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phytol

Structure via PubChem · Public domain (PubChem)

EntityQ415945· pop 26· linked from 220 articles

Also known as (E)-phytol, trans-phytol, (2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecen-1-ol

Phytol (florasol, phytosol) is an acyclic hydrogenated diterpene alcohol that is used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1, as well as in the fragrance industry. Its other commercial uses include cosmetics, shampoos, toilet soaps, and detergents, as well as in some cannabis distillates as a diluent or for flavoring. It smells grassy and dominates the aroma of certain green teas.

Chemical data

Formula
C20H40O
Molecular weight
296.5 g/mol
IUPAC name
(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol
SMILES
C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C
InChIKey
BOTWFXYSPFMFNR-PYDDKJGSSA-N
XLogP
8.2
Polar surface area
20.2 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

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Research

35,926 papers

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Wikidata facts

Mass
296.3079159
Show 4 more facts
canonical SMILES
CC(C)CCCC(C)CCCC(C)CCCC(=CCO)C
chemical formula
C₂₀H₄₀O
isomeric SMILES
C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C
Commons category
Phytol
Sources (5)

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~4 min read

Article

12 sections
Contents
  • Pharmacology
  • Humans
  • Rats
  • Other vertebrates
  • History
  • Controversy
  • Roles in nature
  • Modulator of transcription
  • Possible biomedical applications
  • Geochemical biomarker
  • See also
  • References

Phytol (florasol, phytosol) is an acyclic hydrogenated diterpene alcohol that is used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1, as well as in the fragrance industry. Its other commercial uses include cosmetics, shampoos, toilet soaps, and detergents, as well as in some cannabis distillates as a diluent or for flavoring. It smells grassy and dominates the aroma of certain green teas.

Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year. ==Pharmacology== ===Humans=== Refsum disease (also known as adult Refsum disease) is an autosomal recessive disorder that results in the accumulation of toxic stores of phytanic acid in tissues and frequently manifests as a variable combination of 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. ===Rats=== Phytol was found to cause pulmonary hemorrhage and necrosis of nose, throat and lung tissue when exposed in aerosol to Sprague Dawley rats, with no safe dose range being established. A majority of the phytol rats turned out dead or moribund, leading to 2nd-day termination of the 14-day study.

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