perillyl alcohol

{{Chembox

| ImageFileL1 = (+)-Perillyl alcohol.svg

| ImageSizeL1 = 120px

| ImageCaptionL1 = (R)-(+)-Perillyl alcohol

| ImageFileR1 = (-)-Perillyl alcohol.svg

| ImageSizeR1 = 120px

| ImageCaptionR1 = (S)-(-)-Perillyl alcohol

| IUPACName = (4-Isopropenyl-1-cyclohexen-1-yl)methanol

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|Section1={{Chembox Identifiers

| CASNo = 536-59-4

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| UNII = 319R5C7293

| PubChem = 10819

| ChemSpiderID = 10362

| SMILES = CC(=C)C1CCC(=CC1)CO

| InChI = 1/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3

| InChIKey = NDTYTMIUWGWIMO-UHFFFAOYAB

| StdInChI = 1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3

| StdInChIKey = NDTYTMIUWGWIMO-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=10 | H=16 | O=1

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|Section3={{Chembox Hazards

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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.{{cite book |vauthors=Crowell PL, Elson CE|name-list-style=amp |title=Isoprenoids, Health and Disease. In: Wildman REC, editors. Neutraceuticals and Functional Foods |pages=31–53 |publisher=CRC Press, LLC |location=Boca Raton, FL |year=2001}} 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.{{cite book |author=Laszlo P |title=Citrus: A History |publisher=University of Chicago Press |location=Chicago, IL |year=2007}}

Perillyl alcohol has shown some antitumor activity in laboratory and animal studies.{{cite web | url = https://www.mskcc.org/cancer-care/integrative-medicine/herbs/perillyl-alcohol | title = Perillyl Alcohol | publisher = Memorial Sloan Kettering Cancer Center }}

Perillyl Alcohol decrease production of proangiogenic growth factors VEGF and interleukin-8 (IL-8) in vitro.{{cite journal |vauthors=Chen TC, Da Fonseca CO, Schönthal AH |title=Preclinical development and clinical use of perillyl alcohol for chemoprevention and cancer therapy |journal=American Journal of Cancer Research |volume=5 |issue=5 |pages=1580–93 |date=2015 |pmid=26175929 |pmc=4497427}}

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.{{cite book |author1=Mann, J. C. |author2=Hobbs, J. B. |author3=Banthorpe, D. V. |author4=Harborne, J. B. |title=Natural products: their chemistry and biological significance |publisher=Longman Scientific & Technical |location=Harlow, Essex, England |year=1994 |pages=[https://archive.org/details/isbn_9780582060098/page/308 308–9] |isbn=0-582-06009-5 |url-access=registration |url=https://archive.org/details/isbn_9780582060098/page/308 }}

The name comes from the herb perilla.