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			{{Redirect|Florasol|the refrigerant|Florasol 134a}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 444053464
			| Watchedfields = changed
⚫	| Name = Phytol
		⚫	| verifiedrevid = 445213872
	| ImageFile = Phytol.png
	| ImageSize = 244		| Name = Phytol
	| ImageName = Phytol		| ImageFile = Phytol.svg
			| ImageSize = 244
⚫	| IUPACName = (2''E'',7''R'',11''R'')-3,7,11,15-<br />tetramethyl-2-hexadecen-1-ol
		⚫	| ImageName = Phytol
⚫	| Section1 = {{Chembox Identifiers
			| IUPACName = (5''R'',9''R'')-5,6,7,8,9,10,11,12-Octahydro-1,6-secoretinol
⚫	| CASNo = 7541-49-3
		⚫	| SystematicName = (2''E'',7''R'',11''R'')-3,7,11,15-Tetramethylhexadec-2-en-1-ol
⚫	| PubChem = 5280435
		⚫	|Section1={{Chembox Identifiers
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| CASNo_Ref = {{cascite|correct|??}}
		⚫	| CASNo = 150-86-7
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 5BC2RZ81NG
		⚫	| PubChem = 5280435
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4444094		| ChemSpiderID = 4444094
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17327		| ChEBI = 17327
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 3039479
	| SMILES = C(CCC(C)CCC/C(=C/CO)/C)CCCC(C)C		| SMILES = C(CCC(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		| 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		| InChIKey = BOTWFXYSPFMFNR-PYDDKJGSBV
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| 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		| 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_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = BOTWFXYSPFMFNR-PYDDKJGSSA-N		| StdInChIKey = BOTWFXYSPFMFNR-PYDDKJGSSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 20		| C = 20
	| H = 40		| H = 40
	| O = 1		| O = 1
	| Density = 0.850 g cm<sup>−3</sup>		| Density = 0.850 g cm<sup>−3</sup>
	| MeltingPt =		| MeltingPt =
	| BoilingPtCL = 203		| BoilingPtC = 203 to 204
			| BoilingPt_notes = at 10&nbsp;mmHg
	| BoilingPtCH = 204
	| Boiling_notes = 10 mmHg
	}}		}}
	}}		}}
			'''Phytol''' ('''florasol''', '''phytosol''') is an acyclic ] ] ] that is used as a precursor for the manufacture of synthetic forms of ]<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 ],<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> as well as in the ]. Its other commercial uses include ], ]s, ]s, and ]s,<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 ] ]s as a ] or for ].<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> It smells grassy and dominates the aroma of certain green teas.<ref>https://www.cabidigitallibrary.org/doi/full/10.5555/20210258597</ref>{{Failed verification|date=November 2024}}
	'''Phytol''' is an acyclic ] ] that can be used as a precursor for the manufacture of synthetic forms of ]<ref>Netscher, T. 2007. Synthesis of Vitamin E. Vitamins & Hormones. 76, 155-202.</ref> and ].<ref>Daines, A.M. ''et al.'' 2003. The synthesis of naturally occurring Vitamin K and Vitamin K analogues. Current Organic Chemistry 7, 1625-1634.</ref> In ]s, the gut fermentation of ingested plant materials liberates phytol, a constituent of ], which is then converted to ] and stored in fats.<ref>van den Brink, D.M., Wanders, R.J. 2006. Phytanic acid: production from phytol, its breakdown and role in human disease. Cell Mol Life Sci. 63,1752-1765.</ref>
		⚫	Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.<ref>IFRA (]), 2004. Use Level Survey, August 2004.</ref>
	==Human pathology==
			==Pharmacology==
⚫	], an autosomal recessive disorder that results from the accumulation of large stores of phytanic acid in tissues, frequently manifests ], ], ], ], and hearing loss.<ref>Wierzbicki, A.S. 2007. Peroxisomal disorders affecting phytanic acid alpha-oxidation: a review. Biochem Soc Trans 35, 881-886.</ref> Although humans cannot derive ] from ], they can convert free phytol into ]. Thus, patients with ] should limit their intake of ] and free phytol.<ref>Wanders, R. J., Komen, J.C. 2007. Peroxisomes, Refsum's disease and the alpha- and omega-oxidation of phytanic acid. Biochem Soc Trans. 35, 865-869.</ref> The amount of free phytol in numerous food products has been reported.<ref>Brown, P. J., Komen ''et al.'' 1993. 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, 295-305.</ref>
			===Humans===
		⚫	] (also known as adult Refsum disease) is an autosomal recessive disorder that results in the accumulation of toxic stores of ] in tissues and frequently manifests as a variable combination of ], ], ], ], 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> Although humans cannot derive phytanic acid from ], they can convert free phytol into phytanic acid. Thus, patients with Refsum disease should limit their intake of phytanic acid and free phytol.<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> The amount of free phytol in numerous food products has been reported.<ref>{{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>
			===Rats===
			Phytol was found to cause ] and ] of ], ] and ] ] when exposed in ] to ] ]s, with no ] being established. A majority of the phytol rats turned out dead or ], 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 |url=https://pubmed.ncbi.nlm.nih.gov/33441006/ |journal=Inhalation Toxicology |access-date=26 May 2023 |pages=33–40 |doi=10.1080/08958378.2020.1867260 |date=January 2021|volume=33 |issue=1 |pmid=33441006 |bibcode=2021InhTx..33...33S }}</ref>
			===Other vertebrates===
			In ]s, 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>
			In ] ] it yields ].
			==History==
			===Controversy===
			In 2020, ], a ] ] owned by ] 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 ] of True Terpenes, a company that still listed it as a product; along with Andrew Freedman, investigated the matter, filing a request under the ] to unredact the ] 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 ] published an ] to ] 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>
	==Roles in nature==		==Roles in nature==
	Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. ]) as chemical deterrents against predation.<ref>Venci, F.V. and Morton, T.C. 1998. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology 8, 25-32.</ref> These compounds originate from host plants.		Insects, such as the ], 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.
			Indirect evidence has been provided that, in contrast to humans, diverse ]s can derive significant amounts of phytol from the ] 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 |pages=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 |pages=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>
	Indirect evidence has been provided that the ] (], ], ], and ]), in contrast to humans, derive significant amounts of phytol, which is then converted to ], from the hindgut fermentation of plant materials.<ref>Watkins, P.A., ''et al.'' 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.</ref>
	==Modulator of transcription==		==Modulator of transcription==
			Phytol and/or its metabolites have been reported to bind to and/or activate the ] ]<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 ] (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 ] 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 }} 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 ]s 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>
	Phytol and/or its metabolites have been reported to bind to and/or activate the ] ] <ref>Gloerich, J., ''et al.'' 2005. A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPARalpha-dependent and -independent pathways. Journal of Lipid Research 46, 716-726.</ref> and ] (RXR).<ref>Kitareewan, S., ''et al.'' 1996.Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR. Molecular Biology of the Cell 7, 1153-1166.</ref>
		⚫	==Possible biomedical applications==
			Phytol has been investigated for its potential ], metabolism-modulating, ], antioxidant, ]- and ]-inducing, ], 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>
	==Geochemical biomarker==		==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.<ref>Rontani,J,-F., Volkman, J.K. 2003. Organic Geochemistry. Phytol degradation products as biogeochemical tracers in		Phytol is likely the most abundant acyclic ] compound present in the biosphere and its degradation products have been used as biogeochemical tracers in aquatic environments.<ref>{{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>
	aquatic environments. 34, 1-35.</ref>
			==See also==
⚫	==Commercial applications==
			* ]
⚫	Phytol is used in the fragrance industry and used in cosmetics, shampoos, toilet soaps, household cleaners, and detergents.<ref>McGinty, D. ''et. al.'' 2010. Fragrance material review on phytol. Food and Chemical Toxicology 48,S59-S63.</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>
			* ]
	==References==		==References==
	{{reflist}}		{{reflist}}
			{{Fatty-acid metabolism intermediates}}
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