3-dehydroxy-oleanolic acid | 17990-43-1

• 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: 3-dehydroxy-oleanolic acid
• 英文别名: oleanan-12-en-28-oic acid；olean-12-en-28-oic acid；12-oleanen-28-oic acid；deoxyoleanolic acid；oleanoic acid；oleanic acid；(4aS,6aR,6aS,6bR,8aS,12aS,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 17990-43-1
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: MXEMKMNFLXVQBW-CDNBJWEZSA-N

物化性质

• 熔点：
  207-209 °C (decomp)
• 沸点：
  522.6±19.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  32
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-dehydroxy-oleanolic acid 在 吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 olean-12-en-28-al
  参考文献：
  名称：

  Terpenoids. LVII.¹ Mass Spectral and Nuclear Magnetic Resonance Studies of Pentacyclic Triterpene Hydrocarbons²

  摘要：

  DOI：

  10.1021/jo01344a063
• 作为产物：
  描述：

  齐墩果酸 在 chromium(VI) oxide 、 氢氧化钾 、 硫酸 、 一水合肼 作用下， 以 乙醇 、 丙酮 、 二乙二醇 为溶剂， 反应 2.0h， 生成 3-dehydroxy-oleanolic acid
  参考文献：
  名称：

  Terpenoids. LVII.¹ Mass Spectral and Nuclear Magnetic Resonance Studies of Pentacyclic Triterpene Hydrocarbons²

  摘要：

  DOI：

  10.1021/jo01344a063

文献信息

• Oleanolic acid and its derivatives: New inhibitor of protein tyrosine phosphatase 1B with cellular activities
  作者：Yi-Nan Zhang、Wei Zhang、Di Hong、Lei Shi、Qiang Shen、Jing-Ya Li、Jia Li、Li-Hong Hu

  DOI：10.1016/j.bmc.2008.07.080

  日期：2008.9

  Protein tyrosine phosphatase 1B is a key factor in the negative regulation of insulin pathway and a promising target for treatment of diabetes and obesity. Herein, a series of competitive inhibitors were optimized from oleanolic acid, a natural triterpenoid identified against PTP1B by screening libraries of traditional Chinese medicinal herbs. Modifying at 3 and 28 positions, we obtained compound 13

  酪氨酸磷酸酶1B蛋白是胰岛素通路负调节的关键因素，也是治疗糖尿病和肥胖症的有希望的靶标。本文中，通过筛选传统中草药文库中鉴定出的针对PTP1B的天然三萜类化合物齐墩果酸，优化了一系列竞争性抑制剂。在3和28位上进行修饰，我们获得了K（i）为130 nM的化合物13，该化合物在除T细胞蛋白酪氨酸磷酸酶以外的其他与胰岛素途径有关的磷酸酶之间表现出良好的选择性。在细胞模型中的进一步评估表明，这些衍生物增强了CHO / hIR细胞中胰岛素受体的磷酸化作用，并刺激了添加或不添加胰岛素的L6肌管中的葡萄糖摄取。
• Cross-ß structure binding compounds
  申请人：Crossbeta Biosciences B.V.

  公开号：EP2386861A2

  公开（公告）日：2011-11-16

  The invention relates to the field of biochemistry, biophysical chemistry, molecular biology, structural biology and medicine. More in particular, the invention relates to cross-β structure conformation. Even more particular, the invention relates to compounds capable of binding to a compound with cross-β structure conformation, i.e. cross-β structure binding compounds and uses thereof.

  本发明涉及生物化学、生物物理化学、分子生物学、结构生物学和医学领域。更具体地说，本发明涉及交叉β结构构象。更具体地说，本发明涉及能够与具有交叉β结构构象的化合物结合的化合物，即交叉β结构结合化合物及其用途。
• Compositions and methods for prostate and kidney health and disorders, an herbal preparation
  申请人：——

  公开号：US20030134000A1

  公开（公告）日：2003-07-17

  A composition including an aliquot of the herb Herba Epimedii; and an aliquot of at least three supplemental herbs selected from the group consisting of Fructus Rosae Laevigatae; Fructus Rubi; Fructus Psoralea; Radix Morindae Officinalis; Fructus Schisandrac Chinensis; Fructus Ligustri Lucidi; Semen Cuscutae; and Radix Astragali. A composition including icariin; ursolic acid; ellagic acid; psoralen; deoxyschizandrin; oleanolic acid; quercetin; aslvagaloside; and an extract of the herb Radix Morindae Officinalis. Methods including administering a composition directed at treatment of various kidney disorders or the promotion of kidney health and to the overall health of the kidney, including the use of a composition in the treatment of prostate cancer, prophylatic prostate health, reduction of polyuria, incontinence, proteinuria, as well as for sexual satisfaction.

  一种组合物，包括淫羊藿的等分草本；以及至少三种补充草本的等分草本，这些补充草本选自以下组别：蔷薇科植物；茜草科植物；补骨脂科植物；巴戟天科植物；五味子科植物；枸杞子科植物；菟丝子科植物；以及黄芪科植物。一种组合物，包括冰片苷、熊果酸、鞣花酸、补骨脂素、脱氧雪胆素、齐墩果酸、槲皮素、巴戟苷和巴戟天提取物。方法包括施用针对治疗各种肾脏疾病或促进肾脏健康和肾脏整体健康的组合物，包括将组合物用于治疗前列腺癌、促进前列腺健康、减少多尿、尿失禁、蛋白尿以及性满足。
• Different pathways for the deoxygenation of the A-ring of natural triterpene compounds
  作者：Andres Parra、Pilar E. Lopez、Andres Garcia-Granados

  DOI：10.1080/14786410903172098

  日期：2010.1.20

  Some deoxygenation pathways were tested to remove the hydroxyl groups of the natural triterpenes oleanolic acid and maslinic acid to obtain a practical starting material for the semisynthesis of other interesting organic synthons. Different deoxygenation processes were carried out starting from these triterpenic acids or from several derivatives such as methyl esters and epoxy derivatives. The hydroxyl groups were transformed into some intermediate compounds including xanthyl, thiocarbonyl or tosyl derivatives. The opening of the oxirane ring between C-2 and C-3 was also achieved through different methods using deoxygenating reagents such as Me3SiCl/NaI, WCl4/n-BuLi and Cp2TiCl.
• Savoir,R. et al., Bulletin des Societes Chimiques Belges, 1967, vol. 76, p. 335 - 367
  作者：Savoir,R. et al.

  DOI：——

  日期：——