Phytol

Phytol

Names
IUPAC names (2E,7R,11R)-3,7,11,15- tetramethyl-2-hexadecen-1-ol
Identifiers
CAS Number	7541-49-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17327 Y
ChEMBL	ChEMBL3039479 N
ChemSpider	4444094 Y
ECHA InfoCard	100.131.435
PubChem	5280435
InChI InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1 Y Key: BOTWFXYSPFMFNR-PYDDKJGSSA-N Y InChI=1/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1 Key: BOTWFXYSPFMFNR-PYDDKJGSBV
SMILES C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C
Properties
Chemical formula	C20H40O
Molar mass	296.54 g·mol−1
Density	0.850 g cm−3
Boiling point	203 to 204 °C (397 to 399 °F; 476 to 477 K) at 10 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. In ruminants, 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 shark liver it yields pristane.

Refsum disease, an autosomal recessive disorder that results from the accumulation of large stores of phytanic acid in tissues, frequently manifests peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss. Although humans cannot derive phytanic acid from chlorophyll, they can convert free phytol into phytanic acid. Thus, patients with Refsum disease should limit their intake of phytanic acid and free phytol. The amount of free phytol in numerous food products has been reported.

Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. phytanic acid) as chemical deterrents against predation. These compounds originate from host plants.

Indirect evidence has been provided that, in contrast to humans, diverse non-human primates can derive significant amounts of phytol from the hindgut fermentation of plant materials.

Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha and retinoid X receptor (RXR). The metabolites phytanic acid and pristanic acid are naturally occurring ligands. In mice oral phytol induces massive proliferation of peroxisomes in several organs.