Structure of Ferulic acid methyl ester
CAS No.: 2309-07-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Methyl Ferulate is a naturally-occurring phenolic with antioxidant activities and inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages.
Synonyms: Methyl ferulate; Methyl 4'-hydroxy-3'-methoxycinnamate
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Impacts of Sulfur Impurity and Acid Pretreatment on Catalytic Depolymerization of Corn Cob Lignin
Mark, Nakisha P ; Singh, Sandip K ; Uchagawkar, Anoop ; Hagberg, Erik ; Binder, Thomas ; Subramaniam, Bala
Abstract: When fractionating corn cobs using the acetosolv process, the type of acid catalyst and their concentrations significantly affect the structure of the resulting lignin fraction, as well as its catalytic deconstruction to aromatic monomers. Gel permeation chromatography (GPC) results show that the average molecular weight (∼55,750 g/mol) of the sulfuric acidpretreated corn cob lignin (H2SO4-CCL) is much greater than that (∼39,400 g/mol) of hydrochloric acid-pretreated CCL (HCl-CCL) at similar acid concentrations, suggesting increased condensation reactions when using sulfuric acid. Furthermore, a significant amount of bound sulfur content (∼2900 ppm) was measured in H2SO4-CCL. This sulfur presence poisons the Pd/C catalyst used in the downstream catalytic conversion of the lignin in methanol to form monolignols and derivatives thereof. X-ray photoelectron spectroscopy (XPS) results reveal the presence of both sulfide and sulfate groups on the surface Pd sites, rendering them inactive and amenable to possible leaching. Elemental mapping of spent catalysts using scanning transmission electron microscopy-high angle annular dark field (STEM-HAADF)/energy-dispersive X-ray (EDX) technique corroborate the overlapping presence of Pd, S, and O in the micrographs. 2D 1H/13C HSQC nuclear magnetic resonance (NMR) spectroscopy reveals that the use of H2SO4 preserves aryl ether linkages only at low concentrations. In contrast, the use of HCl in the acetosolv process preserves such linkages even at higher concentrations while also mitigating sulfur poisoning of the Pd/C catalyst. Consequently, the yield of aromatic monomers during catalytic fractionation of HCl-CCL was doubled compared to that of H2SO4-CCL under identical operating conditions.
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| CAS No. : | 2309-07-1 |
| Formula : | C11H12O4 |
| M.W : | 208.21 |
| SMILES Code : | O=C(OC)/C=C/C1=CC=C(O)C(OC)=C1 |
| Synonyms : |
Methyl ferulate; Methyl 4'-hydroxy-3'-methoxycinnamate
|
| MDL No. : | MFCD00017208 |
| InChI Key : | AUJXJFHANFIVKH-GQCTYLIASA-N |
| Pubchem ID : | 5357283 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
|
Cell Line
|
Concentration | Treated Time | Description | References |
| Bone marrow-derived macrophages (BMDMs) | 50 µg/ml | 18 h | CA significantly inhibited non-canonical pyroptosis, reducing LDH release and IL-1β secretion | MedComm (2020). 2023 Apr 20;4(3):e255. |
| RAW264.7 cells | 50 µg/ml | 18 h | CA significantly inhibited caspase-11 inflammasome-mediated non-canonical pyroptosis, reducing LDH release and PI uptake | MedComm (2020). 2023 Apr 20;4(3):e255. |
| J774A.1 macrophages | 12.5-100 µg/ml | 18 h | CA significantly inhibited NLRP3 inflammasome-mediated canonical pyroptosis, reducing LDH and IL-1β release | MedComm (2020). 2023 Apr 20;4(3):e255. |
| Caco-2 cells | 0-500 μM | 24 h | To evaluate the effect of ferulic acid methyl ester on cell viability, results showed no significant effect on cell survival at 500 μM concentration for 24 h. | Antioxidants (Basel). 2022 Jul 26;11(8):1448. |
| Human retinal endothelial cells (HRECs) | 0.5mg/ml | 16 h | To evaluate the effect of FA-treated microglial conditioned medium on HRECs migration and tube formation. Results showed that FA-treated microglial conditioned medium significantly inhibited HRECs migration and tube formation. | Front Immunol. 2022 Sep 2;13:976729. |
| BV2 murine microglial cell lines | 0.5mg/ml | 18 h | To evaluate the regulatory effect of FA on BV2 cell polarization under hypoxic conditions. Results showed that FA significantly reduced iNOS+ M1 microglia and increased Arg1+ M2 microglia, decreased pro-inflammatory cytokines TNF-α and IL-6 expression, and increased anti-inflammatory cytokine IL-10 expression. | Front Immunol. 2022 Sep 2;13:976729. |
| Primary mouse hippocampal neurons | 5 and 10 μM | 48 h | To evaluate the protective effect of ferulic acid methyl ester on Aβ-induced reduction of synaptic proteins. The results showed that pretreatment with ferulic acid methyl ester significantly alleviated the Aβ-induced reduction of GluN2B and p-Y1472 GluN2B, as well as PSD-95 and synapsin1. | Neurotherapeutics. 2023 Jul;20(4):1081-1108. |
| skeletal stem cells | 30 μM | 24 h | Ferulic acid significantly rescued the radiation-induced impairment of SSCs by activating the p38/MAPK and ERK/MAPK pathways, restoring their proliferation and osteogenic differentiation capabilities. | Stem Cells Transl Med. 2021 Aug;10(8):1217-1231. |
| Mouse tracheal epithelial cells (MTECs) | 200 μM | 24 h | Evaluate the effect of ferulic acid on ENaC activity, results showed that ferulic acid reversed LPS-induced reduction of ENaC activity | Respir Res. 2021 Dec 4;22(1):308. |
In Vivo:
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Species
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Animal Model
|
Administration | Dosage | Frequency | Description | References |
| Rats | Insomnia model | Oral | 40 mg/kg | Single dose | To evaluate the effect of SMEDDS on the pharmacokinetics and tissue distribution of ferulic acid in rats. Results showed that SMEDDS significantly increased the bioavailability of ferulic acid, reduced renal distribution, and increased brain distribution. | Int J Nanomedicine. 2020 Mar 25;15:2059-2070 |
| C57BL/6 mice | High-fat diet-induced obesity model | Dietary supplementation | 50 mg/kg | Continued for 8 weeks | To evaluate the protective effect of ferulic acid methyl ester on intestinal inflammation, results showed that ferulic acid methyl ester reduced high-fat diet-induced inflammatory responses and enhanced intestinal barrier function. | Antioxidants (Basel). 2022 Jul 26;11(8):1448. |
| C57BL/6J mice | Oxygen-induced retinopathy (OIR) model | Intragastric administration | 50 mg/kg | Twice daily from P12 to P17 | To evaluate the inhibitory effect of FA on retinal neovascularization in the OIR model and its regulatory effect on microglia/macrophage polarization. Results showed that FA significantly reduced the area of retinal neovascular clusters, decreased the number of neovascular endothelial cells, and promoted reparative angiogenesis. Additionally, FA shifted microglia/macrophage polarization from pro-inflammatory M1 to anti-inflammatory M2 phenotype and alleviated inflammatory responses. | Front Immunol. 2022 Sep 2;13:976729. |
| APP/PS1 transgenic mice | Alzheimer's disease model mice | Drinking water | 20 mg/kg | Once daily for 30 days | Ferulic acid methyl ester counteracted ET1-mediated vasoconstriction by binding to ETRA, preventing reductions in hippocampal capillary density and diameter, and ameliorating Aβ plaque deposition and spatial memory deficits. | Neurotherapeutics. 2021 Apr;18(2):1064-1080 |
| APP/PS1 transgenic mice | Alzheimer's disease model | Oral administration via drinking water | 50 mg/kg | Once daily for 4 months | To evaluate the ameliorative effect of ferulic acid methyl ester on cognitive and behavioral deficits in APP/PS1 mice. The results showed that long-term administration of ferulic acid methyl ester significantly improved spatial learning and memory, anxiety-like behavior, and cognitive function in APP/PS1 mice. | Neurotherapeutics. 2023 Jul;20(4):1081-1108. |
| C57BL/J male mice | LPS-induced tracheal injury model | Intraperitoneal injection | 100 mg/kg | 12 hours before and 12 hours after LPS treatment | Evaluate the protective effect of ferulic acid on tracheal injury, results showed that ferulic acid improved tracheal pathological changes and up-regulated ENaC expression | Respir Res. 2021 Dec 4;22(1):308. |
Tags: Ferulic acid methyl ester | Methyl ferulate | p38 MAPK | Autophagy | COX-2 inhibitor | free radical scavenging | p-p38 | p-JNK | 2309-07-1
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