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Sterculic Acid methyl ester Sale

(Synonyms: 9,10-亚甲基油酸甲酯) 目录号 : GC41518

A methyl ester form of sterculic acid

Sterculic Acid methyl ester Chemical Structure

Cas No.:3220-60-8

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产品描述

Sterculic acid methyl ester is an ester form of sterculic acid , which is an inhibitor of δ9 desaturase. Sterculic acid methyl ester (0.75 mM) inhibits the growth of, and is toxic to, the bacteria R. opacus. It decreases the fatty acid content, increases the ratio of palmitate to other fatty acids, and decreases the levels of stearate and oleate in R. opacus when used at concentrations of 0.25 or 0.5 mM. Sterculic acid methyl ester (50 ppm) has a synergistic effect on increased tumor growth induced by aflatoxin Q1 in rainbow trout.

Chemical Properties

Cas No. 3220-60-8 SDF
别名 9,10-亚甲基油酸甲酯
Canonical SMILES CCCCCCCCC1=C(CCCCCCCC(OC)=O)C1
分子式 C20H36O2 分子量 308.5
溶解度 Chloroform: soluble,Ether: soluble,Hexane: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 3.2415 mL 16.2075 mL 32.4149 mL
5 mM 0.6483 mL 3.2415 mL 6.483 mL
10 mM 0.3241 mL 1.6207 mL 3.2415 mL
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Research Update

In vitro effects of sterculic acid on lipid biosynthesis in Rhodococcus opacus strain PD630 and isolation of mutants defective in fatty acid desaturation

FEMS Microbiol Lett 2000 Sep 1;190(1):45-50.PMID:10981688DOI:10.1111/j.1574-6968.2000.tb09260.x.

The in vivo effects of Sterculic Acid methyl ester on triacylglycerol fatty acid composition in the oleaginous, hydrocarbon-degrading bacterium R. opacus strain PD630 was investigated. Sterculic acid, a cyclopropene fatty acid and an inhibitor of the stearoyl-CoA desaturase system, strongly inhibited the synthesis of monoenic fatty acids, of saturated fatty acids with more than 16 carbon atoms and of odd-numbered fatty acids when added to the culture medium. In addition, chemical mutagenesis and the application of the penicillin enrichment technique provided mutants, which were more or less completely impaired in the desaturation of long-chain fatty acids and exhibited in some cases a similar fatty acid composition like the wild-type in the presence of Sterculic Acid methyl ester. The implications of these findings for fatty acid metabolism in R. opacus strain PD630 are discussed.

Membranes of class IIa bacteriocin-resistant Listeria monocytogenes cells contain increased levels of desaturated and short-acyl-chain phosphatidylglycerols

Appl Environ Microbiol 2002 Nov;68(11):5223-30.PMID:12406708DOI:10.1128/AEM.68.11.5223-5230.2002.

A major concern in the use of class IIa bacteriocins as food preservatives is the well-documented resistance development in target Listeria strains. We studied the relationship between leucocin A, a class IIa bacteriocin, and the composition of the major phospholipid, phosphatidylglycerol (PG), in membranes of both sensitive and resistant L. monocytogenes strains. Two wild-type strains, L. monocytogenes B73 and 412, two spontaneous mutants of L. monocytogenes B73 with intermediate resistance to leucocin A (+/-2.4 and +/-4 times the 50% inhibitory concentrations [IC50] for sensitive strains), and two highly resistant mutants of each of the wild-type strains (>500 times the IC50 for sensitive strains) were analyzed. Electrospray mass spectrometry analysis showed an increase in the ratios of unsaturated to saturated and short- to long-acyl-chain species of PG in all the resistant L. monocytogenes strains in our study, although their sensitivities to leucocin A were significantly different. This alteration in membrane phospholipids toward PGs containing shorter, unsaturated acyl chains suggests that resistant strains have cells with a more fluid membrane. The presence of this phenomenon in a strain (L. monocytogenes 412P) which is resistant to both leucocin A and pediocin PA-1 may indicate a link between membrane composition and class IIa bacteriocin resistance in some L. monocytogenes strains. Treatment of strains with Sterculic Acid methyl ester (SME), a desaturase inhibitor, resulted in significant changes in the leucocin A sensitivity of the intermediate-resistance strains but no changes in the sensitivity of highly resistant strains. There was, however, a decrease in the amount of unsaturated and short-acyl-chain PGs after treatment with SME in one of the intermediate and both of the highly resistant strains, but the opposite effect was observed for the sensitive strains. It appears, therefore, that membrane adaptation may be part of a resistance mechanism but that several resistance mechanisms may contribute to a resistance phenotype and that levels of resistance vary according to the type of mechanisms present.

Action of a cyclopropenoid fatty acid on the corpus luteum of pregnant and nonpregnant ewes

Biol Reprod 1994 Feb;50(2):253-7.PMID:8142543DOI:10.1095/biolreprod50.2.253.

The effects of a cyclopropenoid fatty acid on luteal cell function were studied. In experiment 1, pregnant ewes were laparotomized on Day 18 of gestation and ewes with CL in both ovaries were unilaterally ovariectomized. Either 1.09 mg of an extract of Sterculia foetida seeds, containing 750 micrograms Sterculic Acid methyl ester (SA, n = 6), or 1.09 mg oleic acid methyl ester (OA, n = 6) was injected into the artery supplying the ovary bearing CL. Jugular blood was collected on Day 18 before surgery and daily thereafter until Day 30 of gestation or until detection of estrus, whichever occurred first. Serum was assayed for progesterone (P4) by RIA. In experiment 2, CL were removed from ewes on Day 10 of the estrous cycle and slices of luteal tissue were incubated in medium containing 145 ng/ml of S. foetida extract (100 ng/ml SA) or 145 ng/ml OA (control) for 90 min. Then tissue was washed and reincubated in medium containing 25 micrograms 22(R)-hydroxycholesterol/ml or 25 micrograms pregnenolone/ml for 120 min. Tissue plus medium was analyzed for P4. Injection of SA or OA on Day 18 of gestation reduced (p < 0.01) serum levels of P4 within 24 h; concentrations of P4 then remained low, and relatively constant, in six OA control ewes that were pregnant until Day 30 of gestation and in three SA-treated ewes that had nonviable fetuses on Day 30. Serum concentrations of P4 in SA-treated ewes were lower than those of control ewes (p = 0.009). The remaining three ewes injected with SA exhibited estrus within 3 to 5 days after treatment.(ABSTRACT TRUNCATED AT 250 WORDS)