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Structure Database (LMSD)

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Common Name

Squalene

Systematic Name

Squalene

Synonyms

LM ID

LMPR0106010002

Formula

C₃₀H₅₀

Exact Mass

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410.39125

Status

Curated

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Classification

Biological Context

Squalene is a biosynthetic precursor to all steroids and a terpene originally isolated from shark liver oil.^1,2 Squalene is produced in mammals by condensation of two farnesyl diphosphate molecules by squalene synthase and then oxidized to squalene epoxide for use in the biosynthesis of lanosterol , cholesterol, and other steroids.¹ An oil-in-water emulsion of squalene synergistically increases adaptive immune responses to glucopyranosyl lipid adjuvant (GLA), a toll-like receptor 4 (TLR4) agonist, compared with an aqueous formulation of GLA.³ Formulations containing squalene have been used as adjuvants in vaccines and as hair and skin conditioning agents.

This information has been provided by Cayman Chemical

References

1. Seydoux, E., Liang, H., Dubois Cauwelaert, N., et al. Effective combination adjuvants engage both TLR and inflammasome pathways to promote potent adaptive immune responses. J. Immunol. 201(1), 98-112 (2018).

2. Tansey, T.R., and Shechter, I. Structure and regulation of mammalian squalene synthase. Biochim. Biophys. Acta 1529(1-3), 49-62 (2000).

3. Kubota, B. The chemical composition of squalene. Tokyo Kagaku Kaishi 39, 879-907 (1918).

Reactions

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String Representations

InChiKey (Click to copy)

YYGNTYWPHWGJRM-AAJYLUCBSA-N

InChi (Click to copy)

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+

SMILES (Click to copy)

C(C)(CCC=C(C)C)=CCC/C(/C)=C/CCC=C(C)CCC=C(C)CCC=C(C)C