Synthesis of -12-hydroxyendrin and 12-ketoendrin, the two major mammalian metabolites of endrin

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

doi:10.1016/0045-6535(73)90018-0

Cited by 11 publications

(3 citation statements)

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“…This would be consistent with the loss of OH from an endrin alcohol parent ion. Description of the syn-12-hydroxy endrin as very labile to the ionization process suggested a similar structure for U-3 (Bedford and Harrod, 1973). However, identity of U-3 as syn-12- hydroxyendrin could not be confirmed by Cr03/pyridine oxidation to 12-ketoendrin, the oxidation product of U-2.…”

Section: Discussionmentioning

confidence: 94%

“…Rather, U-3 was converted to a mixture of products, some highly polar, one or more of which may have been acidic in nature. Oxidation of both syn-and -12-hydroxyendrin to the same ketone (Bedford and Harrod, 1973) suggests U-3 is not syn-12-hydroxyendrin. Since CI-MS data provided evidence that all of the chlorines were intact on an uncaged mplecule, it would seem reasonable that U-3 may be a cyclic hemiketal (9) (Figure 7), which would produce water-soluble and acidic materials upon Cr03 oxidation.…”

Section: Discussionmentioning

confidence: 99%

“…One minor urinary metabolite was excreted by both strains in equal amount, while a third urinary metabolite (U-3) was unique to the susceptible strain. Identities of metabolic products of endrin recovered from rat have recently been established (Baldwin et al, 1970;Bedford and Harrod, 1973;Bedford et al, 1975). Endrin metabolites isolated from resistant and susceptible strains of pine mice were structurally analyzed so that the relationship of structure to observed toxicity/excretion differentials for the two strains might be compared.…”

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confidence: 99%

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Identification of metabolites of endrin. Metabolism in endrin susceptible and resistant strains of pine mice

Petrella¹,

McKinney²,

Fox³

et al. 1977

J. Agric. Food Chem.

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Section: Discussionmentioning

confidence: 94%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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Identification of metabolites of endrin. Metabolism in endrin susceptible and resistant strains of pine mice

Petrella¹,

McKinney²,

Fox³

et al. 1977

J. Agric. Food Chem.

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The metabolism and residues of [¹⁴C]Endrin in lactating cows and laying hens

et al. 1976

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14C]Endrin was fed to two lactating cows in a portion of their diet for 21 days. The intake was equivalent to approximately 0.1 mg of endrin per kg of total diet. Excretion of radioactivity in milk, urine and faeces reached equilibrium with intake between 4 and 9 days after starting treatment. Milk residues reached 0.003-0.006 mg/kg, were composed of unchanged endrin and were located in the fat. Muscle residues reached 0.001-0.002 mg/kg. Residues in the fat reached a maximum of 0.1 mg/kg and were due to unchanged endrin. [ 14C]Endrin was administered in corn oil to six laying hens for 21 weeks. The intake was equivalent to approximately 0.13 mg/kg of total diet. Ingestion and excretion were almost in balance at 16-20 weeks. Egg residues reached 0.11-0.18 mg/kg, were composed of unchanged endrin and were located in the yolk. Tissue residues were 0.01 mg/kg in breast, 0.1 mg/kg in leg, 0.17 mg/kg in kidney, 0.47 mg/kg in liver and 1.0 mg/kg in fat. The residues were accounted for as unchanged endrin except in liver and kidney in which part was probably due to polar metabolites in the process of excretion. The results show that endrin is much more rapidly metabolised in cows than in hens. The pathways of metabolism were fundamentally the same in both species, the major product being anti-l2-hydroxyendrin, which was found unconjugated in cow urine and faeces and as the 0-sulphate conjugate in hen excreta. The only observed difference in primary metabolism was some syn-12-hydroxyendrin and 12-ketoendrin in cows. This pathway was not detected in hens.

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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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Synthesis of -12-hydroxyendrin and 12-ketoendrin, the two major mammalian metabolites of endrin

Cited by 11 publications

References 6 publications

Identification of metabolites of endrin. Metabolism in endrin susceptible and resistant strains of pine mice

Identification of metabolites of endrin. Metabolism in endrin susceptible and resistant strains of pine mice

The metabolism and residues of [¹⁴C]Endrin in lactating cows and laying hens

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

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Synthesis of -12-hydroxyendrin and 12-ketoendrin, the two major mammalian metabolites of endrin

Cited by 11 publications

References 6 publications

Identification of metabolites of endrin. Metabolism in endrin susceptible and resistant strains of pine mice

Identification of metabolites of endrin. Metabolism in endrin susceptible and resistant strains of pine mice

The metabolism and residues of [14C]Endrin in lactating cows and laying hens

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

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The metabolism and residues of [¹⁴C]Endrin in lactating cows and laying hens