乙酸降香醇酯 | 17020-04-1

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 乙酸降香醇酯
• 英文名称: bauerenol acetate
• 英文别名: bauerenyl acetate；3β-acetoxy-D:C-friedo-urs-7-ene；3β-Acetoxy-D:C-friedo-urs-7-en；[(3S,4aR,6aS,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,7,8,9,10,11,12,12a,13,14,14a-tetradecahydro-1H-picen-3-yl] acetate
• CAS: 17020-04-1
• 化学式: C₃₂H₅₂O₂
• 分子量: 468.764
• InChiKey: DTHUXXMWYWKQKX-QXZXTIJDSA-N

物化性质

• 熔点：
  282-283 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  508.0±49.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)
• 保留指数：
  3437

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸降香醇酯 在 盐酸 作用下， 以 氯仿 为溶剂， 生成 isobauerenyl acetate
  参考文献：
  名称：

  萜类化合物和相关化合物-III：来自何首乌的Bauerenol和何首乌。多元酚的结构

  摘要：

  从多花Gelonium A. Juss的树皮中分离出了Bauerenol（Ia）和一种新的三萜醇Multiflorenol 。根据理化依据。建议将结构Va用于多元酚。

  DOI：

  10.1016/0040-4020(63)80013-7

文献信息

• Peracid induced oxidative rearrangements of triterpenoids: Products of new skeleton from bauerenyl acetate
  作者：Ajit Kumar Chakravarty、Binayak Das、Kazuo Masuda、Yoko Arai、Kenji Shiojima

  DOI：10.1016/s0040-4020(98)00300-7

  日期：1998.5

  of bauerenyl acetate (2) with m-chloroperbenzoic acid at 4 °C yielded the migrated products, viz. 7α-hydroxy-14,27-cycloisoursan-3β-yl acetate (9) and its 15α-hydroxy derivative (12) belonging to a new skeleton, 7α-hydroxyisours-14-en-3β-yl acetate (10) and 14α,15α-epoxy-7α-hydroxyisoursan-3β-yl acetate (11), besides 7α,8α-epoxybaueran-3β-yl acetate (3), bauera-7,9(11)-dien-3β-yl acetate (4), bauera-6

  bauerenyl乙酸乙酯（处理2）用米在4℃下氯过苯甲酸，得到迁移的产品，即 属于新骨架的7α-羟基-14,27-环异硫氰酸-3β-乙酸乙烯酯（9）及其15α-羟基衍生物（12），乙酸7α-羟基异硫醇14-en-3β-乙酸乙烯酯（10）和14α， 15α环氧7α-hydroxyisoursan-3β基乙酸酯（11），除了7α，8α-epoxybaueran-3β基乙酸酯（3），bauera -7,9（11） -二烯3β基乙酸酯（4）， bauera-6,8-dien-3β-乙酸乙烯酯（5），7α，8α-epoxybauer-9（11）-en-3β-乙酸乙烯酯（6），7α，8α，9α，11α-二乙氧基baueran-3β-yl醋酸盐（7）和8α，9α-环氧-7α-羟基baueran-3β-乙酸乙烯酯（8）。主要根据2D NMR光谱分析来阐明所有产物的结构。醋酸鲍尔烯基酯（2）及其反应产物（3-12）的1
• Triterpene constituents of Tabernaemontana laurifolia and Haplophyton cimicidum
  作者：M.P. Cava、A.K. Shubber、Kota V. Rao

  DOI：10.1016/s0031-9422(00)86094-x

  日期：1967.9

  Abstract The triterpene bauerenyl acetate was isolated directly by crystallization from the non-polar neutral extract of the bark of Tabernaemontana laurifolia D.C. A similar extract of Haplophyton cimicidum (whole plant) yielded, after chromatography, the triterpenes erythrodiol monostearate, bauerenol and betulin, as well as the steroid β-sitosterol.

  摘要 从月桂树树皮的非极性中性提取物中结晶直接分离出醋酸三萜醇盐 A 类似的 Haplophyton cimicidum（全株）提取物，经层析后，还得到三萜类高球二醇单硬脂酸酯、月桂醇和桦木脑。如类固醇β-谷甾醇。
• Bauerenol Acetate, the Pentacyclic Triterpenoid from Tabernaemontana longipes, is an Antitrypanosomal Agent
  作者：Simira Carothers、Rogers Nyamwihura、Jasmine Collins、Huaisheng Zhang、HaJeung Park、William Setzer、Ifedayo Ogungbe

  DOI：10.3390/molecules23020355

  日期：——

  as a potential source of antiparasitic agents. The chloroform extract of T. longipes leaves was separated into several fractions, and tested for antitrypanosomal activity. One of the fractions displayed significant growth inhibitory activity against Trypanosoma brucei. The active principle in the fraction was isolated, purified, and characterized by NMR and mass spectrometry. The antitrypanosomal agent

  在这项工作中研究了拉丁美洲植物 Tabernaemontana longipes 作为抗寄生虫剂的潜在来源。T. longipes 叶的氯仿提取物被分成几个部分，并测试抗锥虫活性。其中一个级分对布氏锥虫显示出显着的生长抑制活性。馏分中的活性成分被分离、纯化，并通过核磁共振和质谱进行表征。T. longipes 叶的 CHCl3 提取物中的抗锥虫剂是五环三萜类醋酸盐。代谢物分析表明三萜影响胆固醇代谢。像许多其他抗寄生虫五环三萜类化合物一样，bauerenol 及其醋酸盐的分子靶点是未知的，
• 13C NMR Assignments ofD:C-Friedours-7-ene Derivatives. Evidence of an Abnormal Methyl Group Chemical Shift
  作者：Carlos M. Cerda-García-Rojas、Héctor H. Hernández-Vidal、Pedro Joseph-Nathan

  DOI：10.1002/(sici)1097-458x(199610)34:10<777::aid-omr967>3.0.co;2-0

  日期：1996.10

  The 13C NMR assignments of four D:C‐friedours‐7‐ene derivatives were carried out on the basis of 2D shift‐correlated NMR techniques (HETCOR and FLOCK), revealing that the signal for CH3‐28 appears always very deshielded (ca. δ = 38.0). The conformation of the triterpene skeleton, obtained by MMX calculations, is compared with that of multiflor‐7‐ene.

  四种 D:C-friedours-7-ene 衍生物的 13C NMR 分配是在 2D 位移相关 NMR 技术（HETCOR 和 FLOCK）的基础上进行的，表明 CH3-28 的信号似乎总是非常去屏蔽（大约δ = 38.0)。通过MMX计算获得的三萜骨架的构象与多花7-烯的构象进行了比较。
• Indole alkaloids and terpenoids fromTabernaemontana markgrafiana
  作者：Helene B. Nielsen、Alan Hazell、Rita Hazell、Felipe Ghia、Kurt B.G. Torssell

  DOI：10.1016/s0031-9422(00)89601-6

  日期：1994.12

  The bark of Tabernaemontana markgrafiana yielded five acetylated pentacyclic triterpenes and 24 monoterpene indole alkaloids. The major triterpene was baurenyl acetate, which constituted ca 6% of the crude petrol extract. An X-ray study of iso-ursenyl acetate was carried out for the first time. The indole alkaloids were primarily of the iboga-type and constituted ca 3% of the dried bark and 20% of the total extracts. The major alkaloids were coronaridine, (19S)-heyneanine, voacangine and ibogamine. Among the minor components, four new alkaloids were identified: 5,6-dehydro-coronaridine, 3R-methoxy-coronaridine, 3R-methoxyvoacangine and the 10,11-demethoxy chippiine.