阿魏酸二十烷基酯 | 133882-79-8

• 物质功能分类: 天然产物 - 苯丙素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 阿魏酸二十烷基酯
• 中文别名: 阿魏酸二十烷酯
• 英文名称: (E)-icosyl 3-(4-hydroxy-3-methoxyphenyl)-acrylate
• 英文别名: E-ferulic acid eicosyl ester；trans-cosanyl ferulate；eicosanyl ferulate；Eicosyl ferulate；icosyl ferulate；4-hydroxy-3-methoxy-trans-cinnamic acid eicosyl ester；icosyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 133882-79-8
• 化学式: C₃₀H₅₀O₄
• 分子量: 474.725
• InChiKey: UBNJQWYYWIBSGN-ZNTNEXAZSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• LogP：
  11.890 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  34
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

制备方法与用途

阿魏酸二十糖酯是一种从马兜铃新鲜根和茎中提取的酚类化合物，能够促进葡萄糖摄取。

反应信息

• 作为反应物：
  描述：

  阿魏酸二十烷基酯 、 sodium hydroxide 、 水 生成 1-二十醇
  参考文献：
  名称：

  BALDE, ALIOU M.;CLAEYS, M.;PIETERS, L. A.;WRAY, V.;VLIETINCK, A. J., PHYTOCHEMISTRY, 30,(1991) N, C. 1024-1026

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 哌啶 、 苯胺 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 16.0h， 生成 阿魏酸二十烷基酯
  参考文献：
  名称：

  Alkyl ferulates in wound healing potato tubers

  摘要：

  Seven ferulic acid esters of 1-alkanols ranging in carbon length from C-16 to C28 were synthesized and an HPLC protocol for their separation developed. Extracts prepared from wound healing potato (Solanum tuberosum) tubers and analysed by HPLC indicated that alkyl ferulate esters begin to accumulate 3-7 days after wound treatment. Of the nine esters identified by EIMS, (including two esters of odd chain length alkanols) hexadecyl and octadecyl ferulates were predominant. Alkyl ferulate esters were restricted to the wound periderm.

  DOI：

  10.1016/0031-9422(92)83695-u

文献信息

• Ferulic Acid Esters and Withanolides: In Search of <i>Withania somnifera</i> GABA_A Receptor Modulators
  作者：Vijay P. Sonar、Benedetta Fois、Simona Distinto、Elias Maccioni、Rita Meleddu、Filippo Cottiglia、Elio Acquas、Sanjay Kasture、Costantino Floris、Daniele Colombo、Claudia Sissi、Enrico Sanna、Giuseppe Talani

  DOI：10.1021/acs.jnatprod.8b01023

  日期：2019.5.24

  Nine compounds, including two undescribed withanolides, withasomniferolides A and B (1 and 2), three known withanolides (3-5), a ferulic acid dimeric ester (6), and an inseparable mixture of three long alkyl chain ferulic acid esters (7-9), were isolated from a GABA(A) receptor positive activator methanol extract of the roots of Withania somnifera. The structures of the isolated compounds were elucidated based on NMR, MS, and ECD data analysis. In order to bioassay the single ferulic acid derivatives, compounds 6-9 were also synthesized. The most active compound, docosanyl ferulate (9), was able to enhance the GABA(A) receptor inhibitory postsynaptic currents with an IC50 value of 7.9 mu M. These results, by showing an ability to modulate the GABA(A) receptor function, cast fresh light on the biological activities of the secondary metabolites of W. somnifera roots.
• Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation
  作者：Bolleddula Jayaprakasam、Mulabagal Vanisree、Yanjun Zhang、David L. Dewitt、Muraleedharan G. Nair

  DOI：10.1021/jf060899p

  日期：2006.7.1

  The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C-12-caffeate), 11 (C-16-caffeate), 21 (C-8-ferulate), and 23 (C-12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 mu g/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 mu g/mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 mu g/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 mu g/mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C-4-C-12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C-3-C-8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 mu g/mL. Long-chain caffeates 11-14 (C-16-C-22) and short-chain ferulates 15-20 (C-3-C-5) were the most active in lipid peroxidation inhibition and showed 6070% activity at 5 mu g/mL concentration.
• VERBINDUNG ZUR ANWENDUNG BEI DER STEIGERUNG VON MENTALER LEISTUNGSFÄHIGKEIT
  申请人：Leibniz-institut Für Neurobiologie (lin) Stiftung

  公开号：EP3713604A1

  公开（公告）日：2020-09-30
• COMPOUND FOR USE IN THE INCREASING OF MENTAL CAPACITY
  申请人：LEIBNIZ-INSTITUT FUER NEUROBIOLOGIE (LIN) STIFTUNG DES OEFFENTLICHEN RECHTS

  公开号：US20200360332A1

  公开（公告）日：2020-11-19

  Compound, stereoisomers, enantiomers or diastereomers thereof, physiologically acceptable salts thereof, mixtures of said compound for use in increasing mental capability, and a pharmaceutical composition. The increasing of mental capability is tested in learning experiments with Drosophila melanogaster larvae or older animals, which are raised with standard feed mash or with different concentrations of FSE-20 in the feed mash. In the learning experiment, the animals are each subjected to one of two inverse training regimens and then subjected to a test. In the training, a first scent was presented with the feed reward to the first group, while a second scent was presented alone to the first group. The second group was trained inversely. In the test of the learning experiment, it was subsequently examined whether the larvae of both groups prefer the first scent or the second scent in a selection situation; thus, their learning and memory capability was determined.
• [DE] VERBINDUNG ZUR ANWENDUNG BEI DER STEIGERUNG VON MENTALER LEISTUNGSFÄHIGKEIT<br/>[EN] COMPOUND FOR USE IN THE INCREASING OF MENTAL CAPABILITY<br/>[FR] COMPOSÉ À UTILISER LORS DE L'AUGMENTATION DE PERFORMANCES INTELLECTUELLES
  申请人：LEIBNIZ INST FUER NEUROBIOLOGIE LIN STIFTUNG DES OEFFENTLICHEN RECHTS

  公开号：WO2019101952A1

  公开（公告）日：2019-05-31

  Beschrieben wird eine Verbindung, deren Stereoisomere, Enantiomere oder Diastereomere, deren physiologisch annehmbaren Salze sowie Mischungen der genannten Verbindung zur Anwendung bei der Steigerung von mentaler Leistungsfähigkeit. Weiterhin wird eine pharmazeutische Zusammensetzung beschrieben. Die Steigerung mentaler Leistungsfähigkeit wird in Lernexperimenten mit Drosophila melanogaster Larven oder älteren Tieren getestet, welche mit Standard-Futterbrei oder mit verschiedenen Konzentrationen von FSE-20 im Futterbrei aufgezogen werden. In dem Lernexperiment wurden die Tiere, je einem von zwei reziproken Trainingsregimen unterzogen und dann einem Test unterzogen. Der ersten Gruppe wurde im Training ein erster Duft (weißes Quadrat) mit der Futterbelohnung (Fruktose) (weißer Kreis mit Längsstreifen) präsentiert, während ein zweiter Duft (schwarzes Quadrat) alleine (weißer Kreis ohne die Längsstreifen) präsentiert wurde. Die zweite Gruppe wurde reziprok trainiert. Im Test des Lernexperiments wurde anschließend untersucht, ob die Larven beider Gruppen in einer Wahlsituation den ersten Duft oder den zweiten Duft bevorzugen und somit ihre Lern- und Gedächtnisleistung (Performance Index) bestimmt.