Chemical Properties
Off-White Crystalline Solid
Uses
3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered
Saccharomyces cerevisiae yeast strain. It was also used in the synthesis of glycoside compounds by undergoing glycosidation.
Uses
3-Hydroxy-4-methoxycinnamic acid exhibits hypoglycemic properties.
Uses
3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.
Definition
ChEBI: A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.
General Description
3-Hydroxy-4-methoxycinnamic acid, predominantly
trans is available as white crystals. 3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of
Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic. It is an efficient acetylcholine inhibitor. 3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of
Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation.
Synthesis
To a suspension of isovanillin (152 mg, 1.00 mmol) and malonic acid (416 mg, 4.00 mmol) in toluene (5 mL) was added triethylamine (0.70 mL, 5.00 mmol) and N,N-dimethylformamide dimethyl acetal (0.20 mL, 1.50 mmol). The reaction mixture was heated to reflux for 4 hours, subsequently cooled to room temperature and concentrated on a rotary evaporator. The residue was dissolved in 1 M NaOH solution (20 mL) and the resulting solution was washed with dichloromethane (3 x 20 mL). The aqueous phase was acidified to pH 1 by the addition of 3 M HCl. The milky precipitate formed was collected in a Hirsch funnel, washed with dilute hydrochloric acid and air dried. The precipitate was recrystallized by solvent recrystallization in a methanol-water mixture and dried in a vacuum desiccator using phosphorus pentoxide as a drying agent to give trans-3-hydroxy-4-methoxycinnamic acid (164 mg, 85% yield) as a cream-colored crystalline solid.1H NMR spectroscopic data were in agreement with those reported in the literature (McCorkindale, N.J.; McCulloch, A.W. Magrill, D.S.; Caddy, B.; Martin-Smith, M.; Smith, S.J.; Stenlake, J.B. Tetrahedron 1969, 25, 5475).
IC 50
α adrenergic receptor
References
[1] Synthetic Communications, 1995, vol. 25, # 20, p. 3187 - 3197
[2] Chemical Communications, 1998, # 21, p. 2335 - 2336
[3] Tetrahedron, 2007, vol. 63, # 4, p. 960 - 965
[4] Tetrahedron Letters, 2012, vol. 53, # 20, p. 2537 - 2539
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2707 - 2713
