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The Absolute Configuration of Precocene I Dihydrodiols Produced by Metabolism of Precocene I by Corpora Allata of Locusta Migratoria, in Vitro

The Absolute Configuration of Precocene I Dihydrodiols Produced by Metabolism of Precocene I by Corpora Allata of Locusta Migratoria, in Vitro

A F Hamnett, G E Pratt

Life Sci. 1983 Jun 13;32(24):2747-53.

PMID: 6855469

Abstract:

The corpora allata from adult female Locusta migratoria metabolize precocene I (7-methoxy-2,2-dimethyl-2H-benzo [b]pyran to cis- & trans-precocene I dihydrodiols (3,4-dihydro-7-methoxy-2,2-dimethyl-2H-benzo [b]pyran-3,4-diol). Derivatization of the dihydrodiols with (-)menthoxy acetyl chloride allowed complete resolution of all four optical isomers. When [4-3H]-precocene I was incubated in vitro with Locusta migratoria corpora allata, it was metabolized stereospecifically to (-)trans-(3R,4S) and (+)cis-(3R,4R) dihydrodiols. Approximately half the precosyl residues bound to cellular macromolecules were discharged by heating to 95 degrees C at neutral pH, as dihydrodiols of the same stereochemistry.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP17598026	Precocene I		17598-02-6	Price

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