Squalane

Squalane
Names
	Preferred IUPAC name 2,6,10,15,19,23-Hexamethyltetracosane
	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
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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). verify (what is ?) Infobox references

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]

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

^ "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.
^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ 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.
^ ^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.
^ McPhee D, Pin A, Kizer L, Perelman L (2014). "Deriving Renewable Squalane from Sugarcane" (PDF). Cosmetics & Toiletries. 129 (6).
^ 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)
^ 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. S2CID 31454284.
^ "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.
^ Tsujimoto, M. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem. 8 (10): 889–896. doi:10.1021/i500010a005.

[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.

[KO-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.

[Ciriminna-5] ^ ^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.

[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)

[pappas-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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