 | |
| Names | |
|---|---|
| Preferred IUPAC name 2,6,10,15,19,23-Hexamethyltetracosane[1] | |
| Other names Perhydrosqualene; Dodecahydrosqualene | |
| Identifiers | |
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3D model (JSmol) | |
| 776019 | |
| ChemSpider |
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| ECHA InfoCard | 100.003.478 |
| EC Number |
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| KEGG |
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| MeSH | squalane |
| RTECS number |
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| UNII | |
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| Properties | |
| 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 | |
| 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: | |
 | |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Squalane is theorganic compound with the formula((CH3)2CH(CH2)3CH(CH3)(CH2)3(CH2)3CH(CH3)(CH2)2)2. A colorless hydrocarbon, it is thehydrogenated derivative ofsqualene, although commercial samples are derived from nature.[3] In contrast to squalene, due to the completesaturation of squalane, it is not subject toauto-oxidation. This fact, coupled with its lower costs and desirable physical properties, led to its use as anemollient andmoisturizer incosmetics.[4]
Squalene was traditionally sourced from the livers ofsharks, with approximately 3000 required to produce one ton of squalane.[5] Due to environmental concerns, other sources such asolive oil, rice andsugar 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 fromfermentation of sugarcane sugars using genetically modifiedSaccharomyces cerevisiaeyeast strains.[5]Farnesene is thendimerized toisosqualene and thenhydrogenated to squalane.[5][6]
In olive squalane manufacturing, squalene is extracted from olive oil residues in agreen chemistry process, and is then hydrogenated into squalane.[7]
Squalane was introduced as an emollient in the 1950s.[5] The unsaturated form ofsqualene 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]
Thehydrogenation ofsqualene to produce squalane was first reported in 1916.[12][5]
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