Trigonelline (chloride)

• CAT Number: R061492
• CAS Number: 6138-41-6
• Molecular Formula: C7H8NO2 • Cl
• Molecular Weight: 173.6
• Purity: ≥95%
• Synonyms: N-methyl Nicotinic Acid betaine
• Target: Anti-infection
• Storage: -20°C
• InChI: InChI=1S/C7H7NO2.ClH/c1-8-4-2-3-6(5-8)7(9)10;/h2-5H,1H3;1H
• InChIKey: TZSYLWAXZMNUJB-UHFFFAOYSA-N
• SMILES: OC(C1=C[N+](C)=CC=C1)=O.[Cl-]

Trigonelline is a pyridine alkaloid found in various edible seeds and legumes, including coffee. It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3; nicotinic acid) and, as a product of niacin metabolism, is excreted in urine of mammals. Trigonelline has been used to reduce blood glucose levels and to inhibit PPARγ expression in rat models of diabetes. It is also reported to inhibit the migration of hepatocarcinoma cells and render them more susceptible to apoptosis by reducing Raf/ERK/Nrf2 protein levels and activities of anti-oxidative enzymes further downstream, such as SOD, catalase, and glutathione peroxidase.

Reference

1.Nuhu, A.A. Bioactive micronutrients in coffee: Recent analytical approaches for characterization and quantification. ISRN Nutr. 2014:384230, (2014).