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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/28 21:19:38」(JST)

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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.^[1] Western diets are estimated to provide 50-100 mg of phytanic acid per day.^[2] 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.^[3]

Human pathology

Unlike most fatty acids, phytanic acid cannot be metabolized by β-oxidation. Instead, it undergoes α-oxidation in the peroxisome, where it is converted into pristanic acid by the removal of one carbon.^[4] Pristanic acid can undergo several rounds of 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.^[5] This frequently leads to peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss.^[6]

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.^[7] In contrast to observations made in humans, there is indirect evidence that diverse non human primates, including the great apes (bonobos, chimpanzees, gorillas, and orangutans), can derive significant amounts of phytanic acid from the hindgut fermentation of plant materials.^[8]^[9]

Freshwater sponges contain terpenoid acids such as 4,8,12-trimethyltridecanoic, phytanic and pristanic acids, which indicates that these acids may have chemotaxonomical significance for both marine and freshwater sponges.^[10]

Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. phytanic acid) as chemical deterrents against predation.^[11] These compounds originate from host plants.

Modulator of transcription

Phytanic acid and its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha ^[12] and retinoid X receptor (RXR).^[13]

References

^ 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
^ 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.
^ Allen, N. E.; Grace, P. B.; Ginn, A.; Travis, R. C.; Roddam, A. W.; Appleby, P. N.; Key, T. (2007). "Phytanic acid: Measurement of plasma concentrations by gas–liquid chromatography–mass spectrometry analysis and associations with diet and other plasma fatty acids". British Journal of Nutrition 99 (3): 653–659. doi:10.1017/S000711450782407X. PMID 17868488. edit
^ 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): 1752–1765. doi:10.1007/s00018-005-5463-y. PMID 16799769. edit
^ Quintaliani, G.; Buoncristiani, U.; Orecchini, A.; Pierini, P.; Ricci, R.; Reboldi, G. P. (1994). "The Umbria Regional Registry for hemodialyzed and transplanted patients. Preliminary experience with an informatic procedure". Contributions to nephrology 109: 96–99. PMID 7956237. edit
^ Komen, J. C.; Komen, R. J. A. (2007). "Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid". Biochemical Society Transactions 35 (Pt 5): 865–869. doi:10.1042/BST0350865. PMID 17956234. edit
^ Verhoeven, N. M.; Wanders, R. J.; Poll-The, B. T.; Saudubray, J. M.; Jakobs, C. (1998). "The metabolism of phytanic acid and pristanic acid in man: a review". Journal of Inherited Metabolic Disease 21 (7): 697–728. doi:10.1023/A:1005476631419. PMID 9819701. edit
^ Watkins, P. A.; Moser, A. B.; Toomer, C. B.; Steinberg, S. J.; Moser, H. W.; Karaman, M. W.; Ramaswamy, K.; Siegmund, K. D.; Lee, D. R.; Ely, J. J.; Ryder, O. A.; Hacia, J. 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. edit
^ Moser, A. B.; Hey, J.; Dranchak, P. K.; Karaman, M. W.; Zhao, J.; Cox, L. A.; Ryder, O. A.; Hacia, J. 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 (1): 10. doi:10.1186/1476-511X-12-10. PMID 23379307. edit
^ Rezanka, T., Dembitsky, V. M. 1993. Isoprenoid polyunsaturated fatty acids from freshwater sponges. Journal of Natural Products 56, 1898-1904.
^ Venci, F.V. and Morton, T.C. 1998. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology 8, 25-32.
^ Gloerich, J.; Van Vlies, N.; Jansen, G. A.; Denis, S.; Ruiter, J. P. N.; Van Werkhoven, M. A.; Duran, M.; Vaz, F. M.; Wanders, R. J. A. (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. doi:10.1194/jlr.M400337-JLR200. edit
^ 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): 1153–1166. doi:10.1091/mbc.7.8.1153. PMC 275969. PMID 8856661. edit

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UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ペルオキシソーム病 peroxisomal disorders
2. Neuropathies associated with hereditary disorders
3. 網膜色素変性症：治療 retinitis pigmentosa treatment
4. 遺伝性運動失調の概要 overview of the hereditary ataxias
5. 先天性代謝異常：分類 inborn errors of metabolism classification

English Journal

Stereoselective synthesis of perdeuterated phytanic acid, its phospholipid derivatives and their formation into lipid model membranes for neutron reflectivity studies.

Yepuri NR1, Holt SA2, Moraes G3, Holden PJ3, Hossain KR4, Valenzuela SM4, James M5, Darwish TA3.
Chemistry and physics of lipids.Chem Phys Lipids.2014 May 2. pii: S0009-3084(14)00048-6. doi: 10.1016/j.chemphyslip.2014.04.004. [Epub ahead of print]
We describe a straightforward method to synthesise large scale (gram quantities) of highly deuterated phytanic acid from commercially available phytol while preserving the stereochemistry around the chiral centres. The subsequent synthesis of deuterated analogues of archeabacteria membrane lipid tai
PMID 24794716

Chemical Offense by Means of Toxicysts in the Freshwater Ciliate, Coleps hirtus.

Buonanno F1, Anesi A, Guella G, Kumar S, Bharti D, La Terza A, Quassinti L, Bramucci M, Ortenzi C.
The Journal of eukaryotic microbiology.J Eukaryot Microbiol.2014 May;61(3):293-304. doi: 10.1111/jeu.12106. Epub 2014 Mar 5.
Coleps hirtus is a small common freshwater ciliate belonging to the protostomatid group, its body covered by calcified plates assembled to form an armor. Coleps feeds on bacteria, algae, flagellates, living and dead ciliates, animal and plant tissues. To assist its carnivorous feeding the ciliate is
PMID 24512001

Peroxisomal D-bifunctional protein deficiency: three adults diagnosed by whole-exome sequencing.

Lines MA1, Jobling R, Brady L, Marshall CR, Scherer SW, Rodriguez AR, Lee L, Lang AE, Mestre TA, Wanders RJ, Ferdinandusse S, Tarnopolsky MA; Canadian Pediatric Genetic Disorders Sequencing Consortium (FORGE Canada).
Neurology.Neurology.2014 Mar 18;82(11):963-8. doi: 10.1212/WNL.0000000000000219. Epub 2014 Feb 19.
OBJECTIVE: To determine the causative genetic lesion in 3 adult siblings with a slowly progressive, juvenile-onset phenotype comprising cerebellar atrophy and ataxia, intellectual decline, hearing loss, hypogonadism, hyperreflexia, a demyelinating sensorimotor neuropathy, and (in 2 of 3 probands) su
PMID 24553428

Japanese Journal

Gas chromatography/mass spectrometry analysis of very long chain fatty acids, docosahexaenoic acid, phytanic acid and plasmalogen for the screening of peroxisomal disorders

TAKEMOTO Yasuhiko,SUZUKI Yasuyuki,HORIBE Ryoko,SHIMOZAWA Nobuyuki,WANDERS Ronald J. A.,KONDO Naomi
Brain & development 25(7), 481-487, 2003-10-14
NAID 10020553571

Rapid stable isotope dilution analysis of very-long-chain fatty acids, pristanic acid and phytanic acid using gas chromatography-electron impact mass spectrometry

VREKEN P.,VAN LINT A. E. M.,BOOTSMA A. H.,OVERMARS H.,WANDERS R. J. A.,VAN GENNIP A. H.
Journal of chromatography. B, Biomedical sciences and applications 713(2), 281-287, 1998-08-25
NAID 10024530211

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★リンクテーブル★

リンク元	「フィタン酸」
拡張検索	「infantile phytanic acid storage disease」

「フィタン酸」

Phytanic acid
	IUPAC name (7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid
	Other names phytanoic acid
Identifiers
CAS number	14721-66-5
PubChem	468706
MeSH	Phytanic+acid
Jmol-3D images	Image 1
	SMILES CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)CC(=O)O ;
Properties
Molecular formula	C20H40O2
Molar mass	312.53 g mol−1
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: phytanic acid
同: 3,7,11,15-テトラメチルヘキサデカン酸 3,7,11,15-tetramethylhexadecanoic acid
関: レフサム病

「infantile phytanic acid storage disease」

　　[★] 乳児型フィタン酸蓄積症

[1] 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

[2] 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.

[pmid17868488-3] Allen, N. E.; Grace, P. B.; Ginn, A.; Travis, R. C.; Roddam, A. W.; Appleby, P. N.; Key, T. (2007). "Phytanic acid: Measurement of plasma concentrations by gas–liquid chromatography–mass spectrometry analysis and associations with diet and other plasma fatty acids". British Journal of Nutrition 99 (3): 653–659. doi:10.1017/S000711450782407X. PMID 17868488. edit

[pmid16799769-4] 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): 1752–1765. doi:10.1007/s00018-005-5463-y. PMID 16799769. edit

[pmid7956237-5] Quintaliani, G.; Buoncristiani, U.; Orecchini, A.; Pierini, P.; Ricci, R.; Reboldi, G. P. (1994). "The Umbria Regional Registry for hemodialyzed and transplanted patients. Preliminary experience with an informatic procedure". Contributions to nephrology 109: 96–99. PMID 7956237. edit

[pmid17956234-6] Komen, J. C.; Komen, R. J. A. (2007). "Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid". Biochemical Society Transactions 35 (Pt 5): 865–869. doi:10.1042/BST0350865. PMID 17956234. edit

[pmid9819701-7] Verhoeven, N. M.; Wanders, R. J.; Poll-The, B. T.; Saudubray, J. M.; Jakobs, C. (1998). "The metabolism of phytanic acid and pristanic acid in man: a review". Journal of Inherited Metabolic Disease 21 (7): 697–728. doi:10.1023/A:1005476631419. PMID 9819701. edit

[pmid20932325-8] Watkins, P. A.; Moser, A. B.; Toomer, C. B.; Steinberg, S. J.; Moser, H. W.; Karaman, M. W.; Ramaswamy, K.; Siegmund, K. D.; Lee, D. R.; Ely, J. J.; Ryder, O. A.; Hacia, J. 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. edit

[pmid23379307-9] Moser, A. B.; Hey, J.; Dranchak, P. K.; Karaman, M. W.; Zhao, J.; Cox, L. A.; Ryder, O. A.; Hacia, J. 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 (1): 10. doi:10.1186/1476-511X-12-10. PMID 23379307. edit

[10] Rezanka, T., Dembitsky, V. M. 1993. Isoprenoid polyunsaturated fatty acids from freshwater sponges. Journal of Natural Products 56, 1898-1904.

[11] Venci, F.V. and Morton, T.C. 1998. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology 8, 25-32.

[pmid15654129-12] Gloerich, J.; Van Vlies, N.; Jansen, G. A.; Denis, S.; Ruiter, J. P. N.; Van Werkhoven, M. A.; Duran, M.; Vaz, F. M.; Wanders, R. J. A. (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. doi:10.1194/jlr.M400337-JLR200. edit

[pmid8856661-13] 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): 1153–1166. doi:10.1091/mbc.7.8.1153. PMC 275969. PMID 8856661. edit

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phytanic acid