Squalane

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title: "Squalane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["triterpenes", "alkanes"] topic_path: "general/triterpenes" source: "https://en.wikipedia.org/wiki/Squalane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444116909 | ImageFile = Squalan.svg | ImageFile_Ref = | ImageName = Skeletal formula of squalane | PIN = 2,6,10,15,19,23-Hexamethyltetracosane | OtherNames = Perhydrosqualene; Dodecahydrosqualene |Section1={{Chembox Identifiers | CASNo = 111-01-3 | CASNo_Ref = | PubChem = 8089 | ChemSpiderID = 7798 | ChemSpiderID_Ref = | UNII = GW89575KF9 | UNII_Ref = | EINECS = 203-825-6 | KEGG = D05915 | KEGG_Ref = | MeSHName = squalane | RTECS = XB6070000 | Beilstein = 776019 | SMILES = CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C | StdInChI = 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 | StdInChI_Ref = | StdInChIKey = PRAKJMSDJKAYCZ-UHFFFAOYSA-N | StdInChIKey_Ref = |Section2={{Chembox Properties | C=30 | H=62 | Appearance = Colorless liquid | Odor = Odorless | Density = 810 mg/mL | MeltingPtC = -38 | BoilingPtC = 176 | BoilingPt_notes = at 7 Pa | RefractIndex = 1.452 | Viscosity = 31.123 mPa·s |Section3={{Chembox Thermochemistry | DeltaHf = −871.1...−858.3 kJ/mol | DeltaHc = −19.8062...−19.7964 MJ/mol | HeatCapacity = 886.36 J/(K·mol) |Section4={{Chembox Hazards | GHSPictograms = | GHSSignalWord = WARNING | HPhrases = | PPhrases = | FlashPtC = 218 |Section5={{Chembox Related | OtherFunction_label = alkanes | OtherFunction = Phytane

Squalane is the organic compound with the formula . A colorless hydrocarbon, it is the hydrogenated derivative of squalene, although commercial samples are derived from nature. 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.

Sources and production

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

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

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

Uses in cosmetics

Squalane was introduced as an emollient in the 1950s. Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.

Miscellaneous information

The hydrogenation of squalene to produce squalane was first reported in 1916.

References

References

  1. (26 March 2005). "Squalane - Compound Summary". National Center for Biotechnology Information.
  2. (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.
  3. (2006). "Kirk-Othmer Encyclopedia of Chemical Technology".
  4. Rosenthal, Maurice L.. (2002). "Chemistry and Manufacture of Cosmetics".
  5. link. Cosmetics & Toiletries. (2014). "Deriving Renewable Squalane from Sugarcane"
  6. Rodrigues R.; Pinatel C.. (2023). "Upcycled Olive Squalane and Green Chemistry". AZ Cosmetic Ingredients Guide, Expression Cosmétique.
  7. (2009). "Epidermal surface lipids". Dermato-endocrinology.
  8. Allison, Anthony C.. (1999). "Squalene and Squalane Emulsions as Adjuvants". Methods.
  9. (1982). "Final Report on the Safety Assessment of Squalane and Squalene". International Journal of Toxicology.
  10. (1982). "Final Report on the Safety Assessment of Squalane and Squalene". International Journal of Toxicology.
  11. Tsujimoto, M.. (1916). "A highly unsaturated hydrocarbon in shark liver oil". Ind. Eng. Chem..
  12. (2014). "Catalytic Hydrogenation of Squalene to Squalane". Organic Process Research & Development.

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