Tetramethylpyrazine
- CAS No.
- 1124-11-4
- Chemical Name:
- Tetramethylpyrazine
- Synonyms
- 2,3,5,6-TETRAMETHYLPYRAZINE;Ligustrazine;FEMA 3237;Pyrazine,tetramethyl-;Tetramethylpyrazin;2,3,5,6-TetramethyL;BS Factor;Ligustizine;TETRAPYRAZINE;Chuanxingzine
- CBNumber:
- CB6186289
- Molecular Formula:
- C8H12N2
- Molecular Weight:
- 136.19
- MOL File:
- 1124-11-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/21 22:41:43
| Melting point | 77-80 °C(lit.) |
|---|---|
| Boiling point | 190 °C(lit.) |
| Density | 1.08 |
| FEMA | 3237 | 2,3,5,6-TETRAMETHYLPYRAZINE |
| refractive index | 1.5880 (estimate) |
| Flash point | 128-130°C/200mm |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | 4g/l |
| pka | 3.20±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| Odor | at 10.00 % in dipropylene glycol. nutty musty chocolate coffee cocoa brown lard burnt |
| Odor Type | nutty |
| Water Solubility | Soluble in water (4 g/L at 20°C). |
| JECFA Number | 780 |
| BRN | 113100 |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| InChIKey | FINHMKGKINIASC-UHFFFAOYSA-N |
| LogP | 1.56 |
| CAS DataBase Reference | 1124-11-4(CAS DataBase Reference) |
| NIST Chemistry Reference | Pyrazine, tetramethyl-(1124-11-4) |
| EPA Substance Registry System | Tetramethylpyrazine (1124-11-4) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | Xn,Xi | |||||||||
| Risk Statements | 22-37/38-41-36/37/38 | |||||||||
| Safety Statements | 26-39-24/25-37/39-36 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UQ3905000 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29339990 | |||||||||
| NFPA 704 |
|
Tetramethylpyrazine price More Price(11)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | W323713 | 2,3,5,6-Tetramethylpyrazine natural, ≥98%, FG | 1124-11-4 | 1SAMPLE-K | ₹5347.55 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W323713 | 2,3,5,6-Tetramethylpyrazine natural, ≥98%, FG | 1124-11-4 | 100G | ₹41535.53 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W323705 | 2,3,5,6-Tetramethylpyrazine ≥98%, FG | 1124-11-4 | 1SAMPLE-K | ₹5141.88 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W323713 | 2,3,5,6-Tetramethylpyrazine natural, ≥98%, FG | 1124-11-4 | 1KG | ₹315743.6 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W323705 | 2,3,5,6-Tetramethylpyrazine ≥98%, FG | 1124-11-4 | 250G | ₹15652.95 | 2022-06-14 | Buy |
Tetramethylpyrazine Chemical Properties,Uses,Production
Description
2,3,5,6-Tetramethylpyrazine is an alkaloid that has been found in L. wallichii and has diverse biological activities. It reduces kainate-induced increases in production of reactive oxygen species (ROS) and cytotoxicity in primary rat hippocampal neurons when used at a concentration of 5 μM. 2,3,5,6-Tetramethylpyrazine (0.1 mM) induces vasodilation in precontracted isolated and endothelium-denuded rat tail artery strips and reduces blood pressure in anesthetized rats. It decreases infarct volume, caspase-3 activation, and hypoxia-inducible factor-1α (HIF-1α) levels in a rat model of focal cerebral ischemia induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 20 mg/kg.
Chemical Properties
2,3,5,6-Tetramethylpyrazine has musty, fermented, coffee odor
Occurrence
Reported found in French fried potato, bell pepper, wheat bread, emmental cheese, Swiss cheese, Camembert cheese, Gruyere cheese, boiled and cooked beef, grilled and roasted beef, fried beef, cooked lamb and mutton, lamb and mutton liver, grilled and roasted uncured pork, beer, black tea, green tea. Also reported present in cocoa products, coffee, dairy products, oatmeal, galbanum oil, roasted peanuts, soybean, beans, mushroom, trassi, coriander seed, rice bran, trassi, sukiyaki, soy sauce, malt, licorice, dried bonito, wild rice, shrimp, crab, clam, scallop, filberts, rum, sake, wine, whiskey, burley tobacco and soy products.
History
Ligusticum walliichi has a long medicinal history in China and is used in the treatment of headache, promoting blood and Qi circulation, curing chills and alleviating
pain”. Clinically, it is mainly used for the treatment of cardiovascular and cerebrovascular diseases. Ligustrazine (2,3,5,6-tetramethylpyrazine) is the main active
ingredient of Ligusticum walliich. It was first isolated in 1962 .
In recent years, studies have found that ligustrazine can inhibit the activity of the
cerebral cortex and medullary respiratory center, excite vasomotors, induce the
expansion of peripheral blood vessels, promote the blood flow of the coronary artery
and lower limbs, and reduce blood pressure. Ligustrazine can also paralyze the
nerve center and has sedative and analgesic effects.
Studies have suggested that ligustrazine has a variety of new effects, including
improving leptomeningeal and peripheral microcirculation and increasing cerebral
blood flow, and its effect is better than that of papaverine. Ligustrazine can also
protect against experimental cerebral ischemia and alleviate brain edema and the
deposition of fibrin in microvessels. Ligustrazine is also used in the treatment of
pulmonary heart disease, heart failure, dilated heart disease, portal hypertension,
type II diabetes mellitus, tumor and coronary heart disease, and restenosis after
stent implantation .
Uses
etramethylpyrazine is an anti-inflammatory compound isolated from the fermented food natto. Tetramethylpyrazine demonstrated in vivo nootropic activity in rats.
Indications
Ligustrazine is used for occlusive vascular diseases, cerebral thrombosis, vasculitis, coronary heart disease, angina pectoris, and others
Preparation
From2,5-dimethylpyrazine by ring alkylationwithMeLi; also by condensation of 2,3-butanedionewith 2,3-butanediamine.
Definition
ChEBI: A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).
General Description
2,3,5,6-Tetramethylpyrazine has been isolated from Ephedra sinica. It is useful in the treatment of several disorders such as asthma, heart failure, rhinitis and urinary incontinence. It is a flavor ingredient of tobacco. It forms cocrystal with 4-hydroxybenzoic acid which exhibits supramolecular synthon polymorphism.
Clinical Use
The main clinical formulation of ligustrazine is ligustrazine hydrochloride injection.
Ligustrazine hydrochloride injection was used to prevent restenosis following coronary stent implantation and to treat acute coronary syndrome and ischemic stroke.
Ligustrazine hydrochloride injection is helpful in alleviating pulmonary hypertension in patients with pulmonary heart disease. The therapeutic effect of ligustrazine
hydrochloride injection on severe cholestatic liver cirrhosis caused by chronic heart
failure of rheumatic heart disease is remarkable. In addition, ligustrazine is widely
used in the treatment of vertigo syndrome, vertebrobasilar insufficiency, tension
headache, and so on. It has a good symptomatic-treatment effect .
Ligustrazine is also reported for the treatment of children with viral myocarditis,
chronic renal failure, hepatic fibrosis, portal hypertension, tumors, and diabetic
nephropathy. Ligustrazine can relieve symptoms rapidly, and its effect is stable and
lasting. It has good clinical promotion value .
Safety Profile
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.
Tetramethylpyrazine Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
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