535-83-1 Usage
Description
Trigonelline 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 Properties
White solid
Uses
Different sources of media describe the Uses of 535-83-1 differently. You can refer to the following data:
1. antihyperglycemic.
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).
2. Trigonelline is an alkaloid present in coffee and fenugreek presenting phytoestrogenic activity.
Definition
ChEBI: An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.
Biosynthesis
Trigonelline 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 Methods
Crystallise 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.]
References
Jahns., 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)
Check Digit Verification of cas no
The CAS Registry Mumber 535-83-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 5 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 535-83:
(5*5)+(4*3)+(3*5)+(2*8)+(1*3)=71
71 % 10 = 1
So 535-83-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-4H,5H2,1H3,(H,9,10)
535-83-1Relevant articles and documents
Ab initio and DFT calculations of the structure and vibrational spectra of trigonelline
Szafran,Koput,Dega-Szafran,Pankowski
, p. 97 - 108 (2002)
The geometries, frequencies and infrared intensities of the vibrational bands of trigonelline its monohydrate and dimer have been computed by the MP2 and B3LYP approaches using the cc-pVDZ and 6-31G(d,p) basis sets. The computed geometry of the pyridine ring is slightly affected by hydration and dimerization, and satisfactorily agrees with the X-ray data. In contrast, the geometry of the COO group changes significantly on hydration and dimerization. All the measured IR bands were assigned in terms of the calculated vibrational modes. Most computed bands are predicted to lie at higher wavenumbers than the experimental bands. R.M.S. deviation between the experimental and the calculated harmonic frequencies is 69 cm-1 for all of the bands, and 46 cm-1 for all bands except those corresponding to v(OH), δ(OH) and v(CH).
The chemistry of the N-methyl-3-dehydropyridinium ylid
Pan, Weitao,Shevlin, Philip B.
, p. 5091 - 5094 (2007/10/03)
The reaction of atomic carbon with N-methylpyrrole, 5b, at 77 K generates the N-methyl-3-dehydropyridinium ylid, 6b, which can be trapped with added hydrogen halides or CO2. The addition of CO2 is strong evidence for the ylid 6b rather than cumulene 7. Deuterium and 13C labeling studies demonstrate that 6b rapidly rearranges to the N-methyl-2-dehydropyridinium ylid, 13, by an intermolecular mechanism. Ylid 13 can be trapped with added acids or with O2 to form 1-methyl-2-pyridone.
Pharmaceutical formulations for parenteral use
-
, (2008/06/13)
Aqueous parenteral solutions of drugs which are insoluble or only sparingly soluble in water and/or which are unstable in water, combined with hydroxypropyl-β-cyclodextrin, provide a means for alleviating problems associated with drug precipitation at the injection site and/or in the lungs or other organs following parenteral administration.
