花椒毒酚

花椒毒酚是一種呋喃香豆素。它是蛇床的主要有效成分之一。[3]它可由花椒毒素三溴化硼脱甲基制得。[4]

花椒毒酚
Chemical structure of xanthotoxol.
IUPAC名
9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one
别名 8-Hydroxypsoralen
8-Hydroxypsoralene
8-Hydroxyfuranocoumarin
识别
CAS号 2009-24-7  checkY
PubChem 65090
ChemSpider 58600
SMILES
 
  • C1=CC(=O)OC2=C(C3=C(C=CO3)C=C21)O
InChI
 
  • 1/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H
InChIKey JWVYQQGERKEAHW-UHFFFAOYAF
性质
化学式 C11H6O4
202.16 g/mol g·mol¹
熔点 240 °C(513 K)[1]
245 °C(518 K)[2]
溶解性  
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

代謝

  • 花椒毒酚-O-甲基轉移酶(8-羥基呋喃香豆素-8-O-甲基轉移酶)是一種酶。它會使用S-腺苷甲硫氨酸和花椒毒酚來生產S-腺苷高半胱氨酸和O-甲基花椒毒酚(花椒毒素或或甲氧沙林)。

參考文獻

  1. M. M. Abou-Elzahab, M. A. Metwally, A. M. Dawidar, M. Abdel-Mogib, E. A. Abu-Mustafa. . Bulletin of the Chemical Society of Japan. 1987-12, 60 (12): 4433–4435 [2021-11-23]. ISSN 0009-2673. doi:10.1246/bcsj.60.4433. (原始内容存档于2021-11-23) (英语).
  2. Lokar, Laura R. Coassini; Delben, Sergio. Taxonomical studies on Sesali elatum L. and allied species. Part 3. Photoactive furocoumarins in two populations of Seseli elatum. Phytochemistry, 1988. 27 (4): 1073-1077.
  3. Xanthotoxol exerts neuroprotective effects via suppression of the inflammatory response in a rat model of focal cerebral ischemia. He W, Chen W, Zhou Y, Tian Y and Liao F, Cell Mol Neurobiol., July 2013, volume 33, issue 5, pages 715-722, doi:10.1007/s10571-013-9939-2
  4. Bang-Le Zhang, Cheng-Qi Fan, Lei Dong, Fang-Dao Wang, Jian-Min Yue. . European Journal of Medicinal Chemistry. 2010-11, 45 (11): 5258–5264 [2021-11-23]. doi:10.1016/j.ejmech.2010.08.045. (原始内容存档于2022-06-24) (英语).
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