Trans-phytol

The stems of E. arvense contain volatile oil with 25 identified compounds. The major constituents include hexahydrofamesyl acetone, geranyl acetone, thymol, and trans-phytol. ... 

D Differetiang nonrefined and refined oils is an important task in food control. In chlorophyll only trans-phytol is to be found. The relative abundance of cA-phytol versus frrz 5-phytol has been used as a marker in authenticating the nonrefined edible oils. The absence of cis-phytol in the nonrefined edible oils can be used as a marker for authentication (Vetter et al., 2012). 

High, E. G. and H. G. Day (1951). Effects of different amounts of lutein, squalene, phytol and related substances on the utilization of carotene and vitamin A for storage and growth in the rat. J. Nutr. 43 245-260. Johnson, E. J. et al. (1997). Beta-carotene isomers in human serum, breast milk and buccal mucosa cells after continuous oral doses of -trans and 9-cis beta-carotene. J. Nutr. 127(10) 1993-1999. 

The separation of the stereoisomers of phytol (3, 7, 1, 15-tetramethyl-2-hexadecen-l-ol, C2oH400) has been described6 at a relatively large scale (about 20 kg per day). The synthetic phytol is a mixture of cis (33%) and trans (67%) isomers, the latter being used in perfumery. This separation is presented in the following. 

NevL Phytol. 1986, Trans.. Br. mycol,. Exper. Mycol, 1978,... 

Oxidation reactions of this nature are common in the literature. For example, selenium dioxide in refluxing etiumolic solution brought about the allylic oxidative rearrangement geranyl acetate, which was further functionalized in a synthesis of the norsesquiterpenoid gytinidal (equation 46). This trans formation was also used in a total synthesis of phytol. Similarly, an a, -unsaturated aldehyde was obtained undm similar conditions in studies of a synthesis of pentalenic acid derivatives (equation 47). ... 

Optically active phytol has been synthesised (ref. 75) and the methodology is depicted in Scheme 24. In this route (R)-(+)-citronellol was converted to 4(R),8-dimethylnonanoic acid which was then anodically cross-coupled with methyl hydrogen 3(R)-methylglutarate to give 3(R), 7(R), 11-trimethyldodecanoic acid. Similar cross-coupling with levulinic acid afforded 6(R),10(R),14-trimethylpentadecan-2-one and reaction with methoxyacetylene followed by acidic treatment gave a mixture of cis and trans methyl phytenoates which were separated. Reduction of the trans ester with lithium aluminium hydride resulted in phytol identical with the natural product. 

Phytol is a fatty alcohol with 20 carbon atoms (3, 7, 11, 15-tetramethyl-2-hexadecene-l-ol, C20H40O) from the group ofterpenes. Phytol is used in the synthesis of vitamins E and K]. In addition, it is a lipophilic component of chlorophyll. Because of a double bond cis- and trans-isomers exist. The trans-isomer is used as a fixener in the perfume industry. 

Due to the three chiral centres, phytane has diastereoisomers with different physical properties. Fischer s suggestion that phytol is biogenically produced from geraniol and farnesol was followed by Burrell , and the stereochemistry of phytol was established as trans-3,l R),ll R). 

Vitamin K,(20) (VKl), or phylloquinone, is the generic name of 2-methyl-3-eicosa-2 -ene-l,4-naphthoquinone. The (2 -tram-) phytyl side chain in position 3 of the naphthoquinone nucleus contains 20 carbon atoms, structured in four isoprene units, the last three of them totally reduced (see Structure 1 in Fig. 1). If a synthetic VKl is analyzed, always a mixture of di/trans -isomers can be detected, deriving from synthetic phytol, which consists of a mixture of these isomers. VKl in pure form an orange oil and a fat-soluble vitamin is insoluble in water, slightly soluble in ethanol, and can be easily solved in ether, hexane. 

Vetter, W., Schroder, M Lehnert, K. (2012). Differentiation of refined and virgin edible oils by means of the trans- and cis-phytol isomer distribution. J. Agric. Food Chem., 60, 6103-6107. 

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