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Tetramethylpyrazine

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Tetramethylpyrazine
Names
Preferred IUPAC name Tetramethylpyrazine
Other names Ligustrazine; Tetrapyrazine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.084 Edit this at Wikidata
EC Number
  • 214-391-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3Key: FINHMKGKINIASC-UHFFFAOYSA-N
  • InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3Key: FINHMKGKINIASC-UHFFFAOYSA-N
SMILES
  • CC1=C(N=C(C(=N1)C)C)C
Properties
Chemical formula C8H12N2
Molar mass 136.198 g·mol
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 , 100 kPa). Infobox references
Chemical compound

Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans. In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter. When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate. It exhibits potential nootropic and antiinflammatory activities in rats.

References

  1. Hashim, Puziah; Selamat, Jinap; Syed Muhammad, Sharifah Kharidah; Ali, Asbi (1998). "Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation". Journal of the Science of Food and Agriculture. 78 (4): 543–550. Bibcode:1998JSFA...78..543H. 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. Kosuge, Takuo; Adachi, Tahei; Kamiya, Hiroko (1962). "Isolation of Tetramethylpyrazine from Culture of Bacillus natto, and Biosynthetic Pathways of Tetramethylpyrazine". Nature. 195 (4846): 1103. Bibcode:1962Natur.195.1103K. doi:10.1038/1951103a0. PMID 14458746.
  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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