CAS number: 345909-34-4
Molecular formula: C15H10O6
Molecular weight: 286.238
EINECS Number: 208-434-4
Source: Synthetic/Natural
Latin name: Cotinus coggygria Scop.
Extraction part: stem
Product properties: yellow powder
Product specification: 10%-98%
Detection method: area normalization method, external standard method
Physical properties: yellow needle crystal (dilute ethanol), melting point 330°C (decomposition). Soluble in ethanol, acetone and acetic acid. Almost insoluble in water, ether, benzene, chloroform and petroleum ether. Melting point 348°C, bright yellow fine needle crystal, melting point > 300°C
The synthetic method of fisetin comprises the following steps:
Step 1. Produces a white mixture
1.1) Stir 100ml of 2-butanone and 24g of benzyl chloride evenly, then add 8g of 2,4-dihydroxyacetophenone and 25g of anhydrous K2CO3, stir, heat up and reflux for 12 hours, then add 100ml of water stir;
1.2) After the reaction is finished, extract with dichloromethane, evaporate the solvent by rotary evaporation, and collect the residue; and recrystallize the residue with 20ml of methanol to obtain 13.6g of white mixture powder with a yield of 75.1%.
Step 2. Generate 3', 4'-dihydroxy-7-benzylchalcone
2.1) Dissolve 13.6g of white mixture powder and 13.5g of protocatechualdehyde into 100ml of absolute ethanol, add 120g of potassium hydroxide solution with a mass concentration of 30%, stir under nitrogen protection, and heat up and reflux for about 20h , cooled and poured into 150g of ice water to quench the reaction;
2.2) acidify the solution obtained in step 2.1) to a pH of 3 with 1:1 (volume ratio) hydrochloric acid with a mass concentration of 18%, and precipitate an orange solid, which is filtered;
2.3) Wash the orange-yellow solid obtained by filtering in step 2.2) with water to obtain a crude product of 3',4'-dihydroxy-7-benzylchalcone, and recrystallize it with 500ml of methanol to obtain 22.95g of orange-yellow needles 3', 4'-dihydroxy-7-benzylchalcone as crystals with a yield of 85.1%.
Step 3. Generate 3', 4', 7-trihydroxychalcone
22.95g of 3', 4'-dihydroxy-7-benzylchalcone was dissolved in 100ml of ethyl acetate, and under the catalysis of palladium carbon, it was reduced by adding hydrogen until it could no longer absorb hydrogen (i.e. the pressure no longer drop), filtered and distilled off the solvent to obtain 21.573g of 3',4',7-trihydroxychalcone with a yield of 94% and a purity of 95%.
Step 4. Generate fisetin
4.1) Add 21.573g of 3', 4', 7-trihydroxychalcone to a mixed solvent of 140ml of dichloromethane-acetone (V:V=4:3), add 200ml of sodium carbonate/bicarbonate Sodium buffer solution (configured by 8g sodium carbonate, 8g sodium bicarbonate and 200ml water), and vigorously stirred at room temperature;
4.2) To the solution obtained in step 4.1), slowly add 140ml of an aqueous solution of potassium hydrogensulfate compound salt (formed by 12g of potassium hydrogensulfate compound salt and 140ml of water) dropwise for the first time, and the addition is completed after 5h, and react at room temperature 16h, then the aqueous solution of 140ml potassium bisulfate compound salt (configured by 12g potassium hydrogensulfate compound salt and 140ml of water) is slowly added dropwise for the second time, after 5h dropwise addition, continue to react at room temperature for 16h, keep the reaction system The pH is 9, and the two reactions are detected by thin-layer chromatography, and the disappearance of raw material spots is the end point;
4.3) After the reaction is over, let it stand still, use dichloromethane to extract the organic phase, wash the organic phase with saturated sodium thiosulfate and saturated brine for 3 times, dry with anhydrous magnesium sulfate, filter the filtrate, and add to the filtrate 50 mg of p-toluenesulfonic acid was added, and the reaction was stirred at room temperature for 1 h. After the reaction was completed, the solvent was recovered and recrystallized using anhydrous methanol or dichloromethane to obtain 20.86 g of yellow solid fisetin with a yield of 96.7%. Purity 98% (liquid phase).
The process of extracting fisetin from cotinus sumac, the process steps are:
(1) Pulverize the raw material of sumac sumac, a plant of Anacardaceae, and add ethanol for pretreatment;
(2) Ultrasonic extraction, filtration, and concentration of the filtrate under reduced pressure;
(3) Adsorption on the macroporous resin on the concentrated solution, washing with water to remove impurities, elution with ethanol, and collecting the eluent;
(4) After the eluent is concentrated and dried, it is separated and purified by high-speed countercurrent chromatography;
(5) Crystallization.
The advantage is that the process is simple, the operation is safe and convenient, and it is suitable for industrial production.
The efficacy and function of fisetin:
Effective Antioxidant
Fisetin has strong antioxidant capacity. Antioxidation refers to the ability to scavenge free radicals and inhibit the production of free radicals, which are one of the main causes of many diseases. Flavonoids and other active ingredients contained in fisetin have the functions of scavenging free radicals and delaying cell aging.
beauty
Fisetin can also be used for beauty and beauty. The flavonoids and other active ingredients contained in fisetin can promote the body's internal metabolism, maintain sufficient nutrition for the body, and make the skin healthier. At the same time, fisetin can also improve skin elasticity, reduce wrinkles and skin sagging, thereby delaying aging.
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