Phytol

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Phytol
IUPAC name

(2E,7R,11R)-3,7,11,15-
tetramethyl-2-hexadecen-1-ol

Identifiers
CAS number 7541-49-3 YesY
PubChem 5280435
ChemSpider 4444094 YesY
ChEBI CHEBI:17327 YesY
Jmol-3D images {{#if:C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C|Image 1
Properties
Molecular formula C20H40O
Molar mass 296.53 g mol−1
Density 0.850 g cm−3
Boiling point 203 to 204 °C; 397 to 399 °F; 476 to 477 K (10 mmHg)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]

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.<ref name=""pmid17956237">Wierzbicki, A. S. (2007). "Peroxisomal disorders affecting phytanic acid α-oxidation: A review". Biochemical Society Transactions 35 (5): 881–886. doi:10.1042/BST0350881. PMID 17956237. </ref>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.[4] The amount of free phytol in numerous food products has been reported.[5]

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.[6] 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.[7][8]

Modulator of transcription

Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha [9] and retinoid X receptor (RXR).[10]

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.[11]

Commercial applications

Phytol is used in the fragrance industry and used in cosmetics, shampoos, toilet soaps, household cleaners, and detergents.[12] Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.[13]

References

  1. ↑ Netscher, T. 2007. Synthesis of Vitamin E. Vitamins & Hormones. 76, 155-202.
  2. ↑ Daines, A.M. et al. 2003. The synthesis of naturally occurring Vitamin K and Vitamin K analogues. Current Organic Chemistry 7, 1625-1634.
  3. ↑ 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): 1752–1765. doi:10.1007/s00018-005-5463-y. PMID 16799769. 
  4. ↑ Wanders, R. J., Komen, J.C. 2007. Peroxisomes, Refsum's disease and the alpha- and omega-oxidation of phytanic acid. Biochem Soc Trans. 35, 865-869.
  5. ↑ Brown, P. J., Komen et al. 1993. 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, 295-305.
  6. ↑ Venci, F.V. and Morton, T.C. 1998. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology 8, 25-32.
  7. ↑ Watkins, P. A.; Moser, A. B.; Toomer, C. B.; Steinberg, S. J.; Moser, H. W.; Karaman, M. W.; Ramaswamy, K.; Siegmund, K. D.; Lee, D. R.; Ely, J. J.; Ryder, O. A.; Hacia, J. 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. 
  8. ↑ Moser, A. B.; Hey, J.; Dranchak, P. K.; Karaman, M. W.; Zhao, J.; Cox, L. A.; Ryder, O. A.; Hacia, J. 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 (1): 10. doi:10.1186/1476-511X-12-10. PMID 23379307. 
  9. ↑ Gloerich, J., et al. 2005. A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPARalpha-dependent and -independent pathways. Journal of Lipid Research 46, 716-726.
  10. ↑ Kitareewan, S., et al. 1996.Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR. Molecular Biology of the Cell 7, 1153-1166.
  11. ↑ Rontani,J,-F., Volkman, J.K. 2003. Organic Geochemistry. Phytol degradation products as biogeochemical tracers in aquatic environments. 34, 1-35.
  12. ↑ McGinty, D. et al. 2010. Fragrance material review on phytol. Food and Chemical Toxicology 48,S59-S63.
  13. ↑ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.
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