Isophytol is a

terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes ...

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

that is used as a fragrance and as an intermediate in the production of

vitamin E Vitamin E is a group of eight fat soluble compounds that include four tocopherols and four tocotrienols. Vitamin E deficiency, which is rare and usually due to an underlying problem with digesting dietary fat rather than from a diet low in vitami ...

and K₁.

Occurrence

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

Synthesis

It can be synthesized in six steps from pseudoionone and

propargyl alcohol Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most pol ...

Total synthesis Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes i ...

begins with the combination of

acetylene Acetylene ( systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pur ...

and

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

to produce 3-methyl-1-butyn-3-ol.

Hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate org ...

by palladium catalysis results in 3-methyl-1-buten-3-ol. Reaction with

diketene Diketene is an organic compound with the molecular formula , and which is sometimes written as . It is formed by dimerization of ketene, . Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a color ...

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.

Uses

Production industrially was estimated to be 35000 to 40000 tons in 2002, created by total synthesis, with about 99.9% used in synthesizing

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

Toxicology

Oral values in mammals are greater than 5000 mg/kg.

References

Bibliography

*{{cite report, url = http://www.chem.unep.ch:80/irptc/sids/OECDSIDS/505328.pdf, archive-url = https://web.archive.org/web/20120328182240/http://www.chem.unep.ch/irptc/sids/OECDSIDS/505328.pdf, url-status = dead, archive-date = 28 March 2012, author = OECD, author-link = OECD, publisher =

UNEP The United Nations Environment Programme (UNEP) is responsible for coordinating responses to environmental issues within the United Nations system. It was established by Maurice Strong, its first director, after the United Nations Conference on ...