Squalane
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Names | |
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Preferred IUPAC name
2,6,10,15,19,23-Hexamethyltetracosane[1] | |
Other names
Perhydrosqualene; Dodecahydrosqualene
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Identifiers | |
3D model (JSmol)
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776019 | |
ChemSpider | |
ECHA InfoCard | 100.003.478 ![]() |
EC Number |
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KEGG | |
MeSH | squalane |
PubChem CID
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RTECS number |
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UNII | |
CompTox Dashboard (EPA)
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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)
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1.452 |
Viscosity | 31.123 mPa·s[2] |
Thermochemistry | |
Heat capacity (C)
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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
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H315, H319, H335 |
P261, P305+351+338 | |
Flash point | 218 °C (424 °F; 491 K) |
Related compounds | |
Related alkanes
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Phytane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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 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]
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] The unsaturated form squalene is produced 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.
- ^ Jump up to: a b c d e f 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. S2CID 137651135.
- ^ 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. arXiv:1701.05086. doi:10.1063/1.4979658. ISSN 0021-9606. PMID 28433033. S2CID 24743379.
- ^ 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. S2CID 31454284.
- ^ "Final Report on the Safety Assessment of Squalane and Squalene" (PDF). International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146. S2CID 31454284.
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