Identification and synthesis of the male produced volatiles of the carrion beetle, Oxelytrum erythrurum (Coleoptera: Silphidae)

Fockink, Douglas H.; Martins, Camila B. C.; Zarbin, Paulo H. G.

doi:10.1016/j.tetlet.2015.08.004

Cited by 4 publications

(5 citation statements)

References 20 publications

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“…Then the 2‐(9‐bromonon‐1‐yloxy)tetrahydro‐2 H ‐pyrane ( 6 ) reacted with the carbanion to realize the necessary chain extension to 16 carbon atoms yielding compounds 7a,b . Compounds 6 was prepared from nonane‐1,9‐diol ( 5 ) by monobromination reaction according to Fockink et al The blocking of the free hydroxyl group that is necessary for the following step was done with 3,4‐dihydro‐2 H ‐pyrane under the common conditions . One of the 2 carboxylic ester groups is the latent methyl group with or without deuteration.…”

Section: Resultsmentioning

confidence: 99%

“…The preparation was following the procedure described in the literature starting from nonan‐1,9‐diol ( 5 ) to give 6 as colorless liquid: R f 0.47 (CHCl 3 /heptane 6:4); 1 H NMR (400 MHz, CDCl 3 ) δ 1.30‐1.43 ( m , 10H, Br(CH 2 ) 2 (C H 2 ) 5 ‐), 1.50‐1.61 ( m , 6H, ‐C H 2 CH 2 OCH‐CH 2 (C H 2 ) 2 ‐), 1.68‐1.74 ( m , 1H, ‐OCH‐C H H′‐), 1.78‐1.88 ( m , 3H, BrCH 2 C H 2 ‐, ‐OCH‐CH H ′‐), 3.35‐3.41 ( m , 3H, BrC H 2 (CH 2 ) 7 C H H′‐), 3.47‐3.52 ( m , 1H, ‐OCH‐(CH 2 ) 3 C H H′‐), 3.72 (d t , J = 6.9, 9.5 Hz, 1H, Br(CH 2 ) 8 CH H ′‐), 3.84‐3.89 ( m , 1H, ‐OCH‐(CH 2 ) 3 CH H ′‐), 4.56‐4.57 ( m , 1H, ‐OC H ‐O‐); 13 C NMR (100 MHz, CDCl 3 ) δ = 19.9, 25.7, 26.3, 28.3, 29.5, 29.9, 30.9, 33.0, 34.1, 62.5, 67.8, 99.0.…”

Section: Methodsmentioning

confidence: 99%

“…The combined organic layers were dried over Na 2 SO 4 and filtered and evaporated to dryness under reduced pressure. The residue was purified by column chromatography using gradient technique with heptane/Et 2 O eluent to give diethyl 6,6,6- Synthesis of 2-(9-bromononyloxy)tetrahydro-2H-pyran (6) The preparation was following the procedure described in the literature 27…”

Section: Monoalkylation Of Diethyl Malonatementioning

confidence: 99%

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Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering

Sonnenberger

Eichner

Schmitt

et al. 2017

J. Label Compd. Radiopharm

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The synthesis of specific deuterated derivatives of the long chained ceramides [EOS] and [EOP] is described. The structural differences with respect to the natural compounds are founded in the substitution of the 2 double bonds containing linoleic acid by a palmitic acid branched with a methyl group in 10-position. The specific deuteration is introduced both in the branched and in the terminal methyl group, which was realized by common methods of successive deuteration of carboxylic groups in 3 steps. These modified fatty acids resp. the corresponding ceramides [EOS] and [EOP] were prepared for neutron scattering investigations. First results of these investigations were presented in this manuscript showing that the deuterated compounds could be detected in the stratum corneum lipid model membranes. The deuterated ceramides [EOS] and [EOP] are valuable tools to investigate the influence of these long chained ceramide species on the nanostructure of stratum corneum lipid model membranes.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Monoalkylation Of Diethyl Malonatementioning

confidence: 99%

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Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering

Sonnenberger

Eichner

Schmitt

et al. 2017

J. Label Compd. Radiopharm

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“…Furthermore, the composition of fauna in corpses is fundamental to the release of attractive odors. In particular, species of flies and beetles release pheromones that attract individuals to reproduce and feed on these carcasses (von Hoermann et al, 2012;Fockink et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

Effect of thiamethoxam (organophosphate) on the flies and beetle visitation and cadaveric decomposition process

Eulalio

Paula

Michelutti

et al. 2023

Rev. Bras. entomol.

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Entomofauna associated with decaying cadavers may be useful in criminal investigation, either through the development of immature insects of interest or through entomological succession in corpses. These factors may vary if the insects are exposed to toxic substances that can modify the insect's developmental cycle, as well as its own occurrence, which would imply significant changes in the results of any investigation. However, there are few studies on how contamination by toxic compounds can affect the action of insects on carcasses and their consequence for forensic expertise. Therefore, this study aimed to test the hypothesis that the normal visitation of flies and beetles is altered in insecticide-contaminated carcasses. The experiment was carried out in a sugarcane plantation, using pig carcasses contaminated with insecticide and the same number of carcasses without any type of contamination as a control. In all experiments, the contaminated carcasses reached the final phase of decomposition in a longer time than the uncontaminated carcasses of the control group. A total of 2.767 specimens were collected and identified, 2.103 individuals from the order Diptera and 664 from the order Coleoptera. There was a significant geometric regression adjustment during the decomposition phases only for the control group, different from the contaminated carcasses in which this pattern did not occur. Results show that contamination by insecticide alters decomposition time and phase, altering the action of flies and beetles, affecting the abundance, composition of species as well as their activities, which can alter the data used by experts in criminal experts.

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“…The unbranched hydrocarbon pheromones synthesized are shown in Fig. 2, comprising the pheromones of Chauliognathus fallax (Col., Cantharidae): 1 ; 22 Chrysopa formosa (Neu., Chrysopidae): 2 ; 23 Susuacanga octoguttata (Col., Cerambycidae): 3 ; 24 Oxelytrum discicolle (Col., Silphidae): 4 ; 25 Oxelytrum erythrurum (Col., Silphidae): 5 ; 26 Semiotthisa spp. (Lep., Geometridae): 6 ; lymantrids (Lep., Lymantriidae): 7 and 8 ; Anticarsia gemmatalis (Lep., Noctuidae): 9 ; Utetheisa ornatrix (Lep., Erebidae): 10 ; Jodis lactearia (Lep., Geometridae): 11 and Maxates versicauda microptera (Lep., Geometridae): 12 ; 27 Naxa seriaria (Lep., Geometridae): 13 ; 28 Drosophila melanogaster (Dip., Drosophilidae): 14 and 15 .…”

Section: Fatty Acid/polyketide-derived Pheromonesmentioning

confidence: 99%

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

et al. 2023

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Identification and synthesis of the male produced volatiles of the carrion beetle, Oxelytrum erythrurum (Coleoptera: Silphidae)

Cited by 4 publications

References 20 publications

Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering

Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering

Effect of thiamethoxam (organophosphate) on the flies and beetle visitation and cadaveric decomposition process

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

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