methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

• ChemBase ID: 128332
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: COC(=O)/C=C/c1cc(c(cc1)O)O
• Canonical SMILES: COC(=O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3
• InChIKey: OCNYGKNIVPVPPX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate; methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: methyl caffeate; methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• Synonyms: (E)-3-(3,4-Dihydroxyphenyl)propenoic Acid Methyl Ester; Caffeic Acid Methyl Ester; Caffeic acid methyl ester; methylcaffeate; Methyl 3,4-dihydroxycinnamate; Methyl caffeate; Methyl 3-(3,4-dihydroxyphenyl)acrylate; (E)-Methyl 3-(3,4-dihydroxyphenyl)acrylate

Database IDs

• CAS Number: 3843-74-1; 67667-67-8
• MDL Number: MFCD00210468
• PubChem SID: 162222640
• PubChem CID: 689075
• Wikipedia Title: Methyl_caffeate

CALCULATED PROPERTIES

• Acid pKa: 9.208666
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9080986
• LogD (pH = 7.4): 1.9015322
• Log P: 1.908183
• Molar Refractivity: 51.7908 cm^3
• Polarizability: 19.525229 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; DMSO; Ethyl Acetate
• Apperance: Off-White Solid

Product Information

• Purity: 95+%; 97%

DETAILS

Toronto Research Chemicals - C080040

Protected Caffeic Acid

REFERENCES

• Kurata, A., et al.: J. Biotechnol., 148, 133 (2010)
• Buzzi, F., et al.: Eur. J. Med. Chem., 44, 4596 (2010)
• Xu, G., et al.: Arch. Pharm., Res., 32, 1215 (2010)