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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 cosmetic applications, 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)
{{{Beilstein}}}
ChemSpider
ECHA InfoCard 100.003.478
EC Number 203-825-6
KEGG
MeSH [www.nlm.nih.gov/cgi/show_data.php?acc={{{MeSH}}} {{{MeSH}}}]
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 is traditionally sourced from the livers of sharks. Approximately 3000 sharks are required to produce one ton of squalane.[4] At an estimated annual global use for cosmetics of about 2000 tons (2016), this would mean millions of sharks would be required to satisfy global demand. Due to environmental concerns, olive oil and sugarcane as non-animal sources have been developed and commercialized. Other plant sources yielding commercial supply are sunflower [5] and rice, although the latter source only gives mediocre purity (75%).[6] In a biotechnological process, 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.[7]

Cosmetics useEdit

Squalane was introduced as an emollient in the 1950s by French company Laserson & Sabetay.[4] The label of squalane as "natural moisturizer" is somewhat exaggerated. While squalane can be found in small quantities in sebaceous secretions (sebum), it is squalene that is most commonly found in nature, most notably in the livers of sharks.[8] Squalane has low acute toxicity and is not an irritant at the concentrations used in cosmetics (up to 100%).[9]

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 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. ^ WO2010004193A1 https://www.google.com/patents/WO2010004193A1?cl=en&hl=de
  6. ^ http://www.oryza.co.jp/html/english/pdf/Squalane2.0M.pdf
  7. ^ Derek McPhee, Armelle Pin, Lance Kizer, and Loren Perelman (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6). 
  8. ^ Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. PMID 10525443. doi:10.1006/meth.1999.0832. 
  9. ^ "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.