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EC number: 701-219-0 | CAS number: 15174-47-7
The position and size of the substituent play a role in the metabolism of cinnamyl derivatives. Those containing alpha-methyl substituents (e.g. alpha-methylcinnamaldehyde) are extensively metabolized via beta-oxidation and cleavage to yield mainly the corresponding hippuric acid derivative. A benzoic acid metabolite was isolated from the urine of dogs given either alpha-methylcinnamic acid or alpha-methylphenylpropionic acid (Kay & Raper, 1924). Larger substituents located at the alpha- or beta-position inhibited beta-oxidation to some extent (Deuel, 1957; Kassahun et al., 1991), in which case there may be direct conjugation of the carboxylic acid with glucuronic acid, followed by excretion. While alpha-methylcinnamic acid undergoes oxidation to benzoic acid, alpha-ethyl- and alpha-propylcinnamic acids are excreted unchanged (Carter, 1941). alpha-Ethylcinnamic alcohol and alpha-ethylcinnamaldehyde administered orally to rabbits resulted in urinary excretion of alpha-ethylcinnamic acid and of small amounts of benzoic acid (Fischer & Bielig, 1940). These observations suggest that alpha-methylcinnamaldehyde undergoes oxidation to benzoic acid, while higher homologues are excreted primarily unchanged or as the conjugated form of the cinnamic acid derivative.
Kay, H. & Raper, H. (1924) The mode of oxidation of fatty acids with branched chains. III.Biochemistry,18, 153–160
Deuel, H.J. (1957) The oxidation and metabolism of triglycerides, fatty acids, and glycerol in the animal body. In:The Lipids, Their Chemistry and Biochemistry,: Wiley Interscience, Vol. III, pp. 71–99, 291–301
Kassahun, K., Farrell, K. & Abbott, F. (1991) Identification and characterization of the glutathione and N-acetylcysteine conjugates of (E)-2-propyl-2,4-pentadienoic acid, a toxic metabolite of valproic acid, in rats and humans.Drug Metab. Disposition,19, 525–535
Fischer, F.G. & Bielig, H.J. (1940) On the hydrogenation of unsaturated materials in the animal body.Z. Physiol. Chem.,266,73–98
Summary safety evaluations of cinnamyl alcohol and related flavouring agents
Oxidized to cinnamic acid or its corresponding derivative and further oxidized to benzoic acid or its corresponding derivative, which is excreted as hippuric acid or its corresponding derivative
The cinnamyl derivatives used as flavouring substances are simple aromatic compounds with a propyl side-chain containing a primary oxygenated functional group, and they participate in common routes of absorption, distribution, and metabolism. The members of this group may be hydrolysed to yield the component alcohol, aldehyde, or acid. If the product is an alcohol or aldehyde, it is oxidized to yield the corresponding 3-phenylpropenoic acid or a 3-phenylpropanoic acid derivative which undergoes further side-chainbeta-oxidation and cleavage to yield mainly the corresponding benzoic acid derivatives (see attachment; Williams, 1959). The benzoic acid derivatives are conjugated with glycine and, to a lessor extent, glucuronic acid and excreted primarily in the urine (Snapper et al., 1940).ortho-Alkyl- andortho-alkoxy-substituted cinnamaldehyde derivatives undergobeta-oxidation to a minor extent, to yieldbeta-hydroxy-3-phenylpropanoic acid metabolites that are excreted as the glucuronic acid conjugates (Solheim & Scheline, 1973, 1976; Samuelsen et al., 1986).
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