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Squalane

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Not to be confused with squalene.
Squalane
Skeletal formula of squalane
Names
Preferred IUPAC name 2,6,10,15,19,23-Hexamethyltetracosane
Other names Perhydrosqualene; Dodecahydrosqualene
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 776019
ChemSpider
ECHA InfoCard 100.003.478 Edit this at Wikidata
EC Number
  • 203-825-6
KEGG
MeSH squalane
PubChem CID
RTECS number
  • XB6070000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H62/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h25-30H,9-24H2,1-8H3Key: PRAKJMSDJKAYCZ-UHFFFAOYSA-N
SMILES
  • CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C
Properties
Chemical formula C30H62
Molar mass 422.826 g·mol
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
Thermochemistry
Heat capacity (C) 886.36 J/(K·mol)
Std enthalpy of
formation (ΔfH298) 		−871.1...−858.3 kJ/mol
Std enthalpy of
combustion (ΔcH298) 		−19.8062...−19.7964 MJ/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P305+P351+P338
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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.

Sources and production

Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane. 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.

In sugar cane squalane 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.

In olive squalane manufacturing, squalene is extracted from olive oil residues in a green chemistry process, and is then hydrogenated into squalane.

Uses in cosmetics

Squalane was introduced as an emollient in the 1950s. The unsaturated form of squalene is produced in human sebum and the livers of sharks. Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.

Miscellaneous information

The hydrogenation of squalene to produce squalane was first reported in 1916.

References

  1. "Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.
  2. 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.
  3. Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  4. 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.
  5. ^ 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.
  6. McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6).
  7. 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)
  8. Pappas, A (2009). "Epidermal surface lipids". Dermato-endocrinology. 1 (2): 72–76. doi:10.4161/derm.1.2.7811. PMC 2835894. PMID 20224687.
  9. Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. PMID 10525443.
  10. "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.
  11. "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.
  12. Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8 (10): 889–896. doi:10.1021/i500010a005.
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