Phytanic acid
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IUPAC name
(7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid
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| Other names
phytanoic acid
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.159.135 |
| MeSH | Phytanic+acid |
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PubChem CID
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| Properties | |
| C20H40O2 | |
| Molar mass | 312.54 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
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. Western diets are estimated to provide 50–100 mg of phytanic acid per day. 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.
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. 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 .
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. This frequently leads to peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss.
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. 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.
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