CN112194643A - Creatine sulfacetamide and preparation method and application thereof - Google Patents
Creatine sulfacetamide and preparation method and application thereof Download PDFInfo
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- CN112194643A CN112194643A CN202011220449.0A CN202011220449A CN112194643A CN 112194643 A CN112194643 A CN 112194643A CN 202011220449 A CN202011220449 A CN 202011220449A CN 112194643 A CN112194643 A CN 112194643A
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- creatine
- sulfacetamide
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- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 229960003624 creatine Drugs 0.000 title claims abstract description 46
- 239000006046 creatine Substances 0.000 title claims abstract description 46
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 229960002673 sulfacetamide Drugs 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 9
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 claims abstract description 21
- 239000000619 acesulfame-K Substances 0.000 claims abstract description 21
- 229960004998 acesulfame potassium Drugs 0.000 claims abstract description 20
- 235000010358 acesulfame potassium Nutrition 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 13
- 239000003765 sweetening agent Substances 0.000 claims abstract description 13
- XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical compound CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 9
- 229960005164 acesulfame Drugs 0.000 claims abstract description 7
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000006467 substitution reaction Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 14
- 235000019640 taste Nutrition 0.000 abstract description 9
- -1 creatine sulfonamide Chemical class 0.000 abstract description 2
- 229940124530 sulfonamide Drugs 0.000 abstract description 2
- 239000008123 high-intensity sweetener Substances 0.000 abstract 3
- 235000013615 non-nutritive sweetener Nutrition 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 229930006000 Sucrose Natural products 0.000 description 11
- 229960004793 sucrose Drugs 0.000 description 11
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000005720 sucrose Substances 0.000 description 7
- 108010011485 Aspartame Proteins 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 239000000605 aspartame Substances 0.000 description 5
- 235000010357 aspartame Nutrition 0.000 description 5
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 5
- 229960003438 aspartame Drugs 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229940069978 calcium supplement Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 208000025371 Taste disease Diseases 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000012206 bottled water Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 238000012854 evaluation process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019656 metallic taste Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
The invention relates to the technical field of organic chemistry, in particular to creatine sulfacetamide and a preparation method and application thereof. The molecular formula of the creatine sulfonamide is C8H14N4O6S, the preparation method comprises the following steps: adding acesulfame potassium into an ether solution of HCl for substitution reaction, and after the reaction is finished, crystallizing and filtering a reaction product to obtain acesulfame; dissolving the acetyl sulfanilic acid into ethanol, adding creatine for reaction, and performing rotary evaporation on a reaction product after the reaction is finished to obtain the creatine sulfacetamide. The creatine sulfacetamide and the preparation method thereof have the advantages of simple process, convenient operation, high yield and high purity of the prepared product; the invention also provides the sameWhen the high-intensity sweetener is used as a sweetener, the high-intensity sweetener has good taste, the afterbitterness of the high-intensity sweetener is effectively improved, and the crowd acceptance is higher.
Description
Technical Field
The invention relates to the technical field of organic chemistry, in particular to creatine sulfacetamide and a preparation method and application thereof.
Technical Field
Acesulfame potassium (acesulfame potassium) is an artificial sweetener with molecular formula C4H4NO4SK, structural formula as follows:
due to the presence of K in acesulfame K+Therefore, the mouthfeel of the acesulfame potassium has aftertaste, and the good application performance of the acesulfame potassium is influenced by the bad metallic taste while the acesulfame potassium is widely used.
At present, more and more researches are carried out on the acesulfame potassium serving as a raw material to synthesize downstream products of the acesulfame potassium, and the downstream products are used as replacement products of the acesulfame potassium or applied to the new chemical field.
For example, patent CN201110156412.0 discloses a method for producing calcium sulfacetamide, which comprises the following steps: dropwise adding a food-grade calcium hydroxide water phase into a dichloromethane solution of acetylsulfanilic acid in a continuous neutralization mode until the pH value is 4-11, and taking the water phase after layering reaction liquid; concentrating the water phase to crystallize, cooling, and filtering to obtain primary crystals; adding activated carbon and deionized water into the primary crystal, heating, dissolving, decoloring, filtering, cooling, crystallizing, centrifuging to obtain calcium sulfacetamide crystal, and heating and drying to obtain the target product calcium sulfacetamide. The finished product of the sulfacetamide calcium can be used as a calcium supplement and can be added into foods, nutritional health products and medicines for calcium supplement, has sweet taste, good water solubility and quick absorption, and can effectively improve the absorption amount of calcium for human bodies.
Patent CN201811600507.5 discloses a method for preparing aspartame, which comprises the following steps: mixing the aspartame aqueous solution and the acesulfame potassium, adjusting the pH value to 1.2-4.0, and mixing and reacting at the temperature of 20-65 ℃ to form the aspartame. The aspartame aqueous solution is adopted, the pH value and the reaction temperature are controlled, so that the residual potassium chloride can be effectively avoided, and the product yield is ensured to be over 90 percent. The produced aspartame is used as a novel sweetener.
Disclosure of Invention
The invention aims to provide creatine sulfacetamide and a preparation method thereof, the process is simple, the operation is convenient, and the prepared product has high yield and high purity; the invention also provides the application of the high-bitterness-reducing sweetener, and when the high-bitterness-reducing sweetener is used as a sweetener, the high-bitterness-reducing sweetener has good taste, and the high-bitterness-reducing sweetener is more acceptable to people.
The creatine sulfacetamide has the molecular formula of C8H14N4O6S, the structural formula is as follows:
the preparation method of the creatine sulfacetamide comprises the following steps:
(1) adding acesulfame potassium into an ether solution of HCl for substitution reaction, and after the reaction is finished, crystallizing and filtering a reaction product to obtain acesulfame;
(2) dissolving the acetyl sulfanilic acid into ethanol, adding creatine for reaction, and performing rotary evaporation on a reaction product after the reaction is finished to obtain the creatine sulfacetamide.
The synthesis process of the creatine sulfonamide is as follows:
in the step (1), the molar ratio of the acesulfame potassium to the HCl is 1:1-1.25, preferably 1: 1.25; the concentration of HCl in ether is 1-10 mol/L.
In the step (1), the substitution reaction temperature is 10-30 ℃ and the time is 3-4 h.
In the step (1), the crystallization temperature is 5-20 ℃.
In the step (2), the molar ratio of the acetyl sulfanilic acid to the creatine is 1:0.9-1.1, preferably 1:1.
In the step (2), the volume ratio of the mass of the acetylsulfanilic acid to the volume of the ethanol is 1g (1-2) mL, preferably 1g:1.6 mL.
In the step (2), the reaction temperature is 40-55 ℃ and the reaction time is 3-4 h.
In the step (2), the rotary evaporation temperature is 30-35 ℃, and the pressure is-0.085 MPa.
And (3) carrying out the reactions in the step (1) and the step (2) under the protection of nitrogen.
The creatine sulfacetamide is mainly used as a sweetening agent, has high sweetness, can effectively improve the afterbitterness of the high-degree sweetening agent, has good taste and higher crowd acceptance.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention adopts creatine to react with acesulfame potassium to replace K of acesulfame potassium+The creatine sulfacetamide is obtained, the preparation process is simple, the operation is convenient, and the prepared creatine sulfacetamide product has high yield and high purity;
(2) the creatine sulfacetamide prepared by the invention is used as a novel sweetener, has high sweetness, can effectively improve the afterbitterness of the high-degree sweetener, has good taste and higher crowd acceptance.
Drawings
FIG. 1 shows the NMR spectrum of creatine sulfacetamide prepared in example 1 of the present invention.
Detailed Description
The present invention will be further illustrated with reference to the following examples, but the scope of the invention as claimed is not limited to the following examples.
Example 1
(1) 1005g (5 mol) of acesulfame potassium is weighed, dissolved by 6.25L of ether solution of HCl with the concentration of 1mol/L under the protection of nitrogen, reacted for 3 hours at the temperature of 20 ℃, the reaction product is crystallized at the temperature of 10 ℃, and then filtered to obtain 812g (4.98 mol) of acesulfame;
(2) under the protection of nitrogen, 812g of acetyl sulfanilic acid is dissolved in 1.3L of ethanol, 652g of creatine is added to react for 4 hours at the temperature of 40 ℃, and then rotary evaporation is carried out at the temperature of 30 ℃ and under the pressure of-0.085 MPa to obtain 1455g of product, which is detected to be creatine acetyl sulfanilamide, the purity is 99.2 percent, and the yield is 99.0 percent.
Example 2
(1) 1005g (5 mol) of acesulfame potassium is weighed, 1.1L of ether solution of HCl with the concentration of 5mol/L is used for dissolving under the protection of nitrogen, the reaction is carried out for 3 hours at the temperature of 30 ℃, the reaction product is crystallized at the temperature of 20 ℃, and then the filtration is carried out, thus obtaining 807g (4.95 mol) of acesulfame;
(2) under the protection of nitrogen, 807g of sulfacetamide is dissolved into 1L of ethanol, 649g of creatine is added to react for 3 hours at the temperature of 55 ℃, and then rotary evaporation is carried out at the temperature of 35 ℃ and the pressure of-0.085 MPa to obtain 1446g of the product, which is detected to be creatine sulfacetamide, the purity is 99.6 percent, and the yield is 98.4 percent.
Example 3
(1) Weighing 1005g (5 mol) of acesulfame potassium, dissolving with 0.5L of 10mol/L HCl ether solution under the protection of nitrogen, reacting for 4h at 10 ℃, crystallizing the reaction product at 5 ℃, and then filtering to obtain 802g (4.92 mol) of acesulfame;
(2) under the protection of nitrogen, 802g of acetyl sulfanilic acid is dissolved in 1.6L of ethanol, 645g of creatine is added, the reaction is carried out for 4 hours at the temperature of 50 ℃, and then rotary evaporation is carried out at the temperature of 30 ℃ and under the pressure of-0.085 MPa, so that 1449g of product is obtained, which is detected to be creatine acetyl sulfanilamide, the purity is 99.3%, and the yield is 98.6%.
Example 4
(1) 1005g (5 mol) of acesulfame potassium is weighed, dissolved by 3L of ether solution of HCl with the concentration of 2mol/L under the protection of nitrogen, reacted for 3 hours at the temperature of 20 ℃, the reaction product is crystallized at the temperature of 10 ℃, and then filtered to obtain 810g (4.97 mol) of acesulfame;
(2) under the protection of nitrogen, 810g of acetyl sulfanilic acid is dissolved into 1.3L of ethanol, 651g of creatine is added, the reaction is carried out for 4 hours at the temperature of 40 ℃, and then rotary evaporation is carried out at the temperature of 30 ℃ and under the pressure of-0.085 MPa, so that 1451g of product is obtained, which is detected to be creatine acetyl sulfanilamide, the purity is 99.5 percent, and the yield is 98.7 percent.
The creatine sulfacetamide prepared by the invention is used as a sweetening agent to carry out taste test, and the test method comprises the following steps:
the water solution of sucrose with concentration of 5wt% is prepared by OR water, and the water solution of creatine sulfacetamide with concentration gradient of five concentrations of 0.0125wt%, 0.02wt%, 0.025wt%, 0.05wt% and 0.5wt% is prepared by OR water (samples are numbered).
The method comprises the steps of adopting a trained 5-expert panel to evaluate the taste, recording the concentration (namely sweetness evaluation result) of a test sample close to the sweetness of standard cane sugar and the corresponding sweetness (namely sweetness evaluation result), independently and sequentially carrying out each expert in the evaluation process (avoiding mutual interference), cleaning the taste of bottled water after evaluating each sample, and recording the evaluation result, wherein the result is shown in table 1.
Wherein, the sweetness multiple = sucrose concentration/compound concentration with same sweetness.
TABLE 1 comparison of sweetness of creatine sulfacetamide of the present invention with sucrose aqueous solution having a concentration of 5wt%
| Expert order number | 1 | 2 | 3 | 4 | 5 |
| Evaluation results of sweetness | 0.025 wt% | 0.025 wt% | 0.025 wt% | 0.025 wt% | 0.025 wt% |
| Evaluation results of sweetness | Good and similar to sucrose | Good and similar to sucrose | Good and with sugarcaneClose sugar | Good and similar to sucrose | Good and similar to sucrose |
And (4) conclusion: the sweetness of the test sample with the concentration of 0.025wt% is consistent with that of 5wt% of cane sugar and the taste is similar by the determination of the five experts, so the creatine sulfacetamide has the sweetness which is 200 times of that of the cane sugar with the same concentration and the taste is good and similar to that of the cane sugar.
Claims (10)
1. A creatine sulfacetamide characterized by: molecular formula C8H14N4O6S, the structural formula is as follows:
2. a method for preparing the creatine sulfacetamide of claim 1, characterized in that: the method comprises the following steps:
(1) adding acesulfame potassium into an ether solution of HCl for substitution reaction, and after the reaction is finished, crystallizing and filtering a reaction product to obtain acesulfame;
(2) dissolving the acetyl sulfanilic acid into ethanol, adding creatine for reaction, and performing rotary evaporation on a reaction product after the reaction is finished to obtain the creatine sulfacetamide.
3. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (1), the molar ratio of the acesulfame potassium to the HCl is 1: 1-1.25; the concentration of HCl in ether is 1-10 mol/L.
4. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (1), the substitution reaction temperature is 10-30 ℃ and the time is 3-4 h.
5. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (1), the crystallization temperature is 5-20 ℃.
6. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (2), the molar ratio of the acetyl sulfanilic acid to the creatine is 1: 0.9-1.1.
7. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (2), the volume ratio of the mass of the acetyl sulfanilic acid to the volume of the ethanol is 1g (1-2) mL.
8. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (2), the reaction temperature is 40-55 ℃ and the reaction time is 3-4 h.
9. The method for producing creatine sulfacetamide according to claim 2, characterized in that: in the step (2), the rotary evaporation temperature is 30-35 ℃, and the pressure is-0.085 MPa.
10. Use of the creatine sulfacetamide of claim 1, characterized in that: can be used as sweetener.
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| CN202011220449.0A CN112194643A (en) | 2020-11-05 | 2020-11-05 | Creatine sulfacetamide and preparation method and application thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114591203A (en) * | 2022-02-15 | 2022-06-07 | 上海奥萝拉医药科技有限公司 | Preparation method of high-purity creatine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103319376A (en) * | 2013-06-21 | 2013-09-25 | 太仓市新毛涤纶化工有限公司 | Preparation method of creatine hydrochloride |
| WO2018208647A1 (en) * | 2017-05-12 | 2018-11-15 | Augusta University Research Institute, Inc. | Taste-modified creatine salts, compounds, compositions and uses thereof |
| CN109535100A (en) * | 2018-12-26 | 2019-03-29 | 常茂生物化学工程股份有限公司 | The preparation method of L-aspartyl-L-phenylalanine methylester acesulfame |
-
2020
- 2020-11-05 CN CN202011220449.0A patent/CN112194643A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103319376A (en) * | 2013-06-21 | 2013-09-25 | 太仓市新毛涤纶化工有限公司 | Preparation method of creatine hydrochloride |
| WO2018208647A1 (en) * | 2017-05-12 | 2018-11-15 | Augusta University Research Institute, Inc. | Taste-modified creatine salts, compounds, compositions and uses thereof |
| CN109535100A (en) * | 2018-12-26 | 2019-03-29 | 常茂生物化学工程股份有限公司 | The preparation method of L-aspartyl-L-phenylalanine methylester acesulfame |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114591203A (en) * | 2022-02-15 | 2022-06-07 | 上海奥萝拉医药科技有限公司 | Preparation method of high-purity creatine |
| CN114591203B (en) * | 2022-02-15 | 2024-03-29 | 上海奥萝拉医药科技有限公司 | Preparation method of high-purity creatine |
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