exophilin A | 172703-87-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: exophilin A
• 英文别名: (3R,5R)-5-[(3R,5R)-5-[(3R,5R)-3,5-dihydroxydecanoyl]oxy-3-hydroxydecanoyl]oxy-3-hydroxydecanoic acid
• CAS: 172703-87-6
• 化学式: C₃₀H₅₆O₁₀
• 分子量: 576.769
• InChiKey: RZQNQMRSGMXXMH-ZRRJEQDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  171
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  exophilin A 以17.6 mg的产率得到(4R,6R)-4-hydroxy-6-pentyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Exophilin A，来自海洋微生物Exophiala pisphilphila的新型抗生素。

  摘要：

  在从海洋海绵Mycale adhaerens分离出来的海洋微生物Exophiala pisciphila NI10102的培养物中发现了一种新的抗菌化合物ExophilinA。通过光谱法和降解产物的分析，阐明了作为（3R，5R）-3，5-二羟基癸酸三聚体的外泌素A的绝对化学结构。Exophilin A对革兰氏阳性细菌具有抗菌活性。

  DOI：

  10.7164/antibiotics.49.1105
• 作为产物：
  描述：

  benzyl (3R,5R)-3-hydroxy-5-[(3R,5R)-3-hydroxy-5-[(Z,3R,5S)-3-hydroxy-5-phenylmethoxydec-6-enoyl]oxydecanoyl]oxydecanoate 在 10% Pd/C 、 氢气 、 calcium carbonate 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以94%的产率得到exophilin A
  参考文献：
  名称：

  Facile access to some chiral building blocks. Synthesis of verbalactone and exophilin A

  摘要：

  D-Glucono-1,5-lactone, all inexpensive carbohydrate, was elaborated into chiral building blocks readily applicable in synthesis via practical routes without involving any expensive reagents or tedious operations. Application Of Such chiral building blocks in total synthesis is then exemplified through construction of verbalactone and exophilin A. The latter compound has not been synthesized to date. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.050

文献信息

• Oils having antibacterial activity
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US10544085B2

  公开（公告）日：2020-01-28

  Compounds, called liamocins from Aureobasidium pullulans, having the general structure in Formula 1 are disclosed. where R1 is either COCH3 or H; and R2 is between two to ten O-linked 3,5-dihydroxydecanoate; and R3 can be a polyol (e.g., L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol (also called sorbitol), L- or D-galactitol (also called dulcitol), and L- or D-talitol), 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when R3 is D-mannitol, R2 is not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains. These liamocins described above in addition to D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, and D-mannitol liamocin B2, alone or in combination with each other, can be used to kill certain bacteria and to treat certain bacterial infections.

  本研究公开了来自 Aureobasidium pullulans 的称为 liamocins 的化合物，其一般结构如式 1 所示。 其中，R1 是 COCH3 或 H；R2 是 2 至 10 个 O-连接的 3,5-二羟基癸酸酯；R3 可以是多元醇（例如、L-或 D-甘油、L-或 D-苏糖醇、L-或 D-赤藓糖醇、L-或 D-阿拉比托醇、L-或 D-木糖醇、L-或 D-来苏糖醇、L-或 D-核糖醇、L-或 D-阿立糖醇、L-或 D-阿立糖醇、L-或 D-甘露糖醇、L-或 D-iditol、L-或 D-谷糖醇、L-或 D-葡萄糖糖醇（又称山梨糖醇）、L-或 D-半乳糖醇（又称杜醇）和 L-或 D-塔糖醇）、2-氨基-D-甘露糖醇、2N-乙酰氨基-D-甘露糖醇、L-鼠李糖醇或 D-岩藻糖醇；除了当 R3 是 D-甘露糖醇时，R2 不是 2 个也不是 3 个 O-连接的 3,5-二羟基癸酸链。除了 D-甘露醇利阿莫西林 A1、D-甘露醇利阿莫西林 A2、D-甘露醇利阿莫西林 B1 和 D-甘露醇利阿莫西林 B2 之外，上述这些利阿莫西林可单独或相互组合用于杀灭某些细菌和治疗某些细菌感染。
• JPH07285917A
  申请人：——

  公开号：JPH07285917A

  公开（公告）日：1995-10-31
• NOVEL OILS HAVING ANTIBACTERIAL ACTIVITY
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE

  公开号：US20170050916A1

  公开（公告）日：2017-02-23

  Novel compounds, called liamocins from Aureobasidium pullulans , having the general structure in Formula 1 are disclosed. where R 1 is either COCH 3 or H; and R 2 is between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 can be a polyol (e.g., L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol (also called sorbitol), L- or D-galactitol (also called dulcitol), and L- or D-talitol), 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when R 3 is D-mannitol, R 2 is not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains. These liamocins described above in addition to D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, and D-mannitol liamocin B2, alone or in combination with each other, can be used to kill certain bacteria and to treat certain bacterial infections.
• OILS HAVING ANTIBACTERIAL ACTIVITY
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US20180201571A1

  公开（公告）日：2018-07-19

  Compounds, called liamocins from Aureobasidium pullulans , having the general structure in Formula 1 are disclosed. where R 1 is either COCH 3 or H; and R 2 is between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 can be a polyol (e.g., L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol (also called sorbitol), L- or D-galactitol (also called dulcitol), and L- or D-talitol), 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when R 3 is D-mannitol, R 2 is not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains. These liamocins described above in addition to D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, and D-mannitol liamocin B2, alone or in combination with each other, can be used to kill certain bacteria and to treat certain bacterial infections.
• US9950986B2
  申请人：——

  公开号：US9950986B2

  公开（公告）日：2018-04-24