Phytanic acid
From Wikipedia, the free encyclopedia
| Phytanic acid | |
|---|---|
 |
|
| IUPAC name | (7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid |
| Identifiers | |
| CAS number | [] |
| PubChem | |
| 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.
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. 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]
[edit] Reference
- ^ 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.
