Phytol

Phytol
Names
IUPAC names
(2E,7R,11R)-3,7,11,15-
tetramethyl-2-hexadecen-1-ol
Identifiers
7541-49-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17327 YesY
ChEMBL ChEMBL3039479 N
ChemSpider 4444094 YesY
ECHA InfoCard 100.131.435
PubChem 5280435
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.

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

  1. ↑ Netscher, Thomas (2007). "Synthesis of Vitamin E". In Litwack, Gerald. Vitamin E. Vitamins & Hormones. 76. pp. 155–202. doi:10.1016/S0083-6729(07)76007-7. ISBN 978-0-12-373592-8.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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 2964658Freely accessible. PMID 20932325.
  9. ↑ 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 3571895Freely accessible. PMID 23379307.
  10. ↑ 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.
  11. ↑ 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 275969Freely accessible. PMID 8856661.
  12. ↑ Zomer, Anna W.M.; Van Der Saag, Paul T.; Poll-The, Bwee Tien (2003). "Phytanic and Pristanic Acid Are Naturally Occuring Ligands". In Roels, Frank; Baes, Myriam; De Bie, Sylvia. 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.
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