Isophytol

Structural formula
General
Surname	Isophytol
other names	3,7,11,15-tetramethyl-1-hexadecen-3-ol
Molecular formula	C 20 H 40 O
Brief description	colorless liquid
External identifiers / databases
EC number	208-008-8
ECHA InfoCard	100.007.281
PubChem	10453
Wikidata	Q26841319
properties
Molar mass	296.53 g mol −1
Physical state	liquid
density	0.841 g cm −3 (25 ° C)
Melting point	−79 ° C
boiling point	309 ° C
Vapor pressure	0.002 hPa (60 ° C)
solubility	practically soluble in water (5.8 mg l −1 at 25 ° C); soluble in organic solvents ;
Refractive index	1.457 (20 ° C)
safety instructions
H and P phrases	H: 315-410
	P: 273-501
Toxicological data	5400 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 169 mg kg −1 ( LD 50 , mouse , ip ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Isophytol is a chemical compound from the group of terpenoid alcohols .

Occurrence

Isophytol occurs naturally in some plants (at least 15) and algae (2 species, such as Laurencia pinnatifida ). According to some sources, there is no direct evidence that it arises as a decomposition product of chlorophyll .

Extraction and presentation

Isophytol can be formed by transition metal-catalyzed addition of diethyl malonate to myrcene and subsequent acidification.

The entire chemical synthesis of isophytol can start from the addition of acetylene to acetone , resulting in 2-methyl-3-butyn-2-ol . This is converted in the presence of a palladium catalyst to 2-methylbut-3-en-2-ol , which in turn is converted either with diketene or acetic acid ester to give acetoacetate and the latter thermally with 6-methyl-5-hepten-2-one . Alternatively, 2-methylbut-3-en-2-ol can be reacted with 2-methoxypropene to give 6-methyl-5-hepten-2-one. In a third synthetic route, isoprene hydrochloride can be reacted with acetone in the presence of an alkaline condensing agent or in the presence of an organic base as a catalyst to give 6-methyl-5-hepten-2-one. 6-methyl-5-hepten-2-one is then reacted with acetylene to form dehydrolinalool , whereupon 2-methoxypropene is added to produce pseudoionone . The three double bonds are hydrated to 6,10-dimethyl-2-undecanone , which is reacted with acetylene to give 3,7,11-trimethyl-1-dodecyn-3-ol . 2-methoxypropene is added to form 6,10-14-trimethyl-4,5-pentadecadien-2-one, which is hydrated to hexahydrofarnesylacetone . This is reacted again with acetylene to give 3,7,11,15-tetramethyl-1-hexadecyn-3-ol ( dehydroisophytol ). which eventually becomes hydrated to isophytol.

Racemic isomer mixtures can be prepared from linalool and citral .

The synthesis from pseudojonone and propargyl alcohol is also possible .

properties

Isophytol is a colorless oily liquid that is practically insoluble in water.

use

Isophytol is mainly used as an intermediate in the synthesis of vitamins E and K , as well as an intermediate in the production of phytol , as a diluent in high-priced fragrances and as a flavoring agent.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Data sheet Isophytol, ≥97.0% from Sigma-Aldrich , accessed on January 8, 2019 ( PDF ).
↑ ^a ^b entry on isophytol. In: Römpp Online . Georg Thieme Verlag, accessed on January 8, 2019.
↑ ^a ^b ^c ^d OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 1-hexadecen-3-ol, 3,7,11,15-tetramethyl- , accessed on January 8, 2019.
↑ ^a ^b Entry on Isophytol in the Hazardous Substances Data Bank , accessed January 8, 2019.
↑ Kikumasa Sato, Yoshie Kurihara, Shigehiro Abe: Synthesis of Isophytol. In: The Journal of Organic Chemistry. 28, 1963, p. 45, doi : 10.1021 / jo01036a009 .
^ Robert S. Harris: Vitamins and Hormones, Volume 17 . Academic Press, 1959, ISBN 978-0-08-086614-7 , pp. 69 ( limited preview in Google Book search).
↑ D. McGinty, CS Letizia, AM Api: Fragrance material review on isophytol. In: Food and Chemical Toxicology. 48, 2010, p. S76, doi : 10.1016 / j.fct.2009.11.015 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Data sheet Isophytol, ≥97.0% from Sigma-Aldrich , accessed on January 8, 2019 ( PDF ).

[RömppOnline-2] try on isophytol. In: Römpp Online . Georg Thieme Verlag, accessed on January 8, 2019.

[SIDS-3] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for 1-hexadecen-3-ol, 3,7,11,15-tetramethyl- , accessed on January 8, 2019.

[HSDB-4] Entry on Isophytol in the Hazardous Substances Data Bank , accessed January 8, 2019.

[DOI10.1021/jo01036a009-5] Kikumasa Sato, Yoshie Kurihara, Shigehiro Abe: Synthesis of Isophytol. In: The Journal of Organic Chemistry. 28, 1963, p. 45, doi : 10.1021 / jo01036a009 .

[Robert_Harris-6] Robert S. Harris: Vitamins and Hormones, Volume 17 . Academic Press, 1959, ISBN 978-0-08-086614-7 , pp. 69 ( limited preview in Google Book search).

[DOI10.1016/j.fct.2009.11.015-7] D. McGinty, CS Letizia, AM Api: Fragrance material review on isophytol. In: Food and Chemical Toxicology. 48, 2010, p. S76, doi : 10.1016 / j.fct.2009.11.015 .