Trigonelline 1-Methylnicotinic

Trigonelline (1-methylnicotinic acid zwitterion) [535-83-1] M 137,1, m 218°(dec). Crystd (as monohydrate) from aqueous EtOH, then dried at 100°. 

In general, niacin is widespread in foodstuffs (93,94). Cereals, seeds, meat, and fish are good food sources of niacin. The niacin content of coffee beans is primarily a product of the roasting process, which converts trigonelline (1-methylnicotinic acid) to nicotinic acid (95). 

Trigonelline (N-methylnicotinic acid) is present in green coffee up to 0.6% and is 50% decomposed during roasting. The degradation products include nicotinic acid, pyridine, 3-methyl pyridine, nicotinic acid methyl ester, and a number of other compounds. 

Py (III) NAD nicotinamide — nicotinamide A(-oxide (IV) NAD —> nicotinamide nicotinic acid — nicotinuric acid (V) NAD —> nicotinamide nicotinic acid V -methylnicotinic acid (trigonelline). In rats, pathway II mainly functions, and in humans pathway I. Pathway V functions in mushrooms, shellfish, and plants, but not in mammals. 

C Bemofsky. New synthesis of the 4- and 6-pyridones of 1-methylnicotinamide and 1-methylnicotinic acid (trigonelline). Anal Biochem 96 189-200, 1979. 

Trigonelline, or N-methylnicotinic acid, is a secondary metabolite derived from pyridine nucleotides. Trigonelline was first isolated from fenugreek (Trigonellafoenum-graecum)... 

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