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Isophytol
Chemical compound From Wikipedia, the free encyclopedia
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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]
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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]
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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
See also
References
Bibliography
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