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Some residual unchanged fatty acid may remain, but this elutes well ahead of the product when this is subjected to GC analysis. Indeed, the adduct adds substantially to the molecular weight of the original ester, and tends to elute at a temperature about 40°C higher than the latter from a GC column containing a non-polar silicone phase. As I explained earlier, the reaction is especially useful for chromatogram monoenoic chromatogram fatty acids. The mass spectrum of the dimethyl disulphide (DMDS) adduct of methyl oleate gives an abundant molecular ion, then cleavage occurs between the carbons that originally constituted the chromatogram double bond to yield two substantial fragment ions that serve to locate it. The procedure has been used to identify a large number of monoenoic fatty acids from natural sources, including, branched-chain, 2-methoxy and 2-hydroxy monounsaturated fatty acids in addition to more conventional monoenes. Adduct formation has been shown to be entirely stereospecific, presumably by trans addition, so that threo- and erythro- derivatives are formed from cis- and trans-isomers respectively.
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