Methyl suberate

Extension by three carbon atoms is possible with methyl glutarate [183], by the isoprene unit with ethyl 3-methyl adipate [184], by four carbon atoms with methyl adipate [143], by five carbon atoms with methyl pimelate [185] and by six carbon atoms with methyl suberate [186]. A series of branched -fluorocarboxylic acids were prepared by cross-coupling with oo-fluorocarboxylic acids [187]. For further examples see Tables 6, 7. 

Crossed coupling has also been applied to the extension of the carbon chain in fatty acids. Extension by two carbon atoms is achieved with succinate half esters,whereby separation problems can be simplified by using the benzyl half ester.Expansion by the propane unit has been accomplished with methyl glutarate, ° by the isoprene unit with ethyl 3-methyladipate, by four carbons with methyl adipate, by the pentane unit with methyl pimelate, and by six carbon atoms with methyl suberate. 

Methyl esters of dibasic carboxylic acids >dimethyl suberate (usually have a series of peaks at m/zs 84, 98, 112, 126, 140, etc.)... 

Removal of the aliphatic materials by hydrogenolysis leaves a residue that contains low amounts of polymethylenic components, suggesting that the suberized material contains some aliphatic components not susceptible to cleavage by such methods [3]. On the other hand, removal of suberin from cork cell wall preparations was examined by CPMAS and the results showed that the aliphatic components were nearly completely removed from this suberin preparation as the spectra showed that the residual material was virtually devoid of methyl... 

Octanoicacid Suberic acid methyl ester dlmeth 1... 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

An intersecting RCM is the alkyne variant called ring closing alkyne metathesis (RCAM). In this case, two alkynes, usually methyl terminated, are converted to the cycloalkyne. Unlike RCM, RCAM does not produce geometric isomers. Using this methodology, several constrained diamino-suberic analogues can be produced (Scheme 28.15).45... 

II (Lower-index inert component) Cyclohexyl methacrylate Ethylene glycol dimethacrylate Dimethyl suberate Benzoin methyl ether 1.0 ml 0.12 ml 0.25 ml 0.06 g Monomer Crosslinking monomer Inert Initiator 1.505 -1.5 1.4326... 

In known metabolic states and disorders, the nature of metabolites excreted at abnormal levels has been identified by GC-MS. Examples of this are adipic and suberic acids found in urine from ketotic patients [347], 2-hydroxybutyric acid from patients with lactic acidosis [348], and methylcitric acid (2-hydroxybutan-l,2,3-tricarboxylic acid) [349] in a case of propionic acidemia [350,351]. In the latter instance, the methylcitric acid is thought to be due to the condensation of accumulated propionyl CoA with oxaloacetate [349]. Increased amounts of odd-numbered fatty acids present in the tissues of these patients due to the involvement of the propionyl CoA in fatty acid synthesis, have also been characterised [278]. A deficiency in a-methylacetoacetyl CoA thiolase enzyme in the isoleucine pathway prevents the conversion of a-methylacetoacetyl CoA to propionyl CoA and acetyl CoA [352,353]. The resultant urinary excretion of large amounts of 2-hydroxy-3-methylbutanoic acid (a-methyl-/3-hydroxybutyric acid) and an excess of a-methylacetoacetate and often tiglyl glycine are readily detected and identified by GC-MS. 

Electrolysis of a methanol solution of methyl oxalate with ethylene under pressure yielded 70-90% of the dimethyl esters of succinic, adipic, suberic, and sebacic acids. Decrease in the ethylene pressure or increase of the current density led to a decrease in the higher esters in the product mixture [241]. The influence of mechanism and kinetic data on yields and selectivities in addition reactions of anodically generated radicals to olefins has been calculated and predictions have been tested in preparative electrolyses [244]. 

Succinic add Methyl-sucdnic acid Adipic add Pimelic add Suberic add... 

Poly(ethylene suberate) 200.23 Poly(o-methyl styrene) 118.18... 

Disuccinimidyl suberate, a cross-linking agent, has been synthesized and used to probe the insulin-responsive D-glucose transport of the rat adipocyte. Incubation of cells with the reagent blocked methyl-a-D-glucopyranoside transport without affecting either basal hexose transport or simple diffusion as indicated by uptake in the presence of cytochalasin B. 

Kohn [23] Tyrosine Desamino tyrosine Succinic acid, glutaric acid, diglycolic acid, adipic acid, 3-methyl adipic acid, suberic acid, dioxaoctanedioic acid, or sebacic acid Methanol, ethanol, isopropanol, butanol, isobutanol, sec-butanol, hexanol, octanol, dodecyl, or phenol... 

Styryl methyl ketone. See Benzylidene acetone Styryl oxide. See Styrene oxide Styvex 40007 BKL2. See Acrylonitrile/butadiene/styrene copolymer Suberic acid... 

The only thorough characterization of mixtures of depolymerized suberin components (dep-suberin) was carried out by us in a comprehensive investigation of this material. The opaque pasty samples were obtained by the alkaline methanolysis of Quercus suber L. cork [8,76]. Under the conditions used for the depolymerization, most of the carboxylic acid functions were therefore converted into the corresponding methyl esters. 

Alicyclic polyamides (poly cy do amides) result from l,4-bis(amino methyl)cyclohexane and aliphatic dicar boxy lie acids, e.g., suberic acid. They possess lower water absorption and better electrical insulation properties than aliphatic polyamides. They are used for injection-molded articles, often reinforced with 20-40% by wt of glass fiber. 

Heptanedioic acid Di-Me ester, in H-10027 Methyl hydrogen suberate, in 0-10014... 

Scheme 13.4. In the upper part, a representation of the oxidation of tropine to an N-methyl-pyrrolidinedioic acid (tropinic acid) and the subsequent production of piperylenedicarboxylic acid and pimelic acid (heptanedioic acid). In the lower part, a representation of the electrolytic conversion of glutaric acid (pentanedioic acid) to suberic acid (octanedioic acid) and carbon dioxide (CO2) and thence to cycloheptanone and, in two different ways, to cycloheptene.

Pimelic acid, a-methyl valeric acid Suberic acid, methyl hexanoic acid Decane-l,10-dicarboxylic acid Dodecane-1,12-dicarboxylic add Tetradecane-l,14-dicarboxylic acid... 

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