11-Keto-β-boswellinsaeure | 17019-92-0

• 物质功能分类: 生物化工 - 中草药成分
• 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: 11-Keto-β-boswellinsaeure
• 英文别名: 11-keto-β-boswellic acid；(3R,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
• CAS: 17019-92-0
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: YIMHGPSYDOGBPI-IQQSWPBXSA-N

物化性质

• 熔点：
  190～192℃
• 沸点：
  591.8±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)
• 溶解度：
  乙醇中≤5mg/ml；DMSO 中≤25mg/ml；二甲基甲酰胺中≤25mg/ml
• LogP：
  7.100 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  29189900

制备方法与用途

生物活性

11-Keto-β-boswellic 酸（11-Keto-beta-boswellic acid）是一种五环三萜酸，来源于俗称印度乳香的乳香树（Boswellia serrata）树皮的油树脂。该物质具有显著的抗炎活性，主要通过抑制5-脂氧合酶（5-lipoxygenase；5-LOX）、白三烯、NF-κB 的激活以及肿瘤坏死因子 α （TNF-α）的产生来实现。

靶点

NF-κB
5-LOX

反应信息

• 作为反应物：
  描述：

  11-Keto-β-boswellinsaeure 在 吡啶 、 氢氧化钾 、 Jones reagent 、 silica gel 、 lithium bromide 作用下， 以 DMF (N,N-dimethyl-formamide) 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 18.5h， 生成 3,11-diketo-24-norurs-12-ene
  参考文献：
  名称：

  [EN] NOVEL ANALOGS OF 3-O-ACETYL-11-KETO-beta-BOSWELLIC ACID
  [FR] NOUVEAUX ANALOGUES DE 3-O-ACETYL-11-CETO-20051229US6534086B1KRUMHAR KIM CARLETON [US]20030318AAUS6589516B1EYRE HEATHER [GB], et al20030708AASee references of EP 1765761A4SHARMA, PHYTOTHERAPHY RESEARCH, vol. 10, 1996, pages 107 - 112SHARMAPHYTOTHERAPHY RESEARCH199610107112SAILER, E. R. ET AL., BRITISH J. PHARMACOLOGY, vol. 117, 1996, pages 615 - 618SAILER, E. R. ET AL.BRITISH J. PHARMACOLOGY1996117615618SAILER, E. R. ET AL., EURO. J. BIOCHEM., vol. 256, 1998, pages 364 - 368SAILER, E. R. ET AL.EURO. J. BIOCHEM.1998256364368YONG S. PARK, PLANTA MEDICA, vol. 68, 2002, pages 397 - 401YONG S. PARKPLANTA MEDICA200268397401HOSTANSKA. K. ET AL., ANTICANCER RES., vol. 22, no. 5, 2002, pages 2853 - 62HOSTANSKA. K. ET AL.ANTICANCER RES.2002225285362SYROVETS, T. ET AL., MOL. PHARMACOL., vol. 58, no. I, 2000, pages 71 - 81SYROVETS, T. ET AL.MOL. PHARMACOL.200058I7181HONDA, T., J. MED CHEM., vol. 43, pages 1866 - 1877HONDA, T.J. MED CHEM.4318661877

  摘要：

  这项发明涉及3-0-乙酰基-11-酮-β-乳香酸（AKBA）的类似物，具有5-脂氧合酶抑制性质。这些化合物可用于制备药物组合物，用于治疗各种炎症和基于过敏的人类疾病，包括哮喘、关节炎、溃疡性结肠炎等肠道疾病以及休克和缺血等循环障碍。这些化合物还抑制了培养中虾子的生长，这可能被视为细胞毒性和抗肿瘤活性的积极指标。

  公开号：

  WO2005123649A1
• 作为产物：
  描述：

  acetyl-11-keto-beta-boswellic acid 在 甲醇 、 氢氧化钾 、 水 作用下， 生成 11-Keto-β-boswellinsaeure
  参考文献：
  名称：

  WO2006/95355

  摘要：

  公开号：

文献信息

• Therapeutic herbal compositions for improving joint health
  申请人：Karallief, Inc.

  公开号：US11364255B2

  公开（公告）日：2022-06-21

  Compositions including herbal extracts, such as a Vitex negundo extract, a Cardiospermum halicacabum extract, and a Bambusa arundinacea extract, and methods using such compositions are disclosed. For example, compositions and methods may be used to improve joint health.

  本研究公开了包括草药提取物（如荆芥提取物、贲门失弛缓症提取物和簕杜鹃提取物）的组合物以及使用此类组合物的方法。例如，组合物和方法可用于改善关节健康。
• Compositions and Methods Comprising Boswellia Species
  申请人：Li Dan

  公开号：US20080275117A1

  公开（公告）日：2008-11-06

  In certain aspects the invention features novel compositions and pharmaceutical preparations of the same. In certain embodiments, the compositions comprise α- and/or β-boswellic acid and/or their C-acetates in an amount greater than 65% by weight.
• USES OF ANALOGS OF 3-O-ACETYL-11-KETO-BETA-BOSWELLIC ACID
  申请人：Gokaraju Ganga Raju

  公开号：US20090318551A1

  公开（公告）日：2009-12-24

  This invention relates to novel AKBA analogs of the formula I given below: Where in R 1 , R 2 , R 3 , R 4 and R 5 in each of the said analogs are: 1. R 1 ═OCHO, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 2. R 1 ═OCOCH 2 Cl, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 3. R 1 =5′-O-methylgalloyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 4. R 1 ═OCOCH 2 CH 2 COOH, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 5. R 1 =8′,9′-Dihydro-4′-hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 6. R 1 =4′-Hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 7. R 1 =3′,4′-Dimethoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ′O 8. R 1 =3′,4′-Dihydroxy-5′-methoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 9. R 1 ═OCOCH 2 NH(tert-BOC), R 2 ═H, R 3 ═COOCH 3 , R 4 & R 5 ═O 10. R 1 ═OCOCH 2 NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 11. R 1 ═OCOCH(CH 3 )NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 12. R 1 ═H, R 2 ═OH, R 3 ═COOCH 3 , R 4 & R 5 ═O 13. R 1 ═H, R 2 ═Br, R 3 ═COOCH 3 , R 4 & R 5 ═O 14. R 1 ═CN, R 2 ═H, R 3 ═COOCH 3 , R 4 & R 5 ═O 15. R 1 ═SH, R 2 ═H, R 3 ═COOCH 3 , R 4 & R 5 ═O 16. R 1 & R 2 ═N(OH), R 3 ═COOCH 3 , R 4 & R 5 ═O 17. R 1 & R 2 ═H & OCOCH 3 R 3 ═H, R 4 & R 5 ═O 18. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═COOCH 2 CH 2 N(CH 3 ) 2 , R 4 & R 5 ═O 19. R 1 ═OCOCH 3 , R 2 ═H R 3 ═CONH 2 , R 4 & R 5 ═O 20. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHNH 2 , R 4 & R 5 50 O 21. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 NH 2 , R 4 & R 5 ═O 22. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 OH, R 4 & R 5 ═O 23. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CON(CH 2 CH 2 ) 2 NH, R 4 & R 5 ═O 24. R 1 ═OCOCH 3 , R 2 ═H R 3 ═NCO, R 4 & R 5 ═O 25. R 1 ═OCOCH 3 , R 2 ═H R 3 ═NH 2 , R 4 & R 5 ═O 26. R 1 ═OCOCH 3 , R 2 ═H R 3 ═CN, R 4 & R 5 ═O 27. R 1 ═OH, R 2 ═H R 3 ═COOH, R 4 & R 5 ═OH & H These compounds exhibited 5-Lipoxigenase inhibitory properties and these compounds may be used in pharmaceutical compositions for therapeutic applications against a variety of inflammations and hypersensitivity-based human diseases including asthma, arthritis, bowel diseases such as ulcerative colitis and circulatory disorders such as shock and ischaemia. These compounds also inhibited the growth of Brine Shrimp in cultures, which may be considered as a positive indication for cytotoxicity and antitumor activity.
• TOPICAL PAIN FORMULATION
  申请人：Bennett Gary Dean

  公开号：US20110052738A1

  公开（公告）日：2011-03-03

  A topical pain formulation, comprising one or more analgesic compounds and a plurality of skin penetrants.
• Novel Salts Of Boswellic Acids And Selectively Enriched Boswellic Acids And Processes For The Same
  申请人：Gokaraju Ganga Raju

  公开号：US20130116211A1

  公开（公告）日：2013-05-09

  New salts or ion-pair complexes obtained by a reaction between boswellic acids or selectively enriched 3-O-acetyl-11-keto-β-boswellic acid (AKBA) or 11-keto-β-boswellic acid (KBA) compounds obtained through a new improved process, and an organic amine, more particularly with glucosamine. These salts or ion pair complexes are useful in nutraceuticals and in food supplements for anti-inflammatory and analgesic treatment of joints and cancer prevention or cancer therapeutic agents. These salts or ion pair complexes could also be used in cosmetic or pharmaceutical composition for external treatment of body parts or organs to treat inflammatory diseases or cancer.