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CAS No.: | 535-83-1 |
---|---|
Name: | TRIGONELLINE |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C7H7NO2 |
Molecular Weight: | 137.138 |
Synonyms: | Pyridinium,3-carboxy-1-methyl-, hydroxide, inner salt (8CI);Betaine nicotinate;Caffearine;Coffearin;Coffearine;Gynesine;N-Methylnicotinate;N-Methylnicotinic acid;Trigenolline;Trigonelline;1-methyl-1,2-dihydropyridine-3-carboxylic acid;N-methylnicotinic acid; |
EINECS: | 208-620-5 |
Density: | 1.217 g/cm3 |
Melting Point: | 260°C (dec.) |
Boiling Point: | 266.433 °C at 760 mmHg |
Flash Point: | 114.935 °C |
Safety: | 24/25 |
PSA: | 44.01000 |
LogP: | -1.12540 |
Conditions | Yield |
---|---|
dmap In pyridine | A 87% B n/a |
dmap In pyridine | A 87% B n/a |
dmap In pyridine | A 87% B n/a |
Conditions | Yield |
---|---|
at 100 - 150℃; Behandeln des Reaktionsprodukts mit Silberoxid in H2O; | |
With triethylamine In benzene |
Conditions | Yield |
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at 100 - 150℃; Behandeln des Reaktionsprodukts mit Silberoxid in H2O; |
Conditions | Yield |
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With water; silver(l) oxide | |
With methyloxirane In water for 72h; |
3-cyano-1-methyl-6-piperidino-1,6-dihydropyridine
A
2-imino-1-methyl-1,2-dihydro-pyridine-3-carbaldehyde
B
Trigonelline
C
2-methylamino-3-pyridinecarboxaldehyde
D
(2Z,4E)-2-Formyl-5-piperidin-1-yl-penta-2,4-dienenitrile
Conditions | Yield |
---|---|
With water Ambient temperature; Further byproducts given; | A 0.14 g B 0.68 g C 0.04 g D 0.26 g |
1'-Methyl-3,4,5,6,1',2'-hexahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid amide
A
Trigonelline
Conditions | Yield |
---|---|
With water Ambient temperature; | A 0.11 g B 0.01 g |
Conditions | Yield |
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Multi-step reaction with 3 steps 2: 70 percent / neat (no solvent) / 2 h / Ambient temperature 3: 0.11 g / water / Ambient temperature View Scheme |
nicotinic acid
S-Adenosyl-L-methionine
Trigonelline
Conditions | Yield |
---|---|
With coffee trigonelline synthase; magnesium chloride In aq. buffer at 25℃; pH=7.5; Reagent/catalyst; Enzymatic reaction; |
Trigonelline
trifluoroacetic anhydride
N-Methyl-pyridinio-3-carbonsaeure-betain-trifluoracetat
Conditions | Yield |
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66% |
Trigonelline
Conditions | Yield |
---|---|
With sodium borohydrid; sodium carbonate In methanol; thionyl chloride; ethanol; N,N-dimethyl-formamide | 18% |
The Trigonelline, with the CAS registry number 535-83-1 and EINECS registry number 208-620-5, has the IUPAC name of 1-Methylpyridinium- 3-carboxylate. It is readily soluble in water or warm alcohol, less so in cold alcohol, and slightly so in chloroform or ether.And the molecular formula of the chemical is C7H7NO2.
The Trigonelline is an alkaloid, and occurs in many plants. And can be isolated from fenugreek seeds, garden peas, hemp seed, oats, potatoes, Stachys species, dahlia, Strophanthus species and Dichapetalum cymosum. It is also found in coffee.
The physical properties of Trigonelline are as following: (1)ACD/LogP: 1.06; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 40.54 ?2; (11)Index of Refraction: 1.554; (12)Molar Refractivity: 36.644 cm3; (13)Molar Volume: 114.337 cm3; (14)Polarizability: 14.527 10-24cm3; (15)Surface Tension: 47.866 dyne/cm; (16)Density: 1.217 g/cm3; (17)Flash Point: 114.935 °C; (18)Enthalpy of Vaporization: 55.524 kJ/mol; (19)Boiling Point: 266.433 °C at 760 mmHg; (20)Vapour Pressure: 0.002 mmHg at 25°C.
Preparation and uses of 3-Fluoro-4-phenylhydratropic acid: It can be prepared via the oxidation, esterification, transesterification, hydrolysis and decarboxylation of 2-fluoride acetophenone. What's more, it is an anti-inflammatory used as an analgesic.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C=1CN(C)/C=C\C=1
(2)InChI: InChI=1/C7H9NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-4H,5H2,1H3,(H,9,10)
(3)InChIKey: YCABHAGDPZAUBJ-UHFFFAOYAI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 5gm/kg (5000mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 210, Pg. 27, 1974. | |
rat | LD50 | subcutaneous | 5gm/kg (5000mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 62, Pg. 19, 1946. |