Perillyl alcohol and its precursor

limonene Limonene () is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, ...

are naturally occurring monocyclic

terpenes Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predomi ...

derived from the

mevalonate pathway The mevalonate pathway, also known as the isoprenoid pathway or HMG-CoA reductase pathway is an essential metabolic pathway present in eukaryotes, archaea, and some bacteria. The pathway produces two five-carbon building blocks called isopentenyl ...

in plants. Perillyl alcohol can be found in the

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

s of various plants, such as

lavender ''Lavandula'' (common name lavender) is a genus of 47 known species of perennial flowering plants in the sage family, Lamiaceae. It is native plant, native to the Old World, primarily found across the drier, warmer regions of the Mediterranean ...

lemongrass ''Cymbopogon'', also known as lemongrass, barbed wire grass, silky heads, oily heads, Cochin grass, Malabar grass, citronella grass or fever grass, is a genus of Asian, African, Australian, and tropical island plants in the grass family. Some ...

sage #REDIRECT Sage {{redirect category shell, {{R from other capitalisation{{R from ambiguous page ...

, and

peppermint Peppermint (''Mentha'' × ''piperita'') is a Hybrid (biology), hybrid species of Mentha, mint, a cross between Mentha aquatica, watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in m ...

. 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 Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many thousands of natural product, natural products. Occurrence GPP is an int ...

in the mevalonate pathway. Conversion of limonene to perillyl alcohol is done via

hydroxylation In chemistry, hydroxylation refers to the installation of a hydroxyl group () into an organic compound. Hydroxylations generate alcohols and phenols, which are very common functional groups. Hydroxylation confers some degree of water-solubility ...

by enzymes that belong to the superfamily of

cytochrome P450 Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...

proteins. Perillyl alcohol can be further converted to

perillaldehyde Perillaldehyde, perillic aldehyde or perilla aldehyde, is a natural organic compound found most abundantly in the annual herb perilla, but also in a wide variety of other plants and essential oils. It is a monoterpenoid containing an aldehyde f ...

(perillyl aldehyde) and perillic acid. The name comes from the herb

perilla ''Perilla'' is a genus consisting of one major Asiatic crop species '' Perilla frutescens'' and a few wild species in nature belonging to the mint family, Lamiaceae. The genus encompasses several distinct varieties of Asian herb, seed, and vege ...

References

{{reflist Primary alcohols Terpenes and terpenoids Cyclohexenes Isopropenyl compounds

See also

References