(E)-3-(2-Chlorophenyl)acrylic acid;AKOS BBB/195;AKOS B004073;AKOS BBS-00006452;Chlorocinnamicacid;RARECHEM BK HC T319;2-Chlorocinnamicaci;o-chloro-cinnamicaci;2-CLOROCINNAMIC ACID;O-CHLOROCINNAMIC ACID
white to light yellow crystal powder. Insoluble in water, soluble in ethanol, ethyl acetate and other organic solvents.
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2-Chlorocinnamic acid is a kind of trans-cinnamate. It is used in organic synthesis.
Biological Functions
2-Chlorocinnamic acid is a cinnamic acid derivative that inhibits the hydroxylation of phenylpropanoids. It has been shown to inhibit the activity of cinnamic acid derivatives and their hydroxylation in cell lines, which is linked to the inhibition of cellulose acetate synthesis. 2-Chlorocinnamic acid also has an inhibitory effect on the chloride ion and water molecule. The chloride ion may be needed for the formation of hydrochloric acid, which is necessary for cellulose acetate hydrolysis, while water molecules are involved in many biochemical reactions. 2-Chlorocinnamic acid affects human cell lines at temperatures between 10°C and 37°C and at regiospecific sites. This oxidative dehalogenation reaction catalyzed by R. rubra was found to be regiospecific for 2-chlorocinnamic acid; the chloride ion was probably removed after the ring fission reaction.
Synthesis
O-chlorocinnamic acid is prepared by reacting o-phthalaldehyde with malonic acid.
