A cyclopropane fatty acid
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Sterculic Acid

Item No. 26735

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-octyl-1-cyclopropene-1-octanoic acid
CAS Number
738-87-4
Synonyms
  • FA 19:2
Molecular Formula
C19H34O2
Formula Weight
294.5
Purity
≥95%
Formulation
A liquid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleEther: solubleHexane: solubleMethanol: soluble
SMILES
CCCCCCCCC1=C(CCCCCCCC(O)=O)C1
InChi Code
InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)
InChi Key
PQRKPYLNZGDCFH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $436

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    Product Description

    Sterculic acid is a cyclopropene fatty acid that has been found in S. foetida.1 It is an inhibitor of Δ9-desaturase that decreases 9(Z)-myristoleic acid (Item No. 9002461) and increases oleic acid (Item No. 90260) and 9(Z),11(E)-conjugated linoleic acid (Item No. 90140) levels in the milk of lactating ewes when administered at a dose of 0.5 g per day.2 It also inhibits endoplasmic reticulum stress induced by 7-keto cholesterol (Item No. 16339) in ARPE-19 cells when used at a concentration of 1 µM and prevents the formation of choroidal neovascularization when applied to eyes at concentrations of 0.1 to 10 mM in a rat model of macular degeneration induced by laser injury.1 Sterculic acid binds to a variety of kinases, including calcium/calmodulin-dependent protein kinase kinase 2 (CAMKK2), mammalian sterile20-related kinase 3 (MST3), and p90 ribosomal S5 kinase 4 (RSK4).3 [Matreya, LLC. Catalog No. 1235]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, J.-D., Amaral, J., Lee, J.W., et al. Sterculic acid antagonizes 7-ketocholesterol-mediated inflammation and inhibits choroidal neovascularization. Biochim. Biophys. Acta 1821(4), 637-646 (2012).

    2. Bichi, E., Toral, P.G., Hervás, G., et al. Inhibition of ∆9-desaturase activity with sterculic acid: Effect on the endogenous synthesis of cis-9 18:1 and cis-9, trans-11 18:2 in dairy sheep. J. Dairy Sci. 95(9), 5242-5252 (2012).

    3. Huang, J.-D., Amaral, J., Lee, J.W., et al. 7-Ketocholesterol-induced inflammation signals mostly through the TLR4 receptor both in vitro and in vivo. PLoS One 9(7), e100985 (2014).