2,3,5,6-Tetramethylpyrazine

Base Information

• Chemical Name: 2,3,5,6-Tetramethylpyrazine
• CAS No.: 1124-11-4
• Deprecated CAS: 87396-75-6,93615-56-6,93615-56-6
• Molecular Formula: C8H12N2
• Molecular Weight: 136.197
• Hs Code.: 29339990
• European Community (EC) Number: 214-391-2
• NSC Number: 46451,36080
• UNII: V80F4IA5XG
• DSSTox Substance ID: DTXSID6047070
• Nikkaji Number: J39.647H
• Wikipedia: Tetramethylpyrazine
• Wikidata: Q11319317
• Metabolomics Workbench ID: 47401
• ChEMBL ID: CHEMBL303697
• Mol file: 1124-11-4.mol

Synonyms:chuanxiongzine;ligustrazine;Liqustrazine;tetramethyl pyrazine;tetramethylpyrazine;tetramethylpyrazine hydrochloride;TMPZ

Chemical Property of 2,3,5,6-Tetramethylpyrazine

Chemical Property:

• 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
• Storage Temp.: Store below +30°C.
• Solubility.: 4g/l
• Water Solubility.: Soluble in water (4 g/L at 20°C).
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 136.100048391
• Heavy Atom Count: 10
• Complexity: 87.8

Purity/Quality:

99% ^*data from raw suppliers

Tetramethylpyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-39-24/25-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(C(=N1)C)C)C
• General Description: Tetramethylpyrazine (also known as Ligustrazine) is a bioactive compound derived from traditional Chinese medicine, recognized for its cerebrocardiac vascular benefits but limited by poor bioavailability and short half-life. Structural modifications, such as conjugation with piperazine and pharmacophores like bisphenylmethyl, have yielded derivatives with enhanced cell-protective and antiplatelet aggregation properties, surpassing the efficacy of the parent compound. Notably, derivatives like **7a** and **7c** demonstrate superior activity, suggesting promising therapeutic potential for cerebrocardiac vascular diseases, warranting further preclinical investigation.

Technology Process of 2,3,5,6-Tetramethylpyrazine

There total 65 articles about 2,3,5,6-Tetramethylpyrazine 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: 73.9%

4-Chloro-3-methylphenol (59-50-7) → 2,4-dichloro-3-methylphenol (17788-00-0) + 4,6-dichloro-3-methylphenol (1124-07-8)

Guidance literature:

With chloroamine; In water; pH=9.0; Further Variations:; Reagents; pH-values; Product distribution;

DOI:10.1021/es030644h

Reference yield: 59.6%

2-chloro-5-methylphenol (615-74-7) → 3-methyl-2,6-dichlorophenol (13481-70-4) + 4,6-dichloro-3-methylphenol (1124-07-8)

Guidance literature:

With chloroamine; In water; pH=9.0; Further Variations:; Reagents; pH-values; Product distribution;

DOI:10.1021/es030644h

Reference yield:

2-<2-Hydroxy-2-ethyl>-3,5,6-trimethylpyrazine (72725-76-9) → Tetramethylpyrazine (1124-11-4) + 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

In various solvent(s); at 171.5 ℃; Kinetics; in diglyme-d14; isotopic effect;

DOI:10.1021/jo01294a016

upstream raw materials:

pyridine

L-Aspartic acid

acetic anhydride

2-acetamido-3-butanone

Downstream raw materials:

2,3,5,6-tetramethylpyrazine mono N-oxide

2,3,5,6-tetramethylpyrazine-N,N'-dioxide

pyrazine-2,3,5,6-tetracarboxylic acid

2-(3-pentenyl)-3,5,6-trimethylpyrazine

Refernces

Design, synthesis, and biological activities of novel Ligustrazine derivatives

10.1016/j.bmc.2007.03.033

This research aimed to develop new cerebrocardiac vascular drugs by modifying the structure of Ligustrazine, a traditional Chinese medicine component with low bioavailability and short half-life. The researchers designed and synthesized a series of Ligustrazine derivatives by combining it with a piperazine and various pharmacophores or drug-like groups, such as substituted benzyl, cinnamyl, bisphenylmethyl, and ligustrazinyl. The synthesized derivatives were evaluated for their protective effects on hydrogen peroxide-damaged ECV-304 cells and antiplatelet aggregation activities. The results showed that most derivatives exhibited lower EC50 values for cell protection and better antiplatelet aggregation activities compared to Ligustrazine. The derivatives containing the bisphenylmethyl pharmacophore (7a–c) were found to be the most potent, with compound 7a showing the best protective effects and compound 7c being the most active antiplatelet aggregation agent. The study concluded that these novel Ligustrazine derivatives have improved pharmacokinetic properties and potential therapeutic applications, with further animal model studies underway to explore their cerebrocardiac vascular activities.