Isophytol

Isophytol is a terpenoid alcohol that is used as a fragrance and as an intermediate in the production of vitamin E and K1.[1][2]

Isophytol
Names
IUPAC name
3,7,11,15-Tetramethylhexadec-1-en-3-ol
Identifiers
3D model (JSmol)
ECHA InfoCard 100.007.281
EC Number
  • 208-008-8
UNII
Properties
C20H40O
Molar mass 296.539 g·mol−1
Appearance Colorless viscous liquid
Density 0.8458 g/cm3 (20 ºC)
Boiling point 334.88 °C (634.78 °F; 608.03 K)
Poor
Solubility in other solvents Very soluble in benzene, diethyl ether, and ethanol
Hazards
GHS pictograms
P264, P273, P280, P302+352, P321, P332+313, P362, P391, P501
Flash point 135 °C (275 °F; 408 K) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Occurrence

Isophytol has been in found in two red algae species and more than 15 plant species. Concentrations found have been low.[3]

Synthesis

It can be synthesized in six steps from pseudoionone and propargyl alcohol.[4] Total synthesis begins with the combination of acetylene and acetone to produce 3-methyl-1-butyn-3-ol. Hydrogenation by palladium catalysis results in 3-methyl-1-buten-3-ol. Reaction with diketene or acetic acid ester creates the acetoacetate; thermal reaction leads to 2-methyl-2-hepten-6-one. The steps of adding acetylene and then isopropenyl methyl ether and hydrogenating the product are done twice (this involves an intermediate of pseudoionone); then acetylene is added to create dehydroisophytol. Hydrogenation results in isophytol.[3]

Uses

Production industrially was estimated to be 35000 to 40000 tons in 2002,[5] created by total synthesis, with about 99.9% used in synthesizing vitamin E and vitamin K1. More than 95% of the less than 40 tons used annually in consumer products is as a fragrance. Less than 2 tons a year is used for flavoring.[6]

In perfumes the concentration is 0.2% v/v at most.[7]

Toxicology

Oral LD50 values in mammals are greater than 5000 mg/kg.[8]

See also

References
  1. McGinty, D.; Letizia, C.S.; Api, A.M. (January 2010). "Fragrance material review on isophytol". Food and Chemical Toxicology. 48: S76–S81. doi:10.1016/j.fct.2009.11.015. ISSN 0278-6915. PMID 20141882.
  2. OECD 2003, p. 6.
  3. OECD 2003, p. 7.
  4. Sato, Kikumasa; Kurihara, Yoshie; Abe, Shigehiro (January 1963). "Synthesis of Isophytol". The Journal of Organic Chemistry. 28 (1): 45–47. doi:10.1021/jo01036a009.
  5. OECD 2003, p. 45.
  6. OECD 2003, p. 22.
  7. OECD 2003, p. 12.
  8. OECD 2003, p. 3.

Bibliography
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