Approaches to the synthesis of the insect juvenile hormone analog ethyl 3,7,11-trimethyl-2,4-dodecadienoate and its photochemistry

Ca, Hendrick; We, Willy; Dr, McKean; Baggiolini, Enrico G.; Jb, Siddall

doi:10.1021/jo00889a002

Cited by 62 publications

(18 citation statements)

References 9 publications

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“…The common starting compound for the first three, 6,10-dimethyl-3(£),9(F)undecadien-2-one (2a), was prepared from (±)-citronellal (la) and the source of the 9,10-unsubstituted derivatives, 6.10-dimethyl-3(F)-undecen-2-one (2b), from 3,7-dimethyloctanal (lb) by aldol condensation with acetone in an aqueous medium in the presence of barium hydroxide (Scheme I) (Streinz and Romanuk, 1981). This method / > -.0 3b = /î s much simpler than that reported previously, in which aldehydes and 2-oxopropyl phosphonate react (Henrick et al, 1975). These compounds and their derivatives are all racemic.…”

Section: Resultsmentioning

confidence: 90%

Development of insect juvenile hormone active oxime O-ethers and carbamates

Nakayama¹,

Iwamura²,

Niwa³

et al. 1985

J. Agric. Food Chem.

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Section: Resultsmentioning

confidence: 90%

Development of insect juvenile hormone active oxime O-ethers and carbamates

Nakayama¹,

Iwamura²,

Niwa³

et al. 1985

J. Agric. Food Chem.

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“…The 13 C NMR and DEPT spectroscopic data (Table 2) showed 22 carbon signals, including six methyls, eight sp 3 methylenes, three sp 3 methines, one sp 2 methine, three sp 2 quaternary and one sp 3 quaternary carbons. The signals in the 1 H NMR spectrum at δ H (5.81, 1H, s), 2.22 (1H, d, J = 4.4 Hz), 2.27 (1H, m), 4.46 (1H, m), and 1.99 (3H, s) verified the presence of a subunit of 3-methyl-2-penten-5-olide [20,21]. The planar structure and all of the 1 H and 13 C chemical shifts of 6 were elucidated by 2D NMR experiments, in particular the 1 H– 1 H COSY and HMBC experiments (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic and Anti-Inflammatory Metabolites from the Soft Coral Scleronephthya gracillimum

et al. 2013

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Five new pregnane-type steroids, sclerosteroids J–N (1–5), and a diterpenoid with a new chemotype 3-methyl-5-(10′-acetoxy-2′,6′,10′-trimethylundecyl)-2-penten-5-olide (6), have been isolated from a soft coral Scleronephthya gracillimum. The structures of the metabolites were determined by extensive spectroscopic analysis. Compound 4 exhibited cytotoxicity against HepG2, A549, and MDA-MB-231 cancer cell lines. Furthermore, steroids 2 and 4 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein, and 1, 2, 4 and 5 could effectively reduce the accumulation of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells.

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“…S-Methoprene absorbs light in the ultraviolet region ranging from 190 to 310 nm with an absorption maximum at 259 nm in n-heptane. Irradiation of S-methoprene (t-ME) in nheptane, ethanol, or water with a 450 W Hanovia High-Pressure Mercury lamp led to a photostationary state containing a 52:49 mixture of t-ME and its 2-cis-4-transisomer (ct-ME), respectively (36). In addition to these products, trace amounts (∼1-2%) of the 2-trans-4-cis-isomer (tc-ME) and all-cis-isomer (c-ME) were also detected.…”

Section: Resultsmentioning

confidence: 99%

Photoproducts and Metabolites of a Common Insect Growth Regulator Produce Developmental Deformities in Xenopus

Clair

Bantle

Dumont

1998

Environ. Sci. Technol.

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In the past decade, numerous sights across North America have been found which contain abnormal levels of deformed amphibians. This deformation was not limited to species, geography, or climate and spanned a wide range of phenotypes. This report begins to explain these findings by examining the effects of pesticide degradation in early amphibian development through directly exposing Xenopus laevis embryos to trace levels of synthetically prepared degradates. This method specifically determines the risk posed by each individual chemical resulting from the natural fate of the host pesticide. Through this approach, we find that while the common insect growth regulator, S-methoprene, poses minimal developmental determent, products of its reaction with sunlight, water, and microorganisms dramatically interfere with normal amphibian development. The addition of 1 μL/L of several of S-methoprene's degradates to the environment of developing embryos resulted in juveniles with deformation similar to that found naturally. Current developmental assessments examine only the risk posed by host pesticides. This study now suggest that the simple examination of the these materials is not sufficient, but now forward the need for critically examining the temporal relation between both development and chemical degradation.

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Approaches to the synthesis of the insect juvenile hormone analog ethyl 3,7,11-trimethyl-2,4-dodecadienoate and its photochemistry

Cited by 62 publications

References 9 publications

Development of insect juvenile hormone active oxime O-ethers and carbamates

Development of insect juvenile hormone active oxime O-ethers and carbamates

Cytotoxic and Anti-Inflammatory Metabolites from the Soft Coral Scleronephthya gracillimum

Photoproducts and Metabolites of a Common Insect Growth Regulator Produce Developmental Deformities in Xenopus

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