15β–acetoxy–(–)–kaur–16–en–l9–oic acid | 6619-97-2

• 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: 15β–acetoxy–(–)–kaur–16–en–l9–oic acid
• 英文别名: ent-15-β-acetyloxy-kaur-16-en-19-oic acid；xylopic acid；(10S)-15β-acetoxy-kaur-16-en-19-oic acid；(10S)-15β-Acetoxy-kaur-16-en-19-saeure；Xylopsaeure；(1R,4S,5R,9S,10S,13R,15R)-15-Acetyloxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 6619-97-2
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: AQBQBBLJTDSVLC-XNAIKIDQSA-N

物化性质

• 熔点：
  265-266 °C
• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  15β–acetoxy–(–)–kaur–16–en–l9–oic acid 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.5h， 生成 Methyl 15β-hydroxy-ent-kaur-16-en-19-oate
  参考文献：
  名称：

  Synthesis,in vitroAntimalarial Activity andin silicoStudies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes

  摘要：

  We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The Cu-I-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.

  DOI：

  10.5935/0103-5053.20150287

文献信息

• Chemistry of the constituents of Xylopia aethiopica. The structure of xylopic acid, a new diterpene acid
  作者：D. E. U. Ekong、A. U. Ogan

  DOI：10.1039/j39680000311

  日期：——

  From the dried fruits of Xylopia aethiopica has been isolated a new diterpene acid, xylopic acid, which is shown to be 15β-acetoxy-(–)-kaur-16-en-19-oic acid.

  从的干果Xylopia马蹄莲已分离出一种新的二萜酸，xylopic酸，其被示出为15β乙酰氧基- （ - ） -考尔-16-烯-19-酸。
• Fluorinated kaurenoids. Part 2. Preparation of methyl ent-17,17,17-trifluorokaur-15-en-19-oate and ent-16,16-difluoro-17-norkauran-19-oic acid from xylopic acid
  作者：Brian E. Cross、Anton Erasmuson、Paolino Filippone

  DOI：10.1039/p19810001293

  日期：——

  An attempt to convert methyl ent-16-oxo-17-norkauran-19-oate (3), derived from xylopic acid, into methyl ent-17,17-difluorokaur-16-en-19-oate failed. However, treatment of the norketone (3) with diethylaminosulphur trifluoride (DAST) gave methyl ent-16,16-difluoro-17-norkauran-19-oate (5). The latter afforded the corresponding acid (4) which was active as a growth promoter in a dwarf-rice bioassay

  尝试将源自木糖二酸的eNT甲基-16-oxo-17-norkauran-19-oate（3）转换为eNT -1,17-difluorokaur-16-en-19-oate甲基戊酸。然而，治疗norketone（3）用二乙基三氟化硫（DAST）的给甲基ENT -16,16二氟-17- norkauran-19 -酸酯（5）。后者提供了相应的酸（4），在矮米生物测定中可作为生长促进剂起作用。甲基deacetylxylopate（18）与DAST，然后由终端亚甲基的裂解处理，得到甲基ENT -15-氟-16-氧代-17- norkauran-19 -酸酯（15），其与二溴二氟甲烷和三（反应二甲基氨基）膦，得到，而不是预期的17,17-二氟烯烃（19），但甲基ENT-17,17,17-trifluorokaur-15-en-19-oate（28）收率不佳。用二酰亚胺还原草酰氯甲酯可立体定向得到16
• The biotransformation of ent-15-oxokaur-16-en-19-oic acid and its methyl ester by Cephalosporium aphidicola
  作者：Alaide B. de Oliveira、James R. Hanson、Jacqueline A. Takahashi

  DOI：10.1016/0031-9422(95)00289-j

  日期：1995.9

  ent-15-Oxokaur-16-en-19-oic acid and its methyl ester are transformed to ent-11α,16β-dihydroxy-15-oxokauran-19-oic acid and its methyl ester, respectively, by Cephalosporium aphidicola.

  Cephalosporium aphidicola 将 ent-15-Oxokaur-16-en-19-oic 酸及其甲酯分别转化为 ent-11α,16β-dihydroxy-15-oxokauran-19-oic 酸及其甲酯。
• Forced degradation studies, elucidation of degradation pathways and degradation kinetics of Xylopic acid via LC and LC-MS/MS analyses
  作者：Raphael N. Alolga、Isaac Ayensu、Jerry X. Sosu

  DOI：10.1016/j.xphs.2023.01.004

  日期：2023.1

  to various stress conditions (hydrolytic, oxidative, photolytic and thermal) and its degradation products characterized. Seven degradation products were identified and tentatively characterized by LC-MS/MS analysis. The probable degradation pathways for the seven degradation products were then predicted. Using a simple and validated UHPLC-DAD method, the degradation kinetics of XA under the different

  活性药物成分 (API) 的稳定性研究仍然是制药行业的基本质量要求。API的稳定性数据可以指导其加工技术、包装方法和储存条件的选择。在这里，我们试图确定木吡酸 (XA) 在国际协调会议 (ICH) 规定的各种应力条件下的稳定性。XA 是非洲香料XyloPIa aethioPIca （番荔枝科）的二​​萜贝壳杉烯分离物，具有多种生物活性。XA 经受各种应激条件（水解、氧化、光解和热），并对其降解产物进行了表征。通过 LC-MS/MS 分析鉴定并初步表征了七种降解产物。然后预测了七种降解产物的可能降解途径。使用简单且经过验证的 UHPLC-DAD 方法，综合评估了 XA 在不同胁迫条件下的降解动力学。XA在所有应力条件下的降解均遵循一级反应动力学。人们发现 XA 在强酸性或强碱性溶液以及氧化剂（过氧化氢）中不太稳定。XA 的稳定性还依赖于 pH 值和温度。然而，其稳定性不受紫外光照射的影响。