10'R-karatavicinol | 670221-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 10'R-karatavicinol
• 英文别名: karatavicinol；7-[(2E,6E,10R)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienoxy]chromen-2-one
• CAS: 670221-79-1
• 化学式: C₂₄H₃₂O₅
• 分子量: 400.515
• InChiKey: SOTUFGKJQVSOCT-PKAURPTQSA-N

物化性质

• 沸点：
  582.8±50.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10'R-karatavicinol 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以53%的产率得到10'R-acetoxy-11'-hydroxyumbelliprenin
  参考文献：
  名称：

  A Practical Synthesis of a Hydroxylated Sesquiterpene Coumarin 10’R-Acetoxy-11’-hydroxyumbelliprenin by Regioselective Dihydroxylation

  摘要：

  A practical synthesis of 10'R-acetoxy-11'-hydroxyumbelliprenin was achieved using regioselective Sharpless asymmetric dihydroxylation as a key reaction, in which the regioselectivity was achieved by using (DHQD)(2)AQN as a ligand instead of the conventional (DHQD)(2)PHAL. 10'R-Acetoxy-11'-hydroxyumbelliprenin was synthesized by the coupling of a coumarin unit (umbelliferone) and sesquiterpene unit in 11% overall yield through 5 steps.

  DOI：

  10.3987/com-12-12636
• 作为产物：
  描述：

  7-羟基香豆素 、 反式,反式-金合欢醇 在 potassium osmate 、 potassium carbonate 、 hydroquinidine (anthraquinone-1,4-diyl) diether 、 potassium hexacyanoferrate(III) 、 对甲苯磺酸 作用下， 以 水 、 叔丁醇 、 丙酮 为溶剂， 反应 14.0h， 以31.3 mg的产率得到10'R-karatavicinol
  参考文献：
  名称：

  A Practical Synthesis of a Hydroxylated Sesquiterpene Coumarin 10’R-Acetoxy-11’-hydroxyumbelliprenin by Regioselective Dihydroxylation

  摘要：

  A practical synthesis of 10'R-acetoxy-11'-hydroxyumbelliprenin was achieved using regioselective Sharpless asymmetric dihydroxylation as a key reaction, in which the regioselectivity was achieved by using (DHQD)(2)AQN as a ligand instead of the conventional (DHQD)(2)PHAL. 10'R-Acetoxy-11'-hydroxyumbelliprenin was synthesized by the coupling of a coumarin unit (umbelliferone) and sesquiterpene unit in 11% overall yield through 5 steps.

  DOI：

  10.3987/com-12-12636

文献信息

• Influenza A (H₁N₁) Antiviral and Cytotoxic Agents from <i>Ferula assa-foetida</i>
  作者：Chia-Lin Lee、Lien-Chai Chiang、Li-Hung Cheng、Chih-Chuang Liaw、Mohamed H. Abd El-Razek、Fang-Rong Chang、Yang-Chang Wu

  DOI：10.1021/np900158f

  日期：2009.9.25

  Two new sesquiterpene coumarins, designated 5'-acetoxy-8'-hydroxyumbelliprenin (1) and 10'R-acetoxy-11'-hydroxyumbelliprenin (2), and a new diterpene, 15-hydroxy-6-en-dehydroabietic acid (3). along with 27 known compounds, were isolated from a CHCl3-soluble extract of Ferula assa-foetida through bioassay-guided fractionation. The structures of the new metabolites 1-3 were identified by spectroscopic data interpretation and by the Mosher ester method. Compounds 4 and 6-13 showed greater potency against influenza A virus (H1N1) (IC50 0.26-0.86 mu g/mL) than amantadine (IC50 0.92 mu g/mL), and 11 exhibited the best potency (IC50 0.51, 2.6, and 3.4 mu g/mL) of these compounds against the HepG2, Hep3B, and MCF-7 cancer cell lines, respectively.
• COMPOSITION FOR TREATING INFLUENZA A (H1N1) VIRUS AND A PREPARATION METHOD THEREFOR
  申请人：Wu Yang-Chang

  公开号：US20110196029A1

  公开（公告）日：2011-08-11

  New pharmaceutical compositions extracted from Ferula assa - foetida are confirmed to effectively treat influenza A (H 1 N 1 ) virus. The extraction method of the new pharmaceutical compositions mainly includes steps of (a) extracting F. assa - foetida with methanol to obtain a crude extract; (b) fractioning the crude extract with n-hexane-methanol to obtain a methanol extract; (c) fractioning the methanol extract with chloroform-water to obtain a chloroform extract; and (d) chromatographing the chloroform extract to obtain the pharmaceutical compositions, which can be further fractioned and chromatographed to obtain various sesquiterpene coumarins.
• US8476311B2
  申请人：——

  公开号：US8476311B2

  公开（公告）日：2013-07-02
• US8815949B2
  申请人：——

  公开号：US8815949B2

  公开（公告）日：2014-08-26
• US8993618B2
  申请人：——

  公开号：US8993618B2

  公开（公告）日：2015-03-31