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| Names | |
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Preferred IUPAC name
Tetramethylpyrazine | |
| Other names
Ligustrazine; Tetrapyrazine
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| Identifiers | |
3D model (
JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.013.084 |
| EC Number |
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PubChem
CID
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| UNII | |
CompTox Dashboard (
EPA)
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| Properties | |
| C8H12N2 | |
| Molar mass | 136.198 g·mol−1 |
| Melting point | 84–86 °C (183–187 °F; 357–359 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans. [1] In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter. [2] When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate. [3] It exhibits potential nootropic and antiinflammatory activities in rats. [4] [5]
References
- ^ Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550. doi: 10.1002/(SICI)1097-0010(199812)78:4<543::AID-JSFA152>3.0.CO;2-2
- ^ Landis, Elizabeth A.; Oliverio, Angela M (January 26, 2021). "The diversity and function of sourdough starter microbiomes". eLife. 10: e61644. doi: 10.7554/eLife.61644. PMC 7837699. PMID 33496265.
- ^ Takuo Kosuge, Tahei Adachi & Hiroko Kamiya "Isolation Of Tetramethylpyrazine From Culture Of Bacillus Natto, And Biosynthetic Pathways Of Tetramethylpyrazine" Nature 1962, volume 195, 1103 . doi: 10.1038/1951103a0
- ^ Wu, W; Yu, X; Luo, XP; Yang, SH; Zheng, D (2013). "Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway". Behavioural Brain Research. 253: 212–6. doi: 10.1016/j.bbr.2013.07.052. PMID 23916742. S2CID 9100537.
- ^ Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ (2013). "Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats". Experimental Neurology. 247: 188–201. doi: 10.1016/j.expneurol.2013.04.010. PMID 23644042. S2CID 20967364.
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