四甲基吡嗪

四甲基吡嗪(英語:tetramethylpyrazine),又称为川芎嗪ligustrazinechuanxiongzine),是一种发现于纳豆和发酵可可豆的化学物质[1]。纯化后为无色固体,属于烷基吡嗪。一项研究表明,四甲基吡嗪是酸酵头中主要挥发性有机物[2]。四甲基吡嗪的生物合成涉及源自丙酮酸3-羟基丁酮的胺化过程[3]。在小鼠研究中,四甲基吡嗪展示出益智药特性和消炎活性[4][5]

四甲基吡嗪
IUPAC名
Tetramethylpyrazine
四甲基吡嗪
别名 2,3,5,6-四甲基吡嗪、川芎嗪
识别
CAS号 1124-11-4
PubChem 14296
ChemSpider 13658
SMILES
 
  • CC1=C(N=C(C(=N1)C)C)C
InChI
 
  • 1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChIKey FINHMKGKINIASC-UHFFFAOYSA-N
EINECS 214-391-2
ChEBI 133246
性质
化学式 C8H12N2
摩尔质量 136.19 g·mol−1
熔点 84-86 °C(271 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

川芎嗪名字来自北京制药工业研究所1972-1977年期间在川穹提取的生物碱中分离得到[6]

参考文献

  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. The diversity and function of sourdough starter microbiomes. eLife. January 26, 2021, 10: e61644. PMC 7837699 . PMID 33496265. doi:10.7554/eLife.61644 . 
  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. Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behavioural Brain Research. 2013, 253: 212–6. PMID 23916742. S2CID 9100537. doi:10.1016/j.bbr.2013.07.052. 
  5. ^ Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ. Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Experimental Neurology. 2013, 247: 188–201. PMID 23644042. S2CID 20967364. doi:10.1016/j.expneurol.2013.04.010. 
  6. ^ 川芎嗪的实验研究与临床观察. 新医药学杂志. 1977, (04): 45.