(R)-2-hydroxy-4-oxo-henicosan-1-yl acetate | 163955-67-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-hydroxy-4-oxo-henicosan-1-yl acetate
• 英文别名: (R)-2-hydroxy-4-oxohenicosan-1-yl acetate；(+)-(R)-2-hydroxy-4-oxohenicosyl acetate；(+)-(R)-tetrahydropersin；[(2R)-2-hydroxy-4-oxohenicosyl] acetate
• CAS: 163955-67-7
• 化学式: C₂₃H₄₄O₄
• 分子量: 384.6
• InChiKey: ZLVJJMWEIHRVLD-HSZRJFAPSA-N

物化性质

• 熔点：
  71-72 °C
• 沸点：
  501.5±35.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-4-oxo-henicosan-1-yl acetate 在 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以99%的产率得到2-(heptadecyl)furan
  参考文献：
  名称：

  2-Hydroxy-4-oxohenicosan-1-yl Acetate. Its Presence in Avocado and its Simple Chemistry

  摘要：

  标题化合物（1b）存在于鳄梨叶中。描述了该 描述。

  DOI：

  10.1071/ch00040
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、103.42 kPa 条件下， 反应 32.67h， 生成 (R)-2-hydroxy-4-oxo-henicosan-1-yl acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells

  摘要：

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.006

文献信息

• US6057366A
  申请人：——

  公开号：US6057366A

  公开（公告）日：2000-05-02
• [EN] METHOD OF TREATMENT OF CANCER AS WELL AS METHOD OF INHIBITION OF LACTATION IN MAMMALS<br/>[FR] PROCEDE DE TRAITEMENT DU CANCER ET PROCEDE D'INHIBITION DE LA LACTATION CHEZ DES MAMMIFERES
  申请人：THE UNIVERSITY OF QUEENSLAND

  公开号：WO1995022969A1

  公开（公告）日：1995-08-31

  (EN) A method of treatment of mammals suffering from cancer and in particular breast cancer including the step of administration of compounds for formula (1) herein wherein R is a side chain of 4 to 20 carbons which may tolerate a minor degree of unsaturation as well as a minor degree of branching.(FR) Procédé de traitement de mammifères souffrant de cancer, et notamment du cancer du sein, comprenant l'étape d'administration de composés de la formule (1) dans laquelle R représente une chaîne latérale de 4 à 20 atomes de carbone, laquelle peut tolérer à un degré réduit d'insaturation et de ramification.
• Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells
  作者：Darby G. Brooke、Elizabeth J. Shelley、Caroline G. Roberts、William A. Denny、Robert L. Sutherland、Alison J. Butt

  DOI：10.1016/j.bmc.2011.10.006

  日期：2011.12

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.
• 2-Hydroxy-4-oxohenicosan-1-yl Acetate. Its Presence in Avocado and its Simple Chemistry
  作者：Raymond M. Carman、Alan R. Duffield、Paul N. Handley、Tomislav Karoli

  DOI：10.1071/ch00040

  日期：——

  The title compound (1b) is present in avocado leaves. Simple chemistry of the compound is described.

  标题化合物（1b）存在于鳄梨叶中。描述了该 描述。