卫矛酮 | 50802-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 卫矛酮
• 英文名称: tingenone
• 英文别名: maitenin；maytenin；Tingenon；(6aS,6bS,8aS,11R,12aR,14aR)-3-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione
• CAS: 50802-21-6
• 化学式: C₂₈H₃₆O₃
• 分子量: 420.592
• InChiKey: WSTYNZDAOAEEKG-GWJSGULQSA-N

物化性质

• 熔点：
  203.5°C
• 沸点：
  477.74°C (rough estimate)
• 密度：
  1.0906 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  卫矛酮 在 platinum(IV) oxide 氢气 作用下， 生成 (2R,4aS,6aS,12bS,14aS,14bR)-10,11-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,4,4a,5,6,6a,8,12b,13,14,14a,14b-dodecahydro-2H-picen-3-one
  参考文献：
  名称：

  来自 Maytenus canariensis 的抗生素酚去甲三萜

  摘要：

  从 Maytenus canariensis 的根皮中分离出新的酚类 6-oxo-tingenol、3-O-methyl-6-oxo-tingenol 和 6-oxo-iguesterol。它们的结构由 1H 和 13C NMR 光谱研究确定，包括 HMQC、HMBC、DEPT 和 ROESY 以及化学转化。6-oxo-tingenol 的合成是由 tingenone 实现的。这些化合物对革兰氏阳性菌表现出抗生素活性。

  DOI：

  10.1016/0031-9422(96)00205-1

文献信息

• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS
  申请人：Qian Xiangping

  公开号：US20120052019A1

  公开（公告）日：2012-03-01

  Chemical entities which are triterpenoid derivatives, pharmaceutical compositions and methods of treatment of inflammatory, neurodegenerative, neoplastic and autoimmune diseases are described.

  本文描述了三萜类衍生物、制药组合物以及治疗炎症、神经退行性、肿瘤和自身免疫性疾病的方法。
• Iguesterin, a new quinonoid triterpene from Catha cassinoides
  作者：Antonio G. González、Cosme G. Francisco、Raimundo Freire、Rosendo Hernández、José A. Salazar、Ernesto Suárez

  DOI：10.1016/0031-9422(75)85188-0

  日期：1975.4

  Abstract β-Amyrin, sitosterol, celastrol, pristimerin, tingenone and a new hydroxymethylene quinonoid dinor-triterpene iguesterine were isolated from the root bark of Catha cassinoides. The structure of iguesterine was determined spectroscopically and by synthesis from tingenone. Tentative assignments are given for the chemical shifts of the methyl groups of iguesterin, tingenone and some of their derivatives

  摘要 从苦参的根皮中分离得到β-香树脂醇、谷甾醇、celastrol、pristimerin、tingenone和一种新的羟基亚甲基醌二诺-三萜烯雌二醇。iguesterine 的结构是通过光谱法和由丁酮合成确定的。对伊格雌激素、丁酮及其一些衍生物的甲基的化学位移给出了初步的分配。
• Two new triterpene dimers from Celastraceae, their partial synthesis and antimicrobial activity
  作者：Antonio G. González、JoséS. Jiménez、Laila M. Moujir、Angel G. Ravelo、Javier G. Luis、Isabel L. Bazzocchi、Angel M. Gutiérrez

  DOI：10.1016/s0040-4020(01)88136-9

  日期：——

  Two new triterpene dimers, 7 and 8, were isolated from Maytenus umbellata and proved to be oxidized structures of tingenone from which they could also be synthesized. These compounds were screened for antimicrobial activity and compared with related compounds.

  从五倍体Maytenus umbellata分离出两个新的三萜二聚体7和8，它们被证明是丁烯酮的氧化结构，也可以由它们合成。筛选这些化合物的抗微生物活性，并与相关化合物进行比较。
• Oxidation of natural targets by dimethyl dioxirane: Regio and stereospecific reactions on enol double bond of bioactive nor quinone methide triterpenes
  作者：Antonio G. González、Nelson L. Alvarenga、Ana Estévez-Braun、Angel G. Ravelo、Rafael Estévez-Reyes

  DOI：10.1016/0040-4020(96)00588-1

  日期：1996.8

  Nor quinone methide triterpenes, like pristimerin and tingenone, possess one enol double bond (C3–C4). They also have an extended conjugation with an additional double bond (C7–C8). When these compounds are treated with dimethyl dioxirane, regio and stereoespecific oxidation occurs only on the enol double bond.

  甲基苯醌三萜烯，如普里司特林和丁香酮，也没有一个烯醇双键（C 3 –C 4）。它们还具有额外的双键（C 7 –C 8）扩展的共轭。当这些化合物用二甲基二环氧乙烷处理时，区域和立体特异性氧化仅在烯醇双键上发生。
• Antimicrobial Activity and Stability of Tingenone Derivatives
  作者：Uthai Sotanaphun、Vimolmas Lipipun、Rutt Suttisri、Rapepol Bavovada

  DOI：10.1055/s-2006-960809

  日期：1999.6

  Quinone-methide triterpenes of the tingenone series were evaluated for their antimicrobial activity. These compounds were effective against Bacillus cereus, B. subtilis, Sarcinalutea, Staphylococcus aureus, Microsporum gypseum and a Gramnegative bacterium, Klebsiella pneumoniae. Under acidic conditions, the quinone-methide part of these compounds rear ranged into the divinyl-phenolic system, and the antimicrobial activity was thus lost.

  对丁烯酮系列的醌-甲醚三萜类化合物的抗菌活性进行了评估。这些化合物对蜡样芽孢杆菌、枯草杆菌、沙氏杆菌、金黄色葡萄球菌、石膏样小孢子菌和革兰氏阴性菌肺炎克雷伯氏菌有效。在酸性条件下，这些化合物中的醌-甲酰胺部分重新变成了二乙烯基-酚系统，从而失去了抗菌活性。