benzyl 3-hydroxyoctanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-hydroxyoctanoate
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: UNJZFNRAJJMUMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 3-hydroxyoctanoate 在 吡啶 、 chromium(VI) oxide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 20.0h， 生成 3-氧代辛酸
  参考文献：
  名称：

  Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds

  摘要：

  A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.

  DOI：

  10.1007/s00253-015-6984-4
• 作为产物：
  描述：

  3-羟基辛酸 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 benzyl 3-hydroxyoctanoate
  参考文献：
  名称：

  环二肽磺酰胺A和B的全合成和结构验证

  摘要：

  微生物是具有抗菌特性的新天然产物的诱人来源，海洋环境构成了生物活性微生物的丰富资源。在一项全球研究探险活动（Galathea III）中，从海洋细菌光致细菌耐盐细菌中分离出了两种depsipeptide，即solonamide A和solonamide B，并发现它们可抑制严重人类病原体金黄色葡萄球菌中的毒力基因表达。它们通过干扰农业群体感应系统来发挥作用，并显示出与内源性金黄色葡萄球菌的相似之处。群体感应肽，自动诱导肽I（AIP-1）。为了进行更全面的研究，我们着手化学合成了磺酰胺A和B。关键的合成步骤是通过立体选择性羟醛反应和环化大内酰胺化反应形成（R）-β-羟基脂肪酸。在高度稀薄的条件下。因此，solonamides的第一个全合成证实了最初分配的结构，并通过改变辅助的立体醛醇缩合步骤中，我们获得了对天然产品接入以及他们β 3差向异构体。

  DOI：

  10.1016/j.tet.2014.05.107

文献信息

• Cyclic depsipeptides and drugs containing the same as the active ingredient
  申请人：Yanai Makoto

  公开号：US06858585B1

  公开（公告）日：2005-02-22

  Cyclic depsipeptides represented by the formula wherein: R is a straight or branched alkyl group of 5-20 carbon atoms or a straight or branched alkoxymethyl group of 5-15-carbon atoms; A, B, D, E and F independently each other are alanine, valine, leucine, isoleucine, phenylalanine, etc.; W and Z independently each other are aspartic acid, asparagine, glutamic acid or glutamine; and m and n independently each other is 0 or 1, or pharmacologically acceptable salts thereof. The present compounds are prepared according to a method conventionally used in peptide synthesis. The present compounds are useful as an agent for promoting the production of apolipoprotein E, a therapeutic agent for neurologic damages, a therapeutic agent for dementia, an agent for inhibiting the production of apolipoprotein B, an agent for promoting the production of apolipoprotein A1 or a therapeutic agent for hyperlipemia.

  公式表示的环状脱氢肽类化合物，其中：R是直链或支链烷基，其碳原子数为5-20，或直链或支链烷氧甲基，其碳原子数为5-15；A、B、D、E和F各自独立地是丙氨酸、缬氨酸、亮氨酸、异亮氨酸、苯丙氨酸等；W和Z各自独立地是天冬氨酸、天冬酰胺、谷氨酸或谷氨酰胺；m和n各自独立地为0或1，或其药学上可接受的盐。该化合物是通过肽合成中常规方法制备而成。该化合物可用作促进载脂蛋白E生产的药物，治疗神经损伤的药物，治疗痴呆症的药物，抑制载脂蛋白B生产的药物，促进载脂蛋白A1生产的药物或治疗高脂血症的药物。
• CYCLIC DEPSIPEPTIDES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：EP0967222A1

  公开（公告）日：1999-12-29

  Cyclic depsipeptides represented by the formula (1) (wherein: R is a straight or branched alkyl group of 5-20 carbon atoms or a straight or branched alkoxymethyl group of 5-15 carbon atoms; A, B, D, E and F independently each other are alanine, valine, leucine, isoleucine, phenylalanine, etc.; W and Z independently each other are aspartic acid, asparagine, glutamic acid or glutamine; and m and n independently each other is 0 or 1) or pharmacologically acceptable salts thereof. The present compounds are prepared according to a method conventionally used in peptide synthesis. The present compounds are useful as an agent for promoting the production of apolipoprotein E, a therapeutic agent for neurologic damages, a therapeutic agent for dementia, an agent for inhibiting the production of apolipoprotein B, an agent for promoting the production of apolipoprotein A1 or a therapeutic agent for hyperlipemia.

  由式(1)代表的环状去肽类化合物 其中 R是5-20个碳原子的直链或支链烷基或5-15个碳原子的直链或支链烷氧基甲基；A、B、D、E和F各自独立地为丙氨酸、缬氨酸、亮氨酸、异亮氨酸、苯丙氨酸等；W和Z各自独立地为天冬氨酸、天冬酰胺、谷氨酸或谷氨酰胺；m和n各自独立地为0或1）或其药理学上可接受的盐。本化合物是按照肽合成的常规方法制备的。本化合物可用作促进脂蛋白 E 生成的制剂、神经损伤的治疗剂、痴呆症的治疗剂、抑制脂蛋白 B 生成的制剂、促进脂蛋白 A1 生成的制剂或高血脂症的治疗剂。
• EP967222
  申请人：——

  公开号：——

  公开（公告）日：——
• US6858585B1
  申请人：——

  公开号：US6858585B1

  公开（公告）日：2005-02-22