Squalene

Squalene
Names
	Preferred IUPAC name (6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaene
Identifiers
CAS Number	111-02-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1728919
ChEBI	CHEBI:15440 ;
ChEMBL	ChEMBL458402 ;
ChemSpider	553635 ;
ECHA InfoCard	100.003.479
EC Number	203-826-1;
IUPHAR/BPS	3054;
KEGG	C00751 ;
MeSH	Squalene
PubChem CID	638072;
RTECS number	XB6010000;
UNII	7QWM220FJH ;
CompTox Dashboard (EPA)	DTXSID0026044 ;
	InChI InChI=1S/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+ Key: YYGNTYWPHWGJRM-AAJYLUCBSA-N ; 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;
	SMILES CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)C;
Properties
Chemical formula	C30H50
Molar mass	410.730 g·mol−1
Appearance	Colourless oil
Density	0.858 g·cm−3
Melting point	−5 °C (23 °F; 268 K)
Boiling point	285 °C (545 °F; 558 K) at 3.3 kPa
log P	12.188
Refractive index (nD)	1.4956 (at 20 °C)
Viscosity	12 cP (at 20 °C)
Hazards
NFPA 704 (fire diamond)	1 1 0
Flash point	110 °C (230 °F; 383 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Squalene is an organic compound. It is a triterpene with the formula C₃₀H₅₀. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as Squalus is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection.

Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria.

Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively.