| 山道年 | |
|---|---|
| |
| |
| IUPAC名 (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione | |
| 识别 | |
| CAS号 | 481-06-1 
|
| PubChem | 221071 |
| ChemSpider | 191779 |
| SMILES |
|
| InChI |
|
| InChIKey | XJHDMGJURBVLLE-BOCCBSBMBZ |
| ChEBI | 16363 |
| 性质 | |
| 化学式 | C15H18O3 |
| 摩尔质量 | 246.3 g·mol−1 |
| 熔点 | 172 °C（445 K） |
| 沸点 | 423 °C（696 K） |
| 溶解性（水） | 难溶 |
| 蒸气压 | 1*10−7mmHg |
| 若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。 | |
山道年，也称散道宁、蛔蒿素，是从菊科植物蛔蒿的花中提取的一种酮内酯化学物质，可用作驱虫药。过去被美英等国药典列为蛔虫药，在中国也曾用于宝塔糖。现已被效力更强、毒性更低的药物所代替。[1]
水解可成为山道年酸 (C15H20O4)。[2][3][4][5][6][7]
可能的生物合成
药用
可处理蛔虫等线虫感染，对绦虫无效。山道年使虫体麻痹；服药后，还应吃泻药以排出蛔虫。
山道年中毒可造成黄视、绿视。服用之前与之后起码3天不能吃油脂，以免脂溶性的山道年摄入体内。
参考文献
- ↑ Modern Drug Encyclopedia and Therapeutic Index, Sixth Edition, Drug Publications Inc, 1955
- ↑ Base-catalyzed rearrangements
- ↑ Per the Encyclopædia Britannica (1911 edition)
- ↑ Modern botanicals also list Artemisia cina or Levant wormwood as the definitive source; this is also backed up by statements in formularies published in the heyday of santonin use such as King's American Dispensatory.
- ↑ King's American Dispensatory, 1898 (this work is now in the public domain)
- ↑ Botanical.com (article on Levant Wormseed, primary source of santonin)
- ↑ original source, US Pharmacopoeia, 1898
- ↑ 1. de Kraker, J.W.; Franssen, M.C.; Dalm M.C.; de Groot, A.; Bouwmeester, H.J.; “Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene a hydroxylase and NADP+-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis”. (2001). Plant Physiol. 125(4): 1930-40.
- ↑ Barton, D.H.R.; Moss, G.P.; Whittle, J.A.; “Investigations on the Biosynthesis of Steroids and Terpenoids. Part I. A Preliminary Study of the Biosynthesis of Santonin”. (1968). J. Chem. Soc. 338(8): 1813-18.
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本条目部分或全部内容出自公有领域：Chisholm, Hugh (编). 大英百科全書 24 (11th ed.). 剑桥大学出版社: 195. 1911.