squalane
{{Distinguish|squalene}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444116909
| ImageFile = Squalan.svg
| ImageFile_Ref =
| ImageName = Skeletal formula of squalane
| PIN = 2,6,10,15,19,23-Hexamethyltetracosane{{Cite web|title=Squalane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8089&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=15 March 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}
| OtherNames = Perhydrosqualene; Dodecahydrosqualene
|Section1={{Chembox Identifiers
| CASNo = 111-01-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8089
| ChemSpiderID = 7798
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| UNII = GW89575KF9
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-825-6
| KEGG = D05915
| KEGG_Ref = {{keggcite|changed|kegg}}
| 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 = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PRAKJMSDJKAYCZ-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}}
|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
}}
|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 = {{GHS exclamation mark}}
| GHSSignalWord = WARNING
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|305+351+338}}
| FlashPtC = 218
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = Phytane
}}
}}
Squalane is the organic compound with the formula {{chem2|((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.{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }} 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.{{cite book | chapter = Squalane: the natural moisturizer | author = Rosenthal, Maurice L. | title = Chemistry and Manufacture of Cosmetics | edition = 3rd | editor = Schlossman, Mitchell L. | date = 2002 | volume = 3 (Bk. 2) | pages = 869–875}}
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.{{cite journal | url = http://www.centerchem.com/Customer-Content/www/News/PDFs/CT1407_RenewableEmollientfromSugarcane-Amyris.pdf | journal = Cosmetics & Toiletries | year = 2014 | volume = 129 | issue = 6 | title = Deriving Renewable Squalane from Sugarcane | vauthors = McPhee D, Pin A, Kizer L, Perelman L}}
In olive squalane manufacturing, squalene is extracted from olive oil residues in a green chemistry process, and is then hydrogenated into squalane.{{Cite journal |last=Rodrigues R. ; Pinatel C. |date=2023 |title=Upcycled Olive Squalane and Green Chemistry |url=https://en.expression-cosmetique.fr/boutique?Category=AZ%2520Cosmetic%2520Ingredients%2520Guide%2520 |journal=AZ Cosmetic Ingredients Guide, Expression Cosmétique |issue=2023 |pages=408–412}}
Uses in cosmetics
Squalane was introduced as an emollient in the 1950s. The unsaturated form of squalene is produced in human sebum and the livers of sharks.{{cite journal|pmc=2835894 |year=2009 |last1=Pappas |first1=A |title=Epidermal surface lipids |journal=Dermato-endocrinology |volume=1 |issue=2 |pages=72–76 |pmid=20224687 |doi=10.4161/derm.1.2.7811}}{{cite journal|author= Allison, Anthony C.| title=Squalene and Squalane Emulsions as Adjuvants|journal=Methods|year=1999|volume=19|pages=87–93| doi=10.1006/meth.1999.0832| pmid=10525443|issue= 1}} Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.{{cite journal | title = Final Report on the Safety Assessment of Squalane and Squalene | journal = International Journal of Toxicology | year = 1982 | volume = 1 | issue = 2 | pages = 37–56 | doi = 10.3109/10915818209013146 | s2cid = 31454284 | doi-access = free }}{{cite journal | title = Final Report on the Safety Assessment of Squalane and Squalene | journal = International Journal of Toxicology | year = 1982 | volume = 1 | issue = 2 | pages = 37–56 | url = http://www.beauty-review.nl/wp-content/uploads/2014/08/Final-Report-on-the-Safety-Assessment-of-Squalane-and-Squalene.pdf | doi = 10.3109/10915818209013146 | s2cid = 31454284 }}
Miscellaneous information
The hydrogenation of squalene to produce squalane was first reported in 1916.{{cite journal | author = Tsujimoto, M. | title = A highly unsaturated hydrocarbon in shark liver oil | journal = Ind. Eng. Chem. | date = 1916 | volume = 8| issue = 10 | pages = 889–896 | doi=10.1021/i500010a005| url = https://zenodo.org/record/1428710 }}{{Cite journal | doi = 10.1021/op5002337| title = Catalytic Hydrogenation of Squalene to Squalane| journal = Organic Process Research & Development| volume = 18| issue = 9| pages = 1110–1115| year = 2014| last1 = Ciriminna| first1 = Rosaria| last2 = Pandarus| first2 = Valerica| last3 = Béland| first3 = François| last4 = Pagliaro| first4 = Mario|url=https://www.academia.edu/14200386}}