CN102603778A - N-carbamyl-L-glutamic zinc complex and preparation method of N-carbamyl-L-glutamic zinc complex - Google Patents
N-carbamyl-L-glutamic zinc complex and preparation method of N-carbamyl-L-glutamic zinc complex Download PDFInfo
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- CN102603778A CN102603778A CN2012100779882A CN201210077988A CN102603778A CN 102603778 A CN102603778 A CN 102603778A CN 2012100779882 A CN2012100779882 A CN 2012100779882A CN 201210077988 A CN201210077988 A CN 201210077988A CN 102603778 A CN102603778 A CN 102603778A
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Abstract
The invention discloses a new compound which is an N-carbamyl-L-glutamic zinc complex. The molecular formula of the N-carbamyl-L-glutamic zinc complex is ZnC6H8N2O5, and the N-carbamyl-L-glutamic zinc complex can be used as an animal feeding-stuffs additive, so that the production performance of animals can be improved. Particularly, the N-carbamyl-L-glutamic zinc complex is used as a feeding-stuffs additive of a laying hen, the production performance of the laying hen and the quality of eggs can be obviously improved. The invention also discloses a preparation method of the N-carbamyl-L-glutamic zinc complex. The method is simple in process, higher in purity of the product and stable in quality and is suitable for industrialization application.
Description
Technical field
The present invention relates to a kind of organic complex, be specifically related to a kind of N-carbamyl-L-zinc glutamate complex compound and preparation method thereof.
Background technology
(N-Carbamyl-L-glutamic acid is the analog of N-acetyl-L-L-glutamic acid (NAG) NCG) to N-carbamyl-L-L-glutamic acid, and its molecular formula is C
6H
10O
5N
2, structure is following:
N-carbamyl-L-L-glutamic acid can replace NAG to become the allosteric catalyzer of carbamylphosphate synthetase-I (GPS-I); Thereby promote proline(Pro) and Stimulina to transform to N.delta.-carbamylornithine and l-arginine; Increase arginic endogenous synthesizing, keep the balance and stability of l-arginine environment in the body.This shows that NCG stress situation have good effect for what answer between reply animal weaning period that the l-arginine deficiency causes, is a kind of potential fodder additives.
Zinc is one of animal body trace elements necessary, is the moity of multiple metalloenzyme and Regular Insulin.Biochemical functions is called as " bioelement " because of having widely in vivo for it, but can play very important effect to the generation of the sexual development of body, sexual function, sexual cell.Experimentation on animals confirms that scarce zinc can influence the normal growth of animal and cause brain development bad, is embodied in poor growth, and food consumption reduces, apocleisis, and different food is sick, become thin, maldigestion, the sense of taste, baryo,dmia or unusual, degradation under the immunity of organisms.During tradition was raised, the zinc in the animal daily ration was that the form with inorganic salt provides, and the application of adding organic zinc and chelating zinc in recent years is increasingly extensive.Relative inorganic zinc, the organic zinc complex compound receives the protection of ligand, is not vulnerable to the influence that is unfavorable for the physical chemical factor that metal absorbs in the gi tract, has good chemicalstability and biochemical stability.
At present, the synthetic existing report of N-carboxamide-L-L-glutamic acid is also very few about the information of synthetic its metal complex.
Summary of the invention
The purpose of this invention is to provide a kind of new compound: N-carbamyl-L-zinc glutamate complex compound.
Another object of the present invention provides the preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound.
Another object of the present invention provides the application of N-carbamyl-L-zinc glutamate complex compound as animal feedstuff additive.
The technical scheme that the present invention adopted is:
N-carbamyl-L-zinc glutamate complex compound, its molecular formula is ZnC
6H
8N
2O
5, be white powder, soluble in water, be insoluble to ethanol, methyl alcohol, acetone and other organic solvent.
Preferably, said N-carbamyl-L-zinc glutamate complex compound has 1 ~ 2 crystal water.
The compound method of N-carbamyl-L-zinc glutamate complex compound comprises the steps:
1) N-carbamyl-L-L-glutamic acid is mixed with zinc salt, add suitable quantity of water, heated and boiled to solution is clarified;
2) be cooled to normal temperature, stirring slowly is added drop-wise to step 1) gained solution in the absolute ethyl alcohol down fast, drips and finishes, and continues stirring and lets solid fully separate out and blended;
3) filter, washing, drying promptly gets N-carbamyl-L-zinc glutamate complex compound.
Preferably, said zinc salt is any in zinc oxide, zinc hydroxide, zinc subcarbonate, zinc sulfate, the zinc chloride.
Preferably, the mol ratio of N-carbamyl-L-L-glutamic acid and zinc salt is 1 ~ 5:1.
The mass ratio of N-carbamyl preferably, step 2)-L-L-glutamic acid and absolute ethyl alcohol is 1:5 ~ 10.
Preferably, the said washing of step 3) is to use absolute ethanol washing.
Preferably, the said drying of step 3) is meant that decompression is revolved dried or oven dry under 50 ~ 150 ℃.
The above N-carbamyl-L-zinc glutamate complex compound can be used as animal feedstuff additive, replenishes the zinc element in the daily ration.
The invention has the advantages that:
(1) the invention provides synthetic N-carbamyl-more comprehensive technical intelligence of L-zinc glutamate complex compound, it is simple to have a synthesis technique, and product purity is higher, steady quality, and technology is convenient to advantages such as popularization;
(2) N-carbamyl of the present invention-L-zinc glutamate complex compound can be used as animal feedstuff additive, improves the production performance of animal.When especially being used as the fodder additives of laying hen, can significantly improve the quality of production performance, laying rate and the egg of laying hen.
Description of drawings
Fig. 1 is the infared spectrum of N-carbamyl of the present invention-L-zinc glutamate complex compound;
Fig. 2 is the infared spectrum of N-carboxamide-L-L-glutamic acid.
Embodiment
Below in conjunction with embodiment the present invention is further described, but is not limited thereto.
Embodiment 1
The preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound, its step is following:
(1) 0.1molN-carbamyl-L-L-glutamic acid mixes with 0.1mol zinc oxide, adds 30ml water, and heated and boiled to solution is clarified;
(2) be cooled to normal temperature, under stirring fast step (1) gained solution slowly be added drop-wise in the 95g absolute ethyl alcohol, drip and finish, continue to stir half a hour;
(3) filter, use the 40g absolute ethanol washing, it is dried that 50 ℃ of decompressions are revolved, and pulverizes, and can get N-carbamyl-L-zinc glutamate complex compound powder 25.2g, and detection zinc content is 22..88%, and nitrogen content is 9.54%.
Embodiment 2:
The preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound, its step is following:
(1) 0.1molN-carbamyl-L-L-glutamic acid mixes with 0.1mol zinc oxide, adds 30ml water, and heated and boiled to solution is clarified;
(2) be cooled to normal temperature, under stirring fast step (1) gained solution slowly be added drop-wise in the 100g absolute ethyl alcohol, drip and finish, continue to stir half a hour;
(3) filter, use the 40g absolute ethanol washing, it is dried that 50 ℃ of decompressions are revolved, and pulverizes, and can get N-carbamyl-L-zinc glutamate complex compound powder 25.6g, and detection zinc content is 22.66%, and nitrogen content is 9.45%.
Embodiment 3:
The preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound, its step is following:
(1) 0.1molgN-carbamyl-L-L-glutamic acid adds 20ml water, regulates PH=5.5 ~ 6.0 with about 0.2molg sodium hydroxide, adds the 0.1mol Zinc vitriol, is heated to 80 ℃ of reactions one hour;
(2) be cooled to normal temperature, under stirring fast step (1) gained solution slowly be added drop-wise in the 100g absolute ethyl alcohol, drip and finish, continue to stir half a hour;
(3) filter, use the 40g absolute ethanol washing, it is dried that 50 ℃ of decompressions are revolved, and pulverizes, and can get N-carbamyl-L-zinc glutamate complex compound powder 38.8g, and detection zinc content is 15.05%, and nitrogen content is 6.20%.
Embodiment 4:
The preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound, its step is following:
(1) 0.1molN-carbamyl-L-L-glutamic acid adds 30ml water, regulates PH=5.5 ~ 6.0 with about 0.2molg sodium hydroxide, adds the 13.6g Zinc Chloride Anhydrous, is heated to 80 ℃ of reactions one hour;
(2) be cooled to normal temperature, under stirring fast step (1) gained solution slowly be added drop-wise in the 100g absolute ethyl alcohol, drip and finish, continue to stir half a hour;
(3) filter, use the 40g absolute ethanol washing, it is dried that 50 ℃ of decompressions are revolved, and pulverizes, and can get N-carbamyl-L-zinc glutamate complex compound powder 36.5g, and detection zinc content is 15.85%, and nitrogen content is 6.50%.
Embodiment 5:
The preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound, its step is following:
(1) 0.1molgN-carbamyl-L-L-glutamic acid mixes with the 0.1mol zinc hydroxide, adds 30ml water, and heated and boiled to solution is near clarification;
(2) be cooled to normal temperature, under stirring fast step (1) gained solution slowly be added drop-wise in the 100g absolute ethyl alcohol, drip and finish, continue to stir half a hour;
(3) filter, use the 40g absolute ethanol washing, it is dried that 50 ℃ of decompressions are revolved, and pulverizes, and can get N-carbamyl-L-zinc glutamate complex compound powder 25.0g, and detection zinc content is 24.55%, and nitrogen content is 8.90%.
Embodiment 6:
The preparation method of a kind of N-carbamyl-L-zinc glutamate complex compound, its step is following:
(1) 0.1molN-carbamyl-L-L-glutamic acid mixes with the 0.02mol zinc subcarbonate, adds 30ml water, and heated and boiled to solution is near clarification;
(2) be cooled to normal temperature, under stirring fast step (1) gained solution slowly be added drop-wise in the 190g absolute ethyl alcohol, drip and finish, continue to stir half a hour;
(3) filter, use the 40g absolute ethanol washing, it is dried that 50 ℃ of decompressions are revolved, and pulverizes, and can get N-carbamyl-L-zinc glutamate complex compound powder 25.0g, and detection zinc content is 24.85%, and nitrogen content is 8.80%.
The product of embodiment 1 is a white powder, and molecular formula is ZnC
6H
8N
2O
52H
2O, soluble in water, be insoluble to ethanol, methyl alcohol, acetone and other organic solvent.Sample presentation is surveyed infrared spectrogram, and the collection of illustrative plates that obtains is as shown in Figure 1.The infrared figure of corresponding N-carboxamide-L-L-glutamic acid is as shown in Figure 2.This zinc complex sample presentation is carried out ultimate analysis, and Zn, C, H, N content are respectively 22.82%, 24.75%, 2.72%, 9.52% (calculated value: Zn22.58%, C24.87%, H2.76%, N9.67%).Embodiment 2 ~ 6 products obtained therefroms are similarly white powder, and are soluble in water, are insoluble to ethanol, methyl alcohol, acetone and other organic solvent; After same treatment, sample presentation detects, and the gained infrared spectrogram is extremely similar with Fig. 1; Be characterized by same compound, Zn, C, H, N content are near calculated value.ZnC
6H
8N
2O
52H
2O continues 150 ℃ of oven dry, loses crystal water, obtains ZnC
6H
8N
2O
5
Experimentation on animals 1:
Carry out experimentation on animals with embodiment 1 resulting N-carbamyl-L-zinc glutamate complex compound below.
Will be even with a collection of 400 sizes; Athletic 160 age in days Luo Man hens are raised a week in advance; Therefrom select out product age in days 360 healthy hens identical, that body weight is close and be divided into 6 groups at random, 4 experimental group (being respectively that basal diet adds 20ppm, 40ppm, 60ppm, 80ppm N-carbamyl-L-zinc glutamate two aquo complexs), a negative control group (basal diet); A positive control group (basal diet adds the 80ppm Zinc Sulphate Monohydrate), every group of 60 chickens.
This experiment is carried out in the semi open model hen house, and trial period was 6 weeks.Duration of test is fed powder, free choice feeding drinking-water; Keep illumination in 16 hours every day, temperature is at 20-28 ℃, and humidity is at 60-70%.The crude protein content of basal diet is 16.5%, and metabolizable energy is 2750 Kcal/kg, and calcium contents is 3.5%, and phosphorus content is 0.62%.
Performance test: every day time recording each repeat egg number and egg size; Measure each weekly and repeat feed consumption rate and laying hen individual weight; Add up egg size, laying rate, feed consumption rate and feedstuff-egg ratio weekly.
Egg product matter is measured: each repeats to randomly draw 5 pieces of eggs and measures egg shape index and shell thickness weekly.
Slaughter determining: randomly draw 9 hens and butcher, carotid artery is got the hematometry zinc concentration, the quantity of residual zinc in zinc concentration and the ight soil in the shin bone ash content.
Experimental result shows; All experimental group death rates that add N-carbamyl-L-zinc glutamate complex compound all are lower than positive and negative control group; Wherein negative control group death rate the highest (P < 0.05); Having reached 3%., to have added on the treatment group numeral of 40ppm egg number maximum, but with positive control group difference not significantly (P>0.05).The Zinc Sulphate Monohydrate that adds 80ppm is compared in this explanation, and N-carbamyl-L-zinc glutamate two aquo complexs that add 40ppm not only can reach same effect, and have improved the bioavailability of zinc, can practice thrift Mineral resources greatly, alleviate environmental stress.In experimental group, the laying hen individual weight of negative control group the lightest (P < 0.05), egg productivity is few, and egg shape index is poorer than other experimental group, and broken egg number is maximum.Positive control group and each treatment group difference not remarkable (P>0.05) on the feedstuff-meat ratio, but all with negative control group significant difference (P < 0.05).Zinc concentration can be found out from blood plasma, and the treatment group of 80ppm is the highest, and taking second place is the treatment group and positive control group of 60ppm; Zinc concentration is minimum in the negative control group blood.The quantity of residual zinc is opposite in the similar and ight soil of this deposition situation of zinc from the shin bone ash content.
Experimentation on animals 2
Carry out experimentation on animals with embodiment 2 resulting N-carbamyl-L-zinc glutamate complex compounds below.
1, experiment is provided with
60 close batch, body weight 35 age in days weanling pigs close, that be in a good state of health are raised a week in advance, be divided into 5 groups at random, 3 experimental group (are added 100ppm, 150ppm, 200ppm ZnC respectively in the basal diet
6H
8N
2O
5), a negative control group (basal diet), a positive control group (basal diet adds the 200ppm Zinc Sulphate Monohydrate), every group of 3 repetitions, each repeats 4 pigs.
This experiment is carried out in the insulation pig house, and trial period was 8 weeks.Duration of test, free choice feeding drinking-water; Natural lighting, temperature is at 22-28 ℃, and humidity is at 60-70%.The crude protein content of basal diet is 18.0%, and metabolizable energy is 3400 Kcal/kg, and calcium contents is 0.8%, and available phosphorus content is 0.35%.
2, production performance test
Food consumption, the ight soil index of the every hurdle of time recording every day piglet; Measure the individual weight of each piglet weekly; Add up feedstuff-meat ratio weekly, calculate all food consumptions, day weight gain.
3, experimental result
Experimental result shows, it is higher that all add the experimental group ight soil index of N-carbamyl-L-zinc glutamate complex compounds, and diarrhea piglet number is all far below negative control group, and do not have significant difference between the positive control group.But the day weight gain rate of experimental group piglet all is significantly higher than positive and negative control group (P ﹤ 0.05), and the weight gain of piglets that adds 100ppm in the experimental group is the fastest, is illustrated in the ZnC that adds 100ppm in the feed
6H
8N
2O
5Can significantly improve production performance and the immune performance of piglet.
More than experiment shows that N-carbamyl of the present invention-L-zinc glutamate complex compound can be used as animal feedstuff additive, improves production performance and the immune performance of animal.
Above embodiment is merely and introduces preferred case of the present invention, and to those skilled in the art, any conspicuous variation and the improvement in the scope that does not deviate from spirit of the present invention, carried out all should be regarded as a part of the present invention.
Claims (9)
1.N-carbamyl-L-zinc glutamate complex compound, its molecular formula is ZnC
6H
8N
2O
5
2. N-carbamyl according to claim 1-L-zinc glutamate complex compound is characterized in that said complex compound has 1 ~ 2 crystal water.
3.N-the compound method of carbamyl-L-zinc glutamate complex compound comprises the steps:
1) N-carbamyl-L-L-glutamic acid is mixed with zinc salt, add suitable quantity of water, heated and boiled to solution is clarified;
2) be cooled to normal temperature, stirring slowly is added drop-wise to step 1) gained solution in the absolute ethyl alcohol down fast, drips and finishes, and continues stirring and lets solid fully separate out and blended;
3) filter, washing, drying promptly gets N-carbamyl-L-zinc glutamate complex compound.
4. preparation method according to claim 3 is characterized in that, said zinc salt is any in zinc oxide, zinc hydroxide, zinc subcarbonate, zinc sulfate, the zinc chloride.
5. compound method according to claim 3 is characterized in that, the mol ratio of N-carbamyl-L-L-glutamic acid and zinc salt is 1 ~ 5:1.
6. compound method according to claim 3 is characterized in that step 2) in the mass ratio of N-carbamyl-L-L-glutamic acid and absolute ethyl alcohol be 1:5 ~ 10.
7. compound method according to claim 3 is characterized in that, the said washing of step 3) is to use absolute ethanol washing.
8. compound method according to claim 3 is characterized in that, the said drying of step 3) is meant that decompression is revolved dried or oven dry under 50 ~ 150 ℃.
9.N-carbamyl-L-zinc glutamate complex compound is as the application of animal feedstuff additive.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109619322A (en) * | 2019-02-15 | 2019-04-16 | 浙江大学 | A kind of feed improving laying hen eggshell quality |
| CN111072755A (en) * | 2020-01-06 | 2020-04-28 | 湖北泓肽生物科技有限公司 | Lipeptide complex, pharmaceutical composition thereof, preparation method and application thereof |
| CN111100039A (en) * | 2019-12-24 | 2020-05-05 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of argininyl zinc |
| CN111955614A (en) * | 2020-08-31 | 2020-11-20 | 眉山市丹福饲料有限公司 | Pig feed preparation process and pig feed prepared by same |
| CN108165522B (en) * | 2017-12-28 | 2020-12-01 | 中国农业科学院饲料研究所 | Embryonic-period supplement for improving quality of broiler chickens and promoting early growth and application thereof |
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| CN101785534A (en) * | 2010-03-12 | 2010-07-28 | 广州英赛特生物技术有限公司 | Application of zinc glutamate and derivatives thereof as animal feed additive for promoting growth |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101785534A (en) * | 2010-03-12 | 2010-07-28 | 广州英赛特生物技术有限公司 | Application of zinc glutamate and derivatives thereof as animal feed additive for promoting growth |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108165522B (en) * | 2017-12-28 | 2020-12-01 | 中国农业科学院饲料研究所 | Embryonic-period supplement for improving quality of broiler chickens and promoting early growth and application thereof |
| CN109619322A (en) * | 2019-02-15 | 2019-04-16 | 浙江大学 | A kind of feed improving laying hen eggshell quality |
| CN111100039A (en) * | 2019-12-24 | 2020-05-05 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of argininyl zinc |
| CN111072755A (en) * | 2020-01-06 | 2020-04-28 | 湖北泓肽生物科技有限公司 | Lipeptide complex, pharmaceutical composition thereof, preparation method and application thereof |
| CN111072755B (en) * | 2020-01-06 | 2023-09-05 | 湖北泓肽生物科技有限公司 | Lipeptide complex, pharmaceutical composition thereof, preparation method and application thereof |
| CN111955614A (en) * | 2020-08-31 | 2020-11-20 | 眉山市丹福饲料有限公司 | Pig feed preparation process and pig feed prepared by same |
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