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| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
|---|
Basic Description
| Synonyms | 2,3,5,6-Tetramethylpyrazine | TETRAMETHYLPYRAZINE | 1124-11-4 | Ligustrazine | Pyrazine, tetramethyl- | Bs factor | Tetrapyrazine | Tetramethylpyrazin | Chuanxiongzine | Liqustrazine | Ligustizine | 2,3,5,6-Tetramethyl pyrazine | chuanxingzine | FEMA No. 3237 | 2,3,5,6,-Tetramethyl- |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In | Ice chest + Ice pads |
| Product Description | 2,3,5,6-Tetramethylpyrazine is a flavor ingredient in tobacco that has bee used in the treatment of several disorders such as asthma, heart failure, rhinitis and urinary incontinence. |
Associated Targets(Human)
HDAC6 Tclin Histone deacetylase 6 (0 Activities)
TXNRD1 Tclin Thioredoxin reductase 1, cytoplasmic (0 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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ABCB11 Tchem Bile salt export pump (0 Activities)
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Homo sapiens (32628 Activities)
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ECV-304 (406 Activities)
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HT-29 (80576 Activities)
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K562 (73714 Activities)
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MCF7 (126967 Activities)
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SH-SY5Y (11521 Activities)
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U-87 MG (3946 Activities)
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A549 (127892 Activities)
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Bel-7402 (4577 Activities)
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HCT-116 (91556 Activities)
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HepG2 (196354 Activities)
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HUVEC (11049 Activities)
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HeLa (62764 Activities)
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MDA-MB-231 (73002 Activities)
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ABCB11 Tchem Bile salt export pump (2311 Activities)
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Associated Targets(non-human)
Hdac6 Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Rattus norvegicus (775804 Activities)
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PC-12 (7051 Activities)
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TRXR Thioredoxin reductase (20 Activities)
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rep Replicase polyprotein 1ab (378 Activities)
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Plasma (328 Activities)
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Thoracic aorta (838 Activities)
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SARS-CoV-2 (38078 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | 2,3,5,6-tetramethylpyrazine |
|---|---|
| INCHI | InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 |
| InChi Key | FINHMKGKINIASC-UHFFFAOYSA-N |
| Canonical SMILES | CC1=C(N=C(C(=N1)C)C)C |
| Isomeric SMILES | CC1=C(N=C(C(=N1)C)C)C |
| WGK Germany | 3 |
| RTECS | UQ3905000 |
| PubChem CID | 14296 |
| Molecular Weight | 136.19 |
| Beilstein | 113100 |
| Reaxy-Rn | 113100 |
Certificates
Certificate of Analysis(COA)
Enter Lot Number to search for COA:
Chemical and Physical Properties
| Boil Point(°C) | 190°C |
|---|---|
| Melt Point(°C) | 82-86°C |
Safety and Hazards(GHS)
| Pictogram(s) | GHS07 |
|---|---|
| Signal | Warning |
| Hazard Statements | H302:Harmful if swallowed |
| Precautionary Statements | P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. P301+P317:IF SWALLOWED: Get medical help. |
| WGK Germany | 3 |
| RTECS | UQ3905000 |
| Reaxy-Rn | 113100 |
Related Documents
Citations of This Product
| 1. Yue Luo, Siyue Zhu, Jie Peng, Heping Cui, Qingrong Huang, Baojun Xu, Chi-Tang Ho. (2023) Feasibility Study of Amadori Rearrangement Products of Glycine, Diglycine, Triglycine, and Glucose as Potential Food Additives for Production, Stability, and Flavor Formation. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:38109376] [10.1021/acs.jafc.3c06250] |
| 2. Hong Yang, Jing Wang, Wenming Cao. (2023) Improved liquid-liquid extraction followed by HPLC-UV for accurate and eco-friendly determination of tetramethylpyrazine in vinegar products. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1229 (123869). [PMID:37716345] [10.1016/j.jchromb.2023.123869] |
| 3. Li Chen, Qingshun Nian, Digen Ruan, Jiajia Fan, Yecheng Li, Shunqiang Chen, Lijiang Tan, Xuan Luo, Zhuangzhuang Cui, Yifeng Cheng, Changhao Li, Xiaodi Ren. (2023) High-safety and high-efficiency electrolyte design for 4.6 V-class lithium-ion batteries with a non-solvating flame-retardant. Chemical Science, 14 (5): (1184-1193). [PMID:36756331] [10.1039/D2SC05723A] |
| 4. Tong Zhou, Xue Xia, Heping Cui, Khizar Hayat, Xiaoming Zhang, Chi-Tang Ho. (2022) Competitive Formation of 2,3-Butanedione and Pyrazines through Intervention of Added Cysteine during Thermal Processing of Alanine-Xylose Amadori Compounds. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 70 (48): (15202–15212). [PMID:36444759] [10.1021/acs.jafc.2c07026] |
| 5. Shibin Deng, Yun Zhai, Heping Cui, Khizar Hayat, Xiaoming Zhang, Chi-Tang Ho. (2022) Mechanism of Pyrazine Formation Intervened by Oxidized Methionines during Thermal Degradation of the Methionine–Glucose Amadori Compound. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 70 (45): (14457–14467). [PMID:36342227] [10.1021/acs.jafc.2c06458] |
| 6. Ren Yanling, Wang Tao, Jiang Yingjie, Chen Pengchao, Tang Jian, Wang Juan, Jin Daochao, Guo Jianjun. (2022) Research of Synergistic Substances on Tobacco Beetle [Lasioderma serricorne (Fabricius) (Coleoptera: Anobiidae)] Adults Attractants. Frontiers in Chemistry, 10 [PMID:35755262] [10.3389/fchem.2022.921113] |
| 7. Jian-Li Qiu, Guo-Feng Zhang, Yu-Na Chai, Xiao-Yan Han, Hai-Tao Zheng, Xiang-Feng Li, Fei Duan, Ling-Yan Chen. (2022) Ligustrazine Attenuates Liver Fibrosis by Targeting miR-145 Mediated Transforming Growth Factor-β/Smad Signaling in an Animal Model of Biliary Atresia. JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 381 (3): (257-265). [PMID:35398813] [10.1124/jpet.121.001020] |
| 8. Tao Tian, Guo-Ying Chen, Hao Zhang, Feng-Qing Yang. (2021) Personal Glucose Meter for α-Glucosidase Inhibitor Screening Based on the Hydrolysis of Maltose. MOLECULES, 26 (15): (4638). [PMID:34361791] [10.3390/molecules26154638] |
| 9. Hanjun Zhang, Furong Tao, Yuezhi Cui, Hongtao Wu. (2020) Super-quenching: Multiple migration channels of excitons cause “area quenching”. MATERIALS CHEMISTRY AND PHYSICS, 243 (122657). [PMID:] [10.1016/j.matchemphys.2020.122657] |
| 10. Zhou Wei, Chen Ziyi, Zhang Guohao, Liu Zhigang. (2019) Systems pharmacology-based approach for dissecting the mechanisms of pyrazine components in Maotai liquor. BIOSCIENCE REPORTS, 39 (10): [PMID:31511433] [10.1042/BSR20191864] |
| 11. Hui Wang, Wenxi Zhang, Yatao Cheng, Xinyu Zhang, Nannan Xue, Gaorong Wu, Meng Chen, Kang Fang, Wenbo Guo, Fei Zhou, Herong Cui, Tao Ma, Penglong Wang, Haimin Lei. (2018) Design, Synthesis and Biological Evaluation of Ligustrazine-Flavonoid Derivatives as Potential Anti-Tumor Agents. MOLECULES, 23 (9): (2187). [PMID:30200208] [10.3390/molecules23092187] |
| 12. Chen Long, Liu Tianjun, Wang Qiangsong, Liu Juan. (2017) Anti-inflammatory effect of combined tetramethylpyrazine, resveratrol and curcumin in vivo. BMC Complementary and Alternative Medicine, 17 (1): (1-10). [PMID:28449676] [10.1186/s12906-017-1739-7] |
| 13. Qing Wang, Yao Long, Lin Yao, Li Xu, Zhi-Guo Shi, Lanying Xu. (2016) Preparation, characterization and application of a reversed phase liquid chromatography/hydrophilic interaction chromatography mixed-mode C18-DTT stationary phase. TALANTA, 146 (442). [PMID:26695288] [10.1016/j.talanta.2015.09.009] |
| 14. Zhang Xuemei, Wei Junhua, Ma Pengkai, Mu Hongjie, Wang Aiping, Zhang Leiming, Wu Zimei, Sun Kaoxiang. (2014) Preparation and evaluation of a novel biodegradable long-acting intravitreal implant containing ligustrazine for the treatment of proliferative vitreoretinopathy. JOURNAL OF PHARMACY AND PHARMACOLOGY, 67 (2): (160-169). [PMID:25557298] [10.1111/jphp.12327] |
References
| 1. Yue Luo, Siyue Zhu, Jie Peng, Heping Cui, Qingrong Huang, Baojun Xu, Chi-Tang Ho. (2023) Feasibility Study of Amadori Rearrangement Products of Glycine, Diglycine, Triglycine, and Glucose as Potential Food Additives for Production, Stability, and Flavor Formation. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:38109376] [10.1021/acs.jafc.3c06250] |
| 2. Hong Yang, Jing Wang, Wenming Cao. (2023) Improved liquid-liquid extraction followed by HPLC-UV for accurate and eco-friendly determination of tetramethylpyrazine in vinegar products. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1229 (123869). [PMID:37716345] [10.1016/j.jchromb.2023.123869] |
| 3. Li Chen, Qingshun Nian, Digen Ruan, Jiajia Fan, Yecheng Li, Shunqiang Chen, Lijiang Tan, Xuan Luo, Zhuangzhuang Cui, Yifeng Cheng, Changhao Li, Xiaodi Ren. (2023) High-safety and high-efficiency electrolyte design for 4.6 V-class lithium-ion batteries with a non-solvating flame-retardant. Chemical Science, 14 (5): (1184-1193). [PMID:36756331] [10.1039/D2SC05723A] |
| 4. Tong Zhou, Xue Xia, Heping Cui, Khizar Hayat, Xiaoming Zhang, Chi-Tang Ho. (2022) Competitive Formation of 2,3-Butanedione and Pyrazines through Intervention of Added Cysteine during Thermal Processing of Alanine-Xylose Amadori Compounds. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 70 (48): (15202–15212). [PMID:36444759] [10.1021/acs.jafc.2c07026] |
| 5. Shibin Deng, Yun Zhai, Heping Cui, Khizar Hayat, Xiaoming Zhang, Chi-Tang Ho. (2022) Mechanism of Pyrazine Formation Intervened by Oxidized Methionines during Thermal Degradation of the Methionine–Glucose Amadori Compound. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 70 (45): (14457–14467). [PMID:36342227] [10.1021/acs.jafc.2c06458] |
| 6. Ren Yanling, Wang Tao, Jiang Yingjie, Chen Pengchao, Tang Jian, Wang Juan, Jin Daochao, Guo Jianjun. (2022) Research of Synergistic Substances on Tobacco Beetle [Lasioderma serricorne (Fabricius) (Coleoptera: Anobiidae)] Adults Attractants. Frontiers in Chemistry, 10 [PMID:35755262] [10.3389/fchem.2022.921113] |
| 7. Jian-Li Qiu, Guo-Feng Zhang, Yu-Na Chai, Xiao-Yan Han, Hai-Tao Zheng, Xiang-Feng Li, Fei Duan, Ling-Yan Chen. (2022) Ligustrazine Attenuates Liver Fibrosis by Targeting miR-145 Mediated Transforming Growth Factor-β/Smad Signaling in an Animal Model of Biliary Atresia. JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 381 (3): (257-265). [PMID:35398813] [10.1124/jpet.121.001020] |
| 8. Tao Tian, Guo-Ying Chen, Hao Zhang, Feng-Qing Yang. (2021) Personal Glucose Meter for α-Glucosidase Inhibitor Screening Based on the Hydrolysis of Maltose. MOLECULES, 26 (15): (4638). [PMID:34361791] [10.3390/molecules26154638] |
| 9. Hanjun Zhang, Furong Tao, Yuezhi Cui, Hongtao Wu. (2020) Super-quenching: Multiple migration channels of excitons cause “area quenching”. MATERIALS CHEMISTRY AND PHYSICS, 243 (122657). [PMID:] [10.1016/j.matchemphys.2020.122657] |
| 10. Zhou Wei, Chen Ziyi, Zhang Guohao, Liu Zhigang. (2019) Systems pharmacology-based approach for dissecting the mechanisms of pyrazine components in Maotai liquor. BIOSCIENCE REPORTS, 39 (10): [PMID:31511433] [10.1042/BSR20191864] |
| 11. Hui Wang, Wenxi Zhang, Yatao Cheng, Xinyu Zhang, Nannan Xue, Gaorong Wu, Meng Chen, Kang Fang, Wenbo Guo, Fei Zhou, Herong Cui, Tao Ma, Penglong Wang, Haimin Lei. (2018) Design, Synthesis and Biological Evaluation of Ligustrazine-Flavonoid Derivatives as Potential Anti-Tumor Agents. MOLECULES, 23 (9): (2187). [PMID:30200208] [10.3390/molecules23092187] |
| 12. Chen Long, Liu Tianjun, Wang Qiangsong, Liu Juan. (2017) Anti-inflammatory effect of combined tetramethylpyrazine, resveratrol and curcumin in vivo. BMC Complementary and Alternative Medicine, 17 (1): (1-10). [PMID:28449676] [10.1186/s12906-017-1739-7] |
| 13. Qing Wang, Yao Long, Lin Yao, Li Xu, Zhi-Guo Shi, Lanying Xu. (2016) Preparation, characterization and application of a reversed phase liquid chromatography/hydrophilic interaction chromatography mixed-mode C18-DTT stationary phase. TALANTA, 146 (442). [PMID:26695288] [10.1016/j.talanta.2015.09.009] |
| 14. Zhang Xuemei, Wei Junhua, Ma Pengkai, Mu Hongjie, Wang Aiping, Zhang Leiming, Wu Zimei, Sun Kaoxiang. (2014) Preparation and evaluation of a novel biodegradable long-acting intravitreal implant containing ligustrazine for the treatment of proliferative vitreoretinopathy. JOURNAL OF PHARMACY AND PHARMACOLOGY, 67 (2): (160-169). [PMID:25557298] [10.1111/jphp.12327] |