Vanillic acetone is a synthetic raw material for a variety of psychotropic drugs and various new antimalarial drugs.
It is often used as a cardiotonic and diuretic in medicine. Vanillic acetone is currently recognized as a specific nicotinamide adenine dinucleotide
oxidase inhibitor. Nicotinamide adenine dinucleotide phosphate (NADPH) oxidase and xanthine oxidase are the main chemical sources of free
radicals during myocardial reperfusion. Therefore, inhibiting their activity and reducing the generation of free radicals may alleviate reperfusion injury.
In this experiment, the use of NADPH oxidase inhibitor vanillic acetone can protect the myocardium of reperfused rats. This protection is related to
its inhibition of NADPH oxidase activity and reduction of superoxide anion and peroxynitrite free radical generation mediated by it. |
Vanillinone can protect the myocardium by inhibiting the activity of NADPH oxidase, reducing the free radical generation and
neutrophil infiltration mediated by it, protecting the heart function, reducing myocardial cell apoptosis, and playing an effective
therapeutic role in myocardial reperfusion injury. |
Vanillinone, also known as vanilla acetophenone and acetyl vanillone, has a weak vanilla smell. It is not only used in the spice industry,
but also an important organic synthesis raw material. It can be used to synthesize psychotropic drugs such as iloperidone
and a variety of new antimalarial drugs.It is also a commonly used antioxidant and is currently recognized as a specific nicotinamide
adenine dinucleotide oxidase inhibitor.It is also commonly used as a cardiotonic and diuretic in medicine. |
In the reaction bottle, add 25mL of anhydrous ethanol, 2.0mL (18.0mmol) of guaiacol, 5.0g (36.2mmol) of anhydrous potassium carbonate,
0.3g (2.0mmol) of sodium iodide and 3.2mL (35.4mmol) of n-propane bromide in sequence and stir under reflux for 10h.
Filter and evaporate under reduced pressure to remove ethanol and excess n-propane bromide, add 40mL of dichloromethane and 30mL of 1mol-L-1 sodium hydroxide solution,
separate the organic phase with water (2x 25mL) was washed, dried over anhydrous magnesium sulfate,and rotary evaporation was performed
to obtain 12.86g of yellow liquid with a yield of 95.3%; 25mL and 11.5g (9.0mmol) of dichloromethane were addedto the reaction flask,
and 2.5g (18.3mmol) of anhydrous zinc chloride was added under stirring,and the mixture [dichloromethane (2.0mL) + acetic anhydride (1.7mL, 18.0mmol)] was added dropwise,
and the temperature was slowly raised to room temperature for 4h after the addition. Add 40mL of 1mol-L-1 hydrochloric acid,
extract the aqueous phase with dichloromethane (2x30mL), combine the extracts, wash with water (2×30mL), dry with anhydrous magnesium sulfate,
and evaporate to obtain 1.84g of yellow liquid mixture, with a yield of 97.9% and a purity of 99.1%; add 16mL of
dichloromethane and 1.0g (4.8mmol) of a mixture of isomers 3-methoxy 4-n-propoxy acetophenone and 3-propoxy 4-methoxy acetophenone in the reaction bottle
in sequence and stir until completely dissolved (5min); add 1.4g (10.5mmol) of anhydrous aluminum chloride and react at 35℃ for 4h.
Pour into 1mol-L-1 ammonium chloride solution (25mL), extract the aqueous phase with dichloromethane (2x30mL), combine the extracts, evaporate to obtain solvent,
and separate and purify by silica gel column chromatography [eluent: V (petroleum ether): V (ethyl acetate) = 10:1 to obtain off-white solid vanillyl acetone. |
