lup-12,20(29)-dien-3β-olyl hexadecanoate

• 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: lup-12,20(29)-dien-3β-olyl hexadecanoate
• 英文别名: lupeol palmitate；lupeolyl palmitate；lupenic palmitate；Lupenylpalmitat；[(1R,3aR,5aS,5bR,7aR,9S,11aR,11bR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysen-9-yl] hexadecanoate
• 化学式: C₄₆H₇₈O₂
• 分子量: 663.124
• InChiKey: RTBYELMSYZHHPE-WHTPURSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  lup-12,20(29)-dien-3β-olyl hexadecanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 lupeol
  参考文献：
  名称：

  Two new triterpenoids fromCichorium intybusL. roots

  摘要：

  Two new triterpenic constituents characterized as lupenic arabinopalmitate [lup-12,20( 29)-dien-3 beta-ol-3 beta-L-arabinofuranosyl-2'-hexadecanoate] (1) and lupenic palmitate [lup-12,20(29)-dien-3 beta-olyl hexadecanoate] (2) and an aliphatic delta-lactone [4 beta- pent-2-enylolactone)-hexatriacontane] (4) have been isolated for the first time from the methanolic extract of the roots of Cichorium intybus L. (Asteraceae) along with the known compound glycery-1-stearyl-2-linolenyl phosphate 3. The structures of all these phytoconstituents have been established by spectral data analysis and chemical reactions.

  DOI：

  10.1080/10286020.2011.619181
• 作为产物：
  描述：

  羽扇豆醇 、 棕榈酸 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， 以95%的产率得到lup-12,20(29)-dien-3β-olyl hexadecanoate
  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