203 to 204 °C (397 to 399 °F; 476 to 477 K) at 10 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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] In shark liver it yields pristane.
Contents
1Human pathology
2Roles in nature
3Modulator of transcription
4Geochemical biomarker
5Commercial applications
6See also
7References
Human pathology
Refsum disease, an autosomal recessive disorder that results in 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]
See also
Isophytol
Phytantriol
References
^Netscher, Thomas (2007). "Synthesis of Vitamin E". In Litwack, Gerald (ed.). Vitamin E. Vitamins and Hormones. Vitamins & Hormones. 76. pp. 155–202. doi:10.1016/S0083-6729(07)76007-7. ISBN 978-0-12-373592-8. PMID 17628175.
^Daines, Alison; Payne, Richard; Humphries, Mark; Abell, Andrew (2003). "The Synthesis of Naturally Occurring Vitamin K and Vitamin K Analogues". Current Organic Chemistry. 7 (16): 1625–34. doi:10.2174/1385272033486279.
^Van Den Brink, D. M.; Wanders, R. J. A. (2006). "Phytanic acid: Production from phytol, its breakdown and role in human disease". Cellular and Molecular Life Sciences. 63 (15): 1752–65. doi:10.1007/s00018-005-5463-y. PMID 16799769.
^Wierzbicki, A.S. (2007). "Peroxisomal disorders affecting phytanic acid α-oxidation: A review". Biochemical Society Transactions. 35 (5): 881–6. doi:10.1042/BST0350881. PMID 17956237.
^Komen, J.C.; Wanders, R.J.A. (2007). "Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid". Biochemical Society Transactions. 35 (5): 865–9. doi:10.1042/BST0350865. PMID 17956234.
^Brown, P. June; Mei, Guam; Gibberd, F. B.; Burston, D.; Mayne, P. D.; McClinchy, Jane E.; Sidey, Margaret (1993). "Diet and Refsum's disease. The determination of phytanic acid and phytol in certain foods and the application of this knowledge to the choice of suitable convenience foods for patients with Refsum's disease". Journal of Human Nutrition and Dietetics. 6 (4): 295–305. doi:10.1111/j.1365-277X.1993.tb00375.x.
^Vencl, Fredric V.; Morton, Timothy C. (1998). "The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae)". Chemoecology. 8 (1): 25–32. doi:10.1007/PL00001800.
^Watkins, Paul A; Moser, Ann B; Toomer, Cicely B; Steinberg, Steven J; Moser, Hugo W; Karaman, Mazen W; Ramaswamy, Krishna; Siegmund, Kimberly D; Lee, D Rick; Ely, John J; Ryder, Oliver A; Hacia, Joseph G (2010). "Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions". BMC Physiology. 10: 19. doi:10.1186/1472-6793-10-19. PMC 2964658. PMID 20932325.
^Moser, Ann B; Hey, Jody; Dranchak, Patricia K; Karaman, Mazen W; Zhao, Junsong; Cox, Laura A; Ryder, Oliver A; Hacia, Joseph G (2013). "Diverse captive non-human primates with phytanic acid-deficient diets rich in plant products have substantial phytanic acid levels in their red blood cells". Lipids in Health and Disease. 12: 10. doi:10.1186/1476-511X-12-10. PMC 3571895. PMID 23379307.
^Gloerich, J.; Van Vlies, N; Jansen, G. A.; Denis, S; Ruiter, J. P.; Van Werkhoven, M. A.; Duran, M; Vaz, F. M.; Wanders, R. J.; Ferdinandusse, S (2005). "A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPAR -dependent and -independent pathways". The Journal of Lipid Research. 46 (4): 716–26. doi:10.1194/jlr.M400337-JLR200. PMID 15654129.
^Kitareewan, S.; Burka, L. T.; Tomer, K. B.; Parker, C. E.; Deterding, L. J.; Stevens, R. D.; Forman, B. M.; Mais, D. E.; Heyman, R. A.; McMorris, T.; Weinberger, C. (1996). "Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR". Molecular Biology of the Cell. 7 (8): 1153–66. doi:10.1091/mbc.7.8.1153. PMC 275969. PMID 8856661.
^Zomer, Anna W.M.; Van Der Saag, Paul T.; Poll-The, Bwee Tien (2003). "Phytanic and Pristanic Acid Are Naturally Occuring [sic] Ligands". In Roels, Frank; Baes, Myriam; De Bie, Sylvia (eds.). Peroxisomal Disorders and Regulation of Genes. Advances in Experimental Medicine and Biology. 544. pp. 247–54. doi:10.1007/978-1-4419-9072-3_32. ISBN 978-1-4613-4782-8. PMID 14713238.
^Van Den Branden, Christiane; Vamecq, Joseph; Wybo, Ingrid; Roels, Frank (1986). "Phytol and Peroxisome Proliferation". Pediatric Research. 20 (5): 411–5. doi:10.1203/00006450-198605000-00007. PMID 2423950.
^Rontani, Jean-François; Volkman, John K. (2003). "Phytol degradation products as biogeochemical tracers in aquatic environments". Organic Geochemistry. 34 (1): 1–35. doi:10.1016/S0146-6380(02)00185-7.
^McGinty, D.; Letizia, C.S.; Api, A.M. (2010). "Fragrance material review on phytol". Food and Chemical Toxicology. 48: S59–63. doi:10.1016/j.fct.2009.11.012. PMID 20141879.
^IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.
v
t
e
Fatty acid metabolic intermediates
Synthesis
Acetyl-CoA
Malonyl-CoA
Degradation
Acyl-CoA
Acetyl-CoA
Peroxisomal
Phytol
Phytanic acid
Phytanoyl-CoA
Pristanic acid
Propionyl-CoA
Other
Mevalonic acid
Very long chain fatty acid
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… Analysis of the extracts by flame ionization detectorgas chromatography and mass spectrometer-gas chromatography identified 34 components in the oil, of which phytol (34.2%) and (E, E)-α-farnesene (9.5%) were yielded as the principal components. …
How would you define phytol? Add your definition here. Words near phytol in the dictionary phytoherm phytohormone phytohormones phytoid phytol phytolacca phytolacca-americana phytolaccaceae phytolaccas phytolaccinic-acid ...