Methyl sterculate

CATALOG # 1236
Amount 25 mg
Price $325.00
Qty
 
Methyl sterculate
  • Catalog #:1236
  • Scientific Name:Methyl sterculate
  • Common Name:Methyl 9,10-methylene-octadec-9-enoate; Methyl 2-octyl-1-cyclopropene-1-octanoate
  • Empirical Formula:C20H36O2
  • CAS#3220-60-8
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:309
  • Unit:25 mg
  • Solvent:none
  • Source:Natural
  • Purity:98+%
  • Analytical Methods:GC; TLC; identity confirmed by MS
  • Natural Source:Plant
  • Solubility:chloroform, hexane, ethyl ether, methanol
  • Physical Appearance:liquid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    Sterculic acid is a monounsaturated fatty acid containing a cyclopropene ring, which gives it specific and unusual physiological properties. The major sources of sterculic acid are the seed oils of various plants, including Sterculia foetida, cotton, and Bombax munguba. Cyclopropenoids, such as sterculic acid, inhibit the enzyme Δ9-desaturase, preventing the conversion of stearic acid to oleic acid, potentially causing significant health problems for organisms which consume them. Cyclopropenoid fatty acids have been reported to have several deleterious effects on mammals, such as carcinogenicity and acute and chronic toxicity.1,2 Because of the harmful effects of cyclopropenoids, cottonseed oil (a major world-wide edible oil which contains around 1% of these fatty acids) is required to be heat treated and hydrogenated before consumption. Sterculia foetida seeds have been used in traditional Chinese medicine as an anti-parasitic drug and recent research has found that sterculic acid and its methyl ester analog have a significant inhibitory effect towards the wide-spread parasite Toxoplasma gondii.3 Oil from Sterculia foetida has also been shown to have significant insecticide, and possible anti-fungal properties, making it a potentially useful alternative to synthetic, and more environmentally toxic, compounds.4,5

    References:
    1. X. Bao et al., Characterization of cyclopropane fatty-acid synthase from Sterculia foetida, J Biol Chem. vol. 278(15) pp. 12846-12853, 2003
    2. E. Fehling et al., Preparation of malvalic and sterculic acid methyl esters from Bombax munguba and Sterculia foetida seed oils, JAOCS, vol. 75(12), pp. 1757–1760, 1998
    3. P. Hao et al., Sterculic Acid and Its Analogues Are Potent Inhibitors of Toxoplasma gondii, Korean J Parasitol. vol. 54(2) pp. 139–145, 2016
    4. P. Rani and P. Rajasekharreddy, Toxic and antifeedant activities of Sterculia Foetida (L.) seed crude extract against Spodoptera litura (F.) and Achaea Janata (L.) Journal of Biopesticides, vol. 2(2) pp. 161-164 2009
    5. K. Schmid and G. Patterson Effects of cyclopropenoid fatty acids on fungal growth and lipid composition, Lipids, vol. 23(3) pp. 248–252, 1988