monosodium azelate | 17356-30-8

• 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: monosodium azelate
• 英文别名: sodium hydrogen azelate；sodium;9-hydroxy-9-oxononanoate
• CAS: 17356-30-8
• 化学式: C₉H₁₅O₄*Na
• 分子量: 210.205
• InChiKey: KITSBOHZGUHIOU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.44
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  14-iodo-N-(trifluoroacetyl)daunorubicin 、 monosodium azelate 以 水 、 丙酮 为溶剂， 以65%的产率得到N-(trifluoroacetyl)adriamycin 14-O-hemiazelate
  参考文献：
  名称：

  Adriamycin analogs. Rationale, synthesis, and preliminary antitumor evaluation of highly active DNA-nonbinding N-(trifluoroacetyl)adriamycin 14-O-hemiester derivatives

  摘要：

  N-(Trifluoroacetyl)adriamycin 14-valerate (AD 32), a novel DNA nonbinding analogue of adriamycin with superior experimental antitumor activity, has undergone extensive clinical trial, with documentation of antitumor activity and low toxicity in human subjects. However, poor water solubility necessitates that the drug be administered to patients by continuous intravenous infusion at high dilution in a surfactant-containing formulation, with steroid prophylaxis to protect against a chest pain syndrome associated with the vehicle. On the basis of pharmacologic considerations, the title compounds have been prepared as second-generation analogues of N-(trifluoroacetyl)adriamycin 14-valerate with improved aqueous solubility; use is made of the available carboxylic acid function to solubilize the products in dilute aqueous alkaline medium. Target compounds were made by treating N-(trifluoroacetyl)-14-halodaunorubicin (bromo or iodo) with monosodium salts of dibasic acids (malonic, succinic, glutaric, adipic, pimelic, azelaic, sebacic) in aqueous acetone. All of the products showed significant in vivo antitumor activity against the murine P388 leukemia (ip tumor, ip treatment once daily on days 1, 2, 3, and 4); most compounds were superior to the +181% increase in life span afforded by adriamycin (optimal dose 3.0 mg/kg per day), one of two drugs used as positive controls for the assays. Several of the test compounds showed highly curative activity in this system, similar to N-(trifluoroacetyl)adriamycin 14-valerate, the other positive control agent. The hemiadipate product exhibited the most desirable properties of high antitumor efficacy (86% cure rate all P388 tumor-bearing animals through four levels of a 40-70 mg/kg dose-response range), aqueous solubility (60 mg/mL in pH 7.4 phosphate buffer), and solution stability (no decomposition at 4 degrees C, 0.5% hydrolysis at 27 degrees C, over 24 h at pH 7.4).

  DOI：

  10.1021/jm00147a017
• 作为产物：
  描述：

  壬二酸 在 水 、 sodium hydroxide 作用下， 反应 0.17h， 生成 monosodium azelate
  参考文献：
  名称：

  新型抗菌壬二酸BioMOF

  摘要：

  在过去的几年中，用于生物应用的金属有机框架（MOF）的发展具有重要意义，这主要是由于它们作为药物载体和/或显像剂的潜力。尽管生物活性壬二酸也已被广泛用作抗菌和消炎药，但其溶解度较低，因此，最重要的是开发具有持续活性的更易溶解的制剂。在这项贡献中，我们证明了新的基于壬二酸的金属生物分子框架（BioMOFs）是实现此目标的可行途径。因此，通过简单，低成本和环境友好的机械化学方法制备了五种新颖的MOF，将壬二酸与内源性阳离子（即K +，Na +和Mg 2+）结合在一起：[K2（H 2 AZE）（AZE）]（1），[Na 4（HAZE）4 ]（2），[Na 2（AZE）（H 2 O）]（3）和[Mg （AZE）（H 2 O）3 ]（4）和（5）（其中H 2AZE-中性壬二酸；霾-单去质子化的壬二酸; AZE-二去质子化的壬二酸）。在使用单晶X射线衍射数据和其他互补的标准固态技术进行完整的结构表征后

  DOI：

  10.1021/acs.cgd.9b01302

文献信息

• SKIN CARE COMPOSITIONS
  申请人：Whewell Christopher J.

  公开号：US20070292382A1

  公开（公告）日：2007-12-20

  Provided are compositions which are suitable for topical application to human skin for cleansing and anti-microbial properties. In one preferred embodiment, the compositions include a glyceryl monoazelate ester. In another embodiment, the compositions include a glyceryl monoazelate monolaurate ester. It is postulated that bacteria on the skin cleave the ester linkage of a compound according to the invention that is applied to the skin, which causes liberation of the acid moiety from the ester, which acid moiety then inhibits or kills the bacterium. Compositions according to the invention may comprise skin creams, soaps, shampoos and lotions, and are especially effective in treating acne and acne-like skin ebullitions. The glyceryl portion of the molecules is believed to facilitate penetration of the ester into the skin.
• Skin care compositions
  申请人：Whewell J. Christopher

  公开号：US20080089854A1

  公开（公告）日：2008-04-17

  Provided are compositions which are suitable for topical application to human skin for cleansing and anti-microbial properties. In one preferred embodiment, the compositions include a glyceryl monoazelate ester. In another embodiment, the compositions include a glyceryl monoazelate monolaurate ester. It is postulated that bacteria on the skin cleave the ester linkage of a compound according to the disclosure that is applied to the skin, which causes liberation of the acid moiety from the ester, which acid moiety then inhibits or kills the bacterium. Compositions according to the disclosure may comprise skin creams, soaps, shampoos and lotions, and are especially effective in treating acne and acne-like skin ebullitions. The glyceryl portion of the molecules is believed to facilitate penetration of the ester into the skin.
• US7300957B1
  申请人：——

  公开号：US7300957B1

  公开（公告）日：2007-11-27
• Adriamycin analogs. Rationale, synthesis, and preliminary antitumor evaluation of highly active DNA-nonbinding N-(trifluoroacetyl)adriamycin 14-O-hemiester derivatives
  作者：Mervyn Israel、P. Gopalakrishnan Potti、Ramakrishnan Seshadri

  DOI：10.1021/jm00147a017

  日期：1985.9

  N-(Trifluoroacetyl)adriamycin 14-valerate (AD 32), a novel DNA nonbinding analogue of adriamycin with superior experimental antitumor activity, has undergone extensive clinical trial, with documentation of antitumor activity and low toxicity in human subjects. However, poor water solubility necessitates that the drug be administered to patients by continuous intravenous infusion at high dilution in a surfactant-containing formulation, with steroid prophylaxis to protect against a chest pain syndrome associated with the vehicle. On the basis of pharmacologic considerations, the title compounds have been prepared as second-generation analogues of N-(trifluoroacetyl)adriamycin 14-valerate with improved aqueous solubility; use is made of the available carboxylic acid function to solubilize the products in dilute aqueous alkaline medium. Target compounds were made by treating N-(trifluoroacetyl)-14-halodaunorubicin (bromo or iodo) with monosodium salts of dibasic acids (malonic, succinic, glutaric, adipic, pimelic, azelaic, sebacic) in aqueous acetone. All of the products showed significant in vivo antitumor activity against the murine P388 leukemia (ip tumor, ip treatment once daily on days 1, 2, 3, and 4); most compounds were superior to the +181% increase in life span afforded by adriamycin (optimal dose 3.0 mg/kg per day), one of two drugs used as positive controls for the assays. Several of the test compounds showed highly curative activity in this system, similar to N-(trifluoroacetyl)adriamycin 14-valerate, the other positive control agent. The hemiadipate product exhibited the most desirable properties of high antitumor efficacy (86% cure rate all P388 tumor-bearing animals through four levels of a 40-70 mg/kg dose-response range), aqueous solubility (60 mg/mL in pH 7.4 phosphate buffer), and solution stability (no decomposition at 4 degrees C, 0.5% hydrolysis at 27 degrees C, over 24 h at pH 7.4).
• Novel Antibacterial Azelaic Acid BioMOFs
  作者：Silvia Quaresma、Vânia André、Alexandra M. M. Antunes、Sérgio M. F. Vilela、Georgiana Amariei、Ana Arenas-Vivo、Roberto Rosal、Patricia Horcajada、M. Teresa Duarte

  DOI：10.1021/acs.cgd.9b01302

  日期：2020.1.2

  environmentally friendly mechanochemical approach, combining azelaic acid with endogenous cations (i.e., K+, Na+, and Mg2+): [K2(H2AZE)(AZE)] (1), [Na4(HAZE)4] (2), [Na2(AZE)(H2O)] (3), and two different polymorphic forms of [Mg(AZE)(H2O)3] (4) and (5) (where H2AZE - neutral azelaic acid; HAZE - mono-deprotonated azelaic acid; AZE - di-deprotonated azelaic acid). After full structural characterization using single-crystal

  在过去的几年中，用于生物应用的金属有机框架（MOF）的发展具有重要意义，这主要是由于它们作为药物载体和/或显像剂的潜力。尽管生物活性壬二酸也已被广泛用作抗菌和消炎药，但其溶解度较低，因此，最重要的是开发具有持续活性的更易溶解的制剂。在这项贡献中，我们证明了新的基于壬二酸的金属生物分子框架（BioMOFs）是实现此目标的可行途径。因此，通过简单，低成本和环境友好的机械化学方法制备了五种新颖的MOF，将壬二酸与内源性阳离子（即K +，Na +和Mg 2+）结合在一起：[K2（H 2 AZE）（AZE）]（1），[Na 4（HAZE）4 ]（2），[Na 2（AZE）（H 2 O）]（3）和[Mg （AZE）（H 2 O）3 ]（4）和（5）（其中H 2AZE-中性壬二酸；霾-单去质子化的壬二酸; AZE-二去质子化的壬二酸）。在使用单晶X射线衍射数据和其他互补的标准固态技术进行完整的结构表征后