Trigonelline

Trigonelline Basic information
Product Name:Trigonelline
Synonyms:betainnicotinate;Caffearine;Coffearin;Coffearine;Gynesine;n’-methylnicotinicacid;Nicotinic acid N-methylbetaine;nicotinicacidn-methylbetaine
CAS:535-83-1
MF:C7H7NO2
MW:137.14
EINECS:208-620-5
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
Mol File:535-83-1.mol
Trigonelline Structure
Trigonelline Chemical Properties
Melting point 260°C (dec.)
Boiling point 251.96°C (rough estimate)
density 1.2528 (rough estimate)
refractive index 1.5030 (estimate)
storage temp. Refrigerator
solubility Methanol (Slightly), Water (Slightly)
form Solid
color Off-White to Light Beige
LogP-3.910 (est)
Safety Information
Safety Statements 24/25
HS Code 29339900
Hazardous Substances Data535-83-1(Hazardous Substances Data)
MSDS Information
Trigonelline Usage And Synthesis
DescriptionTrigonelline is a bitter alkaloid in coffee which serves to produce important aroma compounds. In terms of concentration trigonelline is higher for arabica than robusta and ranges from about 0.6-1.3% and 0.3-0.9%, respectively.
Trigonelline, the N-methylpyridinium-3-carboxylate, is, after caffeine, the second most important alkaloid of coffee, with about 1% of the green bean. During leaf development, it is synthesized in the leaves and in the fruits' pericarp and accumulated in the seeds. The direct precursors are nicotinic acid and nicotine amide, deriving from the pyridine nucleotide cycle.
Trigonelline is a plant hormone that has diverse regulatory functions with respect to plant cell cycle regulation, nodulation, and oxidative stress, and in helping survival and growth of the plant. It is found in significant quantity in many plants like coffee beans and fenugreek seed. Because it was first isolated from the fenugreek seeds (Trigonella foenum-graecum), the name assigned to it has been “trigonelline.” The chemical formula for trigonelline is C7H7NO2. It is a methylation product of niacin (vitamin B3), and thus is also known as “methylated niacin.” At higher temperatures, trigonelline breaks down to niacin. In addition to trigonelline, fenugreek seeds contain other alkaloids such as gentianine and carpaine.

Chemical PropertiesWhite solid
Usesantihyperglycemic.
Trigonelline is an inhibitor which, like abscicic acid, accumulates in plant cells when the plant becomes dormant or is exposed to stress. This natural inhibitor is chemically related to glycine betaine. It has been found in dormant winter buds of Populus trichocarpa * deltoides trees in the field as well as in salt-stressed micropropagules thereof. Some trigonelline also occurred in non-stressed micropropagules, probably as the result of bioconversion of niacin taken up from the nutrient medium (Bray et al. 1988). Trigonelline preferentially promotes arrest in G2 of the cell cycle and appears to have a growth controlling function during seed germination (Evans and Tramontano 1981).
UsesTrigonelline is an alkaloid present in coffee and fenugreek presenting phytoestrogenic activity.
DefinitionChEBI: An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.
BiosynthesisTrigonelline is synthesized by the methylation of nicotinic acid. This reaction is catalyzed by Sadenosyl-L-methionine (SAM) dependent nicotinate N-methyltransferase (EC 2.1.1.7), which is found in crude extracts of the pea. This enzyme has now been purified from heterotrophic cultured cells and leaves of Glycine max. The Km values for nicotinate and SAM were 78 μM and 55 μM, respectively in the enzyme derived from cultured cells, and 12.5 μM and 31 μM in leaves. The optimum pH of the cultured cell enzyme is alkaline (8.0), but that of the leaf enzyme is acidic (6.5). The gene encoding trigonelline synthase has not yet been cloned from any organism.
Purification MethodsCrystallise trigonelline (as monohydrate) from aqueous EtOH, then dry it at 100o. It also crystallises from H2O as the monohydrate with m 230-233o(dec). It has been crystallised from EtOH with m 214-215o(dec). The picrate crystallises from EtOH with m 204-206o. [Green & Tong J Am Chem Soc 78 4896 1956, Kosower & Patton J Org Chem 26 1319 1961, Beilstein 22 III/IV 462, 22/2 V 143.]
ReferencesJahns., Ber., 18,2518 (1885)
Thoms., ibid, 31,271,404 (1891)
Schultz, Frankfurt., ibid, 27,709 (1894)
Gorter., Annalen, 372,237 (1910)
Schultz, Trier., Zeit. physiol. Chem., 76,258 (1912)
Holtz, Kutscher, Theilmann., Zeit. Bioi., 8, 57 (1924)
Rimington., Onderstepoort J., 5, 81 (1935)
Pharmacology :
Ackermann., Zeit. Bioi., 59, 17 (1912)
Volmer, Furst., Bull. Acad. Med., 122,241 (1939)






Trigonelline Preparation Products And Raw materials
Raw materials1-Methylpyridinium chloride-->CARBON DIOXIDE-->Carbon-->N-Methyl pyrrole
Banaba Leaf Extract Astragaloside A ELEUTHEROSIDE E1 Rosmarinic acid Vitexin Common Fenugreek Seed P.E. N-Benzylniacin TRIGONELLINE(RG) TRIGONELLINE MONOHYDRATE 1-BENZYL-3-SODIUMCARBOXY-PYRIDINIUM CHLORIDE Trigonelline amide Trigonelline TRIGONELLINE HCL SPECS AJ-333/25022083 1-METHYL-2-SULFANYLPYRIDINIUM-3-CARBOXYLATE Trigonelline sulfate Trigonelline chloride,TRIGONELLINE HCL,TRIGONELLINE HYDROCHLORIDE NIACIN RIBOSIDE, [CARBOXYL-14C]-

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