Structure via PubChem · Public domain (PubChem)
squalene
Sign in to saveAlso known as all-trans-squalene, spinacene, trans-squalene, (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene, (14E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene, (E,E,E,E)-Squalene, (6Z,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene, 2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene
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.
Chemical data
- Formula
- C30H50
- Molecular weight
- 410.7 g/mol
- IUPAC name
- (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
- SMILES
- CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)C
- InChIKey
- YYGNTYWPHWGJRM-AAJYLUCBSA-N
- XLogP
- 11.6
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
6,558 papers- Biological importance and applications of squalene and squalane.Advances in food and nutrition research · 2012
- Squalene-hopene cyclases.Applied and environmental microbiology · 2011
- Squalane and Squalene.International journal of toxicology · 2023
- Squalene: friend or foe for cancers.Current opinion in lipidology · 2019
- Squalene hopene cyclases and oxido squalene cyclases: potential targets for regulating cyclisation reactions.Biotechnology letters · 2023
via PubMed
Wikidata facts
- Mass
- 410.391
Show 5 more facts
- chemical formula
- C₃₀H₅₀
- canonical SMILES
- CC(=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC=C(C)C)C)C)C
- isomeric SMILES
- CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)C
- melting point
- -75
- Commons category
- Squalene
Sources (6)
via Wikidata · CC0
~5 min read
Article
11 sectionsContents
- Role in triterpenoid synthesis
- Production
- Biosynthesis
- Industry
- Shark conservation {{anchor|Shark squalene}}
- Uses
- As an adjuvant in vaccines
- Safety
- Controversies
- References
- External links
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.
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.