Trigonelline

Base Information

• Chemical Name: Trigonelline
• CAS No.: 535-83-1
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 29339900
• European Community (EC) Number: 208-620-5
• NSC Number: 714350
• UNII: 3NQ9N60I00
• DSSTox Substance ID: DTXSID2026230
• Nikkaji Number: J1.414.545A
• Wikipedia: Trigonelline
• Wikidata: Q928965
• Metabolomics Workbench ID: 37479
• ChEMBL ID: CHEMBL350675
• Mol file: 535-83-1.mol

Synonyms:trigonelline;trigonelline chloride;trigonelline iodide;trigonelline ion;trigonelline tosylate

Chemical Property of Trigonelline

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 260°C (dec.)
• Refractive Index: 1.554
• Boiling Point: 266.433 °C at 760 mmHg
• Flash Point: 114.935 °C
• PSA: 44.01000
• Density: 1.217 g/cm³
• LogP: -1.12540
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 130

Purity/Quality:

20%, ^*data from raw suppliers

Trigonelline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1=CC=CC(=C1)C(=O)[O-]
• 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.
• Uses: 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). Trigonelline is an alkaloid present in coffee and fenugreek presenting phytoestrogenic activity.

Technology Process of Trigonelline

There total 17 articles about Trigonelline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

acycloguanosine (59277-89-3) + trigonelline anhydride diiodide → 1-Methyl-3-{[2-(9-guanylmethoxy)ethoxy]carbonyl}pyridinium iodide + Trigonelline (535-83-1)

Guidance literature:

dmap; In pyridine;

Reference yield:

N-Methylpyrrole (96-54-8) + carbon dioxide (124-38-9,18923-20-1) + pyrographite (7440-44-0) → Trigonelline (535-83-1) + N-methylpyridinium chloride (7680-73-1)

Guidance literature:

N-Methylpyrrole; carbon dioxide; pyrographite; at -196.15 ℃; electric arc;

With hydrogenchloride; In methanol; at -196.15 ℃;

DOI:10.1021/ja9639168

Reference yield:

3-Carboxy-1-methylpyridiniumiodid (6138-42-7) → Trigonelline (535-83-1)

Guidance literature:

With water; silver(l) oxide;

upstream raw materials:

nicotinic acid

methyl iodide

3-pyridinecarboxylic acid ethyl ester

3-Carboxy-1-methylpyridiniumiodid

Downstream raw materials:

N-methyl-3,4-didehydropiperidine

N-methylcyclohexylamine

pyridine

nicotinic acid

Refernces

• 1、 Mizuno, Kouichi,Matsuzaki, Masahiro,Kanazawa, Shiho,Tokiwano, Tetsuo,Yoshizawa, Yuko,Kato, Misako. "Conversion of nicotinic acid to trigonelline is catalyzed by N-methyltransferase belonged to motif B′ methyltransferase family in Coffea arabica". . p. 1060 - 1066. Retrieved 2014.
• 2、 Chevalier, Y.,Brunel, S.,Perchec, P. Le. "Syntheses et proprietes de tensioactifs zwitterioniques". . p. 1025 - 1042. Retrieved 2007/10/02.