Phytol

Phytol
Names
	IUPAC name (5R,9R)-5,6,7,8,9,10,11,12-Octahydro-1,6-secoretinol
	Systematic IUPAC name (2E,7R,11R)-3,7,11,15-Tetramethylhexadec-2-en-1-ol
Identifiers
CAS Number	150-86-7 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:17327 ;
ChEMBL	ChEMBL3039479 ;
ChemSpider	4444094 ;
ECHA InfoCard	100.131.435
PubChem CID	5280435;
UNII	5BC2RZ81NG ;
CompTox Dashboard (EPA)	DTXSID1040586 ;
	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 Key: BOTWFXYSPFMFNR-PYDDKJGSSA-N ; 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	296.539 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). verify (what is ?) Infobox references

Phytol (florasol, phytosol) is an acyclic

toilet soaps, and detergents,^[3] as well as in some cannabis distillates as a diluent or for flavoring.^[4] Its worldwide use has been estimated to be approximately 0.1–1.0 metric tons per year.^[5]

peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss.^[6] 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.^[7] The amount of free phytol in numerous food products has been reported.^[8]

Rats

It was found to cause

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.^[9]

Other vertebrates

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.^[10] In shark liver it yields pristane.

History

Controversy

In 2020,

Canadian government published an amendment to Canadian cannabis regulations regarding "flavours in cannabis extracts".^[12]

Roles in nature

Insects, such as the sumac flea beetle, are reported to use phytol and its metabolites (e.g. phytanic acid) as chemical deterrents against predation.^[13] 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.^[14]^[15]

Modulator of transcription

Phytol and/or its metabolites have been reported to bind to and/or activate the

PPAR-alpha^[16] and retinoid X receptor (RXR).^[17] The metabolites phytanic acid and pristanic acid are naturally occurring ligands.^[18] In mice, oral phytol induces massive proliferation of peroxisomes in several organs.^[19]

Possible biomedical applications

Phytol has been investigated for its potential anxiolytic, metabolism-modulating, cytotoxic, antioxidant, autophagy- and apoptosis-inducing, antinociceptive, anti-inflammatory, immune-modulating, and antimicrobial effects.[20]

Geochemical biomarker

Phytol is likely the most abundant acyclic isoprenoid compound present in the biosphere and its degradation products have been used as biogeochemical tracers in aquatic environments.^[21]

References

PMID 17628175
.

doi:10.2174/1385272033486279
.

PMID 20141879
.

^ "• Winberry Farms". Archived from the original on 2021-07-21. Retrieved 2019-11-09.

^ IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.

PMID 17956237
.

S2CID 39842405
.

doi:10.1111/j.1365-277X.1993.tb00375.x
.

PMID 33441006
. Retrieved 26 May 2023.

S2CID 9186973
.

^ Brown, David (19 July 2021). "Study looking at vape pen ingredient phytol shows serious health concerns". StratCann. Retrieved 29 May 2023.

^ "Canada Gazette, Part 1, Volume 155, Number 25". canadagazette.gc.ca. Government of Canada. 19 June 2021. Retrieved 29 May 2023.

S2CID 25886345
.

PMID 20932325
.

PMID 23379307
.

PMID 15654129
.

PMID 8856661
.

PMID 14713238
.

PMID 2423950
.

S2CID 52055348
.

doi:10.1016/S0146-6380(02)00185-7
.

v
t
e
Fatty acid metabolic intermediates
Synthesis

Acetyl-CoA

Malonyl-CoA

Degradation

Acyl-CoA

Acetyl-CoA

Peroxisomal
Phytol

Phytanic acid

Phytanoyl-CoA

Pristanic acid

Propionyl-CoA

Other

Mevalonic acid

Very long chain fatty acid

Retrieved from "https://en.wikipedia.org/w/index.php?title=Phytol&oldid=1181978236"

[1] PMID 17628175
.

[2] :10.2174/1385272033486279
.

[3] PMID 20141879
.

[4] "• Winberry Farms". Archived from the original on 2021-07-21. Retrieved 2019-11-09.

[5] IFRA (International Fragrance Association), 2004. Use Level Survey, August 2004.

[pmid17956237-6] PMID 17956237
.

[7] S2CID 39842405
.

[8] :10.1111/j.1365-277X.1993.tb00375.x
.

[9] PMID 33441006
. Retrieved 26 May 2023.

[pmid16799769-10] S2CID 9186973
.

[11] Brown, David (19 July 2021). "Study looking at vape pen ingredient phytol shows serious health concerns". StratCann. Retrieved 29 May 2023.

[12] "Canada Gazette, Part 1, Volume 155, Number 25". canadagazette.gc.ca. Government of Canada. 19 June 2021. Retrieved 29 May 2023.

[13] S2CID 25886345
.

[pmid20932325-14] PMID 20932325
.

[pmid23379307-15] PMID 23379307
.

[16] PMID 15654129
.

[17] PMID 8856661
.

[18] PMID 14713238
.

[19] PMID 2423950
.

[20] S2CID 52055348
.

[21] :10.1016/S0146-6380(02)00185-7
.

[3]

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[5]

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