7-Oxooctanoic acid

The product of Part B of this procedure, methyl 7-oxoheptanoate, has previously been synthesized from cyclohep-tanone in two steps with a 42% overall yield." 7-Oxooctanoic acid, the methyl ester of which is the product of Part C, has been prepared by base-induced ring cleavage of 2-acetylcyclo-hexanone."... 

One of the reported syntheses of ( )-9-oxodec-2-enoic acid 392, the queen substance of the honey bee Apis mellifera, uses two ylide reactions 222). Starting from pimelic acid 385 the resonance-stabilized ylide 386 is prepared by alkylation of methylene-triphenylphosphorane 209 and the former hydrolyzed to 7-oxooctanoic acid 387. Reduction of the corresponding thiol ester 389 and olefination of the resulting aldehyde 390 with phosphorane 67 gives the ( )-2-unsaturated ester 391. The latter was hydrolyzed to pheromone 392 222) (Scheme 69). 

In some cases the intermediate imine is so labile that unwanted by-products are formed before reduction can occur. There are at least two important variations of the reductive amination process that can improve the yield of amine one involves conversion of the aldehyde or ketone to an oxime and the other involves their conversion to a hydrazone. When keto-acid 1.96 was treated with hydrazine, oxime 1.97 was forraed.54 In this approach, a second step was required to convert the oxime to an amine. Catalytic hydrogenation is the most common procedure that is used, as in the reduction of 1.98 to 7-aminooctanoic acid, 1.99. In this particular example, the starting material for this sequence was diketone 1.96, which was cleaved with aqueous hydroxide to give 7-oxooctanoic acid, i.9754 (see chapter two, section 2.1). 

Ketoacids 4-oxopentanoic acid, 5-oxohexanoic add, 6-oxoheptanoic acid, 7-oxooctanoic acid, 8-oxononanoic acid, 9-oxodecanoic acid, 10-oxoundecanoic acid, 11-oxododecanoic acid, 12-oxotridecanoic acid, 2-oxopentanedecanoic acid... 

Butyric acid, octanoic acid, oleic acid, succinic acid, octadecanoic acid, eicosanoic acid, tetracosanoic acid, hexadecanoic acid, 7-oxooctanoic acid, 3-methyl-3-hydroxyglutaric acid, 9,10-dihydroxy-2-decenoic acid, 9,10-dihydroxydodecanoic acid, 9-oxo-2-decenoic acid (9-ODA), 11,12-dihydroxy-2-dodecenoic acid, 13- hydroxy-2-tetradecenoic acid, 2-hydroxyoctanoic acid, 3-methyi-3-hydroxygiutaric acid, 14- hydroxytetradecanoic acid [16] 5,10-Dihydroxydecanoic acid, 8,9-dihydroxydecanoic acid, 3-hydroxydecanedioic acid, 1,12-dodecanedioic acid, 7-hydroxy-2-octenoic acid, 3,10-dihydroxydodecanoic acid, 8-hydroxy-2-octenoic acid, 2-octene-1,8-dioic acid, 8-hydroxy-2-decenoic acid, (Z)-9-hydroxy-2-decenoic acid, ( -9-HDA, 3,9-dihydroxydecanoic acid, 8,9-dihydroxydecanoic acid, 10- hydroxy-2-dodecenoic acid, 11- hydroxy-2-dodecenoic acid, 3-hydroxydecanedioic acid, 1,12-dodecanedioic acid, 10,12-dihydroxydodecanoic acid [16,17]... 

C,5H, CIN0, 63845-29-4) see Indalpine 8-chloro-6-oxooctanoic acid ethyl ester (C10H17CIO3 50628-91-6) see Thioctic acid... 

The protected (5)-4,8-diamino-3-oxooctanoic acid 99 was reduced with NaBH4, the resulting mixture of diastereomers was separated and the (3R,45)-product was derivatized with benzylated DHB (100). Then derivatized o-Ser-Gly was added and the serine OH-group was esterified with the protected OHAsp (101). The Gly carboxyl group was finally set free. 

Capillary gas chromatographic investigation of diastereoisomeric derivatives revealed that in analogy to results obtained without precursors the chiral metabolites are present as mixtures of enantiomers. However for only a few of these compounds the ratios of enantiomers are identical with those determined in pineapple without precursors. The enantiomeric compositions of ethyl 3-hydroxyhexanoate and ethyl 3-acetoxyhexanoate are almost opposite to those determined for the naturally occurring methyl esters. 6-Octalactone obtained after addition of 5-oxooctanoic acid to pineapple tissue is almost optically pure (92% S) on the other hand -octalactone is naturally present in pineapple tissue as nearly racemic mixture (Table 1,8). 

Monochlorodimedone, the substrate used for the detection and isolation of haloperoxidases and perhydrolases (Fig. 16.9-8), and other (3-diketones such as barbituric acid1621 is brominated at the 2-position by all known haloperoxidases and perhydrolases. Oxooctanoic acid and other p-ketoacids form mono- and dihalogen-ated ketones and carbon dioxide1631. When p-alanine and taurine were used as substrates for myeloperoxidase the corresponding N-chloroamines could be detected I64-651. 

Irradiation of 2-oxooctanoic acid 5 in water causes hydrogen abstraction and coupling of the persistent radicals. In this way, a single tailed surfactant is transformed into a double tailed surfactant 6, and this... 

Oxononanoic acid Me ester, in 0-00260 3-Oxooctanoic acid Et ester, in 0-00278... 

Amino-8-oxooctanoic acid, in 0-10014 7-[(3-Amino-3-oxopropyl)hydroxyamino]... 

The main chromophore of isochromenes arises as a hexaketide from activated forms of acetic and malonic acids and the side chain of pigments is derived from 2-oxohexanic and 2-oxooctanoic acids that are synthesised analogously to other fatty acids. 

The aqueous photochemistry of 2-oxooctanoic acid (a single-tailed surfactant) results in the synthesis of a double-tailed surfactant product followed by spontaneous self-assembly into vesicles. The photochemistry mechanism is detailed here, and the reaction products are identified using mass spectrometry. Then, the self-assembled vesicles are characterized using DLS, fluorescence microscopy, and NMR. ... 

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