Trigonelline

Trigonelline
Names
Preferred IUPAC name
1-Methylpyridin-1-ium-3-carboxylate
Other names
Nicotinic acid N-methylbetaine
Coffearine
Caffearine
Gynesine
Trigenolline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.838 Edit this at Wikidata
UNII
  • InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 checkY
    Key: WWNNZCOKKKDOPX-UHFFFAOYSA-N checkY
  • InChI=1/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
    Key: WWNNZCOKKKDOPX-UHFFFAOYAV
  • O=C([O-])c1ccc[n+](c1)C
Properties
C7H7NO2
Molar mass 137.138 g·mol−1
Melting point 230 to 233 °C (446 to 451 °F; 503 to 506 K) (monohydrate)[contradictory]
258–259 °C (hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trigonelline is an alkaloid with chemical formula C7H7NO2. It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.[1]

Trigonelline occurs in many plants. It has been isolated from the Japanese radish[2] (Raphanus sativus cv. Sakurajima Daikon), fenugreek seeds (Trigonella foenum-graecum, hence the name),[3] garden peas, hemp seed, oats,[4] potatoes, Stachys species, dahlia,[5] Strophanthus species,[6] and Dichapetalum cymosum.[7] Trigonelline is also found in coffee.[8] Higher levels of trigonelline are found in arabica coffee.

Holtz, Kutscher, and Theilmann have recorded its presence in a number of animals.[9]

  1. ^ Merck Index, 11th Edition, 9606.
  2. ^ Kuroda, Rei; Kazumura, Kimiko; Ushikata, Miki; Minami, Yuji; Kajiya, Katsuko (2018). "Elucidating the Improvement in Vascular Endothelial Function from Sakurajima Daikon and its Mechanism of Action: A Comparative Study with Raphanus sativus". Journal of Agricultural and Food Chemistry. 66 (33): 8714–8721. doi:10.1021/acs.jafc.8b01750. PMID 30037222. S2CID 51712881.
  3. ^ Ouzir, Mounir; El Bairi, Khalid; Amzazi, Saaïd (2016). "Toxicological properties of fenugreek (Trigonella foenum graecum)". Food and Chemical Toxicology. 96: 145–154. doi:10.1016/j.fct.2016.08.003. PMID 27498339.
  4. ^ Schulze and Frankfurt, Ber., 1894, 27, 709.
  5. ^ Schulze and Trier, Zeit. physiol. Chem., 1912, 76, 258.
  6. ^ Thoms, Ber., 1891, 31, 271, 404.
  7. ^ Rimington, Onderstepoort J., 1935, 5, 81.
  8. ^ Gorter, Annalen, 1910, 372, 237; cf. Polstorff, Chem. Soc. Abstr., 1910, ii, 234; Palladino, ibid, 1894, ii, 214; 1895, i, 629; Graf, ibid, 1904, i, 915; Nottbohm and Mayer, Zeit. Unters. Lebensmitt., 1931, 61, 429.
  9. ^ Zeit. Biol., 1924, 81, 57.