10152-62-2Relevant articles and documents
The newly synthesized linoleic acid derivative FR236924 induces a long-lasting facilitation of hippocampal neurotransmission by targeting nicotinic acetylcholine receptors
Tanaka, Akito,Nishizaki, Tomoyuki
, p. 1037 - 1040 (2003)
The newly synthesized linoleic acid derivative, FR236924, induces a long-lasting facilitation of hippocampal neurotransmission based on a persistent enhancement in the activity of presynaptic nicotinic ACh receptors via a PKC pathway and the ensuing increase in glutamate release, not only in vitro but in vivo at a low dosage (2 mg/kg, ip), which suggested the possibility of its use as a promising anti-dementia drug.
Preparation of fatty acid methyl esters for gas-liquid chromatography
Ichihara, Ken'Ichi,Fukubayashi, Yumeto
, p. 635 - 640 (2010)
A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45°C overnight or heated at 100°C for 1-1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be 1.4%. The yields of FAMEs were ≥96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/ methylation using commercial anhydrous HCl/ methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC. Copyright
New family of cyclopropanating reagents: Synthesis, reactivity, and stability studies of iodomethylzinc phenoxides
Charette, Andre B.,Francoeur, Sebastien,Martel, Jonathan,Wilb, Nicole
, p. 4539 - 4542 (2000)
A valuable alternative to the traditional Simmons-Smith reagents is offered by the title compounds, as a result of their ease of preparation and high reactivities towards unfunctionalized olefins (see scheme).
FLUORINE SUBSTITUENT EFFECTS ON BIO-METHYLENATION OF OLEFINIC FATTY ACIDS
Buist, Peter H.,Findlay, Judy M.
, p. 1433 - 1436 (1984)
A homoallylic fluoro substituent retards the rate of biological methylation of olefinic fatty acids.
Synthesis of dihydrosterculic acid-based monoglucosyl diacylglycerol and its analogues and their biological evaluation
Srikanth, Vudhgiri,Prasad,Poornachandra,Phani Babu,Ganesh Kumar,Jagadeesh,Jala, Ram Chandra Reddy
, p. 134 - 145 (2016)
In the present study, Lactobacillus plantarum glycolipid (GL1) molecule in β-configuration and its fatty acid analogues were synthesized using trichloroacetimidate methodology. The β-configuration of the GL1 molecule was unambiguously assigned by NMR studies using 2D-ROESY (NOE) and J-coupling analysis. Dihydrosterculic acid was synthesized using Furukawa's reagent and the selective esterification of dihydrosterculic acid at C-3 position of glycerol was achieved with EDC-HCl at 0 °C. In vitro cytotoxicity of the GL1 molecule and its fatty acid analogues was evaluated against DU145, A549, SKOV3 and MCF7 cell lines. Among all the synthesized molecules, the GL1 molecule and compound 7d showed moderate activity, while the compound 7b showed promising activity against all the tested cell lines with IC50 values of 20.1, 18.2, 19.1 and 17.6 ?1/4M, respectively. In addition, all tested compounds showed poor cytotoxicity against normal HUVEC cells. The MCF7 cells when treated with compound 7b showed lower bromodeoxyuridine incorporation levels as compared to untreated cells, suggesting that the compound 7b was highly effective and inhibited the cell proliferation. In addition, the compounds showed significant increase in caspases 3 and 9 levels by inducing apoptosis in MCF 7 cells.
Synergistic effect of additives on cyclopropanation of olefins
Cheng, Donghao,Huang, Deshun,Shi, Yian
, p. 5588 - 5591 (2013)
An efficient cyclopropanation of olefins with Zn(CH2I) 2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates,
Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids
Kwan, Man-Lung,Mirjafari, Arsalan,McCabe, John R.,O'Brien, Richard A.,Essi IV, David F.,Baum, Leah,West, Kevin N.,Davis, James H.
, p. 12 - 14 (2013/02/22)
Cyclopropyl moieties embedded in the long aliphatic side chains of imidazolium-type ionic liquids are shown to be highly effective in lowering the Tm of such materials relative to counterparts bearing linear, saturated side chains. While not as efficient as olefins in bringing about this effect, ILs incorporating side-chain cyclopropanated modules are likely to be more resistant to aerobic degradation than those employing the former.
Ultrasound in Lipids. Furan Formation under Ultrasonic assisted Simmons-Smith Reaction and the Effect of Cadmium and Copper as Zinc Replacers
Lie, Marcel S. F.,Jie, Ken,Lam, Wilson L. K.
, p. 1460 - 1461 (2007/10/02)
Methyl 12-oxo-octadec-9-cis-enoate gave methyl 9,12-epoxyoctadeca-9,11-dienoate when treated with zinc or cadmium in the presence of di-iodomethane and 1,2-dimethoxyethane under concomitant ultrasonic irradiation, while under similar conditions copper caused cyclopropanation across the ethylenic bond in methyl oleate and ricinoleate.
A facile, versatile procedure for the preparation of fatty acid esters suitable for glc or hplc analyses
Grossert, J. Stuart,Ratnayake, W. M. Nimal,Swee, Tiw
, p. 2617 - 2620 (2007/10/02)
The preparation of fatty acid methyl esters for glc analyses and of various aryl esters for hplc analyses has traditionally been carried out in totally unrelated operations.This paper draws attention to the use of fatty acid-trifluoroacetic acid mixed anhydrides which may be directly and efficiently converted into either type of esters.The utility of the method was demonstrated by the preparation of series of methyl, 2-naphthyl, and vanillin fatty acid esters.The spectral characterization of some aryl fatty acid esters is recorded.
