Phytol

Phytol
Names
IUPAC names
(2E,7R,11R)-3,7,11,15-
tetramethyl-2-hexadecen-1-ol
Identifiers
7541-49-3 Yes
ChEBI CHEBI:17327 Yes
ChEMBL ChEMBL3039479
ChemSpider 4444094 Yes
Jmol-3D images Image
PubChem 5280435
Properties
Molecular formula
 C20H40O
Molar mass 296.53 g·mol−1
Density 0.850 g cm−3
Boiling point 203 °C (397 °F; 476 K) at 10 mmHg
Except where noted otherwise, data is 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]

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): 881–6. 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] The metabolites phytanic acid and pristanic acid are naturally occurring ligands.[11] In mice oral phytol induces massive proliferation of peroxisomes in several organs.[12]

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.[13]

Commercial applications

Phytol is used in the fragrance industry and used in cosmetics, shampoos, toilet soaps, household cleaners, and detergents.[14] Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.[15]

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. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.