73945-70-7Relevant articles and documents
Method for synthesizing grassland spodoptera litura sex pheromone active ingredients
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Paragraph 0029-0031, (2020/07/02)
The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.
N-acylated alanine methyl esters (NAMEs) from Roseovarius tolerans, structural analogs of quorum-sensing autoinducers, N-acylhomoserine lactones
Bruns, Hilke,Thiel, Verena,Voget, Sonja,Patzelt, Diana,Daniel, Rolf,Wagner-Doebler, Irene,Schulz, Stefan
, p. 1559 - 1573 (2013/10/21)
The Roseobacter clade is one of the most important bacteria group living in the ocean. Liquid cultures of Roseovarius tolerans EL 164 were investigated for the production of autoinducers such as N-acylhomoserine lactones (AHLs) and other secondary metabolites. The XAD extracts were analyzed by GC/MS. Two AHLs, Z7-C14: 1-homoserine lactone (HSL) and C15: 1-HSL, were identified. Additionally, the extract contained five compounds with molecular-ion peaks at m/z 104, 145, and 158, thus exhibiting mass spectra similar to those of AHLs with corresponding peaks at m/z 102, 143, and 156. Isolation of the main compound by column chromatography, NMR analysis, dimethyl disulfide derivatization for the determination of the location of the CiC bond and finally synthesis of the compound with the proposed structure confirmed the compound to be (Z)-N-(hexadec-9-enoyl)alanine methyl ester. Four additional minor compounds were identified as C14: 0-, C15: 0-, C16: 0-, and C17: 1-N-acylated alanine methyl esters (NAMEs). All NAMEs have not been described from natural sources before. A BLASTp search showed the presence of AHL-producing luxI genes, but no homologous genes potentially responsible for the structurally closely related NAMEs were found. The involvement of the NAMEs in chemical communication processes of the bacteria is discussed. Copyright
Cuticular hydrocarbons and novel alkenediol diacetates from wheat stem sawfly (Cephus cinctus): Natural oxidation to pheromone components
Bartelt, Robert J.,Cosse, Allard A.,Petroski, Richard J.,Weaver, David K.
, p. 385 - 405 (2007/10/03)
The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, ω-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected in volatiles collected from living sawflies. Atmospheric oxidation of the diacetates was also demonstrated in the absence of sawflies. One product from the diacetates, 9-acetyloxynonanal, was shown in other research to be particularly active electrophysiologically and was also attractive in the field. Aldehydes from the alkenes also showed strong electrophysiological activity. The concept of volatile pheromones originating from heavy, unsaturated cuticular lipids is discussed.
