An improved preparation of -4,5-dihydroxy-4,5-dihydroaldrin, a metabolite of HEOD (dieldrin) in mammals, insects, and microorganisms

Bedford, Colin T.; Harrod, R. K.

doi:10.1016/0045-6535(72)90029-x

Cited by 8 publications

(2 citation statements)

References 5 publications

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“…Organochlorine insecticides used included dieldrin ((1aα,2aα,6aα,7aα)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2β,7β:3α,6α-dimethanonaphth[2,3-b]oxirene), heptachlor (1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methano-1 H -indene), heptachlor epoxide (1,2,,4,5,6,7,8,8-octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methano-1 H -indene), endosulfan (6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin 3-oxide), endosulfan sulfate (6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin 3,3-dioxide), DDT (1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane), and DDE (1,1-dichloro-2,2-bis(4-chlorophenyl)ethane). (±)-Aldrin trans -diol ((±)-1,2,3,4,10,10-hexachloro-1,4,4aβ,5,6,7,8,8aβ-octahydro-1β,4β:5α,8α-dimethanonaphthalene-6β,7α-diol) was synthesized from aldrin according to Bedford and Harrod’s procedure with slight modification (Figure S1, Supporting Information). Epoxidation of aldrin with m -chloroperbenzoic acid afforded dieldrin.…”

Section: Methodsmentioning

confidence: 99%

Biodegradation of Dieldrin by a Soil Fungus Isolated from a Soil with Annual Endosulfan Applications

Kataoka

Takagi

Kamei

et al. 2010

Environ. Sci. Technol.

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An aerobic dieldrin-degrading fungus, Mucor racemosus strain DDF, was isolated from a soil to which endosulfan had been annually applied for more than 10 years until 2008. Strain DDF degraded dieldrin to 1.01 microM from 14.3 microM during a 10-day incubation at 25 degrees C. Approximately 0.15 microM (9%) of aldrin trans-diol was generated from the dieldrin degradation after a 1-day incubation. The degradation of dieldrin by strain DDF was detected over a broad range of pH and concentrations of glucose and nitrogen sources. Extracellular fluid without mycelia also degraded dieldrin. Strain DDF degraded not only dieldrin but also heptachlor, heptachlor epoxide, endosulfan, endosulfan sulfate, DDT, and DDE. Endosulfan sulfate and heptachlor were degraded by 0.64 microM (95%) and 0.75 microM (94%), respectively, whereas endosulfan and DDE were degraded by 2.42 microM (80%) and 3.29 microM (79%), respectively, and DDT and heptachlor epoxide were degraded by 6.95 microM (49.3%) and 5.36 microM (67.5%), respectively, compared with the control, which had a concentration of approximately 14 microM. These results suggest that strain DDF could be a candidate for the bioremediation of sites contaminated with various persistent organochlorine pesticides including POPs.

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Section: Methodsmentioning

confidence: 99%

Biodegradation of Dieldrin by a Soil Fungus Isolated from a Soil with Annual Endosulfan Applications

Kataoka

Takagi

Kamei

et al. 2010

Environ. Sci. Technol.

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“…In two previous papers on the synthesis of dieldrin metabolites, we have described an improved synthesis of trons-4,5-dihydroaldrin-4,5-diol (Bedford and Harrod, 1972a) and the first total synthesis of syn-12-hydroxydieldrin (Bedford and Harrod, 1972b). In this paper we record a total synthesis of Klein's metabolite and thereby complete the synthesis of all of the known metabolites of dieldrin.…”

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confidence: 99%

Synthesis of dieldrin metabolites. 3. Two-step conversion of syn-12-hydroxydieldrin into Klein's metabolite (3,5,6,6,7-pentachloro-11,12-exo-epoxypentacyclo[6.4.0.02,10.03,7.05,9]dodecan-4-one)

Bedford¹,

Smith²

1978

J. Agric. Food Chem.

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Solvolysis of the triflate (trifluoromethanesulfonate) of syn-12-hydroxydieldrin led in part (40%) to a bridged ketone, which was identical in all respects (melting point; infrared, proton magnetic resonance, and mass spectra) with the hitherto unsynthesized metabolite of dieldrin known as "Klein's metabolite". This has provided the ultimate proof of its structure and has made available sufficient material for a planned study of its toxicity and metabolism. The structure of one of the by-products of the solvolysis reaction has been elucidated.

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Synthesis of endrin metabolites. Part 2: Total synthesis and confirmation of the structure of 3‐hydroxyendrin

et al. 1986

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3‐Hydroxyendrin, a minor metabolite of endrin in several mammals, has been synthesised for the first time in a three‐step procedure. The synthesis is based on the two‐step commercial manufacture of endrin, with cyclopenta‐1,3‐dienyl acetate replacing cyclopentadiene in the Diels‐Alder adduction step to isodrin formation. The adduct formed from cyclopenta‐1,3‐dienyl acetate and 1,2,3,4,7,7‐hexachlorobicyclo‐[2.2.1]hepta‐2,5‐diene, 3‐acetoxyisodrin, was purified by chromatography and sequentially deacetylated (to 3‐hydroxyisodrin) and epoxidised to yield 3‐hydroxyendrin. A comparison of this material with a sample of a metabolite, isolated from endrin‐dosed rates in 1970, showed that they were identical in all spectral properties (m.s., i.r. and n.m.r.). This has provided confirmation of the original structural assignment and has made available sufficient quantities of the metabolite as a reference material for any future metabolism or residue studies.

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An improved preparation of -4,5-dihydroxy-4,5-dihydroaldrin, a metabolite of HEOD (dieldrin) in mammals, insects, and microorganisms

Cited by 8 publications

References 5 publications

Biodegradation of Dieldrin by a Soil Fungus Isolated from a Soil with Annual Endosulfan Applications

Biodegradation of Dieldrin by a Soil Fungus Isolated from a Soil with Annual Endosulfan Applications

Synthesis of dieldrin metabolites. 3. Two-step conversion of syn-12-hydroxydieldrin into Klein's metabolite (3,5,6,6,7-pentachloro-11,12-exo-epoxypentacyclo[6.4.0.02,10.03,7.05,9]dodecan-4-one)

Synthesis of endrin metabolites. Part 2: Total synthesis and confirmation of the structure of 3‐hydroxyendrin

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