Perillyl alcohol

(S)-(-)-Perillyl alcohol | (R)-(+)-Perillyl alcohol | (S)-(-)-Perillyl alcohol | | (R)-(+)-Perillyl alcohol | (S)-(-)-Perillyl alcohol | | | IUPAC name (4-Isopropenyl-1-cyclohexen-1-yl)methanol | | | | CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}536-59-4 Y | | | 3D model (JSmol) | Interactive image | | | ChemSpider | 10362 | | | ECHA InfoCard | 100.007.856 | | | PubChem CID | 10819 | | | UNII | 319R5C7293 Y | | | CompTox Dashboard (EPA) | DTXSID4052180 | | | InChI InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3Key: NDTYTMIUWGWIMO-UHFFFAOYSA-NInChI=1/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3Key: NDTYTMIUWGWIMO-UHFFFAOYAB | | | | SMILES CC(=C)C1CCC(=CC1)CO | | | | Chemical formula | 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).

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Perillyl alcohol 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. 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.

Perillyl alcohol has shown some antitumor activity in laboratory and animal studies. Perillyl Alcohol decrease production of proangiogenic growth factors VEGF and interleukin-8 (IL-8) in vitro.

Mammals possess enzymes (P450, liver) to convert limonene to perillyl alcohol. Limonene is formed from geranyl pyrophosphate in the mevalonate pathway. Conversion of limonene to perillyl alcohol is done via hydroxylation by enzymes that belong to the superfamily of cytochrome P450 proteins. Perillyl alcohol can be further converted to perillaldehyde (perillyl aldehyde) and perillic acid.

The name comes from the herb perilla.

• Perillaldehyde
• Limonene