紫苏酮 | 142546-15-4

• 物质功能分类: 天然产物 - 萜类
• 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: 紫苏酮
• 英文名称: sageone
• 英文别名: 11,12-dihydroxy-20-norabieta-5(10),8,11,13-tetraen-1-one；5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,9,10-tetrahydrophenanthren-4-one
• CAS: 142546-15-4
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: NPQAMUFQEFLLCY-UHFFFAOYSA-N

物化性质

• 沸点：
  485.9±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 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)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  紫苏酮 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 以1.2 mg的产率得到1-oxomiltirone
  参考文献：
  名称：

  Diterpenes from Salvia mellifera and their biogenetic significance

  摘要：

  The new diterpenes, 11,12-dihydroxy-20-nor-abieta-5(10),8,11,13-tetraen-1-one and isogaldosol, together with the known compounds carnosic acid, carnosol, rosmanol, rosmadial, galdosol and isorosmanol were isolated from the aerial part of Salvia mellifera. The structures of the new diterpenes were established from their spectral data and by chemical correlations. The co-occurrence of all these compounds in one species taken together with their chemical behaviour led to the postulation of a biogenetic pathway to highly oxidized abietatriene diterpenes in which enzymatic dehydrogenation processes and the participation of singlet-state oxygen appear to play an important role.

  DOI：

  10.1016/0031-9422(92)80282-j
• 作为产物：
  描述：

  5,6-Dimethoxy-1,1-dimethyl-7-propan-2-yl-2,3,9,10-tetrahydrophenanthren-4-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到紫苏酮
  参考文献：
  名称：

  Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone

  摘要：

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

  DOI：

  10.1021/jo970570q

文献信息

• Use of tricyclic diterpenes and their derivatives for the treatment, co-treatment or prevention of inflammatory disorders and/or joint disorders
  申请人：DSM IP Assets B.V.

  公开号：EP1925301A1

  公开（公告）日：2008-05-28

  The present invention refers to the use of at least one tricyclic diterpenes for the manufacture of a cosmetic, nutraceutical or pharmaceutical for the treatment, co-treatment or prevention of inflammatory disorders and/or joint disorders. More particularly, the compounds are selected from 7-oxodehydroabietic acid, totarol, hydroxytotarol, totarol-19-carboxylic acid methyl ester, sageone, 8,11,13-abietatriene-11,12,20-triol, royleanonic acid, ferruginol, carnosic acid 12-methylether and 7-methylrosmanol.

  本发明是指将至少一种三环二萜用于制造治疗、辅助治疗或预防炎症性疾病和/或关节疾病的化妆品、营养品或药品。更具体地说，这些化合物选自 7-氧代脱氢松香酸、土他洛尔、羟基土他洛尔、土他洛尔-19-羧酸甲酯、鼠尾草酮、8,11,13-松香三烯-11,12,20-三醇、花叶酸、阿魏酰醇、肉豆蔻酸 12-甲基醚和 7-甲基rosmanol。
• USE OF TRICYCLIC DITERPENES AND THEIR DERIVATIVES FOR THE TREATMENT, CO-TREATMENT OR PREVENTION OF INFLAMMATORY DISORDERS AND/OR JOINT DISORDERS
  申请人：Raederstorff Daniel

  公开号：US20100056615A1

  公开（公告）日：2010-03-04

  The present invention refers to the use of at least one tricyclic diterpenes for the manufacture of a nutraceutical or pharmaceutical for the treatment, co-treatment or prevention of inflammatory disorders and/or joint disorders.
• [EN] USE OF TRICYCLIC DITERPENES AND THEIR DERIVATIVES FOR THE TREATMENT, CO-TREATMENT OR PREVENTION OF INFLAMMATORY DISORDERS AND/ OR JOINT DISORDERS<br/>[FR] UTILISATION DE DITERPÈNES TRICYCLIQUES ET LEURS DÉRIVÉS POUR LE TRAITEMENT, LE COTRAITEMENT OU LA PRÉVENTION DE TROUBLES INFLAMMATOIRES ET/OU TROUBLES DES ARTICULATIONS
  申请人：DSM IP ASSETS BV

  公开号：WO2008061720A2

  公开（公告）日：2008-05-29

  [EN] The present invention refers to the use of at least one tricyclic diterpenes for the manufacture of a nutraceutical or pharmaceutical for the treatment, co-treatment or prevention of inflammatory disorders and/ or joint disorders.
  [FR] La présente invention concerne l'utilisation d'au moins un diterpène tricyclique pour la fabrication d'un médicament ou d'un alicament pour le traitement, le cotraitement ou la prévention des troubles inflammatoires et/ou des troubles des articulations.
• Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone
  作者：George Majetich、Shuang Liu、Jing Fang、David Siesel、Yong Zhang

  DOI：10.1021/jo970570q

  日期：1997.10.1

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.
• Diterpenes from Salvia mellifera and their biogenetic significance
  作者：Antonio G González、Lucia S Andrés、Zahira E Aguiar、Javier G Luis

  DOI：10.1016/0031-9422(92)80282-j

  日期：1992.4

  The new diterpenes, 11,12-dihydroxy-20-nor-abieta-5(10),8,11,13-tetraen-1-one and isogaldosol, together with the known compounds carnosic acid, carnosol, rosmanol, rosmadial, galdosol and isorosmanol were isolated from the aerial part of Salvia mellifera. The structures of the new diterpenes were established from their spectral data and by chemical correlations. The co-occurrence of all these compounds in one species taken together with their chemical behaviour led to the postulation of a biogenetic pathway to highly oxidized abietatriene diterpenes in which enzymatic dehydrogenation processes and the participation of singlet-state oxygen appear to play an important role.