fbpx
Wikipedia

Phytol

February 16, 2024

"Florasol" redirects here. For the refrigerant, see Florasol 134a.

Phytol (florasol, phytosol) is an acyclic hydrogenated diterpene alcohol that is used as a precursor for the manufacture of synthetic forms of vitamin E[1] and vitamin K1,[2] as well as in the fragrance industry. Its other commercial uses include cosmetics, shampoos, toilet soaps, and detergents,[3] as well as in some cannabis distillates as a diluent or for flavoring.[4] Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.[5]

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
  • 150-86-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17327 Y
ChEMBL
  • ChEMBL3039479 N
ChemSpider
  • 4444094 Y
ECHA InfoCard 100.131.435
  • 5280435
UNII
  • 5BC2RZ81NG Y
  • DTXSID1040586
  • 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 Y
    Key: BOTWFXYSPFMFNR-PYDDKJGSSA-N Y
  • 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 YN ?)

Pharmacology edit

Humans edit

Refsum disease (also known as adult Refsum disease) is an autosomal recessive disorder that results in the accumulation of toxic stores of phytanic acid in tissues and frequently manifests as a variable combination of peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss.[6] 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.[7] The amount of free phytol in numerous food products has been reported.[8]

Rats edit

It 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.[9]

Other vertebrates edit

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.[10] In shark liver it yields pristane.

History edit

Controversy edit

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 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 nature edit

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 transcription edit

Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-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 applications edit

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 biomarker edit

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]

See also edit

References edit

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ . Archived from the original on 2021-07-21. Retrieved 2019-11-09.
  5. ^ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ Brown, David (19 July 2021). "Study looking at vape pen ingredient phytol shows serious health concerns". StratCann. Retrieved 29 May 2023.
  12. ^ "Canada Gazette, Part 1, Volume 155, Number 25". canadagazette.gc.ca. Government of Canada. 19 June 2021. Retrieved 29 May 2023.
  13. ^ 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.
  14. ^ 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.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
  18. ^ 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.
  19. ^ 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.
  20. ^ 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.
  21. ^ 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.

February 16, 2024
phytol, florasol, redirects, here, refrigerant, florasol, 134a, florasol, phytosol, acyclic, hydrogenated, diterpene, alcohol, that, used, precursor, manufacture, synthetic, forms, vitamin, vitamin, well, fragrance, industry, other, commercial, uses, include, . Florasol redirects here For the refrigerant see Florasol 134a Phytol florasol phytosol is an acyclic hydrogenated diterpene alcohol that is used as a precursor for the manufacture of synthetic forms of vitamin E 1 and vitamin K1 2 as well as in the fragrance industry Its other commercial uses include cosmetics shampoos toilet soaps and detergents 3 as well as in some cannabis distillates as a diluent or for flavoring 4 Its worldwide use has been estimated to be approximately 0 1 1 0 metric tons per year 5 Phytol NamesIUPAC name 5R 9R 5 6 7 8 9 10 11 12 Octahydro 1 6 secoretinolSystematic IUPAC name 2E 7R 11R 3 7 11 15 Tetramethylhexadec 2 en 1 olIdentifiersCAS Number 150 86 7 Y3D model JSmol Interactive imageChEBI CHEBI 17327 YChEMBL ChEMBL3039479 NChemSpider 4444094 YECHA InfoCard 100 131 435PubChem CID 5280435UNII 5BC2RZ81NG YCompTox Dashboard EPA DTXSID1040586InChI 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 YKey BOTWFXYSPFMFNR PYDDKJGSSA N YInChI 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 s1Key BOTWFXYSPFMFNR PYDDKJGSBVSMILES C C H CCC C H C CCC C C CO C CCCC C CPropertiesChemical formula C 20H 40OMolar mass 296 539 g mol 1Density 0 850 g cm 3Boiling point 203 to 204 C 397 to 399 F 476 to 477 K at 10 mmHgExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Pharmacology 1 1 Humans 1 2 Rats 1 3 Other vertebrates 2 History 2 1 Controversy 3 Roles in nature 4 Modulator of transcription 5 Possible biomedical applications 6 Geochemical biomarker 7 See also 8 ReferencesPharmacology editHumans edit Refsum disease also known as adult Refsum disease is an autosomal recessive disorder that results in the accumulation of toxic stores of phytanic acid in tissues and frequently manifests as a variable combination of peripheral polyneuropathy cerebellar ataxia retinitis pigmentosa anosmia and hearing loss 6 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 7 The amount of free phytol in numerous food products has been reported 8 Rats edit It 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 9 Other vertebrates edit 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 10 In shark liver it yields pristane History editControversy edit 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 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 nature editInsects 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 transcription editPhytol and or its metabolites have been reported to bind to and or activate the transcription factors PPAR 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 applications editPhytol 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 biomarker editPhytol 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 See also editIsophytol PhytantriolReferences edit Netscher Thomas 2007 Synthesis of Vitamin E In Litwack Gerald ed Vitamin E Vitamins amp 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 IFRA International Fragrance Association 2004 Use Level Survey August 2004 Wierzbicki A S 2007 Peroxisomal disorders affecting phytanic acid a 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 a and w 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 PMC 2964658 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 PMC 3571895 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 PMC 275969 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 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 Jozwik A Strzalkowska N Marchewka J Rengasamy KRR Horbanczuk 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 Rontani Jean Francois 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 Retrieved from https en wikipedia org w index php title Phytol amp oldid 1181978236, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.