乳香酸 | 471-66-9

• 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: 乳香酸
• 中文别名: Alpha-乳香酸；α-乳香酸；Α-乳香酸；alpha-乳香酸
• 英文名称: alpha-Boswellic acid
• 英文别名: α-boswellic acid；(3R,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• CAS: 471-66-9
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: BZXULBWGROURAF-IKNLXHIFSA-N

物化性质

• 熔点：
  289℃
• 沸点：
  552.7±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）
• LogP：
  9.430 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  29181990

制备方法与用途

生物活性

α-boswellic acid（α-博紫杉烯酸）是一种五环三萜类化合物，从乳香中提取，具有抗惊厥和抗癌活性。研究显示，α-boswellic acid可在动物体内预防并减少阿尔茨海默病标志物的产生，可用于阿尔茨海默病的研究。

化学性质

α-boswellic acid可溶于甲醇、乙醇及DMSO等有机溶剂，来源于乳香。

用途

该化合物具有抗炎和抗肿瘤作用，并广泛用于含量测定、鉴定以及药理实验。

药理药效

α-boswellic acid能够调节畜禽胃肠道酸度，抑制病原菌的生长与繁殖，减少腹泻；同时提高胃蛋白酶和十二指肠胰蛋白酶活性及肠道有益微生物活性，促进营养物质消化吸收完全。

反应信息

• 作为反应物：
  描述：

  乳香酸 280.0~300.0 ℃ 、93.33 Pa 条件下， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Trost, Annali di Chimica Applicata, 1937, vol. 27, p. 178,185

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰基-alpha-乳香酸 在 氢氧化钾 作用下， 生成 乳香酸
  参考文献：
  名称：

  Winterstein; Stein, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1932, vol. 208, p. 10

  摘要：

  DOI：

文献信息

• First partial synthesis of α-boswellic acid from oleanolic acid
  作者：Oliver Kraft、Immo Serbian、Ahmed Al-Harrasi、René Csuk

  DOI：10.1016/j.phytol.2022.10.007

  日期：2022.12

  While β-boswellic acid is very readily available by extraction from frankincense resin, the accessibility of α-boswellic from the resin involved great effort and tedious purification procedures. Alternatively, a partial synthesis from readily available oleanolic acid was developed, the key steps of which are a reduction of the carboxyl group C-28 furnishing a methyl group, followed by palladium-assisted

  虽然从乳香树脂中提取 β-乳香酸很容易获得，但从树脂中提取 α-乳香酸需要付出巨大的努力和繁琐的纯化程序。或者，开发了一种从容易获得的齐墩果酸进行部分合成的方法，其关键步骤是还原羧基 C-28 以提供甲基，然后是甲基 C-24 的钯辅助氧化，以及构型反转在 C-3。
• PENTACYCLIC TRITERPENOIDS FOR INJECTION LIPOLYSIS
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP3124047A1

  公开（公告）日：2017-02-01

  The present invention relates to a composition comprising a pentacyclic triterpenoid compound or a pharmaceutically acceptable salt thereof, and at least one further component C for use in a method for local treating or preventing a condition associated with an undesired local subcutaneous fat deposit in a mammal, wherein said compound is injected into said local subcutaneous fat deposit aiming for its reduction. Further, the present invention relates to the cosmetic use of such composition.

  本发明涉及一种组合物，该组合物包含一种五环三萜类化合物或其药学上可接受的盐，以及至少一种其他成分C，用于局部治疗或预防哺乳动物与不期望的局部皮下脂肪沉积相关的病症，其中所述化合物被注射到所述局部皮下脂肪沉积中，以减少其沉积。此外，本发明还涉及此类组合物的美容用途。
• Treatment of gynoid lipodystrophy
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：US11344573B2

  公开（公告）日：2022-05-31

  The present invention generally relates to the treatment of gynoid lipodystrophy, and more specifically to the use of calcium (hydroxy)phosphate particles in combination with at least one compound capable of reducing local subcutaneous fat in the treatment of gynoid lipodystrophy.

  本发明一般涉及妇科脂肪营养不良症的治疗，更具体地说，涉及将（羟基）磷酸钙颗粒与至少一种能够减少局部皮下脂肪的化合物结合使用，以治疗妇科脂肪营养不良症。
• 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。
• Synthesis and pharmacokinetic profile of rhein- boswellic acid conjugate
  作者：Dhaneshwar Suneela、Patil Dipmala

  DOI：10.1016/j.bmcl.2012.10.017

  日期：2012.12

  Rhein, an active metabolite of diacerein, down-regulates the gene-expression and production of pro-matrix metalloproteinases and up-regulates the tissue inhibitors of metalloproteinase-1 production. The therapeutic effects of diacerein on osteoarthritis are, at least in part, due to the chondroprotective effect of rhein. Boswellic acid is a specific, non-redox inhibitor of leukotriene synthesis. It is claimed to possess good anti-inflammatory, anti-arthritic, analgesic, and anti-ulcer activities. It prevents the destruction of articular cartilage by decreasing degradation of glycosaminoglycans. Therefore, rhein and boswellic acid were linked chemically through a bioreversible ester linkage to synthesize their mutual prodrug by reported procedure. In vitro release profile of this prodrug was extensively studied in aqueous buffers of varied pH, upper GIT homogenates and 80% human plasma. In vivo release studies were undertaken in blood, urine and feces of rats. The prodrug was stable in HCl buffer (pH 1.2) and stomach homogenates of rats. However; in phosphate buffer (pH 7.4) and in intestinal homogenates the prodrug exhibited 91% and 96% release of rhein and 27.5% and 38% release of boswellic acid respectively over a period of 6 h following first order kinetics. In 80% human plasma (in vitro) and rat blood (in vivo) also 96.35% and 91% release of rhein and 78% and 86.41% release of boswellic acid respectively was observed. The 24 h pooled samples of rat urine revealed presence of 6.2% intact prodrug, 7.1% of rhein and 8.9% of boswellic acid indicating their renal excretion. Samples of rat feces pooled over a period of 24 h showed absence of rhein and presence of 3.1% of intact boswellic acid and 4.6% of boswellic acid emphasizing their intestinal excretion. The in vivo release kinetics of prodrug in rat clearly indicated activation of prodrug to be occurring in blood, being catalyzed by the weak alkaline pH of blood (7.4) in combination with esterases present therein. (c) 2012 Elsevier Ltd. All rights reserved.