(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid

• ChemBase ID: 170165
• Molecular Formular: C9H8O3
• Molecular Mass: 164.15802
• Monoisotopic Mass: 164.04734412
• SMILES: c1c(ccc(c1)/C=C\C(=O)O)O
• Canonical SMILES: OC(=O)/C=C\c1ccc(cc1)O
• InChI: InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-
• InChIKey: NGSWKAQJJWESNS-UTCJRWHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: cis-p-coumaric acid
• Synonyms: (2Z)-3-(4-Hydroxyphenyl)-2-propenoic Acid; (Z)-3-(4-hydroxyphenyl)-2-propenoic Acid; (Z)-p-hydroxycinnamic Acid; (Z)-p-Coumaric Acid; cis-p-Coumaric Acid; cis-p-Hydroxycinnamic Acid; cis-4-Hydroxycinnamic Acid

Database IDs

• CAS Number: 4501-31-9
• PubChem SID: 164226075
• PubChem CID: 1549106

CALCULATED PROPERTIES

• Acid pKa: 3.5022438
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.15703769
• LogD (pH = 7.4): -1.5454916
• Log P: 1.832521
• Molar Refractivity: 45.0408 cm^3
• Polarizability: 16.806936 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825070

An antioxidative active compound isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste. Photoisomerization of ionic liquid ammonium cinnamates. Cinnamic acids upon irradiation in solution undergo geometric isomeriz

REFERENCES

• Armstrong, D., et al.: Anal. Chem., 73, 3679 (2001)
• Karmakar, B., et al.: J. Biotech., 80, 195 (2001)