6-exo-Hydroxy-(1R)-fenchone | 851210-93-0

• 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-Hydroxy-(1R)-fenchone
• 英文别名: 6-exo-hydroxyfenchone；6-exo-Hydroxyfenchone；(1S,4R,6S)-6-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 851210-93-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: RBJVDSYEMJHFOC-BYULHYEWSA-N

物化性质

• 沸点：
  250.9±23.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 生成 6-exo-Hydroxy-(1R)-fenchone
  参考文献：
  名称：

  Mikrobiologische Umwandlung von bicyclischen Monoterpenen durchAbsidia orchidis(VUILL.)HAGEM. 2. Teil. Hydroxylierung von Fenchon und Isofenchon. 18. Mitteilung über Reaktionen mit Mikroorganismen [1]

  摘要：

  Abstract(+)‐Fenchone (3a) was transformed to 6‐exo‐hydroxy‐fenchone (6β‐hydroxy‐1, 3, 3‐trimethyl‐nor‐bornan‐2‐one) (1a) and to 5‐exo‐hydroxy‐fenchone 5β‐hydroxy‐1, 3, 3‐trimethyl‐nor‐bornan‐2‐one (4a) by the mycelium of Absidia orchidis (Vuill.) Hagem. The structure of the two products was proven by a detailed analysis of the NMR. spectra of the corresponding acetyl derivatives 2a and 5a respectively, and by CrO3‐oxidation. 1a yielded the β‐diketone 6a, and 4a the diketone 8a. Whereas 8a was stable to alkali 6a was cleaved to the cyclopentane carboxylic acids 7 and 9. — Incubation of (—)‐fenchone (3b) yielded the enantiomeric hydroxylation products 1b and 4b in the same ratio. ‐ (—)‐Isofenchone (11a) was transformed by Absidia orchidis into the two epimers 6‐endo‐hydroxy‐isofenchone (6β‐hydroxy‐1, 5, 5‐trimethyl‐nor‐bornan‐2‐one) (12a) and 6‐exo‐hydroxy‐isofenchone (6β‐hydroxy‐1, 5, 5‐trimethyl‐nor‐bornan‐2‐one) (10a.) CrO3‐oxidation of both 10a and 12a gave the same β‐diketone 6a. ‐ (+)‐Isofenchone gave the corresponding enantiomeric hydroxy derivatives 10b and 12b on incubation with Absidia orchidis.

  DOI：

  10.1002/hlca.19690520622

文献信息

• Metabolism of (<b>−</b>)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes
  作者：M. Miyazawa、K. Gyoubu

  DOI：10.1080/00498250600917256

  日期：2007.2

  The in vitro metabolism of (-)-fenchone was examined in human liver microsomes and recombinant enzymes. The biotransformation of (-)-fenchone was investigated by gas chromatography-mass spectrometry. (-)-Fenchone was found to be oxidized to 6-exo-hydroxyfenchone, 6-endo-hydroxyfenchone and 10-hydroxyfenchone by human liver microsomal P450 enzymes. The formation of metabolites was determined by the relative abundance of mass fragments and retention times on gas chromatography (GC). CYP2A6 and CYP2B6 were major enzymes involved in the hydroxylation of (-)-fenchone by human liver microsomes, based on the following lines of evidence. First, of 11 recombinant human P450 enzymes tested, CYP2A6 and CYP2B6 catalysed the oxidation of (-)-fenchone. Second, oxidation of (-)-fenchone was inhibited by thioTEPA and (+)-menthofuran. Finally, there was a good correlation between CYP2A6, CYP2B6 contents and (-)-fenchone hydroxylation activities in liver microsomes of 11 human samples. CYP2A6 may be more important than CYP2B6 in human liver microsomes. Kinetic analysis showed that the V-max/K-m values for (-)fenchone 6-endo-, 6-exo- and 10-hydroxylation catalysed by liver microsomes of human sample HG-03 were 24.3, 44.0 and 1.3nM(-1) min(-1), respectively. Human recombinant CYP2A6 and CYP2B6 catalysed (-)-fenchone 6-exo-hydroxylation with V-max values of 2.7 and 12.9 nmol min(-1) nmol(-1) P450 and apparent K-m values of 0.18 and 0.15 mM and (-)-fenchone 6-endo-hydroxylation with Vmax values of 1.26 and 5.33 nmol min(-1) nmol(-1) P450 with apparent K. values of 0.29 and 0.26 mM. (-)-Fenchone 10-hydroxylation was catalysed by CYP2B6 with K-m and V-max values of 0.2mM and 10.66 nmol min(-1) nmol(-1) P450, respectively.
• Mikrobiologische Umwandlung von bicyclischen Monoterpenen durch<i>Absidia orchidis</i>(V<scp>UILL</scp>.)<scp>HAGEM</scp>. 2. Teil. Hydroxylierung von Fenchon und Isofenchon. 18. Mitteilung über Reaktionen mit Mikroorganismen [1]
  作者：B. Pfrunder、Ch. Tamm

  DOI：10.1002/hlca.19690520622

  日期：——

  Abstract(+)‐Fenchone (3a) was transformed to 6‐exo‐hydroxy‐fenchone (6β‐hydroxy‐1, 3, 3‐trimethyl‐nor‐bornan‐2‐one) (1a) and to 5‐exo‐hydroxy‐fenchone 5β‐hydroxy‐1, 3, 3‐trimethyl‐nor‐bornan‐2‐one (4a) by the mycelium of Absidia orchidis (Vuill.) Hagem. The structure of the two products was proven by a detailed analysis of the NMR. spectra of the corresponding acetyl derivatives 2a and 5a respectively, and by CrO3‐oxidation. 1a yielded the β‐diketone 6a, and 4a the diketone 8a. Whereas 8a was stable to alkali 6a was cleaved to the cyclopentane carboxylic acids 7 and 9. — Incubation of (—)‐fenchone (3b) yielded the enantiomeric hydroxylation products 1b and 4b in the same ratio. ‐ (—)‐Isofenchone (11a) was transformed by Absidia orchidis into the two epimers 6‐endo‐hydroxy‐isofenchone (6β‐hydroxy‐1, 5, 5‐trimethyl‐nor‐bornan‐2‐one) (12a) and 6‐exo‐hydroxy‐isofenchone (6β‐hydroxy‐1, 5, 5‐trimethyl‐nor‐bornan‐2‐one) (10a.) CrO3‐oxidation of both 10a and 12a gave the same β‐diketone 6a. ‐ (+)‐Isofenchone gave the corresponding enantiomeric hydroxy derivatives 10b and 12b on incubation with Absidia orchidis.