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Tetramethylpyrazine

From Wikipedia, the free encyclopedia
Tetramethylpyrazine
Names
Preferred IUPAC name
Tetramethylpyrazine
Other names
Ligustrazine; Tetrapyrazine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.013.084Edit this at Wikidata
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 mass136.198 g·mol−1
Melting point84–86 °C (183–187 °F; 357–359 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Tetramethylpyrazine, also known asligustrazine, is achemical compound found innattō and in fermentedcocoa beans.[1] In an observational study, tetramethylpyrazine was the dominantvolatile organic compound in onesourdough starter.[2] When purified, tetramethylpyrazine is a colorless solid. It is classified as analkylpyrazine. Its biosynthesis involves amination ofacetoin, the latter derived frompyruvate.[3] It exhibits potentialnootropic and antiinflammatory activities in rats.[4][5]

References

[edit]
  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.
Cocoa bean
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