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{{chembox
{{chembox
| verifiedrevid = 436078588
| Watchedfields = changed
| verifiedrevid = 410599138
| ImageFile = Phytanic acid.png
| ImageFile = Phytanic acid.png
| ImageSize = 250px
| ImageSize = 250px
| IUPACName = (''7R,11R'')-3,7,11,15-Tetramethylhexadecanoic acid
| IUPACName = (''7R,11R'')-3,7,11,15-Tetramethylhexadecanoic acid
| OtherNames = phytanoic acid
| OtherNames = phytanoic acid
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 14721-66-5
| PubChem = 468706
| =
| UNII_Ref = {{fdacite|correct|FDA}}
| SMILES = CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CC(=O)O
| UNII = 8OYE5TF5VL
| MeSHName = Phytanic+acid
| PubChem = 468706
| SMILES = CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CC(=O)O
| MeSHName = Phytanic+acid
| ChemSpiderID = 411797
| StdInChI = 1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19?/m1/s1
| StdInChIKey = RLCKHJSFHOZMDR-PWCSWUJKSA-N

}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C = 20
| C =
| H = 40
| =
| O = 2
| =
| Appearance =
| =
| Density =
| =
| MeltingPt =
| =
| BoilingPt =
| Solubility =
}}
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| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
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'''Phytanic acid''' (or '''3,7,11,15-tetramethyl hexadecanoic acid''') is a branched chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish.<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> Western diets are estimated to provide 50-100 mg of phytanic acid per day.<ref>Steinberg, D. Phytanic acid storage disease (Refsum's disease). In: Metabolic Basis of Inherited Disease. Edited by Stanbury JB, Wyngarden JB, Fredericksen DS, Goldstein JL, Brown MS, 5th edn. New York: McGraw Hill; 1983: 731-747.</ref> In a study conducted in Oxford, individuals who consumed meat had, on average, a 6.7-fold higher geometric mean plasma phytanic acid concentration than did [[vegans]].<ref name="pmid17868488">{{cite pmid|17868488}}</ref>
'''Phytanic acid''' (or '''3,7,11,15-tetramethyl hexadecanoic acid''') is a branched chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish.<ref>Brown P. J. 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 </ref> Western diets are estimated to provide mg of phytanic acid per day.<ref>Steinberg, D. Phytanic acid storage disease (Refsum's disease). In: Metabolic Basis of Inherited Disease. Edited by Stanbury JB, Wyngarden JB, Fredericksen DS, Goldstein JL, Brown MS, 5th edn. New York: McGraw Hill; 1983: 731-747.</ref> In a study conducted in Oxford, individuals who consumed meat had, on average, a 6.7-fold higher geometric mean plasma phytanic acid concentration than did [[vegans]].<ref name="pmid17868488">{{
| last1 = Allen | first1 = N. E.
| last2 = Grace | first2 = P. B.
| last3 = Ginn | first3 = A.
| last4 = Travis | first4 = R. C.
| last5 = Roddam | first5 = A. W.
| last6 = Appleby | first6 = P. N.
| last7 = Key | first7 = T.
| doi = 10.1017/S000711450782407X
| title = Phytanic acid: Measurement of plasma concentrations by gas–liquid chromatography–mass spectrometry analysis and associations with diet and other plasma fatty acids
| journal = British Journal of Nutrition
| volume = 99
| issue = 3
| pages = 653–659
| year = 2007
| pmid = 17868488
| doi-access = free
}}</ref>
==Human pathology==
==Human pathology==
Unlike most fatty acids, phytanic acid cannot be metabolized by [[beta oxidation|β-oxidation]]. Instead, it undergoes [[alpha oxidation|α-oxidation]] in the [[peroxisome]], where it is converted into [[pristanic acid]] by the removal of one carbon.<ref name="pmid16799769">{{cite pmid|16799769}}</ref> Pristanic acid can undergo several rounds of [[beta oxidation|β-oxidation]] in the peroxisome to form [[medium chain fatty acids]] that can be converted to carbon dioxide and water in [[mitochondria]].
Unlike most fatty acids, phytanic acid cannot be metabolized by [[beta oxidation|β-oxidation]]. Instead, it undergoes [[alpha oxidation|α-oxidation]] in the [[peroxisome]], where it is converted into [[pristanic acid]] by the removal of one carbon.<ref name="pmid16799769">{{
| last1 = Brink | first1 = D. M.
| last2 = Wanders | first2 = R. J. A.
| doi = 10.1007/s00018-005-5463-y
| title = Phytanic acid: Production from phytol, its breakdown and role in human disease
| journal = Cellular and Molecular Life Sciences
| volume = 63
| issue = 15
| pages = 1752–1765
| year = 2006
| pmid = 16799769
| pmc = 11136310
}}</ref> Pristanic acid can undergo several rounds of [[beta oxidation|β-oxidation]] in the peroxisome to form [[medium chain fatty acids]] that can be converted to carbon dioxide and water in [[mitochondria]].


Individuals with adult [[Refsum disease]], an autosomal recessive [[neurological disorder]] caused by mutations in the ''PHYH'' gene, have impaired α-oxidation activity and accumulate large stores of phytanic acid in their blood and tissues.<ref name="pmid7956237">{{cite pmid|7956237}}</ref> This frequently leads to [[peripheral polyneuropathy]], [[cerebellar ataxia]], [[retinitis pigmentosa]], [[anosmia]], and hearing loss.<ref name="pmid17956234">{{cite pmid|17956234}}</ref>
Individuals with adult [[Refsum disease]], an autosomal recessive [[neurological disorder]] caused by mutations in the ''PHYH'' gene, have impaired α-oxidation activity and accumulate large stores of phytanic acid in their blood and tissues.<ref name="pmid7956237">{{
| last1 = Quintaliani | first1 = G.
| last2 = Buoncristiani | first2 = U.
| last3 = Orecchini | first3 = A.
| last4 = Pierini | first4 = P.
| last5 = Ricci | first5 = R.
| last6 = Reboldi | first6 = G. P.
| title = The Umbria Regional Registry for hemodialyzed and transplanted patients. Preliminary experience with an informatic procedure
| journal = Contributions to Nephrology
| volume = 109
| pages = 96–99
| year = 1994
| doi = 10.1159/000423294
| pmid = 7956237
}}</ref> This frequently leads to [[peripheral polyneuropathy]], [[cerebellar ataxia]], [[retinitis pigmentosa]], [[anosmia]], and hearing loss.<ref name="pmid17956234">{{Cite journal
| last1 = Komen | first1 = J. C.
| last2 = Komen | first2 = R. J. A.
| title = Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid
| journal = Biochemical Society Transactions
| volume = 35
| issue = Pt 5
| pages = 865–869
| year = 2007
| pmid = 17956234
| doi = 10.1042/BST0350865
}}</ref>


==Presence in other organisms==
==Presence in other organisms==
In [[ruminant]] animals, 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="pmid9819701">{{cite pmid|9819701}}</ref> Recently, indirect evidence has been provided that the [[great apes]] ([[bonobos]], [[chimpanzees]], [[gorillas]], and [[orangutans]]), in contrast to humans, derive significant amounts of phytanic acid from the hindgut fermentation of plant materials.<ref name="pmid20932325">{{cite pmid|20932325}}</ref>
In [[ruminant]] animals, 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="pmid9819701">{{
| doi = 10.1023/A:1005476631419
| last1 = Verhoeven | first1 = N. M.
| last2 = Wanders | first2 = R. J.
| last3 = Poll-The | first3 = B. T.
| last4 = Saudubray | first4 = J. M.
| last5 = Jakobs | first5 = C.
| title = The metabolism of phytanic acid and pristanic acid in man: a review
| journal = Journal of Inherited Metabolic Disease
| volume = 21
| issue = 7
| pages = 697–728
| year = 1998
| pmid = 9819701
}}</ref> In contrast to observations made in [[human]]s, there is indirect evidence that diverse non-human [[primate]]s, including the [[great ape]]s other than humans ([[bonobo]]s, [[chimpanzee]]s, [[gorilla]]s and [[orangutan]]s), can derive significant amounts of phytanic acid from the [[hindgut fermentation]] of plant materials.<ref name="pmid20932325">{{Cite journal
| last1 = Watkins | first1 = P. A.
| last2 = Moser | first2 = A. B.
| last3 = Toomer | first3 = C. B.
| last4 = Steinberg | first4 = S. J.
| last5 = Moser | first5 = H. W.
| last6 = Karaman | first6 = M. W.
| last7 = Ramaswamy | first7 = K.
| last8 = Siegmund | first8 = K. D.
| last9 = Lee | first9 = D. R.
| last10 = Ely | first10 = J. J.
| last11 = Ryder | first11 = O. A.
| last12 = Hacia | first12 = J. G.
| 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
| pmid = 20932325
| pmc = 2964658
| doi = 10.1186/1472-6793-10-19
| doi-access = free
}}</ref><ref name="pmid23379307">{{Cite journal
| last1 = Moser | first1 = A. B.
| last2 = Hey | first2 = J.
| last3 = Dranchak | first3 = P. K.
| last4 = Karaman | first4 = M. W.
| last5 = Zhao | first5 = J.
| last6 = Cox | first6 = L. A.
| last7 = Ryder | first7 = O. A.
| last8 = Hacia | first8 = J. G.
| doi = 10.1186/1476-511X-12-10
| 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
| issue = 1
| pages = 10
| year = 2013
| pmid = 23379307
| pmc = 3571895
| doi-access = free
}}</ref>


[[Freshwater]] [[sea sponge|sponge]]s contain [[terpenoid]] acids such as 4,8,12-trimethyltridecanoic, phytanic and [[pristanic acid]]s, which indicates that these acids may have [[chemotaxonomy|chemotaxonomical]] significance for both [[Marine (ocean)|marine]] and freshwater sponges.<ref>Rezanka, T., Dembitsky, V. M. 1993. Isoprenoid polyunsaturated fatty acids from freshwater sponges. Journal of Natural Products 56, 1898-1904.</ref>
[[Freshwater]] [[sea sponge|sponge]]s contain [[terpenoid]] acids such as 4,8,12-trimethyltridecanoic, phytanic and [[pristanic acid]]s, which indicates that these acids may have [[chemotaxonomy|chemotaxonomical]] significance for both [[Marine (ocean)|marine]] and freshwater sponges.<ref>Rezanka T. Dembitsky V. M. 1993 Isoprenoid polyunsaturated fatty acids from freshwater sponges Journal of Natural Products 56 .</ref>


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> 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 sumac flea beetle, are reported to use [[phytol]] and its metabolites (e.g. phytanic acid) as chemical deterrents against predation.<ref> Venci F.V. Morton T.C. 1998 The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae) Chemoecology 8 .</ref> These compounds originate from host plants.


==Modulator of transcription==
==Modulator of transcription==
Phytanic acid and its metabolites have been reported to bind to and/or activate the [[transcription factors]] [[PPAR-alpha]] <ref name="pmid15654129">{{cite pmid|15654129}}</ref> and [[retinoid X receptor]] (RXR).<ref name="pmid8856661">{{cite pmid|8856661}}</ref>
Phytanic acid and its metabolites have been reported to bind to and/or activate the [[transcription factors]] [[PPAR-alpha]]<ref name="pmid15654129">{{
| last1 = Gloerich | first1 = J.
| last2 = Van Vlies | first2 = N.
| last3 = Jansen | first3 = G. A.
| last4 = Denis | first4 = S.
| last5 = Ruiter | first5 = J. P. N.
| last6 = Van Werkhoven | first6 = M. A.
| last7 = Duran | first7 = M.
| last8 = Vaz | first8 = F. M.
| last9 = Wanders | first9 = R. J. A.
| 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
| doi = 10.1194/jlr.M400337-JLR200 | pmid=15654129
| doi-access = free
}}</ref> and [[retinoid X receptor]] (RXR).<ref name="pmid8856661">{{Cite journal
| doi = 10.1091/mbc.7.8.1153
| 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.
| title = Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR
| journal = Molecular Biology of the Cell
| volume = 7
| issue = 8
| pages = 1153–1166
| year = 1996
| pmid = 8856661
| pmc = 275969
}}</ref>


==References==
==References==
{{Reflist|2}}
{{Reflist|2}}

==External links==


{{Peroxisomal metabolism intermediates}}
{{Peroxisomal metabolism intermediates}}
[[Category:Carboxylic acids]]
[[Category:Diterpenes]]


[[Category:Alkanoic acids]]
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