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Squalene
From Wikipedia, the free encyclopedia
| Squalene | |
|---|---|
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| Systematic name | 2,6,10,15,19,23-hexamethyl- 2,6,10,14,18,22-tetracosahexaene |
| Chemical formula | C30H50 |
| Molecular mass | 410.71 g/mol |
| CAS number | [111-02-4] |
| Density | 0.855 g/cm3 |
| Melting point | -100 °C |
| Boiling point | 285 °C at 25 mmHg |
| SMILES | CC(C)=CCCC(C)=CCCC(C)=CC CC=C(C)CCC=C(C)CCC=C(C)C |
| Disclaimer and references | |
Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanic sources as well, including amaranth seed, rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene.
Squalene is the biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids.
Squalene is a low density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the shark's liver, is lighter than water with a specific gravity of 0.855.
Recently it has become a trend for sharks to be hunted to process their livers for the purpose of making squalene health capsules. However, there is little clinical evidence to prove that, taken internally, squalene does anything to increase an individual's quality of life.
Squalene is used in cosmetics as a natural, oil-free moisturizer. It also makes up 12% of sebum, a natural product expressed by human sebaceous glands to moisturize hair follicles.
- Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene - by squalene synthase;
