CN114031488A - Method for synthesizing tetrahydrocurcumin - Google Patents
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- CN114031488A CN114031488A CN202111307123.6A CN202111307123A CN114031488A CN 114031488 A CN114031488 A CN 114031488A CN 202111307123 A CN202111307123 A CN 202111307123A CN 114031488 A CN114031488 A CN 114031488A
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- LBTVHXHERHESKG-UHFFFAOYSA-N tetrahydrocurcumin Chemical compound C1=C(O)C(OC)=CC(CCC(=O)CC(=O)CCC=2C=C(OC)C(O)=CC=2)=C1 LBTVHXHERHESKG-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 82
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000004148 curcumin Substances 0.000 claims description 26
- 235000012754 curcumin Nutrition 0.000 claims description 26
- 229940109262 curcumin Drugs 0.000 claims description 26
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000007868 Raney catalyst Substances 0.000 claims description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
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- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 description 14
- 238000011049 filling Methods 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
- OELMAFBLFOKZJD-UHFFFAOYSA-N 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol Chemical compound C1=C(O)C(OC)=CC(CCC(O)CC(O)CCC=2C=C(OC)C(O)=CC=2)=C1 OELMAFBLFOKZJD-UHFFFAOYSA-N 0.000 description 2
- RSAHICAPUYTWHW-UHFFFAOYSA-N Hexahydrocurcumin Chemical compound C1=C(O)C(OC)=CC(CCC(O)CC(=O)CCC=2C=C(OC)C(O)=CC=2)=C1 RSAHICAPUYTWHW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NCVBXOUXGKFDAQ-UHFFFAOYSA-L [Ni](O)O.[Fe].[Pt] Chemical compound [Ni](O)O.[Fe].[Pt] NCVBXOUXGKFDAQ-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 210000004153 islets of langerhan Anatomy 0.000 description 2
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
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- 230000009466 transformation Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 244000008991 Curcuma longa Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 210000004369 blood Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
Abstract
The invention discloses a method for synthesizing tetrahydrocurcumin, which relates to the technical field of chemical synthesis. The method has the advantages of simple operation, easily obtained raw materials, high product yield, less byproducts, convenient post-treatment, environmental friendliness and suitability for industrial production.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to synthesis of tetrahydrocurcumin.
Background
Tetrahydrocurcumin is a main product of curcumin metabolism in human bodies, the chemical stability of the tetrahydrocurcumin is obviously higher than that of curcumin, and the tetrahydrocurcumin has good aqueous solution stability and is easier to absorb through gastrointestinal tracts than curcumin. It not only can promote the islet cells to secrete insulin and enhance the function of the islets of langerhans, but also has the functions of reducing blood fat and regulating glycolipid metabolic disturbance, thereby having greater development potential.
At present, the synthesis method of tetrahydrocurcumin mainly comprises a biological synthesis method and a chemical synthesis method. The biosynthesis method (Maehara et al, chem. pharm. Bull.,2011,59, 1042. 1044) is to obtain tetrahydrocurcumin by the transformation of endophytic fungi in turmeric rhizome, and the method needs special strains, has low transformation efficiency and is not suitable for mass production.
The chemical synthesis method mostly adopts curcumin and ethanol as raw materials to obtain tetrahydrocurcumin (patent CN111925284A and patent CN 104496779A) through catalytic hydrogenation at present, and the repeated experiments show that the reaction has more byproducts, the product yield and purity are not high, and the subsequent purification difficulty is large.
Therefore, there is an urgent need for an efficient and stable process for preparing tetrahydrocurcumin.
Disclosure of Invention
The invention aims to solve the technical problems in the prior art, and provides a method for synthesizing tetrahydrocurcumin, which can be used for efficiently and stably synthesizing tetrahydrocurcumin, is simple to operate, has low cost and is very suitable for industrial production.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a method for synthesizing tetrahydrocurcumin comprises reacting curcumin, catalyst and acetone at room temperature in hydrogen atmosphere, performing solid-liquid separation after reaction is complete, washing with acetone, removing acetone, and recrystallizing to obtain tetrahydrocurcumin;
the chemical reaction formula of the method is shown as the following formula:
the method comprises the following specific steps:
adding curcumin and a catalyst into a round-bottom flask, then placing a magnetic stirring rotor, covering a rubber soft plug, vacuumizing, and introducing hydrogen into the flask. An appropriate amount of acetone was added to the flask, and the reaction was carried out at room temperature with the magnetic stirrer turned on. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, and recrystallizing with solvent to obtain tetrahydrocurcumin.
Preferably, the molar ratio of curcumin, catalyst and acetone is 1: (0.001-0.01): (1-5), more preferably 1: (0.001-0.005): (2-4).
Preferably, the catalyst comprises palladium, palladium on carbon, Raney nickel, nickel chloride, palladium chloride, Pd-BaSO4-quinoline or Pd-CaCO3-PdO/PdAc2At least one of (1).
Preferably, the solvent for recrystallization includes at least one of ethyl acetate, petroleum ether, diethyl ether, ethanol, or methanol.
Preferably, the reaction time is 10-24 h.
In a preferred embodiment, the catalyst is palladium on carbon; the formula proportion of the curcumin, the palladium/carbon and the acetone is 8.2-8.4 g: 0.3-0.5 g: 55-65 mL; the reaction time is 11-13 h; the solvent adopted by recrystallization is ethanol.
The equipment, reagents, processes, parameters and the like related to the invention are conventional equipment, reagents, processes, parameters and the like except for special description, and no embodiment is needed.
All ranges recited herein include all point values within the range.
As used herein, "about" or "about" and the like refer to a range or value within 10% of the stated range or value.
In the invention, the room temperature, namely the normal environment temperature, can be 10-30 ℃.
Compared with the prior art, the invention has the following beneficial effects:
1. the preparation method of the tetrahydrocurcumin adopts the raw materials without low toxicity and low harm for reaction, has simple post-treatment and small influence on the environment, and conforms to the concept of green sustainable development;
2. the method has high yield and few byproducts, and almost does not contain curcumin, hexahydrocurcumin and octahydrocurcumin;
3. the method has the advantages of cheap raw materials, simple operation, stable reaction and easy control, and is suitable for industrial production.
Drawings
FIG. 1 is an infrared spectrum of tetrahydrocurcumin.
FIG. 2 is a diagram of tetrahydrocurcumin1H-NMR chart.
Detailed Description
The technical solution of the present invention will be further described with reference to the following specific embodiments, but the following embodiments are not intended to limit the present invention, and all of the various application methods adopted according to the principles and technical means of the present invention belong to the scope of the present invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers.
Example 1
A100 mL dry round bottom flask was charged with 8.3g curcumin, 0.4g palladium on carbon and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 60mL of acetone was added to the flask, and the reaction was stirred at room temperature for 12 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding ethanol, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 98% and purity of 99.6%.
Example 2
A100 mL dry round bottom flask was charged with 6g curcumin, 0.1g Raney nickel and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 50mL of acetone was added to the flask, and the reaction was stirred at room temperature for 15 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding ethanol/petroleum ether (5: 1, v/v), and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 97% and purity of 98.9%.
Example 3
A100 mL dry round bottom flask was charged with 5g curcumin, 0.3g palladium on carbon and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 30mL of acetone was added to the flask, and the reaction was stirred at room temperature for 10 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding methanol, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 95% and purity of 97%.
Example 4
A100 mL dry round bottom flask was charged with 10g curcumin, 0.5g Raney nickel and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 80mL of acetone was added to the flask, and the reaction was stirred at room temperature for 20 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding methanol, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 93% and purity of 98.6%.
Example 5
A100 mL dry round bottom flask was charged with 9g curcumin, 0.4g palladium on carbon and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 50mL of acetone was added to the flask, and the reaction was stirred at room temperature for 12 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding methanol/petroleum ether (5/1, v/v), and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 96% and purity of 96.3%.
Example 6
A100 mL dry round bottom flask was charged with 15g curcumin, 0.2g Raney nickel and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 70mL of acetone was added to the flask, and the reaction was stirred at room temperature for 10 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, rotary evaporating to remove acetone, adding ethyl acetate, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 97.2% and purity of 98.8%.
Example 7
A100 mL dry round bottom flask was charged with 5.3g curcumin, 0.15g palladium on carbon and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 55mL of acetone was added to the flask, and the reaction was stirred at room temperature for 12 hours. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding methanol, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 94.6% and purity of 97.4%.
Example 8
A100 mL dry round bottom flask was charged with 5.3g curcumin, 0.15g Raney nickel and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 55mL of acetone was added to the flask, and the reaction was stirred at room temperature for 12 hours. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, rotary evaporating to remove acetone, adding ethyl acetate, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 93.4% and purity of 95.1%.
Example 9
13g of curcumin and 0.6g of Raney nickel were put in a 100mL dry round-bottom flask and evacuated. And filling the two balloons with hydrogen, and then connecting the balloons into a flask to create a hydrogen atmosphere. 80mL of acetone was added to the flask, and the reaction was stirred at room temperature for 24 h. After the reaction was completed, the completion of the reaction was checked by TCL. Filtering, washing with acetone, removing acetone by rotary evaporation, adding ethyl acetate, and recrystallizing to obtain white powder, i.e. tetrahydrocurcumin, with yield of 94.9% and purity of 98%.
Comparative example 1
The patent CN 104496779A is actually operated. Adding 0.5g of platinum-iron-nickel hydroxide composite nanoparticle catalyst into a reaction bottle filled with 100g of curcumin and 300mL of ethanol, stirring and reacting for 1h at room temperature of 20 ℃, evaporating the solvent under reduced pressure to obtain light yellow sticky matter, heating and dissolving the light yellow sticky matter by using 400mL of ethanol, concentrating the light yellow sticky matter to 150mL, refrigerating and standing for crystallization to obtain light yellow solid, wherein the yield is 73%, and the purity is about 85%.
Comparative example 2
The patent CN 104496779A is actually operated. Adding 0.8g of platinum-iron-nickel hydroxide composite nanoparticle catalyst into a reaction bottle filled with 100g of curcumin and 250mL of ethanol, stirring and reacting for 1.5h at the room temperature of 25 ℃, evaporating the solvent under reduced pressure to obtain light yellow sticky matter, heating and dissolving the light yellow sticky matter by using 400mL of ethanol, concentrating the light yellow sticky matter to 150mL, refrigerating and standing for crystallization to obtain light yellow solid, wherein the yield is 67%, and the purity is about 75%.
Comparative example 3
The patent CN111925284A is actually operated. Adding 2g of palladium-carbon into a reaction bottle filled with 10g of curcumin, 30g of dihydropyridine and 200ml of ethanol, carrying out reflux reaction for 8 hours, filtering, and then carrying out reduced pressure evaporation to remove ethanol to obtain a mixture; washing the obtained mixture with 500ml of 1M dilute hydrochloric acid, filtering, dissolving with ethanol, decolorizing with 1g of activated carbon, removing activated carbon, and distilling under reduced pressure to remove ethanol to obtain tetrahydrocurcumin with yield of 66%. Purity was 82% by HPLC.
Comparative example 4
The patent CN111925284A is actually operated. Adding 1g of palladium-carbon into a reaction bottle filled with 10g of curcumin, 30g of dihydropyridine and 250ml of ethanol, carrying out reflux reaction for 12 hours, filtering, and then carrying out reduced pressure evaporation to remove ethanol to obtain a mixture; washing the obtained mixture with 500ml of 1M dilute hydrochloric acid, filtering, dissolving with ethanol, decolorizing with 1g of activated carbon, removing activated carbon, and distilling under reduced pressure to remove ethanol to obtain tetrahydrocurcumin with yield of 62%. Purity was 83% by HPLC.
The above description is only a preferred embodiment of the present invention, and therefore should not be taken as limiting the scope of the invention, which is defined by the appended claims and their equivalents.
Claims (8)
1. A method for synthesizing tetrahydrocurcumin is characterized by comprising the following steps: reacting curcumin, a catalyst and acetone at room temperature in a hydrogen atmosphere, after the reaction is completed, carrying out solid-liquid separation, washing with acetone, removing the acetone, and recrystallizing to obtain tetrahydrocurcumin;
the chemical reaction formula is shown as the following formula:
2. the method of synthesis according to claim 1, characterized in that: the molar ratio of the curcumin to the catalyst to the acetone is 1: 0.001-0.01: 1 to 5.
3. The method of synthesis according to claim 2, characterized in that: the molar ratio of the curcumin to the catalyst to the acetone is 1: 0.001 to 0.005: 2 to 4.
4. The method of synthesis according to claim 1, characterized in that: the catalyst comprises palladium, palladium/carbon, Raney nickel, nickel chloride, palladium chloride, Pd-BaSO4-quinoline or Pd-CaCO3-PdO/PdAc2At least one of (1).
5. The method of synthesis according to claim 1, characterized in that: the solvent for recrystallization comprises at least one of ethyl acetate, petroleum ether, diethyl ether, ethanol or methanol.
6. The method of synthesis according to claim 1, characterized in that: the reaction was checked for completion with TCL.
7. The method of synthesis according to claim 1, characterized in that: the reaction time is 10-24 h.
8. The method of synthesis according to claim 1, characterized in that: the catalyst is palladium/carbon; the formula proportion of the curcumin, the palladium/carbon and the acetone is 8.2-8.4 g: 0.3-0.5 g: 55-65 mL; the reaction time is 11-13 h; the solvent adopted by recrystallization is ethanol.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010956A (en) * | 2022-06-09 | 2022-09-06 | 浙江科技学院 | Poly-tannic acid nanotube material capable of selectively enriching Pd, application of poly-tannic acid nanotube material in purifying and recovering Pd in waste colloidal palladium and preparation method of poly-tannic acid nanotube material |
| CN117586111A (en) * | 2024-01-15 | 2024-02-23 | 天津泰普药品科技发展有限公司 | Method for preparing tetrahydrocurcumin through continuous catalytic hydrogenation |
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| US5266344A (en) * | 1988-08-12 | 1993-11-30 | Kabushiki Kaisha Kobe Seiko Sho | Method for making tetrahydrocurcumin and a substance containing the antioxidative substance tetrahydrocurcumin |
| CN101255119A (en) * | 2008-01-07 | 2008-09-03 | 沈阳药科大学 | Novel tetrahydro curcumin derivatives and salt |
| CN103450115A (en) * | 2013-04-19 | 2013-12-18 | 南京中医药大学 | Curcumin derivative and application of curcumin derivative as cannabinoid receptor modulator |
| CN111018705A (en) * | 2019-12-21 | 2020-04-17 | 南京纽邦生物科技有限公司 | Preparation method of tetrahydrocurcumin and intermediate thereof |
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2021
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| CN115010956A (en) * | 2022-06-09 | 2022-09-06 | 浙江科技学院 | Poly-tannic acid nanotube material capable of selectively enriching Pd, application of poly-tannic acid nanotube material in purifying and recovering Pd in waste colloidal palladium and preparation method of poly-tannic acid nanotube material |
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| CN117586111B (en) * | 2024-01-15 | 2024-03-19 | 天津泰普药品科技发展有限公司 | Method for preparing tetrahydrocurcumin through continuous catalytic hydrogenation |
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