Perillyl alcohol
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| Names | |||
|---|---|---|---|
| IUPAC name
(4-Isopropenyl-1-cyclohexen-1-yl)methanol | |||
| Identifiers | |||
| 536-59-4 | |||
| 3D model (Jmol) | Interactive image | ||
| ChemSpider | 10362 | ||
| ECHA InfoCard | 100.007.856 | ||
| PubChem | 10819 | ||
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| Properties | |||
| C10H16O | |||
| Molar mass | 152.24 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 | |||
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-Perillyl_alcohol.svg.png)
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 botanicals, 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] and as of 2015 it was in development as a potential treatment for people with brain cancer.[3]
Perillyl alcohol is only produced by certain botanicals, not by animals or humans. It is a metabolite of limonene, 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.[4]
See also
References
- ↑ 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.
- ↑ Laszlo P (2007). Citrus: A History. Chicago, IL: University of Chicago Press.
- ↑ 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. PMID 26175929.
- ↑ 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.