Squalane is the organic compound with the formula ((CH3)2CH(CH2)3CH(CH3)(CH2)3(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]
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| Names | |
|---|---|
| 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)
|
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: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P305+P351+P338 | |
| 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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Sources and production
editSqualene 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
editSqualane was introduced as an emollient in the 1950s.[5] The unsaturated form of squalene is produced in human sebum and the livers of sharks.[8][9] Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.[10][11]
Miscellaneous information
editThe hydrogenation of squalene to produce squalane was first reported in 1916.[12][5]
References
edit- ^ "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.
- ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
- ^ Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". In Schlossman, Mitchell L. (ed.). Chemistry and Manufacture of Cosmetics. Vol. 3 (Bk. 2) (3rd ed.). pp. 869–875.
- ^ 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.
- ^ McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6).
- ^ Rodrigues R. ; Pinatel C. (2023). "Upcycled Olive Squalane and Green Chemistry". AZ Cosmetic Ingredients Guide, Expression Cosmétique (2023): 408–412.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ 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.
- ^ Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8 (10): 889–896. doi:10.1021/i500010a005.