Squalane

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Squalane
Skeletal formula of squalane Squalan.svg
Skeletal formula of squalane
Names
Preferred 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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-825-6
KEGG
MeSH squalane
PubChem CID
RTECS number
  • XB6070000
UNII
  • 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,9-24H2,1-8H3 X mark.svgN
    Key: PRAKJMSDJKAYCZ-UHFFFAOYSA-N X mark.svgN
  • CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C
Properties
C30H62
Molar mass 422.826 g·mol−1
AppearanceColorless 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
Viscosity 31.123 mPa·s [2]
Thermochemistry
886.36 J/(K·mol)
−871.1...−858.3 kJ/mol
−19.8062...−19.7964 MJ/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
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 [77 °F], 100 kPa).
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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. [3] 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. [4]

Contents

Sources and production

Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane. [5] 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. [5]

In sugar cane squalane manufacturing, farnesene is produced from fermentation of sugarcane sugars using genetically modified Saccharomyces cerevisiae yeast strains. [5] Farnesene is then dimerized to isosqualene and then hydrogenated to squalane. [5] [6]

In olive squalane manufacturing, squalene is extracted from olive oil residues in a green chemistry process, and is then hydrogenated into squalane. [7]

Uses in cosmetics

Squalane was introduced as an emollient in the 1950s. [5] The unsaturated form of squalene is produced in human sebum and the livers of sharks. [8] [9] Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer. [10] [11]

Miscellaneous information

The hydrogenation of squalene to produce squalane was first reported in 1916. [12] [5]

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. 1 2 3 4 5 6 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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