1131-94-8

Pale Beige Solid

3-Hydroxy-4-methoxyphenylacetic acid is a 4-O-methylated metabolite of catechol amines in man. 3-Hydroxy-4-methoxyphenylacetic acid is also a metabolite of 3,4-dihydroxyphenylalanine (DOPA) analogues as well as a metabolite of Hydroxytyrosol (H977000).

ChEBI: A monocarboxylic acid that is the 4-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid.

The Journal of Organic Chemistry, 49, p. 2061, 1984 DOI: 10.1021/jo00185a061

General procedure for the synthesis of 3-hydroxy-4-methoxyphenylacetic acid from 3-bromo-4-methoxyphenylacetic acid: sodium hydroxide (24.5 g, 612 mmol) and copper sulfate pentahydrate (1.02 g, 4.08 mmol) were added to a 125 mL sealed tube, followed by the addition of water (60 mL) to dissolve. The mixture was cooled and 3-bromo-4-methoxyphenylacetic acid (10 g, 40.8 mmol) was added. The reaction tube was sealed and placed in an oil bath at 150°C with stirring for 20 hours. After completion of the reaction, it was cooled to room temperature and the pH was adjusted slowly and dropwise to 3 by adding concentrated hydrochloric acid.The reaction mixture was filtered by pumping and the filter cake was washed with water. The collected solid was purified by column chromatography (eluent: dichloromethane/methanol, 30:1, v/v) to give an off-white solid product (3.3 g, 44.4% yield).

Human Endogenous Metabolite

[1] Journal of Organic Chemistry, 1984, vol. 49, # 11, p. 2061 - 2063
[2] Synthesis, 2011, # 2, p. 217 - 222
[3] Patent: WO2010/75469, 2010, A1. Location in patent: Page/Page column 115
[4] Patent: US2011/9628, 2011, A1. Location in patent: Page/Page column 37
[5] Patent: CN105481849, 2016, A. Location in patent: Paragraph 0461; 0465; 0466