A cyclopropane fatty acid
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cis-9,10-Methyleneoctadecanoic Acid

Item No. 24824

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2S)-rel-2-octyl-cyclopropaneoctanoic acid
CAS Number
4675-61-0
Synonyms
  • Dihydrosterculic Acid
  • FA 19:1
Molecular Formula
C19H36O2
Formula Weight
296.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC(CCCCCCC[C@H](C1)[C@H]1CCCCCCCC)=O
InChi Code
InChI=1S/C19H36O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h17-18H,2-16H2,1H3,(H,20,21)/t17-,18+/m0/s1
InChi Key
PDXZQLDUVAKMBQ-ZWKOTPCHSA-N
Side Chain Carbon Sum
19:0
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $283

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    Product Description

    cis-9,10-Methyleneoctadecanoic acid is a cyclopropane fatty acid that has been found in bacteria and the digestive gland of P. globosa.1,2,3 It is a component of S. aureus cell membranes and levels decrease upon treatment with carvacrol.2 cis-9,10-Methyleneoctadecanoic acid is secreted by H. pylori and enhances histamine- and dibutyryl cAMP-stimulated acid secretion in isolated guinea pig parietal cells.4 It also activates protein kinase C (PKC) in a calcium-dependent manner. [Matreya, LLC. Catalog No. 1822]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ramachandran, H., Shafie, N.A.H., Sudesh, K., et al. Cupriavidus malaysiensis sp. nov., a novel poly(3-hydroxybutyrate-co-4-hydroxybutyrate) accumulating bacterium isolated from the Malaysian environment. Antonie Van Leeuwenhoek 111(3), 361-372 (2018).

    2. Wang, L.-H., Wang, M.-S., Zeng, X.-A., et al. Membrane destruction and DNA binding of Staphylococcus aureus cells induced by carvacrol and its combined effect with a pulsed electric field. J. Agric. Food Chem. 64(32), 6355-6363 (2016).

    3. Misra, K.K., Shkrob, I., Rakshit, S., et al. Variability in fatty acids and fatty aldehydes in different organs of two prosobranch gastropod mollusks. Biochem. System. Ecol. 30(8), 749-761 (2002).

    4. Beil, W., Birkholz, C., Wagner, S., et al. Helicobacter pylori fatty acid cis 9,10-methyleneoctadecanoic acid increases [Ca2+]i, activates protein kinase C and stimulates acid secretion in parietal cells. Prostaglandins Leukot. Essent. Fatty Acids 59(2), 119-125 (1998).