urs-12-ene-3β-tetradecanoate

• 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: urs-12-ene-3β-tetradecanoate
• 英文别名: α-amyrin tetradecanoate；α-amyryl tetradecanoate；α-amyrin-3-myristate；α-amyrin myristate；[(3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] tetradecanoate
• 化学式: C₄₄H₇₆O₂
• 分子量: 637.086
• InChiKey: RSYAHDDVEPGCNX-VIQGCHITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  urs-12-ene-3β-tetradecanoate 在 甲醇 、 sodium hydroxide 作用下， 反应 10.0h， 生成 α-香树精
  参考文献：
  名称：

  Triterpene Esters: Natural Products from Dorstenia arifolia (Moraceae)

  摘要：

  对杜尔斯滕尼亚（Dorstenia arifolia Lam.）的植物化学研究已确认18种脂肪酸酯化的三萜、5种未酯化的三萜、12种醋酸酯化的三萜，以及一种已知的呋喃香豆素，包括：α-氨基醇（1）、β-氨基醇（2）、α-氨基醇醋酸酯（3）、β-氨基醇醋酸酯（4）、α-氨基醇辛酸酯（5）、β-氨基醇辛酸酯（6）、α-氨基醇癸酸酯（7）、β-氨基醇癸酸酯（8）、α-氨基醇十二酸酯（9）、β-氨基醇十二酸酯（10）、α-氨基醇十四酸酯（11）、β-氨基醇十四酸酯（12）、α-氨基醇十六酸酯（13）、β-氨基醇十六酸酯（14）、粘滑醇（15）、粘滑醇醋酸酯（16）、11-氧-α-氨基醇（17）、11-氧-β-氨基醇（18）、11-氧-α-氨基醇醋酸酯（19）、11-氧-β-氨基醇醋酸酯（20）、11-氧-α-氨基醇辛酸酯（21）、11-氧-β-氨基醇辛酸酯（22）、11-氧-α-氨基醇癸酸酯（23）、11-氧-β-氨基醇癸酸酯（24）、11-氧-α-氨基醇十二酸酯（25）、11-氧-β-氨基醇十二酸酯（26）、熊果烯-9(11),12-烯-3-醇醋酸酯（27）、橄榄烯-9(11),12-烯-3-醇醋酸酯（28）、熊果烯-9(11),12-烯-3-醇癸酸酯（29）、橄榄烯-9(11),12-烯-3-醇癸酸酯（30）、12,13-氧化倍半烯-3-醇醋酸酯（31）、12,13-氧化倍半烯-9(11)-烯-3-醇醋酸酯（32）、塔拉克塞烯醋酸酯（33）、拉乌佩烯醋酸酯（34）、平腺烯-8,24-烯-3-醇醋酸酯（35）和蕈素（36）。从己烷提取物中分离出的三萜化合物的同分异构体混合物的鉴定主要基于质谱和13C-NMR数据。三萜α-和β-氨基醇；11-氧-α-和11-氧-β-氨基醇；熊果烯和橄榄烯-9(11),12-烯-3-醇的长链烷酸酯在文献中尚未报道为杜尔斯滕尼亚属的成分。

  DOI：

  10.3390/molecules18044247
• 作为产物：
  描述：

  α-香树精 、 肉豆蔻酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 urs-12-ene-3β-tetradecanoate
  参考文献：
  名称：

  白杨木中重要甾醇酯的鉴定和定量

  摘要：

  AbstractSteryl esters make up a major portion of the total lipids in aspen wood, and contribute significantly to pitch deposit problems during pulping. Fungal treatment of aspen is an attractive method for removing these compounds because it is inexpensive and environmentally acceptable; however, the mechanism of steryl ester removal remains unclear. Identification of the steryl esters will lead to a better understanding of how they are removed by fungi. The steryl ester fraction from aspen wood was obtained by acetone extraction then further purified by silica gel column chromatography and argentation‐silica gel column chromatography. This led to the isolation of three major fractions: fraction I, fraction II, and fraction III. The major steryl esters of fractions I and II were identified by gas chromatography, gas chromatography‐mass spectroscopy, and proton nuclear magnetic resonance analysis of the intact fraction as well as sterol and fatty acid moieties obtained after base hydrolysis. Identification of the steryl esters was carried out by mass spectra comparisons with steryl ester standards synthesized in the laboratory and comparison with mass spectra libraries (Wiley and NIST) by mass fragmentography. Fraction I contained primarily the palmitate, stearate, and eicosanoate esters of α‐ and β‐amyrin. Fraction II consisted mainly of the palmitate, stearate, and eicosanoate esters of tirucalla‐7,24‐dien‐3β‐ol and lupeol.

  DOI：

  10.1007/s11746-000-0066-9

文献信息

• Triterpene Esters: Natural Products from Dorstenia arifolia (Moraceae)
  作者：Catharina Fingolo、Thabata Santos、Marcelo Filho、Maria Kaplan

  DOI：10.3390/molecules18044247

  日期：——

  The phytochemical study of Dorstenia arifolia Lam. (Moraceae) has led to the identification of 18 triterpenes esterified by fatty acids, five triterpenes without esterification, 12 triterpenes esterified by acetic acid, together with a known furanocoumarin: α-amyrin (1), β-amyrin (2) α-amyrin acetate (3) β-amyrin acetate (4), α-amyrin octanoate (5), β-amyrin octanoate (6), α-amyrin decanoate (7), β-amyrin decanoate (8), α-amyrin dodecanoate (9), β-amyrin dodecanoate (10), α-amyrin tetradecanoate (11), β-amyrin tetradecanoate (12), α-amyrin hexadecanoate (13), β-amyrin hexadecanoate (14), glutinol (15), glutinyl acetate (16), 11-oxo-α-amyrin (17), 11-oxo-β-amyrin (18), 11-oxo-α-amyrin acetate (19), 11-oxo-β-amyrin acetate (20) 11-oxo-α-amyrin octanoate (21) 11-oxo-β-amyrin octanoate (22), 11-oxo-α-amyrin decanoate (23), 11-oxo-β-amyrin decanoate (24) 11-oxo-α-amyrin dodecanoate (25) 11-oxo-β-amyrin dodecanoate (26), ursa-9(11),12-dien-3-yl acetate (27), oleana-9(11),12-dien-3-yl acetate (28), ursa-9(11),12-dien-3-yl decanoate (29), oleana-9(11),12-dien-3-yl decanoate (30), 12,13-epoxyolean-3-yl acetate (31), 12,13-epoxyolean-9(11)en-3-yl acetate (32), taraxeryl acetate (33), lupenyl acetate (34), lanosta-8,24-dien-3-yl acetate (35) and psoralen (36). The identification of the triterpene compounds isolated as isomeric mixtures obtained from the hexane extract was based mainly in mass spectra and 13C-NMR data. The long-chain alkanoic acid esters of the triterpenes α- and β-amyrin; 11-oxo-α- and 11-oxo-β-amyrin; ursa- and olean-9(11),12-dien-3-yl; have not been reported before in the literature as constituents of the Dorstenia genus.

  对杜尔斯滕尼亚（Dorstenia arifolia Lam.）的植物化学研究已确认18种脂肪酸酯化的三萜、5种未酯化的三萜、12种醋酸酯化的三萜，以及一种已知的呋喃香豆素，包括：α-氨基醇（1）、β-氨基醇（2）、α-氨基醇醋酸酯（3）、β-氨基醇醋酸酯（4）、α-氨基醇辛酸酯（5）、β-氨基醇辛酸酯（6）、α-氨基醇癸酸酯（7）、β-氨基醇癸酸酯（8）、α-氨基醇十二酸酯（9）、β-氨基醇十二酸酯（10）、α-氨基醇十四酸酯（11）、β-氨基醇十四酸酯（12）、α-氨基醇十六酸酯（13）、β-氨基醇十六酸酯（14）、粘滑醇（15）、粘滑醇醋酸酯（16）、11-氧-α-氨基醇（17）、11-氧-β-氨基醇（18）、11-氧-α-氨基醇醋酸酯（19）、11-氧-β-氨基醇醋酸酯（20）、11-氧-α-氨基醇辛酸酯（21）、11-氧-β-氨基醇辛酸酯（22）、11-氧-α-氨基醇癸酸酯（23）、11-氧-β-氨基醇癸酸酯（24）、11-氧-α-氨基醇十二酸酯（25）、11-氧-β-氨基醇十二酸酯（26）、熊果烯-9(11),12-烯-3-醇醋酸酯（27）、橄榄烯-9(11),12-烯-3-醇醋酸酯（28）、熊果烯-9(11),12-烯-3-醇癸酸酯（29）、橄榄烯-9(11),12-烯-3-醇癸酸酯（30）、12,13-氧化倍半烯-3-醇醋酸酯（31）、12,13-氧化倍半烯-9(11)-烯-3-醇醋酸酯（32）、塔拉克塞烯醋酸酯（33）、拉乌佩烯醋酸酯（34）、平腺烯-8,24-烯-3-醇醋酸酯（35）和蕈素（36）。从己烷提取物中分离出的三萜化合物的同分异构体混合物的鉴定主要基于质谱和13C-NMR数据。三萜α-和β-氨基醇；11-氧-α-和11-氧-β-氨基醇；熊果烯和橄榄烯-9(11),12-烯-3-醇的长链烷酸酯在文献中尚未报道为杜尔斯滕尼亚属的成分。
• Identification and quantification of important steryl esters in aspen wood
  作者：Alessio N. Serreqi、Robert Leone、Luis F. Del Rio、Shirley Mei、Marc Fernandez、Colette Breuil

  DOI：10.1007/s11746-000-0066-9

  日期：2000.4

  AbstractSteryl esters make up a major portion of the total lipids in aspen wood, and contribute significantly to pitch deposit problems during pulping. Fungal treatment of aspen is an attractive method for removing these compounds because it is inexpensive and environmentally acceptable; however, the mechanism of steryl ester removal remains unclear. Identification of the steryl esters will lead to a better understanding of how they are removed by fungi. The steryl ester fraction from aspen wood was obtained by acetone extraction then further purified by silica gel column chromatography and argentation‐silica gel column chromatography. This led to the isolation of three major fractions: fraction I, fraction II, and fraction III. The major steryl esters of fractions I and II were identified by gas chromatography, gas chromatography‐mass spectroscopy, and proton nuclear magnetic resonance analysis of the intact fraction as well as sterol and fatty acid moieties obtained after base hydrolysis. Identification of the steryl esters was carried out by mass spectra comparisons with steryl ester standards synthesized in the laboratory and comparison with mass spectra libraries (Wiley and NIST) by mass fragmentography. Fraction I contained primarily the palmitate, stearate, and eicosanoate esters of α‐ and β‐amyrin. Fraction II consisted mainly of the palmitate, stearate, and eicosanoate esters of tirucalla‐7,24‐dien‐3β‐ol and lupeol.