Methyl sterculateMethyl sterculate
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Methyl sterculate

Methyl 9,10-methylene octadec-9-enoate; Methyl 2-octyl-1-cyclopropene-1-octanoate

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
Cat# Size Price Qty Buy
1236 25 mg £290.70

Additional Information

Property Value or Rating
Product Size 25 mg
Manufacturer Matreya, LLC
Empirical Formula C20H36O2
CAS# 3220-60-8
Formula Weight 308.5
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 A neat liquid
Storage -20°C
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

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