Tetramethylpyrazine

Tetramethylpyrazine
Names
	Preferred IUPAC name Tetramethylpyrazine
	Other names Ligustrazine; Tetrapyrazine
Identifiers
CAS Number	1124-11-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:133246;
ChemSpider	13658;
ECHA InfoCard	100.013.084
EC Number	214-391-2;
PubChem CID	14296;
UNII	V80F4IA5XG ;
CompTox Dashboard (EPA)	DTXSID6047070 ;
	InChI 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;
	SMILES CC1=C(N=C(C(=N1)C)C)C;
Properties
Chemical formula	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

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

^ 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.
^ 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.
^ 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.
^ 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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