Name | 1-methylpyridinio-3-carboxylate |
Synonyms | Gynesine Coffearin Coffearine Caffearine trigonelline betainnicotinate n'-methylnicotinicacid nicotinicacidn-methylbetaine Nicotinic acid N-methylbetaine 1-methylpyridinio-3-carboxylate 1-methylpyridinium-3-carboxylate 1-methyl-1,2-dihydropyridine-3-carboxylic acid |
CAS | 535-83-1 |
EINECS | 208-620-5 |
InChI | InChI=1/C7H9NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-4H,5H2,1H3,(H,9,10) |
Molecular Formula | C7H7NO2 |
Molar Mass | 137.14 |
Density | 1.2528 (rough estimate) |
Melting Point | 260°C (dec.) |
Boling Point | 251.96°C (rough estimate) |
Flash Point | 114.935°C |
Solubility | Soluble in methanol and water |
Vapor Presure | 0.002mmHg at 25°C |
Appearance | White crystalline powder |
Color | Off-White to Light Beige |
Storage Condition | Refrigerator |
Sensitive | Easily absorbing moisture |
Refractive Index | 1.5030 (estimate) |
MDL | MFCD00054262 |
Physical and Chemical Properties | White crystalline powder, soluble in methanol and water, derived from fenugreek, make a gentleman, soybean. |
In vitro study | It is found that Trigonelline (TG) significantly rescues the morphology of the H9c2 cells. Treatment of cells with Trigonelline attenuates H 2 O 2 induced cell deaths and improves the antioxidant activity. In addition, Trigonelline regulates the apoptotic gene caspase-3, caspase-9 and anti-apoptotic gene Bcl-2, Bcl-XL during H 2 O 2 induced oxidative stress in H9c2 cells. For evident, flow cytometer results also confirms that Trigonelline significantly reduces the H 2 O 2 induced necrosis and apoptosis in H9c2 cells. However, further increment of Trigonelline concentration against H 2 O 2 can induce the necrosis and apoptosis along with H 2 O 2 . |
In vivo study | Trigonelline decreases bone mineralization and tends to worsen bone mechanical properties in streptozotocin-induced diabetic rats. In nicotinamide/streptozotocin-treated rats, Trigonelline significantly increases bone mineral density (BMD) and tends to improve cancellous bone strength. Trigonelline differentially affects the skeletal system of rats with streptozotocin-induced metabolic disorders, intensifying the osteoporotic changes in streptozotocin-treated rats and favorably affecting bones in the non-hyperglycemic (nicotinamide/streptozotocin-treated) rats. |
Safety Description | 24/25 - Avoid contact with skin and eyes. |
HS Code | 29339900 |
Reference Show more | 1. Ji Caihong, Jin Jing, Xu Yueming, etc. Effects of endogenous substances on degradation of thiophanate-methyl in cherry tomato plants [J]. Pesticides, 2020, v.59(01):40-43. 2. Yu Yue, Liu Jing, Deng Bo, etc. Effects of exogenous root exudates on rhizobia symbiotic system of Medicago sativa [J]. Journal of Grassland Science, 2020. 3. [IF = 9.642] Shan Huang et al."Identification and quantitative chemical analysis of betaines in different organic waves and their bioconversion composites." Bioresource Technol. 2021 May;328:124857 4. [IF = 6.543] Zeng Wen-Yu et al."Trigonelline Extends the Lifespan of C. Elegans and Delays the Progression of Age-Related Diseases by Activating AMPK, DAF-16, and HSF-1."Oxid Med Cell Longev. 2021;2021:7656834 5. [IF=4.411] Simona S. Ghanem et al."Natural Alkaloid Compounds as Inhibitors for Alpha-Synuclein Seeded Fibril Formation and Toxicity."Molecules. 2021 Jan;26(12):3736 |
Plant source: | Fenugreek |
biological activity | Trigonelline (Trigenolline) is a plant alkaloid, which is the main component of coffee and fenugreek. it has anti-degranulation, anti-diabetes, anti-oxidation, anti-inflammatory and neuroprotective effects. Trigonelline can inhibit FcεRI-mediated intracellular signaling pathways, such as phosphorylation of PLCγ1, PI3K and Akt. Trigonelline (Trigenolline) can also inhibit the formation of microtubule in RBL-2H3 cells. |
Target | Value |
use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effect: It is the main component of fenugreek and has anti-tumor effect. Used as a nutritional additive, pharmaceutical intermediate |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |