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。
• Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2003.12.023

  日期：2004.2

  Some triterpenic compounds modified in C-ring were semi-synthesised from oleanolic acid contained in the solid waste of olive-oil pressing. The corresponding esters of oleanolic and maslinic acids rendered products with a diene system, which led to oleantrienes resembling previtamin D2 by an electrocyclic reaction. Chemical and photochemical isomerization of these compounds yielded two different trienes

  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。
• 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.