methyl 2α,3β-diacetoxy-12-oleane-28-oate | 19533-95-0

• 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: methyl 2α,3β-diacetoxy-12-oleane-28-oate
• 英文别名: (2α,3β) methyl 2,3-diacetyl-olean-12-en-28-oate；2α,3β-diacetoxy-olean-12-en-28-oic acid methyl ester；2α,3β-Diacetoxy-olean-12-en-28-saeure-methylester；methyl (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-diacetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 19533-95-0
• 化学式: C₃₅H₅₄O₆
• 分子量: 570.81
• InChiKey: ROHJAYQXFRNZHR-UBFFDPSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2α,3β-diacetoxy-12-oleane-28-oate 在 氢氧化钾 作用下， 反应 24.0h， 以66 mg的产率得到马斯里酸甲酯
  参考文献：
  名称：

  Krishnaswamy, N. R.; Rao, G. Nageswara; Omana, P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 8, p. 769 - 772

  摘要：

  DOI：
• 作为产物：
  描述：

  山楂酸 在 吡啶 、 sodium hydroxide 作用下， 生成 methyl 2α,3β-diacetoxy-12-oleane-28-oate
  参考文献：
  名称：

  由齐墩果酸和山梨酸部分合成C环衍生物。通过化学和光化学异构化过程形成数个三烯系统

  摘要：

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。

  DOI：

  10.1016/j.tet.2003.12.023

文献信息

• Triterpenes from Prunus africana bark
  作者：C. Fourneau、R. Hocquemiller、A. Cavé

  DOI：10.1016/0031-9422(96)00038-6

  日期：1996.7

  A chloroformic extract of barks of Prunus africana was found to contain triterpenic acids including derivatives of ursolic and oleanolic acids. Among them 24-O-trans-ferulyl-2α,3α-dihydroxy-urs-12-en-28-oic acid, an original compound, was isolated. Their structure was established by chemical and spectral analysis.

  发现非洲李树皮的氯仿提取物含有三萜酸，包括熊果酸和齐墩果酸的衍生物。其中分离出原始化合物 24-O-trans-ferulyl-2α,3α-dihydroxy-urs-12-en-28-oic acid。它们的结构是通过化学和光谱分析确定的。
• 3-acetylmaslinic acid from the root bark of Terminalia alata
  作者：A.S.R. Anjaneyulu、A.V.Raghava Reddy、Gopal R. Mallavarapu、R.S. Chandrasekhara

  DOI：10.1016/s0031-9422(00)84538-0

  日期：1986.1

  Abstract A new triterpene acid, 3-acetylmaslinic acid, has been isolated from the root bark of Terminalia alata together with oleanolic acid, arjunic acid, arjunolic acid and arjunetin.

  摘要 从榄仁树的根皮中分离到了一种新的三萜酸3-乙酰山楂酸，与齐墩果酸、阿姜酸、阿朱酚酸和熊果苷。
• Anti-inflammatory constituents of topically applied crude drugs. I. Constituents and anti-inflammatory effect of Eriobotrya japonica Lindl.
  作者：MINEO SHIMIZU、HIDEKI FUKUMURA、HIDEKI TSUJI、SEIICHI TANAAMI、TOSHIMITSU HAYASHI、NAOKATA MORITA

  DOI：10.1248/cpb.34.2614

  日期：——

  The ether-soluble fraction of EtOH extract from the leaves of Eriobotrya japonica LINDL.showed an anti-inflammatory effect when topically applied to rats. Ursolic acid, maslinic acid, methyl maslimate and euscaphic acid were isolated from the ether-soluble fraction. Maslinic acid was found to show an anti-inflammatory effect on carrageenan-induced edema and an inhibitory effect on histamine-induced ileum contraction.

  对大鼠局部施用枇杷叶的乙醇提取物的醚溶部分具有抗炎作用。从醚溶部分中分离出熊果酸、马斯林酸、马斯林酸甲酯和葫芦巴酸。研究发现，马斯林酸对卡拉胶诱导的水肿有消炎作用，对组胺诱导的回肠收缩有抑制作用。
• The chemical and biological potential of C ring modified triterpenoids
  作者：Bianka Siewert、Jana Wiemann、Alexander Köwitsch、René Csuk

  DOI：10.1016/j.ejmech.2013.11.025

  日期：2014.1

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.
• Remote Hydroxylation of Methyl Groups by Regioselective Cyclopalladation. Partial Synthesis of Hyptatic Acid-A
  作者：Andrés García-Granados、Pilar E. López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1021/jo070116e

  日期：2007.4.1

  Hyptatic acid-A (32), a 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.