Phytol
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| Names | |
|---|---|
| IUPAC names
(2E,7R,11R)-3,7,11,15-
tetramethyl-2-hexadecen-1-ol |
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| Identifiers | |
7541-49-3  |
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| ChEBI | CHEBI:17327 |
| ChEMBL | ChEMBL3039479  |
| ChemSpider | 4444094 |
| Jmol 3D model | Interactive image |
| PubChem | 5280435 |
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| Properties | |
| C20H40O | |
| Molar mass | 296.54 g·mol−1 |
| Density | 0.850 g cm−3 |
| Boiling point | 203 to 204 °C (397 to 399 °F; 476 to 477 K) at 10 mmHg |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E[1] and vitamin K1.[2] In ruminants, the gut fermentation of ingested plant materials liberates phytol, a constituent of chlorophyll, which is then converted to phytanic acid and stored in fats.[3]
Contents
Human pathology
Refsum disease, an autosomal recessive disorder that results from the accumulation of large stores of phytanic acid in tissues, frequently manifests peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss.[4] Although humans cannot derive phytanic acid from chlorophyll, they can convert free phytol into phytanic acid. Thus, patients with Refsum disease should limit their intake of phytanic acid and free phytol.[5] The amount of free phytol in numerous food products has been reported.[6]
Roles in nature
Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. phytanic acid) as chemical deterrents against predation.[7] These compounds originate from host plants.
Indirect evidence has been provided that, in contrast to humans, diverse non-human primates can derive significant amounts of phytol from the hindgut fermentation of plant materials.[8][9]
Modulator of transcription
Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha [10] and retinoid X receptor (RXR).[11] The metabolites phytanic acid and pristanic acid are naturally occurring ligands.[12] In mice oral phytol induces massive proliferation of peroxisomes in several organs.[13]
Geochemical biomarker
Phytol is likely the most abundant acyclic isoprenoid compound present in the biosphere and its degradation products have been used as biogeochemical tracers in aquatic environments.[14]
Commercial applications
Phytol is used in the fragrance industry and used in cosmetics, shampoos, toilet soaps, household cleaners, and detergents.[15] Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.[16]
References
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- ↑ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.
