Squalene

Chembox new
Name = Squalene
ImageFile = Squalene.svg
ImageSize = 350px
ImageName = Skeletal formula of squalene
IUPACName = 2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene
Section1 = Chembox Identifiers
CASNo = 111-02-4
SMILES = CC(C)=CCCC(C)=CCCC(C) =CCCC=C(C)CCC=C(C) CCC=C(C)C
InChI=1/C30H50/c1-25(2)
15-11-19-29(7)23-13-
21-27(5)17-9-10-18-
28(6)22-14-24-30(8)
20-12-16-26(3)4/h15-
18,23-24H,9-14,19-
22H2,1-8H3/b27-17+,
28-18+,29-23+,30-24+
Section2 = Chembox Properties
Formula = C₃₀H₅₀
MolarMass = 410.71 g/mol
Density = 0.855 g/cm³
MeltingPt = -100 °C
BoilingPt = 285 °C at 25 mmHg

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.

Squalane is a saturated form of squalene in which the double bonds have been eliminated by hydrogenation. Because it is less susceptible to oxidation, it is more commonly used in personal care products than squalene.

Role in steroid synthesis

Squalene is the biochemical precursor to the whole family of steroids. [K. Bloch:"Sterol structure and membrane function","CRC Crit. Rev.",14:47-92.] Oxidation (via squalene monooxygenase) 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.

Shark squalene

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. Environmental and other concerns over shark hunting have motivated its extraction from vegetable sources instead. [EWG: [http://www.enviroblog.org/2008/02/unilever-takes-a-bite-out-of-y-1.htm Unilever takes a bite out of your face cream] ]

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.

A study linking squalene, as experimental vaccine adjuvant, to individuals with the clinical signs of Gulf War syndrome was published in 2002. The published findings strongly suggest that the squalene contaminated vaccines could be responsible for the GulfWar Syndrome symptoms seen in the study group, and recommended that a large scale epidemiological study be performed to verify or correct this. [ [http://www.avip2001.net/OfficialDocuments_files/Asa_squalene.pdf Antibodies to Squalene in Recipients of Anthrax Vaccine] Experimental and Molecular Pathology 73, 19–27, 2002] Despite repeated assurances that the vaccine was safe and necessary, a U.S. Federal Judge ruled that there was good cause to believe it was harmful, and he ordered the Pentagon to stop administering it in October 2004. [ [http://web.archive.org/web/20061111154918/http://www.marinecorpstimes.com/story.php?f=1-292925-1412120.php Marine Corps Times - News - More News ] ]

Use as a moisturizer

Squalene is used in cosmetics as a natural moisturizer. It penetrates the skin quickly, does not leave a greasy feeling on the skin and blends well with other oils and vitamins.

Biosynthesis

* Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene - by "squalene synthase".

References