CN110325052A - Asparatate fatty acyl group derivative is preparing the application in animal feed additive - Google Patents

Asparatate fatty acyl group derivative is preparing the application in animal feed additive Download PDF

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CN110325052A
CN110325052A CN201880012282.3A CN201880012282A CN110325052A CN 110325052 A CN110325052 A CN 110325052A CN 201880012282 A CN201880012282 A CN 201880012282A CN 110325052 A CN110325052 A CN 110325052A
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feed
asparatate
fatty acyl
acyl group
salt
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CN110325052B (en
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黄华成
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Peng Xianfeng
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
    • A23K10/37—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms from waste material
    • 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
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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
    • A23K20/142—Amino acids; Derivatives thereof
    • 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
    • A23K20/142—Amino acids; Derivatives thereof
    • A23K20/147—Polymeric derivatives, e.g. peptides or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
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    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
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    • A23K—FODDER
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    • A23K20/10—Organic substances
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
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    • A23K20/20—Inorganic substances, e.g. oligoelements
    • 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
    • A23K20/24—Compounds of alkaline earth metals, e.g. magnesium
    • 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
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    • A23K20/28—Silicates, e.g. perlites, zeolites or bentonites
    • 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
    • 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
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • 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
    • A23K50/60—Feeding-stuffs specially adapted for particular animals for weanlings
    • 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
    • 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
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
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Abstract

The acyl derivative or its raceme, stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed for disclosing a kind of structure asparatate as shown in formula (I) are preparing the application in animal feed additive; there is good improvement to the production performance of cultivated animalsWherein, Y and X are respectively and independently selected from C1‑C20Alkoxy or OH；R1For R1aC (=O), R1aS (=O)2Or H；R2For R2aC (=O) or R2aS (=O)2；The R1aAnd R2aIt is respectively and independently selected from C1‑C20Alkyl or C3‑C7Naphthenic base.

Description

Asparatate fatty acyl group derivative is preparing the application in animal feed additive
Technical field:
The invention belongs to animal feed additive fields, and in particular to asparatate fatty acyl group derivative is dynamic in preparation The application of object feed addictive and a kind of feeding composition comprising asparatate fatty acyl group derivative and its dynamic in preparation Application in object feed addictive and animal feed.
Background technique:
Asparatate is nonessential amino acid in animal body.N-, which is acylated asparatate, has fatty mouthfeel, strong Low calorie fat substitute is used as in health food.It is a kind of amino acid surfactant, bubble again that N-, which is acylated asparatate, Ability is good, stable storing, is the personal nursings such as toothpaste, kitchen cleaning agent, detergent for toilet, shampoo, shower cream and public health neck Domain.
Acetylation asparatate is ingredient and a kind of central nervous system substance in various plants or food, is The acetic acid donor of myelin liquid fatty acid, some researches show that acetylation asparatates to be shown thorn in people's gustatory system Swash the unpleasant mixing tart flavour of property.
Feed refers to the product used for animal through industrialization processing, production, is the master for modernizing intensive aquaculture industry Want animal foodstuff.During animal-breeding, the feed product that raiser thirsts for animal edible can be inhaled by animal to greatest extent It receives and utilizes, improve the production performance of animal to achieve the purpose that improve economic benefit of aquaculture.Adding in feed product has The feed addictive of corresponding effect can effectively improve the utilization rate of feed product.
Feed addictive refers to a small amount of or micro substance added in feed processing, production, use process, including Nutritional feed additive and general feeds additive.General feeds additive refers to guarantee or improving feed quality, mention High efficiency of feed utilization and mix a small amount of or micro substance in feed.This field it is currently used have efficiently and stably improve Efficiency of feed utilization improve the general feeds additive of breeding performonce fo animals mainly include high doses of copper agent, it is Pharmacological Level of Zinc agent, feeding Antibiotic, chemical synthesis antibacterial agent etc., still, these substances are larger using side effect for a long time in aquaculture, such as the liver of animal Renal toxicity inhibits growth, renal function damage, urinary-tract disorders, teratogenesis, mutagenesis, generates drug resistance, medicine residual and pollution environment Etc. drawbacks.In order to ensure the health of animal and improve the productivity effect of aquaculture, seek the new feedstuff of effective, stable safety Additive is this field urgent problem.
Summary of the invention:
Based on this, the present invention provides a kind of stabilization, effective asparatate fatty acyl group derivative or its raceme, vertical Body isomers, geometric isomer, tautomer, solvate and the acceptable salt of feed are in preparing animal feed additive Application；The present invention also provides one kind to include asparatate fatty acyl group derivative or its raceme, stereoisomer, several What isomers, tautomer, the feeding composition and the composition of solvate and the acceptable salt of feed are dynamic in preparation Application in object feed addictive and animal feed.
On the one hand, the present invention provides a kind of structure asparatate fatty acyl group derivative as shown in formula (I) or its Raceme, stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed are raised in preparation animal Application in feed additives:
In some technical solutions, Y and X are respectively and independently selected from C1-C20Alkoxy or OH；R1For R1aC (=O), R1aS (= O)2Or H；R2For R2aC (=O) or R2aS (=O)2；The R1aAnd R2aIt is respectively and independently selected from C1-C20Alkyl or C3-C7Cycloalkanes Base.
In some technical solutions, the R of the asparatate fatty acyl group derivative1For H.
In some technical solutions, the R of the asparatate fatty acyl group derivative2For R2aC (=O), R2aIt is selected from C1-C20Alkyl or C3-C7Naphthenic base.
In some technical solutions, the R of the asparatate fatty acyl group derivative2aSelected from C1-C10Alkyl.
In some technical solutions, the Y and X of the asparatate fatty acyl group derivative are OH.
In some technical solutions, the Y and X of the asparatate fatty acyl group derivative are respectively and independently selected from C1- C20Alkoxy or OH, and be not simultaneously OH.
In some technical solutions, the Y and X of the asparatate fatty acyl group derivative are respectively and independently selected from C1- C10Alkoxy or OH, and be not simultaneously OH.
In some technical solutions, the acceptable salt of feed of the asparatate fatty acyl group derivative is metal Ion salt.
In some technical solutions, the acceptable salt of feed of the asparatate fatty acyl group derivative is preferably Sodium ion salt, calcium ion salts, zinc ion salt, copper ion salt or iron ion salt.
On the other hand, the present invention provides a kind of feeding compositions, include asparatate fatty acyl of the present invention Radical derivative or its raceme, stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed At least one of and at least one can feeding auxiliary material.
It is described can feeding auxiliary material be selected from can be feeding carrier, diluent, adjuvant, solvent or their combination.
In some technical solutions, the feeding composition also includes animal feed raw material.
In some technical solutions, the feeding composition also includes additional animal feed additive.
In some technical solutions, the feeding composition also includes that animal feed raw material and additional animal feed add Add agent.
In some technical solutions, the additional animal feed additive can be selected from nutritional feed additive and/ Or general feeds additive and/or medicated feed additive.
On the other hand, the present invention provides the feeding compositions to prepare the application in animal feed additive.
On the other hand, the present invention provides the feeding compositions to prepare the application in animal feed.
On the other hand, the present invention also provides a kind of methods for improving cultivated animals production performance.
Beneficial effects of the present invention:
Animal-breeding test in the result shows that, asparatate fatty acyl group derivative provided by the invention or its racemization Body, stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed can be used as animal feed and adds Add agent application, has the effect of good improvement breeding performonce fo animals.
Any embodiment in either present invention face can be combined with other embodiments, as long as between them There is not contradiction.In addition, any technical characteristic can be adapted for other realities in any embodiment of either side of the present invention The technical characteristic in scheme is applied, as long as between them being not in contradiction.
Content noted earlier only outlines certain aspects of the invention, but is not limited to these aspects.It is above-mentioned to be related to content And otherwise content will do more specific complete description below.
Of the invention is described in further detail.
Certain embodiments of the present invention will now be described in more detail, the example is said by the structural formula and chemical formula being appended It is bright.The intent of the present invention covers all substitutions, modification and equivalent technical solution, they are included in claim such as and define The scope of the present invention in.In addition, certain technical characteristics of the invention be it is clearly visible, divide in a number of independent embodiments It is not described, but can also provide or be provided in the form of any suitable sub-portfolio in combination in a single embodiment.
Compound.
Compound of the present invention is a kind of structure asparatate fatty acyl group derivative as shown in formula (I),
Wherein, Y and X is the substituent group on the carboxyl of asparatate, R1And R2For the substitution on nitrogen-atoms (being abbreviated as N) Base.Y and X are respectively and independently selected from C1-C20Alkoxy or OH；R1For R1aC (=O), R1aS (=O)2Or H；R2For R2aC (=O) or R2aS (=O)2；The R1aAnd R2aIt is respectively and independently selected from C1-C20Alkyl or C3-C7Naphthenic base.
In general, it is " substituted " indicate one or more of given structure can substituted hydrogen atom by specific substituent group Replaced, the group of a substitution can have a substituent group to be replaced at various substitutable position of that group, when given Structural formula in more than one position can be replaced one or more substituent groups by specific group, then substituent group can be identical Or differently replace at various locations.
In the present invention, " C1-C20Alkyl " indicate the saturated alkyl containing 1 to 20 carbon atom, as methyl, ethyl, Propyl, isopropyl ..., the alkyl containing 20 carbon atoms of linear chain or branched chain；"C3-C7Naphthenic base " is expressed as comprising 3-7 The cyclic alkyl containing only hydrocarbon two kinds of elements of a carbon atom, such as cyclopropyl, 2- methylcyclopropyl groups, cyclopenta.
Optionally, the R of the asparatate fatty acyl group derivative1For R1aS (=O)2Or H, R2For R2aS (=O)2； The R1aAnd R2aIt is respectively and independently selected from C1-C20Alkyl or C3-C7Naphthenic base, the Y and X are respectively and independently selected from C1-C20Alkane Oxygroup or OH.
Further, the R1For H, R2For R2aS (=O)2；The R2aSelected from C1-C20Alkyl or C3-C7Naphthenic base, The Y and X is respectively and independently selected from C1-C20Alkoxy or OH.
Optionally, the R of the asparatate fatty acyl group derivative1For R1aC (=O) or H, R2For R2aC (=O)； The R1aAnd R2aIt is respectively and independently selected from C1-C20Alkyl or C3-C7Naphthenic base, the Y and X are respectively and independently selected from C1-C20Alkane Oxygroup or OH.
Further, the R1For H, R2For R2aC (=O)；The R2aSelected from C1-C20Alkyl or C3-C7Naphthenic base, The Y and X is respectively and independently selected from C1-C20Alkoxy or OH.
Optionally, the R1aOr R2aSelected from C1-C20Alkyl.
Further, the R1aOr R2aSelected from straight chain C1-C10Alkyl, specially methyl (CH3), ethyl (CH2CH3)、 N-propyl ((CH2)2CH3), normal-butyl ((CH2)3CH3), n-pentyl ((CH2)4CH3), just a few base ((CH2)5CH3), n-heptyl ((CH2)6CH3), n-octyl ((CH2)7CH3), n-nonyl ((CH2)8CH3), positive decyl ((CH2)9CH3One of).
Also optional, described R1aOr R2aSelected from branch C1-C10Alkyl, including but not limited to isopropyl ((CH3)2CH)、 Isobutyl group ((CH3)3C) etc..
Optionally, the Y and X of the asparatate fatty acyl group derivative are simultaneously OH.
Optionally, the Y and X of the asparatate fatty acyl group derivative are selected from C1-C20Alkoxy or OH, but it is different When be OH, specifically simultaneously be C1-C20Alkoxy or respectively C1-C20One of alkoxy and OH.
Further, the alkoxy is preferably the C of linear chain or branched chain1-C10Alkoxy, including but not limited to methoxyl group (OCH3), ethyoxyl (OCH2CH3), n-propane oxygroup (O (CH2)2CH3), isopropyl alkoxy (OCH2(CH3)2), normal butane oxygroup (O(CH2)3CH3), tertiary butane oxygroup (OC (CH3)3), pentane oxygroup (O (CH2)4CH3), just a few alkoxy (O (CH2)5CH3)、 Normal heptane oxygroup (O (CH2)6CH3), normal octane oxygroup (O (CH2)7CH3), n -nonane oxygroup (O (CH2)8CH3) or n-decane oxygroup (O(CH2)9CH3)。
Optionally, the acceptable salt of feed of the asparatate fatty acyl group derivative is metal cation salt, tool Body is monovalent metallic ion salt, bivalent metal ion salt or trivalent metal ion salts.
Specifically, the monovalent metallic ion includes but is not limited to sodium ion, potassium ion, lithium ion, ammonium ion；It is described Bivalent metal ion include but is not limited to calcium ion, magnesium ion, zinc ion, copper ion, ferrous ion, manganese ion；Described Trivalent metal ion includes but is not limited to iron ion, nickel ion, chromium ion, aluminium ion.
In some embodiments, the metal ion is zinc ion.
In further embodiments, the metal ion is copper ion.
In further embodiments, the metal ion is sodium ion.
In further embodiments, the metal ion is calcium ion.
In further embodiments, the metal ion is iron ion.
The preparation and purification of compound.
The preparation method of the asparatate fatty acyl group derivative of the present invention as shown in formula (I), with lucid asparagus Propylhomoserin (Asp) is starting material, and the chemical reaction being related to mainly includes the acylation of amino and the esterification of carboxyl.
In some embodiments, Y and X is C in formula (I)1-C20Alkoxy or OH but be not simultaneously OH, shown in formula (I) The preparation method of asparatate fatty acyl group derivative includes the esterification of carboxyl and the acylation two-step reaction of amino, such as formula (II) shown in.
Want X and R it is clear that in formula (II)1Substituent group is only indicated, if raw material X-H, R1OR1And R1Representated by-Cl Substance is not single substance then X or R1It should be understood as the set of substituent group.
In some embodiments, Y and X is simultaneously-OH in formula (I), and asparatate fatty acyl group shown in formula (I) spreads out Shown in the preparation method such as formula (III) of biology.
It will be clear that the R in formula (III)1Substituent group is only indicated, as raw material R1OR1The substance of expression is not single object R1 when matter then on target product (TM) should be understood as the set of substituent group.
Further, Y and X is simultaneously OH or respectively C1-C20The asparatate fatty acyl for the moment of alkoxy and OH Radical derivative is reacted with metal chloride or metal bromide under alkaline condition generates asparatate fatty acyl group derivative Metal cation salt, such as zinc salt, mantoquita, calcium salt, molysite or sodium salt metal cation salt of the present invention.
In some embodiments, the asparatate is a kind of chipal compounds, lucid asparagus of the present invention Propylhomoserin is selected from levo form L- (-)-asparatate (structure such as formula (IV)), d-isomer D- (+)-asparatate (structure such as formula (V)) or racemic modification DL- (±) asparatate, with obtain after the alcohol and carboxylic acid derivatives reaction that is related to chiral centre Asparatate fatty acyl group derivative stereoisomer or racemic modification.
In some embodiments, the chiral stereoisomer and asparatate fatty acyl group of the asparatate The conversion of spatial configuration can occur under suitable conditions for the stereoisomer of derivative, such as asparatate or asparatate The three-dimensional conformation interconversion of fatty acyl group derivative, such as shown in the three-dimensional conformation interconversion processes such as formula (VI) of asparatate:
Derive when the reactive material being related to generates corresponding asparatate fatty acyl group with reactions such as asparatates When object has rigid structure, reaction substrate produces different geometric isomer products during the reaction.
Above-mentioned stereoisomer, geometric isomer, tautomer are also included in practical range of the invention.
" stereoisomer " of the present invention refers to identical chemical constitution, but the row of atom or group spatially The different compound of column mode, including enantiomter, diastereoisomer, conformer, geometric isomer, resistance turn isomery Body etc.." enantiomter " refers to two isomers that cannot be overlapped but be mutually mirror of a compound.It is " diastereomeric different Structure body " refer to there are two or multiple chiral centres and its molecule not stereoisomer of mirror image each other, have different fusing points, The physical properties such as boiling point, spectral property and reactivity.Non-corresponding isomer mixture can operate such as electrophoresis by high resolution analysis Or chromatography separates；" tautomer " refers to that with different energy can be by the constitutional isomer of the mutual inversion of phases of low energy barrier.
In some embodiments, the preparation process that the present invention provides asparatate fatty acyl group derivative further relates to instead Answer the separation, purifying or recrystallization process of product.Reaction product can obtain crude product by desolventizing method from reaction system.In order to Obtain that chemical purity is higher, the lower solid matter of impurity content, crude product through alcoholic solvent, alcohol water mixed solvent or other can be used for In the organic solvent of product recrystallization under the conditions ofs suitable temperature, illumination and mechanical oscillation etc. dissolution, crystallization or precipitating or Recrystallization and the isolated asparatate fatty acyl group derivative with certain crystal form state.It is described that there is certain crystal form shape The asparatate fatty acyl group derivative of state is the crystallization of asparatate fatty acyl group derivative or asparatate fatty acyl The solvate of radical derivative.The solvate of the asparatate fatty acyl group derivative can be selected from asparatate rouge The hydrate of fat acyl derivative or the ethanolates of aspartic acid derivate.
During " solvate " of the present invention refers to that the compound of the present invention is contacted with solvent molecule, outer strip Part and interior condition factor cause through the solvent molecule of chemical equivalent in conjunction with non-covalent intermolecular forces or non-chemical equivalent and The eutectic associated matter of formation.Formed solvate solvent include but is not limited to water, acetone, ethyl alcohol, methanol, dimethyl sulfoxide, Ethyl acetate, acetic acid, isopropanol equal solvent." hydrate " refers to that solvent molecule is that water is formed by associated matter or crystalline solid, It is exactly the compound of the water by non-covalent intermolecular forces combination chemical equivalent or non-chemical equivalent.
In order to obtain, chemical purity is higher, impurity contains for the preparation of asparatate fatty acyl group derivative provided by the invention Measure lower solid matter can also be by being handled after salting out method.The salting out method is matched using acid-base neutralization method, soda acid The principle of position method or soda acid chelating method makes aspartic acid derivate and corresponding organic base, inorganic base, organic acid or inorganic acid At the process that salt precipitates, the acceptable salt of feed is obtained.
The acceptable salt of feed be asparatate fatty acyl group derivative of the invention and the organic base nontoxic to animal, The salt that inorganic base, organic acid or inorganic acid are formed." feed is acceptable " refers to substance or composition must be suitable It is chemical or toxicology, it is related with the feed of composition or edible cultivated animals.
In some embodiments, asparatate fatty acyl group derivative is that (namely Y and X are same for dibasic acid esters or mixed ester When for identical or different C1-C20Alkyl), the salt precipitation process and inorganic acid or organic acid of post-processing form soda acid coordination salt And/or soda acid chelating salt, the organic acid include but is not limited to acetate, maleate, succinate, mandelate, prolong recklessly Rope hydrochlorate, malonate, malate, 2 hydroxy propanoic acid salt, acetonate, oxalates, glycollate, salicylate, grape Glycuronate, galactitol hydrochlorate, citrate, tartrate, aspartate, glutamate, benzoate, to methylbenzene Formates, cinnamate, tosilate, benzene sulfonate, mesylate, esilate, fluoroform sulphonate or they Combination；The inorganic acid includes but is not limited to hydrochloride, hydrobromate, phosphate, sulfate, nitrate or their group It closes.
In some embodiments, asparatate fatty acyl group derivative is that (namely Y and X are respectively C to monoesters1-C20 One of alkyl and H), the salt precipitation process and organic acid or inorganic acid of post-processing form soda acid coordination salt and/or soda acid chelates Salt, or acid salt is formed with organic base or inorganic base.The organic acid includes but is not limited to acetate, maleate, amber Hydrochlorate, mandelate, fumarate, malonate, malate, 2 hydroxy propanoic acid salt, acetonate, oxalates, ethyl alcohol Hydrochlorate, salicylate, glucuronate salt, galactitol hydrochlorate, citrate, tartrate, aspartate, glutamic acid Salt, benzoate, p-methylbenzoic acid salt, cinnamate, tosilate, benzene sulfonate, mesylate, esilate, Fluoroform sulphonate or their combination；The inorganic acid includes but is not limited to hydrochloride, hydrobromate, phosphate, sulfuric acid Salt, nitrate or their combination.The organic base includes but is not limited to ammonia or triethylamine.The inorganic base includes but not It is limited to sodium hydroxide, potassium hydroxide, magnesium hydroxide or calcium hydroxide.
The stability study of the fatty acyl group derivative of asparatate.
Asparatate fatty acyl group derivative or its raceme provided by the invention, stereoisomer, geometric isomer, Tautomer, solvate or the acceptable salt of feed measure the stability of compound under the conditions of 60 DEG C, and the test period is 10 days, the content of compound was as there is no significant changes for the variation of time within experimental period.
The present invention relates to the applications of the fatty acyl group derivative of asparatate.
Structure provided by the invention asparatate fatty acyl group derivative and its raceme, alloisomerism as shown in (I) Body, geometric isomer, tautomer, solvate or the acceptable salt of feed are applied in preparing animal feed additive.
" animal " of the present invention refer to cannot by inorganic matter synthesis of organic substance, can only using organic matter as foodstuff, with It ingested, digested, absorbed, breathed, recycled, drained, felt, moved and is bred etc. as the movable people of life or cultivated animals. " cultivated animals " include that other animals of poultry, domestic animal, aquiculture animal and the legal capture of artificial feeding include pet, example Such as cat and dog.Term " domestic animal " is, for example, pig, ox, horse, goat, sheep, deer and many useful rodents it is any.Term " poultry " is, such as chicken, duck, goose, quail, dove etc..Term " aquiculture animal " includes, such as fish, shrimp, tortoise, soft-shelled turtle.
Using fatty acyl group derivative and its raceme, stereoisomer, the geometry of asparatate provided by the invention Prepared by isomers, tautomer, solvate or the acceptable salt of feed is changing for the animal as each growth phase The non-nutritive additive of kind breeding performonce fo animals, the animal can be selected from the domestic animal, poultry, aquaculture of each growth phase Animal or pet.
Optionally, the domestic animal includes but is not limited to pig, ox, sheep, horse, rabbit, ermine or donkey, and the poultry includes but not Be limited to chicken, turkey, duck, goose, quail or dove, the aquiculture animal include but is not limited to fish, shrimp, tortoise, crab, soft-shelled turtle, bullfrog, Eel or loach, the pet include but is not limited to the dog or cat of each subspecies.
In one embodiment, using the fatty acyl group derivative and its raceme of asparatate provided by the invention, vertical Prepared by body isomers, geometric isomer, tautomer, solvate or the acceptable salt of feed is that wean pig's feed adds Add agent, the average daily gain of wean pig is effectively promoted while the feed intake of wean pig can be improved and improves feed conversion rate.
In another embodiment, using the fatty acyl group derivative and its raceme of asparatate provided by the invention, Prepared by stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed is raised as laying hen Feed additives can effectively improve the laying rate of laying hen, improve egg size and reduce the feedstuff-egg ratio of laying hen.
In another embodiment, using the fatty acyl group derivative and its raceme of asparatate provided by the invention, Stereoisomer, geometric isomer, tautomer, solvate or the feed addictive of the acceptable salt preparation of feed can be shown Write the production performance for improving broiler chicken.
In another embodiment, using the fatty acyl group derivative and its raceme of asparatate provided by the invention, Stereoisomer, geometric isomer, tautomer, solvate or the feed addictive of the acceptable salt preparation of feed can be shown The improvement meat duck of work and the production performance of laying duck.
In another embodiment, using the fatty acyl group derivative and its raceme of asparatate provided by the invention, Prepared by stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed is the production for improving fish The feed addictive of performance.
In another embodiment, using the fatty acyl group derivative and its raceme of asparatate provided by the invention, Stereoisomer, geometric isomer, tautomer, solvate or the feed addictive of feed acceptable salt preparation are to doting on There is more significant effect in the improvement of object production performance.
It applies and is preparing the fatty acyl group derivative of the asparatate provided by the invention in animal feed additive The acceptable salt of feed is a kind of metal cation salt.
Optionally, the acceptable salt of feed of the fatty acyl group derivative of the asparatate is structure such as formula (I) Shown in asparatate fatty acyl group derivative metal cation salt.
Further, the Y in structure asparatate fatty acyl group derivative as shown in formula (I) and X are selected from C1-C20Alkoxy or OH, but be not simultaneously C1-C20Alkoxy, the metal cation salt are the asparatate fatty acyls The resulting salt for meeting feed addictive preparation or feed preparation and requiring of the OH and metal ion exchanged of radical derivative.
Specifically, the metal ion is selected from monovalent metallic ion, bivalent metal ion or trivalent metal ion.
In some embodiments, the monovalent metallic ion is sodium ion (Na (I)), potassium ion (K (I)) or lithium ion (Li(Ⅰ))。
In some embodiments, the bivalent metal ion is calcium ion Ca (II), magnesium ion Mg (II), copper ion Cu (II), zinc ion Zn (II), ferrous ion Fe (II), manganese ion Mn (II), cobalt ions Co (II) or nickel ion Ni (II).
In one embodiment, it applies in the gold for preparing the asparatate fatty acyl group derivative in animal feed additive Belonging to ion salt is zinc ion salt, and the animal feed additive is that animal uses organic zinc agent to replace as high dose inorganic zinc Object.
In one embodiment, it applies in the gold for preparing the asparatate fatty acyl group derivative in animal feed additive Belonging to ion salt is copper ion salt, and the animal feed additive is that animal uses organic copper to be replaced as animal with high dose Inorganic Copper Change object.
In one embodiment, it applies in the gold for preparing the asparatate fatty acyl group derivative in animal feed additive Belonging to ion salt is iron ion salt, and the animal feed additive is animal ferro element replenishers.
In some embodiments, the trivalent metal ion be aluminium ion Al (III), chromium ion Cr (III) or iron from Sub- Fe (III).
Feeding composition of the present invention.
A kind of fatty acyl group derivative comprising asparatate and its raceme, stereoisomer, geometric isomer, mutually Tautomeric, solvate or the acceptable salt of feed at least one and can feeding auxiliary material feeding composition, described can Feeding auxiliary material is carrier, diluent, adjuvant, solvent or their combination that can be feeding.
Feed of the present invention refers to the product for animal edible through industrialization processing, production.
" composition " of the present invention refers to the chemical combination comprising one or more kinds of compound composition effective component Object collective.
"comprising" of the present invention is open language, both include the present invention bright finger content, but it is not precluded Content in terms of him.
" carrier " of the present invention is to refer to carrying active constituent, improves its dispersibility, and has good chemistry steady Qualitative and adsorptivity can feeding substance, be organic carrier and inorganic carrier.The organic carrier is containing the object more than crude fibre Material, including but not limited to corn flour, maize cob meal, wheat bran, powdered rice hulls, defatted rice bran, system chaff, corn stalk powder, peanut shell powder Deng.The inorganic carrier is minerals, is broadly divided into oxide-based, the system for microelement pre-mix material of calcium salt class and silicon Make, including but not limited to calcium carbonate, silicate, vermiculite, zeolite, sepiolite etc..
" diluent " of the present invention, which refers to, is uniformly distributed in additive raw material in material, by the additive of high concentration Raw material is diluted to the pre-mixing agent of low concentration or the substance of premix, and micro constitutent can be separated from each other, and reduces between active constituent React to each other, to increase the stability of active constituent but not influence the physico-chemical property in relation to substance, be organic diluent and nothing Machine diluent.Organic diluent includes but is not limited to corn flour, degermed maize powder, dextrose (glucose), sucrose, has wheat bran Wheat middling, stir-fry soybean powder, wheat-middlings, corn protein powder etc.；Inorganic diluents include but is not limited to lime stone, biphosphate Calcium, conch meal, kaolin (white bole), salt and sodium sulphate.
The adjuvant is the bonding for making the stickiness of substance inherently induce the wetting agent come, substance bonding is made to get up Agent, the retention agent or anti-for making the tablet of substance entirety split the broken disintegrating agent for many fine particles, reduce intergranular friction power The only antitackiness agent that material sticks together, including but not limited to magnesium stearate, talcum powder, vegetable oil, magnesium laurylsulfate, starch, starch Slurry, water, inorganic salts, dextrin, Icing Sugar etc..
It is solvent needed for " solvent " of the present invention refers to dissolution or dispersing solid, including but not limited to water, ethyl alcohol, sweet Oil etc..
In some embodiments, the feeding composition further include additional animal feed additive and/or Animal feed raw material.
The animal feed additive is nutritional feed additive, general feeds additive or pharmaceutical feed addition Agent.
The nutritional feed additive, which refers to, to be added in mixed feed, balanced feed nutrient, improves feed conversion Rate directly plays animal a small amount of or micro substance of trophism, is amino acid, amino-acid salt and the like, vitamin And biostearin, mineral element and its network (chela) close object, micro-organism enzyme preparation or nonprotein nitrogen.
The general feeds additive is also non-nutritive additive, refers to and is added in feed for improving feed benefit With rate, guarantee that feeding quality and quality, some non-nutritive substances for being conducive to animal health or metabolism, including growth promote Agent, vermifuge, seasoning and phagostimulant, feed adjusting material, feed preparation agent, feed storage agent, probiotics, prebiotics and in Chinese herbal medicine additive agent.
Further specifically, the non-nutritive additive is growth promoter, including but not limited to butyric acid, butyric acid Calcium, sodium butyrate, tannic acid, p-Thymol, p-Thymol ester, p-Thymol salt, 2 hydroxybenzoic acid, β-acid, β-acid Ester, β-hydrochlorate, hexahydro β-acid, hexahydro β-acid esters, hexahydro β-hydrochlorate, benzoic acid or calcium benzoate, zinc oxide, zinc sulfate, chlorination Zinc.
In one embodiment, the non-nutritive additive is calcium butyrate.
In another embodiment, the non-nutritive additive is tannic acid.
Specifically, the medicated feed additive includes but is not limited to have prevention Animal diseases, promote growth of animal It acts on and the veterinary drug premixing substance for using and mixing carrier or diluent can be added for a long time in feed.
Further specifically, the medicated feed additive is feeding antibiotic, and the feeding antibiotic includes But be not limited to polymyxins, salinomycin, avilamycin, bacitracin, virginiamycin, Nosiheptide, flavomycoin, grace draw it is mould Element, Kitasamycin, olaquindox, terramycin or aureomycin.
In some embodiments, the fatty acyl group derivative comprising asparatate and its raceme, stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed composition, also comprising nutritional feed additive, One of general feeds additive and medicated feed additive are a variety of.
In some embodiments, the animal feed raw material is cereal and its converted products, oil seeds and its processing Product, legume seed and its converted products, stem tuber, root tuber and its converted products, other seeds, fruit class product and its add Chemical product, forage grass, roughage and its converted products, other plants, algae and its converted products, dairy products and its byproduct, land Raw animal product and its byproduct, fish, other aquatiles and its byproduct, minerals, microbial fermentation product and byproduct, The feeding substance such as other feedstuffs.
The purposes of feeding composition.
The present invention relates to above-mentioned comprising asparatate fatty acyl group derivative and its raceme, stereoisomer, geometry Isomers, tautomer, solvate or the acceptable salt of feed feeding composition application.
In some embodiments, it is described comprising asparatate fatty acyl group derivative and its raceme, stereoisomer, Geometric isomer, tautomer, solvate or the acceptable salt of feed feeding composition be applied to prepare animal feed In additive.
Include asparatate fatty acyl group derivative and its raceme, stereoisomer, geometrical isomerism using described The animal feed additive of the feeding composition preparation of body, tautomer, solvate or the acceptable salt of feed is domestic animal Feed addictive, livestock fodder additives, aquiculture animal feed addictive or feed for pet additive.
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare domestic animal feed additive, institute The domestic animal stated includes but is not limited to pig, ox, sheep, horse, rabbit, ermine of each growth phase etc..
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare livestock fodder additives, institute The poultry stated includes but is not limited to chicken, duck, goose, dove of each growth phase etc..
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare aquiculture animal feed Additive, the aquiculture animal include but is not limited to each growth phase fish, shrimp, crab, soft-shelled turtle, eel etc..
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare feed for pet additive, institute The pet stated includes but is not limited to the dog or cat of artificial feeding.
In some embodiments, with described comprising asparatate fatty acyl group derivative and its raceme, it is three-dimensional different The animal feed addition of the composition preparation of structure body, geometric isomer, tautomer, solvate or the acceptable salt of feed Agent is pre-mixing agent, compound premixing agent, aqua or granule.
In some embodiments, described includes asparatate fatty acyl group derivative and its raceme, alloisomerism Body, geometric isomer, tautomer, solvate or the acceptable salt of feed feeding composition be applied to preparation animal and raise In material.
Include asparatate fatty acyl group derivative and its raceme, stereoisomer, geometrical isomerism using described The animal feed of the feeding composition preparation of body, tautomer, solvate or the acceptable salt of feed is feed stripped, family Fowl feed, aquiculture animal feed or feed for pet.
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare feed stripped, the family Poultry includes but is not limited to pig, ox, sheep, horse, rabbit, the ermine etc. of each growth phase.
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare poultry feed, the family Fowl includes but is not limited to chicken, duck, goose, dove of each growth phase etc..
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare aquiculture animal feed, The aquiculture animal includes but is not limited to each growth phase fish, shrimp, crab, soft-shelled turtle, eel etc..
Specifically, using described comprising asparatate fatty acyl group derivative and its raceme, it is stereoisomer, several What isomers, tautomer, solvate or the acceptable salt of feed feeding composition prepare feed for pet, described dotes on Object includes but is not limited to the dog or cat of artificial feeding.
In some embodiments, comprising asparatate fatty acyl group derivative and its raceme, stereoisomer, several The feed of the feeding composition preparation of what isomers, tautomer, solvate or the acceptable salt of feed be single feed, Concentrated feed, mixed feed, compound premix or concentrate supplement.
Specifically, the mixed feed is perfect compound feed.
Improve the method for cultivated animals production performance.
In some cultivation embodiments, raiser will comprising asparatate fatty acyl group derivative and its raceme, Feed addictive and the feed companion of stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed Clothes give animal edible, improve the production performance of animal with can dramatically.
In some embodiments, the feed addictive is pre-mixing agent, compound premixing agent, granule or aqua, and dynamic Animal edible after object feed mixes.
The animal is domestic animal, poultry, aquiculture animal or pet.
Specifically, the domestic animal includes but is not limited to pig, ox, sheep, horse, rabbit, ermine of each growth phase etc.；Described Poultry includes but is not limited to chicken, duck, goose, dove of each growth phase etc.；The aquiculture animal is including but not limited to each A growth phase fish, shrimp, crab, soft-shelled turtle, eel etc.；The pet includes but is not limited to the dog or cat of artificial feeding.
In one embodiment, raiser will include asparatate fatty acyl group derivative and its raceme, alloisomerism Body, geometric isomer, tautomer, solvate or the acceptable salt of feed feed addictive and feed given with clothes it is disconnected Milk pig feed is used, and is significantly improved the rate of body weight gain of the average daily gain of wean pig and is improved food conversion ratio.
In one embodiment, the day that the feed addictive for giving wean pig feed with clothes with feed is included by raiser L-aminobutanedioic acid fatty acyl group derivative is N- butyryl-ASPARTIC ACID zinc salt, improves the feed intake of wean pig and averagely increases day by day Feed conversion rate is weighed and effectively improves, the feed addictive, which reaches high dose inorganic zinc, improves water to wean pig production performance It is flat.
In another embodiment, the feed addictive for giving wean pig feed with clothes with feed is included by raiser Asparatate fatty acyl group derivative is N- butyryl-ASPARTIC ACID mantoquita, significantly improves the average daily gain of wean pig And feed conversion rate is effectively improved, it is horizontal to wean pig production performance improvement that the feed addictive reaches high dose Inorganic Copper.
In one embodiment, raiser will include asparatate fatty acyl group derivative and its raceme, alloisomerism Body, geometric isomer, tautomer, solvate or the acceptable salt of feed feed addictive and feed give meat with clothes Chicken feed is used, and is significantly improved the weight gain of broiler chicken and is effectively improved the conversion ratio of feed.
In one embodiment, raiser will include asparatate fatty acyl group derivative and its raceme, alloisomerism Body, geometric isomer, tautomer, solvate or the acceptable salt of feed feed addictive and feed give fish with clothes It is edible.
In one embodiment, raiser will include asparatate fatty acyl group derivative and its raceme, alloisomerism Body, geometric isomer, tautomer, solvate or the acceptable salt of feed feed addictive and feed give children with clothes Dog food is used.
In other feeding embodiments, raiser will comprising asparatate fatty acyl group derivative and its raceme, Stereoisomer, geometric isomer, tautomer, solvate or the acceptable salt of feed feeding composition give animal It is edible, improve the production performance of animal with can dramatically.
Optionally, the feeding composition is feed addictive pre-mixing agent, feed addictive compound premixing agent, granule Or aqua, animal edible is given with clothes with feed.
In one embodiment, the feeding composition is feed addictive pre-mixing agent.
In one embodiment, the feeding composition is feed addictive compound premixing agent.
Optionally, the feeding composition is concentrated feed, mixed feed, compound premix or concentrate supplement, directly It connects and gives animal edible as animal diet.
In one embodiment, the feeding composition is perfect compound feed.
Certain embodiments of the present invention will now be described in more detail, the example is said by the structural formula and chemical formula being appended It is bright.The intent of the present invention covers all substitutions, modification and equivalent technical solution, they are included in claim such as and define The scope of the present invention in.In addition, certain technical characteristics of the invention be it is clearly visible, divide in a number of independent embodiments It is not described, but can also provide or be provided in the form of any suitable sub-portfolio in combination in a single embodiment.
Specific embodiment:
In order to make the objectives, technical solutions, and advantages of the present invention clearer, by the following examples to the present invention Compound, composition and application be described in further detail.It should be appreciated that specific embodiment described herein is only used In explaining the present invention, it is not intended to limit the present invention.
The preparation of A compound
Below only with N- butyryl-ASPARTIC ACID, N- butyryl-ASPARTIC ACID ethyl ester and its a kind of preparation of salt The preparation method of the fatty acyl group derivative of asparatate is described in detail for journey, the rouge of other asparatates Fat acyl derivative can be prepared as reference.
The preparation of embodiment A1 N- butyryl-ASPARTIC ACID
100.0g (0.75mol, 1eq) ASPARTIC ACID is dissolved in 400mL at room temperature and contains sodium hydroxide 60.2g In the water of (1.50mol, 1.5eq), 106.4g (0.67mol, 0.89eq) butyric anhydride is slowly dropped into, instead by stirring and dissolving clarification With 6mol/L sodium hydrate aqueous solution control reaction solution pH8 or so during answering, it is stirred at room temperature for 24 hours.After reaction, concentrated hydrochloric acid is used Reaction solution pH to 2 is adjusted, ethyl acetate extracts (600mL × 2), is concentrated to get after ethyl acetate layer merges, anhydrous sodium sulfate is dry Crude product is grease.Crude product recrystallizes through petroleum ether and white solid is precipitated, and filters, is dried to obtain white solid product 100g (0.49mol), yield 65.3%.
1HNMR(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).
The preparation of embodiment A2 N- butyryl-ASPARTIC ACID iron
22.2g (0.08mol, 0.67eq) Iron(III) chloride hexahydrate is dissolved in 100mL water at room temperature, by 25g under stirring (0.12mol, 1eq) N- butyryl-ASPARTIC ACID is dissolved in the water that 100mL contains sodium hydroxide 9.85g (1.50mol, 1.5eq) Be slowly dropped into reaction system after solution, have rust solid generation, continue to filter after being stirred to react 5.0h, filter cake through washing, Rust solid 27g (0.086mol), yield 71.7% are obtained after drying.
The preparation of the double ethyl esters of embodiment A3 N- butyryl-ASPARTIC ACID
The synthesis of the double carbethoxy hydrochlorides of step 1:L- asparatate
320mL (5.48mol, 40eq.) dehydrated alcohol is added into 1000mL single port bottle, is cooled to -10 degree, drips thereto Add 28mL (378.92mmol, 2.8eq.) SOCl2, control rate of addition control solution temperature is in -10 degree left and right, after being added dropwise In -10 degree stirring 1 hour, then 18.16g (136.48mmol, 1eq.) ASPARTIC ACID is added thereto, and stir at room temperature It mixes 2 hours, subsequent 80 DEG C of reactions, the detection reaction of TLC plate, decompression is spin-dried for solvent after completion of the reaction, and a small amount of dehydrated alcohol is added It is repeated several times, in refrigerator cool overnight, solid is precipitated, solid re-crystallizing in ethyl acetate filters, is dried to obtain white solid 18.08g yield 58.70%.ESI[M-Cl]+190,1HNMR(500MHz,D2O)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: the synthesis of the double ethyl esters of butyryl ASPARTIC ACID
The double carbethoxy hydrochlorides of 23.92g (106.00mmol, 1eq.) ASPARTIC ACID are weighed in 500mL single port bottle, are added Enter 150mL DCM dissolution, add 26.93g (266.13mmol, 2.5eq.) triethylamine, be cooled to 0 degree, is then added dropwise 17.07g (160.21mmol, 1.5eq.) butyl chloride is dissolved in the solution of 50mL DCM, and temperature is on 0 degree of left side when butyl chloride is added dropwise in control The right side after being added dropwise, stirs 1 hour in 0 degree, is then warmed to room temperature reaction 2 hours, stops reaction.To reaction system 100mL Water separates organic phase, and water phase is extracted 2 times with DCM, merges organic phase, and organic phase is washed with water, saturated common salt washing, anhydrous slufuric acid Sodium is dry, is concentrated under reduced pressure to give colourless liquid 12.47g, yield 45.36%.ESI[M+H]+260,1HNMR(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).
The stability study of embodiment B asparatate fatty acyl group derivative is tested
Investigating the pre-mixing agent that asparatate fatty acyl group derivative and its mass fraction are 5%, (hereinafter referred to as 5% is pre- Mixture) its Contents of Main Components changes with time situation under 60 DEG C of stability conditions respectively.
Laboratory apparatus includes medicine stability incubator, Waters high performance liquid chromatograph (HPLC) etc..
Experiment reagent includes asparatate fatty acyl group as shown in Table 1 derivative raw material (standard items), methanol (chromatography Grade), phosphoric acid (analysis pure).
The preparation of standard solution: accurately weighing 100mg asparatate fatty acyl group derivative standard items, and 25mL water is added Working stock liquid is made in ultrasonic dissolution.Take appropriate working stock liquid, be diluted to respectively with water concentration be 500ppm, 1000ppm, The working solution of 2000ppm, 4000ppm, HPLC are to be measured.Whether sample survey concentration is linear with HPLC peak area response, does Standard curve.If the preparation method that asparatate fatty acyl group derivative is the standard solution of metal cation salt is to accurately weigh 50mg standard items are added 25mL5% hydrochloric acid solution ultrasonic dissolution 30min until being completely dissolved, working stock liquid are made.It takes appropriate Working stock liquid is diluted to the work that concentration is 250ppm, 500ppm, 1000ppm, 2000ppm with 5% hydrochloric acid solution respectively Liquid, HPLC is to be measured, and whether sample survey concentration is linear with HPLC peak area response, does standard curve.
The preparation of test solution: raw material, 5% premix of suitable asparatate fatty acyl group derivative are accurately weighed Suitable quantity of water ultrasonic dissolution is added in agent and 5% feed, is made into 4000ppm solution, and HPLC analysis is carried out after 0.22 μm of membrane filtration. If asparatate fatty acyl group derivative is that metal cation salt accurately weighs suitable asparatate fatty acyl group derivative 5% hydrochloric acid solution 25mL ultrasonic dissolution 30min is added until being completely dissolved, 2000ppm solution is made into, through 0.22 μm of membrane filtration HPLC analysis is carried out afterwards.
HPLC testing conditions: chromatographic column: waters C18 column (250mm*4.6mm, 5 μm) column.Mobile phase: 0.02% phosphorus Acid: methanol；(gradient elution: methanol: 5% → 40% (0-25min) curve 6,40% → 80% (25-30min) curve 6,80% Methanol (31min) curve 6,80% → 5% (31-32min) curve 1,5% methanol (32-37min) curve 1, total time 37min； Detection wavelength: 210nm；Column temperature: 25 DEG C；Sample volume: 20 μ L；Flow velocity: 1ml/min.
Test method: 60 DEG C of stability tests: the derivative raw material of asparatate fatty acyl group and its 5% pre-mixing agent sample It being placed in culture dish, booth is placed at 60 DEG C at the thin layer of≤5mm, in the 5th day, the progress HPLC detection of sampling in 10 days, every kind Sample samples three times in parallel.
Test result: test result indicates with " average value ", as shown in table 1.In terms of test result, asparatate fat Acyl derivative either raw material still has good stability content equal 60 DEG C of high fevers in pre-mixing agent during test There is no significantly changing.
The factors affecting stability of 1 asparatate fatty acyl group derivative of table is studied
B culture experiment
The influence of embodiment B1 asparatate fatty acyl group derivative and its salt to Production Performance of Weaning Pigs
Select the weight of clinical examination health close from 100 nest, 28 ± 2 age in days " Ternary Pig " three way cross weanling pig 390 be test pig, be randomly divided into 13 groups, every group of 3 repetitions are each to repeat male and female fifty-fifty totally 10.Piglet opens from 7 ages in days Beginning food calling, 28 ages in days wean pig house is concrete floor, reinforcing bar fence, well-ventilated, proper temperature.To pigsty and utensil before test It carries out disinfection.Experimental period, test pig subfield stable breeding under the same feeding and management condition of same pigsty are freely eaten and drink water；Pig House cleans once daily, and flushing ground is primary every three days, keeps clean sanitary condition；Day feeding 3 times.Each test group is divided into pair According to group and test group.I group is control group, and piglet feeds basal diet；Based on the daily ration of II~VIII group of piglet of test group feeding The fatty acyl group derivative of the asparatate of 45ppm is added on the basis of daily ration respectively, as shown in table 2；IV~VIII group of piglet is raised The daily ration fed is the N- butyryl-ASPARTIC ACID metal cation salt for adding 1000ppm on the basis of basic daily ration respectively, such as table 2 It is shown.Entire each test group of breeding process does not add other antioxidant contents and growth accelerator additionally, and experimental period is 40 days.Test Phase observes piglet feeding daily and health status simultaneously weighs remaining daily ration, records feed consumption, and upper at 0 and 40 day Noon 7:00~9:00 weighs to test pig, calculates average daily gain (ADFI, g/d* are only), average daily gain (ADG, g/d* are only) With feedstuff-meat ratio (FCR).Calculation formula is as follows:
Average daily gain=(ingredient total amount-remains doses)/(test number of days × every repetition pig number)；
Average daily gain=(testing last average weight-test just average weight)/test number of days；
Feedstuff-meat ratio=average daily gain/average daily gain.
Test data is for statistical analysis using SPSS18 software, first makees one-way analysis of variance (ANOVA) to data, if Significant difference between processing, then Multiple range test, significance 0.05 are carried out with Duncan's method.Test result is with " average value ± standard error " indicates that test result is as shown in table 2.
From the feeding experiment result of weanling pig it is found that each group is disconnected compared with blank control group in terms of average daily gain The feed intake of milk piglet is improved, wherein N- caprinoyl-ASPARTIC ACID and N- butyryl-ASPARTIC ACID zinc salt effect Highly significant；About average daily gain, the effect that the average daily gain of each group wean pig is improved compared with blank control group, Wherein give N- caprinoyl-ASPARTIC ACID, N- butyryl-ASPARTIC ACID diethylester and N- butyryl-ASPARTIC ACID Sodium salt, zinc salt, the test group effect of molysite and calcium salt it is more significant；In terms of feedstuff-meat ratio, respectively test compared with the control group Effect does not occur significant change, but fall is 5%~7%.
The fatty acyl group derivative and its salt of 2 asparatate of table influence research to the production performance of weanling pig
Influence of the embodiment B2 asparatate fatty acyl group derivative to performance in layers
Test uses single-factor Random Design, selects similar in 147 ages in days, weight parts in Beijing opera spoken in Beijing dialect laying hen 480, is randomly divided into 8 A processing group, every group of 3 repetitions, male and female is fifty-fifty, 20 parts in Beijing opera spoken in Beijing dialect laying hens of each repetition.Disappear before test to henhouse and utensil Poison.Experimental period, carries out cage under the same feeding and management condition of same henhouse.Basal diet is entire to raise based on Corn-soybean Feeding process does not add other antioxidant contents and growth accelerator additionally.Each test group is respectively to test I~VIII group.Wherein test I Basal diet is only given for control group, the different asparatates of 500ppm are added in test II~VIII respectively in basal diet Fatty acyl group derivative, grouping are shown in Table 3.Pre-feeding period 10 days, experimental period 158 days, test chicken free water and feeding, day feeding 2 It is secondary.During test, egg number, egg production, feed intake are recorded as unit of repetition daily, calculates the laying rate of test full period laying hen (EPR), average daily gain (ADFI, g/d), egg size (EW, g) and feedstuff-egg ratio (FER).Calculation formula is as follows:
Laying rate (%)=average day total egg number/chicken number × 100；
Egg size (g)=average day total egg size/average day total egg number；
Feedstuff-egg ratio=average daily gain/egg size.
Test data is for statistical analysis using SPSS18 software, first makees one-way analysis of variance (ANOVA) to data, if Significant difference between processing, then Multiple range test, significance 0.05 are carried out with Duncan's method.Test result is with " average value ± standard error " indicates that test result is as shown in table 3.
As can be known from the results, improvement is not compared with the control group for influence of the test sample to the laying rate of test chicken and feedstuff-egg ratio Different degrees of improvement significantly but is embodied, laying rate improves 1.9%-5.5%, and feedstuff-egg ratio declines 2.3%- 6.4%；Test sample is to the feed intake of test chicken and the influence of egg size without influence.
Application effect research of the 3 asparatate fatty acyl group derivative of table in laying hen material
Influence of the fatty acyl group derivative of embodiment B3 asparatate to meat chicken production performance
Test uses single-factor Random Design, selects average weight similar in 1 age in days, weight for three yellow-feather broilers of 50g 480,8 processing groups are randomly divided into, every group of 3 repetitions, male and female is fifty-fifty, 20 three yellow-feather broilers of each repetition.It is right before test Henhouse and utensil carry out disinfection.Experimental period, carries out cage under the same feeding and management condition of same henhouse.Basal diet is with corn- Based on dregs of beans, entire breeding process does not add other antioxidant contents and growth accelerator additionally.The respectively test I of each test group~ VIII group.Wherein test I only gives basal diet for control group, and test II~VIII adds 300ppm not in basal diet respectively Same asparatate fatty acyl group derivative, grouping are shown in Table 4.Experimental period totally 20 days, test chicken free water and feeding, day fed Material 2 times.As unit of each repetition, (stops expecting 12h, not cut off the water) in the weighing of 21 ages in days, statistical test chicken feed consumption rate calculates each group Average daily gain (ADFI, g/d* are only), average daily gain (ADG, g/d* are only) and the feedstuff-meat ratio (FCR) of test chicken, calculate public Formula is as follows:
Feedstuff-meat ratio (FCR)=average daily gain/average daily gain.
Test data is for statistical analysis using SPSS18 software, first makees one-way analysis of variance (ANOVA) to data, if Significant difference between processing, then Multiple range test, significance 0.05 are carried out with Duncan's method.Test result is with " average value ± standard error " indicates that test result is as shown in table 4.
As can be known from the results, it is right during test in broiler breeding to test the asparatate fatty acyl group derivative being related to The feed intake and feedstuff-meat ratio of broiler chicken do not have significant impact, but have different degrees of improvement to the feedstuff-meat ratio of broiler chicken； In addition test sample is more significant to the weight gain improvement effect of broiler chicken, it can be seen that, the fatty acyl group derivative pair of asparatate The production performance of broiler chicken has more significant improvement on the whole.
Application effect research of the fatty acyl group derivative of 4 asparatate of table in broiler chicken material
Application of the fatty acyl group derivative of embodiment B4 asparatate in fish material
1) test material
Fish is used in test: test fish used be the bouncing of current year, the consistent Grass carp of specification in large cage (4 × 2 × 1.5m3) formal culture experiment is just used for after raising 4 weeks, experimental system is buoyancy small-sized net cage (1.1 × 1.1 × 1.1m of specification3), often A small-sized net cage is equipped with a pneumatic head, inflates for 24 hours daily.Small-sized net cage and temporary feeding net cage are placed in one, test site 3500m2's In pond, the pond depth of water about 1.5m, pond water is water under being sufficiently aerated.When test, hungry 1 day grass carp 640 is trailed into machine It is divided into 8 groups, every group sets 4 repetitions, and 20 tail fishes are put in each repetition, it is put into 32 net cages after being weighed as unit of each repetition, The test feed of the different test samples of feeding addition same amount respectively.
Test feed: test with feed by table 5 formula voluntarily prepare, different tests group by table 6 feed respectively add it is identical The different test samples of content.Partial size 3mm buoyancy is made by Jiangsu shepherd extruding unit after pulverizing in feeds utilized raw material Expanded pellet diet, 130 DEG C of mold clearing temperature, by spraying 3% soya-bean oil outside fuel injection equipment, shady place is sealed spare.
5 test of table feed of grass carp formula and chemical component (%wt.)
Grouping is tested in application study of the 6 asparatate fatty acyl group derivative of table in fish material
Group Test sample Dosage (ppm)
I group - -
II group N- acetyl-ASPARTIC ACID 3000
III group N- butyryl-ASPARTIC ACID 3000
IV group N- caprinoyl-ASPARTIC ACID 3000
V group N- lauroyl-ASPARTIC ACID 3000
VI group N- myristoyl-ASPARTIC ACID 3000
VII group N- stearoyl-ASPARTIC ACID 3000
VIII group N- butyryl-ASPARTIC ACID diethylester 3000
(2) test method
Trial: test uses artificial limit food to feed, and feeding amount adjusts weekly once, and every group feeds horizontal (press initial Weight) it is completely the same, (7:30 and 15:00) twice is fed daily, and always feeding appetite is that 580g/ repeats test group.Test by a definite date 8 Week.Timing is monitored water quality during test, cultivates whole 26.88 ± 3.08 DEG C of water temperature, DO > 5.0mg O L-1、pH 7.8、 Ammonia nitrogen < 0.50mg N L-1, nitrite nitrogen < 0.05mg N L-1。
Parametric statistics: when test, stopping carrying out whole weighing to each net cage fish after feeding 1d, calculate its rate of body weight gain (WG, %), and Feed coefficient (FCR).Calculation formula is as follows:
Rate of body weight gain (WG, %)=100 × (average end weight-average initial weight)/average initial weight；
Feed coefficient (FCR)=food ration/weight gain.
(3) test result
The test result shown in the table 7 it is found that the culture experiment Mid-Heaven Gate aspartic acid in grass carp fatty acyl group derivative The rate of body weight gain of grass carp can significantly be improved and reduce the feed coefficient still feed system other than N- myristoyl-asparatate Number decline effect is not significant.
Application test result of the fatty acyl group derivative of 7 asparatate of table in aquatic products material
The embodiments described above only express several embodiments of the present invention, is used to implement this hair there are also other modes It is bright.Correspondingly, the embodiment of the present invention is illustratively to be illustrated, and but it cannot be understood as to of the invention special The limitation of sharp range, it is also possible to made modification or in the claims within the scope of the present invention and in same inventive concept Added equivalent.

Claims (14)

1. a kind of structure asparatate fatty acyl group derivative or its raceme as shown in following general formula, stereoisomer, Geometric isomer, tautomer, solvate or the acceptable salt of its feed are preparing answering in animal feed additive With:
Wherein, Y and X are respectively and independently selected from C1-C20Alkoxy or OH；R1For R1aC (=O), R1aS (=O)2Or H；R2For R2aC (= ) or R O2aS (=O)2；The R1aAnd R2aIt is respectively and independently selected from C1-C20Alkyl or C3-C7Naphthenic base.
2. application according to claim 1, which is characterized in that the R1For H.
3. application according to claim 1, which is characterized in that the R2For R2aC (=O), R2aSelected from C1-C20Alkyl or C3-C7Naphthenic base.
4. application according to claim 3, which is characterized in that the R2aSelected from C1-C10Alkyl.
5. application according to claim 1, which is characterized in that the Y and X is OH.
6. application according to claim 1, which is characterized in that the Y and X is respectively and independently selected from C1-C20Alkoxy or OH, and be not simultaneously OH.
7. application according to claim 6, which is characterized in that the Y and X is respectively and independently selected from C1-C10Alkoxy or OH, and be not simultaneously OH.
8. application according to claim 1, which is characterized in that the acceptable salt of the feed is metal cation salt.
9. application according to claim 8, which is characterized in that the metal cation salt be sodium ion salt, calcium ion salts, Zinc ion salt, copper ion salt or iron ion salt.
10. a kind of feeding composition, which is characterized in that include the described in any item asparatate fatty acyls of claim 1-9 Radical derivative or its raceme, stereoisomer, geometric isomer, tautomer, solvate or its feed are acceptable At least one of salt and can feeding auxiliary material.
11. feeding composition according to claim 10, which is characterized in that the feeding composition also includes additional Animal feed additive, the additional animal feed additive is selected from nutritional feed additive, non-nutritive feed adds Add agent or medicated feed additive.
12. feeding composition described in 0 or 11 according to claim 1, which is characterized in that also include animal feed raw material.
13. the described in any item feeding compositions of claim 10-12 are preparing the application in animal feed additive.
14. the described in any item feeding compositions of claim 10-12 are preparing the application in animal feed.
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