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Cinnamic acid is an organic compound with the formula C 6 H 5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. [ 4 ] Classified as an unsaturated carboxylic acid , it occurs naturally in a number of plants.
Phenylalanine ammonia-lyase (PAL, a.k.a. phenylalanine/tyrosine ammonia-lyase) is an enzyme that transforms L-phenylalanine and tyrosine into trans-cinnamic acid and p-coumaric acid, respectively. Trans-cinnamate 4-monooxygenase (cinnamate 4-hydroxylase) is the enzyme that transforms trans-cinnamate into 4-hydroxycinnamate (p-coumaric acid).
The systematic name of this enzyme class is trans-cinnamate,NADPH:oxygen oxidoreductase (2-hydroxylating). Other names in common use include cinnamic acid 2-hydroxylase , cinnamate 2-monooxygenase , cinnamic 2-hydroxylase , cinnamate 2-hydroxylase , and trans-cinnamic acid 2-hydroxylase .
trans-cinnamic acid phenylacrylic acid cinnamylic acid 3-phenylacrylic acid (E)-cinnamic acid benzenepropenoic acid isocinnamic acid: C 6 H 5 CH=CHCOOH: C10. IUPAC name:
The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalyzes the conversion of L-phenylalanine to ammonia and trans-cinnamic acid.: [1] L -phenylalanine = trans -cinnamate + NH 3 Phenylalanine ammonia lyase (PAL) is the first and committed step in the phenyl propanoid pathway and is therefore involved in the biosynthesis of the polyphenol ...
Hydroxylation of cinnamic acid in the 4-position by trans-cinnamate 4-monooxygenase leads to p-coumaric acid, which can be further modified into hydroxylated derivatives such as umbelliferone. Another use of p-coumaric acid via its thioester with coenzyme A, i.e. 4-coumaroyl-CoA, is the production of chalcones.
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In enzymology, a trans-cinnamate 4-monooxygenase (EC 1.14.14.91) is an enzyme that catalyzes the chemical reaction trans-cinnamate + NADPH + H + + O 2 ⇌ {\displaystyle \rightleftharpoons } 4-hydroxycinnamate + NADP + + H 2 O