6-exo-hydroxycamphor

• 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: 6-exo-hydroxycamphor
• 英文别名: (+)-6-Exo-hydroxycamphor；(1S,4R,6S)-6-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: UNOCSJVDJYDPTN-FWWHASMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-endo-hydroxycamphor 以 氘代氯仿 为溶剂， 生成 6-exo-hydroxycamphor
  参考文献：
  名称：

  Multiple Monohydroxylation Products from rac-Camphor by Marine Fungus Botryosphaeria sp. Isolated from Marine Alga Bostrychia radicans

  摘要：

  This manuscript describes the biooxidation of rac-camphor using whole cells of marine-derived fungus Botryosphaeria sp. CBMAI 1197. The main biotransformation products of this monoterpene were achieved via a hydroxylation reaction and occurred with 5 days of rac-camphor incubation. Products were identified by means of gas chromatography mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) data. The major hydroxylated products were 6-endo-hydroxycamphor, 6-exo-hydroxycamphor, 5-exo-hydroxycamphor, 5-endo-hydroxycamphor, 3-exo-hydroxycamphor and 8-hydroxycamphor. The 6-exo-hydroxycamphor was obtained through a retro-aldol reaction when 6-endo-hydroxycamphor was maintained in presence of CDCl3; this isomerization was confirmed by H-1 NMR and GC-MS data.

  DOI：

  10.21577/0103-5053.20160262

文献信息

• Induction and Characterization of a Cytochrome P-450-Dependent Camphor Hydroxylase in Tissue Cultures of Common Sage (Salvia officinalis)
  作者：C. Funk、R. Croteau

  DOI：10.1104/pp.101.4.1231

  日期：1993.4.1

  oil of common sage (Salvia officinalis), is catabolized in senescent tissue, and the pathway for the breakdown of this bicyclic ketone has been previously elucidated in sage cell-suspension cultures. In the initial step of catabolism, camphor is oxidized to 6-exo-hydroxycamphor, and the corresponding NADPH- and O2-dependent hydroxylase activity was demonstrated in microsomal preparations of sage cells

  （+）-Camphor是普通鼠尾草（Salvia officinalis）的主要单萜，在衰老组织中被分解代谢，这种双环酮的分解途径先前已在鼠尾草细胞悬浮培养物中得到阐明。在分解代谢的初始步骤中，樟脑被氧化成6-exo-羟基樟脑，并且在鼠尾草微粒体制剂中证明了相应的NADPH和O2依赖性羟化酶活性。几种完善的细胞色素P-450依赖性反应抑制剂，包括细胞色素c，克霉唑和CO，均抑制樟脑的羟基化，蓝光可部分逆转CO依赖性抑制作用。用30 mM MnCl2处理鼠尾草悬浮培养物后，樟脑6-羟化酶活性被诱导多达7倍。来自鼠尾草微粒体膜的估计分子量为58 kD的多肽在Western blot实验中显示出抗原交叉反应性，其中两种异源多克隆抗体针对恶臭假单胞菌的细胞色素P-450樟脑-5-外切羟化酶和细胞色素P-450柠檬烯-留兰香（Mentha spicata）的6S-羟化酶。点印迹表明该多肽的浓度随Mn2
• Catabolism of camphor in tissue cultures and leaf disks of common sage (Salvia officinalis)
  作者：Christoph Funk、Alfred E. Koepp、Rodney Croteau

  DOI：10.1016/0003-9861(92)90173-t

  日期：1992.4

  accumulated in the leaves of common sage (Salvia officinalis), and as the plant approaches maturity the content of this monoterpene ketone decreases by roughly half. Although the ability to catabolize camphor has been demonstrated previously in sage leaf disks, tissue cultures proved to be a more suitable system for examining the responsible degradative pathway. Cell suspension cultures were shown to convert

  （+）-樟脑占普通鼠尾草（Salvia officinalis）叶片中积累的单萜的近30％，随着植物成熟，该单萜酮的含量大约减少一半。尽管先前已在鼠尾草叶盘中证明了分解樟脑的能力，但组织培养被证明是一种更合适的系统，用于检查负责任的降解途径。显示细胞悬浮培养物将（+）-[3-3H2]樟脑依次转化为6-羟基樟脑，6-氧樟脑樟脑，α-樟脑酸和2-羟基-α-樟脑酸，以及每个通过色谱和光谱学方法鉴定途径。该氧化性开环序列类似于土壤白喉类，分枝杆菌，最终导致等位代脂体成为最后定义的代谢产物，其中包含原始双环核的所有10个碳。对细胞培养物和叶盘的研究还表明，樟脑通过1，2-樟脑（一种先前描述的鼠尾草叶中的代谢物）的分解代谢是次要的降解途径。在培养的鼠尾草细胞的无细胞提取物中证明了樟脑代谢的第一步，几条证据表明，这种微粒体（+）-樟脑6-外切羟化酶是细胞色素P-450依赖的单加氧酶。是次要的降解途径。在
• Molecular recognition in cytochrome P-450: alteration of regioselective alkane hydroxylation via protein engineering
  作者：William M. Atkins、Stephen G. Sligar

  DOI：10.1021/ja00189a057

  日期：1989.3