2-phenylethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

• ChemBase ID: 163532
• Molecular Formular: C18H18O4
• Molecular Mass: 298.33312
• Monoisotopic Mass: 298.12050906
• SMILES: c1(c(ccc(c1)/C=C/C(=O)OCCc1ccccc1)O)OC
• Canonical SMILES: COc1cc(/C=C/C(=O)OCCc2ccccc2)ccc1O
• InChI: InChI=1S/C18H18O4/c1-21-17-13-15(7-9-16(17)19)8-10-18(20)22-12-11-14-5-3-2-4-6-14/h2-10,13,19H,11-12H2,1H3/b10-8+
• InChIKey: CZQNYPBIOHVQQN-CSKARUKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenylethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• IUPAC Traditional name: 2-phenylethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• Synonyms: 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic Acid 2-Phenylethyl Ester; 2-Phenylethyl Ferulate; Ferulic Acid Phenethyl Ester; NSC 666255; NSC 671193; Phenethyl Ferulate; Phenethyl 3-Methylcaffeate; Caffeic Acid 3-Methyl Phenethyl Ester

Database IDs

• CAS Number: 71835-85-3
• PubChem SID: 162257667
• PubChem CID: 5284444

CALCULATED PROPERTIES

• Acid pKa: 9.867805
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.067193
• LogD (pH = 7.4): 4.065745
• Log P: 4.067211
• Molar Refractivity: 85.6407 cm^3
• Polarizability: 32.84545 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Ethyl Acetate

DETAILS

Toronto Research Chemicals - C080030

It has chemopreventive properties against chemically induced colon carcinogenesis. It enhances apoptosis in azoxymethane induced colon tumors.

REFERENCES

• Rao, C.V., et al.: Cancer Res., 55, 2310 (1995)
• Samaha, H.S., et al.: Cancer Res., 57, 1301 (1995)
• Tang, S., et al.: Chem. Res. Toxicol., 21, 2414 (1995)
• Yamazaki, Y., et al.: Life Sci., 82, 290 (1995)