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Squalene

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Squalene is a widely used ingredient in cosmetics, personal care, and skincare formulations. Depending on its function, it may serve as a moisturizer, preservative, emulsifier, or active ingredient to enhance the overall effectiveness and performance of a product.

Squalene (Wikipedia)
Not to be confused with squalane.

Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as Squalus is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection.

Squalene
Skeletal formula of squalene
Skeletal formula of squalene
Spacefill model of squalene
Spacefill model of squalene
Ball and stick model of squalene
Ball and stick model of squalene
Names
Preferred IUPAC name
(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaene
Identifiers
3D model (JSmol)
1728919
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.479 Edit this at Wikidata
EC Number
  • 203-826-1
KEGG
MeSH Squalene
RTECS number
  • XB6010000
UNII
  • InChI=1S/C30H50/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/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+ checkY
    Key: YYGNTYWPHWGJRM-AAJYLUCBSA-N checkY
  • InChI=1/C30H50/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/h15-18,23-24H,9-14,19-22H2,1-8H3
  • CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)C
Properties
C30H50
Molar mass 410.730 g·mol−1
Appearance Colourless oil
Density 0.858 g·cm−3
Melting point −5 °C (23 °F; 268 K)
Boiling point 285 °C (545 °F; 558 K) at 3.3 kPa
log P 12.188
1.4956 (at 20 °C)
Viscosity 12 cP (at 20 °C)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria.

Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively.

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