In 2020, Tokyo Smoke, a Canadiancannabis 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 study causing the product removals.[11] In the same year, the Canadian government published an amendment to Canadian cannabis regulations regarding "flavours in cannabis extracts".[12]
Roles in natureedit
Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. phytanic acid) as chemical deterrents against predation.[13] 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.[14][15]
Modulator of transcriptionedit
Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factorsPPAR-alpha[16] and retinoid X receptor (RXR).[17] The metabolites phytanic acid and pristanic acid are naturally occurring ligands.[18] In mice, oral phytol induces massive proliferation of peroxisomes in several organs.[19]
Possible biomedical applicationsedit
Phytol has been investigated for its potential anxiolytic, metabolism-modulating, cytotoxic, antioxidant, autophagy- and apoptosis-inducing, antinociceptive, anti-inflammatory, immune-modulating, and antimicrobial effects.[20]
Geochemical biomarkeredit
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.[21]
^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.
^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.
^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.
^"• Winberry Farms". Archived from the original on 2021-07-21. Retrieved 2019-11-09.
^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. S2CID 39842405.
^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.
^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. doi:10.1080/08958378.2020.1867260. PMID 33441006. Retrieved 26 May 2023.
^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. S2CID 9186973.
^Brown, David (19 July 2021). "Study looking at vape pen ingredient phytol shows serious health concerns". StratCann. Retrieved 29 May 2023.
^"Canada Gazette, Part 1, Volume 155, Number 25". canadagazette.gc.ca. Government of Canada. 19 June 2021. Retrieved 29 May 2023.
^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. S2CID 25886345.
^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. PMC2964658. 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. PMC3571895. 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. PMC275969. 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. Vol. 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.