Not to be confused with squalene.
Squalane
Verifiedfieldschanged
Watchedfieldschanged
Verifiedrevid444116909
Pin2,6,10,15,19,23-Hexamethyltetracosane[1]
OthernamesPerhydrosqualene; Dodecahydrosqualene

Squalane is the organic compound with the formula ((CH3)2CH[CH2]3CH(CH3)[CH2]3CH(CH3)[CH2]2)2. A colorless hydrocarbon, it is the hydrogenated derivative of squalene, although commercial samples are derived from nature.[2] 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.[3]

Sources and production

Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane.[4] 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.[4]

In sugar cane squalane manufacturing, farnesene is produced from fermentation of sugarcane sugars using genetically modified Saccharomyces cerevisiae yeast strains.[4] Farnesene is then dimerized to isosqualene and then hydrogenated to squalane.[4][5]

In olive squalane manufacturing, squalene is extracted from olive oil residues in a green chemistry process, and is then hydrogenated into squalane.[6]

Uses in cosmetics

Squalane was introduced as an emollient in the 1950s.[4] The unsaturated form of squalene is produced in human sebum and the livers of sharks.[7][8] Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.[9][10] In the European Union, Squalane is the standardised INCI name used to declare the ingredient on cosmetic product labels, where it is listed in the European Commission's CosIng inventory with skin-conditioning and emollient functions.[11]

Miscellaneous information

The hydrogenation of squalene to produce squalane was first reported in 1916.[12][4]

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. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  3. ^ Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". Chemistry and Manufacture of Cosmetics. Vol. 3 (Bk. 2). 3rd ed. Schlossman, Mitchell L. (ed.). pp. 869–875.
  4. ^ 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
  5. ^ McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane". Cosmetics & Toiletries. 129 (6)
  6. ^ Rodrigues R.; Pinatel C. (2023). "Upcycled Olive Squalane and Green Chemistry". AZ Cosmetic Ingredients Guide, Expression Cosmétique. ' (2023): 408–412.
  7. ^ Pappas, A (2009). "Epidermal surface lipids". Dermato-endocrinology. 1 (2): 72–76. doi:10.4161/derm.1.2.7811. PMC 2835894. PMID 20224687
  8. ^ Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. PMID 10525443
  9. ^ "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
  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. ^ "Squalane – EU cosmetic ingredient". Cosmadex. Retrieved 2026-05-29. See also the "CosIng entry: Squalane". European Commission.
  12. ^ Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem.. 8 (10): 889–896. doi:10.1021/i500010a005