Methyl -2,4-decadienoate

Baeckstrom, P., Jacobsson, U., Norin, T., and UneUus, C.R., Synthesis and characterization of all four isomers of methyl 2,4-decadienoate for an investigation of the pheromone components of Pityogenes chalcographus. Tetrahedron, 44, 2541, 1988. 

Pellitorine (1) has also been prepared by the coupling of a vinyl iodide with methyl acrylate using palladium and phase transfer catalyzed conditions. Under these conditions methyl (2 ,4 )-decadienoate was obtained stereoselectively and then transformed into the corresponding isobutylamide [50] (Scheme 7). 

The components of the sex pheromone from female nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera Limacodidae) were identified. The compounds from D. trima were 2-methylbutyl-(A )-7,9-decadienoate (A) and ( )-2-hexenyl ( )-7,9-decadienoate (B) and from D. bradleyi were identified as methyl (T)-7,9-decadienoate (C) and isobutyl (.ff)-7,9-decadienoate (D). In Malaysia, (5 )-2-methylbutyl- E)-7,9-decadienoate in combination with B proved to be essential and synergistic pheromone components for attraction of males in field tests. (i )-2-methylbutyl- ( )-7,9-decadienoate had no behavioral activity. Compound D singly attracted male D. bradleyi, but the addition of C and D in a ratio of 1 10 significantly enhanced attractiveness of the bait. ... 

Butyl acetate Pentyl acetate Hexyl acetate 2-Methylbutyl acetate Hexyl propane ate Ethyl butanoate Butyl butanoate Hexyl butanoate Methyl 2-methylbutanoate Ethyl 2-methylbutanoate Propyl 2-methylbutanoate Butyl 2-methylbutanoate Hexyl 2-methylbutanoate Ethyl hexanoate Ethyl octanoate Ethyl ( )-2-octenoate Methyl ( ,Z)-2,4-decadienoate Ethyl ( ,Z)-2,4-decadienoate... 

The flavour of distillates from apple and pear is characterised by typical aroma compounds from these fruits formed by enzymatic degradation of fatty acids to C6-fragments like hexanol, trans-2-hexenol, as well as ethyl esters and acetates of hexanoic acid. In distillates of pears, especially of the variety Bartlett pear, the characteristic pear flavour is mainly dominated by the ethyl and methyl esters of frans-2-czs-4-decadienoic acid and trans-2-trans-A-decadienoic acid [27-29], The biogenesis of these monounsaturated, diunsaturated, and triunsaturated esters may be explained by -oxidation of unsaturated linoleic and linolenic acid in the fruits. The sesquiterpene compound a-farnesene, which is formed during postharvest ripening and storage of Bartlett pears [28], shows that quality and intensity of distilled pear spirits is mainly influenced by the quality and degree of ripeness of the fruits. 

Figure 7.26 The structure of the hepatotoxic cyclic heptapeptide microcystin LR. L-Arginine and L-leucine are variable amino acids. The reactive unsaturated group is indicated by the star. Abbreviations Adda, amino-methoxy-trimethyl-phenyl-decadienoic acid Mdha, methyldehydro-alanine Masp, methyl D-/so-aspartate D-Glu, D-/soglutamate D-Ala, D-alanine.

Jennings et al (228) fractionated an extract from Bartlett pears into 32 volatile components of which five were found to contribute significantly to the characteristic pear aroma. Later studies indicated that esters of trans-2 cis-4 decadienoic acid and hexyl acetate were significant components of the Bartlett pear aroma (229, 230). More recently, numerous volatiles of Bartlett pears were separated and identified including esters of methyl, ethyl, propyl, butyl, and hexyl alcohols, and Cio to Ci8 fatty acids (231, 232). 

Birgersson G., Byers J.A., Bergstrom G. and Lofqvist J. (1990) Production of pheromone components, chalcogran and methyl ( ,Z)-2,4-decadienoate, in the spruce engraver Pityogenes chalcographus. J. Insect Physiol. 36, 391-395. 

Cl1HI603 allyl-3,4-epoxy-6-methylcyclohexanecarboxyla 10138-39-3 378.15 32.311 2 22601 Cl 1 HI802 methyl trans-2,trans-4-decadienoate 7328-33-8 502.15 44.091 2... 

GC-MS has been responsible for the identification of a variety of unusual lipids associated with diseased conditions. Hydroxyocta-decadienoic esters of cholesterol for example, have been isolated from aortal atheroma placques [277] and branched chain and odd numbered fatty acids identified in the glycerolipids of brain, spinal cord and sciatic nerve [278] from a patient with methylmalonic aciduria. The latter compounds are thought to arise by the replacement of malonyl CoA with methyl malonyl CoA, and acetyl CoA with propionyl CoA at certain stages of fatty acid synthesis. In these and other examples, the lipids need to be hydrolysed to permit the identification of the constituent fatty acids. As the class of lipids is usually known from the separation procedure used, the nature of the fatty acids may allow the characterisation of the complete molecule. However, volatilisation of the intact lipid into the mass spectrometer when possible would be preferable, particularly when it is present in a mixture and separation of the components is first made by GC. 

CIC The floral fruity perfume is the result of a balanced mixture of famesene, linalool, ethyl-2-methyl-2-butenoate, ethyl (E)-2-(Z)-4-decadienoate, derivatives around beta-ionone (theaspirone, theaspirane (E,E)-6,8-megastigmadien-4-one) and... 

Unsaturated esters may also be derived from the products of B-oxidation of unsaturated fatty acids. Methyl-and ethyl decadienoates are known as character impact compounds of Bartlett pears and all presumptive intermediates of the pathway were identified by Jennings et al. (JLZ UL) binoleyl-CoA is transformed into (E,Z)-2,4-decadienoyl-CoA by B-oxidation. The further degradation... 

There are numerous examples of internal direction from indigenous stereogenic centers in ene reactions, especially intramolecular variants that form rings. For example, levels of 94% de for the zinc bromide induced and 76% de for the thermally induced (180 °C) intramolecular ene reaction with methyl 2-methoxycarbonyl-5,9-dimethyl-2,8-decadienoate have been found28, 0. 

Decadienoic acid, 3-hydroxy-3-methyI-6-(1-methylethyl)-9-(tetrahydro-5-oxo-2-furanyl)-, methyl ester... 

Aasen, A.J., C.R. Enzell, andT. Chuman (65)-3-Methyl-6-isopropyl-9-oxo-2E,4E-decadienoic acid from Turkish Nicotiana tabacum L. Assignment of absolute configuration Agr. Biol. Chem. 39 (1975) 2085-2089. 

Figure 39.1a shows the generic structure of microcystins (MC), with the two most variable positions marked by X and Z. The numbering of the individual positions was done before the elucidation of the biosynthetical pathway and is arbitrary (see below). MCs are cyclic heptapeptides with several structural peculiarities. The moiety characteristic of microcystins and nodularins is the Adda, abbreviated for 3-amino-9-methoxy-2,6,8,-trimethyl-10-phenyl-4,6-decadienoic acid, a P-amino acid that is not known from other natural products. Further peculiarities of the molecule are o-amino acids. These stereoisomers of commonly occurring L-amino acids are not found in ribosomally synthesized proteins and peptides and are therefore called nonproteinogenic amino acids. A-methyl-dehydroalanine (Mdha) in position 7 also is a nonproteinogenic amino acid as it is the case with o-erythro-P-methyl-iso-aspartate (o-MeAsp). 

C,H, 02, Mr 156.22, bp. 73 °C (4.0 kPa) (25,5R)-iso-mer [a] -100° (hexane) (2S,5S)-isomer [a] r%° (hexane). Aggregation pheromone of bark beetles of the genus Pityogenes. Males of P. chalcographm excrete this spiroacetal as a mixture of the (25,55)- and (25,5/()-isomers to attract males and females of the same species to colonize a host tree. Only the (25,5/ )-isomer has an attracting action which is dramatically increased by simultaneously excreted, extremely small amounts of methyl (2E,4Z)-2,4-decadienoate (C, H,g02, Mr 182.26). Isomers of C. are the pheromones conophthorin and olean, the sexual attractant of the olive fruit fly Dacus oleae. C. is currently the economically most important pheromone with a market value in 1995 of ca. 20 Mio. DM for its use against forest pests. 

Methyl 17-hydroxy-18-methyl-2,5,8,11,14-pentakis( 1 -methylethyl)-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaoxanonadecanoate, see M-20069 Methyl 8-hydroxy-10-[3-(2-octenyl)oxirany 1]-5,9-decadienoate, in H-10130 Methyl 2-hydroxy-/ -tolyl ketone, see H-30176 Methylillukumbin A, in 1-30007 Methylillukumbin B, in 1-30007... 

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