ETHYL HYDROCAFFEATE synthesis

6synthesis methods

Product Name:ETHYL HYDROCAFFEATE
CAS Number:3967-57-5
Molecular formula:C11H14O4
Molecular Weight:210.23

23795-02-0 Synthesis

23795-02-0
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3967-57-5
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Yield:3967-57-5 98%

Reaction Conditions:

with Agaricus bisporus;oxygen in aq. phosphate buffer;dichloromethane at 25; pH=7; for 24 h;Reagent/catalyst;

Steps:

4.8 Oxidation of phenols and esters derivatives

General procedure: The reactions were performed under both homogeneous and heterogeneous conditions in CH₂Cl₂/buffer. As a general procedure, phenol (0.05mmol), tyrosinase (600IU) and the optimal amount of the Na-phosphate buffer 0.1M, pH 7 (CH₂Cl₂/buffer ratio ca. 1:0.1) were suspended in CH₂Cl₂ (2.5mL) at 25°C for 24h, and the mixture stirred under O₂ atmosphere. The reactions were monitored by thin layer chromatography (TLC, n-hexane/EtOAc=2.0:1.0). After the disappearance of the substrate, the organic layer was recovered (eventually after filtration for immobilized enzyme), and evaporated under reduced pressure. The crude was treated with Na₂S₂O₄ in equal volume of H₂O and THF (2.0mL) with stirring for 5min. The mixture was diluted with EtOAc (4.0mL) and separated from H₂O. The organic layer was dried on anhydrous Na₂SO₄ and evaporated under reduced pressure. When necessary the crude was purified by flash-chromatography. The products were characterized by ¹H and ¹³C NMR, GC-MS (after silylation) and Elemental Analysis. GC-MS analysis was performed on a GC-MS QP5050 Shimadzu apparatus using an SPB column (25m×0.25mm and 0.25mm film thickness) and an isothermal temperature profile of 100°C for 2min, followed by a 10°Cmin^-¹ temperature gradient to 280°C for 25min. The injector temperature was 280°C. Chromatography-grade helium was used as the carrier gas with a flow of 2.7 mL×min^-¹. Mass spectra were recorded with an electron beam of 70eV. Quantitative analyses were performed by using dodecane as the internal standard. MS values are referred to full silylated derivatives with the only exception of 3c and 3d.

References:

Bozzini, Tiziana;Botta, Giorgia;Delfino, Michela;Onofri, Silvano;Saladino, Raffaele;Amatore, Donatella;Sgarbanti, Rossella;Nencioni, Lucia;Palamara, Anna Teresa [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 24,p. 7699 - 7708]

64-17-5 Synthesis