benzyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

• ChemBase ID: 163526
• Molecular Formular: C16H14O4
• Molecular Mass: 270.27996
• Monoisotopic Mass: 270.08920893
• SMILES: c1c(c(cc(c1)/C=C/C(=O)OCc1ccccc1)O)O
• Canonical SMILES: O=C(OCc1ccccc1)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H14O4/c17-14-8-6-12(10-15(14)18)7-9-16(19)20-11-13-4-2-1-3-5-13/h1-10,17-18H,11H2
• InChIKey: WWVKQTNONPWVEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: benzyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• Synonyms: 3-(3,4-Dihydroxyphenyl)-2-propenoic Acid Phenylmethyl Ester; 3-(3,4-Dihydroxyphenyl)-2-propenoic Acid Benzyl Ester; Benzyl Caffeate; NSC 666590; Caffeic Acid Benzyl Ester

Database IDs

• CAS Number: 107843-77-6
• PubChem SID: 162257661
• PubChem CID: 5919576

CALCULATED PROPERTIES

• Acid pKa: 9.208616
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.6325717
• LogD (pH = 7.4): 3.6260045
• Log P: 3.632656
• Molar Refractivity: 76.4034 cm^3
• Polarizability: 29.086771 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C080005

Caffeic Acid analog potentially having anti-inflammatory effects.

REFERENCES

• Gardana, C., et al.: J. Pharm. Biomed. Anal., 45, 390 (2007)
• Falcao, S., et al.: Anal. Bioanal. Chem., 396, 887 (2007)