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Download Product Insert (PDF) PRODUCT INFORMATION Trigonelline (chloride) Item No. 11904 CAS Registry No.: 6138-41-6 Formal Name: 3-carboxy-1-methyl-pyridinium, monochloride Synonym: N-methyl Nicotinic Acid betaine HOOC + MF: C7H8NO2 • Cl N FW: 173.6 Purity: ≥95% UV/Vis.: λmax: 265 nm • Cl- Supplied as: A crystalline solid Storage: -20°C Stability: ≥2 years Information represents the product specifications. Batch specific analytical results are provided on each certificate of analysis. Laboratory Procedures Trigonelline (chloride) is supplied as a crystalline solid. Trigonelline (chloride) is sparingly soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide. For biological experiments, we suggest that organic solvent-free aqueous solutions of trigonelline (chloride) be prepared by directly dissolving the crystalline solid in aqueous buffers. The solubility of trigonelline (chloride) in PBS, pH 7.2, is approximately 5 mg/ml. We do not recommend storing the aqueous solution for more than one day. Description 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.1 Trigonelline has been used to reduce blood glucose levels and to inhibit PPARγ expression in rat models of diabetes.2,3 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.4,5 References 1. Nuhu, A.A. Bioactive micronutrients in coffee: Recent analytical approaches for characterization and quantification. ISRN Nutr. 2014:384230, (2014). 2. Yoshinari, O., Sato, H., and Igarashi, K. Anti-diabetic effects of pumpkin and its components, trigonelline and nicotinic acid, on Goto-Kakizaki rats. Biosci. Biotechnol. Biochem. 73(5), 1033-1041 (2009). 3. Aoyahi, R., Funakoshi-Tago, M., Fujiwara, Y., et al. Coffee inhibits adipocyte differentiation via inactivation of PPARγ. Biol. Pharm. Bull. 37(11), 1820-1825 (2014). 4. Liao, J.C., Lee, K.T., You, B.J., et al. Raf/ERK/Nrf2 signaling pathway and MMP-7 expression involvement in the trigonelline-mediated inhibition of hepatocarcinoma cell migration. Food Nutr. Res. 59:29884, (2015). 5. Arlt, A., Sebens, S., Krebs, S., et al. Inhibition of the Nrf2 transcription factor by the alkaloid trigonelline renders pancreatic cancer cells more susceptible to apoptosis through decreased proteasomal gene expression and proteasome activity. Oncogene 32(40), 4825-4835 (2013). WARNING CAYMAN CHEMICAL THIS PRODUCT IS FOR RESEARCH ONLY - NOT FOR HUMAN OR VETERINARY DIAGNOSTIC OR THERAPEUTIC USE. 1180 EAST ELLSWORTH RD SAFETY DATA ANN ARBOR, MI 48108 · USA This material should be considered hazardous until further information becomes available. Do not ingest, inhale, get in eyes, on skin, or on clothing. Wash thoroughly after handling. Before use, the user must review the complete Safety Data Sheet, which has been sent via email to your institution. PHONE: [800] 364-9897 WARRANTY AND LIMITATION OF REMEDY [734] 971-3335 Buyer agrees to purchase the material subject to Cayman’s Terms and Conditions. Complete Terms and Conditions including Warranty and Limitation of Liability information can be found on our website. FAX: [734] 971-3640 [email protected] Copyright Cayman Chemical Company, 07/13/2016 WWW.CAYMANCHEM.COM.
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