Long effective curcumin derivative and preparation method thereof
A curcumin derivative, the technology of curcumin, which is applied in the directions of non-active ingredient medical preparations, active ingredients-containing medical preparations, drug combinations, etc., can solve the problem of short half-life, low bioavailability, water solubility and ester solubility. Poor and other problems, to achieve the effect of increasing ester solubility and improving bioavailability
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Embodiment 1
[0040] The long-acting curcumin derivative of the present invention is to adopt the esters formed by the esterification reaction of the saturated fatty acid substances of curcuminoids and C1-C50, and its reaction structural formula can be expressed as follows:
[0041]
[0042] where n=1~49
[0043] By the generated curcumin alkyl ester of above-mentioned reaction, its preparation method comprises the steps:
[0044] Weigh 2-4 mmol of curcuminoids, dissolve them in 50 ml of dioxane, add 0.3-0.73 g of pyridine, then add 3.6-8.60 mmol of capric acid dropwise into the system, and react in an ice-water bath for 2 hours , the reaction process was monitored by TLC, developed with 3:1 chloroform and ethyl acetate.
[0045] Pour the above product into 40 ml of petroleum ether, filter and dissolve the precipitate in 30 ml of ethyl acetate, wash twice with 20 ml of 1mol / L hydrochloric acid solution, wash once with saturated sodium carbonate solution, add 3 g Anhydrous sodium sulfat...
Embodiment 2
[0050] The long-acting curcumin derivative of the present invention is to adopt the esters formed by the esterification reaction between curcuminoids and C1-C50 saturated fatty acyls, and its reaction structure formula can be expressed as follows:
[0051]
[0052] Wherein n=1~49, in CnH2n+1COOR (R is a halogen atom such as Cl, Br, I, etc.).
[0053] By the generated curcumin alkyl ester of above-mentioned reaction, its preparation method comprises the steps:
[0054]Weigh 2-4 mmol of curcuminoids, dissolve in 50 ml of dioxane, add 0.3-0.73 g of pyridine, then add 3.6-8.60 mmol of decanoyl chloride dropwise into the system, and react in an ice-water bath for 2 hours , the reaction process was monitored by TLC, developed with 3:1 chloroform and ethyl acetate.
[0055] Pour the above product into 40 ml of petroleum ether, filter and dissolve the precipitate in 30 ml of ethyl acetate, wash twice with 20 ml of 1mol / L hydrochloric acid solution, wash once with saturated sodium ...
Embodiment 3
[0061] The long-acting curcumin derivative of the present invention is to adopt the esters formed by the esterification reaction of curcuminoids and C1-C50 unsaturated fatty acids or their acyls, and its reaction structural formula can be expressed as follows:
[0062]
[0063] Wherein n=1~49, in CnH2(n-1) COOR (R is a halogen atom such as Cl, Br, I etc.).
[0064] The curcumin alkenyl ester generated by the above reaction equation, its preparation method may further comprise the steps:
[0065] Weigh 2-4mmol of curcuminoids, 140ml of dichloromethane and 73.4ml of pyridine, add dropwise a solution of 0.229mol of linoleoyl chloride in 100ml of dichloromethane within 1h under stirring at room temperature, and keep the reaction at 50°C for 3h. The reaction process was monitored by TLC, developed with 3:1 chloroform and ethyl acetate, and after reaching the end point, the reaction mixture was transferred to a mixed solution of 200ml of water and 200ml of dichloromethane under s...
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