Trigonelline

Trigonelline
Names
IUPAC name
1-Methylpyridinium-3-carboxylate
Other names
Nicotinic acid N-methylbetaine
Coffearine
Caffearine
Gynesine
Trigenolline
Identifiers
535-83-1 N
3D model (Jmol) Interactive image
ChEBI CHEBI:18123 YesY
ChEMBL ChEMBL350675 YesY
ChEMBL489961 YesY
ChemSpider 5369 YesY
ECHA InfoCard 100.007.838
PubChem 5570
Properties
C7H7NO2
Molar mass 137.14 g·mol−1
Melting point 230 to 233 °C (446 to 451 °F; 503 to 506 K) (monohydrate)
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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Infobox references

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 urine of mammals.[1]

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

Holtz, Kutscher, and Theilmann have recorded its presence in a number of animals.[8]

Chemistry

Trigonelline crystallizes as a monohydrate from alcohol in hygroscopic prisms (m.p. 130 °C or 218 °C [dry, dec.]). It is readily soluble in water or warm alcohol, less so in cold alcohol, and slightly so in chloroform or ether. The salts crystallize well, the monohydrochloride, in leaflets, sparingly soluble in dry alcohol. The picrate forms shining prisms (m.p. 198−200 °C) soluble in water but sparingly soluble in dry alcohol or ether. The alkaloid forms several aurichlorides: the normal salt, B•HCl•AuCl3, is precipitated when excess of gold chloride is added to the hydrochloride, and, after crystallization from dilute hydrochloric acid containing some gold chloride, has m.p. 198 °C. Crystallized from water or very dilute hydrochloric acid, slender needles of B4•3 HAuCl4 (m.p. 186 °C) are obtained.

When trigonelline is heated in closed tubes with barium hydroxide at 120 °C, it gives rise to methylamine, and, if treated similarly with hydrochloric acid at 260 °C creates chloromethane and nicotinic acid (a form of vitamin B3). Trigonelline is a methyl betaine of nicotinic acid.[9]

References

  1. ↑ Merck Index, 11th Edition, 9606.
  2. ↑ Ouzir, M; El Bairi, K; Amzazi, S (October 2016). "Toxicological properties of fenugreek (Trigonella foenum graecum).". Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 96: 145–54. PMID 27498339.
  3. ↑ Schulze and Frankfurt, Ber., 1894, 27, 709.
  4. ↑ Schulze and Trier, Zeit. physiol. Chem., 1912, 76, 258.
  5. ↑ Thoms, Ber., 1891, 31, 271, 404.
  6. ↑ Rimington, Onderstepoort J., 1935, 5, 81.
  7. ↑ 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.
  8. ↑ Zeit. Biol., 1924, 81, 57.
  9. ↑ http://library.sciencemadness.org/library/books/the_plant_alkaloids.pdf
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