535-83-1 Usage
Description
Trigonelline, also known as N-methylnicotinic acid, is a bitter alkaloid found in coffee beans and fenugreek seeds. It is the second most important alkaloid in coffee, after caffeine, and is a methylation product of niacin (vitamin B3). Trigonelline serves as a plant hormone with diverse regulatory functions, including cell cycle regulation, nodulation, and oxidative stress response, as well as promoting the survival and growth of plants. It is a white solid and has a chemical formula of C7H7NO2.
Uses
1. Used in Coffee Industry:
Trigonelline is used as a flavor compound in the coffee industry for its contribution to the aroma and taste of coffee. It is more concentrated in Arabica beans (0.6-1.3%) than in Robusta beans (0.3-0.9%).
2. Used in Pharmaceutical Applications:
Trigonelline is used as an antihyperglycemic agent, helping to regulate blood sugar levels and potentially offering benefits for individuals with diabetes.
3. Used in Plant Biology Research:
Trigonelline is used as a research tool in plant biology to study its role in plant cell cycle regulation, nodulation, and oxidative stress response, as well as its function in seed germination and plant growth.
4. Used in Nutritional Supplements:
Trigonelline, being a derivative of niacin (vitamin B3), can be used in nutritional supplements for its potential health benefits, including its role in energy production and maintaining healthy skin and nerves.
5. Used in Alkaloid Research:
Trigonelline is used in the study of alkaloids, particularly in understanding their chemical properties, synthesis, and potential applications in various industries.
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.