A biosynthetic precursor to steroids
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Squalene

Item No. 27058

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene
CAS Number
111-02-4
Synonyms
  • Spinacene
  • trans-Squalene
Molecular Formula
C30H50
Formula Weight
410.7
Purity
≥95%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: miscibleDMSO: miscibleEthanol: miscible
SMILES
C/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C
InChi Code
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+
InChi Key
YYGNTYWPHWGJRM-AAJYLUCBSA-N
Origin
Animal/Shark liver oil
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    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 (Item No. 19521), 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

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

    3. 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).