Squalane

Squalane
Names
	IUPAC name 2,6,10,15,19,23-Hexamethyltetracosane[1]
	Other names Perhydrosqualene; Dodecahydrosqualene
Identifiers
CAS Number	111-01-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	776019
ChemSpider	7798 ;
ECHA InfoCard	100.003.478
EC Number	203-825-6;
KEGG	D05915 ;
MeSH	squalane
PubChem CID	8089;
RTECS number	XB6070000;
UNII	GW89575KF9 ;
CompTox Dashboard (EPA)	DTXSID0046513 ;
	InChI 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 Key: PRAKJMSDJKAYCZ-UHFFFAOYSA-N ;
	SMILES CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C;
Properties
Chemical formula	C30H62
Molar mass	422.826 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
Refractive index (nD)	1.452
Viscosity	31.123 mPa·s[2]
Thermochemistry
Heat capacity (C)	886.36 J/(K·mol)
Std enthalpy of; formation (ΔfH⦵298)	−871.1...−858.3 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−19.8062...−19.7964 MJ/mol
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	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).
	verify (what is ?)
	Infobox references

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.[3] The hydrogenation of squalene to produce squalane was first reported in 1916.[4][5]

In basic research, squalane is used as a reference liquid in tribology.[6][7]

Source 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 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][8]

Cosmetics use

Squalane was introduced as an emollient in the 1950s.[5] 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 human sebum and the livers of sharks.[9][10] Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.[11][12]

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References

"Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.
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.
Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". In Schlossman, Mitchell L. (ed.). Chemistry and Manufacture of Cosmetics. 3 (Bk. 2) (3rd ed.). pp. 869–875.
Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8 (10): 889–896. doi:10.1021/i500010a005.
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.
Bair, Scott (2006). "Reference liquids for quantitative elastohydrodynamics: selection and rheological characterization". Tribology Letters. 22 (2): 197–206. doi:10.1007/s11249-006-9083-y. ISSN 1023-8883.
Hecksher, Tina; Olsen, Niels Boye; Dyre, Jeppe C. (2017). "Model for the alpha and beta shear-mechanical properties of supercooled liquids and its comparison to squalane data". The Journal of Chemical Physics. 146 (15): 154504. doi:10.1063/1.4979658. ISSN 0021-9606.
McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6).
Pappas, A (2009). "Epidermal surface lipids". Dermato-endocrinology. 1 (2): 72–76. doi:10.4161/derm.1.2.7811. PMC 2835894. PMID 20224687.
Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. PMID 10525443.
"Final Report on the Safety Assessment of Squalane and Squalene". International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.
"Final Report on the Safety Assessment of Squalane and Squalene" (PDF). International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.

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[1] "Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.

[LalTripathi2000-2] 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] Rosenthal, Maurice L. (2002). "Squalane: the natural moisturizer". In Schlossman, Mitchell L. (ed.). Chemistry and Manufacture of Cosmetics. 3 (Bk. 2) (3rd ed.). pp. 869–875.

[4] Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8 (10): 889–896. doi:10.1021/i500010a005.

[Ciriminna-5] 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] Bair, Scott (2006). "Reference liquids for quantitative elastohydrodynamics: selection and rheological characterization". Tribology Letters. 22 (2): 197–206. doi:10.1007/s11249-006-9083-y. ISSN 1023-8883.

[7] Hecksher, Tina; Olsen, Niels Boye; Dyre, Jeppe C. (2017). "Model for the alpha and beta shear-mechanical properties of supercooled liquids and its comparison to squalane data". The Journal of Chemical Physics. 146 (15): 154504. doi:10.1063/1.4979658. ISSN 0021-9606.

[8] McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6).

[pappas-9] Pappas, A (2009). "Epidermal surface lipids". Dermato-endocrinology. 1 (2): 72–76. doi:10.4161/derm.1.2.7811. PMC 2835894. PMID 20224687.

[10] Allison, Anthony C. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods. 19 (1): 87–93. doi:10.1006/meth.1999.0832. PMID 10525443.

[11] "Final Report on the Safety Assessment of Squalane and Squalene". International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.

[12] "Final Report on the Safety Assessment of Squalane and Squalene" (PDF). International Journal of Toxicology. 1 (2): 37–56. 1982. doi:10.3109/10915818209013146.