Squalene

Source: Wikipedia, the free encyclopedia.
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
IUPHAR/BPS
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).
☒N verify (what is checkY☒N ?)

Squalene is an

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

GlaxoSmithKline adjuvants are called MF59 and AS03, respectively.[11]

Role in triterpenoid synthesis

Squalene is a biochemical precursor to both

NADPH and the migration of the other double bond.[13] In many plants, this is then converted into stigmasterol, while in many fungi, it is the precursor to ergosterol.[citation needed
]

The biosynthetic pathway is found in many bacteria,

eukaryotes, though has not been found in Archaea.[15]

Production

Biosynthesis

Squalene is biosynthesised by coupling two molecules of

squalene synthase
.

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

[[File:
Statin_Pathway_WP430go to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to article
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Statin_Pathway_WP430go to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to article
|alt=Statin pathway edit]]
Statin pathway edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430".

Industry

Synthetic squalene is prepared commercially from geranylacetone.[16]

Shark conservation

In 2020, conservationists raised concerns about the potential slaughter of sharks to obtain squalene for a COVID-19 vaccine.[17]

Environmental and other concerns over shark hunting have motivated its extraction from other sources.[18] Biosynthetic processes use genetically engineered yeast or bacteria.[19][20]

Uses

As an adjuvant in vaccines

See also: AS03 and MF59

Immunologic adjuvants are substances, administered in conjunction with a vaccine, that stimulate the immune system and increase the response to the vaccine. Squalene is not itself an adjuvant, but it has been used in conjunction with surfactants in certain adjuvant formulations.[11]

An adjuvant using squalene is

Ciba-Geigy and Chiron; both companies were subsequently acquired by Novartis.[11] Novartis was later acquired by CSL Bering and created the company Seqirus. It is present in the form of an emulsion and is added to make the vaccine more immunogenic.[11] However, the mechanism of action remains unknown. MF59 is capable of switching on a number of genes that partially overlap with those activated by other adjuvants.[21] How these changes are triggered is unclear; to date, no receptors responding to MF59 have been identified. One possibility is that MF59 affects the cell behaviour by changing the lipid metabolism, namely by inducing accumulation of neutral lipids within the target cells.[22] An influenza vaccine called FLUAD which used MF59 as an adjuvant was approved for use in the US in people 65 years of age and older, beginning with the 2016–2017 flu season.[23]

A 2009

autoimmune diseases; the authors concluded that their data "supports the good safety profile associated with MF59-adjuvated influenza vaccines and suggests there may be a clinical benefit over non-MF59-containing vaccines".[24]

Safety

Toxicology studies indicate that in the concentrations used in cosmetics, squalene has low acute toxicity, and is not a significant contact allergen or irritant.[25][26]

The

US Department of Defense have both published extensive reports that emphasise that squalene is naturally occurring, even in oils of human fingerprints.[11][27] The WHO goes further to explain that squalene has been present in over 22 million flu vaccines given to patients in Europe since 1997 without significant vaccine-related adverse events.[11]

Controversies

Attempts to link squalene to Gulf War syndrome have been debunked.[28][29][30][31]

References

  1. ^ CID 1105 from PubChem
  2. ^ Merck Index, 11th Edition, 8727
  3. S2CID 255032687
    .
  4. doi:10.1002/ange.19760882414
    .
  5. ISSN 2160-3855
    .
  6. PMID 20224687
    .
  7. PMID 32748847
    .
  8. PMID 27604037
    .
  9. S2CID 4221673
    .
  10. PMID 18033581
    .
  11. ^ a b c d e f "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.
  12. PMID 6340956
    .
  13. PMID 27604037
    .
  14. doi:10.1099/00221287-130-5-1137
    .
  15. PMID 32125435
    .
  16. ISBN 978-3527306732
    .
  17. ^ Bowman, Emma (10 October 2020). "A Coronavirus Vaccine Could Kill Half A Million Sharks, Conservationists Warn". National Public Radio.
  18. PMID 35337064
    .
  19. doi:10.1002/ejlt.201100203
    .
  20. PMID 26258173
    .
  21. PMID 18650390
    .
  22. PMID 20018176
    .
  23. ^ "FLUAD, Flu Vaccine With Adjuvant". Centers for Disease Control and Prevention, National Center for Immunization and Respiratory Diseases. 14 December 2017.
  24. PMID 19751689
    .
  25. S2CID 31454284
    .
  26. PMID 19169201
    .
  27. PMID 12136987
    .
  28. ISBN 978-0-30907-178-9
    .
  29. PMID 16960112
    .
  30. ^ "Gulf War illnesses: Questions About the Presence of Squalene Antibodies in Veterans Can Be Resolved" (PDF). U.S. Government Accountability Office. March 1999. Archived from the original (PDF) on 27 February 2021.
  31. ^ Henig, Jess (18 October 2009). "FactCheck: Swine Flu Vaccine Fears Greatly Exaggerated". Newsweek.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Squalene&oldid=1219483474"