Squalene

Squalene
Names
	Preferred IUPAC name (6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaene
Identifiers
CAS Number	111-02-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1728919
ChEBI	CHEBI:15440 ;
ChEMBL	ChEMBL458402 ;
ChemSpider	553635 ;
ECHA InfoCard	100.003.479
EC Number	203-826-1;
IUPHAR/BPS	3054;
KEGG	C00751 ;
MeSH	Squalene
PubChem CID	638072;
RTECS number	XB6010000;
UNII	7QWM220FJH ;
CompTox Dashboard (EPA)	DTXSID0026044 ;
	InChI 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+ Key: YYGNTYWPHWGJRM-AAJYLUCBSA-N ; 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;
	SMILES CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)C;
Properties
Chemical formula	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
Refractive index (nD)	1.4956 (at 20 °C)
Viscosity	12 cP (at 20 °C)
Hazards
NFPA 704 (fire diamond)	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). verify (what is ?) Infobox references

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]

^ CID 1105 from PubChem
^ Merck Index, 11th Edition, 8727
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Abe, Ikuro (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Product Reports. 24 (6): 1311–1331. doi:10.1039/b616857b. PMID 18033581.
^ "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.

[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.

[who.int-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.

[1]

[4]

[2]

[3]

[5]

[6]

[7]

[8]

[9]

[10]

[11]