(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoic acid

• ChemBase ID: 162148
• Molecular Formular: C13H12O6
• Molecular Mass: 264.23078
• Monoisotopic Mass: 264.0633881
• SMILES: c1(c(ccc(c1)/C=C/C(=O)O)OC(=O)C)OC(=O)C
• Canonical SMILES: OC(=O)/C=C/c1ccc(c(c1)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H12O6/c1-8(14)18-11-5-3-10(4-6-13(16)17)7-12(11)19-9(2)15/h3-7H,1-2H3,(H,16,17)/b6-4+
• InChIKey: ZDIYGBWFISUTHI-GQCTYLIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoic acid
• Synonyms: (E)-Caffeic Acid Diacetate; 3-[3,4-Bis(acetyloxy)phenyl]-2-propenoic Acid

Database IDs

• CAS Number: 88623-81-8
• PubChem SID: 162256283
• PubChem CID: 5374732

CALCULATED PROPERTIES

• Acid pKa: 3.3621268
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.773136
• LogD (pH = 7.4): -2.0615728
• Log P: 1.3506082
• Molar Refractivity: 65.3247 cm^3
• Polarizability: 25.149828 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Light Brown

DETAILS

Toronto Research Chemicals - B400650

Protected Caffeic Acid (C080000), a constituent of plants.

REFERENCES

• Neish, et al.: Can. J. Biochem Physiol., 37, 1431 (1959)
• Krasemann, et al.: Arch. Pharm., et al.: 293, 721 (1960)