methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

• ChemBase ID: 167586
• Molecular Formular: C11H14O4
• Molecular Mass: 210.22646
• Monoisotopic Mass: 210.08920893
• SMILES: c1c(c(cc(c1)CCC(=O)OC)OC)O
• Canonical SMILES: COC(=O)CCc1ccc(c(c1)OC)O
• InChI: InChI=1S/C11H14O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3,5,7,12H,4,6H2,1-2H3
• InChIKey: PDTCYIZPTRRYOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate
• IUPAC Traditional name: methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate
• Synonyms: 4-Hydroxy-3-methoxy-hydrocinnamic Acid Methyl Ester; Methyl 3-(4-Hydroxy-3-methoxyphenyl)propanoate; Methyl 3-[4-Hydroxy-3-(methyloxy)phenyl]propanoate; Methyl Dihydroferulate; Methyl Hydroferulate; Dihydro Ferulic Acid Methyl Ester

Database IDs

• CAS Number: 56024-44-3
• PubChem SID: 162261719
• PubChem CID: 523498

CALCULATED PROPERTIES

• Acid pKa: 9.945804
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.7402048
• LogD (pH = 7.4): 1.7389942
• Log P: 1.7402202
• Molar Refractivity: 55.1798 cm^3
• Polarizability: 21.604506 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Light Brown Oil

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D448995

A protected caffeine metabolite with high antioxidant activity. It is a very sensitive biomarker for the consumption of relatively small amount of coffee.

REFERENCES

• Buchanan, C., et al.: J. Sci. Food Agric., 71, 459 (1996)
• Andreasen, M., et al.: J. Agric. Food Chem., 49, 5679 (1996)
• Poquet, L., et al.: Drug Metab. Dispos., 36, 190 (1996)