12-methoxymethoxydodecanal | 518333-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-methoxymethoxydodecanal
• 英文别名: 13,15-Dioxahexadecanal；12-(methoxymethoxy)dodecanal
• CAS: 518333-10-3
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: KGMSZGNFQPVHLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-methoxymethoxydodecanal 在 盐酸 、 重铬酸吡啶 、 pyridine-SO3 complex 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 1.0h， 生成 (E)-12-tetradecenoic acid
  参考文献：
  名称：

  Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity

  摘要：

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.001
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 吡啶-N-氧化物 、 碳酸氢钠 、 对甲苯磺酸 、 lithium bromide 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 12-methoxymethoxydodecanal
  参考文献：
  名称：

  Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes

  摘要：

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.

  DOI：

  10.1021/jo0267100

文献信息

• Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg2+/Mn2+-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma
  作者：Hideki Kawashima、Naoki Toyooka、Takuya Okada、Huy Du Nguyen、Yuya Nishikawa、Yuka Miura、Nana Inoue、Ken-ichi Kimura

  DOI：10.3390/md17070410

  日期：——

  Diverse non-methylene-interrupted (NMI) fatty acids (FAs) with odd-chain lengths have been recognized in triacylglycerols and polar lipids from the ovaries of the limpet Cellana toreuma, however their biological properties remain unclear. In this study, two previously unreported odd-chain NMI FAs, (12Z)-12,16-heptadecadienoic (1) and (14Z)-14,18-nonadecadienoic (2) acids, from the ovary lipids of C. toreuma were identified by a combination of equivalent chain length (ECL) values of their methyl esters and capillary gas chromatography-mass spectrometry (GC-MS) of their 3-pyridylcarbinol derivatives. On the basis of the experimental results, both 1 and 2 were synthesized to prove their structural assignments and to test their biological activity. The ECL values and electron impact-mass (EI-MS) spectra of naturally occurring 1 and 2 were in agreement with those of the synthesized 1 and 2. In an in vitro assay, both 1 and 2 activated protein phosphatase, Mg2+/Mn2+-dependent 1A (PPM1A) up to 100 μM in a dose-dependent manner.

  来自巴石螺卵巢的三酰甘油和极性脂质中已经发现了多种不含亚甲基间断(NMI)的奇数碳链长度脂肪酸(FA)，但它们的生物学特性仍不清楚。本研究通过相当链长(ECL)值的甲酯和毛细管气相色谱-质谱(GC-MS)的3-吡啶甲醇衍生物鉴定出了巴石螺卵巢脂质中两种未报道的奇数碳链NMI FA，即(12Z)-12,16-庚二烯酸(1)和(14Z)-14,18-十九二烯酸(2)。在实验结果的基础上，合成了1和2来证明它们的结构分配和测试它们的生物活性。天然存在的1和2的ECL值和电子轰击质谱(EI-MS)谱与合成的1和2一致。在体外实验中，1和2均以剂量依赖的方式使蛋白磷酸酶、Mg2+/Mn2+依赖型1A(PPM1A)活化高达100μM。
• Pyrimidine nucleoside derivatives having anti-tumor activity, their preparation and use
  申请人：Sankyo Company Limited

  公开号：EP0536936A1

  公开（公告）日：1993-04-14

  Compounds of formula (I): [in which: R¹, R² and R³ are the same or different and each represents a hydrogen atom, an optionally substituted alkanoyl group or an alkenylcarbonyl group, provided that at least one of R¹, R² and R³ represents an unsubstituted alkanoyl group having from 5 to 24 carbon atoms, said substituted alkanoyl group or said alkenylcarbonyl group; and one of R⁴ and R⁵ represents a hydrogen atom and the other represents a cyano group]; have valuable anti-tumour activity.

  式子（I）的化合物：[其中：R¹、R²和R³相同或不同，每个代表氢原子、可选取代的脂肪酰基团或烯基羰基团，前提是至少有一个R¹、R²和R³代表有5到24个碳原子的未取代脂肪酰基团，或者是所述取代的脂肪酰基团或所述烯基羰基团；R⁴和R⁵中的一个代表氢原子，另一个代表氰基]，具有有价值的抗肿瘤活性。
• US5691319A
  申请人：——

  公开号：US5691319A

  公开（公告）日：1997-11-25
• Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes
  作者：Gemma Villorbina、Lidia Roura、Francisco Camps、Jesús Joglar、Gemma Fabriàs

  DOI：10.1021/jo0267100

  日期：2003.4.1

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.
• Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity
  作者：Haruhisa Kikuchi、Kazunori Sasaki、Jun'ichi Sekiya、Yasuo Maeda、Aiko Amagai、Yuzuru Kubohara、Yoshiteru Oshima

  DOI：10.1016/j.bmc.2004.04.001

  日期：2004.6

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.