28-去甲齐墩果-12-烯-3-酮 | 73493-60-4

• 物质功能分类: 生物化工 - 提取物
• 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: 28-去甲齐墩果-12-烯-3-酮
• 中文别名: 28-去甲基-Β-香树脂酮
• 英文名称: 3-oxo-28-norolean-12-ene
• 英文别名: 28-norolean-12-en-3-one；3-oxo-28-norolean-12-en；28-Demethyl-beta-amyrone；(4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,4a,5,6,7,8,8a,9,10,12,12a,14,14a-tetradecahydropicen-3-one
• CAS: 73493-60-4
• 化学式: C₂₉H₄₆O
• 分子量: 410.684
• InChiKey: QQKXTWZLGUEVGX-DICJWPJSSA-N

物化性质

• 沸点：
  484.4±45.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

制备方法与用途

用途

去甲基-β-香树脂酮（28-Norolean-12-en-3-one）是一种三萜类化合物，可用于结构改造，并可作为化工和医药中间体。

制备

将β-香树脂醇（100 mg，1.0 eq）溶解在二氯甲烷（DCM，20.0 mL）中并冷却至0℃。随后加入过氧化苯甲酰（PCC，76 mg，1.5 eq），并将混合物在室温下搅拌1小时。通过薄层色谱（TLC，己烷：乙酸乙酯 6:1）监测反应进程。将反应液浓缩于硅胶上，并使用柱色谱法纯化，以己烷：乙酸乙酯（60:1至20:1）为洗脱剂，得到纯净的去甲基-β-香树脂酮（28-Norolean-12-en-3-one），重量为63 mg。

生物活性

28-去甲基-β-香树脂酮是黄连木的主要三萜之一。它具有抗毒素作用，能够有效对抗葡萄球菌肠毒素（SEs）的毒性效应。

反应信息

• 作为产物：
  描述：

  (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 在 吡啶 、 chromium(VI) oxide 、 Wilkinson's catalyst 、 lithium aluminium tetrahydride 、 苯甲腈 作用下， 生成 28-去甲齐墩果-12-烯-3-酮
  参考文献：
  名称：

  Photochemical or photomimetic fossil triterpenoids in sediments and petroleum

  摘要：

  DOI：

  10.1021/ja00523a048

文献信息

• TERPENE ENRICHED FRACTIONS FREE FROM POLYTERPENES EXTRACTED FROM CHIOS MASTIC GUM AND COSMETIC, NUTRACEUTICAL, MEDICAL DEVICES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Phytoitalia SRL

  公开号：EP3363448A1

  公开（公告）日：2018-08-22

  The invention relates to isolated fractions of Chios mastic gum enriched in terpene monomers and oligomers and substantially free of poly-terpene polymers with a degree of polymerization greater than 8 and a molecular weight in the range from about 1,000 to about 100,000 as well as to a process for their preparation. The invention also relates to compositions comprising an isolated fraction of monomeric and oligomeric terpenes extracted and purified by reverse-phase chromatography and essentially free of polymers. The monomeric and oligomeric enriched terpenes fraction obtained from Chios mastic gum exhibits biological activities in cosmetic, nutraceutical, medical devices and pharmaceutical applications.

  本发明涉及富含萜烯单体和低聚物且基本上不含聚合度大于 8、分子量在约 1,000 至约 100,000 范围内的多萜烯聚合物的奇奥斯胶分离馏分，以及制备它们的工艺。本发明还涉及一种组合物，该组合物包含通过反相色谱法提取和纯化的单体萜烯和低聚萜烯的分离部分，基本上不含聚合物。从希俄斯胶astic gum 中获得的单体和低聚富集萜烯部分在化妆品、营养品、医疗器械和药物应用中具有生物活性。
• [EN] TERPENE ENRICHED FRACTIONS FREE FROM POLYTERPENES EXTRACTED FROM CHIOS MASTIC GUM AND COSMETIC, NUTRACEUTICAL, MEDICAL DEVICES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] FRACTIONS ENRICHIES EN TERPÈNE EXEMPTES DE POLYTERPÈNES EXTRAITES DE GOMME DE MASTIC DE CHIOS ET DISPOSITIFS COSMÉTIQUES, NUTRACEUTIQUES, MÉDICAUX ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：PHYTOITALIA SRL

  公开号：WO2019170239A1

  公开（公告）日：2019-09-12

  The invention relates to isolated fractions of Chios mastic gum enriched in terpene monomers and oligomers and substantially free of poly-terpene polymers with a degree of polymerization greater than 8 and a molecular weight in the range from about 1,000 to about 100,000 as well as to a process for their preparation. The invention also relates to compositions comprising an isolated fraction of monomeric and oligomeric terpenes extracted and purified by reverse-phase chromatography and essentially free of polymers. The monomeric and oligomeric enriched terpenes fraction obtained from Chios mastic gum exhibits biological activities in cosmetic, nutraceutical, medical devices and pharmaceutical applications.