2-己基-5-戊基苯-1,3-二醇 | 139552-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-己基-5-戊基苯-1,3-二醇
• 中文别名: 6,8-二氧杂二环3.2.1辛烷,4-溴-7-丙基-,(4-exo,7-endo)-
• 英文名称: resorstatin [2-hexyl-5-pentylbenzene-1,3-diol]
• 英文别名: 2-hexyl-5-pentyl-1,3-resorcinol；2-hexyl-5-pentylresorcinol；resorstatin；2-hexyl-5-pentylbenzene-1,3-diol
• CAS: 139552-96-8
• 化学式: C₁₇H₂₈O₂
• 分子量: 264.408
• InChiKey: GAZJVWPMPITOLB-UHFFFAOYSA-N

物化性质

• 沸点：
  406.5±15.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-己基-5-戊基苯-1,3-二醇 以 氘代氯仿 为溶剂， 反应 56.0h， 生成 2-hexyl-3-hydroxy-5-pentylbenzo-1,4-quinone
  参考文献：
  名称：

  Antimicrobial Dialkylresorcinols from Pseudomonas sp. Ki19

  摘要：

  Four dialkylresorcinols (1-4) were isolated from a liquid culture of Pseudomonas sp. Ki19. Compounds 1 and 2, 2-butyl-5-propylresorcinol and 2-hexyl-5-methylresorcinol, respectively, have not previously been isolated from biological sources, whereas 3 and 4, 2-hexyl-5-propylresorcinol (DB-2073) and 2-hexyl-5-pentylresorcinol ( resorstatin), both have been found in biological systems. The compounds inhibited Staphyllococcus aureus at concentrations <= 10 mu g/mL as well as the fungi Aspergillus fumigatus and Fusarium culmorum at 50 mu g/mL. The formation of possible antimicrobial quinone oxidation products was investigated under bioassay conditions, and they were not found to be responsible for the main antimicrobial activity.

  DOI：

  10.1021/np0600595
• 作为产物：
  描述：

  橄榄醇二甲基醚 在 叔丁基锂 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-己基-5-戊基苯-1,3-二醇
  参考文献：
  名称：

  A Simple Synthesis of the Natural 2,5-Dialkylresorcinol Free Radical Scavenger Antioxidant: Resorstatin

  摘要：

  3,5-Dimethoxybenzoic acid 3 has been transformed into olivetol dimethyl ether 6 in three steps in 79% yield. Directed ortho-metallation-alkylation of 6, followed by boron tribromide demethylation resulted in a simple and inexpensive synthesis of resorstatin, in 70% overall yield from 3.

  DOI：

  10.1080/00397919708007301

文献信息

• High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction
  作者：Rudrakshula Madhavachary、Dhevalapally B. Ramachary

  DOI：10.1002/ejoc.201403128

  日期：2014.11

  Biologically important, less-explored natural products of sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues were synthesized in very good yields in a sequential two-pot manner by using an “organocatalytic reductive coupling reaction” as the key step.

  通过使用“有机催化还原偶联反应”作为关键步骤，以连续两锅的方式以非常好的收率合成了具有生物学意义的、较少探索的具有性欺骗性的 chiloglottones、抗菌二烷基间苯二酚及其许多类似物的天然产物。
• Isolation, Identification, and Decomposition of Antibacterial Dialkylresorcinols from a Chinese <i>Pseudomonas aurantiaca</i> Strain
  作者：Yue Shi、Diana A. Zaleta-Pinet、Benjamin R. Clark

  DOI：10.1021/acs.jnatprod.9b00315

  日期：2020.2.28

  dialkylresorcinols 1 and 2. Extensive decomposition studies on the major metabolite 1 produced an additional furanone derivative (6), a hydroxyquinone (7), and two unusual resorcinol and hydroxyquinone dimers (8 and 9). Structures were elucidated by nuclear magnetic resonance spectroscopy in combination with tandem mass spectrometry analysis. These studies illustrate the potential of artifacts as a source

  除已知的二烷基间苯二酚1和2外，对中国假单胞菌Aurantiaca菌株的化学研究还产生了新的苯醌（4）和呋喃酮（5）。对主要代谢产物1的广泛分解研究还产生了另一种呋喃酮衍生物（6），一个羟基醌（7），以及两个不同寻常的间苯二酚和羟基醌二聚体（8和9）。通过核磁共振波谱结合串联质谱分析来阐明结构。这些研究说明了人工制品作为其他化学多样性来源的潜力。化合物1和2对一组革兰氏阳性病原体表现出中等的抗菌活性，而人工制品（4-9）的抗菌活性却降低了。
• Semi-synthesis of antibacterial dialkylresorcinol derivatives
  作者：Jianye Li、Yue Shi、Benjamin R. Clark

  DOI：10.1038/s41429-020-0359-5

  日期：2021.1

  dialkylresorcinols isolated from a Pseudomonas aurantiaca strain has yielded 21 derivatives, which were tested for antimicrobial activity, revealing several trends in their activity. The presence of aromatic and phenolic hydrogen atoms was crucial for activity, with all derivatives lacking these features possessing greatly reduced activity. On the other hand, derivatives with shorter alkyl chains at C-5 possessed lower

  二烷基间苯二酚是由多种细菌产生的一类抗菌天然产物。从aseantimonus aurantiaca菌株中分离出的两种微生物二烷基间苯二酚的半合成衍生化反应产生了21种衍生物，并对其抗微生物活性进行了测试，揭示了其活性的几种趋势。芳族和酚氢原子的存在对于活性至关重要，所有缺乏这些特征的衍生物都具有大大降低的活性。另一方面，在C-5处具有较短烷基链的衍生物具有较低的MIC值，而一种单氟代硫酸化衍生物显示出对几种测试菌株的显着改善的活性。
• Deciphering the biotransformation mechanism of dialkylresorcinols by CYP4F11
  作者：Yue Shi、Clemens A. Wolf、Rowaa Lotfy、Sangeeta S. Sharma、Abel Fekadu Tesfa、Gerhard Wolber、Matthias Bureik、Benjamin R. Clark

  DOI：10.1016/j.bioorg.2022.106330

  日期：2023.2

  exclusively at the ω-position of the C-5 alkyl chain. Homology modeling studies revealed that optimal hydrogen bonding between 2 and the enzyme can only be established with the C-5 alkyl chain pointing towards the heme. The closely-related CYP4F12 was not capable of oxidizing the dialkylresorcinol 2. Modeling experiments rationalize these differences by the different shapes of the binding pockets with respect

  细胞色素 P450 酶 (CYP) 是人体内最重要的一类氧化酶，负责代谢各种外源性和内源性底物。为了扩展对这些酶的特异性的认识并获得新的天然产物衍生物，将细胞色素 P450 单加氧酶 CYP4F11 用于一对抗生素微生物天然产物二烷基间苯二酚 1 和 2的生物转化。该研究产生了四种生物转化产物，包括两种氧化产物：一种羟基化衍生物 ( 3 ) 和一种羧酸衍生物 ( 4 )。此外，乙酰化（5）和酯化产物（6) 被分离出来，由内源性酵母酶进一步代谢形成。氧化转化具有高度区域选择性，并且仅发生在 C-5 烷基链的 ω 位。同源模型研究表明，只有 C-5 烷基链指向血红素，才能建立2和酶之间的最佳氢键。密切相关的 CYP4F12 不能氧化二烷基间苯二酚2。建模实验通过相对于非氧化烷基链的结合口袋的不同形状来合理化这些差异。抗菌测试表明，侧链上极性基团的存在降低了二烷基间苯二酚的抗菌活性。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。