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Phytanic acid



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
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
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Phytanic acid (or 3,7,11,15-tetramethyl hexadecanoic acid) is present in human diet or in animal tissues where it may be derived from chlorophyll in plant extracts. Phytanic acid derives from the corresponding alcohol, phytol, and is oxidized into pristanic acid.

Additional recommended knowledge

Human pathology

It can also characterize a precise human pathology, Refsum's syndrome.

This inherited neurological disorder is characterized by an accumulation of a normal metabolite of phytol (phytanic acid) in blood and tissues, and the disorder was later found to be related to deficiency in the α-oxidation pathway in the liver.

Function in other animals

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.

Phytanic acid accumulates in the fat of ruminant animals. Most animals lack the necessary enzyme to cleave phytol from chlorophyll. The rumen microorganisms, however, can cleave this bond and release phytol, which is converted to phytanic acid and subsequently incorparated into the animal's fat.[1]

References

  1. ^ Verhoeven, N. M., Wanders, R. J., et al. 1998. The metabolism of phytanic acid and pristanic acid in man: a review. Journal of Inherited Metabolic Diseases 21, 697-728.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phytanic_acid". A list of authors is available in Wikipedia.
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