docosyl trans-ferulate | 101927-24-6

• 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
• 英文名称: docosyl trans-ferulate
• 英文别名: docosyl ferulate；trans-docosanoylferulate；trans-docosanyl ferulate；docosyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 101927-24-6
• 化学式: C₃₂H₅₄O₄
• 分子量: 502.778
• InChiKey: USNYNNITUQSEEV-SHHOIMCASA-N

物化性质

• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  36
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  docosyl trans-ferulate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 生成 docosyl dihydroferulate
  参考文献：
  名称：

  Chemical Constituents of the Pericarp ofPlatycladus orientalis

  摘要：

  AbstractIn previous papers, we have reported two new compounds, 15‐hydroxypinusolidic acid and platydiol, from the pericarp of Platycladus orientalis. In addition to the above compounds, the isolation and identification of twenty‐one compounds from the same source are described. Their structures were determined on the basis of spectral evidence as well as direct comparison with authentic samples. These compounds included four fatty alcohols and acids, three monolignols, one sesquiterpene, nine diterpenes, two steroids, one flavone, and one sugar. Among these, docosyl 3‐hydroxyferulate is a new compound. And docosyl trans‐ and cis‐ferulates were isolated in pure form.

  DOI：

  10.1002/jccs.199900110
• 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 docosyl trans-ferulate
  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

• Methods, compositions and compounds for the treatment of prostatic
  申请人：Inverni Della Beffa SpA

  公开号：US04709076A1

  公开（公告）日：1987-11-24

  Unsaturated esters of formula I ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, which are the same or different to one another, represent hydrogen, hydroxyl, methoxyl or acetoxyl; n is between 13 and 25; are useful in the treatment of prostatic hyperplasia or hypertrophy.

  公式I的不饱和酯物 其中R1、R2和R3是相同或不同的氢、羟基、甲氧基或乙酰氧基；n介于13和25之间。这些酯物在前列腺增生或肥大的治疗中是有用的。
• 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.
• LAVER, MURRAY L.;FANG, HENRY H. -L., J. AGR. AND FOOD CHEM., 37,(1989) N, C. 114-116
  作者：LAVER, MURRAY L.、FANG, HENRY H. -L.

  DOI：——

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

  DOI：——

  日期：——