Phenylpropene

Allylbenzene parent structure

Phenylpropene is a chemical compound. The syllable '-en' in propene indicates the double bond, as opposed e.g. to phenylpropane. In plant biochemistry, phenylpropene is derived from the general shikimate/phenylpropanoid synthesis pathway, and belong to the immensely diverse and important class of phenylpropanoids.[1] Phenylpropene is the scaffold for a class of derivatives called phenylpropenoids, that may also be called Phenylpropenes, propenylphenols, alkenylbenzenes or allylbenzenes.

Industrial uses

Phenylpropenoids have been used as a precursors for a variety of effective insecticides.[2]

Safrole, a phenylpropene found in sassafras

Human Pharmacokinetics

Dosage determines concern: There is long standing and wide use as flavors at doses low enough to be insignificant, but high doses as in medicinal use can be a concern. Phenylpropene compounds are readily metabolized to reactive carcinogens which are also rapidly metabolized to safe compounds that are excreted. Thus the metabolism of these molecules quickly progresses from flavor to toxin to safe excretion.

Alkenylbenzenes at high dose can be activated metabolically (by P450, sulfotransferase) to reactive intermediates that bind DNA, but are also rapidly converted to less toxic dihydrodiol or glutathione conjugates.[3]

The phenylpropenes, including eugenol, chavicol, safrole and estragole, are derived from the monolignols. These compounds are the primary constituents of various essential oils.

See also

References

  1. ↑ Vogt, Thomas (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3 (1): 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
  2. ↑ Fujita, Harushige; Yamashita, Masataro (1973). "The Methylenation of Several Allylbenzene-1,2-diol Derivatives in Aprotic Polar Solvents". Bulletin of the Chemical Society of Japan. 46 (11): 3553–4. doi:10.1246/bcsj.46.3553.
  3. ↑ Guenthner, Thomas M; Luo, Gang (2001). "Investigation of the role of the 2′,3′-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs". Toxicology. 160 (1–3): 47–58. doi:10.1016/S0300-483X(00)00456-X. PMID 11246123.


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