5-Oxo-octanoic acid

Leete E, Olson JO (1970) 5-Oxo-octanoic acid and 5-oxo-octanal, precursors of coniine. J Chem Soc D 1651... 

The entire skeleton of coniine 6.14) derives from acetate, with labelling of C-2, C-2, C-4, and C-6 by [l- C]acetate. A polyketide pathway immediately seems likely and 5-oxo-octanoic acid 6.11) and the corresponding aldehyde 6.12), with the necessary functionality for inclusion of the nitrogen atom, were shown, by tracer and enzymic evidence, to be implicated in coniine biosynthesis, as was y-coniceine 6.13) which is also a hemlock alkaloid. These results [6, 7] lead in a straightforward way to the pathway shown in Scheme 6.5. Most curiously, however, it has been found that octanoic acid... 

Coniine from the hemlock plant Conium maculatum is a simple example of an alkaloid, although its biosynthesis is unusual. It was thought that coniine would be derived from the amino-acid lysine, but labelled lysine was not converted to coniine. It is unusual in being derived from a type I polyketide (Chapter 4). Both [6- C]-5-oxo-octanoic acid and [6- C]-5-oxo-octanal are well-incorporated into labelled coniine (Figure 9.3). 

Figure 9.3 The route to coniine (in plants) from a tetraketide via 5-oxo-octanoic acid, which twos labelled in the 6-position...

The biological activities of the poison hemlock (Conium maculatum) are due to the content of piperidine alkaloids — coniine (2-propylpiperidine), y-coniceine (2n-propyl-ly-piperidine), conhydrine (2-(l- hydroxypropyl)-piperi-dine), A/-methylc(Miiine (1-methyl-2- propylpiperidine), pseudoconhydrine ((5-hydroxypropyl)-piperidine), conhydrinone ((l-oxo-propyl)-piperidine), W-methylpseudoconhydrine (5-hydroxy-l-methyl-2-propyl-piperidine), and 2-methylpiperidine. The poismiing effect of hemlock supplements by the presence of poly-p-keto acid (2,5,7-tri-oxo-octanoic acid), quercetin, kaempferol, and glycoside dioxymid [4, 12,13, 20, 52, 85, 87]. 

Figure 11.1 Py/methylation GC/MS chromatograms of lead white pigmented linseed oil paint after 610 °C Curie point pyrolysis assisted with on line methylation using 2.5% methanolic TMAH (the sample and TMAH solution was applied onto a rotating Curie point wire pyrolysis time 6 s, interface 180°C). 1, heptenoic acid, methyl ester 2, heptanoic acid, methyl ester 3, butenedioic acid, dimethyl ester 4, butanedioic acid, dimethyl ester 5, octenoic acid, methyl ester 6, octanoic acid, methyl ester 7, pentenedioic acid, dimethyl ester 8, pentanedioic acid, dimethyl ester 9, nonanoic acid, methyl ester 10, hexanedioic acid, dimethyl ester 11, decanoic acid, methyl ester 12, heptanedioic acid, dimethyl ester 13, octanedioic acid, dimethyl ester 14, 1,2 benzenedicarboxylic acid, dimethyl ester 15, a methyl octanedioic acid, dimethyl ester 16, nonanedioic acid, dimethyl ester 17, a methoxy octanedioic acid, dimethyl ester 18, a methyl nonanedioic acid, dimethyl ester 19, a,a dimethyl nonenedioic acid, dimethyl ester 20a, a methyl nonenedioic acid, dimethyl ester 20b, a,a dimethyl nonanedioic acid, dimethyl ester 21, decanedioic acid, dimethyl ester 22, a methoxy nonanedioic acid, dimethyl ester 23, a methyl decan edioic acid, dimethyl ester 24, undecanedioic acid, dimethyl ester 25, a methoxy decan edioic acid, dimethyl ester 26, pentadecanoic acid, methyl ester 27, dodecanedioic acid, dimethyl ester 28, hexadecanoic acid, methyl ester 29, heptadecanoic acid, methyl ester 30, octadecanoic acid, methyl ester 31,8 methoxy 9 octadecenoic acid, methyl ester 32, 11 methoxy 9 octadecenoic acid, methyl ester 33, 9 methoxy 10 octadecenoic acid and 10 methoxy 8 octadecenoic acid 34, 9 oxo octadecanoic acid, 10 oxo octadecanoic acid 35, 9 epoxy octadecanoic acid 36, eicosanoic acid, methyl ester 37, 9,10 dimethoxy octadecanoic acid, methyl ester 38, docosanoic acid, methyl ester. Reprinted from J. Anal. Appl. Pyrol., 61, 1 2, van den Berg and Boon, 19, Copyright 2001, with permission from Elsevier...

Octanoic acid, 4,7-dioxo-, methyl ester [61426-50-4], 56, 39 Octanoic acid, 4-nitro-7-oxo-, methyl ester [61246-51-5], 56, 39... 

Beilstein Handbook Reference) AI3-19341 BRN 1809678 CCRIS 4386 EiNECS 206-397-9 Fluorad FC-26 Hexanoyl fluoride, 3,3,4,4,5,5,6,6,6-nonafluoro-2-oxo- NSC 95114 Octanoic acid, penta-decafluoro- Pentadecafluoro-1-octanoic acid Pentadeca-fluoro-n-octanoic acid Perfluorocaprylic acid Petfluor-octanoic xid Perfluoroheptanecarboxylic acid Per-fluorooctanoic acid PFOA. Intermediate for preparation of monomers and surfactants. Solid mp = 59-60° bp = 192° soluble in H2O (3.4 g/l), organic solvents. 3M Company. 

Hydroxy-1 -octcnyO-f-oxo-1 -piperidincheptanoic acid, H-00371 7- [2-(3-Hydroxy-1 -octcnyl)-5-oxo-1 -pyrroIidinyl]-5-hcptcnoic acid, H-00372 a-Hydroxy-2-octyl-1 -cyclopropene-1 -octanoic acid, see H-00388... 

Oxo-5-(2-pentenylidene)-2-cyclopentene-l-octanoic acid, 9CI. 12-0x0-10,13,15-phytotrienoic acid... 

Hydroxy-4-oxo-5- 2-pentenyl)-1-cycloperitene-1 -octanoic acid. 13-Hydroxy-12-0X0-9,15-phytodienoic acid [81905-33-1]... 

The hydroperoxy epidioxides formed from photosensitized oxidized methyl linoleate are important precursors of volatile compounds, which are similar to those formed from the corresponding monohydroperoxides. Thus, 13-hydroperoxy-10,12-epidioxy-tra 5 -8-enoic acid produces hexanal and methyl lO-oxo-8-decenoate as major volatiles (Figure 4.24). The 9-hydroperoxy-10,12-epidioxy-rrans-13-enoic acid produces 2-heptenal and methyl 9-oxononanoate. Other minor volatile products include two volatiles common to those formed from the monohydroperoxides, pentane and methyl octanoate, and two that are unique, 2-heptanone and 3-octene-2-one. The hydroperoxy epidioxides formed from autoxidized methyl linolenate produce the volatiles expected from the cleavage reactions of linolenate hydroperoxides, and significant amounts of the unique compound 3,5-octadiene-2-one. This vinyl ketone has a low threshold value or minimum detectable level, and may contribute to the flavor impact of fats containing oxidized linolenate (Chapter 5). 

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]... 

Fig. 4.4 Chromatograin of O-trimethylsilylquinoxalinols of standard 2-oxo acids separated on 3 per cent OV-1 on Gas Chrom Q (100-120 mesh) using temperature programming from SO C to 180°C at 2 C min". Peak identifications are 1, pyruvate 2, 2-oxobutyrate 3, 2-oxoisovalerate 4, 2-oxovalerate 5, 2-oxo-3-methylvalerate 6, 2-oxoisocaproate 7, 2-oxo-octanoate 8, 2-oxo-4-methylthiobutyrate 9, 2-oxo-glutarate 10, phenylpyruvate 11,2-oxoadipate. (Redrawn with modifications from Langenbeck et ai. 1975)...

Representatives of the subfamilies Omaliinae and Proteininae (omaliine group) possess an abdominal defensive gland reservoir that opens out between sternite 7 and 8 [ 120]. The multi-component mixtures contained in these glands are used for defence. In Omaliinae and Proteininae the secretion is characterized by mixtures of acids (e.g. 2-methylpropanoic acid, hexanoic acid, 2-octenoic acid, 2-methylbutanoic acid, 3-methylbutanoic acid, butyric acid, and tiglic acid), aldehydes (( )-2-hexenal, heptanal, octanal, nonanal), ketoaldehydes such as 4-oxo-2-hexenal 41 (Scheme 5), 6-methyl-5-hepten-2-one, alcohols (octanol, ( )-2-hexen-l-ol, 2-methylbutan-l-ol), alkanes (nonadecane), esters (2-methylbutyl tiglate 42, various propanoates, 2-hexenyl 3-methylbutanoate, 2-methylbutyl 2-methylbutanoate, octanoates,butanoates), and aromatic compounds (e.g. 2-phenethyl 3-methylbutanoate 43). Unusual compounds are 2-... 

Uses Surfactant in cosmetics Manuf./Distrib. Somerset Cosmetic Co. Variati 4-Ethyl-2-(8-heptadecenyl)-4,5-dlhydro-4-oxazolemethanol 4-Ethyl-2-(8-hepta-decenyl)-2-oxazoline-4-methanol. See Ethyl hydroxymethyl oleyl oxazoline Ethylhexadecyidimethylammonlum bromide. See Cetethyidimonium bromide Ethyl-N-hexadecylmorpholinium ethosulfate Ethyl-4-hexadecylmorpholinium ethyl sulfate. See Cetethyl morphollnlum ethosulfate 2-Ethyl-1-hexaneamine. See 2-Ethylhexylamine 2-Ethylhexanolc acid, 2,2-bis [[(1-oxo-2-ethylhexyl)oxy] methyl]-1,3-pro-panediyl ester. See Pentaerythrityl tetraoctanoate 2-Ethylhexanoic acid, cetyl-stearyl ester. See Cetearyl octanoate 2-Ethylhexanoic acid, 2,2-dimethyl-1,3-propanediyl ester. See Neopentyl glycol dioctanoate... 

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