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Chemical Structure| 2309-07-1 Chemical Structure| 2309-07-1
Chemical Structure| 2309-07-1

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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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Product Citations

Product Citations

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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Product Details of Ferulic acid methyl ester

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

Safety of Ferulic acid methyl ester

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Ferulic acid methyl ester

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2309-07-1 ]

[ 2309-07-1 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 13220-33-2 ]
  • [ 2309-07-1 ]
  • (E)-methyl 3-(3-methoxy-4-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; at 0℃; for 0.5h; To a solution of methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (2.00 g, 9.61 mmol, 1.0 equiv.), l-methylpyrrolidin-3-ol (1.17 g, 11.5 mmol, 1.2 equiv.) andtriphenylphosphine (3.02 g, 11.53 mmol, 1.20 equiv.) in tetrahydrofuran (10 mL) at 0°C was added diisopropylazodicarboxylate (2.33 g, 11.5 mmol, 1.2 equiv.) over 30 minutes. The reaction mixture was diluted with IN hydrochloric acid (50 mL) and extracted with ethyl acetate (3 x 50 mL), the aqueous layer was adjusted to pH = 8 with IN sodium hydroxide solution and extracted with ethyl acetate (3 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuo to give the desired product as a yellow oil (2.50 g, 89percent) which was used without further purification; 1H NMR (CDC13, 400 MHz) delta7.62 (d, J = 16.0 Hz, 1H), 7.05 (d, = 8.0 Hz, 1H), 7.04 (s, 1H), 7.76 (d, = 8.0 Hz, 1H), 6.30 (d, = 16.0 Hz, 1H), 4.89 - 4.85 (m, 1H), 3.87 (s, 3H), 3.79 (s, 3H), 2.95 - 2.92 (m, 1H), 2.80 - 2.76 (m, 2H), 2.55 - 2.53 (m, 1H), 2.39 (s, 3H), 2.38 - 2.35 (m, 1H), 2.05 - 2.01 (m, 1H).
  • 3
  • [ 13220-33-2 ]
  • [ 2309-07-1 ]
  • (E)-3-(3-methoxy-4-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylic acid [ No CAS ]
 

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