Squalane
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| Names | |
|---|---|
| IUPAC name
2,6,10,15,19,23-Hexamethyltetracosane[1] | |
| Other names
Perhydrosqualene; Dodecahydrosqualene | |
| Identifiers | |
111-01-3  | |
| 776019 | |
| ChemSpider | 7798  |
| EC Number | 203-825-6 |
| Jmol interactive 3D | Image |
| KEGG | D05915 |
| MeSH | squalane |
| PubChem | 8089 |
| RTECS number | XB6070000 |
| UNII | GW89575KF9 |
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| |
| Properties | |
| 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 | |
| 886.36 J/(K·mol) | |
| Std enthalpy of formation (ΔfH |
−871.1...−858.3 kJ/mol |
| Std enthalpy of combustion (ΔcH |
−19.8062...−19.7964 MJ/mol |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | WARNING |
| H315, H319, H335 | |
| P261, P305+351+338 | |
| EU classification (DSD) |
 Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26, S36 |
| 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). | |
| verify (what is ?) | |
| Infobox references | |
Squalane is a hydrocarbon and triterpene derived by hydrogenation of 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.[2] The hydrogenation of squalene was first reported in 1916.[3][4] Squalene is sourced from the livers of sharks. Approximately 3000 sharks are required to produce one ton of squalene.[4] Due to environmental concerns, olive oil as an alternative non-animal source has been developed and commercialized. Another commercial non-animal source is phytosqualane, a compound derived from a farnesene in a sugar-cane sucrose fermentation over genetically modified Sacccharomyces cerevisiae yeast strains.[4] Farnesene is dimerised to isosqualane and then hydrogenated to squalane.
Cosmetics use
Squalane was introduced as a emollient in the 1950s by French company Laserson & Sabetay.[4] 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.[5] Squalane has low acute toxicity and is not an irritant at the concentrations used in cosmetics.[6]
References
- ↑ "squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.
- ↑ "Squalane: the natural moisturizer", by Rosenthal, Maurice L. in Chemistry and Manufacture of Cosmetics (3rd Edition), Editor: Schlossman, Mitchell L. (2002), 3(Bk. 2), 869-875
- ↑ Tsujimoto, M. A highly unsaturated hydrocarbon in shark liver oil. Ind. Eng. Chem. 1916, 8, 889−896.
- 1 2 3 4 Catalytic Hydrogenation of Squalene to Squalane Rosaria Ciriminna, Valerica Pandarus, François Béland, and Mario Pagliaro Organic Process Research & Development Article doi:10.1021/op5002337
- ↑ Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods 19 (1): 87–93. doi:10.1006/meth.1999.0832.
- ↑ "Final report on the safety assessment of squalane and squalene". Journal of the American College of Toxicology 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.
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