p-Coumaric acid

Description

In 1865, the Austrian chemist H. Hlasiwetz isolated the crystalline solid?p-coumaric acid from plants. The acid is biosynthesized from cinnamic acid and occurs in many parts of legumes and other edible plant species.
Recently, M. R. Berenbaum and colleagues at the University of Illinois (Urbana-Champaign) found that?honeybees fed with honey are more pesticide-resistant?than those fed with substitutes such as corn syrup. They showed that?p-coumaric acid extracted from honey increases bees’ metabolism of the miticide coumaphos.

Chemical properties

Off-white to beige or greenish powder. Soluble in alcohol, ether and hot water, slightly soluble in benzene, insoluble in petroleum ether.

The Uses of p-Coumaric acid

trans-p-Coumaric Acid is the E-isomer of p-Coumaric Acid (C755365), a hydroxy derivative of Cinnamic Acid with antioxidant properties. p-Coumaric acid is a is a major component of lignocellulose. Stud ies suggest that p-Coumaric Acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.

What are the applications of Application

p-Coumaric acid is a hydroxycinnamic acid with antioxidant properties

Definition

ChEBI: p-coumaric acid is the trans-isomer of 4-coumaric acid. 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.

What are the applications of Application

trans-4-Hydroxycinnamic acid is used as a hydroxycinnamic acid with antioxidant properties. p-Coumaric acid is an aromatic phytochemical for proteomics research. It has been used as a component of chemiluminescent substrate for protein detection in western blotting.

Preparation

Synthesis of p-Coumaric acid: take o-acetylsalicyloyl chloride as raw material, in the presence of magnesium chloride, react with diethyl malonate in acetonitrile solvent, then add triethylamine, and react at 0°C for 1 h to obtain ( 2-acetoxybenzoyl) diethyl malonate product, then heated to 50°C in potassium hydroxide/methanol solution, reacted for 3h, and cyclized to obtain p-Coumaric acid.

Biochem/physiol Actions

p-Coumaric acid is mainly a plant metabolite which exhibits antioxidant and anti-inflammatory properties. It also shows bactericidal activity by damaging bacterial cell membrane and by interacting with bacterial DNA. In western blot, p-coumaric is also used as an enhancer in chemiluminescent substrate.
Hydroxycinnamic acid found in many fruits and vegetables.

Purification Methods

Crystallise p-coumaric acid from H2O (charcoal). It forms needles from concentrated aqueous solutions as the anhydrous acid, but from hot dilute solutions the monohydrate acid separates on slow cooling. The acid (33g) has been crystallised from 2.5L of H2O (1.5g charcoal) yielding 28.4g of recrystallised acid, m 207o. It is insoluble in *C6H6 or pet ether. The UV in 95% EtOH has max 223 and 286nm ( 14,450 and 19000 M-1cm-1). [UV Wheeler & Covarrubias J Org Chem 28 2015 1963, Corti Helv Chim Acta 32 681 1949, Beilstein 10 IV 1005.]