Coumingidin, ein neues krystallisiertes Alkaloid aus Erythrophleum Couminga

Helvetica Chimica Acta
1941.0

Abstract

A new crystalline alkaloid, Coumingidin, was isolated from Erythrophleum Couminga. Initially presumed to be identical to Coumingin discovered by Dalma, it was later identified as a distinct compound through comparison with the manuscript provided by Ruzicka and coworkers. The isolation involved extracting 10 kg of bark with ethylene chloride, resulting in approximately 15 g of crude base. Coumingidin has a molecular formula of C₂₈H₄₅O₆N (or alternatively C₂₇H₄₃O₆N) and melts at 160–161 °C. Key derivatives include a neutral acetyl product (melting point 155 °C), a nitroso compound (174–174.5 °C), a hydrochloride salt (217–219 °C), and a dihydro derivative (dihydro-Coumingidin perchlorate, 166–168 °C). Structural investigations demonstrated that Coumingidin is an ester of a complex acid with an amino alcohol, which was identified as monomethylaminoethanol using its 3,5-dinitrobenzoyl chloride derivative. Hydrolysis with oxalic acid yielded an acid with the formula C₂₅H₃₆O₅, which absorbed 3 moles of hydrogen during hydrogenation. Coumingidin exhibits similarities to other known Erythrophleum alkaloids, including the formation of a sparingly soluble perchlorate and the presence of a double bond.

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