Squalane

Squalane

Names
IUPAC name 2,6,10,15,19,23-Hexamethyltetracosane
Other names Perhydrosqualene; Dodecahydrosqualene
Identifiers
CAS Number	111-01-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	776019
ChemSpider	7798 N
ECHA InfoCard	100.003.478
EC Number	203-825-6
KEGG	D05915 N
MeSH	squalane
PubChem CID	8089
RTECS number	XB6070000
UNII	GW89575KF9 Y
InChI InChI=1S/C30H62/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/h25-30H,9-24H2,1-8H3 N Key: PRAKJMSDJKAYCZ-UHFFFAOYSA-N N
SMILES CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C
Properties
Chemical formula	C30H62
Molar mass	422.83 g·mol−1
Appearance	Colorless liquid
Odor	Odorless
Density	810 mg/mL
Melting point	−38 °C (−36 °F; 235 K)
Boiling point	176 °C (349 °F; 449 K) at 7 Pa
Refractive index (nD)	1.452
Thermochemistry
Specific heat capacity (C)	886.36 J/(K·mol)
Std enthalpy of formation (ΔfHo298)	−871.1...−858.3 kJ/mol
Std enthalpy of combustion (ΔcHo298)	−19.8062...−19.7964 MJ/mol
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P305+351+338
Flash point	218 °C (424 °F; 491 K)
Related compounds
Related alkanes	Phytane
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

Squalane is a hydrocarbon derived by hydrogenation of squalene. In contrast to squalene, due to the complete saturation of squalane, it is not subject to auto-oxidation. This fact, coupled with lower costs associated with squalane, make it desirable in cosmetic applications, where it is used as an emollient and moisturizer. The hydrogenation of squalene to produce squalane was first reported in 1916.

Squalene is traditionally sourced from the livers of sharks. Approximately 3000 sharks are required to produce one ton of squalane. At an estimated annual global use for cosmetics of about 2000 tons (2016), this would mean millions of sharks would be required to satisfy global demand. Due to environmental concerns, olive oil and sugarcane as non-animal sources have been developed and commercialized. Other plant sources yielding commercial supply are sunflower and rice, although the latter source only gives mediocre purity (75%). In a biotechnological process, farnesene is produced from fermentation of sugarcane sugars using genetically modified Saccharomyces cerevisiae yeast strains. Farnesene is then dimerized to isosqualene and then hydrogenated to squalane.

Squalane was introduced as an emollient in the 1950s by French company Laserson & Sabetay. The label of squalane as "natural moisturizer" is somewhat exaggerated. While squalane can be found in small quantities in sebaceous secretions (sebum), it is squalene that is most commonly found in nature, most notably in the livers of sharks. Squalane has low acute toxicity and is not an irritant at the concentrations used in cosmetics (up to 100%).