3-(acetyloxy)-5-[(E)-2-[4-(acetyloxy)phenyl]ethenyl]phenyl acetate

• ChemBase ID: 77391
• Molecular Formular: C20H18O6
• Molecular Mass: 354.35332
• Monoisotopic Mass: 354.1103383
• SMILES: O(c1ccc(cc1)/C=C/c1cc(cc(c1)OC(=O)C)OC(=O)C)C(=O)C
• Canonical SMILES: CC(=O)Oc1ccc(cc1)/C=C/c1cc(OC(=O)C)cc(c1)OC(=O)C
• InChI: InChI=1S/C20H18O6/c1-13(21)24-18-8-6-16(7-9-18)4-5-17-10-19(25-14(2)22)12-20(11-17)26-15(3)23/h4-12H,1-3H3
• InChIKey: PDAYUJSOJIMKIS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(acetyloxy)-5-[(E)-2-[4-(acetyloxy)phenyl]ethenyl]phenyl acetate; 4-{2-[3,5-bis(acetyloxy)phenyl]ethenyl}phenyl acetate
• IUPAC Traditional name: 3-(acetyloxy)-5-[(E)-2-[4-(acetyloxy)phenyl]ethenyl]phenyl acetate; 4-{2-[3,5-bis(acetyloxy)phenyl]ethenyl}phenyl acetate
• Synonyms: trans-Resveratrol Triacetate; Triacetyl Resveratrol; 3,5,4'-Tri-O-acetylresveratrol; 5-[(1E)-2-[4-(Acetyloxy)phenyl]ethenyl]-1,3-benzenediol1,3-Diacetate; Resveratrol 3,5,4'-triacetate; 3,4',5-Triacetoxy-trans-stilbene; trans-Triacetylresveratrol; trans-Resveratrol triacetate; 4-[(E)-2-(3,5-Diacetoxyphenyl)vinyl]phenyl acetate 98+%; 5-[(1E)-2-[4-(acetyloxy)phenyl]ethenyl]-1,3-Benzenediol-1,3-diacetate; 3,5,4′-Tri-O-acetylresveratrol; Triacetyl resveratrol

Database IDs

• CAS Number: 42206-94-0
• MDL Number: MFCD01546481
• PubChem SID: 162042264
• PubChem CID: 5962587

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.1348698
• LogD (pH = 7.4): 3.1348698
• Log P: 3.1348698
• Molar Refractivity: 94.91 cm^3
• Polarizability: 36.8026 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥18 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Condition: protect from light
• Storage Warning: Irritant
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41-43-50/53
• Safety Statements: 26-36/37/39-60-61
• GHS Pictograms: GHS05; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H318-H335-H400
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H18O6

DETAILS

Sigma Aldrich - SML0032

Biochem/physiol Actions
Triacetyl resveratrol displays superior bioavailability to the parent compound, resveratrol. The compound induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines.

Toronto Research Chemicals - R150055

trans-Resveratrol Triacetate is the acetylated analogue of Resveratrol (R150000) that is a natural antioxidant and a potential radioprotective agent. trans-Resveratrol Triacetate induces p53 activity and inhibits proliferation in breast and prostate tumor

REFERENCES

• Torres, P. et al.: J. Agric. Food Chem., 58, 807 (2010)
• Kotagiri, S. et al.: J. Chem. Pharmac. Sci., 3, 191 (2010)
• Koide, K. et al.: ACS Med. Chem. Chem. Lett., 2, 270 (2010)