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Squalene

Not to be confused with squalane.
Squalene
Skeletal formula of squalene
Spacefill 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[1]
Identifiers
3D model (JSmol)
3DMet
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)[4]
Boiling point 285 °C (545 °F; 558 K) at 3.3 kPa[2]
log P 12.188
1.4956 (at 20 °C) [3]
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).
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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.[5] Squalene has a role in topical skin lubrication and protection.[6]

Most plants, fungi, and animals produce squalene as biochemical precursor in sterol biosynthesis, including cholesterol and steroid hormones in the human body.[7][8][9] It is also an intermediate in the biosynthesis of hopanoids in many bacteria.[10]

Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively.[11]

  1. ^ CID 1105 from PubChem
  2. ^ Merck Index, 11th Edition, 8727
  3. ^ Pabst, Florian; Blochowicz, Thomas (December 2022). "On the intensity of light scattered by molecular liquids - Comparison of experiment and quantum chemical calculations". The Journal of Chemical Physics. 157 (24): 244501. Bibcode:2022JChPh.157x4501P. doi:10.1063/5.0133511. PMID 36586992. S2CID 255032687.
  4. ^ Ernst, Josef; Sheldrick, William S.; Fuhrhop, Juergen H. (December 1976). "Crystal structure of squalene". Angewandte Chemie (in German). 88 (24): 851. doi:10.1002/ange.19760882414.
  5. ^ Ronco, Alvaro L.; De Stéfani, Eduardo (20 December 2013). "Squalene: a multi-task link in the crossroads of cancer and aging". Functional Foods in Health and Disease. 3 (12): 462–476. doi:10.31989/ffhd.v3i12.30. ISSN 2160-3855.
  6. ^ Pappas, A (1 April 2009). "Epidermal surface lipids". Dermato-Endocrinology. 1 (2). Taylor & Francis: 72–76. doi:10.4161/derm.1.2.7811. PMC 2835894. PMID 20224687.
  7. ^ Micera, Marco; Botto, Alfonso; Geddo, Federica; Antoniotti, Susanna; Bertea, Cinzia Margherita; Levi, Renzo; Gallo, Maria Pia; Querio, Giulia (2 August 2020). "Squalene: More than a Step toward Sterols". Antioxidants. 9 (8): 688. doi:10.3390/antiox9080688. PMC 7464659. PMID 32748847.
  8. ^ Cerqueira, Nuno M. F. S. A.; Oliveira, Eduardo F.; Gesto, Diana S.; Santos-Martins, Diogo; Moreira, Cátia; Moorthy, Hari N.; Ramos, Maria J.; Fernandes, P. A. (4 October 2016). "Cholesterol Biosynthesis: A Mechanistic Overview". Biochemistry. 55 (39): 5483–5506. doi:10.1021/acs.biochem.6b00342. PMID 27604037.
  9. ^ ZANDEE, DI (27 June 1964). "Absence of Sterol Synthesis in some Arthropods". Nature. 202 (4939): 1335–6. Bibcode:1964Natur.202.1335Z. doi:10.1038/2021335a0. PMID 14210972. S2CID 4221673.
  10. ^ Abe, Ikuro (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Product Reports. 24 (6): 1311–1331. doi:10.1039/b616857b. PMID 18033581.
  11. ^ "Squalene-based adjuvants in vaccines". Global Advisory Committee on Vaccine Safety. World Health Organization. 21 July 2006. Archived from the original on November 4, 2012.
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