Tetramethylpyrazine
tetramethylpyrazine
CAS: 1124-11-4
Molecular Formula: C8H12N2
Tetramethylpyrazine - Names and Identifiers
| Name | tetramethylpyrazine |
| Synonyms | FEMA 3237 BS Factor Ligustrazine TETRAPYRAZINE FEMA NUMBER 3237 Tetramethylpyrazin tetramethyl-pyrazin tetramethylpyrazine Pyrazine,tetramethyl- 2,3,5,6-Tetramethylpyrazine 2,3,5,6-Tetramethyl pyrazine |
| CAS | 1124-11-4 |
| EINECS | 214-391-2 |
| InChI | InChI=1/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 |
| InChIKey | FINHMKGKINIASC-UHFFFAOYSA-N |
Tetramethylpyrazine - Physico-chemical Properties
| Molecular Formula | C8H12N2 |
| Molar Mass | 136.19 |
| Density | 1.08 |
| Melting Point | 77-80°C(lit.) |
| Boling Point | 190°C(lit.) |
| Flash Point | 128-130°C/200mm |
| JECFA Number | 780 |
| Water Solubility | Soluble in water (4 g/L at 20°C). |
| Solubility | 4g/l |
| Vapor Presure | 0.671mmHg at 25°C |
| Appearance | Colorless needle crystal |
| Color | White to Off-White |
| BRN | 113100 |
| pKa | 3.20±0.10(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| Refractive Index | 1.5880 (estimate) |
| MDL | MFCD00006146 |
| Physical and Chemical Properties | density 1.08 melting point 82-86°C boiling point 190°C |
| Use | Used as flavoring agents, sweetness enhancers for alcoholic beverages, flavoring agents and supplements for cigarettes |
Tetramethylpyrazine - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | UQ3905000 |
| TSCA | Yes |
| HS Code | 29339990 |
Tetramethylpyrazine - Upstream Downstream Industry
| Raw Materials | Sodium nitrite |
Tetramethylpyrazine - Reference
| Reference Show more | 1. Li Dongjing, Li Xinyu, Yang Yang, et al. Study on Preparation Technology of Ligustrazine BCA-PLGA Nanoparticles. Journal of Harbin University of Commerce (Natural Science Edition). 2. Zhang Wenjun, Wang Qing, Zhang Guofeng, et al. Formulation Optimization of Ligustrazine Double-inclusive Nanoparticles and Study on Drug Release Behavior in Vitro [J]. New Chinese Medicine and Clinical Pharmacology, 2019, v.30;No.165(12):121-125. 3. Li Feng, Huang Cheng, Li Jun. Effect and mechanism of ligustrazine on apoptosis of hepatic stellate cells [J]. Journal of Anhui Medical University, 2017, 52(012):1773-1777. 4. Song Jingmei, Chen Simiao, Chen Bing, et al. Effects of Different Proportion of Ligusticum chuanxiong Sophora flavescens on Active Ingredients and Antioxidant Activity [J]. Chinese Medicine Emergency, 2020(1):87-90. 5. Zhong Guifang, Zhang Fan, Guo Huixiang, Zhou Yifei, Ma Geli, Wang Guanglu. Screening and Identification of Tetramethylpyrazine-producing Bacteria in High Temperature Daqu [J]. Brewing in China, 2020, v.39;No.342(08):111-115. 6. Li Dongjing, Li Xinyu, Yang Yang, Feng Guoli, Wang Zhichong, Zhang Wenjun. Study on Preparation Technology of Ligustrazine BCA-PLGA Nanoparticles [J]. Journal of Harbin University of Commerce (Natural Science Edition),2020,36(04):387-392. 7. Zhong Guifang, Zhang Fan, Guo Huixiang, Zhou Yifei, Ma Geli, Wang Guanglu. Screening and Identification of Tetramethylpyrazine Producing Bacteria in High Temperature Daqu [J]. Brewing in China, 2020,39(08):107-111. 8. Liu Mingzong, Liu Yusong, Long Guoli, Zhang Zhao, Jiang Yuhong, Gao Rongmao. Ligustrazine regulates miR-31-5p/Ednrb pathway and inhibits BEAS-2B apoptosis and inflammatory response in human alveolar epithelial cells [J]. Chinese patent medicine, 2021,43(03):617-624. 9. [IF = 3.038] Shao Zhengkai et al."Tetramethylpyrazine Protects Against Early Brain Injury and Inhibits the PERK/Akt Pathway in a Rat Model of Subarachnoid Hemorrhage." Neurochem Res. 2018 Aug;43(8):1650-1659 10. [IF = 1.984] Yuan Rong et al."Tetramethylpyrazine and Paeoniflorin Inhibit Oxidized LDL-Induced Angiogenesis in Human Umbilical Vein Endothelial Cells via VEGF and Notch Pathways." Evid-Based Compl Alt. 2018;2018:3082507 11. [IF = 5.875] Sirui Xiao et al."Increased microneedle-mediated transdermal delivery of tetramethylpyrazine to the brain, combined with borneol and iontophoresis, for MCAO prevention." Int J Pharmaceut. 2020 Feb;575:118962 12. [IF = 5.81] Jiang Yue-Peng et al."Inconsistent Time-Dependent Effects of Tetramethylpyrazine on Primary Neurological Disorders and Psychiatric Comorbidities." Front Pharmacol. 2021 Aug;0:1957 13. [IF = 2.629] Guan Baoyi et al."Antiplatelet Activity of Tetramethylpyrazine via Regulation of the P2Y12 Receptor Downstream Signaling Pathway." Evid-Based Compl Alt. 2022;2022:7941039 |
Tetramethylpyrazine - Reference Information
| FEMA | 3237 | 2,3,5,6-TETRAMETHYLPYRAZINE |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| traits | 2,3,5,6-tetramethylpyrazine is a colorless to pale yellow transparent liquid. |
| pharmacological action | ligustrazine is a bioactive ingredient extracted from the widely used traditional Chinese medicine chuanxiong. It can inhibit platelet aggregation, enhance vasodilation, increase cerebral blood flow, and has neuroprotective effect. Ligustrazine injection has been widely used in the treatment of ischemic stroke, coronary heart disease, diabetic nephropathy, and knee osteoarthritis in China. Ligustrazine has also been evaluated as a clinical treatment for pressure ulcers, as a salvage agent for patients with non-Hodgkin's lymphoma, and as a treatment for bronchial asthma and vertebrobasilar insufficiency. |
| guidelines for use | guidelines for in vivo use ligustrazine was used together with transdermal patches in a clinical trial for the treatment of pressure ulcers. For the treatment of bronchial asthma, ligustrazine is administered by inhalation. Treatment of vertebrobasilar artery insufficiency, intravenous drip of ligustrazine 80 mg, plus 5% glucose 250 ml or 0.9% normal saline for 15 days. route of administration: transdermal; nasal; intravenous injection guidelines for in vitro use antiplatelet activity of ligustrazine was determined in human platelet suspension. In human platelets, tetramethylpyrazine (0.5-1.5 mM) dose-dependently inhibited platelet aggregation and was determined by turbidimetry. |
| use | 2,3,5,6-tetramethylpyrazine is used in soft drinks and nut foods. GB 2760-1996: Edible spices allowed. Mainly used to prepare meat and cocoa, peanuts, nuts, coffee, chocolate and other flavors. Used in drug production. Used as flavoring agent, sweet flavor enhancer for alcoholic beverages, flavoring agent and tonic for cigarettes |
| Production method | Methylpyrazine is obtained from the condensation of butanone and ethyl nitrite to form diacetyl monooxime, which is then reduced and cyclized. The cyclization reaction product is subjected to steam distillation, and the distillate is cooled, crystallized, and filtered to obtain crude tetramethylpyrazine. Recrystallization with water and decolorization with activated carbon during refining. When preparing its hydrochloride, it can be added dropwise to acetone with ethanol solution containing 15%-20% hydrogen chloride to form a salt. It is formed by condensation of 2, 3-succinedione and 2, 3-succinedione. |
Last Update：2024-04-10 22:29:15
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Raw Materials for Tetramethylpyrazine