1124-11-4

  • Product Name:Tetramethylpyrazine
  • Molecular Formula:C8H12N2
  • Purity:99%
  • Molecular Weight:136.197
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Product Details;

CasNo: 1124-11-4

Molecular Formula: C8H12N2

Appearance: white crystals or powder

Manufacturer supply top purity Tetramethylpyrazine 1124-11-4 with ISO standards

  • Molecular Formula:C8H12N2
  • Molecular Weight:136.197
  • Appearance/Colour:white crystals or powder 
  • Vapor Pressure:0.671mmHg at 25°C 
  • Melting Point:82-86 °C 
  • Refractive Index:1.503 
  • Boiling Point:192.7 °C at 760 mmHg 
  • PKA:3.20±0.10(Predicted) 
  • Flash Point:71.6 °C 
  • PSA:25.78000 
  • Density:1.08 g/cm3 
  • LogP:1.71020 

Tetramethylpyrazine(Cas 1124-11-4) Usage

Chemical Characteristic

White crystal or powder. With aroma of beef and heated lard and fermented soybean flavor. It smells chocolate flavor when diluted to 20mg/kg. Boiling point is 190℃. Melting point is between 84 and 86℃. Soluble in ethanol, most non-volatile oils and propylene glycol, slightly soluble in water. Natural products exist in guava, roast beef, cocoa, coffee, shrimp and so on.

Preparation

Butanedione monoxime generated by butanone and ethyl nitrite condensation is reduced and cyclized to produce methylpyrazine. The cyclization reaction product is subjected to steam distillation and the distillate is cooled,crystallized and filtered to generate crude tetramethylpyrazine which is refined with water recrystallization and activated carbon to decolor. Ethanol solution with 15% to 20% hydrogen chloride can be added into acetone to prepare hydrochloride salt. Condensed by 2,3-butanedione and 2,3-butanediamine.

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 .

Indications

Ligustrazine is used for occlusive vascular diseases, cerebral thrombosis, vasculitis, coronary heart disease, angina pectoris, and others

Pharmacology

Traditional Chinese medicine has some advantages in comprehensive treatment under multisite, multitarget conditions and overall regulation. Ligustrazine can inhibit phosphodiesterase activity and inhibit platelet aggregation. It has the typical characteristics of a calcium antagonist and can adjust the release of various vasoactive substances against the vasoconstrictive action of the sympathetic nerve, improve microcirculation, reduce red blood cell aggregation, shorten the erythrocyte electrophoresis time, and thereby reduce blood viscosity .Ligustrazine can inhibit the proliferation of vascular endothelial cells induced by vascular endothelial growth factor, which may be one of the mechanisms by which angiogenesis is inhibited. The mechanism by which ligustrazine inhibits the proliferation of vascular endothelial cells may be through calcium ion retardation, inhibition of cell adhesion molecules, or through the antagonistic or synergistic effects of some growth factors involved in the proliferation and angiogenesis of vascular endothelial cellsStudies have shown that ligustrazine plays a role in resistance to ischemiareperfusion injury and antiapoptotic effects via the phosphatidylinositol 3- kinase/ protein kinase B (PI3K/Akt) pathway. The phosphorylation of endothelial nitric oxide synthase (eNOS) and generation of nitric oxide (NO) are important downstream effectors, which significantly enhance the myocardial protective effects of ligustrazine. one of the mechanisms of resistance to fibrosis .

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.

Physical properties

Appearance: colorless needle crystal. Solubility: soluble in hot water, petroleum ether, chloroform, dilute hydrochloric acid, slightly soluble in ether, insoluble in cold water. Melting point: 77–80°C. Boiling point: 190°C. Flash point: 128– 130°C/200mm. Ligustrazine has a particular odor, moisture absorption, and sublimation.

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).

Aroma threshold values

Detection: 1 to 10 ppm. Aroma characteristics at 1.0%: slightly musty, nutty, cocoa-like with a vanilla undernote

Taste threshold values

Taste characteristics at 10 ppm: weak, nutty, musty cocoa and chocolate-like with dry coffee nuances.

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.

InChI:InChI=1/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

1124-11-4 Relevant articles

-

Zavyalov,Ezhova

, (1979)

-

Mechanistic Studies of 2-(1-Hydroxyethyl)-2,4,5-trimethyl-3-oxazoline Formation under Low Temperature in 3-Hydroxy-2-butanone/Ammonium Acetate Model Systems

Fu, Hui-Yin,Ho, Chi-Tang

, p. 1878 - 1882 (1997)

Volatile compounds formed from the react...

Combined effects of a buffer and solvent on tetramethylpyrazine formation in a 3-hydroxy-2-butanone/ammonium hydroxide system

Huang

, p. 1013 - 1015 (1997)

A phosphate buffer was found to signific...

Formation of 2-(1-Hydroxyalkyl)-3-oxazolines from the Reaction of Acyloins and Ammonia Precursors under Mild Conditions

Shu, Chi-Kuen,Lawrence, Brian M.

, p. 2922 - 2924 (1995)

Studies on the reaction between acetoin ...

-

Klein,Berkowitz,Hetman

, p. 126 (1961)

-

Mechanistic Studies of Tetramethylpyrazine Formation under Weak Acidic Conditions and High Hydrostatic Pressure

Huang, Tzou-Chi,Fu, Hui-Yin,Ho, Chi-Tang

, p. 240 - 246 (1996)

A significant enhancement of the tetrame...

Chemo-Enzymatic Synthesis of Pyrazines and Pyrroles

Xu, Jin,Green, Anthony P.,Turner, Nicholas J.

, p. 16760 - 16763 (2018)

Herein we report the biocatalytic synthe...

Characterization of volatile compounds from the reaction of 3-hydroxy- 2-butanone and ammonium sulfide model system

Xi, Junwu,Huang, Tzou-Chi,Ho, Chi-Tang

, p. 245 - 248 (1999)

The reactions between 3-hydroxy-2-butano...

Novel Ligustrazine-Based Analogs of Piperlongumine Potently Suppress Proliferation and Metastasis of Colorectal Cancer Cells in Vitro and in Vivo

Zou, Yu,Zhao, Di,Yan, Chang,Ji, Yanpeng,Liu, Jin,Xu, Jinyi,Lai, Yisheng,Tian, Jide,Zhang, Yihua,Huang, Zhangjian

, p. 1821 - 1832 (2018)

Piperlongumine 1 increases reactive oxyg...

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

Daw, Prosenjit,Ben-David, Yehoshoa,Milstein, David

supporting information, p. 11931 - 11934 (2018/09/27)

The synthesis of N-heteroaromatic compou...

A four-methyl pyrazine preparation method (by machine translation)

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Paragraph 0021; 0027; 0028; 0029; 0030; 0031; 0032, (2017/07/01)

The invention relates to a medicine inte...

1124-11-4 Process route

2-<2-Hydroxy-2-<p-(dimethylamino)phenyl>ethyl>-3,5,6-trimethylpyrazine
72725-76-9

2-<2-Hydroxy-2-ethyl>-3,5,6-trimethylpyrazine

Tetramethylpyrazine
1124-11-4

Tetramethylpyrazine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
Conditions Yield
In various solvent(s); at 171.5 ℃; Kinetics; in diglyme-d14; isotopic effect;
LysAla*hydrobromide
410538-35-1

LysAla*hydrobromide

2-oxopropanal
78-98-8

2-oxopropanal

2-Methylpyrazine
109-08-0

2-Methylpyrazine

2,5-dimethyl-pyrazine
123-32-0

2,5-dimethyl-pyrazine

2,3-dimethylpyrazine
5910-89-4

2,3-dimethylpyrazine

Tetramethylpyrazine
1124-11-4

Tetramethylpyrazine

2-ethyl-3,6-dimethylpyrazine
13360-65-1

2-ethyl-3,6-dimethylpyrazine

2,6-dimethylpyrazine
108-50-9

2,6-dimethylpyrazine

2,3,5-trimethylpyrazine
14667-55-1

2,3,5-trimethylpyrazine

3-ethenyl-2,5-dimethylpyrazine
80935-98-4

3-ethenyl-2,5-dimethylpyrazine

2-ethyl-3,5-dimethylpyrazine
13925-07-0

2-ethyl-3,5-dimethylpyrazine

5-ethyl-2,3-dimethylpyrazine
15707-34-3

5-ethyl-2,3-dimethylpyrazine

Conditions
Conditions Yield
In water; at 130 ℃; for 2h; pH=8;

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