CN110325052B - Application of aspartic acid fatty acyl derivative in preparation of animal feed additive - Google Patents

Application of aspartic acid fatty acyl derivative in preparation of animal feed additive Download PDF

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CN110325052B
CN110325052B CN201880012282.3A CN201880012282A CN110325052B CN 110325052 B CN110325052 B CN 110325052B CN 201880012282 A CN201880012282 A CN 201880012282A CN 110325052 B CN110325052 B CN 110325052B
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feed
aspartic acid
fatty acyl
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feed additive
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黄华成
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Peng Xianfeng
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Abstract

Discloses an application of an acyl derivative of aspartic acid with a structure shown as a formula (I) or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate or a feed acceptable salt thereof in preparing an animal feed additive, has good improvement effect on the production performance of bred animals,
Figure DDA0002168830280000011
wherein Y and X are independently selected from C 1 ‑C 20 Alkoxy or OH; r 1 Is R 1a C(＝O)、R 1a S(＝O) 2 Or H; r 2 Is R 2a C (= O) or R 2a S(＝O) 2 (ii) a Said R 1a And R 2a Are each independently selected from C 1 ‑C 20 Alkyl or C 3 ‑C 7 A cycloalkyl group.

Description

Application of aspartic acid fatty acyl derivative in preparation of animal feed additive
The technical field is as follows:
the invention belongs to the field of animal feed additives, and particularly relates to an application of an aspartic acid fatty acyl derivative in preparation of an animal feed additive, a feeding composition containing the aspartic acid fatty acyl derivative, and an application of the feeding composition in preparation of the animal feed additive and animal feed.
The background art comprises the following steps:
aspartic acid is an unnecessary amino acid in animals. N-acylated aspartic acid has a fat mouthfeel and serves as a low-calorie fat substitute in health foods. The N-acylated aspartic acid is an amino acid surfactant, has good air bubble capacity and stable storage, and is used in the fields of personal care and public health such as toothpaste, kitchen cleaner, toilet cleaner, shampoo, bath lotion and the like.
Acetylated aspartic acid is a component of many plants or foods, also a central nervous system substance, and is an acetic acid donor for myelin liquid fatty acids, and studies have shown that acetylated aspartic acid exhibits an irritating, unpleasant mixed acid taste in the human taste system.
The feed is a product for animals which is processed and manufactured industrially, and is a main animal food in modern intensive breeding industry. In the process of animal breeding, farmers desire that the feed products eaten by animals can be absorbed and utilized by the animals to the maximum extent, and the production performance of the animals is improved, so that the aim of improving the economic benefit of breeding is fulfilled. The feed additive with corresponding effect is added into the feed product, so that the utilization rate of the feed product can be effectively improved.
The feed additive is a small amount or trace substances added in the processes of processing, preparing and using the feed, and comprises nutritional feed additives and common feed additives. The general feed additive refers to a small amount or trace amount of substances which are added into the feed to ensure or improve the quality of the feed and improve the utilization rate of the feed. The common feed additives commonly used in the field at present and having the functions of efficiently and stably improving the feed utilization rate and improving the animal production performance mainly comprise a high-dose copper agent, a high-dose zinc agent, feed antibiotics, a chemical synthetic antibacterial agent and the like, but the substances have large side effects in the breeding industry after long-term use, such as the defects of liver and kidney toxicity, growth inhibition, kidney function damage, urinary tract disorder, teratogenesis, mutagenesis, drug resistance generation, drug residue, environment pollution and the like of animals. In order to ensure the health of animals and improve the production benefit of the breeding industry, the problem to be solved in the field is to find effective, stable and safe new feed additives.
The invention content is as follows:
based on the above, the invention provides a stable and effective aspartic acid fatty acyl derivative or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate and an application of a feed acceptable salt thereof in preparing animal feed additives; the invention also provides a feeding composition containing the aspartic acid fatty acyl derivative or racemate, stereoisomer, geometric isomer, tautomer, solvate and feed acceptable salt thereof, and application of the composition in preparation of animal feed additives and animal feed.
In one aspect, the invention provides an application of aspartic acid fatty acyl derivative with a structure shown as a formula (I) or racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof in preparing animal feed additives:
Figure BDA0002168830270000021
in some embodiments, Y and X are each independently selected from C 1 -C 20 Alkoxy or OH; r 1 Is R 1a C(＝O)、R 1a S(＝O) 2 Or H; r 2 Is R 2a C (= O) or R 2a S(＝O) 2 (ii) a Said R 1a And R 2a Are each independently selected from C 1 -C 20 Alkyl or C 3 -C 7 A cycloalkyl group.
In some embodiments, R of the fatty acyl derivative of aspartic acid 1 Is H.
In some embodiments, R of the fatty acyl derivative of aspartic acid 2 Is R 2a C(＝O)，R 2a Is selected from C 1 -C 20 Alkyl or C 3 -C 7 A cycloalkyl group.
In some embodiments, R of the fatty acyl derivative of aspartic acid 2a Is selected from C 1 -C 10 An alkyl group.
In some embodiments, Y and X of the fatty acyl derivative of aspartic acid are OH.
In some embodiments, Y and X of the fatty acyl derivatives of aspartic acid are each independently selected from C 1 -C 20 Alkoxy or OH, and not simultaneously OH.
In some embodiments, Y and X of the fatty acyl derivative of aspartic acid are each independently selected from C 1 -C 10 Alkoxy or OH, and not simultaneously OH.
In some embodiments, the feed acceptable salt of the fatty acyl derivative of aspartic acid is a metal ion salt.
In some embodiments, the feed acceptable salt of the aspartic acid fatty acyl derivative is preferably a sodium ion salt, a calcium ion salt, a zinc ion salt, a copper ion salt, or an iron ion salt.
In another aspect, the invention provides a feeding composition, which comprises at least one of the aspartic acid fatty acyl derivatives or racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof, and at least one feeding auxiliary material.
The feedable auxiliary materials are selected from feedable carriers, diluents, adjuvants, vehicles or combinations thereof.
In some embodiments, the feed composition further comprises an animal feed material.
In some embodiments, the feed composition further comprises an additional animal feed additive.
In some embodiments, the feed composition further comprises an animal feed material and an additional animal feed additive.
In some embodiments, the additional animal feed additive can be selected from a nutritional feed additive and/or a general feed additive and/or a pharmaceutical feed additive.
In another aspect, the invention provides the use of the feed composition in the preparation of an animal feed additive.
In another aspect, the invention provides the use of the feed composition in the preparation of an animal feed.
In another aspect, the invention provides a method for improving the production performance of farmed animals.
The invention has the beneficial effects that:
the result of animal breeding experiments shows that the aspartic acid fatty acyl derivative or racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof can be used as an animal feed additive, and has a good effect of improving the production performance of animals.
Any embodiment of any aspect of the invention may be combined with other embodiments as long as there is no conflict between them. Furthermore, in any embodiment of any aspect of the present invention, any technical feature may be applied to that technical feature in other embodiments as long as there is no contradiction therebetween.
The foregoing merely summarizes certain aspects of the invention and is not intended to be limiting. The foregoing and other aspects are more fully described below.
Further details of the invention are described.
Reference will now be made in detail to certain embodiments of the invention, examples of which are illustrated by the accompanying structural and chemical formulas. The invention is intended to cover alternatives, modifications and equivalents, which may be included within the scope of the invention as defined by the appended claims. Furthermore, certain features of the invention, which are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment or in any suitable subcombination.
A compound is provided.
The invention relates to a compound which is an aspartic acid fatty acyl derivative with a structure shown in a formula (I),
Figure BDA0002168830270000031
wherein Y and X are substituents on the carboxyl group of aspartic acid, R 1 And R 2 Is a substituent on a nitrogen atom (abbreviated as N). Y and X are each independently selected from C 1 -C 20 Alkoxy or OH; r 1 Is R 1a C(＝O)、R 1a S(＝O) 2 Or H; r 2 Is R 2a C (= O) or R 2a S(＝O) 2 (ii) a Said R 1a And R 2a Are each independently selected from C 1 -C 20 Alkyl or C 3 -C 7 A cycloalkyl group.
In general, "substituted" means that one or more substitutable hydrogen atoms in a given structure are substituted with a particular substituent, a substituted group may have one substituent at each substitutable position of the group, and when more than one position in a given formula can be substituted with one or more substituents of a particular group, then the substituents may be substituted at each position, either identically or differently.
In the present invention, "C 1 -C 20 Alkyl "represents a saturated alkyl group containing 1 to 20 carbon atoms, such as methyl, ethyl, propyl, isopropyl, … …, a straight or branched alkyl group containing 20 carbon atoms; ' C 3 -C 7 Cycloalkyl "means a cyclic alkyl group containing only two elements, carbon and hydrogen, containing from 3 to 7 carbon atoms, such as cyclopropyl, 2-methylcyclopropyl, cyclopentyl, and the like.
Optionally, R of the aspartic acid fatty acyl derivative 1 Is R 1a S(＝O) 2 Or H, R 2 Is R 2a S(＝O) 2 (ii) a R is as described 1a And R 2a Are each independently selected from C 1 -C 20 Alkyl or C 3 -C 7 Cycloalkyl, Y and X are each independently selected from C 1 -C 20 Alkoxy or OH.
Further, said R 1 Is H, R 2 Is R 2a S(＝O) 2 (ii) a Said R 2a Is selected from C 1 -C 20 Alkyl or C 3 -C 7 Cycloalkyl, Y and X are each independently selected from C 1 -C 20 Alkoxy or OH.
Optionally, R of the aspartic acid fatty acyl derivative 1 Is R 1a C (= O) or H, R 2 Is R 2a C (= O); said R 1a And R 2a Are each independently selected from C 1 -C 20 Alkyl or C 3 -C 7 Cycloalkyl, Y and X are each independently selected from C 1 -C 20 Alkoxy or OH.
Further, said R 1 Is H, R 2 Is R 2a C (= O); said R 2a Is selected from C 1 -C 20 Alkyl or C 3 -C 7 Cycloalkyl, Y and X are each independently selected from C 1 -C 20 Alkoxy or OH.
Optionally, R is 1a Or R 2a Is selected from C 1 -C 20 Alkyl radical。
Further, said R 1a Or R 2a Selected from straight chain C 1 -C 10 Alkyl, in particular methyl (CH) 3 ) Ethyl (CH) 2 CH 3 ) N-propyl ((CH) 2 ) 2 CH 3 ) N-butyl ((CH) 2 ) 3 CH 3 ) N-pentyl ((CH) 2 ) 4 CH 3 ) N-butyl ((CH) 2 ) 5 CH 3 ) N-heptyl ((CH) 2 ) 6 CH 3 ) N-octyl ((CH) 2 ) 7 CH 3 ) N-nonyl group ((CH) 2 ) 8 CH 3 ) N-decyl ((CH) 2 ) 9 CH 3 ) One of them.
Optionally, R is 1a Or R 2a Selected from the group consisting of branched chains C 1 -C 10 Alkyl, including but not limited to isopropyl ((CH) 3 ) 2 CH), isobutyl ((CH) 3 ) 3 C) And the like.
Optionally, Y and X of the aspartic acid fatty acyl derivative are both OH.
Optionally, Y and X of the aspartic acid fatty acyl derivative are selected from C 1 -C 20 Alkoxy or OH, but not simultaneously OH, in particular simultaneously C 1 -C 20 Alkoxy or each is C 1 -C 20 One of alkoxy and OH.
Further, the alkoxy group is preferably a straight chain or branched C 1 -C 10 Alkoxy, including but not limited to methoxy (OCH) 3 ) Ethoxy (OCH) 2 CH 3 ) N-propaneoxy (O (CH) 2 ) 2 CH 3 ) Isopropaneoxy (OCH) 2 (CH 3 ) 2 ) N-butoxy (O (CH) 2 ) 3 CH 3 ) Tert-butyoxy (OC (CH) 3 ) 3 ) N-pentyloxy (O (CH) 2 ) 4 CH 3 ) N-alkoxy (O (CH) 2 ) 5 CH 3 ) N-heptyloxy (O (CH) 2 ) 6 CH 3 ) N-octyloxy (O (CH) 2 ) 7 CH 3 ) N-nonaneOxy (O (CH) 2 ) 8 CH 3 ) Or n-decyloxy (O (CH) 2 ) 9 CH 3 )。
Optionally, the feed acceptable salt of the aspartic acid fatty acyl derivative is a metal ion salt, specifically a monovalent metal ion salt, a divalent metal ion salt or a trivalent metal ion salt.
Specifically, the monovalent metal ions include, but are not limited to, sodium ions, potassium ions, lithium ions, ammonium ions; the divalent metal ions include but are not limited to calcium ions, magnesium ions, zinc ions, copper ions, ferrous ions, manganese ions; the trivalent metal ions include but are not limited to iron ions, nickel ions, chromium ions and aluminum ions.
In some embodiments, the metal ion is a zinc ion.
In other embodiments, the metal ions are copper ions.
In other embodiments, the metal ion is sodium ion.
In other embodiments, the metal ion is calcium ion.
In other embodiments, the metal ion is iron ion.
And (3) preparing and purifying the compound.
The invention relates to a preparation method of aspartic acid fatty acyl derivatives shown in formula (I), which takes aspartic acid (Asp) as a starting raw material, and the related chemical reaction mainly comprises acylation of amino and esterification of carboxyl.
In some embodiments, Y and X in formula (I) are C 1 -C 20 The preparation method of the aspartic acid fatty acyl derivative shown in the formula (I) comprises two steps of esterification of carboxyl and acylation of amino, wherein the two steps are shown in the formula (II).
Figure BDA0002168830270000051
It is to be understood that X and R in the formula (II) 1 Representing only substituent groups, if the starting material X-H, R 1 OR 1 And R 1 The substance represented by-Cl is not a single substance but X or R 1 Is to be understood as a collection of substituents.
In some embodiments, Y and X are both-OH in formula (I), and the fatty acyl derivatives of aspartic acid of formula (I) are prepared according to formula (III).
Figure BDA0002168830270000052
It is to be understood that R in the formula (III) 1 Representing only substituent groups when starting material R 1 OR 1 When the indicated species is not a single species then R1 on the target product (TM) should be understood to be a collection of substituents.
Further, Y and X are both OH or C respectively 1 -C 20 The fatty acyl derivative of aspartic acid in one of alkoxy and OH reacts with metal chloride or metal bromide under alkaline condition to generate metal ion salt of the fatty acyl derivative of aspartic acid, such as zinc salt, copper salt, calcium salt, iron salt or sodium salt and the like.
In some embodiments, the aspartic acid is a chiral compound, the aspartic acid is selected from L- (-) -aspartic acid (structure formula (IV)), D- (+) -aspartic acid (structure formula (V)) or DL- (+ -) -aspartic acid of a racemate, and the aspartic acid fatty acyl derivative with a chiral center is obtained by reacting the aspartic acid with the related alcohol and carboxylic acid derivative.
Figure BDA0002168830270000061
In some embodiments, the chiral stereoisomers of aspartic acid and the stereoisomers of fatty acyl derivatives of aspartic acid can undergo a stereoconfigurational transformation under suitable conditions, such as a stereoconfigurational interconversion of aspartic acid or fatty acyl derivatives of aspartic acid, for example, a stereoconfigurational interconversion of aspartic acid according to formula (vi):
Figure BDA0002168830270000062
when the related reaction substance reacts with aspartic acid and the like to generate the corresponding aspartic acid fatty acyl derivative with a rigid structure, different geometric isomer products can be generated during the reaction of the reaction substrate.
The stereoisomers, geometric isomers and tautomers described above are also included in the practice of the present invention.
"stereoisomers" as referred to herein refers to compounds having the same chemical structure but differing in the arrangement of atoms or groups in space, including enantiomers, diastereomers, conformers, geometric isomers, atropisomers, and the like. "enantiomer" refers to two isomers of a compound that are not overlapping but are in mirror image relationship to each other. "diastereomer" refers to a stereoisomer having two or more chiral neutrals whose molecules are not mirror images of each other, and having different physical properties such as melting point, boiling point, spectral properties, and reactivity. Mixtures of diastereomers may be separated by high resolution analytical procedures such as electrophoresis or chromatography; "tautomers" refer to structural isomers that have different energies that can interconvert through a low energy barrier.
In some embodiments, the present invention provides processes for the preparation of fatty acyl derivatives of aspartic acid further involving isolation, purification, or recrystallization of the reaction product. The reaction product can be used for obtaining crude products from the reaction system by a solvent removal method. In order to obtain a solid substance with higher chemical purity and lower impurity content, the crude product is dissolved, crystallized or precipitated or recrystallized and separated in an alcohol solvent, an alcohol-water mixed solvent or other organic solvents which can be used for product recrystallization under the conditions of proper temperature, illumination, mechanical vibration and the like to obtain the aspartic acid fatty acyl derivative with a certain crystal form state. The aspartic acid fatty acyl derivative with a certain crystal form state is aspartic acid fatty acyl derivative crystal or a solvate of the aspartic acid fatty acyl derivative. The solvate of the aspartic acid fatty acyl derivative can be selected from a hydrate of the aspartic acid fatty acyl derivative or an ethanol compound of the aspartic acid fatty acyl derivative.
The term "solvate" as used herein refers to a eutectic association formed by binding a stoichiometric or non-stoichiometric amount of solvent molecules by non-covalent intermolecular forces due to external and internal conditions during the contact between the compound of the present invention and the solvent molecules. Solvents that form solvates include, but are not limited to, water, acetone, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, isopropanol, and the like. "hydrate" refers to an association or crystal of solvent molecules with water, i.e., a compound that binds a stoichiometric or non-stoichiometric amount of water by non-covalent intermolecular forces.
The preparation of the aspartic acid fatty acyl derivative provided by the invention can be used for obtaining solid substances with higher chemical purity and lower impurity content and can be further processed by a salting-out method. The salting-out method is a process of salt-forming precipitation of the aspartic acid derivative and corresponding organic base, inorganic base, organic acid or inorganic acid by utilizing the principles of an acid-base neutralization method, an acid-base coordination method or an acid-base chelation method, so as to obtain a salt acceptable for the feed.
The feed acceptable salt is a salt formed by the aspartic acid fatty acyl derivative and organic base, inorganic base, organic acid or inorganic acid which are nontoxic to animals. By "feed acceptable" is meant that the substance or composition must be chemically or toxicologically compatible in connection with the constituent feed or the edible farmed animals.
In some embodiments, the fatty acyl derivative of aspartic acid is a diester or mixed ester (i.e., Y and X are the same or different C at the same time) 1 -C 20 Alkyl), the salting-out precipitation process of the post-treatment forms acid-base coordination salts and or acid-base chelating salts with inorganic acids or organic acids including but not limited to acetate, maleate, succinate, mandelic acidA salt, fumarate, malonate, malate, 2-hydroxypropionate, pyruvate, oxalate, glycolate, salicylate, glucuronate, galacturonate, citrate, tartrate, aspartate, glutamate, benzoate, p-methylbenzoate, cinnamate, p-toluenesulfonate, benzenesulfonate, methanesulfonate, ethanesulfonate, trifluoromethanesulfonate, or a combination thereof; the inorganic acid includes, but is not limited to, hydrochloride, hydrobromide, phosphate, sulfate, nitrate, or combinations thereof.
In some embodiments, the fatty acyl derivative of aspartic acid is a monoester (i.e., Y and X are each C) 1 -C 20 One of alkyl and H), the salting-out precipitation process of the post-treatment forms acid-base coordination salt and/or acid-base chelate salt with organic acid or inorganic acid, or forms acid salt with organic base or inorganic base. The organic acid includes, but is not limited to, acetate, maleate, succinate, mandelate, fumarate, malonate, malate, 2-hydroxypropionate, pyruvate, oxalate, glycolate, salicylate, glucuronate, galacturonate, citrate, tartrate, aspartate, glutamate, benzoate, p-methylbenzoate, cinnamate, p-toluenesulfonate, benzenesulfonate, methanesulfonate, ethanesulfonate, trifluoromethanesulfonate or a combination thereof; the inorganic acid includes, but is not limited to, hydrochloride, hydrobromide, phosphate, sulfate, nitrate, or combinations thereof. The organic base includes but is not limited to ammonia or triethylamine. The inorganic base includes, but is not limited to, sodium hydroxide, potassium hydroxide, magnesium hydroxide, or calcium hydroxide.
Stability studies of fatty acyl derivatives of aspartic acid.
The aspartic acid fatty acyl derivative or racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof provided by the invention is used for determining the stability of the compound at the temperature of 60 ℃, the test period is 10 days, and the content of the compound does not change obviously along with the change of time in the test period.
The present invention relates to the use of fatty acyl derivatives of aspartic acid.
The aspartic acid fatty acyl derivative with the structure shown as (I) and the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate or the acceptable salt of the feed are applied to the preparation of animal feed additives.
The term "animal" as used herein means a human or a cultured animal which is incapable of synthesizing organic matter from inorganic matter and capable of having life activities such as feeding, digestion, absorption, respiration, circulation, excretion, sensation, exercise, and reproduction by using only organic matter as a food. "farmed animals" include poultry, livestock, aquaculture animals, and other animals that are artificially reared to be legally caught, including pets, such as cats and dogs. The term "livestock" is, for example, any of pigs, cattle, horses, goats, sheep, deer, and many useful rodents. The term "poultry" is intended to include, for example, chickens, ducks, geese, quail, pigeons and the like. The term "aquaculture animal" includes, for example, fish, shrimp, turtles, and the like.
The fatty acyl derivatives of aspartic acid and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof provided by the present invention are used to prepare non-nutritive additives for improving animal productivity as animals at various growth stages, which can be selected from livestock, poultry, aquaculture animals or pets at various growth stages.
Optionally, the domestic animals include, but are not limited to, pigs, cattle, sheep, horses, rabbits, mink, or donkeys, the poultry includes, but is not limited to, chickens, turkeys, ducks, geese, quail, or pigeons, the aquaculture animals include, but are not limited to, fish, shrimp, turtles, crabs, turtles, bullfrogs, eels, or loaches, and the pets include, but are not limited to, dogs or cats of each subspecies.
In one embodiment, the fatty acyl derivative of aspartic acid provided by the invention and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof are used for preparing a feed additive for weaned pigs, so that the feed intake of the weaned pigs can be increased, the average daily gain of the weaned pigs can be effectively increased, and the feed conversion rate can be improved.
In another embodiment, the fatty acyl derivative of aspartic acid provided by the invention, as well as racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof, is used for preparing a feed additive for laying hens, and can effectively improve the laying rate of the laying hens, increase the egg weight and reduce the feed-egg ratio of the laying hens.
In another embodiment, the feed additive prepared by applying the fatty acyl derivative of aspartic acid provided by the invention and the racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof can obviously improve the production performance of broiler chickens.
In another embodiment, the feed additive prepared by applying the fatty acyl derivative of aspartic acid and the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate or the acceptable salt of feed provided by the invention can obviously improve the production performance of meat ducks and laying ducks.
In another embodiment, the fatty acyl derivatives of aspartic acid provided by the invention and the racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof are used for preparing feed additives for improving the production performance of fish.
In another embodiment, the feed additive prepared by using the fatty acyl derivative of aspartic acid provided by the invention and its racemate, stereoisomer, geometric isomer, tautomer, solvate or acceptable feed salt has a more remarkable effect on improving the production performance of pets.
The feed acceptable salt of the fatty acyl derivative of aspartic acid provided by the invention, which is applied to the preparation of the animal feed additive, is a metal ion salt.
Optionally, the feed acceptable salt of the fatty acyl derivative of aspartic acid is a metal ion salt of the fatty acyl derivative of aspartic acid with a structure shown in formula (I).
Furthermore, Y and X in the aspartic acid fatty acyl derivative with the structure shown as the formula (I) are selected from C 1 -C 20 Alkoxy or OH, but not simultaneously C 1 -C 20 And the metal ion salt is obtained by exchanging OH of the aspartic acid fatty acyl derivative with metal ions, and meets the requirements of feed additive preparation or feed preparation.
Specifically, the metal ion is selected from a monovalent metal ion, a divalent metal ion or a trivalent metal ion.
In some embodiments, the monovalent metal ion is a sodium ion (Na (i)), a potassium ion (K (i)), or a lithium ion (Li (i)).
In some embodiments, the divalent metal ion is a calcium ion Ca (II), a magnesium ion Mg (II), a copper ion Cu (II), a zinc ion Zn (II), a ferrous ion Fe (II), a manganese ion Mn (II), a cobalt ion Co (II), or a nickel ion Ni (II).
In one embodiment, the metal ion salt of the fatty acyl derivative of aspartic acid used in the preparation of the animal feed supplement is a zinc ion salt, and the animal feed supplement is an organozinc agent for animals as a high-dose inorganic zinc replacement.
In one embodiment, the metal ion salt of the fatty acyl derivative of aspartic acid used in the preparation of the animal feed supplement is a copper ion salt, and the animal feed supplement is an animal organic copper as a high-dose replacement for an animal inorganic copper.
In one embodiment, the metal ion salt of the fatty acyl derivative of aspartic acid used in the preparation of the animal feed additive is an iron ion salt, and the animal feed additive is an elemental iron supplement for animals.
In some embodiments, the trivalent metal ion is an aluminum ion Al (III), a chromium ion Cr (III), or an iron ion Fe (III).
The invention relates to a feeding composition.
A feeding composition comprises at least one of fatty acyl derivatives of aspartic acid and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof and a feeding adjuvant, wherein the feeding adjuvant is a feeding carrier, diluent, adjuvant, solvent or combination thereof.
The feed is a product which is industrially processed and manufactured and is eaten by animals.
The composition refers to a compound set comprising one or more compounds as active ingredients.
The term "comprising" as used herein is open-ended, meaning that the meaning of the term is included, but not exclusive of other aspects.
The carrier is a feedable substance which can carry active ingredients, improve the dispersibility of the active ingredients and have good chemical stability and adsorbability, and is an organic carrier or an inorganic carrier. The organic carrier is a material containing much crude fiber, and comprises but is not limited to corn flour, corn cob powder, wheat bran, rice hull powder, defatted rice bran, unite bran, corn straw powder, peanut hull powder and the like. The inorganic carrier is mineral substance, mainly divided into calcium salt and silicon oxide, and is used for preparing microelement premix, including but not limited to calcium carbonate, silicate, vermiculite, zeolite, sepiolite, etc.
The diluent is organic diluent and inorganic diluent, which can separate trace components from each other and reduce the mutual reaction between active components to increase the stability of the active components without affecting the physical and chemical properties of the relevant substances. Organic diluents include, but are not limited to, corn flour, de-germ corn flour, dextrose (glucose), sucrose, gluten-bearing raw wheat flour, parched soybean flour, wheat middlings, corn gluten meal, and the like; inorganic diluents include, but are not limited to, limestone, monocalcium phosphate, shell powder, kaolin (kaolin), salt, and sodium sulfate.
The auxiliary agent is a wetting agent for inducing the inherent viscosity of the substance, a binding agent for binding the substance, a disintegrating agent for breaking the sheet-shaped substance into a plurality of fine particles, a retention aid for reducing the friction force between the particles or an anti-sticking agent for preventing the adhesion of the material, and comprises but is not limited to magnesium stearate, talcum powder, vegetable oil, magnesium lauryl sulfate, starch slurry, water, inorganic salt, dextrin, powdered sugar and the like.
The term "vehicle" as used herein refers to a solvent necessary to dissolve or disperse a solid, and includes, but is not limited to, water, ethanol, glycerol, and the like.
In some embodiments, the feed composition further comprises additional animal feed additives and/or animal feed materials.
The animal feed additive is a nutritional feed additive, a general feed additive or a pharmaceutical feed additive.
The nutritional feed additive is a small amount of or trace substances which are added into a compound feed to balance feed nutrients, improve the utilization rate of the feed and directly play a nutritional role on animals, and is amino acid, amino acid salt and analogues thereof, vitamin and retinoid, mineral elements and complex (chelate) compounds thereof, microbial enzyme preparation or nonprotein nitrogen.
The general feed additive is also called non-nutritive additive, and refers to some non-nutritive substances which are added into the feed for improving the utilization rate of the feed, ensuring the quality and quality of the feed and being beneficial to the health or metabolism of animals, and comprises growth promoters, insect repellent health care agents, seasoning and phagostimulants, feed conditioning agents, feed modulators, feed storage agents, probiotics, prebiotics and Chinese herbal medicine additives.
Further specifically, the non-nutritive additive is a growth promoter including, but not limited to, butyric acid, calcium butyrate, sodium butyrate, tannic acid, p-thymol ester, p-thymol salt, 2-hydroxybenzoic acid, beta-acid ester, beta-acid salt, hexahydrobeta-acid ester, hexahydrobeta-acid salt, benzoic acid or calcium benzoate, zinc oxide, zinc sulfate, zinc chloride.
In one embodiment, the non-nutritive additive is calcium butyrate.
In another embodiment, the non-nutritive additive is tannic acid.
Specifically, the pharmaceutical feed additive includes, but is not limited to, veterinary drug premix substances having effects of preventing animal diseases, promoting animal growth, and incorporating carriers or diluents for long-term use as additives in feeds.
More specifically, the pharmaceutical feed additive is a feed antibiotic, and the feed antibiotic includes, but is not limited to, polymyxin, salinomycin, avilamycin, bacitracin, virginiamycin, nosiheptide, flavomycin, enramycin, griseofulvin, olaquindox, oxytetracycline, or chlortetracycline.
In some embodiments, the composition comprising the fatty acyl derivative of aspartic acid and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof, further comprises one or more of a nutraceutical feed additive, a general feed additive and a pharmaceutical feed additive.
In some embodiments, the animal feed material is a feed material such as grains and processed products thereof, oil seeds and processed products thereof, legume seeds and processed products thereof, tubers, root tubers and processed products thereof, other seeds, fruit products and processed products thereof, forage grass, roughage and processed products thereof, other plants, algae and processed products thereof, dairy products and by-products thereof, terrestrial animal products and by-products thereof, fish, other aquatic organisms and by-products thereof, minerals, microbial fermentation products and by-products, other feed materials, and the like.
Use of a feed composition.
The invention relates to the use of the feeding composition comprising the fatty acyl derivative of aspartic acid and its racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt.
In some embodiments, the feed compositions comprising fatty acyl derivatives of aspartic acid and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof are used in the preparation of animal feed additives.
The animal feed additive prepared by the feed composition containing the aspartic acid fatty acyl derivative and the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate or the feed acceptable salt thereof is a livestock feed additive, a poultry feed additive, an aquaculture animal feed additive or a pet feed additive.
Specifically, the feed composition containing the aspartic acid fatty acyl derivative and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof is used for preparing a feed additive for livestock, wherein the livestock comprises but is not limited to pigs, cows, sheep, horses, rabbits, martens and the like at various growth stages.
Specifically, the feed composition containing the aspartic acid fatty acyl derivatives, and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof is used for preparing the feed additive for poultry, wherein the poultry comprises but is not limited to chickens, ducks, geese, pigeons and the like in various growth stages.
Specifically, the feed composition containing the aspartic acid fatty acyl derivative and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof is used for preparing the feed additive of the aquaculture animals, wherein the aquaculture animals comprise but are not limited to fishes, shrimps, crabs, soft-shelled turtles, eels and the like in various growth stages.
In particular, the feed composition containing the aspartic acid fatty acyl derivative and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof is used for preparing a pet feed additive, and pets include but are not limited to artificially fed dogs or cats.
In some embodiments, the animal feed additive prepared from the composition comprising the aspartic acid fatty acyl derivative and its racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt is a premix, a composite premix, an aqueous agent or granules.
In some embodiments, the feed composition comprising the fatty acyl derivatives of aspartic acid and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof is used in the preparation of animal feed.
The animal feed prepared by the feed composition containing the aspartic acid fatty acyl derivative and the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate or the feed acceptable salt thereof is livestock feed, poultry feed, aquaculture animal feed or pet feed.
Specifically, the feed composition containing the aspartic acid fatty acyl derivative and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof is used for preparing the feed for livestock, wherein the livestock comprises but is not limited to pigs, cows, sheep, horses, rabbits, martens and the like at various growth stages.
Specifically, the feed composition containing the aspartic acid fatty acyl derivative and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof is used for preparing the feed for poultry, wherein the poultry comprises but is not limited to chickens, ducks, geese, pigeons and the like in various growth stages.
Specifically, the feed composition containing aspartic acid fatty acyl derivatives, racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof is used for preparing the feed of aquaculture animals, wherein the aquaculture animals comprise but are not limited to fish, shrimp, crab, turtle, eel and the like in various growth stages.
In particular, the feed composition containing the aspartic acid fatty acyl derivative and racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt thereof is used for preparing pet feed, and pets include, but are not limited to, artificially fed dogs or cats.
In some embodiments, the feed prepared from the feeding composition comprising the fatty acyl derivative of aspartic acid and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof is a single feed, a concentrated feed, a compound premix or a concentrate supplement.
Specifically, the compound feed is complete compound feed.
A method for improving the production performance of farmed animals.
In some embodiments of the farming, the farmer can significantly improve the production performance of animals by administering to the animals a feed additive comprising an aspartic acid fatty acyl derivative and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof, concomitantly with the feed.
In some embodiments, the feed additive is a premix, a compound premix, granules or an aqueous solution, and is mixed with an animal feed to be eaten by animals.
The animal is livestock, poultry, aquaculture animal or pet.
Specifically, the domestic animals include, but are not limited to, pigs, cows, sheep, horses, rabbits, minks, etc. at various stages of growth; the poultry includes but is not limited to chickens, ducks, geese, pigeons and the like in all growth stages; the aquaculture animals include, but are not limited to, fish, shrimp, crab, soft-shelled turtle, eel and the like in all growth stages; the pets include, but are not limited to, artificially raised dogs or cats.
In one embodiment, the farmer administers a feed additive comprising an aspartic acid fatty acyl derivative and its racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt to weaned pigs along with the feed, significantly increasing the weight gain of average daily gain and increasing the feed conversion ratio of weaned pigs.
In one embodiment, the fatty acyl derivative of aspartic acid contained in the feed additive which is taken with feed by farmers and is eaten by weaned pigs is zinc N-butyryl-L-aspartate, so that the feed intake and average daily gain of the weaned pigs are improved, and the feed conversion rate is effectively improved, wherein the feed additive achieves the level of improving the production performance of the weaned pigs by high-dose inorganic zinc.
In another embodiment, the fatty acyl derivative of aspartic acid contained in a feed additive to be administered to weaned pigs by farmers in conjunction with the feed is copper salt of N-butyryl-L-aspartic acid, which significantly increases the average daily gain of weaned pigs and effectively increases the feed conversion rate, said feed additive achieving a level of improvement in the productivity of weaned pigs with high doses of inorganic copper.
In one embodiment, the farmer takes the feed additive containing the aspartic acid fatty acyl derivatives, and the racemates, the stereoisomers, the geometric isomers, the tautomers, the solvates or the acceptable salts of the feed, together with the feed to the broilers, so that the weight gain of the broilers is obviously improved, and the conversion rate of the feed is effectively improved.
In one embodiment, the farmer administers a feed additive comprising an aspartic acid fatty acyl derivative and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof to the fish with the feed.
In one embodiment, the farmer administers a feed additive comprising an aspartic acid fatty acyl derivative and its racemate, stereoisomer, geometric isomer, tautomer, solvate or feed acceptable salt to puppies with the feed.
In other feeding embodiments, a farmer can significantly improve the production performance of an animal by administering to the animal a feed composition comprising an aspartic acid fatty acyl derivative and racemates, stereoisomers, geometric isomers, tautomers, solvates or feed acceptable salts thereof.
Optionally, the feeding composition is a feed additive premix, a feed additive compound premix, granules or an aqueous solution, and is taken together with the feed for animals.
In one embodiment, the feeding composition is a feed additive premix.
In one embodiment, the feeding composition is a feed additive compound premix.
Optionally, the feeding composition is a concentrated feed, a compound premix or a concentrate supplement, and is directly fed to animals as animal feed.
In one embodiment, the feed composition is a complete formula feed.
Reference will now be made in detail to certain embodiments of the invention, examples of which are illustrated by the accompanying structural and chemical formulas. The invention is intended to cover alternatives, modifications and equivalents, which may be included within the scope of the invention as defined by the appended claims. Furthermore, certain features of the invention, which are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment or in any suitable subcombination.
The specific implementation mode is as follows:
in order to make the objects, technical solutions and advantages of the present invention more apparent, the compounds, compositions and applications of the present invention are further described in detail by examples below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Preparation of Compounds A
The method for preparing the fatty acyl derivative of aspartic acid will be described in detail below by taking only the preparation process of N-butyryl-L-aspartic acid, ethyl N-butyryl-L-aspartate and one of the salts thereof as an example, and other fatty acyl derivatives of aspartic acid can be prepared by reference thereto.
EXAMPLE A1 preparation of N-butyryl-L-aspartic acid
Figure BDA0002168830270000141
100.0g (0.75mol, 1eq) of L-aspartic acid was dissolved in 400mL of water containing 60.2g (1.50mol, 1.5eq) of sodium hydroxide at room temperature, the solution was dissolved and clarified by stirring, 106.4g (0.67mol, 0.89eq) of butyric anhydride was slowly dropped, the pH of the reaction solution was controlled to about 8 by 6mol/L of an aqueous sodium hydroxide solution during the reaction, and the reaction solution was stirred at room temperature for 24 hours. After the reaction, the reaction mixture was adjusted to pH 2 with concentrated hydrochloric acid, extracted with ethyl acetate (600 mL. Times.2), and the ethyl acetate layers were combined, dried over anhydrous sodium sulfate, and concentrated to give a crude product as an oil. The crude product was recrystallized from petroleum ether to precipitate a white solid, which was filtered and dried to give 100g (0.49 mol) of a white solid product with a yield of 65.3%.
1 HNMR(500MHz,DMSO-d6):δ(ppm)8.05(d,1H),4.95(q,1H),2.51-2.69(m,2H),2.05(t,2H),1.46(q,H),0.83(t,3H).
Example A2 preparation of iron N-butyryl-L-aspartate
Figure BDA0002168830270000142
22.2g (0.08mol, 0.67eq) of ferric trichloride hexahydrate is dissolved in 100mL of water at room temperature, 25g (0.12mol, 1eq) of N-butyryl-L-aspartic acid is dissolved in 100mL of aqueous solution containing 9.85g (1.50mol, 1.5eq) of sodium hydroxide under stirring, then the solution is slowly dripped into a reaction system, an iron red solid is generated, the reaction is continuously stirred for 5.0h, then the solution is filtered, and a filter cake is washed with water and dried to obtain 27g (0.086 mol) of the iron red solid, wherein the yield is 71.7%.
EXAMPLE A3 preparation of N-butyryl-L-aspartic acid diethyl ester
Figure BDA0002168830270000143
Step 1: synthesis of L-aspartic acid diethyl ester hydrochloride
320mL (5.48mol, 40eq.) of absolute ethanol was added to a 1000mL single-neck flask, cooled to-10 degrees, and 28mL (378.92mmol, 2.8eq.) of SOCl was added dropwise thereto 2 Controlling the dropping speed to control the temperature of the solution to be about-10 ℃, stirring the solution for 1 hour at the temperature of-10 ℃ after the dropping is finished, adding 18.16g (136.48mmol, 1eq.) of L-aspartic acid into the solution, stirring the solution for 2 hours at room temperature, reacting the solution at the temperature of 80 ℃, detecting the reaction by a TLC plate, decompressing and spin-drying the solvent after the reaction is finished, adding a small amount of absolute ethyl alcohol into the solution for several times, and cooling the solution in a refrigerator overnightAnd precipitating a solid, recrystallizing the solid with ethyl acetate, filtering, and drying to obtain 18.08g of white solid with the yield of 58.70%. ESI [ M-Cl ]] + 190， 1 HNMR(500MHz,D 2 O)δ:1.11(t,3H),1.24(t,3H),2.19(m,2H),2.58(td,2H),4.21(m,2H),5.14(m,1H)。
Step 2: synthesis of butyryl L-aspartic acid diethyl ester
Weighing 23.92g (106.00mmol, 1eq.) of L-aspartic acid diethyl ester hydrochloride into a 500mL single-neck bottle, adding 150mL of DCM for dissolution, adding 26.93g (266.13mmol, 2.5eq.) of triethylamine, cooling to 0 ℃, then dropwise adding a solution of 17.07g (160.21mmol, 1.5eq.) of butyryl chloride in 50mL of DCM, controlling the temperature at about 0 ℃ when the butyryl chloride is dropwise added, stirring at 0 ℃ for 1 hour after the dropwise adding is finished, then raising the temperature to room temperature for reaction for 2 hours, and stopping the reaction. To 100mL of water was added the organic phase was separated, the aqueous phase was extracted 2 times with DCM, the organic phases were combined, the organic phase was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 12.47g of a colorless liquid with a yield of 45.36%. ESI [ M + H ]] + 260， 1 HNMR(500MHz,DMSO-d6):δ0.67(t,3H),1.06(t,3H),1.20(t,3H),1.38(m,2H),2.05(m,2H),2.91(m,2H),4.04(q,2H),4.11(q,2H),5.02(td,1H),7.99(d,1H).
Example B stability study of aspartic acid fatty acyl derivatives
The change of the content of the main component of each of the aspartic acid fatty acyl derivative and the premix with the mass fraction of 5% (hereinafter referred to as 5% premix) with time under the stability test condition at 60 ℃ is examined.
The experimental instruments include a drug stability incubator, a Waters High Performance Liquid Chromatograph (HPLC), and the like.
The experimental reagent comprises raw materials (standard substances) of aspartic acid fatty acyl derivatives shown in the table 1, methanol (chromatographic grade) and phosphoric acid (analytically pure).
Preparation of standard solution: accurately weighing 100mg of aspartic acid fatty acyl derivative standard substance, adding 25mL of water, and ultrasonically dissolving to prepare working stock solution. Taking a proper amount of working stock solution, diluting the working stock solution with water respectively to obtain working solutions with the concentrations of 500ppm, 1000ppm, 2000ppm and 4000ppm, and detecting by HPLC. And (5) checking whether the sample concentration and the HPLC peak area response value are linear or not, and making a standard curve. The preparation method of the standard solution of the metal ion salt if the aspartic acid fatty acyl derivative is the standard solution comprises the steps of accurately weighing 50mg of the standard product, adding 25mL of 5% hydrochloric acid solution, and ultrasonically dissolving for 30min until the solution is completely dissolved to prepare the working stock solution. Taking a proper amount of working stock solution, diluting the working stock solution with 5% hydrochloric acid solution to working solutions with the concentrations of 250ppm, 500ppm, 1000ppm and 2000ppm respectively, testing HPLC (high performance liquid chromatography), and checking whether the sample concentration and the HPLC peak area response value are linear or not to make a standard curve.
Preparing a test solution: accurately weighing appropriate amount of aspartic acid fatty acyl derivative raw materials, 5% premix and 5% feed, adding appropriate amount of water, ultrasonic dissolving, preparing 4000ppm solution, filtering with 0.22 μm filter membrane, and performing HPLC analysis. If the aspartic acid fatty acyl derivative is a metal ion salt, accurately weighing a proper amount of aspartic acid fatty acyl derivative, adding 25mL of 5% hydrochloric acid solution, performing ultrasonic dissolution for 30min until the aspartic acid fatty acyl derivative is completely dissolved, preparing 2000ppm solution, filtering by a 0.22 mu m filter membrane, and performing HPLC analysis.
HPLC detection conditions: a chromatographic column: waters C18 columns (250mm 4.6mm,5 μm). Mobile phase: 0.02% phosphoric acid: methanol; (gradient elution: methanol: 5% → 40% (0-25 min) curve 6, 40% → 80% (25-30 min) curve 6, 80% methanol (31 min) curve 6, 80% → 5% (31-32 min) curve 1,5% methanol (32-37 min) curve 1, total time 37min; detection wavelength: 210nm; column temperature: 25 ℃ C.; sample introduction: 20. Mu.L; flow rate: 1ml/min.
The test method comprises the following steps: 60 ℃ stability test: aspartic acid fatty acyl derivative raw material and 5% of premix sample thereof are placed in a culture dish, spread into a thin layer with the thickness less than or equal to 5mm, placed at 60 ℃, sampled for HPLC detection on the 5 th day and the 10 th day, and each sample is sampled in parallel for three times.
And (3) test results: the test results are expressed as "average values" as shown in table 1. From the test results, the content of fatty acyl derivatives of aspartic acid, whether starting material or in premix, did not change significantly in the very good stability to high heat at 60 ℃ during the test.
TABLE 1 stability influencing factor study of aspartic acid fatty acyl derivatives
Figure BDA0002168830270000161
Figure BDA0002168830270000171
B cultivation test
Example B1 Effect of aspartic acid fatty acyl derivatives and salts thereof on weaned pig Productivity
390 pigs with similar body weights in clinical examination are selected from 100 nest 28 +/-2 days old 'Du Changda' ternary hybrid weaned pigs and are randomly divided into 13 groups, each group has 3 repetitions, and each repetition has 10 male and female halves. The piglets are attracted from the age of 7 days, the weaned piggery of 28 days is a cement floor, and the air is well ventilated and the temperature is proper. The pigsty and the apparatus were sterilized before the test. In the test period, test pigs are housed in different groups under the same feeding management condition in the same pigpen, and are fed and drunk freely; cleaning the pigsty once a day, and washing the ground once every three days to keep clean and sanitary conditions; feed 3 times a day. Each test component is a control group and a test group. Group I is a control group, and piglets are fed with basic ration; the fatty acyl derivatives of aspartic acid with the amount of 45ppm are respectively added on the basis of the basic ration fed by the piglets of the experimental groups II to VIII, as shown in the table 2; the daily ration fed by the piglets of the IV-VIII groups is the basic daily ration, and 1000ppm of N-butyryl-L-aspartic acid metal ion salt is added on the basis of the basic daily ration, as shown in the table 2. In the whole feeding process, other antioxidant ingredients and growth promoters are not additionally added in each test group, and the test period is 40 days. During the test period, piglets were observed daily for feed and health and the remaining ration was weighed, feed consumption was recorded and the test pigs were weighed at 7-00 am for 0 and 40 days, and the average daily feed intake (ADFI, g/d) average daily gain (ADG, g/d) and Feed Conversion Ratio (FCR) were calculated. The calculation formula is as follows:
average daily feed intake = (total amount of ingredients-amount of remaining material)/(number of test days × number of pigs per replicate);
average daily gain = (end-trial average body weight-initial average body weight)/number of trial days;
feed-meat ratio = average daily feed intake/average daily gain.
Statistical analysis is carried out on test data by SPSS18 software, single-factor analysis of variance (ANOVA) is carried out on the data, if the difference between treatments is obvious, multiple comparison is carried out by a Duncan's method, and the significance level is 0.05. The test results are expressed as "mean ± sem", and the test results are shown in table 2.
According to the feeding test results of the weaned piglets, the feed intake of the weaned piglets in each group is improved in the aspect of average daily feed intake compared with that of a blank control group, wherein the effects of the zinc salts of the N-decanoyl-L-aspartic acid and the N-butyryl-L-aspartic acid are very obvious; with respect to the average daily gain, the average daily gain of the weaned pigs in each group is improved compared with that of a blank control group, wherein the effect on sodium salt, zinc salt, iron salt and calcium salt of N-decanoyl-L-aspartic acid, diethyl N-butyryl-L-aspartic acid and N-butyryl-L-aspartic acid is more obvious; in the aspect of feed-meat ratio, compared with a control group, the effect of each test does not change remarkably, but the reduction range is 5-7%.
TABLE 2 fatty acyl derivatives of aspartic acid and their salts on the impact on the productivity of weaned piglets
Figure BDA0002168830270000172
Figure BDA0002168830270000181
Example B2 Effect of aspartic acid fatty acyl derivatives on laying hen Productivity
The test adopts single-factor random design, 480 Jingbai laying hens of 147 days old and similar body weight are selected and randomly divided into 8 treatment groups, each group has 3 repetitions, each group has half of a male group, and each group has 20 repetitions of the Jingbai laying hens. The chicken coop and the appliances were sterilized before the test. In the test period, cage culture is carried out in the same chicken house under the same feeding management condition. The basic daily ration mainly comprises corn-soybean meal, and other antioxidant ingredients and growth promoters are not additionally added in the whole feeding process. Each test group is a test group I to VIII. Wherein test I is a control group given only basal ration, and tests II-VIII were provided with 500ppm of different aspartic acid fatty acyl derivatives in the basal ration, respectively, as shown in Table 3. The pre-feeding period is 10 days, the testing period is 158 days, the test chicken freely drinks water and takes food, and the feeding is carried out for 2 times daily. During the test, the egg production, feed intake were recorded in the unit of repetition every day, and the Egg Production Rate (EPR), average daily feed intake (ADFI, g/d), egg weight (EW, g) and feed-to-egg ratio (FER) of the laying hens at the whole period of the test were calculated. The calculation formula is as follows:
laying rate (%) = average total eggs per day/number of chickens × 100;
egg weight (g) = average total daily egg weight/average total daily egg count;
feed-egg ratio = average daily feed intake/egg weight.
Statistical analysis is carried out on test data by SPSS18 software, single-factor analysis of variance (ANOVA) is carried out on the data, if the difference between treatments is obvious, multiple comparison is carried out by a Duncan's method, and the significance level is 0.05. The test results are expressed as "mean. + -. Standard error" and are shown in Table 3.
The results show that the test article has no significant effect on the laying rate and the feed-egg ratio of the test chicken compared with the control group, but shows the improvement effect of different degrees, the laying rate is increased by 1.9-5.5%, and the feed-egg ratio is reduced by 2.3-6.4%; the test article has no influence on the feed intake and the egg weight of the test chicken.
TABLE 3 application effect study of aspartic acid fatty acyl derivatives in layer feed
Figure BDA0002168830270000191
Example B3 Effect of fatty acyl derivatives of aspartic acid on broiler Productivity
The test adopts single-factor random design, 480 three yellow-feathered broilers with the average weight of 50g and the age of 1 day and the similar weight are selected and randomly divided into 8 treatment groups, each group has 3 repetitions, each group has half of a male parent, and each repetition has 20 yellow-feathered broilers. The chicken coop and the appliances were sterilized before the test. In the test period, cage culture is carried out in the same chicken house under the same feeding management condition. The basic daily ration mainly comprises corn-soybean meal, and other antioxidant ingredients and growth promoters are not additionally added in the whole feeding process. Each test group is a test group I to VIII. Wherein test I is a control group given only basal ration, and tests II-VIII were prepared by adding 300ppm of different fatty acyl derivatives of aspartic acid to the basal ration, respectively, as shown in Table 4. The test period is 20 days, and the test chicken freely drinks and takes food and feeds for 2 times a day. Weighing each repetition at 21 days of age (stopping feed for 12h without stopping water), counting the feed consumption of test chickens, and calculating the average daily feed intake (ADFI, g/d), average daily gain (ADG, g/d) and Feed Conversion Ratio (FCR) of each group of test chickens, wherein the calculation formula is as follows:
feed-meat ratio (FCR) = average daily food intake/average daily gain.
Statistical analysis is carried out on test data by SPSS18 software, single-factor analysis of variance (ANOVA) is carried out on the data, if the difference between treatments is obvious, multiple comparison is carried out by a Duncan's method, and the significance level is 0.05. The test results are expressed as "mean. + -. Standard error" and are shown in Table 4.
From the results, the aspartic acid fatty acyl derivatives involved in the test have no significant influence on the feed intake and the feed-to-meat ratio of the broilers during the test period in the broiler breeding, but have different degrees of improvement effects on the feed-to-meat ratio of the broilers; in addition, the test article has a remarkable effect of improving the weight gain of the broiler chicken, so that the fatty acyl derivative of the aspartic acid has a remarkable effect of improving the production performance of the broiler chicken on the whole.
TABLE 4 application effect study of fatty acyl derivatives of aspartic acid in broiler feed
Figure BDA0002168830270000201
Example B4 use of fatty acyl derivatives of aspartic acid in Fish feed
1) Test materials
The fish used for the test: the test fish is the live grass carp seeds with the same size and health in the same year in a large net cage (4X 2X 1.5 m) 3 ) The culture is carried out for 4 weeks before the culture is carried out for formal culture tests, and the experimental system is a small floating net cage (the specification is 1.1 multiplied by 1.1 m) 3 ) Each small net cage is provided with an inflation head, and 24 hours of air inflation is carried out every day. The small net cage and the temporary culture net cage are placed in a test field with a height of 3500m 2 The depth of the pond water in the pond is about 1.5m, and the pond water is fully aerated bottom water. During the test, the grass carp 640 after hungry for 1 day is randomly divided into 8 groups, each group is provided with 4 repeats, 20 fishes are placed in each repeat, the 20 fishes are weighed by taking each repeat as a unit and then placed into 32 net boxes, and the grass carp is fed with test feeds added with different test products with the same content.
Test feed: the test feed is prepared according to the formula shown in the table 5, and different test groups are fed with different test products with the same content according to the table 6. The feed raw materials are subjected to superfine grinding and then are prepared into buoyancy expanded feed with the particle size of 3mm by a Jiangsu shepherd expansion machine set, the mold stripping temperature is 130 ℃, 3% of soybean oil is sprayed outside by oil spraying equipment, and the feed is sealed and stored in a shade place for later use.
Table 5 grass carp feed formulation and chemical composition (% by weight) for the test
Figure BDA0002168830270000202
Figure BDA0002168830270000211
TABLE 6 application study groups of fatty acyl derivatives of aspartic acid in fish feed
Group of Test article Dosage (ppm)
Group I - -
Group II N-acetyl-L-aspartic acid 3000
Group III N-butyryl-L-aspartic acid 3000
Group IV N-decanoyl-L-aspartic acid 3000
Group V N-lauroyl-L-aspartic acid 3000
Group VI N-myristoyl-L-aspartic acid 3000
Group VII N-stearoyl-L-aspartic acid 3000
Group VIII N-butyryl-L-aspartic acid diethyl ester 3000
(2) Test method
And (3) test management: the test was carried out with manual feeding restriction, the feeding amount was adjusted once a week, the feeding level (according to the initial body weight) was completely consistent for each group, two times a day (7. The test period was 8 weeks. The water quality is monitored regularly during the test period, the water temperature is 26.88 +/-3.08 ℃ and DO is kept in the whole cultivation process>5.0mg O L -1 pH 7.8, ammonia nitrogen<0.50mg N L -1 Nitrite nitrogen<0.05mg N L -1 。
And (3) parameter statistics: during the test, the net cages are weighed integrally after the feeding is stopped for 1d, and the weight gain ratio (WG,%) and the Feed Coefficient (FCR) are calculated. The calculation formula is as follows:
weight gain ratio (WG,%) =100 × (average final weight-average initial weight)/average initial weight;
feed Factor (FCR) = food intake/fish body weight gain.
(3) Test results
As can be seen from the test results shown in table 7, the fatty acyl derivative of aspartic acid significantly increased the weight gain and decreased the feed factor of grass carp in the breeding test of grass carp but the effect of decreasing the feed factor was not significant except for N-myristoyl-aspartic acid.
TABLE 7 results of fatty acyl derivatives of aspartic acid in aquatic feed
Figure BDA0002168830270000221
The above-described embodiments are merely illustrative of some of the various ways in which the invention may be practiced and are intended to be covered by other embodiments. Accordingly, the embodiments of the present invention will be described by way of illustration, but not construed to limit the scope of the invention, and modifications made within the scope and spirit of the invention or equivalents added to the claims are possible.

Claims (14)

1. The application of an aspartic acid fatty acyl derivative or a feed acceptable salt thereof with the structure shown as the following general formula in preparing an animal feed additive for improving the production performance of animals:
Figure FDA0003727977940000011
wherein Y and X are independently selected from C 1 -C 20 Alkoxy or OH; r 1 Is R 1a C(＝O)、R 1a S(＝O) 2 Or H; r 2 Is R 2a C (= O) or R 2a S(＝O) 2 (ii) a Said R 1a And R 2a Are each independently selected from C 1 -C 20 Alkyl or C 3 -C 7 A cycloalkyl group.
2. The use of claim 1, wherein R is 1 Is H.
3. The use of claim 1, wherein R is 2 Is R 2a C(＝O)，R 2a Is selected from C 1 -C 20 Alkyl or C 3 -C 7 A cycloalkyl group.
4. The use of claim 3, wherein R is 2a Is selected from C 1 -C 10 An alkyl group.
5. The use according to claim 1, wherein Y and X are OH.
6. The use according to claim 1, wherein Y and X are each independently selected from C 1 -C 20 Alkoxy or OH, and not simultaneously OH.
7. The use according to claim 6, wherein Y and X are each independently selected from C 1 -C 10 Alkoxy or OH, and not simultaneously OH.
8. The use according to claim 1, wherein the feed acceptable salt is a metal ion salt.
9. The use of claim 8, wherein the metal ion salt is a sodium ion salt, a calcium ion salt, a zinc ion salt, a copper ion salt, or an iron ion salt.
10. A feeding composition comprising at least one of the fatty acyl derivatives of aspartic acid or a feed acceptable salt thereof as claimed in any one of claims 1 to 9 and a feedable adjuvant.
11. The feeding composition of claim 10 further comprising an additional animal feed additive selected from the group consisting of a nutritive feed additive, a non-nutritive feed additive, and a pharmaceutical feed additive.
12. The feed composition of claim 10 or 11 further comprising an animal feed material.
13. Use of a feed composition as claimed in any of claims 10 to 12 in the preparation of an animal feed additive.
14. Use of the feed composition of any one of claims 10 to 12 in the preparation of animal feed.
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