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Trigonelline

Trigonelline

IUPAC name	1-Methylpyridinium-3-carboxylate
Other names	Nicotinic acid N-methylbetaine Coffearine Caffearine Gynesine Trigenolline
Identifiers
CAS number	535-83-1
SMILES	C[N]1=CC(C([O])=O)=CC=C1
Properties
Molecular formula	C₇H₇NO₂
Molar mass	137.13 g/mol
Density	? g/cm³
Melting point	230-233 °C (monohydrate) 258-259 °C (hydrochloride)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Trigonelline is an alkaloid with chemical formula C₇H₇NO₂. It is an inner salt formed by the addition of a methyl group to the nitrogen atom of niacin. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine.^[1]

Additional recommended knowledge

Essential Laboratory Skills Guide

Daily Visual Balance Check

Weighing the right way

Trigonelline is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth.^[2]

References

^ Merck Index, 11th Edition, 9606.
^ Daglia, M.; R. Tarsi, A. Papetti, P. Grisoli, C. Dacarro, C. Pruzzo, and G. Gazzani (2002). "Antiadhesive Effect of Green and Roasted Coffee on Streptococcus mutans' Adhesive Properties on Saliva-Coated Hydroxyapatite Beads". Journal of Agricultural and Food Chemistry 50: 1225–1229. doi:10.1021/jf010958t.