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 cosmetics manufacturing, where it is used as an emollient and moisturizer. The hydrogenation of squalene to produce squalane was first reported in 1916.
3D model (JSmol)
|Molar mass||422.83 g·mol−1|
|Melting point||−38 °C (−36 °F; 235 K)|
|Boiling point||176 °C (349 °F; 449 K) at 7 Pa|
Refractive index (nD)
Std enthalpy of
Std enthalpy of
|GHS signal word||WARNING|
|H315, H319, H335|
|Flash point||218 °C (424 °F; 491 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Source and productionEdit
Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane. Due to environmental concerns, olive oil, rice and sugarcane as non-animal sources have been commercialized, supplying about 40% of the industry total in 2014. In manufacturing, 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. 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 human sebum and the livers of sharks. Squalane has low acute toxicity and is not an irritant at the concentrations used in cosmetics (up to 100%).
- "Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.
- Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". In Schlossman, Mitchell L. Chemistry and Manufacture of Cosmetics. 3 (Bk. 2) (3rd ed.). pp. 869–875.
- Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8: 889–896. doi:10.1021/i500010a005.
- Ciriminna, Rosaria; Pandarus, Valerica; Béland, François; Pagliaro, Mario (2014). "Catalytic Hydrogenation of Squalene to Squalane". Organic Process Research & Development. 18 (9): 1110–1115. doi:10.1021/op5002337.
- McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6).
- Pappas, A (2009). "Epidermal surface lipids". Dermato-endocrinology. 1 (2): 72–76. PMC . PMID 20224687.
- Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. PMID 10525443.
- "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.