丹参酚酮 | 120278-22-0

• 物质功能分类: 有机原料 - 酮类化合物
• 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
• 中文名称: 丹参酚酮
• 英文名称: (S)-2,3,4,4a-tetrahydro-5,6-dihydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-9(1H)-phenanthrenone
• 英文别名: 6-hydroxysalvinolone；salvinolone；(4aS)-5,6-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4-dihydro-2H-phenanthren-9-one
• CAS: 120278-22-0
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: NPADGWOASIJKSB-FQEVSTJZSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 丹参酚酮 在 吡啶 作用下， 以80%的产率得到diacetyl-salvinolone
  参考文献：
  名称：

  鼠尾草二萜

  摘要：

  摘要 从丹参的根中分离出两种新的二萜类化合物，salvinolone 和 Salvinolactone，以及两种 4,5-seco-5,10-friedo-abietane 二萜类化合物，4-hydroxy sapriparquinone 和 saprorthoquinone，并在此基础上阐明了它们的结构。他们的 1H 和 13C 核磁共振谱。

  DOI：

  10.1016/0031-9422(89)85033-2
• 作为产物：
  描述：

  12-benzoyloxy-11-hydroxyabieta-8,11,13-triene 在 chromium(VI) oxide 、 磺酰氯 、 对甲苯磺酸 、 lithium chloride 作用下， 以 吡啶 、 四氯化碳 、 溶剂黄146 、 甲苯 为溶剂， 反应 63.0h， 生成 丹参酚酮
  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

文献信息

• Diterpenes of Salvia prionitis
  作者：Long-Ze Lin、Gabor Blaskó、Geoffrey A. Cordell

  DOI：10.1016/0031-9422(89)85033-2

  日期：——

  Abstract From the roots of Salvia prionitis Hance two new diterpenoids, salvinolone and salvinolactone, and two 4,5-seco-5,10-friedo-abietane diterpenoids, 4-hydroxy sapriparquinone and saprorthoquinone, have been isolated and their structures elucidated on the basis of their 1H and 13C NMR spectra.

  摘要 从丹参的根中分离出两种新的二萜类化合物，salvinolone 和 Salvinolactone，以及两种 4,5-seco-5,10-friedo-abietane 二萜类化合物，4-hydroxy sapriparquinone 和 saprorthoquinone，并在此基础上阐明了它们的结构。他们的 1H 和 13C 核磁共振谱。
• LIN, LONG-ZE;BLASKO, GABOR;CORDELL, GEOFFREY A., PHYTOCHEMISTRY, 28,(1989) N 1, C. 177-181
  作者：LIN, LONG-ZE、BLASKO, GABOR、CORDELL, GEOFFREY A.

  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.
• The Synthesis of Salvinolone, Saprorthoquinone, and 4-Hydroxysapriparaquinone from (+)-Dehydroabietic Acid
  作者：Takashi Matsumoto、Yasutaka Tanaka、Hiromitsu Terao、Yoshio Takeda、Makoto Wada

  DOI：10.1246/bcsj.66.3053

  日期：1993.10

  Salvinolone, saprorthoquinone, and 4-hydroxysapriparaquinone isolated from the roots of Salvia prionitis Hance. were synthesized starting from (+)-dehydroabietic acid via 11,12-dimethoxyabieta-8,11,13-trien-7-one and 12-methoxyabieta-8, 11,13-triene.

  从 Salvia prionitis Hance 的根中分离出 Salvinolone、saprorthoquinone 和 4-hydroxysapriparaquinone。由 (+)-脱氢枞酸通过 11,12-二甲氧基松香-8,11,13-trien-7-one 和 12-甲氧基松香-8, 11,13-triene 合成。