落羽松酮

落羽松酮(英語:Taxodone)是一种二萜有机化合物,化学式C20H28O3,存在于落羽杉Taxodium distichum)、迷迭香Salvia rosmarinus)等植物中。[1][2][3]

落羽松酮
Taxodone
Taxodone 3d
IUPAC名
6α,11-Dihydroxyabieta-7,9(11),13-trien-12-one
系统名
(4bS,8aS,9S)-4,9-Dihydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthren-3(4bH)-one
别名 NSC122420, AC1L9XIL, CID457961
识别
CAS号 19039-02-2  checkY
PubChem 275528
ChemSpider 242416
SMILES
 
  • O=C1\C(=C/C=2/C(=C1/O)[C@]3(C)[C@@H]([C@@H](O)C=2)C(C)(C)CCC3)C(C)C
InChI
 
  • 1/C20H28O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,14,18,21,23H,6-8H2,1-5H3/t14-,18-,20+/m0/s1
InChIKey QEAIMIKGLGBTSA-ADLFWFRXBH
性质
化学式 C20H28O3
摩尔质量 316.43 g·mol−1
外观 Golden crystalline solid
熔点 176 - 177 °C(272 K)
溶解性 Insoluble
溶解性(chloroform, alcohol, hexane, ether) Soluble
相关物质
相关化学品 落羽松二酮
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

参考文献

  1. ^ Kupchan, S. M.; Karim, A; Marcks, C. Tumor inhibitors. XXXIV. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum. J. Am. Chem. Soc. 1968, 90 (21): 5923–5924. PMID 5679178. doi:10.1021/ja01023a061. 
  2. ^ Zaghloul A. M.; Gohar A. A.; Naiem Z. A.; Abdel Bar F. M. Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.).. Z. Naturforsch. C. 2008, 63 (5–6): 355–360. PMID 18669020. S2CID 23956301. doi:10.1515/znc-2008-5-608 . 
  3. ^ Ayhan Ulubelen, Gülaçti Topçu, Hee-Byung Chai and John M. Pezzuto. Cytotoxic Activity of Diterpenoids Isolated from Salvia hypargeia. Pharmaceutical Biology. 1999, 37 (2): 148–151. doi:10.1076/phbi.37.2.148.6082.