CN106588701A - Amino acid derivative and preparation method and application thereof - Google Patents

Amino acid derivative and preparation method and application thereof Download PDF

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Publication number
CN106588701A
CN106588701A CN201611096104.2A CN201611096104A CN106588701A CN 106588701 A CN106588701 A CN 106588701A CN 201611096104 A CN201611096104 A CN 201611096104A CN 106588701 A CN106588701 A CN 106588701A
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Prior art keywords
fatty
acid
salt
acylamino
amino acid
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史鲁秋
苏桂珍
孔惠
胡海霞
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Nanjing Huashi New Material Co Ltd
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Nanjing Huashi New Material Co Ltd
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Priority to CN201611096104.2A priority Critical patent/CN106588701A/en
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
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    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
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    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
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    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Abstract

The invention provides salts formed from fatty acyl amino acid esters and fatty acyl amino acids and a forming method of the salts that have inhibitory or killing effect for microorganisms. These derivatives also have the properties such as high performance, mildness, and broad-spectrum baceriostasis, and are widely applicable to the products, such as foods, drinks, feeds, home care products, and personal care products. The salts formed from fatty acyl amino acid esters and fatty acyl amino acids according to the invention are liquids that are convenient to add and use, and the salts have good inhibitory effect for common microorganisms, may replace traditional preservatives, and have the advantages of high safety, low irritation, reduced allergy and toxicity risk, low degrading difficulty, good environmental friendliness and the like.

Description

A kind of amino acid derivativges, preparation method and applications
Technical field
The present invention relates to a kind of amino acid derivativges, preparation method, and the derivative is used as microbial inhibitor, in food Application in product, feed, household care and personal care articles.
Background technology
Preservative is used in food, feed, cosmetics and furniture nursing product, and Main Function is the growth for suppressing microorganism And breeding, to extend the holding time of product, suppress product putrid and deteriorated.With developing rapidly for the industries such as cosmetics, food, Safe and efficient protective system is selected, is the problem that current policies and regulations, consumer and research worker pay special attention to.
Many traditional preservatives are all proven to have certain negative effect, and such as DMDMH meeting release formaldehydes, Kathon CG series contains Chlorine has stimulation to some skin quality, and Bronopol may generate Carcinogenic Nitrosamines, and IPBC may cause to take in iodine, trichlorine Newly there is negative effect to environment.And parabens, its phenyl ring may accumulate or in specific test system in adipose tissue The ability of certain simulation female sex hormone estrogen is shown in system.
Regulation is also increasingly stricter for the operating specification of preservative, different plug azoles Lin ketones, Form aldehyde release body, oxybenzene esters The use of preservative is restricted increasingly.Increasingly stricter cosmetics regulation, the raising of the awareness of safety of consumer and right The factors such as mistaken ideas, the safety that preservative understands, this series of change promotes the use total amount of traditional preservatives substantially to glide, urgently Treat new preservative exploitation and application.
Lauroyl arginine ethyl ester hydrochloride is a class security, the extraordinary preservative of effect, be applied to the product of suffering from indigestion, The anti-corrosion of cosmetics；Used by the food and agricultural organization/combination food additive Committee of Experts of World Health Organization (JECFA) approval；In addition, Lauroyl arginine ethyl ester hydrochloride also is compliant with the correlation of the countries and regions such as European Union, Australia, Canada and New Zealand Regulation.
Lauroyl arginine ethyl ester hydrochloride is a kind of white powder, is unfavorable for being added in formula, and fusing point is in 50-58 DEG C, when adding in formula, after needing to dissolve by solid heating and melting or using solvent in advance, in being then added to formula system, make Its addition is bothered very much, even if in addition, from solvent dissolving, its solubility is also very limited, as only maximum molten in its glycerine Solution only 20% or so.
The present invention provides a kind of arginine ethyl ester derivative, and such product fusing point is low, and normal temperature is the liquid of clear, can To be easily dissolved in the common solvents such as glycerine, solubility is up to 70%, can very easily be used for food, medicine and Cosmetics.
The content of the invention
It is an object of the invention to provide the salt that a kind of fatty acylamino-acid ester and fatty amic acid are formed, such derives Thing is liquid form, has to microorganism and preferably suppresses or killing effect, can facilitate be widely used in food, beverage, In the products such as medicine, household care and personal nursing.
The salt that fatty amic acid provided by the present invention and fatty acylamino-acid ester are formed, has to common microorganism There is good inhibiting effect, traditional preservative can be substituted.
The compound of the present invention has natural origin, high security, low irritant, reduces allergy and risk of toxicity, and With degradable, advantages of environment protection.
The technical scheme that the present invention is provided：A kind of method for utilizing fatty acylamino-acid ester and fatty amic acid into salt, By fatty acylamino-acid ester with fatty amic acid into after salt, fungistatic effect is significantly increased.
The salt that fatty acylamino-acid ester of the present invention and fatty amic acid are formed, microorganism is had suppress or The method of the salt of killing action, concretely comprises the following steps：
（1）Dissolving：Fatty acylamino-acid ester is dissolved in into solvent, 50-55 DEG C of dissolving is heated to；
（2）Into salt：Fatty amic acid is added to step（1）In the fatty acylamino-acid ester solution of gained, clarification is mixed to It is transparent；
（3）By step（2）The salt vacuum distillation that middle compounding is formed, removes solvent.
Step（1）Middle fatty acylamino-acid ester has the chemical constitution of (a) ~ (d), can be in formula (a) ~ (d) The combination of one or more：
I. arginine derivative and its common salt, its general structure such as formula (a)：
(a)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group；
II. ornithine derivative and its common salt, its general structure such as formula (b)：
(b)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group；
III. lysine derivative and its common salt, its general structure such as formula (c)：
(c)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group；
IV. histidine derivative and its common salt, its general structure such as formula (d)：
(d)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group.
Step（1）In solvent be water or ethanol；
Step（2）In fatty amic acid, can be the combination of one or more material, by carbon number for 5-21 fat Acid and amino acid condensation are formed, and wherein amino acid is selected from alanine, arginine, aspartic acid, cysteine, glutamine, paddy Propylhomoserin, histidine, isoleucine, glycine, asparagine, leucine, lysine, methionine, phenylalanine, proline, Serine, threonine, tryptophan, tyrosine, valine.
The antibacterial system of the salt formed to fatty acylamino-acid ester of the present invention and fatty amic acid is estimated Test.
1. preservation challenge test：Fatty acylamino-acid ester and fatty amic acid are compounded the salt system to be formed and be added to shield In skin product formula, by EU criteria BP2002 XVIC preservative efficacy testings method respectively to the formula solution of the different salt of addition Carry out preservation challenge test.
2. minimal inhibitory concentration test：Compound for fatty acylamino-acid ester and fatty amic acid the salt system to be formed and Lauroyl arginine ethyl ester carries out preservative efficacy testing.Preservative efficacy testing bacterial classification is shown in Table 1：
3. patch test：The salt system and lauroyl arginine to be formed are compounded for fatty acylamino-acid ester and fatty amic acid Ethyl ester carries out skin hypersensitivity test.
The salt system that compounding of the present invention is formed has good compatibility with general cosmetic material, with surface The compatibility of the other components such as activating agent, grease, solvent, antioxidant very well, is mixed after emulsification with cosmetic material, can be made The matrix such as cream, frost, breast are fine and smooth uniform, and long-term storage is not stratified, impermeable, stable dosage forms.
Specific embodiment by the following examples is described in further detail again to the above of the present invention, but It is not limited only to below example.The present invention is included under above-mentioned technological thought, according to ordinary skill knowledge and strong hand Various replacements or change that section is made, all should be included within the scope of the invention.
Specific embodiment
For the essence for being better understood from inventing, the content of the invention, but present invention are described in detail below by example It is not limited thereto.Fatty amic acid used, fatty acylamino-acid ester are self-control in following embodiment.
Embodiment 1
（1）Weigh lauroyl arginine ethyl ester 76.9g（0.2mol）, add 30mL ethanol, 60 DEG C of heating water bath dissolvings；
（2）0.1mol lauroyl glutamates are added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom lauroyl arginine ethyl ester lauroyl glutamate be yellow liquid, 14 DEG C of freezing point.
Embodiment 2
（1）0.1mol cocounut oil acyl lysine propyl ester is weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol lauroyl glycine is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom cocounut oil acyl lysine propyl ester lauroyl glycinate is yellow liquid, and freezing point is 18 DEG C.
Embodiment 3
（1）0.1mol lauroyl ornithine ethyl esters are weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol Hamposyl Ls are added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom lauroyl ornithine ethyl ester Hamposyl L salt be yellow transparent liquid, 13 DEG C of fusing point.
Embodiment 4
（1）0.2mol lauroyl histidine ethyl esters are weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol lauroyl aspartic acid is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom lauroyl histidine ethyl ester lauroyl aspartate is yellow liquid, and freezing point is 10 DEG C.
Embodiment 5
（1）0.1mol cocounut oil acyl arginine butyl esters are weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol palmityls proline is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom cocounut oil acyl arginine butyl ester palmityl proline salt is colourless liquid, and freezing point is 11 DEG C.
Embodiment 6
（1）0.1mol palmitoyllysines methyl esters is weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol octyl group acyls tyrosine is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom palmitoyllysines methyl esters octyl group acyl tyrosine salt is weak yellow liquid, and freezing point is 16 DEG C.
Embodiment 7
（1）0.1mol octadecyl acyl histidine butyl esters are weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol decyl acyls alanine is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom octadecyl acyl histidine butyl ester decyl acyl alanine salt is colourless transparent liquid, and freezing point is 15 DEG C.
Embodiment 8
（1）0.1mol hexyl acyl ornithine propyl ester is weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol lauroyl valine is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom hexyl acyl ornithine propyl ester lauroyl valine salt is colourless transparent liquid, and freezing point is 18 DEG C.
Embodiment 9
（1）0.1mol eicosyl acyl arginine methyl esters are weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol cocounut oil acyls leucine is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom eicosyl acyl arginine methyl esters cocounut oil acyl leucine salt is yellow liquid, and freezing point is 12 DEG C.
Embodiment 10
（1）0.1mol cetyl acyl histidine ethyl esters are weighed, 30mL ethanol, 60 DEG C of heating water bath dissolvings are added；
（2）0.1mol docosyl acyls serine is added（1）In, it is uniformly mixed, obtain salt system；
（3）Will（2）In the system vacuum distillation that obtains, remove ethanol；
（4）Products obtained therefrom cetyl acyl histidine ethyl ester docosyl acyl serine salt is yellow clear liquid, is coagulated 12 DEG C of solid point.
The salt system sample code name of fatty acylamino-acid ester, fatty amic acid and gained corresponding to embodiment 1-10 is shown in Table 2：
Embodiment 11
Above-mentioned antibacterial salt system is carried out into product formula experiment, formula is shown in Table 3 to table 6.
Embodiment 12
For the antibacterial salt system of embodiment 1-10, preservation challenge experiment is done, carry out screening verification.Through the mushroom culture of 7 days With the antibacterial investigation in 28 day cycle, result judgement is shown in Table 7 to table 10.Bacterium, mould, the test result list of saccharomycete Inhibition test Position is CFU/ml.
Bacteriostatic experiment shows that fatty acylamino-acid ester compounds the salt system to be formed to bacterium, mould, yeast with fatty amic acid The inhibitory action of bacterium is than more significant.
Embodiment 13
Antibacterial salt system and lauroyl arginine ethyl ester in for embodiment 1-10（LAE）Carry out the related microorganism of cosmetics （Escherichia coli, staphylococcus aureus, Pseudomonas aeruginosa, Pseudomonas cepacia, Candida albicans, aspergillus niger, chaff horse traction color Bacterium）Minimal inhibitory concentration（MIC）Value test（Unit：ug/mL）：
Compared with lauroyl arginine ethyl ester hydrochloride, each antibacterial system is all low to the MIC value of different microorganisms, illustrates antibacterial body System is more significantly to the inhibitory action of microorganism.
Embodiment 14
Carry out patch test for embodiment 1-10 gained salt system sample, and with lauroyl arginine ethyl ester hydrochloride（LAE） Compare.Patch test results are shown in Table 12.
Patch test shows, compared to lauroyl arginine ethyl ester hydrochloride, fatty acyl amino acid esters and fatty amic acid Salt system excitant it is less.

Claims (10)

1. the invention provides a kind of fatty acylamino-acid ester and amino acid derivativges obtained by fatty amic acid reaction.
2. according to described in claim 1, using fatty acylamino-acid ester and amino acid derivativges obtained by fatty amic acid, It is characterized in that：
(1) with relatively low freezing point, be intended to than the fusing point of fatty acylamino-acid ester and fatty amic acid it is low, can be very square Just in being added to formula, without the need for heating；
(2) with extraordinary solubility, be soluble in polyalcohol, such as glycerine, ethylene glycol, propane diols, butanediol, pentanediol, oneself Glycol etc.；
(3) Miscibility is good, and the other products with formula system, such as surfactant, emulsifying agent have higher compatibility, Can widely use.
3. according to described in claim 1 using fatty acylamino-acid ester and fat amic acid into salt method, its concrete step Suddenly it is：
(1) dissolve：0.1mol fat acylamino-acid esters are dissolved in into solvent, 50-55 DEG C of dissolving is heated to；
(2) into salt：0.1mol fat amic acids are added to step（1）In the fatty acylamino-acid ester solution of gained, mix To clear；
(3) by step（2）The salt vacuum distillation that middle compounding is formed, removes solvent.
4., according to described in claim 1, compound to be formed to microorganism tool using fatty acylamino-acid ester and fatty amic acid There is the salt of suppression or killing action, it is characterised in that fatty acylamino-acid ester has the chemical constitution of (a) ~ (d), Ke Yiwei The combination of one or more in formula (a) ~ (d)：
I. arginine derivative and its common salt, its general structure such as formula (a)：
(a)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group；
II. ornithine derivative and its common salt, its general structure such as formula (b)：
(b)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group；
III. lysine derivative and its common salt, its general structure such as formula (c)：
(c)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group；
IV. histidine derivative and its common salt, its general structure such as formula (d)：
(d)
Wherein, R1It is methyl, ethyl, propyl group or butyl；R2Be carbon number be 6-22 fatty acyl group.
5., according to described in claim 1, react to be formed to microorganism tool using fatty acylamino-acid ester and fatty amic acid There is the salt of suppression or killing action, it is characterised in that fatty amic acid is by the aliphatic acid and amino acid that carbon number is 5-21 Condensation is formed, and can be the combination of one or more fatty amic acid, and wherein amino acid is selected from alanine, arginine, asparagus fern Propylhomoserin, cysteine, glutamine, glutamic acid, histidine, isoleucine, glycine, asparagine, leucine, lysine, Methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine.
6. according to fatty acylamino-acid ester described in claim 2 and fatty amic acid into salt method, it is characterised in that step Suddenly（1）Middle solvent for use is water or ethanol.
7. the amino acid derivativges described in claim 1-6 are applied to food, beverage as the purposes for suppressing microorganism.
8. the amino acid derivativges described in claim 1-6 are applied to feed as the purposes for suppressing microorganism.
9. the amino acid derivativges described in claim 1-6 are applied to household care products as the purposes for suppressing microorganism.
10. the amino acid derivativges described in claim 1-6 are applied to use in personal care as the purposes for suppressing microorganism Product.
CN201611096104.2A 2016-12-02 2016-12-02 Amino acid derivative and preparation method and application thereof Pending CN106588701A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108815151A (en) * 2017-11-03 2018-11-16 华东师范大学 Purposes of the lauroyl arginine ethyl ester as feed addictive
CN108992437A (en) * 2017-11-03 2018-12-14 华东师范大学 Purposes of the lauroyl arginine ethyl ester as antibacterial agent for animals
CN109984953A (en) * 2019-05-22 2019-07-09 宁波御坊堂生物科技有限公司 A kind of protein peptides take a shower, clean skin gel and preparation method thereof
CN111170883A (en) * 2020-01-06 2020-05-19 岳阳科罗德联合化学工业有限公司 Fatty acyl amino acid polyhydroxy ester compound and preparation method thereof

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10114618A (en) * 1996-10-07 1998-05-06 Noevir Co Ltd Liquid cosmetic
CN101415641A (en) * 2006-03-30 2009-04-22 味之素株式会社 Modified clay mineral
US20090318557A1 (en) * 2003-12-22 2009-12-24 Stockel Richard F Dermatological compositions
CN102167766A (en) * 2011-03-21 2011-08-31 北京化工大学 Vinyl amino acid (ester) polymer and preparation method thereof
US20120328544A1 (en) * 2003-12-22 2012-12-27 Nevada Naturals, Inc. Dermatological Treatment Methods And Formulations
CN103232398A (en) * 2012-04-28 2013-08-07 天津滨江药物研发有限公司 Rosuvastatin amino acid salt as well as preparation method and application thereof
CN103479532A (en) * 2012-06-12 2014-01-01 苏州元素集化学工业有限公司 Surfactant composition and uses thereof
CN103732225A (en) * 2010-03-23 2014-04-16 Gojo工业公司 Antimicrobial compositions

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10114618A (en) * 1996-10-07 1998-05-06 Noevir Co Ltd Liquid cosmetic
US20090318557A1 (en) * 2003-12-22 2009-12-24 Stockel Richard F Dermatological compositions
US20120328544A1 (en) * 2003-12-22 2012-12-27 Nevada Naturals, Inc. Dermatological Treatment Methods And Formulations
CN101415641A (en) * 2006-03-30 2009-04-22 味之素株式会社 Modified clay mineral
CN103732225A (en) * 2010-03-23 2014-04-16 Gojo工业公司 Antimicrobial compositions
CN102167766A (en) * 2011-03-21 2011-08-31 北京化工大学 Vinyl amino acid (ester) polymer and preparation method thereof
CN103232398A (en) * 2012-04-28 2013-08-07 天津滨江药物研发有限公司 Rosuvastatin amino acid salt as well as preparation method and application thereof
CN103479532A (en) * 2012-06-12 2014-01-01 苏州元素集化学工业有限公司 Surfactant composition and uses thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
EMIL C. BURUIANA等: "New polyacrylates with stilbene and (S)-phenylalanine side chains for sensor applications. Synthesis and properties", 《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY 》 *
GEORG ZUNDEL: "PROTON TRANSFER IN AND PROTON POLARIZABILITY OF HYDROGEN BONDS: IR AND THEORETICAL STUDIES REGARDING MECHANISMS IN BIOLOGICAL SYSTEMS", 《JOURNAL OF MOLECULAR STRUCTURE》 *
HIDEHARU MORI等: "Double-Hydrophilic and Amphiphilic Block Copolymers Synthesized by RAFT Polymerization of Monomers Carrying Chiral", 《MACROMOL. CHEM. PHYS.》 *
石莹莹: "N-酰基氨基酸表面活性剂的性能及应用研究进展", 《河南化工》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108815151A (en) * 2017-11-03 2018-11-16 华东师范大学 Purposes of the lauroyl arginine ethyl ester as feed addictive
CN108992437A (en) * 2017-11-03 2018-12-14 华东师范大学 Purposes of the lauroyl arginine ethyl ester as antibacterial agent for animals
CN108992437B (en) * 2017-11-03 2021-10-12 华东师范大学 Use of lauroyl arginine ethyl ester as veterinary antibacterial agent
CN109984953A (en) * 2019-05-22 2019-07-09 宁波御坊堂生物科技有限公司 A kind of protein peptides take a shower, clean skin gel and preparation method thereof
CN109984953B (en) * 2019-05-22 2022-08-19 宁波御坊堂生物科技有限公司 Protein peptide gel for bath and skin cleaning and preparation method thereof
CN111170883A (en) * 2020-01-06 2020-05-19 岳阳科罗德联合化学工业有限公司 Fatty acyl amino acid polyhydroxy ester compound and preparation method thereof

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