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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.[2] The hydrogenation of squalene to produce squalane was first reported in 1916.[3][4]

Squalane
Skeletal formula of squalane
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 203-825-6
KEGG
MeSH squalane
RTECS number XB6070000
UNII
Properties
C30H62
Molar mass 422.83 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
1.452
Thermochemistry
886.36 J/(K·mol)
−871.1...−858.3 kJ/mol
−19.8062...−19.7964 MJ/mol
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
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).
N verify (what is YesYN ?)
Infobox references

Source and productionEdit

Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane.[4] Due to environmental concerns, olive oil, rice and sugarcane as non-animal sources have been commercialized, supplying about 40% of the industry total in 2014.[4] In 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]

Cosmetics useEdit

Squalane was introduced as an emollient in the 1950s.[4] While squalane can be found in small quantities in sebaceous secretions (sebum),[6] it is squalene that is most commonly found in nature, most notably in human sebum and the livers of sharks.[6][7] Squalane has low acute toxicity and is not an irritant at the concentrations used in cosmetics (up to 100%).[8]

ReferencesEdit

  1. ^ "Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012. 
  2. ^ Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". In Schlossman, Mitchell L. Chemistry and Manufacture of Cosmetics. 3 (Bk. 2) (3rd ed.). pp. 869–875. 
  3. ^ Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8: 889–896. doi:10.1021/i500010a005. 
  4. ^ 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. 
  5. ^ McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6). 
  6. ^ a b Pappas, A (2009). "Epidermal surface lipids". Dermato-endocrinology. 1 (2): 72–76. PMC 2835894 . PMID 20224687. 
  7. ^ Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. PMID 10525443. 
  8. ^ "Final report on the safety assessment of squalane and squalene". Journal of the American College of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.