6β-hydroxyferruginol | 70614-90-3

• 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: 6β-hydroxyferruginol
• 英文别名: ferruginol；(4bS,8aS,9R)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-3,9-diol
• CAS: 70614-90-3
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: XEJHUBFVQWSNJW-WSTZPKSXSA-N

物化性质

• 熔点：
  173-175.5 °C(Solvent: Hexane)
• 沸点：
  427.0±45.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  6β-hydroxyferruginol 在 lithium aluminium tetrahydride 、 jones reagent 作用下， 以 四氢呋喃 、 氯仿 、 丙酮 为溶剂， 反应 49.58h， 生成 落羽松二酮
  参考文献：
  名称：

  Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

  摘要：

  Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6 beta -hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 mug/mL of MIC against MRSA and 4-16 mug/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 mug/mL of MIC against both MRSA and VRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00253-4
• 作为产物：
  描述：

  (4bS,8aS)-4b,6,7,8,8a,10-hexahydro-3-methoxy-4b,8,8-trimethyl-2-(1-methylethyl)phenanthren-9(5H)-one 在 lithium aluminium tetrahydride 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 6β-hydroxyferruginol
  参考文献：
  名称：

  Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

  摘要：

  Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6 beta -hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 mug/mL of MIC against MRSA and 4-16 mug/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 mug/mL of MIC against both MRSA and VRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00253-4

文献信息

• Diterpenes from the Heartwood of Juniperus formosana HAY. var. concolr HAY.
  作者：Yueh-Hsiung KUO、Ming-Tsang YU

  DOI：10.1248/cpb.44.1431

  日期：——

  Three was diterpenes, 6β-hydroxyferruginol (1a), formosaninol (2a), and formosanin (2b), were isolated from the heartwood of Juniperus formosana HAY. var. concolor HAY. The structure of formosaninol was deduced to be a dimeric ferruginol with 6-O-7' and 7-O-6' linkages on the basis of spectroscopic analysis and chemical evidence. Formosanin was a dimethyl ether of formosaninol. 6α-Hydroxy-7-oxoferruginol can be converted to 6α- and 6β-hydroxyferruginols, 6-oxoferruginol and formosaninol by lithium aluminum hydride reduction and acidification. The structure of 6β-hydroxyferruginol isolated from Cryptomeria japonica was revised to 6α-hydroxyferruginol.

  从杜松（Juniperus formosana HAY. var. concolor HAY）的心材中分离出了三种二萜，即 6β-hydroxyferruginol (1a)、formosaninol (2a) 和 formosanin (2b)。根据光谱分析和化学证据，推断出福尔马林醇的结构是一种具有 6-O-7' 和 7-O-6' 连接的二聚铁杉醇。福尔马林是福尔马林醇的二甲醚。6α-Hydroxy-7-oxoferruginol 可通过氢化铝锂还原和酸化转化为 6α- 和 6β-hydroxyferruginols、6-oxoferruginol 和 formosaninol。从隐花中分离出的 6β-hydroxyferruginol 的结构被修正为 6α-hydroxyferruginol 。
• Haslinger, Ernst; Michl, Guenter, Liebigs Annalen der Chemie, 1989, p. 677 - 686
  作者：Haslinger, Ernst、Michl, Guenter

  DOI：——

  日期：——
• 6-Oxoferruginol and 6α-Acetoxyferruginol, New Abietane-Type Diterpenes from the Heartwood of <i>Juniperus formosana</i>
  作者：Yueh-Hsiung Kuo、Ming-Tsang Yu

  DOI：10.1021/np960389x

  日期：1997.6.1

  New abietane diterpenes, 6 alpha-acetoxyferruginol and 6-oxoferruginol were isolated from the heartwood of Juniperus formosana Hay. var. concolor Hay. together with the known compounds ferruginol, sugiol, xanthoperol, 5-epi-xanthoperol, and 6,12-'dihydroxyabieta-5,8,11,13-tetraen-7-one. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence.
• HASLINGER, ERNST;MICHL, GUNTER, LIEBIGS ANN. CHEM.,(1989) N, C. 677-686
  作者：HASLINGER, ERNST、MICHL, GUNTER

  DOI：——

  日期：——
• Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE
  作者：Zhixiang Yang、Yoshikazu Kitano、Kazuhiro Chiba、Naohiro Shibata、Hiroshi Kurokawa、Yohei Doi、Yoshichika Arakawa、Masahiro Tada

  DOI：10.1016/s0968-0896(00)00253-4

  日期：2001.2

  Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6 beta -hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 mug/mL of MIC against MRSA and 4-16 mug/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 mug/mL of MIC against both MRSA and VRE. (C) 2001 Elsevier Science Ltd. All rights reserved.