273:
198:
24:
412:
649:
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
582:
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
574:
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•AuCl
425:
322:
562:
in hygroscopic prisms (m.p. 130 °C or 218 °C ). It is readily soluble in water or warm alcohol, less so in cold alcohol, and slightly so in
887:
287:
108:
432:
230:
598:
at 120 °C, it gives rise to methylamine, and, if treated similarly with hydrochloric acid at 260 °C creates
251:
897:
193:
155:
148:
570:. The salts crystallize well, the monohydrochloride, in leaflets, sparingly soluble in dry alcohol. The
23:
902:
892:
531:
36:
268:
74:
882:
679:
487:
697:
Ouzir, Mounir; El Bairi, Khalid; Amzazi, Saaïd (2016). "Toxicological properties of fenugreek (
718:
671:
498:
710:
663:
595:
494:). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.
452:
345:
239:
555:
175:
84:
272:
197:
128:
603:
540:
403:
876:
599:
579:
389:
186:
683:
567:
525:
546:
Holtz, Kutscher, and
Theilmann have recorded its presence in a number of animals.
219:
631:
483:
714:
563:
479:
376:
166:
667:
506:
722:
675:
497:
Trigonelline occurs in many plants. It has been isolated from the
Japanese
468:
462:
448:
394:
230 to 233 °C (446 to 451 °F; 503 to 506 K) (monohydrate)
611:
571:
559:
515:
206:
536:
520:
471:
456:
139:
402:
Except where otherwise noted, data are given for materials in their
865:(4th ed.). Philadelphia: The Blakiston Company. pp. 7–8.
119:
107:
97:
256:
513:, hence the name), garden peas, hemp seed, oats, potatoes,
420:
296:InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
594:When trigonelline is heated in closed tubes with
306:InChI=1/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
218:
83:
539:. Higher levels of trigonelline are found in
8:
656:Journal of Agricultural and Food Chemistry
271:
196:
174:
15:
238:
474:
465:
459:
623:
327:
292:
267:
591:(m.p. 186 °C) are obtained.
187:
299:Key: WWNNZCOKKKDOPX-UHFFFAOYSA-N
154:
147:
127:
7:
823:1894, ii, 214; 1895, i, 629; Graf,
309:Key: WWNNZCOKKKDOPX-UHFFFAOYAV
209:
41:1-Methylpyridin-1-ium-3-carboxylate
827:1904, i, 915; Nottbohm and Mayer,
14:
578:, is precipitated when excess of
535:. Trigonelline is also found in
410:
396:258–259 °C (hydrochloride)
363:
357:
22:
861:Anderson Henry, Thomas (1949).
406:(at 25 °C , 100 kPa).
366:
351:
1:
888:Quaternary ammonium compounds
703:Food and Chemical Toxicology
610:). Trigonelline is a methyl
919:
829:Zeit. Unters. Lebensmitt.,
819:1910, ii, 234; Palladino,
715:10.1016/j.fct.2016.08.003
699:Trigonella foenum graecum
511:Trigonella foenum-graecum
400:
338:
318:
283:
67:
47:
35:
30:
21:
668:10.1021/acs.jafc.8b01750
505:cv. Sakurajima Daikon),
486:of the nitrogen atom of
735:Schulze and Frankfurt,
558:as a monohydrate from
754:Zeit. physiol. Chem.,
606:(a form of vitamin B
532:Dichapetalum cymosum
37:Preferred IUPAC name
863:The Plant Alkaloids
752:Schulze and Trier,
614:of nicotinic acid.
384: g·mol
18:
817:Chem. Soc. Abstr.,
433:Infobox references
16:
788:Onderstepoort J.,
662:(33): 8714–8721.
441:Chemical compound
439:
438:
252:CompTox Dashboard
109:Interactive image
910:
898:Coffee chemistry
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652:Raphanus sativus
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635:, 11th Edition,
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596:barium hydroxide
503:Raphanus sativus
477:
453:chemical formula
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428: ?)
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330:O=C()c1ccc(c1)C
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50:Nicotinic acid
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5:
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604:nicotinic acid
588:
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541:arabica coffee
491:
482:formed by the
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54:-methylbetaine
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600:chloromethane
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592:
581:
580:gold chloride
573:
569:
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557:
554:Trigonelline
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529:species, and
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390:Melting point
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269:DTXSID2026230
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188:ECHA InfoCard
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34:
29:
25:
20:
17:Trigonelline
862:
856:
848:
845:Zeit. Biol.,
844:
840:
832:
828:
824:
820:
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630:
626:
593:
556:crystallizes
553:
545:
530:
526:Strophanthus
524:
514:
510:
502:
496:
445:Trigonelline
444:
443:
156:ChEMBL489961
149:ChEMBL350675
68:Identifiers
62:Trigenolline
51:
48:Other names
903:Zwitterions
893:Nicotinates
815:Polstorff,
786:Rimington,
709:: 145–154.
632:Merck Index
484:methylation
339:Properties
194:100.007.838
129:CHEBI:18123
877:Categories
618:References
564:chloroform
490:(vitamin B
480:zwitterion
478:. It is a
377:Molar mass
240:3NQ9N60I00
167:ChemSpider
96:3D model (
75:CAS Number
58:Caffearine
56:Coffearine
883:Alkaloids
777:271, 404.
550:Chemistry
519:species,
507:fenugreek
805:Annalen,
803:Gorter,
723:27498339
684:51712881
676:30037222
587:•3 HAuCl
449:alkaloid
85:535-83-1
60:Gynesine
769:Thoms,
612:betaine
572:picrate
560:alcohol
516:Stachys
509:seeds (
426:what is
424: (
382:137.138
207:PubChem
847:1924,
831:1931,
807:1910,
790:1935,
773:1891,
756:1912,
739:1894,
721:
682:
674:
537:coffee
521:dahlia
499:radish
488:niacin
447:is an
421:verify
418:
323:SMILES
140:ChEMBL
31:Names
825:ibid,
821:ibid,
811:237;
771:Ber.,
737:Ber.,
680:S2CID
568:ether
451:with
288:InChI
120:ChEBI
98:JSmol
835:429.
809:372,
760:258.
743:709.
719:PMID
701:)".
672:PMID
637:9606
602:and
231:UNII
220:5570
176:5369
851:57.
849:81,
833:61,
813:cf.
794:81.
775:31,
758:76,
741:27,
711:doi
664:doi
654:".
566:or
257:EPA
210:CID
879::
792:5,
717:.
707:96
705:.
678:.
670:.
660:66
658:.
543:.
523:,
725:.
713::
686:.
666::
639:.
608:3
589:4
585:4
583:B
576:3
501:(
492:3
475:2
472:O
469:N
466:7
463:H
460:7
457:C
416:N
370:2
367:O
364:N
361:7
358:H
355:7
352:C
259:)
255:(
100:)
52:N
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