{{Redirect|Florasol|the refrigerant|Florasol 134a}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 445213872 | Name = Phytol | ImageFile = Phytol.svg | ImageSize = 244 | ImageName = Phytol | IUPACName = (5''R'',9''R'')-5,6,7,8,9,10,11,12-Octahydro-1,6-secoretinol | SystematicName = (2''E'',7''R'',11''R'')-3,7,11,15-Tetramethylhexadec-2-en-1-ol |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 150-86-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 5BC2RZ81NG | PubChem = 5280435 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4444094 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 17327 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 3039479 | SMILES = C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C | 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 | InChIKey = BOTWFXYSPFMFNR-PYDDKJGSBV | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI =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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BOTWFXYSPFMFNR-PYDDKJGSSA-N }} |Section2={{Chembox Properties | C = 20 | H = 40 | O = 1 | Density = 0.850 g cm<sup>−3</sup> | MeltingPt = | BoilingPtC = 203 to 204 | BoilingPt_notes = at 10 mmHg }} }}
'''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.<ref name=Gutbrod19>{{cite journal |last1=Gutbrod |first1=Katharina |last2=Romer |first2=Jill |last3=Dörmann |first3=Peter |title=Phytol metabolism in plants |journal=Progress in Lipid Research |date=April 2019 |volume=74 |pages=1–17 |doi=10.1016/j.plipres.2019.01.002}}</ref> It smells grassy and dominates the aroma of certain green teas.<ref name=CABI>{{Cite web | url=https://www.cabidigitallibrary.org/doi/full/10.5555/20210258597 | title=Analysis of volatile aroma compounds...}}{{Dead link | date=August 2025 | fix-attempted=yes}}</ref>
In human industry, phytol can be used to chemically synthesize vitamins E<ref>{{cite book |doi=10.1016/S0083-6729(07)76007-7 |pmid=17628175 |chapter=Synthesis of Vitamin E |pages=155–202 |editor1-first=Gerald |editor1-last=Litwack |title=Vitamin E |volume=76 |series=Vitamins & Hormones |year=2007 |last1=Netscher |first1=Thomas |isbn=978-0-12-373592-8}}</ref> and K1.<ref>{{cite journal |doi=10.2174/1385272033486279 |title=The Synthesis of Naturally Occurring Vitamin K and Vitamin K Analogues |journal=Current Organic Chemistry |volume=7 |issue=16 |pages=1625–34 |year=2003 |last1=Daines |first1=Alison |last2=Payne |first2=Richard |last3=Humphries |first3=Mark |last4=Abell |first4=Andrew |url=http://sydney.edu.au/science/chemistry/~payne/COCvitaminKreview.pdf }}</ref> It is also used as a fragrance and flavoring in cosmetics, shampoos, toilet soaps, and detergents,<ref>{{cite journal |doi=10.1016/j.fct.2009.11.012 |pmid=20141879 |title=Fragrance material review on phytol |journal=Food and Chemical Toxicology |volume=48 |pages=S59–63 |year=2010 |last1=McGinty |first1=D. |last2=Letizia |first2=C.S. |last3=Api |first3=A.M. }}</ref> as well as in some cannabis distillates as a diluent or for flavoring.<ref>{{cite web |url=https://winberryfarms.com/winberry-farms-product-update-on-vape-quality-2/ |title=• Winberry Farms |access-date=2019-11-09 |archive-date=2021-07-21 |archive-url=https://web.archive.org/web/20210721142511/https://winberryfarms.com/winberry-farms-product-update-on-vape-quality-2/ |url-status=dead }}</ref>
Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.<ref>IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.</ref>
==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.<ref name=Gutbrod19/> Older theories of chlorophyll synthesis instead holds that the chlorophyll synthase directly acts on a chlorophyllide and a phytyl pyrophosphate (phytyl-PP),<ref>{{cite journal |doi= 10.1515/BC.2002.198 |title= Pre-Loading of Chlorophyll Synthase with Tetraprenyl Diphosphate is an Obligatory Step in Chlorophyll Biosynthesis |year= 2002 |last1= Schmid |first1= H. C. |last2= Rassadina |first2= V. |last3= Oster |first3= U. |last4= Schoch |first4= S. |last5= Rüdiger |first5= W. |journal= Biological Chemistry |volume= 383 |issue= 11 |pages= 1769–78 |pmid= 12530542 |s2cid= 3099209 |url= https://epub.ub.uni-muenchen.de/17847/1/bc.2002.198.pdf }}</ref> 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''.<ref name=Gutbrod19/>
Phytol, or more precisely phytyl-PP, is used to build vitamin E (tocotrienol, tocopherol) and vitamin K1 (the reduced form, phylloquinol) in the chloroplast.<ref name=Gutbrod19/> 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.<ref name=Basset2017>{{cite journal | vauthors = Basset GJ, Latimer S, Fatihi A, Soubeyrand E, Block A | title = Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions | journal = Mini Reviews in Medicinal Chemistry | volume = 17 | issue = 12 | pages = 1028–1038 | date = 2017 | pmid = 27337968 | doi = 10.2174/1389557516666160623082714 }}</ref>
=== 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.<ref>{{cite journal |doi=10.1007/PL00001800 |title=The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae) |journal=Chemoecology |volume=8 |issue=1 |pages=25–32 |year=1998 |last1=Vencl |first1=Fredric V. |last2=Morton |first2=Timothy C. |bibcode=1998Checo...8...25V |s2cid=25886345 }}</ref> 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.<ref name="pmid16799769">{{cite journal |doi=10.1007/s00018-005-5463-y |pmid=16799769 |title=Phytanic acid: Production from phytol, its breakdown and role in human disease |journal=Cellular and Molecular Life Sciences |volume=63 |issue=15 |pages=1752–65 |year=2006 |last1=Van Den Brink |first1=D. M. |last2=Wanders |first2=R. J. A. |s2cid=9186973 |pmc=11136310 }}</ref>
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.<ref name="pmid20932325">{{cite journal |doi=10.1186/1472-6793-10-19 |pmid=20932325 |pmc=2964658 |title=Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions |journal=BMC Physiology |volume=10 |article-number=19 |year=2010 |last1=Watkins |first1=Paul A |last2=Moser |first2=Ann B |last3=Toomer |first3=Cicely B |last4=Steinberg |first4=Steven J |last5=Moser |first5=Hugo W |last6=Karaman |first6=Mazen W |last7=Ramaswamy |first7=Krishna |last8=Siegmund |first8=Kimberly D |last9=Lee |first9=D Rick |last10=Ely |first10=John J |last11=Ryder |first11=Oliver A |last12=Hacia |first12=Joseph G |doi-access=free }}</ref><ref name="pmid23379307">{{cite journal |doi=10.1186/1476-511X-12-10 |pmid=23379307 |pmc=3571895 |title=Diverse captive non-human primates with phytanic acid-deficient diets rich in plant products have substantial phytanic acid levels in their red blood cells |journal=Lipids in Health and Disease |volume=12 |article-number=10 |year=2013 |last1=Moser |first1=Ann B |last2=Hey |first2=Jody |last3=Dranchak |first3=Patricia K |last4=Karaman |first4=Mazen W |last5=Zhao |first5=Junsong |last6=Cox |first6=Laura A |last7=Ryder |first7=Oliver A |last8=Hacia |first8=Joseph G |doi-access=free }}</ref>
===== Modulator of transcription ===== Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha<ref>{{cite journal |doi=10.1194/jlr.M400337-JLR200 |pmid=15654129 |title=A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPAR -dependent and -independent pathways |journal=The Journal of Lipid Research |volume=46 |issue=4 |pages=716–26 |year=2005 |last1=Gloerich |first1=J. |last2=Van Vlies |first2=N |last3=Jansen |first3=G. A. |last4=Denis |first4=S |last5=Ruiter |first5=J. P. |last6=Van Werkhoven |first6=M. A. |last7=Duran |first7=M |last8=Vaz |first8=F. M. |last9=Wanders |first9=R. J. |last10=Ferdinandusse |first10=S |doi-access=free }}</ref> and retinoid X receptor (RXR).<ref>{{cite journal |doi=10.1091/mbc.7.8.1153 |pmid=8856661 |pmc=275969 |title=Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR |journal=Molecular Biology of the Cell |volume=7 |issue=8 |pages=1153–66 |year=1996 |last1=Kitareewan |first1=S. |last2=Burka |first2=L. T. |last3=Tomer |first3=K. B. |last4=Parker |first4=C. E. |last5=Deterding |first5=L. J. |last6=Stevens |first6=R. D. |last7=Forman |first7=B. M. |last8=Mais |first8=D. E. |last9=Heyman |first9=R. A. |last10=McMorris |first10=T. |last11=Weinberger |first11=C. }}</ref> The metabolites phytanic acid and pristanic acid are naturally occurring ligands.<ref>{{cite book |doi=10.1007/978-1-4419-9072-3_32 |pmid=14713238 |last1=Zomer |first1=Anna W.M. |last2=Van Der Saag |first2=Paul T. |last3=Poll-The |first3=Bwee Tien |year=2003 |chapter=Phytanic and Pristanic Acid Are Naturally {{as written|Occ|uring [sic]}} Ligands |pages=247–54 |editor1-first=Frank |editor1-last=Roels |editor2-first=Myriam |editor2-last=Baes |editor3-first=Sylvia |editor3-last=De Bie |title=Peroxisomal Disorders and Regulation of Genes |volume=544 |series=Advances in Experimental Medicine and Biology |isbn=978-1-4613-4782-8 }}</ref> In mice, oral phytol induces massive proliferation of peroxisomes in several organs.<ref>{{cite journal |doi=10.1203/00006450-198605000-00007 |pmid=2423950 |title=Phytol and Peroxisome Proliferation |journal=Pediatric Research |volume=20 |issue=5 |pages=411–5 |year=1986 |last1=Van Den Branden |first1=Christiane |last2=Vamecq |first2=Joseph |last3=Wybo |first3=Ingrid |last4=Roels |first4=Frank |doi-access=free }}</ref>
==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.<ref>{{cite journal |last1=Islam |first1=MT |last2=Ali |first2=ES |last3=Uddin |first3=SJ |last4=Shaw |first4=S |last5=Islam |first5=MA |last6=Ahmed |first6=MI |last7=Chandra Shill |first7=M |last8=Karmakar |first8=UK |last9=Yarla |first9=NS |last10=Khan |first10=IN |last11=Billah |first11=MM |last12=Pieczynska |first12=MD |last13=Zengin |first13=G |last14=Malainer |first14=C |last15=Nicoletti |first15=F |last16=Gulei |first16=D |last17=Berindan-Neagoe |first17=I |last18=Apostolov |first18=A |last19=Banach |first19=M |last20=Yeung |first20=AWK |last21=El-Demerdash |first21=A |last22=Xiao |first22=J |last23=Dey |first23=P |last24=Yele |first24=S |last25=Jóźwik |first25=A |last26=Strzałkowska |first26=N |last27=Marchewka |first27=J |last28=Rengasamy |first28=KRR |last29=Horbańczuk |first29=J |last30=Kamal |first30=MA |last31=Mubarak |first31=MS |last32=Mishra |first32=SK |last33=Shilpi |first33=JA |last34=Atanasov |first34=AG |title=Phytol: A review of biomedical activities. |journal=Food and Chemical Toxicology |date=November 2018 |volume=121 |pages=82–94 |doi=10.1016/j.fct.2018.08.032 |pmid=30130593|hdl=2328/39143 |s2cid=52055348 |hdl-access=free }}</ref>
== Toxicology ==
=== Oral: refsum disease === Free phytol is converted by humans into phytanic acid, a natural compound also found in ruminant meat.<ref>{{cite journal |doi=10.1042/BST0350865 |pmid=17956234 |title=Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid |journal=Biochemical Society Transactions |volume=35 |issue=5 |pages=865–9 |year=2007 |last1=Komen |first1=J.C. |last2=Wanders |first2=R.J.A. |s2cid=39842405 }}</ref> 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.<ref name="pmid17956237">{{cite journal |doi=10.1042/BST0350881 |pmid=17956237 |title=Peroxisomal disorders affecting phytanic acid α-oxidation: A review |journal=Biochemical Society Transactions |volume=35 |issue=5 |pages=881–6 |year=2007 |last1=Wierzbicki |first1=A.S. }}</ref> 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.<ref name=Brown93/>
A list of free phytol content in various convenience store foods is available.<ref name=Brown93>{{cite journal |doi=10.1111/j.1365-277X.1993.tb00375.x |title=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=Journal of Human Nutrition and Dietetics |volume=6 |issue=4 |pages=295–305 |year=1993 |last1=Brown |first1=P. June |last2=Mei |first2=Guam |last3=Gibberd |first3=F. B. |last4=Burston |first4=D. |last5=Mayne |first5=P. D. |last6=McClinchy |first6=Jane E. |last7=Sidey |first7=Margaret }}</ref>
=== Inhalation === {{anchor|Rats}}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.<ref>{{cite journal |last1=Schwotzer |first1=Daniela |last2=Gigliotti |first2=Andrew |last3=Irshad |first3=Hammad |last4=Dye |first4=Wendy |last5=McDonald |first5=Jacob |title=Phytol, not propylene glycol, causes severe pulmonary injury after inhalation dosing in Sprague-Dawley rats |journal=Inhalation Toxicology |pages=33–40 |doi=10.1080/08958378.2020.1867260 |date=January 2021|volume=33 |issue=1 |pmid=33441006 |bibcode=2021InhTx..33...33S }}</ref>
====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.<ref>{{cite web |last1=Brown |first1=David |title=Study looking at vape pen ingredient phytol shows serious health concerns |url=https://stratcann.com/insight/study-look-at-vape-pen-ingredient-phytol-shows-serious-health-concerns/ |website=StratCann |access-date=29 May 2023 |date=19 July 2021}}</ref> In the same year, the Canadian government published an amendment to Canadian cannabis regulations regarding "flavours in cannabis extracts".<ref>{{cite web |title=Canada Gazette, Part 1, Volume 155, Number 25 |url=https://canadagazette.gc.ca/rp-pr/p1/2021/2021-06-19/html/reg4-eng.html |website=canadagazette.gc.ca |publisher=Government of Canada |access-date=29 May 2023 |language=Canadian English |date=19 June 2021}}</ref>
==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.<ref name=Rontani03>{{cite journal |doi=10.1016/S0146-6380(02)00185-7 |title=Phytol degradation products as biogeochemical tracers in aquatic environments |journal=Organic Geochemistry |volume=34 |issue=1 |pages=1–35 |year=2003 |last1=Rontani |first1=Jean-François |last2=Volkman |first2=John K. |bibcode=2003OrGeo..34....1R }}</ref> 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.<ref name=Rontani03/>
An example of this use of phytol is in the estimation of carbon isotopic fractionation during photosynthesis by Rubisco using ancient sediments.<ref>{{cite journal |last1=Graham |first1=Olivia A. |last2=Witkowski |first2=Caitlyn R. |last3=Stevenson |first3=Mark A. |last4=Peterse |first4=Francien |last5=Naafs |first5=B. David A. |title=A phytol εp-based core-top calibration to reconstruct past changes in atmospheric CO2 |journal=Geochimica et Cosmochimica Acta |date=June 2025 |volume=398 |pages=178–192 |doi=10.1016/j.gca.2025.04.014}}</ref>
==See also== * Isophytol * Phytantriol
==References== {{reflist}}
{{Fatty-acid metabolism intermediates}} {{Terpenoids}}
Category:Primary alcohols Category:Diterpenes Category:Alkene derivatives