133882-79-8

Basic information

• Product Name: Eicosyl ferulate
• Synonyms: Eicosyl ferulate;E-Ferulic acid eicosyl ester;n-Eicosyl-trans-ferulate;trans-Eicosyl ferulate;Icosyl 3-(4-hydroxy-3-Methoxyphenyl)acrylate
• CAS NO: 133882-79-8
• Molecular Formula: C₃₀H₅₀O₄
• Molecular Weight: 474.7156
• Mol File: 133882-79-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Eicosyl ferulate(CAS DataBase Reference)
• NIST Chemistry Reference: Eicosyl ferulate(133882-79-8)
• EPA Substance Registry System: Eicosyl ferulate(133882-79-8)

Safety Data

• Hazardous Substances Data: 133882-79-8(Hazardous Substances Data)

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 629-96-9 n-eicosanol 
• 145205-03-4 (E)-3-<3-Methoxy-4-(tetrahydropyran-2-yloxy)phenyl>prop-2-enoic acid 
• 91471-08-8 3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde 

Relevant articles and documents

Ferulic Acid Esters and Withanolides: In Search of Withania somnifera GABAA Receptor Modulators

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 GABAA 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 GABAA receptor inhibitory postsynaptic currents with an IC50 value of 7.9 μM. These results, by showing an ability to modulate the GABAA 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

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 (C12-caffeate), 11 (C16-caffeate), 21 (C 8-ferulate), and 23 (C12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 μg/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 μg/ mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 μg/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 μg/ 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 (C4-C 12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C3-C8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 μg/mL. Long-chain caffeates 11-14 (C 16-C22) and short-chain ferulates 15-20 (C 3-C5) were the most active in lipid peroxidation inhibition and showed 60-70% activity at 5 μg/mL concentration.

Alkyl ferulates in wound healing potato tubers.

Seven ferulic acid esters of 1-alkanols ranging in carbon length from C16 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 th