Studies on the Blue Pigments Produced from Genipin and Methylamine. II.1On the Formation Mechanisms of Brownish-Red Intermediates Leading to the Blue Pigment Formation2)

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Abstract

The mechanisms of the formation of brownish-red pigments having a 2-methyl-4-carbomethoxy-2-pyrindine nucleus as a basic skeleton by reaction of genipin with methylamine under an atmosphere of inert gas are discussed based on the isolation of 5,6-dihydro-2-methyl-4-carbomethoxy-8-hydroxymethyl-2-pyrindine as a precursor and on comparisons of the results obtained from the reactions of genipin congeners and methylamine. The origin of the extra methyl group at C-6 in the structures of some of the brownish-red pigments was clarified to be the carbon atom of the hydroxymethyl group at C-8 of genipin by using deuterium-labelled genipin. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

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Toityama, R., Ikumoto, T., INour, K., Taked, Y., Yatsuzuka, M., Inouy, H., … Shingi, T. (1994). Studies on the Blue Pigments Produced from Genipin and Methylamine. II.1On the Formation Mechanisms of Brownish-Red Intermediates Leading to the Blue Pigment Formation2). Chemical and Pharmaceutical Bulletin, 42(8), 1571–1578. https://doi.org/10.1248/cpb.42.1571

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