20(S)-protopanaxadiol

• 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: 20(S)-protopanaxadiol
• 英文别名: Dammarane-(E)-20(22)-ene-3beta,12beta,25-triol；(3S,8R,10R,12R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
• 化学式: C₃₀H₅₂O₃
• 分子量: 460.741
• InChiKey: PYXFVCFISTUSOO-NKYJHZBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Acetic acid (3R,8R,10R,14R)-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-12-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 2.0h， 生成 20(S)-protopanaxadiol 、 3β,12α,20S-trihydroxydammar-24-ene
  参考文献：
  名称：

  Synthesis of β-D-Glucopyranosides of 12α-Epimers of 20S-Protopanaxadiol and Betulafolientriol

  摘要：

  DOI：

  10.1007/s10600-024-04464-7

文献信息

• Synthetic Method of 20 (S)-Ginsenoside Rh2
  申请人：Hui Yongzheng

  公开号：US20080275225A1

  公开（公告）日：2008-11-06

  A synthetic method of 20(s)-ginsenoside Rh2, that is 20(S)-protopanaxdiol-3-O-β-D-glucopyranoside, is comprised of: protecting protopanaxdiol (A1) selectively first to produce monosubstituted protopanaxdiol (A2); and Glycosidating the monosubstituted protopanaxdiol with Glucopyranosyl donor in the presence of Lewis acid catalyst; Deprotecting the product; Then separating and purifying to obtain 20(s)-ginsenoside Rh2. The method is conducted under mild condition at low cost, and affords product with high stereoselectivity, high yield and purity. Therefore, the synthetic method of the present invention is suitable for production on large scale.

  一种20（s）-人参皂苷Rh2的合成方法，即20（S）-原人参二醇-3-O-β-D-葡萄糖苷，包括：首先选择性地保护原人参二醇（A1）以生成单取代原人参二醇（A2）；然后在Lewis酸催化剂存在下将单取代原人参二醇与葡萄糖吡喃基供体进行糖苷化反应；脱保护产物；然后分离纯化以获得20（s）-人参皂苷Rh2。该方法在温和条件下，成本低廉，并且产物具有高立体选择性、高产率和纯度。因此，本发明的合成方法适用于大规模生产。
• Method for selectively producing ginsenoside Rd from saponins of ginseng through enzymatic method
  申请人：AMOREPACIFIC CORPORATION

  公开号：US10519480B2

  公开（公告）日：2019-12-31

  The present invention relates to a method for selectively producing ginsenoside Rd, which is originally present in ginseng in a trace amount, from panaxadiol-type saponins of ginseng, and more specifically to a method capable of obtaining a desired target compound, that is, ginsenoside Rd, in high yields, by treating a panaxadiol-type saponin obtained from ginseng, with particular enzymes to structurally convert the saponins.

  本发明涉及一种从人参的三七皂甙中选择性地生产人参皂甙 Rd 的方法，更具体地说，涉及一种用特殊的酶处理从人参中获得的三七皂甙，使皂甙结构转化，从而高产率地获得所需的目标化合物，即人参皂甙 Rd 的方法。
• USE OF 20(S)-PROTOPANAXADIOL IN MANUFACTURE OF ANTIDEPRESSANTS
  申请人：Hui Yongzheng

  公开号：US20100234624A1

  公开（公告）日：2010-09-16

  The invention provides the novel use of 20(S)-protopanaxadiol in the preparation of medicaments for the treatment of depressive psychiatric disorders. The pharmacological test results indicated that the compound could remarkably increase the level of NE, 5-HT and HAV in the brains of model rats having depressive disorders, remarkably enhance tremors induced by 5-hydroxytryptophan (5-HTP) and behavioral effects induced by levodopa, and inhibit the re-uptake of 5-HT and NA.
• APPLICATION OF 20(S)-PROTOPANAXADIOL IN PREPARATION OF ANTIDEPRESSANTS
  申请人：Hui Yongzheng

  公开号：US20120214779A1

  公开（公告）日：2012-08-23

  The invention provides the novel use of 20(S)-protopanaxadiol in the preparation of medicaments for the treatment of depressive psychiatric disorders. The pharmacological test results indicated that the compound could remarkably increase the level of NE, 5-HT and HAV in the brains of model rats having depressive disorders, remarkably enhance tremors induced by 5-hydroxytryptophan (5-HTP) and behavioral effects induced by levodopa, and inhibit the re-uptake of 5-HT and NA.
• Compounds For Use As Imaging Agents
  申请人：United Arab Emirates University

  公开号：US20170307623A1

  公开（公告）日：2017-10-26

  The present invention describes the use of the Chinese medicinal compounds ginsenoside RB1, dihydromyricetin and salvianohc acid B, for use in diagnosing, monitoring and treating synucleinopathies, such as Parkinson's disease, in patients.