Squalane
Chemical compound
From Wikipedia, the free encyclopedia
Squalane is the organic compound with the formula ((CH3)2CH[CH2]3CH(CH3)[CH2]3CH(CH3)[CH2]2)2. A colorless hydrocarbon, it is the hydrogenated derivative of squalene, although commercial samples are derived from nature.[3] In contrast to squalene, due to the complete saturation of squalane, it is not subject to auto-oxidation. This fact, coupled with its lower costs and desirable physical properties, led to its use as an emollient and moisturizer in cosmetics.[4]
 | |
| Names | |
|---|---|
| Preferred IUPAC name
2,6,10,15,19,23-Hexamethyltetracosane[1] | |
| Other names
Perhydrosqualene; Dodecahydrosqualene | |
| Identifiers | |
3D model (JSmol) |
|
| 776019 | |
| ChemSpider | |
| ECHA InfoCard | 100.003.478 |
| EC Number |
|
| KEGG | |
| MeSH | squalane |
PubChem CID |
|
| RTECS number |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C30H62 | |
| Molar mass | 422.826 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 |
| Viscosity | 31.123 mPa·s[2] |
| Thermochemistry | |
Heat capacity (C) |
886.36 J/(K·mol) |
Std enthalpy of formation (ΔfH⦵298) |
−871.1...−858.3 kJ/mol |
Std enthalpy of combustion (ΔcH⦵298) |
−19.8062...−19.7964 MJ/mol |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H315, H319, H335 | |
| P261, P305+P351+P338 | |
| 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).
| |
Sources and production
Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane.[5] Due to environmental concerns, other sources such as olive oil, rice and sugar cane have been commercialized, and as of 2014 have been supplying about 40% of the industry total.[5]
In sugar cane squalane manufacturing, farnesene is produced from fermentation of sugarcane sugars using genetically modified Saccharomyces cerevisiae yeast strains.[5] Farnesene is then dimerized to isosqualene and then hydrogenated to squalane.[5][6]
In olive squalane manufacturing, squalene is extracted from olive oil residues in a green chemistry process, and is then hydrogenated into squalane.[7]
Uses in cosmetics
Miscellaneous information
The hydrogenation of squalene to produce squalane was first reported in 1916.[12][5]