法卡林二醇 | 55297-87-5

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 法卡林二醇
• 中文别名: 福尔卡烯炔二醇；1,9-十七烯-4,6-二炔-3,8-二醇；(3R,8S,9Z)-十六碳-1,9-二烯-4,6-二炔-3,8-二醇
• 英文名称: (+)-Falcarindiol
• 英文别名: (3S,8S,Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol；(3S,8S)-falcarindiol；3S,8S-falcarindiol；falcalindiol；falcarindiol；1,9-Heptadecadiene-4,6-diyne-3,8-diol；(3S,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol
• CAS: 55297-87-5
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: QWCNQXNAFCBLLV-RCQSYPNMSA-N

物化性质

• 沸点：
  408.2±45.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)
• LogP：
  6.318 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

制备方法与用途

化学性质：无色或淡黄色的油状物，可溶于甲醇、乙醇和DMSO等有机溶剂，来源于北沙参和羌活。

用途：法卡林二醇具有解热、镇痛、镇咳、祛痰、强心以及抗突变的作用。

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 法卡林二醇 在 吡啶 、 4-二甲氨基吡啶 作用下， 以75%的产率得到(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (Z)-(S)-1-[(S)-5-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hept-6-ene-1,3-diynyl]-dec-2-enyl ester
  参考文献：
  名称：

  Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus

  摘要：

  The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diynene (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model.

  DOI：

  10.1021/np960224o
• 作为产物：
  描述：

  (S,Z)-1-(trimethylsilyl)dodec-4-en-1-yn-3-ol 在 盐酸羟胺 、 potassium carbonate 、 乙胺 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 法卡林二醇
  参考文献：
  名称：

  锌-氨基-醇络合物催化三甲基甲硅烷基乙炔向醛的高度对映选择性加成

  摘要：

  很好的补充！已开发出一种高度对映选择性和高效的程序，用于氨基醇锌催化的三甲基甲硅烷基乙炔加成到芳族，α，β-不饱和和脂肪族醛中（见方案； R =芳基，炔基或烷基； TMS =三甲基甲硅烷基； TBDMS =叔丁基二甲基甲硅烷基）。本协议已成功地应用于天然产物海洋炔醇和法卡林二醇的简明合成中。

  DOI：

  10.1002/chem.201100535

文献信息

• Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma
  作者：Satoru Tamura、Tomomichi Ohno、Yuuhi Hattori、Nobutoshi Murakami

  DOI：10.1016/j.tetlet.2010.01.047

  日期：2010.3

  Falcarindiol (1) was isolated as an algicidal principle against the harmful red tide dinoflagellate, Heterocapsa circularisquama, from Notopterygii Rhizoma through bioassay-guided separation. In order to determine the ambiguous absolute structure of this active principle, all three stereoisomers as well as falcarindiol (1) were synthesized. As a result of intensive analysis of their physicochemical properties, the configuration of I was revealed to be 3R,8S. On the other hand, (3S,8S)- and (3S,8R)-isomers were found to exhibit more potent algicidal activity than (3R,8S)-falcarindiol (1) isolated from Notopterygii Rhizoma. In addition, the diyne moiety of 1 was established as the crucial structural requirement for algicidal potency. (C) 2010 Elsevier Ltd. All rights reserved.