16694-31-8Relevant articles and documents
NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids
Afri, Michal,Alexenberg, Carmit,Aped, Pinchas,Bodner, Efrat,Cohen, Sarit,Ejgenberg, Michal,Eliyahu, Shlomi,Gilinsky-Sharon, Pessia,Harel, Yifat,Naqqash, Miriam E.,Porat, Hani,Ranz, Ayala,Frimer, Aryeh A.
, p. 119 - 128 (2014)
In our companion paper, we described the preparation and intercalation of two homologous series of dicarbonyl compounds, methyl n-oxooctadecanoates and the corresponding n-oxooctadecanoic acids (n = 4-16), into DMPC liposomes. 13C NMR chemical shift of the various carbonyls was analyzed using an ET(30) solvent polarity-chemical shift correlation table and the corresponding calculated penetration depth (in A?). An iterative best fit analysis of the data points revealed an exponential correlation between ET(30) micropolarity and the penetration depth (in A?) into the liposomal bilayer. However, this study is still incomplete, since the plot lacks data points in the important area of moderately polarity, i.e., in the ET (30) range of 51- 45.5 kcal/mol. To correct this lacuna, a family of ketophospholipids was prepared in which the above n-oxooctadecanoic acids were attached to the sn-2 position of a phosphatidylcholine with a palmitic acid chain at sn-1. To assist in assignment and detection several derivatives were prepared 13C-enriched in both carbonyls. The various homologs were intercalated into DMPC liposomes and give points specifically in the missing area of the previous polarity-penetration correlation graph. Interestingly, the calculated exponential relationship of the complete graph was essentially the same as that calculated in the companion paper based on the methyl n-oxooctadecanoates and the corresponding n-oxooctadecanoic acids alone. The polarity at the midplane of such DMPC systems is ca. 33 kcal/mol and is not expected to change very much if we extend the lipid chains. This paper concludes with a chemical ruler that maps the changing polarity experienced by an intercalant as it penetrates the liposomal bilayer.
Preparation method of delta-stearolactone
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Paragraph 0019; 0020, (2016/11/14)
The invention relates to a preparation method of delta-stearolactone. The preparation method comprises that at a temperature of 70-80 DEG C, 1, 3-cyclohexanedione, bromododecane, potassium hydroxide and a small amount of a catalyst methyl trioctyl ammonium chloride undergo a reaction in a methylbenzene solvent according to a mole ratio of 1: 1: 7.5: 1 to produce a diketone compound I, the diketone compound I undergoes a reflux reaction in a sodium hydroxide aqueous solution with a concentration of 10% for 30h, the reaction product is cooled to the room temperature and then is acidized so that 5-oxooctadecanoic acid is obtained, the 5-oxooctadecanoic acid is reduced through sodium borohydride in ethanol at a temperature of 30-35 DEG C, the reduction product is treated and undergoes a dilute hydrochloric acid cyclisation reaction to produce a delta-stearolactone crude product and the delta-stearolactone crude product is recrystallized through n-hexane so that delta-stearolactone solids are obtained. 1, 3-cyclohexanedione and bromododecane undergo a reaction to produce delta-stearolactone. The preparation method has the advantages that 1, raw materials are easily available and cheap, 2, operation is simple, reaction steps are less and the preparation method can be industrialized, 3, a yield is high, product quality is good and a fragrance is good.
Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.
, p. 5188 - 5197 (2013/09/02)
Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 μM).
