Perillyl alcohol
(R)-(+)-Perillyl alcohol
(S)-(-)-Perillyl alcohol
Names
IUPAC name
(4-Isopropenyl-1-cyclohexen-1-yl)methanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.856
UNII
  • InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
    Key: NDTYTMIUWGWIMO-UHFFFAOYSA-N
  • InChI=1/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
    Key: NDTYTMIUWGWIMO-UHFFFAOYAB
  • CC(=C)C1CCC(=CC1)CO
Properties
C10H16O
Molar mass 152.237 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Perillyl alcohol (IUPAC name: [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol) and its precursor limonene are naturally occurring monocyclic terpenes derived from the mevalonate pathway in plants. Perillyl alcohol can be found in the essential oils of various plants, such as lavender, lemongrass, sage, and peppermint.[1] It has a number of manufacturing, household, and medical applications. For example, perillyl alcohol may be used as an ingredient in cleaning products and cosmetics.[2]

Perillyl alcohol has shown some antitumor activity in laboratory and animal studies, but clinical trials in humans are lacking[3]

Perillyl alcohol is a metabolite of limonene,[4] which itself is formed from geranyl pyrophosphate in the mevalonate pathway. Conversion of limonene to perillyl alcohol is accomplished via hydroxylation by enzymes that belong to the superfamily of cytochrome P450 proteins. Perillyl alcohol can be metabolized further to perillaldehyde (perillyl aldehyde) and perillic acid.[5]

The name comes from the herb perilla.

See also

References

  1. ↑ Crowell PL, Elson CE (2001). Isoprenoids, Health and Disease. In: Wildman REC, editors. Neutraceuticals and Functional Foods. Boca Raton, FL: CRC Press, LLC. pp. 31–53.
  2. ↑ Laszlo P (2007). Citrus: A History. Chicago, IL: University of Chicago Press.
  3. ↑ "Perillyl Alcohol". Memorial Sloan Kettering Cancer Center.
  4. ↑ Chen TC, Da Fonseca CO, Schönthal AH (2015). "Preclinical development and clinical use of perillyl alcohol for chemoprevention and cancer therapy". American Journal of Cancer Research. 5 (5): 1580–93. PMC 4497427. PMID 26175929.
  5. ↑ Mann, J. C.; Hobbs, J. B.; Banthorpe, D. V.; Harborne, J. B. (1994). Natural products: their chemistry and biological significance. Harlow, Essex, England: Longman Scientific & Technical. pp. 308–9. ISBN 0-582-06009-5.
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