Tetramethylpyrazine

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Tetramethylpyrazine
Tetramethylpyrazine.svg
Names
IUPAC name
2,3,5,6-Tetramethylpyrazine
Other names
Ligustrazine; Tetrapyrazine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.084
EC Number 214-391-2
UNII
Properties
C8H12N2
Molar mass 136.20 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).
Infobox references

Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in natto and in fermented cocoa beans.[1] When purified, tetramethylpyrazine is a colorless solid. It is classifed as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate.[2] It exhibits potential nootropic and antiinflammatory activities in rats.[3][4]

References[edit]

  1. ^ 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
  2. ^ 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
  3. ^ 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. 
  4. ^ 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.