Squalane

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Not to be confused with squalene.
Squalane
Skeletal formula of squalane
Names
IUPAC name
2,6,10,15,19,23-Hexamethyltetracosane[1]
Other names
Perhydrosqualene; Dodecahydrosqualene
Identifiers
111-01-3 YesY
776019
ChemSpider 7798 N
EC Number 203-825-6
Jmol 3D model Interactive image
KEGG D05915 N
MeSH squalane
PubChem 8089
RTECS number XB6070000
UNII GW89575KF9 YesY
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
Irritant Xi
R-phrases R36/37/38
S-phrases S26, S36
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

Squalane is a hydrocarbon and triterpene derived by hydrogenation of squalene. A recent method has reported 100% conversion of squalene to squalane using palladium nanoparticle intercalated natural clay (prepared from local sand of Jodhpur, Rajasthan, India) heterogeneous catalyst reported by Sharma and coworkers under solvent free conditions.The clay based catalysts are highly stable and recyclable.[2] 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.[3] The hydrogenation of squalene was first reported in 1916.[4][5] Squalene is sourced from the livers of sharks. Approximately 3000 sharks are required to produce one ton of squalene.[5] Due to environmental concerns, olive oil as an alternative non-animal source has been developed and commercialized. Another commercial non-animal source is phytosqualane, a compound derived from a farnesene in a sugar-cane sucrose fermentation over genetically modified Sacccharomyces cerevisiae yeast strains.[5] Farnesene is dimerised to isosqualane and then hydrogenated to squalane.

Cosmetics use[edit]

Squalane was introduced as a emollient in the 1950s by French company Laserson & Sabetay.[5] 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.[6] Squalane has low acute toxicity and is not an irritant at the concentrations used in cosmetics.[7]

References[edit]

  1. ^ "squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012. 
  2. ^ "Palladium-Nanoparticles-Intercalated Montmorillonite Clay: A Green Catalyst for the Solvent-Free Chemoselective Hydrogenation of Squalene" Vineet K Soni and Rakesh K Sharma, ChemCatChem (2016),8,1763-1768 http://onlinelibrary.wiley.com/doi/10.1002/cctc.201600210/abstract
  3. ^ "Squalane: the natural moisturizer", by Rosenthal, Maurice L. in Chemistry and Manufacture of Cosmetics (3rd Edition), Editor: Schlossman, Mitchell L. (2002), 3(Bk. 2), 869-875
  4. ^ Tsujimoto, M. A highly unsaturated hydrocarbon in shark liver oil. Ind. Eng. Chem. 1916, 8, 889−896.
  5. ^ a b c d Catalytic Hydrogenation of Squalene to Squalane Rosaria Ciriminna, Valerica Pandarus, François Béland, and Mario Pagliaro Organic Process Research & Development Article doi:10.1021/op5002337
  6. ^ Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. 
  7. ^ "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.