Squalene

Squalene

Names
Systematic 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 Y
3D model (Jmol)	Interactive image
3DMet	B00166
Beilstein Reference	1728919
ChEBI	CHEBI:15440 Y
ChEMBL	ChEMBL458402 Y
ChemSpider	553635 Y
ECHA InfoCard	100.003.479
EC Number	203-826-1
IUPHAR/BPS	3054
KEGG	C00751 N
MeSH	Squalene
PubChem	638072
RTECS number	XB6010000
UNII	7QWM220FJH Y
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+ Y Key: YYGNTYWPHWGJRM-AAJYLUCBSA-N Y 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	410.73 g·mol−1
Appearance	Pale yellow, translucent liquid
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
Viscosity	12 cP (at 20 °C)
Hazards
NFPA 704	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).
N  (what is YN ?)
Infobox references

Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives. Yeast cells have been genetically engineered to produce commercially useful quantities of "synthetic" squalene.

All plants and animals produce squalene as a biochemical intermediate, including humans. It occurs in high concentrations in the stomach oil of birds in the order Procellariiformes.

Squalene is a hydrocarbon and a triterpene, and is a natural and vital part of the synthesis of all plant and animal sterols, including cholesterol, steroid hormones, and vitamin D in the human body.

Squalene is the biochemical precursor to the whole family of steroids. 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.

Squalene is an ancient molecule. In plants, squalene is the precursor to stigmasterol. In certain fungi, it is the precursor to ergosterol. However, blue-green algae and some bacteria do not manufacture squalene, and must acquire it from the environment if they need it.