. Agric. Food Chem., 43, 1820 (1994)