CN114424798A - Preparation method and application of feed additive caffeic acid chelated zinc - Google Patents
Preparation method and application of feed additive caffeic acid chelated zinc Download PDFInfo
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- CN114424798A CN114424798A CN202210078654.0A CN202210078654A CN114424798A CN 114424798 A CN114424798 A CN 114424798A CN 202210078654 A CN202210078654 A CN 202210078654A CN 114424798 A CN114424798 A CN 114424798A
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- zinc
- feed additive
- caffeic acid
- caffeate
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/20—Inorganic substances, e.g. oligoelements
- A23K20/30—Oligoelements
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/30—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/418—Preparation of metal complexes containing carboxylic acid moieties
Abstract
The invention discloses a preparation method and application of feed additive caffeic acid chelated zinc, and belongs to the field of chemistry and feed additives. The preparation method of the feed additive caffeic acid chelated zinc mainly comprises the following steps: caffeic acid and divalent metal zinc ions are subjected to chelation reaction under the conditions of a hydrosolvent and a catalyst to prepare the feed additive, namely the caffeic acid chelated zinc. The caffeic acid chelated zinc prepared by the method has the effects of antibiosis, anti-inflammation and antioxidation, and is widely applied to the healthy culture of animals.
Description
Technical Field
The invention relates to the field of chemistry and feed additives, in particular to a preparation method and application of feed additive caffeic acid chelated zinc.
Background
As is well known, while the feed antibiotics widely promote the rapid development of the breeding industry, the bacterial drug resistance is also increasingly severe, which seriously affects the food safety and the public health safety and threatens the health of human beings. In recent years, the national general resistance prohibition at the feed end, resistance reduction and resistance limitation at the breeding end can cause the reduction of the production level of animals, the increase of diseases and the increase of the breeding cost, so that the important importance of ensuring the health of the animals is achieved.
Safeguarding the health of animals requires four concerns: firstly, the integrity of the mucosal immune barrier function is protected, and a first defense line that pathogenic bacteria enter a pig body through the digestive tract, the respiratory tract, the reproductive tract and other ways is avoided; secondly, the composition is antioxidant, can eliminate free radicals, can reduce inflammation and can maintain free radical balance, which is the key of disease resistance; thirdly, activating the functions of immune organs and immune cells of animals, enhancing nonspecific immunity and improving disease resistance; and fourthly, protecting the complete function of the viscera, repairing the injury, protecting the normal function of tissues and organs and promoting the health of animals.
Caffeic acid is a flavonoid compound, has an o-diphenol hydroxyl structure, has wide biological activity, and has various pharmacological actions such as antivirus, antioxidation, anti-inflammation, immunoregulation and the like. The divalent metal zinc ion has the functions of resisting bacteria, improving immunity, maintaining the metabolic function of the liver, maintaining the normal growth and development of various immune factors generated from the liver, maintaining the immunity of animals and the function of an immune system, improving resistance, promoting disease rehabilitation and the like.
According to the invention, caffeic acid and divalent metal zinc ions are subjected to chelation reaction under the conditions of a hydrosolvent and a catalyst by a chemical method to prepare the feed additive, namely the caffeic acid chelated zinc, so that the feed additive is mainly used for the effects of antibiosis, anti-inflammation and antioxidation, and is widely applied to the healthy culture of animals.
Disclosure of Invention
In view of the above, in order to promote the health of animals, the invention prepares a novel feed additive zinc caffeate chelate through a chemical method, wherein the novel feed additive zinc caffeate chelate is prepared by carrying out a chelation reaction on caffeic acid and divalent metal zinc ions, and is mainly used for the effects of antibiosis, anti-inflammation and antioxidation, the health of animals is promoted, and the breeding benefit is improved.
The invention aims to provide a preparation method and application of a feed additive for promoting animal health, starting from caffeic acid with a health regulation function and metal zinc ions with a metabolism regulation function.
In order to achieve the purpose, the invention provides the following technical scheme:
a feed additive for promoting animal health is prepared by chelating caffeic acid with divalent metal zinc ion in the presence of water solvent and catalyst to obtain feed additive caffeic acid chelated zinc.
Preferably, the divalent metal zinc ion is any one or a mixture of more than two of zinc sulfate, zinc chloride and zinc sulfide; the catalyst is any one or a mixture of more than two of piperidine, ethanethiol and sodium ethoxide.
Preferably, the molar ratio of the caffeic acid to the divalent metal zinc ion to the catalyst is 1.0: 1.0-1.5: 0.1 to 0.5.
Optimally, the molar ratio of the caffeic acid to the divalent metal zinc ion to the catalyst is 1.0: 1.1-1.4: 0.2 to 0.4.
Preferably, the temperature of the chelation reaction is 10-60 ℃, and the reaction time is 10-60 min.
Preferably, the temperature of the chelation reaction is 30-50 ℃, and the reaction time is 30-50 min.
The second purpose of the invention is to provide the application of the caffeic acid chelated zinc in animal health, so as to ensure animal health and improve breeding economic benefits.
In order to achieve the purpose, the invention provides the following technical scheme:
the invention also provides application of the feed additive caffeic acid chelated zinc in bacterial diseases of livestock and poultry.
The invention also provides application of the feed additive caffeic acid chelated zinc in livestock and poultry anti-inflammatory and antioxidant.
The invention has the beneficial effects that: compared with caffeic acid and zinc ions, the caffeic acid chelated zinc feed additive has better antibacterial, anti-inflammatory and antioxidant effects, and is mainly used for promoting animal health and improving breeding benefits. The invention also provides a preparation method of the caffeic acid chelated zinc, which has the advantages of simple synthesis process, low cost, no pollution and the like.
Detailed Description
The present invention will be described in further detail with reference to the following specific examples, but the present invention is not limited to the following examples. Variations and advantages that may occur to those skilled in the art may be incorporated into the invention without departing from the spirit and scope of the inventive concept, and the scope of the appended claims is intended to be protected. The procedures, conditions, reagents, experimental methods and the like for carrying out the present invention are general knowledge and common general knowledge in the art except for the contents specifically mentioned below, and the present invention is not particularly limited.
Example 1
Placing 1.8g (10.0mmoL) of caffeic acid and 1.8g (11.0mmoL) of zinc sulfate in a 200mL round-bottom flask, adding 100mL of distilled water, heating to 32 ℃, stirring until the distilled water is completely dissolved, slowly adding 0.17g (0.2mmoL) of piperidine dropwise, reacting at 32 ℃ for 35min after the dropwise addition is finished, cooling to room temperature, adding sulfuric acid aqueous solution dropwise to adjust the pH to 3.5, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
Example 1
Placing 1.82g (10.0mmoL) of caffeic acid and 1.77g (11.0mmoL) of zinc sulfate in a 200mL round-bottom flask, adding 100mL of distilled water, heating to 32 ℃, stirring until the distilled water is completely dissolved, slowly adding 0.017g (0.2mmoL) of piperidine dropwise, reacting for 35min at 32 ℃ after the dropwise adding is finished, cooling to room temperature, adding sulfuric acid aqueous solution dropwise to adjust the pH to 3.5, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
Example 2
Placing 1.82g (10.0mmoL) of caffeic acid and 1.77g (13.0mmoL) of zinc chloride in a 200mL round-bottom flask, adding 100mL of distilled water, heating to 38 ℃, stirring until the materials are completely dissolved, slowly adding an aqueous solution of 0.019g (0.3mmoL) of ethanethiol dropwise, reacting for 48min at 38 ℃ after the dropwise addition is finished, cooling to room temperature, adding an aqueous solution of sulfuric acid dropwise to adjust the pH to 4.8, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
Example 3
Placing 1.82g (10.0mmoL) of caffeic acid and 1.34g (13.8mmoL) of zinc sulfide in a 200mL round-bottom flask, adding 100mL of distilled water, heating to 45 ℃, stirring until the materials are completely dissolved, then slowly adding an aqueous solution of 0.026g (0.38mmoL) of sodium ethoxide dropwise, reacting for 45min at 45 ℃, cooling to room temperature, adding an aqueous solution of sulfuric acid dropwise to adjust the pH to 4.3, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
Example 4
Placing 1.82g (10.0mmoL) of caffeic acid, 0.81g (5.0mmoL) of zinc sulfate and 0.82g (8.5mmoL) of zinc sulfide in a 200mL round-bottomed flask, adding 100mL of distilled water, heating to 48 ℃, stirring until the zinc sulfide is completely dissolved, slowly dropwise adding an aqueous solution of 0.0085g (0.10mmoL) of piperidine and 0.0155g (0.25mmoL) of ethanethiol, reacting for 32min at 48 ℃, cooling to room temperature, dropwise adding an aqueous solution of sulfuric acid to adjust the pH to 3.0, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
Example 5
Placing 1.82g (10.0mmoL) of caffeic acid, 0.82g (6.0mmoL) of zinc chloride and 0.61g (6.3mmoL) of zinc sulfide in a 200mL round-bottomed flask, adding 100mL of distilled water, heating to 40 ℃, stirring until the distilled water is completely dissolved, slowly dropwise adding an aqueous solution of 0.017g (0.20mmoL) of piperidine and 0.0093g (0.15mmoL) of ethanethiol, reacting for 36min at 40 ℃, cooling to room temperature, dropwise adding an aqueous solution of sulfuric acid to adjust the pH to 4.0, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
Example 6
Placing 1.82g (10.0mmoL) of caffeic acid, 0.82g (5.5mmoL) of zinc sulfate and 0.61g (7.0mmoL) of zinc chloride in a 200mL round-bottomed flask, adding 100mL of distilled water, heating to 30 ℃, stirring until the materials are completely dissolved, slowly dropwise adding an aqueous solution of 0.0093g (0.15mmoL) of ethanethiol and 0.0122g (0.18mmoL) of sodium ethoxide, reacting at 30 ℃ for 30min after the dropwise adding is finished, cooling to room temperature, dropwise adding an aqueous solution of sulfuric acid to adjust the pH to 4.2, standing for 30min, filtering, and drying at low temperature to obtain the caffeic acid chelated zinc.
By referring to the method, the feed additive caffeic acid chelated zinc for promoting animal health, which is expressed by the invention, can be prepared. The feed additive zinc caffeate for promoting animal health used in the following examples was prepared according to the above method.
Example 7 application for bacterial diseases in animals.
The test method comprises the following steps: a certain laying hen factory in Henan, in 8 months of 2020, dissects sick chickens, reduces the laying rate, thickens oviducts, breaks eggs and overflows into abdominal cavities, cheese samples, increases ascites and is turbid, the peritoneum has grey white exudates as main characteristics, the salpingitis caused by staphylococcus is diagnosed, 600 sick chickens are selected and divided into 2 groups, 300 chickens in each group are not administrated, the caffeic acid chelated zinc prepared in the embodiment in the test group is not administrated, the test result is counted after 5 days of administration, and the result is shown in Table 1.
TABLE 1 Effect in bacterial diseases in animals
| Group of | Number of sick chickens | The number of cured patients | Number of deaths | Cure rate (%) |
| Blank group | 300 | 0 | 125 | 0 |
| Test group | 300 | 287 | 13 | 95.7 |
The results show that: the zinc caffeate can be used for preventing and treating salpingitis caused by staphylococcus of laying hens, and the cure rate reaches 95.7 percent, so that the zinc caffeate chelate has a good effect on animal bacterial diseases.
Example 8 application in anti-inflammatory and antioxidant treatment of animals.
The test method comprises the following steps: the piglets in a certain pig farm in Henan presented diseases characterized by cough, dyspnea, gradual emaciation and remarkably increased mortality in 2018 and 12 months, 140 sick pigs were selected and divided into 7 groups, 20 pigs in each group were selected, no drug was administered to the blank group, the test groups were respectively administered with the feed additive caffeic acid chelated zinc prepared in examples 1-6, and the test results were counted after 5 days of administration, and the results are shown in Table 2.
And (3) test results: as can be seen from the results in Table 2, compared with the blank group, the test group has obvious curative effect, the pigs have no toxic or side effect and adverse reaction in the test process, and the drug resistance is not easy to generate after the administration.
TABLE 2 feed additive zinc caffeate chelate for preventing and treating animal inflammation and oxidation resistance
| Group of | Number of sick pigs | Number of heads cured | Number of dead heads | Cure rate (%) |
| Blank group | 20 | 0 | 9 | 0 |
| Example 1 | 20 | 18 | 0 | 90.0 |
| Example 2 | 20 | 17 | 0 | 85.5 |
| Example 3 | 20 | 18 | 0 | 90.0 |
| Example 4 | 20 | 16 | 0 | 80.0 |
| Example 5 | 20 | 19 | 0 | 95.0 |
| Example 6 | 20 | 18 | 90.0 |
The results show that: feed additive zinc caffeate chelate for preventing and treating animal inflammation and oxidation resistance
In conclusion, the above embodiments are merely intended to illustrate the technical solution of the present invention and not to limit, although the present invention has been described by referring to certain preferred embodiments thereof, it should be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims.
Claims (9)
1. A feed additive caffeic acid chelated zinc has a structural formula shown in formula I:
2. the method for preparing the feed additive zinc caffeate chelate according to claim 1, wherein the feed additive zinc caffeate chelate is prepared by the following steps: caffeic acid and divalent metal zinc ions are subjected to chelation reaction under the conditions of a hydrosolvent and a catalyst to obtain the feed additive caffeic acid chelated zinc.
3. The method for preparing the feed additive zinc caffeate chelate according to claim 2, wherein the preparation method comprises the following steps: the divalent metal zinc ions are any one or a mixture of more than two of zinc sulfate, zinc chloride and zinc sulfide; the catalyst is any one or a mixture of more than two of piperidine, ethanethiol and sodium ethoxide.
4. The method for preparing the feed additive zinc caffeate chelate according to claim 2, wherein the feed additive zinc caffeate chelate is prepared by the following steps: the molar ratio of the caffeic acid to the divalent metal zinc ion to the catalyst is 1.0: 1.0-1.5: 0.1 to 0.5.
5. The method for preparing the feed additive zinc caffeate chelate according to claim 4, wherein the preparation method comprises the following steps: the molar ratio of the caffeic acid to the divalent metal zinc ion to the catalyst is 1.0: 1.1-1.4: 0.2 to 0.4.
6. The method for preparing the feed additive zinc caffeate chelate according to claim 2, wherein the feed additive zinc caffeate chelate is prepared by the following steps: the temperature of the chelation reaction is 10-60 ℃, and the reaction time is 10-60 min.
7. The method for preparing the feed additive zinc caffeate chelate according to claim 6, wherein the feed additive zinc caffeate chelate is prepared by the following steps: the temperature of the chelation reaction is 30-50 ℃, and the reaction time is 30-50 min.
8. The use of the feed additive zinc caffeate chelate of claim 1 for bacterial disease in animals.
9. The use of the feed additive zinc caffeate chelate of claim 1 for anti-inflammatory and antioxidant use in animals.
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| CN202210078654.0A CN114424798A (en) | 2022-01-24 | 2022-01-24 | Preparation method and application of feed additive caffeic acid chelated zinc |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1436074A (en) * | 2000-04-11 | 2003-08-13 | 宝生物工程株式会社 | Remedies |
| US20140308400A1 (en) * | 2011-11-11 | 2014-10-16 | Nestec S.A. | Polyphenol and metal ions for browning food surfaces |
| US20200171331A1 (en) * | 2017-05-08 | 2020-06-04 | Thomas Cahill | Pharmaceutical compositions comprising caffeic acid chelates |
| CN111714398A (en) * | 2020-05-14 | 2020-09-29 | 广州中医药大学(广州中医药研究院) | Zinc-caffeic acid metal-organic framework compound and preparation method and application thereof |
| CN112876640A (en) * | 2021-01-15 | 2021-06-01 | 江苏华缘高科股份有限公司 | Antibacterial cationic waterborne polyurethane resin and preparation method thereof |
-
2022
- 2022-01-24 CN CN202210078654.0A patent/CN114424798A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1436074A (en) * | 2000-04-11 | 2003-08-13 | 宝生物工程株式会社 | Remedies |
| US20140308400A1 (en) * | 2011-11-11 | 2014-10-16 | Nestec S.A. | Polyphenol and metal ions for browning food surfaces |
| US20200171331A1 (en) * | 2017-05-08 | 2020-06-04 | Thomas Cahill | Pharmaceutical compositions comprising caffeic acid chelates |
| CN111714398A (en) * | 2020-05-14 | 2020-09-29 | 广州中医药大学(广州中医药研究院) | Zinc-caffeic acid metal-organic framework compound and preparation method and application thereof |
| CN112876640A (en) * | 2021-01-15 | 2021-06-01 | 江苏华缘高科股份有限公司 | Antibacterial cationic waterborne polyurethane resin and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| 王素素 等: "Zn~(2+)配位双模板印迹聚合物的制备表征及同时萃取升麻中的阿魏酸和咖啡酸", 化工进展, vol. 35, no. 4, pages 1132 - 1139 * |
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