| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:11:52 UTC |
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| Update date | 2019-11-26 03:11:42 UTC |
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| Primary ID | FDB015495 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Tetramethylpyrazine |
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| Description | Tetramethylpyrazine, also known as TMP or liqustrazine, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Tetramethylpyrazine is a burnt, chocolate, and cocoa tasting compound. Tetramethylpyrazine has been detected, but not quantified in, several different foods, such as soy beans (Glycine max), cocoa and cocoa products, coconuts (Cocos nucifera), yellow bell peppers (Capsicum annuum), and potatos (Solanum tuberosum). This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Tetramethylpyrazine. |
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| CAS Number | 1124-11-4 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 2,3,5,6,-Tetramethyl-1,4-pyrazine | ChEBI | | 2,3,5,6-Tetramethylpyrazine | ChEBI | | FEMA 3237 | ChEBI | | FEMA no. 3237 | ChEBI | | Liqustrazine | ChEBI | | TMP | ChEBI | | TMPZ | MeSH | | Chuanxiongzine | MeSH | | Ligustrazine | MeSH | | Tetramethyl pyrazine | MeSH | | Tetramethylpyrazine hydrochloride | MeSH | | 2356-Tetramethyl-pyrazine | ChEMBL, HMDB | | 2356-Tetramethylpyrazine | ChEMBL, HMDB | | Ligustizine | HMDB | | Tetramethylpyrazin | HMDB | | Tetrapyrazine | HMDB | | TMP? | HMDB |
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| Predicted Properties | |
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| Chemical Formula | C8H12N2 |
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| IUPAC name | tetramethylpyrazine |
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| InChI Identifier | InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 |
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| InChI Key | FINHMKGKINIASC-UHFFFAOYSA-N |
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| Isomeric SMILES | CC1=NC(C)=C(C)N=C1C |
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| Average Molecular Weight | 136.1943 |
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| Monoisotopic Molecular Weight | 136.100048394 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Diazines |
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| Sub Class | Pyrazines |
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| Direct Parent | Pyrazines |
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| Alternative Parents | |
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| Substituents | - Pyrazine
- Heteroaromatic compound
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Industrial application: Biological role: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 70.55%; H 8.88%; N 20.57% | DFC |
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| Melting Point | Mp 86° (anhyd.) | DFC |
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| Boiling Point | Bp 190° | DFC |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | 1.28 | YAMAGAMI,C ET AL. (1991) |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | [neutral] lmax 294 (e 8500) (MeOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| EI-MS | Mass Spectrum (Electron Ionization) | splash10-0udr-9300000000-33fe7599448be6d9a1f0 | 2015-03-01 | View Spectrum | | GC-MS | Tetramethylpyrazine, non-derivatized, GC-MS Spectrum | splash10-0udu-9300000000-5d317f2dc804e043f2b9 | Spectrum | | GC-MS | Tetramethylpyrazine, non-derivatized, GC-MS Spectrum | splash10-0udu-9300000000-5d317f2dc804e043f2b9 | Spectrum | | Predicted GC-MS | Tetramethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-3900000000-68c7df3c47d48f17b27b | Spectrum | | Predicted GC-MS | Tetramethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, positive | splash10-000i-2900000000-825affe0aeefbf7abe2a | 2020-07-22 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-052r-9800000000-0e691fbfc32545d1b1aa | 2020-07-22 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, positive | splash10-0a4r-9300000000-bd32b31ff50928daf261 | 2020-07-22 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, positive | splash10-0pb9-9100000000-80bdd2f5e9e721213dba | 2020-07-22 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, positive | splash10-0ue9-9000000000-a8ff866cfac430f29e97 | 2020-07-22 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - n/a 9V, positive | splash10-0002-9000000000-acc42c048c36b7492ded | 2020-07-22 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - n/a 9V, positive | splash10-0a4i-9000000000-e10afcdf21ddde828d7c | 2020-07-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-4ea5d7454e8109b365d1 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-f797c5b258bf45ed5801 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udl-9100000000-465d4f375262ee01acb3 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-ca8b41e13886eb5f390f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-9c6dd6eec8dafc56f825 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kr-4900000000-a04f3b4c94a247e99232 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-ac299646e14f1770c4b5 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-3900000000-997da2b6ee4b7359f4d6 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9000000000-38545d1df73cc3f6ffdc | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-1900000000-22a6232d9fbf0c94bc77 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000l-9800000000-d3294b56735618c40d87 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9100000000-63057d96e8a5e3139795 | 2021-09-25 | View Spectrum |
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| NMR | | Type | Description | | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
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| External Links |
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| ChemSpider ID | 13658 |
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| ChEMBL ID | CHEMBL303697 |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 14296 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB36584 |
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| CRC / DFC (Dictionary of Food Compounds) ID | KCT72-F:KCT72-F |
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| EAFUS ID | 3647 |
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| Dr. Duke ID | TETRAMETHYL-PYRAZINE|LIGUSTRAZINE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | rw1009291 |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| Anti-aggregant | | An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots. | DUKE | | Anti anginal | 52217 | An agent that reduces angina symptoms by improving blood flow to the heart, commonly used in managing angina pectoris, coronary artery disease, and other cardiovascular conditions, to alleviate chest pain and prevent cardiac complications. | DUKE | | Anti-asthmatic | 49167 | An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health. | DUKE | | Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | | Anti cholinergic | 38323 | An agent that blocks the action of acetylcholine, a neurotransmitter, reducing muscle contractions and secretions. Therapeutically, it's used to treat conditions like overactive bladder, gastrointestinal disorders, and respiratory issues, as well as to manage symptoms of Parkinson's disease and motion sickness. | DUKE | | Anti dysmenorrheic | 52217 | An agent that alleviates menstrual cramp symptoms, reducing prostaglandin-induced uterine contractions. Therapeutically, it provides relief from dysmenorrhea, commonly used in managing primary dysmenorrhea and other menstrual disorders. | DUKE | | Anti embolic | | An agent that prevents or dissolves blood clots, used to treat or prevent thrombosis, embolism, and stroke, promoting blood flow and reducing risk of cardiovascular events. | DUKE | | Anti histaminic | 37956 | An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis. | DUKE | | Anti hypertensive | 52217 | An agent that lowers blood pressure, reducing the risk of cardiovascular disease. It plays a biological role in relaxing blood vessels, decreasing cardiac workload, and improving blood flow. Therapeutically, it's used to manage hypertension, heart failure, and stroke, with key medical applications in preventing organ damage and improving overall cardiovascular health. | DUKE | | Anti-ischemic | 52217 | An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload. | DUKE | | Anti metastatic | 35610 | An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer. | DUKE | | Anti-spasmodic | 52217 | An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort. | DUKE | | Anti thrombotic | 50248 | An agent that prevents blood clot formation, reducing the risk of thrombosis. Its biological role is to inhibit platelet aggregation and blood coagulation. Therapeutically, it is used to prevent and treat conditions such as stroke, heart attack, and deep vein thrombosis, as well as to manage atrial fibrillation and peripheral artery disease. | DUKE | | Arteriodilator | | An agent that dilates arteries, increasing blood flow to or from the heart, used therapeutically to manage conditions like hypertension, heart failure, and angina, improving cardiac output and reducing blood pressure. | DUKE | | Calcium antagonist | 48706 | A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases. | DUKE | | Cardiac | 38070 | Relating to the heart, referring to agents or functions that support heart health, treat cardiovascular diseases, or regulate heart rhythm, commonly used in managing conditions such as arrhythmias, heart failure, and hypertension. | DUKE | | Cardiotonic | 38070 | An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure. | DUKE | | Diuretic | 35498 | An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure. | DUKE | | Hypotensive | | An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications. | DUKE | | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | | Schistosomicide | | An agent destructive to schistosomes, used to treat schistosomiasis, a disease caused by blood flukes transmitted by snails. Therapeutically, it eliminates the parasites, reducing inflammation and preventing long-term damage. Key medical uses include treating and preventing schistosomiasis in endemic regions, particularly in Africa, Brazil, and Asia. | DUKE | | Uteros sedative | 52217 | An agent that relaxes the uterus, reducing spasms and contractions. Therapeutically, it alleviates menstrual cramps, premenstrual syndrome, and threatened abortion symptoms, commonly used in obstetrics and gynecology to promote uterine relaxation and prevent premature labor. | DUKE | | Vasodilator | 35620 | An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | | Flavor | Citations |
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| musty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | nutty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | chocolate |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | coffee |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | cocoa |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | soybean |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | lard |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | burnt |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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