Methylpyridinium

Methylpyridinium

Names
IUPAC name 1-Methylpyridinium
Other names N-Methylpyridinium
Identifiers
CAS Number	694-56-4
ChemSpider	13008
Jmol interactive 3D	Image
PubChem	13597
InChI InChI=1S/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1 Key: PQBAWAQIRZIWIV-UHFFFAOYSA-N InChI=1/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1 Key: PQBAWAQIRZIWIV-UHFFFAOYAW
SMILES [n+]1(ccccc1)C
Properties
Chemical formula	C6H8N^+
Molar mass	94.134 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methylpyridinium is a chemical compound which is the quaternary ammonium compound derived from the N-methylation of pyridine. It is found in some coffee products.^[1] It is not present in unroasted coffee beans, but is formed during roasting from its precursor chemical, trigonelline.^[1] It is under investigation by scientists regarding its potential anti-carcinogenic properties,^[2] particularly an effect on colon cancer.^[1]

Ionic liquid

The chloride of N-methylpyridinium behaves as an ionic liquid in the molten state. Its properties with different mixtures of zinc chloride have been characterised by several authors in the temperature range 150 – 200 °C (423 – 473 K).^{[3], [4], [5], [6]}

See also

• Pyridinium
• 4-Caffeoyl-1,5-quinide
• Coffee portal

References

1. "Highly Active Compound Found In Coffee May Prevent Colon Cancer". ScienceDaily. Oct 15, 2003. Retrieved 2012.
2. Boettler, U; Volz, N; Pahlke, G; Teller, N; Kotyczka, C; Somoza, V; Stiebitz, H; Bytof, G; et al. (2011). "Coffees rich in chlorogenic acid or N-methylpyridinium induce chemopreventive phase II-enzymes via the Nrf2/ARE pathway in vitro and in vivo". Molecular nutrition & food research 55 (5): 798–802. doi:10.1002/mnfr.201100115. PMID 21448860.
3. Simonis, L., Coppe, C., Glibert, J., & Claes, P. (1986). Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – I. Phase diagram and heats of mixing. Thermochimica acta, 99, 223-232. http://dx.doi.org/doi:10.1016/0040-6031(86)85285-6
4. Claes, P., Simonis, L., & Glibert, J. (1986). Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – II. Specific mass, electrical conductivity and viscosity. Electrochimica acta, 31(12), 1525-1530. http://dx.doi.org/doi:10.1016/0013-4686(86)87071-2
5. Claes, P. F., Coppe, C. R., Simonis, L. A., & Glibert, J. E. (1987). Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – III. Solubility of hydrogen chloride under atmospheric pressure and comparison with zinc chloride - N-ethylpyridinium bromide mixtures. Journal of Chemical and Engineering Data, 32(1), 70-72. http://dx.doi.org/doi:10.1021/je00047a020
6. Marković, R., & Minić, D. M. (1997). Conductometric and thermal studies of fused Zn (II) salts containing methyl substituted pyridinium cations. Materials chemistry and physics, 50(1), 20-24. http://dx.doi.org/doi:10.1016/S0254-0584(97)80178-2