Squalane

Source: Wikipedia, the free encyclopedia.
Not to be confused with squalene.
Squalane
Skeletal formula of squalane
Names
Preferred IUPAC name
2,6,10,15,19,23-Hexamethyltetracosane[1]
Other names
Perhydrosqualene; Dodecahydrosqualene
Identifiers
3D model (
JSmol
)
776019
ChemSpider
ECHA InfoCard
 100.003.478 Edit this at Wikidata
EC Number
  • 203-825-6
KEGG
MeSH squalane
RTECS number
  • XB6070000
UNII
  • 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 ☒N
    Key: PRAKJMSDJKAYCZ-UHFFFAOYSA-N ☒N
  • CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C
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
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:
GHS07: Exclamation mark
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 their standard state (at 25 °C [77 °F], 100 kPa).
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Squalane is the

emollient and moisturizer in cosmetics.[4]

Sources and production

Squalene was traditionally sourced from the livers of

sugar cane have been commercialized, and as of 2014 have been supplying about 40% of the industry total.[5]

In sugar cane squalane manufacturing,

dimerized to isosqualene and then hydrogenated to squalane.[5][6]

In olive squalane manufacturing, squalene is extracted from olive oil residues thanks to green chemistry processes, and is then hydrogenated into squalane.[7]

Uses in cosmetics

Squalane was introduced as an emollient in the 1950s.[5] The unsaturated form 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

  1. ^ "Squalane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 15 March 2012.
  2. ISSN 0021-9568
    .
  3. 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.
  5. ^
    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)
  8. PMID 20224687
    .
  9. PMID 10525443
    .
  10. S2CID 31454284
    .
  11. S2CID 31454284
    .
  12. doi:10.1021/i500010a005
    .
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