4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A dilute sulfuric acid solution or aqueous ammonia was dropwise added to the foregoing reaction solution for enzyme-activity determination from which the buffer is omitted (i.e., a solution comprising 50 μl of a 200 mM solution of eugenol in n-octane, 200 μl of a 50 mM aqueous solution of phenazine methosulfate and 675 μl of deionized water) to adjust the pH thereof from 5 to 7 and the resulting mixture is stirred at a temperature ranging from 25 to 55° C. for 15 to 180 minutes. After the completion of the reaction, the coniferyl alcohol is extracted from the reaction solution with an organic solvent such as ethyl acetate, chloroform, methylene chloride or ethyl ether, followed by purification thereof by a means such as silica gel chromatography, reverse phase liquid chromatography or vacuum distillation, optional discoloration with active carbon and vacuum drying to give colorless coniferyl alcohol powder. After the completion of the reaction the coniferyl alcohol is extracted from the reaction solution with an organic solvent such as ethyl acetate, chloroform, methylene chloride or ethyl ether followed by purification phase liquid chromatography or vacuum distillation, optional discoloration with active carbon and vacuum drying

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A dilute sulfuric acid solution or aqueous ammonia was dropwise added to the foregoing reaction solution for enzyme-activity determination from which the buffer is omitted (i.e., a solution comprising 50 μl of a 200 mM solution of eugenol in n-octane, 200 μl of a 50 mM aqueous solution of phenazine methosulfate and 675 μl of deionized water) to adjust the pH thereof from 5 to 7 and the resulting mixture is stirred at a temperature ranging from 25 to 55° C. for 15 to 180 minutes. After the completion of the reaction, the coniferyl alcohol is extracted from the reaction solution with an organic solvent such as ethyl acetate, chloroform, methylene chloride or ethyl ether, followed by purification thereof by a means such as silica gel chromatography, reverse phase liquid chromatography or vacuum distillation, optional discoloration with active carbon and vacuum drying to give colorless coniferyl alcohol powder. After the completion of the reaction the coniferyl alcohol is extracted from the reaction solution with an organic solvent such as ethyl acetate, chloroform, methylene chloride or ethyl ether followed by purification phase liquid chromatography or vacuum distillation, optional discoloration with active carbon and vacuum drying

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dihydroconiferyl aldehyde (DCAL) was synthesized as follows: To a solution of coniferyl alcohol (720 mg, 4 mmol) in methanol (10 ml) was added palladium-charcoal (10%, 100 mg), with the resulting solution stirred under an H2 atmosphere for 4 hours (h) at ambient temperature. After the catalyst was removed by filtration, the resulting solution was evaporated to dryness in vacuo. The resulting residue was dissolved in acetone, subjected to preparative TLC and extracted with acetone; evaporation of the solvent afforded dihydroconiferyl alcohol (DCA, 650 mg, 90%). To the purified DCA (600 mg, 3.3 mmol) in CH2Cl2 (5 ml) was added DMSO (3.4 ml, 36.6 mmol), triethylamine (1 ml, 13.2 mmol), and pyridine sulfur trioxide (1.58 mg, 9.9 mmol), with the resulting mixture stirred for 30 min at ambient temperature. After reaction, the solution was poured into H2O in a separatory funnel, extracted with ether, washed successively with saturated (NH4)Cl, saturated NaHCO3, H2O and saturated NaCl, and finally with NaSO4. The solvent was evaporated and the resulting extract subjected to preparative TLC, with dihydroconiferyl aldehyde extracted with acetone. Evaporation of the solvent afforded dihydroconiferyl aldehyde (202 mg, 1.1 mmol, 33%). After the catalyst was removed by filtration the resulting solution was evaporated to dryness in vacuo The resulting residue was dissolved in acetone extracted with acetone evaporation of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dihydroconiferyl aldehyde (DCAL) was synthesized as follows: To a solution of coniferyl alcohol (720 mg, 4 mmol) in methanol (10 ml) was added palladium-charcoal (10%, 100 mg), with the resulting solution stirred under an H2 atmosphere for 4 hours (h) at ambient temperature. After the catalyst was removed by filtration, the resulting solution was evaporated to dryness in vacuo. The resulting residue was dissolved in acetone, subjected to preparative TLC and extracted with acetone; evaporation of the solvent afforded dihydroconiferyl alcohol (DCA, 650 mg, 90%). To the purified DCA (600 mg, 3.3 mmol) in CH2Cl2 (5 ml) was added DMSO (3.4 ml, 36.6 mmol), triethylamine (1 ml, 13.2 mmol), and pyridine sulfur trioxide (1.58 mg, 9.9 mmol), with the resulting mixture stirred for 30 min at ambient temperature. After reaction, the solution was poured into H2O in a separatory funnel, extracted with ether, washed successively with saturated (NH4)Cl, saturated NaHCO3, H2O and saturated NaCl, and finally with NaSO4. The solvent was evaporated and the resulting extract subjected to preparative TLC, with dihydroconiferyl aldehyde extracted with acetone. Evaporation of the solvent afforded dihydroconiferyl aldehyde (202 mg, 1.1 mmol, 33%). After the catalyst was removed by filtration the resulting solution was evaporated to dryness in vacuo The resulting residue was dissolved in acetone extracted with acetone evaporation of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The yield of coniferyl alcohol was 3226 ppm. This corresponds to 43.5% of theory. In addition, a further 1738 ppm (25% of theory) of ferulic acid were also obtained, as well as 12 ppm of coniferyl aldehyde and 8 ppm of vanillic acid. At the end of the process, 496 ppm (7.3%) of unreacted eugenol were still present.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A dilute sulfuric acid solution or aqueous ammonia was dropwise added to the foregoing reaction solution for enzyme-activity determination from which the buffer is omitted (i.e., a solution comprising 50 μl of a 200 mM solution of eugenol in n-octane, 200 μl of a 50 mM aqueous solution of phenazine methosulfate and 675 μl of deionized water) to adjust the pH thereof from 5 to 7 and the resulting mixture is stirred at a temperature ranging from 25 to 55° C. for 15 to 180 minutes. After the completion of the reaction, the coniferyl alcohol is extracted from the reaction solution with an organic solvent such as ethyl acetate, chloroform, methylene chloride or ethyl ether, followed by purification thereof by a means such as silica gel chromatography, reverse phase liquid chromatography or vacuum distillation, optional discoloration with active carbon and vacuum drying to give colorless coniferyl alcohol powder. After the completion of the reaction the coniferyl alcohol is extracted from the reaction solution with an organic solvent such as ethyl acetate, chloroform, methylene chloride or ethyl ether followed by purification phase liquid chromatography or vacuum distillation, optional discoloration with active carbon and vacuum drying

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dihydroconiferyl aldehyde (DCAL) was synthesized as follows: To a solution of coniferyl alcohol (720 mg, 4 mmol) in methanol (10 ml) was added palladium-charcoal (10%, 100 mg), with the resulting solution stirred under an H2 atmosphere for 4 hours (h) at ambient temperature. After the catalyst was removed by filtration, the resulting solution was evaporated to dryness in vacuo. The resulting residue was dissolved in acetone, subjected to preparative TLC and extracted with acetone; evaporation of the solvent afforded dihydroconiferyl alcohol (DCA, 650 mg, 90%). To the purified DCA (600 mg, 3.3 mmol) in CH2Cl2 (5 ml) was added DMSO (3.4 ml, 36.6 mmol), triethylamine (1 ml, 13.2 mmol), and pyridine sulfur trioxide (1.58 mg, 9.9 mmol), with the resulting mixture stirred for 30 min at ambient temperature. After reaction, the solution was poured into H2O in a separatory funnel, extracted with ether, washed successively with saturated (NH4)Cl, saturated NaHCO3, H2O and saturated NaCl, and finally with NaSO4. The solvent was evaporated and the resulting extract subjected to preparative TLC, with dihydroconiferyl aldehyde extracted with acetone. Evaporation of the solvent afforded dihydroconiferyl aldehyde (202 mg, 1.1 mmol, 33%). After the catalyst was removed by filtration the resulting solution was evaporated to dryness in vacuo The resulting residue was dissolved in acetone extracted with acetone evaporation of the solvent