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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]

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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.