Squalane
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.[3] The hydrogenation of squalene to produce squalane was first reported in 1916.[4][5]
![]() | |
Names | |
---|---|
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 pictograms | ![]() |
GHS Signal word | Warning |
GHS hazard statements |
H315, H319, H335 |
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). | |
![]() ![]() ![]() | |
Infobox references | |
In basic research, squalane is used as a reference liquid in tribology.[6][7]
Source 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 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][8]
Cosmetics use
Squalane was introduced as an emollient in the 1950s.[5] 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.[9][10] Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.[11][12]
References
- "Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.
- Lal, Krishan; Tripathi, Neelima; Dubey, Gyan P. (2000). "Densities, Viscosities, and Refractive Indices of Binary Liquid Mixtures of Hexane, Decane, Hexadecane, and Squalane with Benzene at 298.15 K". Journal of Chemical & Engineering Data. 45 (5): 961–964. doi:10.1021/je000103x. ISSN 0021-9568.
- Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". In Schlossman, Mitchell L. (ed.). 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 (10): 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.
- Bair, Scott (2006). "Reference liquids for quantitative elastohydrodynamics: selection and rheological characterization". Tribology Letters. 22 (2): 197–206. doi:10.1007/s11249-006-9083-y. ISSN 1023-8883.
- Hecksher, Tina; Olsen, Niels Boye; Dyre, Jeppe C. (2017). "Model for the alpha and beta shear-mechanical properties of supercooled liquids and its comparison to squalane data". The Journal of Chemical Physics. 146 (15): 154504. doi:10.1063/1.4979658. ISSN 0021-9606.
- 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. doi:10.4161/derm.1.2.7811. PMC 2835894. 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". International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.
- "Final Report on the Safety Assessment of Squalane and Squalene" (PDF). International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.