CN109575023A - A kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof - Google Patents
A kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof Download PDFInfo
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- CN109575023A CN109575023A CN201811467058.1A CN201811467058A CN109575023A CN 109575023 A CN109575023 A CN 109575023A CN 201811467058 A CN201811467058 A CN 201811467058A CN 109575023 A CN109575023 A CN 109575023A
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- chain fatty
- matrine
- fatty acids
- long chain
- ionic liquid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- 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
-
- A—HUMAN NECESSITIES
- 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
- A61Q17/02—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 containing insect repellants
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof.Wherein, method includes: under atmosphere of inert gases, with 1-5 times of volume of solvent dissolution long chain fatty acids in reactor；The backbone c atoms number of the long chain fatty acids is more than or equal to 6；Matrine is dissolved with 1-5 times of volume of solvent, and is added dropwise in the reactor dissolved with long chain fatty acids, Ionization Modification reaction is carried out；After reaction, condensing crystallizing is carried out to reaction solution under vacuum conditions, obtains matrine long chain fatty acids ionic liquid.Matrine hard soap of the present invention is ionic liquid at room temperature, with good solubility, trap and stability, the matrine long chain fatty acids ionic liquid and nonpolar ethers or water, methanol, ethyl alcohol isopolarity solvent, it all can almost be dissolved each other with arbitrary proportion, there is excellent Transdermal absorption effect.
Description
Technical field
The present invention relates to medicine, compound field used for cosmetic more particularly to a kind of matrine long chain fatty acids ionic liquids
Body and the preparation method and application thereof.
Background technique
Matrine is a kind of alkaloid extracted from kuh-seng, has reported that matrine has multiple pharmacological effect, packet
Include anti-inflammatory, immunological regulation etc..Current study show that matrine Central nervous system have it is antipyretic, analgesia, it is anticonvulsion, stable
The effects of neural；Have the function of apparent negative chronotropic and positive inotropic to cardiovascular system, have prevention and treatment atherosclerosis,
Mitigate the function of myocardial damage;The effect of anti-liver injury, anti-fibrosis can be played to digestive system；In addition to this also have
Antitumor, anti-liver cancer and anti-effect.But there is the disadvantages of activity is single, dissolubility is general in matrine monomer in application process.
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of matrine long chain fatty acids ionic liquids
Body and the preparation method and application thereof, it is intended to solve existing matrine monomer exist in application process active single, dissolubility compared with
The problem of difference etc..
Technical scheme is as follows:
A kind of preparation method of matrine long chain fatty acids ionic liquid, wherein the following steps are included:
Under atmosphere of inert gases, with 1-5 times of volume of organic solvent dissolution long chain fatty acids in reactor；The long-chain rouge
The backbone c atoms number of fat acid is more than or equal to 6；
Matrine is dissolved with 1-5 times of volume of organic solvent, and is added dropwise in the reactor dissolved with long chain fatty acids, is carried out
Ionization Modification reaction；
After reaction, be concentrated simultaneously freezing and crystallizing to reaction solution under vacuum conditions, obtain pure matrine long-chain rouge
Fat acid ion liquid.
The preparation method of the matrine long chain fatty acids ionic liquid, wherein the long chain fatty acids are caproic acid, pungent
One of acid, capric acid, lauric acid, myristic acid and palmitinic acid.
The preparation method of the matrine long chain fatty acids ionic liquid, wherein the solvent is acetone, methanol, second
One of pure and mild ethyl acetate.
The preparation method of the matrine long chain fatty acids ionic liquid, wherein the long chain fatty acids and the hardship
The molar ratio for joining alkali is (1:0.8)-(1:1.5).
The preparation method of the matrine long chain fatty acids ionic liquid, wherein the temperature of the Ionization Modification reaction
Degree is 40-90 DEG C.
The preparation method of the matrine long chain fatty acids ionic liquid, wherein Ionization Modification reaction when
Between be 4-24h.
The preparation method of the matrine long chain fatty acids ionic liquid, wherein described under vacuum conditions to reaction
It includes: that reaction solution is concentrated under vacuum conditions that liquid, which carries out the step of condensing crystallizing, be concentrated into the 1/5 of reaction solution volume to
1/10, then carry out freezing and crystallizing.
The preparation method of the matrine long chain fatty acids ionic liquid, wherein further include: obtained matrine is long
Chain fatty acid ionic liquid is successively filtered separation and vacuum drying, and wherein drying time is 24-72h.
A kind of matrine long chain fatty acids ionic liquid, wherein using matrine long chain fatty acids of the present invention from
The preparation method of sub- liquid is prepared.
A kind of application of matrine long chain fatty acids ionic liquid, wherein by matrine long-chain fat of the present invention
Acid ion liquid is used as the formula material of cosmetics；Alternatively, matrine long chain fatty acids ionic liquid of the present invention is used
Make extractant and surfactant.
The utility model has the advantages that be cationic presoma with matrine in the present invention, using long chain fatty acids as anion presoma,
Synthesis matrine long chain fatty acids ionic liquid is reacted by Ionization Modification, product is realized by condensing crystallizing after reaction
Isolate and purify.Matrine hard soap of the present invention is ionic liquid at room temperature, compared to solid matrine monomer and salt
Class, have better solubility, trap and stability, test indicate that matrine long chain fatty acids ionic liquid with it is non-
Polar ethers or water, methanol, ethyl alcohol isopolarity solvent, all can almost be dissolved each other with arbitrary proportion, have excellent transdermal suction
It produces effects fruit；In addition, matrine long chain fatty acids ionic liquid of the present invention has matrine and long chain fatty acids every in effect
Function and have reinforcing effect.
Detailed description of the invention
Fig. 1 is matrine octanoic acid ionic liquid nucleus magnetic hydrogen spectrum.
Fig. 2 is matrine octanoic acid ionic liquid nuclear-magnetism carbon spectrum.
Fig. 3 is matrine lauric acid ionic liquid nucleus magnetic hydrogen spectrum.
Fig. 4 is matrine lauric acid ionic liquid nuclear-magnetism carbon spectrum.
Specific embodiment
The present invention provides a kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof, of the invention to make
Purpose, technical solution and effect are clearer, clear, and the present invention is described in more detail below.It should be appreciated that this place is retouched
The specific embodiment stated is only used to explain the present invention, is not intended to limit the present invention.
The embodiment of the present invention provides a kind of preparation method of matrine long chain fatty acids ionic liquid, wherein including following
Step:
Under atmosphere of inert gases, with 1-5 times of volume of solvent dissolution long chain fatty acids in reactor；The long chain fatty acids
Backbone c atoms number be more than or equal to 6；
Matrine is dissolved with 1-5 times of volume of solvent, and is added dropwise in the reactor dissolved with long chain fatty acids, ion is carried out
Change modified-reaction；
After reaction, condensing crystallizing is carried out to reaction solution under vacuum conditions, obtains matrine long chain fatty acids ionic liquid.
It is that cationic presoma passes through ion using long chain fatty acids as anion presoma with matrine in the present embodiment
Change modified-reaction and synthesize matrine long chain fatty acids ionic liquid, realizes that the separation of product is pure by condensing crystallizing after reaction
Change.The present embodiment matrine hard soap is that ionic liquid at room temperature has compared to solid matrine monomer and salt
Better solubility, trap and stability, test indicate that matrine long chain fatty acids ionic liquid with it is nonpolar
Ethers or water, methanol, ethyl alcohol isopolarity solvent, all can almost be dissolved each other with arbitrary proportion, have excellent Transdermal absorption effect；
In addition, matrine long chain fatty acids ionic liquid of the present invention have in effect matrine and long chain fatty acids various functions and
With reinforcing effect.In addition, the present embodiment is successfully prepared matrine long chain fatty acids ionic liquid, this method is using simple easy
The usual vehicle obtained is also easily achieved as reaction medium, instrument and reaction condition, and synthesis step is succinct, post-processing side
Just, products obtained therefrom purity is high, high income can meet general Study requirement.
In the present embodiment, the long chain fatty acids refer to the saturation and unsaturation that the carbon atom number on main chain is more than or equal to 6
Fatty acid has the effects that reduce blood lipid, reduces cholesterol, and longer carbochain helps to improve its corresponding alkaloid ion salt
Fat-soluble and oil-soluble, formed and a kind of be not only dissolved in water and be dissolved in oily pure natural surfactant.In a kind of preferred implementation
In mode, the long chain fatty acids are one of caproic acid, octanoic acid, capric acid, lauric acid, myristic acid and palmitinic acid etc..
In a preferred embodiment, the solvent is one of acetone, methanol, ethyl alcohol and ethyl acetate etc..
It is furthermore preferred that the solvent is methanol or ethyl alcohol, to improve the Crystallization Separation effect of product.
In a preferred embodiment, the long chain fatty acids and the molar ratio of the matrine are (1:0.8)-
(1:1.5).It is furthermore preferred that the long chain fatty acids and the molar ratio of the matrine are (1:0.9)-(1:1.2).
In a preferred embodiment, the temperature of the Ionization Modification reaction is 40-90 DEG C, in the reaction temperature
Under, there is faster reaction rate.
In a preferred embodiment, the time of the Ionization Modification reaction is 4-24h, in the reaction time
Under, fully reacting can be made.
In a preferred embodiment, the step of condensing crystallizing is carried out to reaction solution under vacuum conditions packet
It includes: reaction solution being concentrated under vacuum conditions, be concentrated into the 1/5 to 1/10 of reaction solution volume, then carry out freezing and crystallizing, with
All over products is crystallized as far as possible and is precipitated.
In a preferred embodiment, further includes: by obtained matrine long chain fatty acids ionic liquid successively into
Row is separated by filtration and is dried in vacuo, and wherein drying time is 24-72h, thoroughly to remove the residual solvent in product.
The embodiment of the present invention also provides a kind of matrine long chain fatty acids ionic liquid, wherein uses the embodiment of the present invention
The preparation method of the matrine long chain fatty acids ionic liquid is prepared.
The embodiment of the present invention also provides a kind of application of matrine long chain fatty acids ionic liquid, wherein will be of the invention real
Apply the formula material that matrine long chain fatty acids ionic liquid described in example is used as cosmetics；Alternatively, by institute of the embodiment of the present invention
The matrine long chain fatty acids ionic liquid stated is used as extractant and surfactant.In other words, hardship described in the present embodiment
Ginseng alkali long chain fatty acids ionic liquid can not only be used for the formula material of anti-inflammatory bactericidal agent, mite killing except acne agent etc. for cosmetics,
It may be used as extractant and surfactant.
Below by embodiment, the present invention is further described.
Embodiment 1
The preparation method of the present embodiment matrine octanoic acid ionic liquid, comprising the following steps:
Under argon atmosphere, 0.01 mol octanoic acid is dissolved in reactor with the methanol of 30 ml, is dissolved with the methanol of 50 ml
0.01 mol matrine, and be added dropwise in the reactor dissolved with octanoic acid, 55 DEG C are heated to, Ionization Modification reaction 20 is small
When；
After completion of the reaction, under vacuum conditions concentrate solution to reaction solution 1/8, freezing and crystallizing, and be filtered, washed separation
The crystalline product of matrine octanoic acid ionic liquid is obtained, it is pungent to obtain pure matrine within dry 48 hours in a vacuum drying oven
Acid ion liquid.Its hydrogen nuclear magnetic resonance spectrogram, carbon-13 nmr spectra figure difference are as shown in Figure 1 and Figure 2.
Embodiment 2
The preparation method of the present embodiment matrine lauric acid ionic liquid, comprising the following steps:
Under argon atmosphere, 0.01 mol lauric acid is dissolved in reactor with the methanol of 40 ml, is dissolved with the methanol of 50 ml
0.01 mol matrine, and be added dropwise dissolved in lauric reactor, being heated to 70 DEG C, Ionization Modification reaction 24 is small
When；
After completion of the reaction, under vacuum conditions concentrate solution to reaction solution 1/10, freezing and crystallizing, and be filtered, washed point
From matrine lauric acid ionic liquid crystalline product is obtained, dries in a vacuum drying oven 48 hours and obtain pure matrine
Lauric acid ionic liquid.Its hydrogen nuclear magnetic resonance spectrogram, carbon-13 nmr spectra figure difference are as shown in Figure 3, Figure 4.
In conclusion a kind of matrine long chain fatty acids ionic liquid provided by the invention and the preparation method and application thereof.This hair
Bright with matrine is cationic presoma, using long chain fatty acids as anion presoma, passes through Ionization Modification reaction synthesis hardship
Join alkali long chain fatty acids ionic liquid, isolating and purifying for product is realized by condensing crystallizing after reaction.The matrine is long
Chain fatty hydrochlorate is ionic liquid at room temperature, has good solubility, trap and stability, the matrine long chain fatty acids
Ionic liquid and nonpolar ethers or water, methanol, ethyl alcohol isopolarity solvent, all can almost be dissolved each other with arbitrary proportion,
With excellent Transdermal absorption effect.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. a kind of preparation method of matrine long chain fatty acids ionic liquid, which comprises the following steps:
Under atmosphere of inert gases, with 1-5 times of volume of solvent dissolution long chain fatty acids in reactor；The long chain fatty acids
Backbone c atoms number be more than or equal to 6；
Matrine is dissolved with 1-5 times of volume of solvent, and is added dropwise in the reactor dissolved with long chain fatty acids, ion is carried out
Change modified-reaction；
After reaction, condensing crystallizing is carried out to reaction solution under vacuum conditions, obtains matrine long chain fatty acids ionic liquid.
2. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that the length
Chain fatty acid is one of caproic acid, palmitinic acid, lauric acid, myristic acid and palmitinic acid.
3. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that described molten
Agent is one of acetone, methanol, ethyl alcohol and ethyl acetate.
4. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that the length
The molar ratio of chain fatty acid and the matrine is (1:0.8)-(1:1.5).
5. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that it is described from
The temperature of sonization modified-reaction is 40-90 DEG C.
6. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that it is described from
The time of sonization modified-reaction is 4-24h.
7. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that it is described
The step of carrying out condensing crystallizing to reaction solution under vacuum condition includes: that reaction solution is concentrated under vacuum conditions, is concentrated into
The 1/5 to 1/10 of reaction solution volume, then carry out freezing and crystallizing.
8. the preparation method of matrine long chain fatty acids ionic liquid according to claim 1, which is characterized in that also wrap
Include: obtained matrine long chain fatty acids ionic liquid be successively filtered separation and vacuum drying, wherein drying time be
24-72h。
9. a kind of matrine long chain fatty acids ionic liquid, which is characterized in that use the described in any item kuh-sengs of claim 1-8
The preparation method of alkali long chain fatty acids ionic liquid is prepared.
10. a kind of application of matrine long chain fatty acids ionic liquid, which is characterized in that by matrine as claimed in claim 9
Long chain fatty acids ionic liquid is used as the formula material of cosmetics；Alternatively, by matrine long chain fatty acids as claimed in claim 9
Ionic liquid is used as extractant and surfactant.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811467058.1A CN109575023A (en) | 2018-12-03 | 2018-12-03 | A kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof |
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| CN201811467058.1A CN109575023A (en) | 2018-12-03 | 2018-12-03 | A kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253401A (en) * | 2020-03-17 | 2020-06-09 | 珠海萱嘉君行健康产业发展有限公司 | Non-steroidal aryl alkanoic acid ionic salt and preparation method and application thereof |
| CN113633562A (en) * | 2021-08-11 | 2021-11-12 | 深圳市萱嘉生物科技有限公司 | Matrine vegetable oil eutectic solvent and preparation method, application and product thereof |
| CN113768806A (en) * | 2021-08-16 | 2021-12-10 | 深圳市萱嘉生物科技有限公司 | Glabridin ionic liquid nano solution and preparation method and application thereof |
| CN115894493A (en) * | 2022-12-05 | 2023-04-04 | 哈尔滨工业大学（深圳） | Alkaloid derived ionic liquid based on dicyandiamide anions and preparation method thereof |
| CN116585217A (en) * | 2023-07-17 | 2023-08-15 | 深圳市护家科技有限公司 | Retinol wrap, raw material and external skin preparation easier to be absorbed through skin |
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| CN101260051A (en) * | 2008-04-24 | 2008-09-10 | 中国科学院过程工程研究所 | Biodegradable choline-like ionic liquid |
| CN105315164A (en) * | 2014-08-01 | 2016-02-10 | 中国科学院大连化学物理研究所 | Environment-friendly choline ionic liquid and preparation method therefor |
| CN108079896A (en) * | 2018-02-07 | 2018-05-29 | 广州中健健康科技有限公司 | It is a kind of using biology base ionic liquid by the method for water oil body electropolymerization |
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| JPH04356423A (en) * | 1991-05-31 | 1992-12-10 | Masao Saito | Medicated cream and its production |
| CN101260051A (en) * | 2008-04-24 | 2008-09-10 | 中国科学院过程工程研究所 | Biodegradable choline-like ionic liquid |
| CN105315164A (en) * | 2014-08-01 | 2016-02-10 | 中国科学院大连化学物理研究所 | Environment-friendly choline ionic liquid and preparation method therefor |
| CN108079896A (en) * | 2018-02-07 | 2018-05-29 | 广州中健健康科技有限公司 | It is a kind of using biology base ionic liquid by the method for water oil body electropolymerization |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253401A (en) * | 2020-03-17 | 2020-06-09 | 珠海萱嘉君行健康产业发展有限公司 | Non-steroidal aryl alkanoic acid ionic salt and preparation method and application thereof |
| CN113633562A (en) * | 2021-08-11 | 2021-11-12 | 深圳市萱嘉生物科技有限公司 | Matrine vegetable oil eutectic solvent and preparation method, application and product thereof |
| CN113633562B (en) * | 2021-08-11 | 2024-05-28 | 广东萱嘉医品健康科技有限公司 | Matrine vegetable oil eutectic solvent and preparation method, application and product thereof |
| CN113768806A (en) * | 2021-08-16 | 2021-12-10 | 深圳市萱嘉生物科技有限公司 | Glabridin ionic liquid nano solution and preparation method and application thereof |
| CN115894493A (en) * | 2022-12-05 | 2023-04-04 | 哈尔滨工业大学（深圳） | Alkaloid derived ionic liquid based on dicyandiamide anions and preparation method thereof |
| CN115894493B (en) * | 2022-12-05 | 2024-03-22 | 哈尔滨工业大学（深圳） | Alkaloid derived ionic liquid based on dicyandiamide anions and preparation method thereof |
| CN116585217A (en) * | 2023-07-17 | 2023-08-15 | 深圳市护家科技有限公司 | Retinol wrap, raw material and external skin preparation easier to be absorbed through skin |
| CN116585217B (en) * | 2023-07-17 | 2024-04-16 | 深圳市护家科技有限公司 | Retinol wrap, raw material and external skin preparation easier to be absorbed through skin |
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Application publication date: 20190405 |