3- -2-octenoic acid

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...

Figure 11.2 Py/silylation GC/MS chromatograms of aged linseed oil pyrolysed in the pre sence of HMDS, (a) Pyrogram obtained with a microfurnace pyrolyser pyrolysis temperature 600 °C furnace pressure 14 psi purge flow 0.5 ml min (b) Pyrogram obtained with a resistively heated filament pyrolyser pyrolyser interface I80°C transfer line 300°C valve oven 290°C. 1, Hexenoic acid, trimethylsilyl ester 2, hexanoic acid, trimethylsilyl ester 3, heptenoic acid, trimethylsilyl ester 4, heptanoic acid, trimethylsilyl ester 5, octenoic acid, trimethylsilyl ester 6, octanoic acid, trimethylsilyl ester 7, nonenoic acid, trimethylsilyl ester 8, nonanoic acid, trimethylsilyl ester 9, decanoic acid, trimethylsilyl ester 10, lauric acid, trimethylsilyl ester 11, suberic acid, trimethylsilyl diester 12, azelaic acid, trimethylsilyl diester 13, myristic acid, trimethylsilyl ester 14, sebacic acid, trimethylsilyl diester 15, palmitic acid, trimethylsilyl ester 16, stearic acid, trimethylsilyl ester...

Example Miller and Rich investigated the conformational consequences of substitution s on an amino acid in cyclosporin A. an importan t iininunosnppressive dnig. One of th e ammo acids iii this cyclic iin decapeptide is (2.v, ir. 4r, 5f )-3-nydroxy-4-methyl-2-(methylamino)-6-octenoic acid (MeBmtli. It is essential for biological activitv. 

Miller, KE. Rich, D.H. Molecular Mechanics Calculations of Cyclosporin A Analogues. Effect of Chirality and Degree of Substitution on the Side-Chain Conformations of (2s, 3r, 4r, 6e)-3-Hydroxy-4-methyl-2-(methylamino)-6-octenoic Acid and Related Derivatives. 

This type of yvn-seleclivc aldol addition has been applied in the synthesis of the unusual L-threonine based amino acid, (2,S, 3/ ,6F)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid, of cyclosporine104, of the cyclic hexapeptide echinocandin105, and of the antibiotic ionomycin97. 

ETHYL-2-METHYL-2-OCTENOIC ACID (2-Octenoic acid, 4-ethyl-2-methyl-)... 

Ethyl-2-methyl-2-octenoic acid has been prepared only by this method. An alternate synthesis of a-alkyl-a,fl-unsaturated adds proceeds via a-bromination of the saturated acid, followed by dehy-drohalogenation with quinoline at elevated temperatures.11 The present method is especially well adapted to preparation of a/y-dialkyl-a,j3-unsaturated acids. 

Dissolve 100 g malonic acid in 360 g dry pyridine and heat 48-52° C for forty hours with 100 g n-hexaldehyde (n-capronaldehyde) or homolog. Cool in ice bath and with good stirring add dropwise 150 ml ice cold concentrated sulfuric acid (keep temperature below 5° C). After addition add water to dissolve the precipitate and extract with ether two times. Dry, evaporate in vacuum the ether and distill (70/0.7 or 102/5) to get about 98 g 2-octenoic acid (I). 95 g (1) in 300 ml ether cool to -5° C and slowly add a solution of an excess of diazomethane in ether dried over KOH and let react for about one hour. Let stand twelve hours, evaporate in vacuum and distill (91/17) to get about 94 g clear methyl-2-octenoate (II). 

Octenoic acid, physical properties, 5 31t Octocrylene, cosmetic uv absorber, 7 846t Octogen, 10 735-736... 

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-... 

Biological. Biooxidation of 1-octene may occur yielding 7-octen-l-ol, which may oxidize to 7-octenoic acid (Dugan, 1972). 

In the Madera cockroach, Leucophaea maderae, male calling behavior involves the release of a sex pheromone from the abdominal sternal glands. The extracts of sternal glands attracted conspecific females over a distance and the compounds responsible were identified as hydroxy-3-butan-2-one, (27 , 37 )-butanediol, senecioic acid and ( )-2-octenoic acid. The same components are also present in the male tergal glands. 

T)-2-octenyl acetate was identified from the volatiles produced by the adult female predatory bug, Geocorispunctipes that attracted male bugs. This compound comprised a significant portion of female volatiles. Other components in the extracts from adults of both sexes included (T )-2-hexenyl acetate, ( )-2-octenal and several saturated hydrocarbons but were not part of the attractant. Homogenized adults also yielded (T )-2-hexenal and (T)-4-oxo-2-hexenal whereas cast skins from late instar nymphs contained (T)-2-octenal, (T)-4-oxo-2-octenal, (T)-2-octenoic acid, and other saturated hydrocarbons. ... 

R.L. Johnson, Inhibition of renin by substrate analogue inhibitors containing the olefinic amino acid 5(S)-amino-7-methyl-3( )-octenoic acid, J. Med. Chem. 27 (1984) 1351-1354. 

EOs and their monoterpenes alfected bone metabolism when added to the food of rats. It was demonstrated that these lipophilic compounds inhibited bone resorption [388], It was reported that (2 ,6iI)-8-hydroxy-2,6-dimethyl-2-octenoic acid, a novel monoterpene, from Cistanche salsa had antiosteoporotic properties [389]. 

Octenoic Acid 2-Chloi 0-3.7 dimethyl-3-ethenyl-2-fluoro-ElOhj, 199f. (F - OH)... 

Synthesis of (25, 3R,4/ ,6 )-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid (MeBmt) 19... 

Table 1.2. CHEMICAL STRUCTURES OF CYCLOSPORINS A-Z Bmt = (2S, 3R, 4R, 6 -2-amino-3-hydroxy-4-methyl-6-octenoic acid (= (4R)-4-(( )-2-butenyl)-4-methyI-L-threonine) Abu = L-a-aminobuty-ric acid Nva = L-norvaline MeVal = V-methyl-L-valine MeLeu = A -methyl-L-leucine. 

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