CN108553419A - A kind of Alpha-ethyl linolenate microemulsion and preparation method thereof - Google Patents

A kind of Alpha-ethyl linolenate microemulsion and preparation method thereof Download PDF

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CN108553419A
CN108553419A CN201810507045.6A CN201810507045A CN108553419A CN 108553419 A CN108553419 A CN 108553419A CN 201810507045 A CN201810507045 A CN 201810507045A CN 108553419 A CN108553419 A CN 108553419A
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alpha
microemulsion
ethyl
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ethyl linolenate
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CN108553419B (en
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郑永军
牛永生
郑勇
侯绍刚
贾志强
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Anyang Institute of Technology
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • A61K36/535—Perilla (beefsteak plant)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/55—Linaceae (Flax family), e.g. Linum
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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Abstract

A kind of alpha linolenic acid ethyl ester microemulsion includes oil phase, the surfactant water of alpha linolenic acid ethyl ester or the ethyl ester containing alpha linolenic acid, also contains cosurfactant, and the parts by weight of each component are as follows in microemulsion：4 70 parts of alpha linolenic acid ethyl ester；6 40 parts of surfactant and cosurfactant；0 1.5 parts of inorganic salts；0.1 1.5 parts of antioxidant, surplus is water.The preparation method of alpha linolenic acid ethyl ester microemulsion, including step：A：Accurately weigh required each component；B：Heating temperature is controlled within the scope of 20 30 DEG C, composition mixing oil phase, adds surfactant and cosurfactant thereto after the oil phase and antioxidant of alpha linolenic acid ethyl ester or the ethyl ester containing alpha linolenic acid are mixed；C：Water or the water dissolved with inorganic salts are added in the mixed system that above-mentioned steps B is obtained, is protected and is made full use of the invention enables the alpha linolenic acid in microemulsion.

Description

A kind of Alpha-ethyl linolenate microemulsion and preparation method thereof
Technical field
The present invention relates to Alpha-ethyl linolenate microemulsion, more particularly to a kind of Alpha-ethyl linolenate microemulsion and its preparation side Method belongs to chemical field.
Background technology
Alpha-linolenic acid (α-Linolenic Acid, abbreviation ALA）, scientific name：Allcis-9,12,15-Oc-tadecatrienoic acid, It is a kind of advanced polyunsaturated fatty acid, it is that constitute the important substance and Ω -3 of brain cell and retina be unsaturated lipid The parent of fat acid, by its metabolizable generation eicosapentaenoic acid needed by human（EPA）, clupanodonic acid（DPA）, 20 Two carbon acids（DHA）Three big trophic factors, therefore, alpha-linolenic acid are indispensable nutritional factors in health, and belonging to must Aliphatic acid is needed, however, it is unable to Synthesis in human body, it is necessary to be supplemented by being absorbed in food, supplement this nutrition daily Ingredient has particularly significant effect to health.
Scientific investigations showed that alpha-linolenic acid has reducing blood lipid, blood pressure lowering, antiallergy, antithrombotic, protection eyesight, prevents inflammation Disease increases brain cell substance, improves the effects that memory.Human body lacks alpha-linolenic acid for a long time, and Human Lipid Metabolism can be caused disorderly Disorderly, the symptoms such as immunity reduction, hypopsia, decrease of memory, artery sclerosis are caused to occur, due to general in population of China diet All over alpha-linolenic acid is lacked, causes the cardiovascular and cerebrovascular diseases number such as China's hyperlipidemia and hypertension to increase, directly affect people's Health, for this purpose, the products such as the health products and nourishing additive agent of exploitation rich in alpha-linolenic acid and its derivative are imperative 's.However, alpha-linolenic acid is oxidizable rotten under air, light and heating state, to improve its stability, currently, in the market Existing health products containing alpha-linolenic acid mainly occur with capsule and emulsion form, as 105707568 A of Chinese patent CN are disclosed " a kind of alpha-linolenic acid soft capsule and preparation method with auxiliary lipid-lowering function " passes through microencapsulation form and improves α-flax Absolute acid stability, but it is more due to the use of auxiliary materials such as glycerine, gelatin, to increase liver metabolism burden, moreover the price mesh of capsule It is preceding relatively high.For another example Chinese patent CN104957622 A disclose " one grow flax stable emulsion and preparation method thereof " and pass through The manufactured stable emulsion after emulsification such as protein, flavoring agent, stabilizer or antioxidant is added after flax instant powder is dissolved, Since flax instant powder is using linseed as made of Raw material processing, alpha-linolenic acid content is low, is actually in the breast of less stable Liquid is easily layered, is oxidized easily after layering, and is not easy to the absorption of human body stomach.In order to improve alpha-linolenic acid utilization rate, α-is expanded Leukotrienes application range, it is necessary to carry out Alpha-ethyl linolenate microemulsion and preparation method research.
Microemulsion be two kinds of immiscible oil are formed into Thermodynamically stable with water under Action of Surfactant, appearance is in Transparent or semitransparent, stable homogeneous system of the grain size between 1-100nm, the system is with good stability and dispersed. And the grain size of common emulsion is larger and be unevenly distributed, usual grain size is more than 100nm, and the system is unstable.Microemulsion system Because grain size is smaller, stomach can be convenient for drug absorption, drug effect and utilization ratio of drug is improved and be applied to doctor as pharmaceutical carrier Medicine field.The key technology that microemulsion is formed is found between suitable surfactant and oil phase, water phase and surfactant Proportioning, the microemulsion stability and dispersibility that suitable surfactant and good compatibility are formed is more excellent.China Disclose a variety of other microemulsions in patent application, for example, disclosed in Chinese Patent Application No. 2016111343095 it is a kind of micro- Lotion and preparation method thereof, a kind of water in oil microemulsion detergent for ink disclosed in 2016108448443 and preparation method thereof Deng.But the component selection and compatibility in these microemulsions are not suitable for Alpha-ethyl linolenate microemulsion, seek to develop α-flax Acetoacetic ester microemulsion is the effective way for expanding its application.
Invention content
It is an object of the invention to overcome the above problem present in current Alpha-ethyl linolenate microemulsion preparation, provide A kind of Alpha-ethyl linolenate microemulsion and preparation method thereof.
To achieve the purpose of the present invention, following technical solutions is used：A kind of Alpha-ethyl linolenate microemulsion, including α- Ethyl linolenate or oil phase, surfactant water containing Alpha-ethyl linolenate, also contain cosurfactant, the microemulsion The parts by weight of middle each component are as follows：4-70 parts of Alpha-ethyl linolenate；6-40 parts of surfactant and cosurfactant；It is inorganic 0-1.5 parts of salt；0.1-1.5 parts of antioxidant, surplus are water, Alpha-ethyl linolenate Alpha-ethyl linolenate or purple perilla after purification It is detached after oil and the ethyl esterified perilla herb oil or linseed oil and ethyl alcohol esterification that isolate and purify rear gained after ethyl alcohol esterification pure The ethyl esterified linseed oil of gained after change；The surfactant is Tween80, and cosurfactant is salicylic acid；Further 's；Tween80 and salicylic mass ratio are 10 in the complexed surfactant:1 ；Further；The inorganic salts For sodium chloride or sodium bicarbonate or sodium carbonate, the antioxidant is ascorbic acid or vitamin E or tea polyphenols or dibutyl The combination of hydroxy-methylbenzene or butylated hydroxy anisole or tert-butyl hydroquinone or above-mentioned two of which.
A kind of preparation method of Alpha-ethyl linolenate microemulsion, above-mentioned each component and parts by weight proportioning, including it is following Step：
A：Accurately weigh required each component；
B：Heating temperature is controlled within the scope of 20-30 DEG C, by Alpha-ethyl linolenate or the oil phase containing Alpha-ethyl linolenate and antioxygen Then under slow stirring composition mixing oil phase after agent mixing adds surfactant and cosurfactant thereto, and It is allowed to uniformly mixed；
C：Under slow stirring, water or the water dissolved with inorganic salts are added in the mixed system that above-mentioned steps B is obtained, stirring is equal After even, obtain at this time clear, stable homogeneous nanometer micro-emulsion.
The present invention is with Alpha-ethyl linolenate or ethyl esterified perilla herb oil or ethyl esterified linseed oil, surfactant and helps surface Property agent, water constituent form a kind of stable homogeneous, clear grain size between 1-100nm microemulsion system, formed after measured Microemulsion is oil-in-water, can ensure that it is not oxidized in storage and use, since this microemulsion after dilution can be with Oil-in-water microemulsion characteristic is kept, so the microemulsion of the present invention can be present in the various beverages largely drunk with low concentration Among, the usage scenario of alpha-linolenic acid is expanded significantly, since concentration is low, cost will not be very high, and ordinary consumer can receive, Since this Alpha-ethyl linolenate microemulsion system stability is good, grain size is small and uniform, is convenient for the absorption of human body stomach, makes α-flax Acid absorption rate is high, is a kind of human body supplement effective approach of facility of alpha-linolenic acid to improve the utilization rate of its nutritional ingredient.Together When preparation process of the present invention it is simple, convenient for large-scale production so that the alpha-linolenic acid in microemulsion is protected and is made full use of.
Description of the drawings
Fig. 1 is the microemulsion ternary phase diagrams of the formation of the present invention.
Specific implementation mode
In order to more fully explain the implementation of the present invention, the embodiment of the present invention is provided, these embodiments are only Elaboration to the present invention, does not limit the scope of the invention.
Embodiment 1
At 25 DEG C, in mass ratio by Tween80:Salicylic acid=10：1 composition mixed surfactant 33.6g, 0.084g is tieed up The raw ethyl esterified perilla herb oil of element E, 8.4g is allowed to be uniformly mixed under slow stirring with mixed surfactant, then, to mixture It is slowly added to 58g water in system, after mixed liquor is by muddiness to clear liquid, continuously adds water to required quality（Purpose It is to adjust concentration, according to the additive amount for needing to determine water of ultimate density）, at this point, being still clear liquid.
The oil-in-water microemulsion of Alpha-ethyl linolenate nanoscale appearance clear is prepared in the present embodiment.Further Ground dissipates instrument using dynamic optical to the nanoscale microemulsion of the present embodiment and carries out particle size determination to it, and mean particle radius is 14.407nm, and stability analysis is carried out to it：This microemulsion is placed in centrifugation 30min under 3000r/min not to be separated Phenomenon, or take out liquid and with laser bunchy after laser pen irradiating liquids and do not disperse in beaker, i.e., Tyndall phenomenon is apparent, room Phenomenon of phase separation does not occur for lower preserve 2 months of temperature, illustrates that it has good stability.
Embodiment 2
At 25 DEG C, in mass ratio by Tween80:Salicylic acid=10:1 composition mixed surfactant 3.5g, 0.057g is tieed up The raw ethyl esterified perilla herb oil of element E, 5.7g is allowed to be uniformly mixed under slow stirring with mixed surfactant, then, to mixture It is slowly added to 0.7g water in system, after solution becomes the liquid of clear from muddiness, then, carefully adds water to required quality （Purpose is to adjust concentration, according to the additive amount for needing to determine water of ultimate density）, at this point, being still clear liquid.
The water in oil microemulsion of Alpha-ethyl linolenate nanoscale appearance clear is prepared in the present embodiment.Into one Step carries out stability analysis to the Alpha-ethyl linolenate nanoscale microemulsion product of this implementation：This microemulsion is placed in 3000r/min 30min is centrifuged in lower supercentrifuge and does not occur phenomenon of phase separation, or takes out liquid in beaker with after laser pen irradiating liquids Laser bunchy and do not disperse, i.e., Tyndall phenomenon is apparent, preserves 2 months phenomenon of phase separation does not occur at room temperature, illustrate its stabilization Property is good.
Embodiment 3
At 25 DEG C, in mass ratio by Tween80:Salicylic acid=10:1 forms mixed surfactant 4.5g, and 0.049g is anti-bad The ethyl esterified perilla herb oil of hematic acid, 4.9g is allowed to be uniformly mixed under slow stirring with mixed surfactant, then to mixed system In be slowly added to 0.6g water, after solution becomes clear liquid from muddiness, then, carefully add water to required quality（Mesh Be adjust concentration, according to ultimate density need determine water additive amount）, at this point, being still clear liquid.
The water in oil microemulsion of Alpha-ethyl linolenate nanoscale appearance clear is prepared in the present embodiment.Into one Step carries out stability analysis to the Alpha-ethyl linolenate nanoscale microemulsion product of this implementation：This microemulsion is placed in 3000r/min 30min is centrifuged in lower supercentrifuge and does not occur phenomenon of phase separation, or takes out liquid in beaker with after laser pen irradiating liquids Laser bunchy and do not disperse, i.e., Tyndall phenomenon is bright, preserves 2 months phenomenon of phase separation does not occur at room temperature, illustrate its stability Well.
Embodiment 4
At 25 DEG C, in mass ratio by Tween80:Salicylic acid=10：1 composition mixed surfactant 280.4g, 0.84g is resisted The ethyl esterified perilla herb oil of bad hematic acid, 70.01g is allowed to be uniformly mixed under slow stirring with mixed surfactant, then to mixing It is slowly added to 649.5g water in system, after mixed liquor is by muddiness to clear liquid, continuously adds water to required quality （Purpose is to adjust concentration, according to the additive amount for needing to determine water of ultimate density）, at this point, being still clear liquid.
The microemulsion of the oil-in-water type of Alpha-ethyl linolenate nanoscale appearance clear is prepared in the present embodiment.Into one Step ground dissipates instrument using dynamic optical to the nanoscale microemulsion of the present embodiment and carries out particle size determination to it, and mean particle radius is 11.659nm, and stability analysis is carried out to it：This microemulsion is placed in centrifugation 30min under 3000r/min not to be separated Phenomenon, or take out liquid and with laser bunchy after laser pen irradiating liquids and do not disperse in beaker, i.e., Tyndall phenomenon is apparent, room Phenomenon of phase separation does not occur for lower preserve 2 months of temperature, illustrates that it has good stability.
Embodiment 5
（1）At 25 DEG C, composition blending surface activity after in mass ratio mixing 403.5gTween80 and 40.35g salicylic acids 0.55g vitamin Es and the ethyl esterified perilla herb oils of 55.48g are made to be uniformly mixed under slow stirring by agent with mixed surfactant, Obtain finely dispersed oil phase component；
（2）At 25 DEG C, with mixing speed 3500rpm whipping steps（1）The oil phase component of gained, while 722.6g water being added Wherein, control heating medium temperature is within the scope of 25 DEG C, incorporation time about 30min, obtains clear homogeneous and stablizes liquid.
The microemulsion of the oil-in-water type of Alpha-ethyl linolenate nanoscale appearance clear is prepared in the present embodiment.Into one Step ground dissipates instrument using dynamic optical to the nanoscale microemulsion of the present embodiment and carries out particle size determination to it, and mean particle radius is 8.823nm, and stability analysis is carried out to it：This microemulsion is placed in centrifugation 30min under 3000r/min and does not occur phase separation now As, or take out liquid and with laser bunchy after laser pen irradiating liquids and do not disperse in beaker, i.e., Tyndall phenomenon is apparent, room temperature Phenomenon of phase separation does not occur for lower preserve 2 months, illustrates that it has good stability.
Alpha-ethyl linolenate mass content in the various embodiments described above in used ethyl esterified perilla herb oil is 60%, phasor In oil refer to ethyl esterified perilla herb oil, Alpha-ethyl linolenate mass content therein is 60%.
After the embodiment that the present invention will be described in detail, one of ordinary skilled in the art is clearly understood that, is not taking off It is lower from above-mentioned claim and spirit to carry out various change and modification, it is all according to the technical essence of the invention to it is above in fact Any simple modification, equivalent change and modification made by example are applied, belong to the range of technical solution of the present invention, and the present invention is also not It is limited to the embodiment of example in specification.

Claims (4)

1. a kind of Alpha-ethyl linolenate microemulsion, including Alpha-ethyl linolenate or the oil phase containing Alpha-ethyl linolenate, surface-active Agent water, it is characterised in that：Also contain cosurfactant, the parts by weight of each component are as follows in the microemulsion：α-flax 4-70 parts of acetoacetic ester；6-40 parts of surfactant and cosurfactant；0-1.5 parts of inorganic salts；0.1-1.5 parts of antioxidant, Surplus is water, after Alpha-ethyl linolenate isolates and purifies after Alpha-ethyl linolenate after purification or perilla herb oil and ethyl alcohol esterification The ethyl esterified linseed oil of rear gained is isolated and purified after the ethyl esterified perilla herb oil or linseed oil of gained and ethyl alcohol esterification；Described Surfactant is Tween80, and cosurfactant is salicylic acid.
2. a kind of Alpha-ethyl linolenate microemulsion according to claim 1, it is characterised in that：The composite surface activity Tween80 and salicylic mass ratio are 10 in agent:1 .
3. a kind of Alpha-ethyl linolenate microemulsion according to claim 1, it is characterised in that：The inorganic salts are chlorination Sodium or sodium bicarbonate or sodium carbonate, the antioxidant are ascorbic acid or vitamin E or tea polyphenols or butylated hydroxy-a The combination of benzene or butylated hydroxy anisole or tert-butyl hydroquinone or above-mentioned two of which.
4. a kind of preparation method of Alpha-ethyl linolenate microemulsion, using each component and parts by weight described in claim 1 Proportioning, it is characterised in that：Include the following steps：
A：Accurately weigh required each component；
B：Heating temperature is controlled within the scope of 20-30 DEG C, by Alpha-ethyl linolenate or the oil phase containing Alpha-ethyl linolenate and antioxygen Then under slow stirring composition mixing oil phase after agent mixing adds surfactant and cosurfactant thereto, and It is allowed to uniformly mixed；
C：Under slow stirring, water or the water dissolved with inorganic salts are added in the mixed system that above-mentioned steps B is obtained, stirring is equal After even, obtain at this time clear, stable homogeneous nanometer micro-emulsion.
CN201810507045.6A 2018-05-24 2018-05-24 A kind of Alpha-ethyl linolenate microemulsion and preparation method thereof Expired - Fee Related CN108553419B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110463783A (en) * 2019-09-10 2019-11-19 王小锋 Alpha-linolenic acid micro emulsion and preparation method thereof
CN112479885A (en) * 2021-01-01 2021-03-12 河南利诺生化有限责任公司 Low-cost environment-friendly production process of ethyl linolenate

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