CN106565546A - Lauroyl arginine ethyl ester glycol acid salt and preparation method and application thereof - Google Patents
Lauroyl arginine ethyl ester glycol acid salt and preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- 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
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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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- 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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q19/00—Preparations for care of the skin
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Abstract
The invention discloses lauroyl arginine ethyl ester glycol acid salt and a preparation method and application thereof and belongs to the technical field of organic matter synthesis. The melting point of the salt ranges from 85 DEG C to 90 DEG C, and the salt is suitable for dry production and can be used as a bactericide or a wetting agent. The preparation method of the lauroyl arginine ethyl ester glycol acid salt comprises the steps that ethyl lauroyl arginate HCL serves as a raw material and reacts with alkali in a solvent in a neutralization manner to remove HCL, and after the salt generated in the neutralization reaction is separated, the product and glycolic acid are subjected to a salt forming reaction, and the lauroyl arginine ethyl ester glycol acid salt is obtained. The lauroyl arginine ethyl ester glycol acid salt prepared by combining the beneficial effects of the ethyl lauroyl arginate HCL and the beneficial effects of the glycolic acid has the beneficial effects of being high in melting point (the melting point ranges from 85 DEG C to 90 DEG C) and easy to prepare and having a relatively good bactericidal effect and moisturizing effect and the like.
Description
Technical field
The invention belongs to organic synthesis technical field, and in particular to a kind of lauroyl arginine ethyl ester glycol hydrochlorate and its
Preparation method and purposes.
Background technology
Lauroyl arginine ethyl ester hydrochloride（LAE hydrochlorates）It is a kind of new amino acid surfactant, it is in people
In vivo the compound taken in human body diet is hydrolyzed to by chemistry and metabolic pathway, U.S. FDA endorsed nothing within 2005
Objection letter, announces LAE by generally recognized as safe food certification, while United States Department of Agriculture (USDA) also allows LAE to eat in meat product and birdss
Used in product.2007, European EFSA ratified it as a kind of food preservative used in food, 2009, European Union committee member
Can first ratify lauroyl arginine ethyl ester hydrochloride as a kind of preservative used in cosmetics.Canadian health in 2014
Portion represents, plans lauroyl arginine ethyl ester as food preservative.
Lauroyl arginine ethyl ester is also widely used in medicine, cosmetic industry.In cosmetic industry, concentration 0.4% with
Under lauroyl arginine ethyl ester hydrochloride as a kind of preservative used in cosmetics, and in soap, scurf removing shampoo
Lauroyl arginine ethyl ester hydrochloride maximum concentration used in agent and non-spray deodorant is 0.8%；In pharmaceuticals industry, mainly
Purposes in for suppressing product beyond the growing of microorganism.
At low temperature dissolubility is very low for lauroyl arginine ethyl ester hydrochloride, and easily crystallization is separated out, and have impact on its antiseptic effect,
Limit it to use, lauroyl arginine ethyl ester hydrochloride is made microscapsule powder by CN105054220A, substantially increase product
Usability and water solublity of the product in low temperature, more conducively processes, and transports and stores.
Lauroyl arginine ethyl ester typically with other material compounding uses, US7074447B2, US20130136832A1's
Research shows, lauroyl arginine ethyl ester hydrochloride and potassium sorbate, and glyceryl laurate ester is united and applied in varieties of food items, makes up
Product, have not only widened the fungicidal spectrum of LAE, and both have obvious cooperative effect, and LAE consumptions can be reduced, and saving is used into
This, but optimal antibacterial effect is reached in terms of different purposes, both ratios need carefully to be adjusted to a suitable ratio
Example, this obviously has requirements at the higher level for the user of product.
The result of study of US20120225942A1, US20140154940A1 shows, when the anion of LAE is changed into other
Anion, such as citric acid, when lauric acid, its antibiotic property is almost identical with the antibiotic property of its hydrochlorate, but due to its dissolving
Degree is less, thus with more longlasting antibiotic property.
On the other hand, because the fusing point of lauroyl arginine ethyl ester hydrochloride is relatively low, only 50 DEG C or so, this gives birth to product
Dry zone during product comes greatly difficult, thus design one kind has more high-melting-point, while antibacterial activity can be increased, it is best
There can be other effects in the functional amino antibacterial of one, for optimization production difficulty, simplify using for user difficult
Degree has realistic meaning.
The content of the invention
An object of the present invention is to provide a kind of lauroyl arginine ethyl ester glycol hydrochlorate, and the salt has than lauroyl
The bigger fusing point of arginine ethyl ester hydrochloride, it is easy to be dried production；The second object of the present invention there are provided lauroyl essence ammonia
The preparation method of acetoacetic ester glycol hydrochlorate, the method with lauroyl arginine ethyl ester hydrochloride as raw material, the neutralization reaction of Jing alkali and
Product is obtained with glycolic acid salt-forming reaction, process is simple；The third object of the present invention there are provided lauroyl arginine ethyl ester
The purposes of glycol hydrochlorate, it can be used for antibacterial and wetting agent etc..
On the one hand, a kind of lauroyl arginine ethyl ester glycol hydrochlorate, the lauroyl arginine are embodiments provided
The fusing point of ethyl ester glycol hydrochlorate is 85-90 DEG C.The salt with lauroyl arginine ethyl ester hydrochloride as raw material, the neutralization reaction of Jing alkali and
Prepare with glycolic acid salt-forming reaction.
On the other hand, a kind of preparation method of lauroyl arginine ethyl ester glycol hydrochlorate is embodiments provided, should
Method includes：With lauroyl arginine ethyl ester hydrochloride as raw material, it is neutralized reaction with alkali in solvent and removes raw material upper band
HCL, wash or be separated by filtration neutralization reaction generation salt（And excess base）Afterwards, then carry out salt-forming reaction with glycolic acid and obtain the moon
Osmanthus acyl arginine ethyl ester glycol hydrochlorate.
Wherein, in above-mentioned preparation method：The temperature of neutralization reaction and salt-forming reaction be 0-100 DEG C, neutralization reaction when
Between be -2 hours 10 minutes, time of salt-forming reaction is -3 hours 10 minutes, and alkali rubs with lauroyl arginine ethyl ester hydrochloride
You are than being 1-2：1, glycolic acid is 1-2 with the mol ratio of lauroyl arginine ethyl ester hydrochloride：1.Preferably, neutralization reaction and into
The temperature of reactant salt is 20-80 DEG C；It is highly preferred that the temperature of neutralization reaction and salt-forming reaction is 30-60 DEG C.In addition, if anti-
Answer and have in system water（Such as the mixed solvent that solvent is water or water）, then the temperature of neutralization reaction and salt-forming reaction be less than 50 DEG C, with
Reduce the hydrolysis of lauroyl arginine ethyl ester.
Wherein, in above-mentioned preparation method：Solvent selected from water, acetone, butanone, Ketohexamethylene, ethyl acetate, butyl acetate,
Petroleum ether, normal hexane, hexamethylene, acetonitrile or tetrahydrofuran etc., preferably organic solvent, its consumption is lauroyl arginine ethyl ester
1-5 times of hydrochlorate weight.
Wherein, in above-mentioned preparation method：Alkali both can be organic base, or inorganic base, or its mixture；It is organic
Alkali is preferably alkalescence inorganic salt, such as alkali selected from the organic amines such as trimethylamine, triethylamine, ethylenediamine, pyridine or piperidines, inorganic base
Metal carbonate or alkali metal hydrogencarbonate.Specifically, alkali is selected from trimethylamine, triethylamine, ethylenediamine, pyridine, piperidines, carbonic acid
Sodium, sodium bicarbonate, potassium carbonate or potassium bicarbonate etc..
Specifically, the method that the present invention is provided is comprised the following steps：
(1) neutralization reaction：With lauroyl arginine ethyl ester hydrochloride as raw material, reaction is neutralized with alkali in solvent, is reacted
Temperature is 0-100 DEG C, and the response time is -2 hours 10 minutes, and alkali is 1-2 with the mol ratio of lauroyl arginine ethyl ester hydrochloride：
1, impurity is washed or is separated by filtration after the completion of reaction（Salt and the alkali of excess that neutralization reaction is generated）.Wherein, solvent selected from water,
Acetone, butanone, Ketohexamethylene, ethyl acetate, butyl acetate, petroleum ether, normal hexane, hexamethylene, acetonitrile or tetrahydrofuran etc.；Its
In, alkali is selected from trimethylamine, triethylamine, ethylenediamine, pyridine, piperidines, sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate etc..More
Specifically, different impurity-removing methods can be adopted according to the difference of solvent, the solvent for such as using is not compatible with water organic molten
Agent, first-selected filter method；Certainly the method that can also take washing, that is, add water after the completion of reacting, and is layered, and takes organic layer.And for
Solvent for water situation, plus water-immiscible organic solvent extraction, organic layer is taken after layering carries out subsequent reactions；For water with
The mixed solvent of other solvents, after the completion of reaction, taking organic layer carries out subsequent reactions.
(2) salt-forming reaction：The product of step (1) carries out salt-forming reaction with glycolic acid, and reaction temperature is 0-100 DEG C, reaction
Time is -3 hours 10 minutes, and glycolic acid is 1-2 with the mol ratio of lauroyl arginine ethyl ester hydrochloride：1, it is cold after the completion of reaction
But crystallize, filter, be dried to obtain product.
Wherein, in aforementioned base materials：Lauroyl arginine ethyl ester hydrochloride is a kind of new antibacterial, in cosmetics and food
Conduct industry has a wide range of applications, but is difficult drying with fusing point is low, and wherein contains chloride ion, limits it in some aspects
Application.The glycolic acid sterilization certain because the special construction containing hydroxyl and carboxyl makes it have and hygroscopic effect, it is in day
It is that curative effect preferably removes dead bark and fine hair medicament to change in articles for use, can synthesize anti aging effect, skin-lightening cosmetic raw material fruit acid, is had
There are moisturizing, Glycerin, promote epidermal renewal.
Aforementioned two kinds of raw materials are combined the bactericidal effect of the lauroyl arginine ethyl ester glycol hydrochlorate for preparing compared with the moon by the present invention
The effect of osmanthus acyl arginine ethyl ester hydrochloride is more preferable, such as to bacillus subtilises, Listeria monoeytogenes, golden yellow Portugal
The common antibacterial such as grape coccus, escherichia coli, Candida albicans, beer yeast, aspergillus niger, iron bacteria, funguses and mycete have
There is preferable fungistatic effect, i.e., it can be used as antibacterial.In addition, lauroyl arginine ethyl ester glycol hydrochlorate remains glycolic acid
Moisture-keeping function, its wettability power is than common wetting agent so as to can be used as wetting agent.Certainly, lauroyl arginine ethyl ester is sweet
Alcohol hydrochlorate can also simultaneously be used as antibacterial and wetting agent, such as can be used in cosmetics.
To sum up, the advantage of lauroyl arginine ethyl ester hydrochloride and glycolic acid is combined the present invention lauroyl of preparation
Arginine ethyl ester glycol hydrochlorate has fusing point high（85-90 DEG C of fusing point）, easily preparing, preferable bactericidal action is excellent with moisture-keeping function etc.
Point.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, present invention work is further retouched in detail below
State.
Embodiment 1：
42.1 grams of LAE hydrochlorates are weighed, 80 grams of ethyl acetate are added, 70 DEG C of dissolvings are heated to, 8.4 grams of sodium bicarbonate is added, is stirred
Reaction 40 minutes is mixed, is cooled to less than 50 DEG C, filtered, the filtrate for obtaining adds 7.6 grams of glycolic acid, continue stirring reaction 3 hours, it is cold
But crystallize 2 hours to about 15 DEG C, the powder filter for obtaining, be dried, obtain 41.8 grams of product, yield 91%, fusing point is 88-90 DEG C.
HPLC content detection：The content of lauroyl arginine ethyl ester glycol hydrochlorate is 98.1%, main impurity lauroyl arginine
Content be 1.6%.
Embodiment 2：
42.1 grams of LAE hydrochlorates are weighed, 80 grams of butyl acetates are added, 60 DEG C of dissolvings are heated to, 8.4 grams of sodium bicarbonate is added, is stirred
Reaction 1 hour is mixed, is cooled to 40 DEG C of filtrations, the filtrate for obtaining adds 7.6 grams of glycolic acid, continue stirring reaction 1.5 hours, be cooled to
Crystallizing at room temperature 2 hours, the powder filter for obtaining is dried, and obtains 42.5 grams of product, yield 92.3%, and fusing point is 86-89 DEG C.
HPLC content detection：The content of lauroyl arginine ethyl ester glycol hydrochlorate is 97.4%, main impurity lauroyl arginine
Content be 2.1%.
Embodiment 3：
42.1 grams of LAE hydrochlorates are weighed, 80 grams of ethyl acetate are added, 60 DEG C of dissolvings are heated to, 10.1 grams of triethylamine, stirring is added
Reaction 40 minutes, is cooled to 50 DEG C of filtrations, and the filtrate for obtaining adds 7.6 grams of glycolic acid, continues stirring reaction 2 hours, is cooled to 10
DEG C crystallization 3 hours, the powder filter for obtaining is dried, and obtains 42.6 grams of product, yield 92.5%, and fusing point is 87-89 DEG C.
HPLC content detection：The content of lauroyl arginine ethyl ester glycol hydrochlorate is 97.6%, main impurity lauroyl arginine
Content be 1.3%.
Embodiment 4：
42.1 grams of LAE hydrochlorates are weighed, 20 grams of water and 60 grams of ethyl acetate are added, 60 DEG C of dissolvings are heated to, triethylamine is added
10.1 grams, solution is proceeded to separatory funnel by stirring reaction 40 minutes, is stood, after both are layered, branch vibration layer, and, obtain
Organic layer adds 7.6 grams of glycolic acid, continues stirring reaction 3 hours, is cooled to 15 DEG C and crystallizes 2 hours, the powder filter for obtaining,
It is dried, obtains 37.3 grams of product, yield 81%, fusing point is 78-83 DEG C.
HPLC content detection：The content of lauroyl arginine ethyl ester glycol hydrochlorate is 92%, and main impurity lauroyl is arginic
Content is 5.4%.
Embodiment 5：
42.1 grams of LAE hydrochlorates are weighed, 80 grams of butyl acetates are added, 60 DEG C of dissolvings are heated to, 9.5 grams of pyridine is added, stirring is anti-
Answer 1 hour, 20 grams of water added in reactant liquor, water layer is removed after stratification, the organic layer for obtaining adds 9.1 grams of glycolic acid,
Continue stirring reaction 3 hours at 60 DEG C, be cooled to -5 DEG C and crystallize 2 hours, the powder filter for obtaining is dried, and obtains 43.9 grams of product,
Yield 95.2%, fusing point is 88-89 DEG C.
HPLC content detection：The content of lauroyl arginine ethyl ester glycol hydrochlorate is 98.4%, main impurity lauroyl arginine
Content be 1.2%.
Embodiment 6：
42.1 grams of LAE hydrochlorates are weighed, 100 grams of butyl acetates are added, 50 DEG C of dissolvings are heated to, 5.3 grams of sodium carbonate is added, is stirred
Reaction 1 hour is mixed, is cooled to 35 DEG C of 20 grams of purified water of addition, water layer is removed in layering, and the organic layer for obtaining adds glycolic acid 7.6
Gram, continue stirring reaction 3 hours, it is cooled to crystallizing at room temperature 2 hours, the powder filter for obtaining is dried, and obtains 41.5 grams of product, receives
Rate 90.2%, fusing point is 85-87 DEG C
HPLC content detection：The content of lauroyl arginine ethyl ester glycol hydrochlorate is 96.4 %, and main impurity lauroyl essence ammonia contains
Measure as 2.3%.
Embodiment 7：MIC (measure of minimum inhibitory concentration)
Above sinteticses are tested using agar dilution（Meansigma methodss）To several frequently seen antibacterial, funguses, the antibacterial of mycete
Effect, is repeated 3 times while with LAE hydrochlorates as a comparison under the same terms, and other conditions are identical, and LAE glycolic acid salt makes respectively
With the product of embodiment 1,2 and 5, average, as a result such as table 1:
Table 1
| Strain | LAE glycol hydrochlorate minimum inhibitory concentration (ppm) | LAE hydrochlorate minimum inhibitory concentrations (ppm) |
| Bacillus subtilises ATCC 6633 | 16 | 16 |
| Listeria monoeytogenes B4/971 | 25 | 32 |
| Staphylococcus aureuses ATCC 6538 | 8 | 8 |
| Escherichia coli ATCC 35150 | 26 | 32 |
| Candida albicans ATCC 10231 | 14 | 16 |
| Beer yeast ATCC 9763 | 25 | 32 |
| Aspergillus niger ATCC 14604 | 28 | 32 |
| Iron bacteria | 64 | 100 |
Upper table shows LAE glycol hydrochlorate to gram positive bacteria, gram negative bacteria, and yeast and mycete all have good antibacterial
Effect, compared with LAE hydrochlorates, for most strain, its MIC value is less, shows that it has higher antibacterial action.
Embodiment 8：The Preliminary Determination of moisture retention
It it is 20 DEG C in temperature, relative humidity is under 65% the same terms, to weigh a certain amount of LAE glycol hydrochlorate in container, is used
Weighing method determines the hygroscopic capacity of various wetting agents, is defined as follows, and hygroscopic capacity=（Test sample-sample）/ sample × 100%
Compare and be repeated 3 times under test, the same terms with the wetting agent Sorbitol and glycerol commonly used simultaneously, other conditions are identical,
LAE glycolic acid salt using the product of embodiment 1,2 and 5, is averaged respectively, and its result is as shown in table 2：
Table 2
Tentatively may determine that from table 2, the moistening effect of LAE glycol hydrochlorates is higher than LAE hydrochlorates and Sorbitol, less than moistening effect
Best glycerol, but equally there is certain moisture-keeping function.
The foregoing is only presently preferred embodiments of the present invention, not to limit the present invention, all spirit in the present invention and
Within principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.
Claims (10)
1. a kind of lauroyl arginine ethyl ester glycol hydrochlorate, it is characterised in that the lauroyl arginine ethyl ester glycol hydrochlorate
Fusing point is 85-90 DEG C.
2. lauroyl arginine ethyl ester glycol hydrochlorate according to claim 2, it is characterised in that with lauroyl arginine second
Ester hydrochloride is raw material, the neutralization reaction of Jing alkali and is prepared with glycolic acid salt-forming reaction.
3. the preparation method of lauroyl arginine ethyl ester glycol hydrochlorate as claimed in claim 1 or 2, it is characterised in that described
Method includes：
With lauroyl arginine ethyl ester hydrochloride as raw material, it is neutralized reaction with alkali in solvent and removes HCL, separates neutralization anti-
After the salt that should be generated, then carry out salt-forming reaction with glycolic acid and obtain lauroyl arginine ethyl ester glycol hydrochlorate.
4. the preparation method of lauroyl arginine ethyl ester glycol hydrochlorate according to claim 3, it is characterised in that neutralization is anti-
It should be 0-100 DEG C with the temperature of salt-forming reaction, the time of neutralization reaction is -2 hours 10 minutes, and the time of salt-forming reaction is 10 points
Clock -3 hours, the alkali is 1-2 with the mol ratio of lauroyl arginine ethyl ester hydrochloride：1, the glycolic acid and lauroyl essence ammonia
The mol ratio of acid ethyl ester hydrochloride salt is 1-2：1.
5. the preparation method of lauroyl arginine ethyl ester glycol hydrochlorate according to claim 3, it is characterised in that described molten
Agent is selected from water, acetone, butanone, Ketohexamethylene, ethyl acetate, butyl acetate, petroleum ether, normal hexane, hexamethylene, acetonitrile or tetrahydrochysene furan
Mutter, its consumption is 1-5 times of lauroyl arginine ethyl ester hydrochloride weight.
6. the preparation method of lauroyl arginine ethyl ester glycol hydrochlorate according to claim 3, it is characterised in that the alkali
Selected from organic amine, alkali carbonate or alkali metal hydrogencarbonate.
7. the preparation method of lauroyl arginine ethyl ester glycol hydrochlorate according to claim 6, it is characterised in that the alkali
Selected from trimethylamine, triethylamine, ethylenediamine, pyridine, piperidines, sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate.
8. the preparation method of lauroyl arginine ethyl ester glycol hydrochlorate according to claim 3, it is characterised in that the side
Method includes：
(1) neutralization reaction：With lauroyl arginine ethyl ester hydrochloride as raw material, reaction is neutralized with alkali in solvent, is reacted
Temperature is 0-100 DEG C, and the response time is -2 hours 10 minutes, and the alkali is with the mol ratio of lauroyl arginine ethyl ester hydrochloride
1-2：1, impurity is washed or is separated by filtration after the completion of reaction, the solvent is selected from water, acetone, butanone, Ketohexamethylene, acetic acid second
Ester, butyl acetate, petroleum ether, normal hexane, hexamethylene, acetonitrile or tetrahydrofuran, the alkali is selected from trimethylamine, triethylamine, second two
Amine, pyridine, piperidines, sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate；
(2) salt-forming reaction：The product of step (1) carries out salt-forming reaction with glycolic acid, and reaction temperature is 0-100 DEG C, the response time
For -3 hours 10 minutes, the glycolic acid was 1-2 with the mol ratio of lauroyl arginine ethyl ester hydrochloride：1, it is cold after the completion of reaction
But crystallize, filter, be dried to obtain product.
9. the lauroyl arginine ethyl ester glycol hydrochlorate described in claim 1 or 2 is used for the purposes of antibacterial.
10. the lauroyl arginine ethyl ester glycol hydrochlorate described in claim 1 or 2 is used for the purposes of wetting agent.
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| CN107286059A (en) * | 2017-05-19 | 2017-10-24 | 武汉桀升生物科技有限公司 | A kind of preparation method of lauroyl arginine ethyl ester hydrochloride |
| CN107400069A (en) * | 2017-08-01 | 2017-11-28 | 浙江大学 | A kind of preparation method of lauroyl arginine ethyl ester hydrochloride |
| CN108740356A (en) * | 2017-11-03 | 2018-11-06 | 华东师范大学 | Purposes of the lauroyl arginine ethyl ester derivative as feed addictive |
| CN108976151A (en) * | 2017-11-03 | 2018-12-11 | 华东师范大学 | Lauroyl arginine ethyl ester derivative and purposes as animal antibacterial agent |
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