Aliphatic Acids and Esters

Structure 17 with unknown stereochemistry has been proposed (502) for angardianic acid from Leproloma angardianum. If its biosynthesis is similar to that of roccellic acid angardianic acid should have stereo-structure 17a. 

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MCPA (2-methyl, 4-chlorophenoxy aliphatic acids and esters) metaxon, Agroxone, Weedone... 

Mittal L, Mittal JP, Hayon E (1973) Photo-induced decarboxylation of aliphatic acids and esters in solution. Dependence upon state of protonation of the carboxyl group. J Phys Chem 77 1482-1487... 

The positions, numbers, and types of sugars on the anthocyanin molecule influence its bioaccessibility. Indeed, a recent human study reported that the acylation of anthocyaifins resulted in a sigififlcant decrease of anthocyanin recoveries in plasma and urine. In addition, anthocyanins form linkages with aromatic acids, aliphatic acids, and methyl ester derivatives, which can also affect their passage through the intestinal barrier. 

Monofluoroacetic acid offers little promise as a mosquito larvicide, but 2-ethylhexyl monofluoroacetate is a very powerful aphicide. The high toxicity of the fluorinated lower aliphatic acids and their esters to vertebrates probably precludes their use as insecticides except under highly controlled conditions. The toxicity of the fluorinated acids to the vertebrates is attributed to their interference with an enzyme system, but the possibility of finding one with a high specificity for insects is not excluded. 

The repertoire of chemicals that can be used for communication is limited by the biosynthetic ability of the insect. Compared to other insect orders, pheromone biosynthesis in Hymenoptera has received little study [191]. However, the biosynthetic origins of chemically diverse hymenopteran semiochemicals likely include aromatic, fatty acid, and terpenoid pathways as well as simple modifications of host-derived precursors. Notable recent studies include the biosynthesis of the fatty acid components (2 )-9-oxodec-2-enoic acid 52 and (2 )-9-hydroxydec-2-enoic acid of the honeybee queen mandibular pheromone from octadecanoic acid [192,193], and the aliphatic alcohol and ester... 

The gas-phase heats of formation of several enol positive ions of aliphatic aldehydes, ketones, acids, and esters were measured and compared with those of the corresponding keto ions. The enolic ions were found to be thermodynamically more stable by 58-129 kJ moLh This is in marked contrast to the neutral tau-... 

Of numerous other preparations for which nitrile oxides have been invoked as intermediates, one of the most synthetically useful is that developed by Shimizu et al. which employs alkyl esters of a-nitroalkanoic acids as precursors <87BCJ1948). The method is suitable for aliphatic, amide, and ester derivatives, and involves themolysis in an inert solvent to generate the nitrile oxide with con-commitant expulsion of carbon dioxide and alkanol. Other reactions leading to furoxans via nitrile oxides include treatment of a-bromo-a-nitrotoluene with triphenylphosphine <84TL2029), nitrosation... 

Recently, Borhan and coworkers reported the facile oxidation of aliphatic and aromatic aldehydes to acids and esters in DMF or methanol with Oxone (equation 53) . These reactions are considered to be valuable alternatives to traditional metal-mediated oxidations. 

Ferreira V, Jarauta I, Ortega L, Cacho J (2004) Simple strategy for the optimization of solid-phase extraction procedures through the use of solid-liquid distribution coefficients—application to the determination of aliphatic lactones in wine. J Chromatogr A 1025 147 Rettinger K, Karl V, Schmarr HG, Dettmar F, Hener U, Mosandl A (1991) Chirospecific analysis of 2-alkylbranched alcohols, -acids, and -esters chirality evaluation of 2-methylbutanoates from apples and pineapples. Phytochem Anal 2 184... 

Steric effects on the reactivity of benzoic acid derivatives are a little more complicated. The first significant point is that the aromatic carboxylic acids and esters are often some two orders of magnitude less reactive than the corresponding aliphatic compounds. Chapman et al. 7, have explained this difference in terms of three co-operative factors (i) the stabilization of the initial state by delocalization in the case of the aromatic compounds, (ii) inductive electron-withdrawal by the ring, which is significant in esterification... 

Fatty Acids and Their Ethyl Esters. The normal aliphatic acids and their ethyl esters are often the second most abundant group of congeners... 

M 2. —, and W. G. de Pierri Reactivity ratios of vinyl esters of aliphatic acids and some common vinyl monomers. J. Polymer Sci. 27, 39 (1958). 

Amidon et al. [39] have correlated the aqueous solubility of 127 aliphatic hydrocarbons, alcohols, ethers, aldehydes, ketones, fatty acids, and esters with their total molecular surface area ... 

ACETOACTETIC ESTER CONDENSATION. A class of reactions occasioned by the dehydrating power of metallic sodium or sodium ethoxide on the ethyl esters ol monobasic aliphatic acids and a tew other esters. It is best known in the fonuation of acecoacetic ester ... 

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