Difference between revisions of "Phytol"

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{{wikipedia::Phytol}}
{{wikipedia::Phytol}}
==Notes==
==Notes==
This article is a direct transclusion of [https://en.wikipedia.org/wiki/Phytol the Wikipedia article] and therefore may not meet the same editing standards as CannabisQAwiki.
This article is a direct transclusion of [https://en.wikipedia.org/wiki/Phytol the Wikipedia article] and therefore may not meet the same editing standards as LIMSwiki.


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Latest revision as of 22:25, 28 February 2024

"Florasol" redirects here. For the refrigerant, see Florasol 134a.
Phytol
Phytol
Phytol
Names
IUPAC name
(5R,9R)-5,6,7,8,9,10,11,12-Octahydro-1,6-secoretinol
Systematic IUPAC name
(2E,7R,11R)-3,7,11,15-Tetramethylhexadec-2-en-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.131.435 Edit this at Wikidata
UNII
  • InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1 checkY
    Key: BOTWFXYSPFMFNR-PYDDKJGSSA-N checkY
  • InChI=1/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1
    Key: BOTWFXYSPFMFNR-PYDDKJGSBV
  • C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C
Properties
C20H40O
Molar mass 296.539 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 checkY☒N ?)

Phytol (florasol, phytosol) is an acyclic hydrogenated diterpene alcohol. It is naturally found in many plants as a result of chlorophyll degredation and is used by them to produce vitamin E and vitamin K1.[1] It smells grassy and dominates the aroma of certain green teas.[2]

In human industry, phytol can be used to chemically synthesize vitamins E[3] and K1.[4] It is also used as a fragrance and flavoring in cosmetics, shampoos, toilet soaps, and detergents,[5] as well as in some cannabis distillates as a diluent or for flavoring.[6]

Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.[7]

Roles in nature

Plants

Phytol is mainly produced by plants from chlorophyll degredation. In the biosynthesis of chlorophyll in the mouse-ear cress chloroplast, the chlorophyll synthase attaches a chlorophyllide ring to geranylgeranyl pyrophosphate (GGPP). Two steps of reduction then convert the GG tail into a phytyl tail. When this phytyl tail is hydrolyzed off, it becomes phytol.[1] Older theories of chlorophyll synthesis instead holds that the chlorophyll synthase directly acts on a chlorophyllide and a phytyl pyrophosphate (phytyl-PP),[8] with the phytyl-PP directly produced by reduction of GGPP. Although this can happen using isolated enzymes in vitro, there is little evidence for this happening in vivo.[1]

Phytol, or more precisely phytyl-PP, is used to build vitamin E (tocotrienol, tocopherol) and vitamin K1 (the reduced form, phylloquinol) in the chloroplast.[1] The former protects the plant against oxidative stress and the latter acts as an essential part of the Photosystem I electron transport chain, without which photosynthesis cannot occur.[9]

Invertebrates

Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. phytanic acid) as chemical deterrents against predation.[10] These compounds originate from host plants.

Vertebrates

In shark liver it is converted to pristane.

Mammals

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.[11]

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.[12][13]

Modulator of transcription

Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha[14] and retinoid X receptor (RXR).[15] The metabolites phytanic acid and pristanic acid are naturally occurring ligands.[16] In mice, oral phytol induces massive proliferation of peroxisomes in several organs.[17]

Possible biomedical applications

Phytol has been investigated for its potential anxiolytic, metabolism-modulating, cytotoxic, antioxidant, autophagy- and apoptosis-inducing, antinociceptive, anti-inflammatory, immune-modulating, and antimicrobial effects.[18]

Toxicology

Oral: refsum disease

Free phytol is converted by humans into phytanic acid, a natural compound also found in ruminant meat.[19] Phytanic acid is dangerous for people with the autosomal recessive disorder Refsum disease (also known as adult Refsum disease), in which genetic changes renders them unable to break down this fatty acid and frequently manifests as a variable combination of peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss.[20] As a result, those suffering from this illness should avoid both free phytol and phytanic acid. They do not need to avoid chlorophyll as the human digestive system cannot effectively cleave off the phytol sidechain of chlorophyll.[21]

A list of free phytol content in various convenience store foods is available.[21]

Inhalation

In 2021, phytol was found to cause pulmonary hemorrhage and necrosis of nose, throat and lung tissue when exposed in aerosol to Sprague Dawley rats, with no safe dose range being established. A majority of the phytol rats turned out dead or moribund, leading to 2nd-day termination of the 14-day study.[22]

Vape controversy

In 2020, Tokyo Smoke, a Canadian cannabis company owned by Canopy Growth at the time; pulled every phytol-containing product from their shelves and issued a 48 hour deadline to suppliers, demanding 'written confirmation' if it was included. A year later, David Heldreth, a former CSO of True Terpenes, a company that still listed it as a product; along with Andrew Freedman, investigated the matter, filing a request under the Access to Information Act to unredact the Health Canada study causing the product removals.[23] In the same year, the Canadian government published an amendment to Canadian cannabis regulations regarding "flavours in cannabis extracts".[24]

Geochemical biomarker

Phytol has been described as "perhaps the most studied biomarker of those found in modern aquatic environments" in the context of biogeochemical tracers in aquatic environments. It is likely the most abundant acyclic isoprenoid compound present in the biosphere, being the ester sidechain of chlorophyll-a,b,c and bacteriochlorophyll-a (altogether produced by plants, algae, and many photosynthetic bacteria). It is degraded into a wide variety of products, including phytone, phytyldiol, dihydrophytol, pristane and many others, by biological and geological means.[25] Some of these products such as pristane can be produced by other processes (such as oil spills) and are unusuable as a marker related to photosynthesis, while others such as dihydrophytol appear quite selective.[25]

An example of this use of phytol is in the estimation of carbon isotopic fractionation during photosynthesis by Rubisco using ancient sediments.[26]

See also

References

  1. ^ a b c d Gutbrod, Katharina; Romer, Jill; Dörmann, Peter (April 2019). "Phytol metabolism in plants". Progress in Lipid Research. 74: 1–17. doi:10.1016/j.plipres.2019.01.002.
  2. ^ "Analysis of volatile aroma compounds..."[permanent dead link]
  3. ^ Netscher, Thomas (2007). "Synthesis of Vitamin E". In Litwack, Gerald (ed.). Vitamin E. Vitamins & Hormones. Vol. 76. pp. 155–202. doi:10.1016/S0083-6729(07)76007-7. ISBN 978-0-12-373592-8. PMID 17628175.
  4. ^ Daines, Alison; Payne, Richard; Humphries, Mark; Abell, Andrew (2003). "The Synthesis of Naturally Occurring Vitamin K and Vitamin K Analogues" (PDF). Current Organic Chemistry. 7 (16): 1625–34. doi:10.2174/1385272033486279.
  5. ^ 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.
  6. ^ "• Winberry Farms". Archived from the original on 2021-07-21. Retrieved 2019-11-09.
  7. ^ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.
  8. ^ Schmid, H. C.; Rassadina, V.; Oster, U.; Schoch, S.; Rüdiger, W. (2002). "Pre-Loading of Chlorophyll Synthase with Tetraprenyl Diphosphate is an Obligatory Step in Chlorophyll Biosynthesis" (PDF). Biological Chemistry. 383 (11): 1769–78. doi:10.1515/BC.2002.198. PMID 12530542. S2CID 3099209.
  9. ^ Basset GJ, Latimer S, Fatihi A, Soubeyrand E, Block A (2017). "Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions". Mini Reviews in Medicinal Chemistry. 17 (12): 1028–1038. doi:10.2174/1389557516666160623082714. PMID 27337968.
  10. ^ Vencl, Fredric V.; Morton, Timothy C. (1998). "The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae)". Chemoecology. 8 (1): 25–32. Bibcode:1998Checo...8...25V. doi:10.1007/PL00001800. S2CID 25886345.
  11. ^ 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. PMC 11136310. PMID 16799769. S2CID 9186973.
  12. ^ 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.
  13. ^ 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.
  14. ^ 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.
  15. ^ 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.
  16. ^ 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. Vol. 544. pp. 247–54. doi:10.1007/978-1-4419-9072-3_32. ISBN 978-1-4613-4782-8. PMID 14713238.
  17. ^ 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.
  18. ^ Islam, MT; Ali, ES; Uddin, SJ; Shaw, S; Islam, MA; Ahmed, MI; Chandra Shill, M; Karmakar, UK; Yarla, NS; Khan, IN; Billah, MM; Pieczynska, MD; Zengin, G; Malainer, C; Nicoletti, F; Gulei, D; Berindan-Neagoe, I; Apostolov, A; Banach, M; Yeung, AWK; El-Demerdash, A; Xiao, J; Dey, P; Yele, S; Jóźwik, A; Strzałkowska, N; Marchewka, J; Rengasamy, KRR; Horbańczuk, J; Kamal, MA; Mubarak, MS; Mishra, SK; Shilpi, JA; Atanasov, AG (November 2018). "Phytol: A review of biomedical activities". Food and Chemical Toxicology. 121: 82–94. doi:10.1016/j.fct.2018.08.032. hdl:2328/39143. PMID 30130593. S2CID 52055348.
  19. ^ 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. S2CID 39842405.
  20. ^ 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.
  21. ^ a b 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.
  22. ^ Schwotzer, Daniela; Gigliotti, Andrew; Irshad, Hammad; Dye, Wendy; McDonald, Jacob (January 2021). "Phytol, not propylene glycol, causes severe pulmonary injury after inhalation dosing in Sprague-Dawley rats". Inhalation Toxicology. 33 (1): 33–40. Bibcode:2021InhTx..33...33S. doi:10.1080/08958378.2020.1867260. PMID 33441006.
  23. ^ Brown, David (19 July 2021). "Study looking at vape pen ingredient phytol shows serious health concerns". StratCann. Retrieved 29 May 2023.
  24. ^ "Canada Gazette, Part 1, Volume 155, Number 25". canadagazette.gc.ca. Government of Canada. 19 June 2021. Retrieved 29 May 2023.
  25. ^ a b Rontani, Jean-François; Volkman, John K. (2003). "Phytol degradation products as biogeochemical tracers in aquatic environments". Organic Geochemistry. 34 (1): 1–35. Bibcode:2003OrGeo..34....1R. doi:10.1016/S0146-6380(02)00185-7.
  26. ^ Graham, Olivia A.; Witkowski, Caitlyn R.; Stevenson, Mark A.; Peterse, Francien; Naafs, B. David A. (June 2025). "A phytol εp-based core-top calibration to reconstruct past changes in atmospheric CO2". Geochimica et Cosmochimica Acta. 398: 178–192. doi:10.1016/j.gca.2025.04.014.

Notes

This article is a direct transclusion of the Wikipedia article and therefore may not meet the same editing standards as LIMSwiki.

Retrieved from "https://www.limswiki.org/index.php?title=Phytol&oldid=58380"