Definition
ChEBI: (E)-2-methoxycinnamic acid is a member of the class of cinnamic acids that is trans-cinnamic acid carrying a methoxy substituent at position 2 on the benzene ring. It has a role as a Brassica napus metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a member of cinnamic acids and a monomethoxybenzene. It is functionally related to a trans-cinnamic acid.
Synthesis
To a 500 mL three-necked round-bottomed flask was added o-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 eq.), pyridine (250 mL), malonic acid (18.3 g, 175.86 mmol, 1.20 eq.) and piperidine (2.5 g, 29.36 mmol, 0.20 eq.). The reaction mixture was stirred at 85°C overnight. Upon completion of the reaction, most of the solvent was removed by distillation under reduced pressure, followed by adjusting the pH of the remaining solution with aqueous hydrochloric acid to 3.0. The precipitated solid was collected by filtration to afford 25.6 g (98% yield) of 2-methoxycinnamic acid as a white solid.
References
[1] Patent: WO2014/182950, 2014, A1. Location in patent: Paragraph 00322; 00323
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 187 - 191
[4] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4513 - 4519
