ipurolic acid methyl ester | 132336-24-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ipurolic acid methyl ester
• 英文别名: methyl (3S,11S)-dihydroxytetradecanoate；methyl (3S,11S)-3,11-dihydroxytetradecanoate
• CAS: 132336-24-4
• 化学式: C₁₅H₃₀O₄
• 分子量: 274.401
• InChiKey: XVHIDNDUMNPTQW-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ipurolic acid methyl ester 在 吡啶 、 chromium trioxide-pyridine complex 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 108.0h， 生成 (S)-11-Oxo-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradecanoic acid methyl ester
  参考文献：
  名称：

  Resin Glycosides. XVIII. Determination by Mosher's Method of the Absolute Configurations of Mono- and Dihydroxyfatty Acids Originated from Resin Glycosides.

  摘要：

  通过酸水解各种树脂糖苷，四种羟基脂肪酸（墨西哥胡椒酸、旋花酸、伊普罗酸和3,11-二羟基十六烷酸）的绝对构型分别被确定为11S、11S、3S、11S和3S、11S，通过莫舍尔法测定。因此，先前由霍罗法定义的墨西哥胡椒酸的R构型被修改为S。

  DOI：

  10.1248/cpb.41.1023
• 作为产物：
  描述：

  (2R,5S,8S,9R,11R,12S,15S,18R,21R)-5,12,15-trihydroxy-11-methyl-6-methylidene-14,20-dioxo-13,19-dioxa-17-thiaheptacyclo[9.7.2.15,8.112,15.01,10.02,8.018,21]docosane-9-carboxylic acid 、 硫酸 生成 ipurolic acid methyl ester
  参考文献：
  名称：

  ONO, MASATERU;NODA, NAOKI;KAWASAKI, TOSHIO;MIYAHARA, KAZUMOTO, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1892-1897

  摘要：

  DOI：

文献信息

• Two New Glycosidic Acids, Quamoclinic Acids G and H, of the Resin Glycosides (Convolvulin) from the Seeds of Quamoclit pennata
  作者：Masateru Ono、Masae Imao、Kazumoto Miyahara

  DOI：10.1248/cpb.58.1232

  日期：——

  Two new glycosidic acids, quamoclinic acids G and H, were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction from the seeds of Quamoclit pennata BOJER. Both compounds are the first examples of bisdesmosides of glycosidic acid having the sugar linkages at C-3 of 3,11-dihydroxytetradecanoic acid (ipurolic acid) as well as at its C-11.

  从 Quamoclit pennata BOJER 种子中的醚不溶性树脂苷（convolvulin）馏分经碱性水解得到的苷酸馏分中分离出了两种新的苷酸，即夸美林酸 G 和 H。这两种化合物都是糖苷酸双二苷的第一个实例，它们在 3,11- 二羟基十四酸（异欧萝酸）的 C-3 和 C-11 处都有糖链。
• Components of Ether-Insoluble Resin Glycoside (Convolvulin) from Seeds of Quamoclit pennata
  作者：Masateru Ono、Yoko Takagi-Taki、Fumiko Honda-Yamada、Naoki Noda、Kazumoto Miyahara

  DOI：10.1248/cpb.58.666

  日期：——

  Alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction of the seeds of Quamoclit pennata BOJER (Convolvulaceae) provided five new glycosidic acids, quamoclinic acids B, C, D, E, and F, along with six organic acids, isobutyric, 2S-methylbutyric, tiglic, 2R,3R-nilic, 7S-hydroxydecanoic, and 7S-hydroxydodecanoic acids. These new compounds were characterized on the basis of spectroscopic data as well as chemical evidence. Quamoclinic acids E and F are the first examples of heptaglycosides of glycosidic acid.

  对 Quamoclit pennata BOJER（旋花科）种子的醚不溶性树脂苷（convolvulin）部分的碱性水解提供了五种新的苷酸、以及六种有机酸：异丁酸、2S-甲基丁酸、tiglic 酸、2R,3R-nilic 酸、7S-羟基癸酸和 7S-hydroxydodecanoic 酸。这些新化合物的特征是基于光谱数据和化学证据。Quamoclinic 酸 E 和 F 是苷酸七糖苷的第一个例子。
• Jalapinoside II, a bisdesmoside resin glycoside, and related glycosidic acids from the officinal jalap root ( Ipomoea purga )
  作者：Elihú Bautista、Mabel Fragoso-Serrano、Rogelio Pereda-Miranda

  DOI：10.1016/j.phytol.2016.07.022

  日期：2016.9

  macrocyclic bidesmoside resin glycoside with purgic acid C as its oligosaccharide core, was isolated by recycle preparative-scale HPLC from the MeOH-soluble extract of Ipomoea purga (Convolvulaceae), the officinal jalap root (⿿Rhizoma Jalapae⿿). This study also reports the complete NMR data assignment for purgic acid C and the structural elucidation of purgic acid D, both glycosidic acids were isolated, in conjunction

  Jalapinoside II是一种以嘌呤酸C为寡糖核心的大环双侧阿糖苷树脂糖苷，通过循环制备型HPLC分离了可药用的Japo根（Ipomoea purga）（Convolvulaceae）的MeOH可溶性提取物（Rhizoma Jalapae）。这项研究还报告了纯净酸C的完整NMR数据分配和纯净酸D的结构解析，在MeOH可溶性树脂糖苷的皂化作用下，将这两种糖苷酸与先前已知的纯净酸A和B分离了。HPLC和13C NMR谱图用作分析工具，用于鉴定商品化的墨西哥斯卡蒙尼树脂。在抗长春碱的人乳腺癌细胞中评估了非细胞毒性Jalapinoside II对多药耐药的逆转因子（RF MCF-7 / Vin +  > 1906）。
• Identification and characterization of organic and glycosidic acids in the crude resin glycoside fraction of Ipomoea lacunosa seeds
  作者：Kazutaka Uemura、Renjyu Murakami、Eiki Kimura、Marina Kai、Nodoka Misuda、Shin Yasuda、Hiroyuki Miyashita、Hitoshi Yoshimitsu、Ryota Tsuchihasi、Masafumi Okawa、Junei Kinjo、Masateru Ono

  DOI：10.1016/j.carres.2024.109048

  日期：2024.2

  extracted from the seeds of I. lacunosa are characterized. Alkaline hydrolysis of the crude resin glycoside fraction obtained from methanolic extract of the seeds yielded three organic acids, namely, 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R-methyl-3R-hydroxybutyric acids, and a glycosidic acid fraction. Acidic hydrolysis of the glycosidic acid fraction yielded hydroxyl fatty acid components

  树脂糖苷常见于旋花科植物中。 Ipomoea lacunosa L.（旋花科）是一种原产于美国的草本藤本植物。该植物的树脂苷尚未被详细研究。在本研究中，对从I. lacunosa种子中提取的粗树脂糖苷部分的成分进行了表征。从种子的甲醇提取物中获得的粗树脂糖苷部分的碱水解产生三种有机酸，即2S-甲基丁酸、( E )-2-甲基丁-2-烯酸和2R-甲基-3R-羟基丁酸，和糖苷酸部分。糖苷酸级分的酸水解产生羟基脂肪酸组分，包括7S-羟基癸酸、11S-羟基十四烷酸、11S-羟基十六烷酸、 3S ，11S-二羟基十四烷酸、 3S ，11S-二羟基十六烷酸和3S ，12 S-二羟基十六烷酸，以及单糖成分，包括d-葡萄糖、 d-奎诺糖、 d-岩藻糖和L-鼠李糖。三甲基甲硅烷基重氮甲烷-己烷处理糖苷酸馏分进一步产生十一种先前未描述的糖苷酸甲酯和两种已知的糖苷酸甲酯。使用各种光谱技术对所得化合物的结构进行了表征。
• Resin glycosides from <i>Porana duclouxii</i>
  作者：Wen-Bing Ding、Dai-Gui Zhang、Chun-Jie Liu、Guan-Hua Li、You-Zhi Li

  DOI：10.1080/10286020.2013.864281

  日期：2014.2.1

  A new intact resin glycoside (3) and two glycosidic acids (1 and 2), all having a common trisaccharide moiety and (11S)-hydroxytetradecanoic acid or (3S,11S)-dihydroxytetradecanoic acid as the aglycone, were obtained from the roots of Porana duclouxii. Their structures were elucidated by spectroscopic analyses and chemical correlations. These compounds represent the first examples of resin glycosides from the genus Porana.