Phytane

Phytane is the isoprenoid alkane formed when phytol, a constituent of chlorophyll, loses its hydroxyl group. When phytol loses one carbon atom, it yields pristane. Other sources of phytane and pristane have also been proposed than phytol. Phytane is the isoprenoid alkane formed when phytol, a constituent of chlorophyll, loses its hydroxyl group. When phytol loses one carbon atom, it yields pristane. Other sources of phytane and pristane have also been proposed than phytol. Pristane and phytane are common constituents in petroleum and have been used as proxies for depositional redox conditions, as well as for correlating oil and its source rock (i.e. elucidating where oil formed). In environmental studies, pristane and phytane are target compounds for investigating oil spills. Phytane is a non-polar organic compound that is a clear and colorless liquid at room temperature. It is a head-to-tail linked regular isoprenoid with chemical formula C20H42. Phytane has many structural isomers. Among them, crocetane is a tail-to-tail linked isoprenoid and often co-elutes with phytane during gas chromatography (GC) due to its structural similarity. Phytane also has many stereoisomers because of its three stereo carbons, C-6, C-10 and C-14. Whereas pristane has two stereo carbons, C-6 and C-10. Direct measurement of these isomers has not been reported using gas chromatography. The substituent of phytane is phytanyl. Phytanyl groups are frequently found in archaeal membrane lipids of methanogenic and halophilic archaea (e.g., in archaeol). Phytene is the singly unsaturated version of phytane. Phytene is also found as the functional group phytyl in many organic molecules of biological importance such as chlorophyll, tocopherol (vitamin E), and phylloquinone (vitamin K1). Phytene's corresponding alcohol is phytol. Geranylgeranene is the fully unsaturated form of phytane, and its corresponding substituent is geranylgeranyl. The major source of phytane and pristane is thought to be chlorophyll. Chlorophyll is one of the most important photosynthetic pigments in plants, algae, and cyanobacteria, and is the most abundant tetrapyrrole in the biosphere. Hydrolysis of chlorophyll a, b, d, and f during diagenesis in marine sediments, or during invertebrate feeding releases phytol, which is then converted to phytane or pristane. Another possible source of phytane and pristane is archaeal ether lipids. Laboratory studies show that thermal maturation of methanogenic archaea generates pristane and phytane from diphytanyl glyceryl ethers (archaeols). In addition, pristane can be derived from tocopherols and methyltrimethyltridecylchromans (MTTCs).