(3β)-3,27-dihydroxyolean-12-en-28-oic acid | 55497-67-1

• 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: (3β)-3,27-dihydroxyolean-12-en-28-oic acid
• 英文别名: 3β,24-dihydroxyolean-12-en-28-oic acid；3β,27-dihydroxyolean-12-en-28-oic acid；27-hydroxyoleanoic acid；myricerol；(3beta)-3,27-Dihydroxyolean-12-en-28-oic acid；(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-(hydroxymethyl)-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 55497-67-1
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: ADBMMSFXIFGNAX-MDAIVZGXSA-N

物化性质

• 沸点：
  591.8±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β)-3,27-dihydroxyolean-12-en-28-oic acid 在 吡啶 、 氢氧化钾 、 jones' reagent 、 二叔丁基过氧化物 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 10.5h， 生成 3-oxo-27-hydroxy-28-desmethylolean-12-ene
  参考文献：
  名称：

  Endothelin Receptor Antagonist Triterpenoid, Myriceric Acid A, Isolated from Myrica cerifera, and Structure Activity Relationships of Its Derivatives.

  摘要：

  作为第一种非肽类内皮素受体拮抗剂，新的三萜类化合物——美洲杜鹃酸A（myiceric acid A，50-235）（1）是从海梅果（Myrica cerifera）中分离得到的。美洲杜鹃酸A（1）不仅抑制了内皮素-1诱导的细胞质游离Ca<2+>浓度的增加（IC50 = 11±2 nM），还抑制了[<125&I]内皮素-1在大鼠主动脉平滑肌细胞中的结合（Ki = 66±15 nM）。此外，还分离出了两种新的相关三萜类化合物，美洲杜鹃酸C（6）和美洲杜鹃酸D（8）。进一步地，对这些天然产物的化学修饰导致合成了硫酸酯衍生物（13、14、15），其对内皮素受体的亲和力提高了1.5到20倍。讨论了美洲杜鹃酸及其衍生物的结构活性关系。

  DOI：

  10.1248/cpb.44.343
• 作为产物：
  描述：

  在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(3β)-3,27-dihydroxyolean-12-en-28-oic acid
  参考文献：
  名称：

  Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

  摘要：

  Myriceric acid A (1) is an oleanane triterpene that is a potent and specific endothelin A receptor antagonist. A practical procedure for large-scale synthesis of myriceric acid A (1) has been developed starting from oleanolic acid 4. The conversion of oleanolic acid 4 to the key intermediate myricerone 3 was achieved in an efficient manner employing a photochemical reaction (the Barton reaction) of nitrite 7. Our synthetic procedure alleviated several difficulties of the original Barton's procedure with regard to yields and large-scale operation. Myricerone 3 afforded Horner-Wadsworth-Emmons (HWE) type phosphonate 2 which has proved to be a versatile precursor of 1. The preparation of phosphonate 2 on a scale of several hundred grams is described. The synthesis was completed by condensation of 2 with 3,4-bis[(diphenylmethyl)oxy]benzaldehyde (21), giving alpha,beta-unsaturated ester 22, which was deprotected to afford 1. The whole synthetic sequence is efficient (14 steps, 31% yield) and requires no chromatographic purification except to obtain the final product 1.

  DOI：

  10.1021/jo9615864

文献信息

• A triterpene glycoside from the fruits of Tetrapleura tetraptera
  作者：M Maillard、C.O Adewunmi、K Hostettmann

  DOI：10.1016/0031-9422(92)80500-e

  日期：1992.4

  Abstract A new saponin has been isolated from the molluscicidal extract of the fruits of Tetrapleura tetraptera . Chemical, enzymatic and spectral methods (D/CIMS, 1 H, 13 C NMR) showed that it was a monodesmosidic diglycoside of the rare sapogenin 27-hydroxyolean-12(13)-en-28-oic acid.

  摘要 从四翅四翅果的杀软体动物提取物中分离到了一种新的皂苷。化学、酶促和光谱方法 (D/CIMS, 1 H, 13 C NMR) 表明它是稀有皂苷元 27-hydroxyolean-12(13)-en-28-oic 酸的单糖苷二糖苷。
• Two new triterpenoid saponins from rhizome of Anemone raddeana Regel
  作者：Li Fan、Jincai Lu、Jing Wang、Weiming Cheng、Yan Yao、Runxiang Liu、Hongfen Zhang

  DOI：10.1007/s11418-009-0369-x

  日期：2010.1

  Two new 27-hydroxyoleanolic acid-type triterpenoid saponins, raddeanoside Ra (1) and raddeanoside Rb (2), were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated to be 27-hydroxyoleanolic acid 3-O-β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranoside (1) and 27-hydroxyoleanolic acid 3-O-α-l-arabinopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α- l-arabinopyranoside (2) on the basis of chemical and spectral evidence.

  从Anemone raddeana Regel的根茎中分离出两种新的27-羟基齐墩果酸型三萜皂苷，即raddeanoside Ra (1)和raddeanoside Rb (2)。根据化学和光谱证据，这两种化合物的结构被确定为27-羟基齐墩果酸3-O-β-d-吡喃葡萄糖基-(1 → 4)-α-l-阿拉伯吡喃糖苷 (1)和27-羟基齐墩果酸3-O-α-l-阿拉伯吡喃糖基-(1 → 3)-α-l-鼠李吡喃糖基-(1 → 2)-α- l-阿拉伯吡喃糖苷 (2)。
• Method and compostitions for treating coronavirus infection
  申请人：PHOENIX BIOTECHNOLOGY, INC.

  公开号：US10729735B1

  公开（公告）日：2020-08-04

  A method of treating viral infection, such as viral infection caused by a virus of the Coronaviridae family, is provided. A composition having at least oleandrin is used to treat viral infection.

  提供了一种治疗病毒感染的方法，例如由冠状病毒科病毒引起的病毒感染。一种至少含有齐墩果素的组合物用于治疗病毒感染。
• EP1757573
  申请人：——

  公开号：——

  公开（公告）日：——
• FAGONIA BRUGUIERI FREEZE-DRIED EXTRACT AS ANTI-ALLERGIC TREATMENT
  申请人：AL-YAHYA, Mohammed Abdulaziz

  公开号：EP1948207A1

  公开（公告）日：2008-07-30