Djenkolic Acid - Discovery and Synthesis

Discovery and Synthesis

Djenkolic acid was first isolated by Van Veen and Hyman from the urine of the natives of Java who had eaten the djenkol bean and were suffering from poisoning. They then succeeded in isolating the djenkolic acid crystals from the djenkol beans treated with Ba(OH)2 at 30°C for a prolonged period of time.

Djenkolic acid was later reported to be found as much as 20 grams in every kilogram of dry djenkol beans, and it has also been reported to be found to a lesser extent in the seeds of other leguminous plants such as Leucaena esculenta (2.2 g/kg) and Pithecolobium ondulatum (2.8 g/kg).

Du Vigneaud and Patterson managed to synthesize djenkolic acid by the condensation of methylene chloride with 2 moles of L-cysteine in liquid ammonia and to show that their synthetic compound was identical with the naturally occurring djenkolic acid. Later on, Armstrong and du Vigneaud prepared djenkolic acid by the direct combination of 1 mole of formaldehyde with 2 moles of L-cysteine in a strongly acid solution.

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