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

• ChemBase ID: 154902
• Molecular Formular: C14H12O4
• Molecular Mass: 244.24268
• Monoisotopic Mass: 244.07355886
• SMILES: c1cc(c(cc1O)O)/C=C/c1cc(cc(c1)O)O
• Canonical SMILES: Oc1ccc(c(c1)O)/C=C/c1cc(O)cc(c1)O
• InChI: InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H
• InChIKey: PDHAOJSHSJQANO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; 5-[(E)-2-(2,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• IUPAC Traditional name: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; 5-[(E)-2-(2,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• Synonyms: (E)-2,3′,4,5′-Stilbenetetrol; 2,3′,4,5′-Tetrahydroxy-trans-stilbene; 4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol; Oxyresveratrol

Database IDs

• CAS Number: 29700-22-9
• MDL Number: MFCD11974969
• PubChem SID: 162249040
• PubChem CID: 5281717

CALCULATED PROPERTIES

• Acid pKa: 8.848038
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 3.0986319
• LogD (pH = 7.4): 3.0835683
• Log P: 3.0988255
• Molar Refractivity: 69.4364 cm^3
• Polarizability: 25.926739 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C14H12O4

DETAILS

Sigma Aldrich - 91211

Biochem/physiol Actions
Potent antioxidant and free-radical scavenger with demonstrated protective effects against cerebral ischemia and neuroprotective effects against traumatic injury1, inhibits the apoptotic cell death in transient cerebral ischemia2, inhibitory activity on viral DNA replication and late viral protein synthesis of African Swine fever virus3, inhibitory effect on DOPA oxidase activity of mushroom tyrosinase4.