C

CACAO BEAN. See Chocolate and cocoa. CAFFEINE

Caffeine (1,3,7-trimethylxanthine) was isolated from coffee in 1820 (1). Thein was isolated from tea in 1827 and later shown to be identical with the coffee isolate. It was subsequently identified in cocoa, maté, kola nuts, and other plants; structure was determined in 1875. Caffeine is one of several methylxanthines that occur naturally, primarily in plant matter that is used to prepare beverages. Other methylxanthines that usually accompany it include theobromine and theophylline. The methylxanthines, as dio-xypurines, are related to two nucleic acids: adenine and guanine. This is relevant to their biosynthesis and physiological effects. Their relationship to uric acids accounts for their metabolic fate. The structures of caffeine and related compounds are shown in Figure 1.

Total synthesis was first achieved in 1895 starting with dimethylurea. Dimethyluric acid, chlorotheophylline, and chlorocaffeine were intermediates (2).

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