Tetramethylpyrazine

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]

Tetramethylpyrazine
Names
Preferred IUPAC name
Tetramethylpyrazine
Other names
Ligustrazine; Tetrapyrazine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.084
EC Number
  • 214-391-2
UNII
  • InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
    Key: FINHMKGKINIASC-UHFFFAOYSA-N
  • InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
    Key: FINHMKGKINIASC-UHFFFAOYSA-N
  • CC1=C(N=C(C(=N1)C)C)C
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).
Infobox references

References
  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. 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.
  3. 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
  4. 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.
  5. 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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