2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic acid | 6753-23-7

• 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: 2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic acid
• 英文别名: tomentosic acid；Tomentosesaeure,(2α,3β,19β,23-Tetrahydroxy-olean-12-en-28-saeure)；2α,3β,19β,23-Tetrahydroxy-olean-12-en-28-saeure；Tomentossaeure；(1R,4aR,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-1,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 6753-23-7
• 化学式: C₃₀H₄₈O₆
• 分子量: 504.708
• InChiKey: IFIQVSCCFRXSJV-GCVAJSGBSA-N

物化性质

• 熔点：
  328-330 °C
• 沸点：
  639.3±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 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：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic acid 生成 Tomentossaeure-methylester
  参考文献：
  名称：

  MAHATO, SHASHI B.;NANDY, ASHOKE K.;LUGER, PETER;WEBER, MANUELA, J. CHEM. SOC. PT 2. PERKIN TRANS.,(1990) N, C. 1445-1450

  摘要：

  DOI：
• 作为产物：
  描述：

  1-O-[(2alpha,3beta,19alpha)-2,3,19,23-四羟基-28-氧代齐墩果-12-烯-28-基]-beta-D-吡喃葡萄糖 、 盐酸 、 甲醇 生成 2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic acid
  参考文献：
  名称：

  MAHATO, SHASHI B.;NANDY, ASHOKE K.;LUGER, PETER;WEBER, MANUELA, J. CHEM. SOC. PT 2. PERKIN TRANS.,(1990) N, C. 1445-1450

  摘要：

  DOI：

文献信息

• Chemistry of terminalia species—VI
  作者：L. Ramachandra Row、G.S.R. Subba Rao

  DOI：10.1016/s0040-4020(01)92734-6

  日期：1962.1

  From the heartwood of T. tomentosa Wight et Arn, β-sitosterol, oleanolic acid (VI, R = R1 = H), arjunolic acid (I) and barringtogenol (IV) were isolated and in addition a new tetrahydroxy triterpene mono-carboxylic acid, now named Tomentosic acid. The triacetylmethyl tomentosate was oxidized to the corresponding ketone (XV) which could be reduced by forced Wolff-Kishner method to give methyl arjunolate

  从毛白杨的心材中提取β-谷固醇，齐墩果酸（VI，R = R 1＝ H），分离出壬酸（I）和巴丁香酚（IV），此外还分离了新的四羟基三萜单羧酸，现称为Tomentosic acid。将三乙酰基甲基绒毛酸酯氧化为相应的酮（XV），可以通过强制Wolff-Kishner方法将其还原，得到阿魏酸甲酯（III）。上述酮在碱的存在下也经历异构化，得到α，β-不饱和酮（XVI）。此外，在内酯化过程中，酸产生三羟基脱水内酯（X）。可以使用二氧化硒使三乙酰基甲酯脱水，得到甲基脱氢阿魏酸酯（XIX）。从这些反应中，将绒毛膜酸暂定为2α，3β，19β，23-四羟基-油烯-12-烯-28-油酸（XII，R ＝ H）。
• ACCELERATOR FOR INITIAL INSULIN SECRETION
  申请人：Use-Techno Corporation

  公开号：EP1674089A1

  公开（公告）日：2006-06-28

  The present invention provides an early insulin secretion stimulator consisting of a triterpene represented by the following general formula (1) and/or a triterpene represented by the following general formula (2). [where R1 represents COOH, etc., R11 and R12 represent CH2OH, etc., X1 represents hydrogen or OH and X11, X12, X21 and X22 represent OH, etc.]

  本发明提供了一种早期胰岛素分泌刺激剂，由以下通式（1）代表的三萜和/或以下通式（2）代表的三萜组成。 [其中 R1 代表 COOH 等，R11 和 R12 代表 CH2OH 等，X1 代表氢或 OH，X11、X12、X21 和 X22 代表 OH 等。］
• MAHATO, SHASHI B.;NANDY, ASHOKE K.;LUGER, PETER;WEBER, MANUELA, J. CHEM. SOC. PT 2. PERKIN TRANS.,(1990) N, C. 1445-1450
  作者：MAHATO, SHASHI B.、NANDY, ASHOKE K.、LUGER, PETER、WEBER, MANUELA

  DOI：——

  日期：——
• Cyclooxygenase-2 enzyme inhibitory triterpenoids from Picrorhiza kurroa seeds
  作者：Yanjun Zhang、David L. DeWitt、Sorimuthu Murugesan、Muraleedharan G. Nair

  DOI：10.1016/j.lfs.2005.05.051

  日期：2005.11

  A bioassay guided phytochemical study of the ethyl acetate extract of the seeds of Picrorhiza kurroa afforded a new triterpenoid, 2 alpha, 3 beta, 19 beta, 23-tetrahydroxyolean-12-en-28-O-beta-D-glucoside (1), along with five known triterpenoids, 2 alpha, 3 beta, 19 beta, 23-tetrahydroxyolean-12-en-28-oic acid (2), 2 alpha, 3 beta, 23-trihydroxyolean-12-en-28-O-beta-D-glucoside (3), 2 alpha, 3 beta, 23-trihydroxyolean-12-en-28-oic acid (4), 2 alpha, 3 beta, 19 beta, trihydroxyolean-12-en-28-oic acid (5), and 2 alpha, 3 beta, 6 beta, 23-tetrahydroxyolean-12-en-28-oic acid (6). Their structures were established by extensive NMR spectral studies. The acetyl derivatives, compounds 7 and 8, were prepared from compounds 1 and 2, respectively, to aid in their structure elucidation. The inhibition of cyclooxygenase-2 (COX-2) enzyme by compounds 1-6 at 100 mu g/mL was 38.3%, 39%, 37%, 49.6%, 25%, and 45.0%, respectively. However, compounds 1-6, at 100 mu g/mL, did not inhibit cyclooxygenase-1 (COX-1) enzyme. Compound 1 is a novel triterpenoid and compounds 1-6 are isolated for the first time from the seeds of P kurroa. (c) 2005 Elsevier Inc. All rights reserved.
• Insulin secretion potentiator
  申请人：Matsuyama Futoshi

  公开号：US20050143464A1

  公开（公告）日：2005-06-30

  The present invention provides early insulin secretion stimulators consisting of triterpenes represented by the following general formula (1) and/or triterpenes represented by the following general formula (2). [where R 1 represents COOH, etc., R 11 and R 12 represent CH 2 OH, etc., X 1 represents hydrogen or OH and X 11 , X 12 , X 21 and X 22 represent OH, etc.]