Record Information |
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Version | 2.0 |
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Created at | 2012-09-11 17:45:55 UTC |
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Updated at | 2021-08-19 23:59:08 UTC |
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NP-MRD ID | NP0001446 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Trimethylpyrazine |
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Description | Trimethylpyrazine, also known as fema 3244, 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. Trimethylpyrazine is a cocoa, earthy, and hazelnut tasting compound. Trimethylpyrazine is found, on average, in the highest concentration in kohlrabis. Trimethylpyrazine has also been detected, but not quantified, in several different foods, such as green vegetables, pepper (c. Annuum), orange bell peppers, potato, and red bell peppers. This could make trimethylpyrazine a potential biomarker for the consumption of these foods. Found in many foodstuffs e.G. Asparagus, baked potato, wheat bread, Swiss cheese, coffee, black tea, roasted filbert and peanut, and soybean. |
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Structure | [H]C1=C(N=C(C(=N1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3 |
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Synonyms | Value | Source |
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235-Trimethyl-pyrazine | HMDB | 2,3,5-TRIMETHYL pyrazine | HMDB | 2,3,5-Trimethyl-pyrazine | HMDB | 2,3,6-Trimethylpyrazine | HMDB | FEMA 3244 | HMDB | Pyrazine, 2,3,5-trimethyl | HMDB | Trimethyl-pyrazine | HMDB |
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Chemical Formula | C7H10N2 |
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Average Mass | 122.1677 Da |
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Monoisotopic Mass | 122.08440 Da |
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IUPAC Name | 2,3,5-trimethylpyrazine |
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Traditional Name | pyrazine, trimethyl- |
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CAS Registry Number | 14667-55-1 |
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SMILES | [H]C1=C(N=C(C(=N1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3 |
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InChI Key | IAEGWXHKWJGQAZ-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Van Lancker F, Adams A, De Kimpe N: Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems. J Agric Food Chem. 2012 May 9;60(18):4697-708. doi: 10.1021/jf301315b. Epub 2012 Apr 25. [PubMed:22463717 ]
- Bohman B, Jeffares L, Flematti G, Byrne LT, Skelton BW, Phillips RD, Dixon KW, Peakall R, Barrow RA: Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid. J Nat Prod. 2012 Sep 28;75(9):1589-94. Epub 2012 Sep 18. [PubMed:22988937 ]
- Zhai L, Zhang P, Sun RY, Liu XY, Liu WG, Guo XL: Cytoprotective effects of CSTMP, a novel stilbene derivative, against H2O2-induced oxidative stress in human endothelial cells. Pharmacol Rep. 2011;63(6):1469-80. [PubMed:22358095 ]
- Li S, Chen H, Wang X, Wu J, Jiang J, Wang Y: Pharmacokinetic study of a novel stroke therapeutic, 2-[[(1,1-dimethylethyl)oxidoimino]methyl]-3,5,6-trimethylpyrazine, by a simple HPLC-UV method in rats. Eur J Drug Metab Pharmacokinet. 2011 Jun;36(2):95-101. doi: 10.1007/s13318-011-0032-2. Epub 2011 Mar 22. [PubMed:21424683 ]
- Divine RD, Sommer D, Lopez-Hernandez A, Rankin SA: Short communication: Evidence for methylglyoxal-mediated browning of Parmesan cheese during low temperature storage. J Dairy Sci. 2012 May;95(5):2347-54. doi: 10.3168/jds.2011-4828. [PubMed:22541463 ]
- Yang XZ, Yang WH, Xu YG, Diao XJ, He GW, Gong GQ: Synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing a cleavable moiety with anti-platelet activity. Eur J Med Chem. 2012 Nov;57:21-8. doi: 10.1016/j.ejmech.2012.09.016. Epub 2012 Sep 18. [PubMed:23043765 ]
- Ren M, Dong J, Xu Y, Wen N, Gong G: Synthesis of novel ligustrazine derivatives as NA+/H+ exchange inhibitors. Chem Biodivers. 2010 Nov;7(11):2727-36. doi: 10.1002/cbdv.200900353. [PubMed:21072772 ]
- Huang Y, Barringer SA: Alkylpyrazines and other volatiles in cocoa liquors at pH 5 to 8, by Selected Ion Flow Tube-Mass Spectrometry (SIFT-MS). J Food Sci. 2010 Jan-Feb;75(1):C121-7. doi: 10.1111/j.1750-3841.2009.01455.x. [PubMed:20492142 ]
- Magi E, Bono L, Di Carro M: Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols. J Mass Spectrom. 2012 Sep;47(9):1191-7. doi: 10.1002/jms.3034. [PubMed:22972787 ]
- Qin P, Ma T, Wu L, Shan F, Ren G: Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry. J Food Sci. 2011 Aug;76(6):S401-7. doi: 10.1111/j.1750-3841.2011.02223.x. Epub 2011 Jun 8. [PubMed:22417522 ]
- Huang Y, Barringer SA: Monitoring of cocoa volatiles produced during roasting by selected ion flow tube-mass spectrometry (SIFT-MS). J Food Sci. 2011 Mar;76(2):C279-86. doi: 10.1111/j.1750-3841.2010.01984.x. Epub 2011 Feb 1. [PubMed:21535747 ]
- Sun Y, Yu P, Zhang G, Wang L, Zhong H, Zhai Z, Wang L, Wang Y: Therapeutic effects of tetramethylpyrazine nitrone in rat ischemic stroke models. J Neurosci Res. 2012 Aug;90(8):1662-9. doi: 10.1002/jnr.23034. Epub 2012 Mar 19. [PubMed:22431378 ]
- Sharp MD, Kocaoglu-Vurma NA, Langford V, Rodriguez-Saona LE, Harper WJ: Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry. J Food Sci. 2012 Mar;77(3):C284-92. doi: 10.1111/j.1750-3841.2011.02544.x. [PubMed:22384952 ]
- Guerra PV, Yaylayan VA: Double Schiff base adducts of 2,3-butanedione with glycine: formation of pyrazine rings with the participation of amino acid carbon atoms. J Agric Food Chem. 2012 Nov 14;60(45):11440-5. doi: 10.1021/jf303658m. Epub 2012 Nov 6. [PubMed:23106172 ]
- Ishida T, Takechi S, Yamaguchi T: Possible involvement of glutathione balance disruption in dihydropyrazine-induced cytotoxicity on human hepatoma HepG2 cells. J Toxicol Sci. 2012;37(5):1065-9. [PubMed:23038014 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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