CN105687134A - Preparing method of ferulic acid microemulsion preparation - Google Patents
Preparing method of ferulic acid microemulsion preparation Download PDFInfo
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- CN105687134A CN105687134A CN201610151239.8A CN201610151239A CN105687134A CN 105687134 A CN105687134 A CN 105687134A CN 201610151239 A CN201610151239 A CN 201610151239A CN 105687134 A CN105687134 A CN 105687134A
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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- 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
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
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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
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Abstract
The invention discloses a preparing method of a ferulic acid microemulsion preparation, and belongs to the field of microemulsion preparations. The preparing method includes the steps that tea saponin and palmitoyl chloride are reacted to generate tea saponin palmitate serving as a natural emulsifier, ferulic acid is dissolved in an ethyl alcohol co-emulsifier to form a ferulic acid solution, then the ferulic acid solution, an oil phase and the tea saponin palmitate emulsifier are proportionally mixed to form microemulsion concentrate, and hot water is added for dilution to obtain microemulsion. According to the preparing method, prepared tea saponin palmitate serves as the natural emulsifier, so that the emulsifying effect is good, no toxin exists, and environmental friendliness is achieved; besides, ferulic acid is prepared into the microemulsion preparation, preparation is easy, the nature is stable, and the bioavailability of medicine is high.
Description
Technical field
The preparation method that the invention discloses a kind of ferulic acid microemulsion formulation, belongs to microemulsion formulation field。
Background technology
Ferulic acid is the functional liposoluble ingredient of the one being prevalent in plant, cross-links with polysaccharide and lignin and constitutes
A part for plant cell wall, is one of phenolic acid that in the foods such as arithoke, Fructus Solani melongenae, Semen Maydis, content is maximum, is also one of effective ingredient of conventional Chinese medicine such as Radix Angelicae Sinensis, Rhizoma Cimicifugae, Rhizoma Chuanxiong。Ferulic acid is the phenolic hydroxyl group methoxylated product of caffeic acid 3 in chemical constitution, has very strong antioxidant activity, it is possible to multiple free radical in purged body, including hydrogen peroxide, superoxide radical, hydroxy radical, peroxynitrite etc.。Cardiovascular system, nervous system, kidney etc. are had very strong protective effect by it, can be clinically used for treatment respiratory system, cardiovascular and
The diseases such as urinary system。Because going ferulic acid self to be slightly soluble in water, be dissolved in hot water, ethanol and ethyl acetate, internal metabolism rapidly, blood drug level and bioavailability is low etc. that reason significantly limit its application clinically。In order to solve these problems, it is possible to improving its blood drug level by changing dosage form, reduce metabolism, improving bioavailability, thus promoting the using value of ferulic acid。
Microemulsion drug-supplying system is a kind of mixture being mixed to form in appropriate proportions by medicine, oil phase (i.e. oil phase component), water, emulsifying agent and co-emulsifier, mean diameter is 10-100nm, external form thermodynamic stable system, by emulsifying agent and co-emulsifier jointly Stabilization；Water solublity, fat-soluble and insoluble drug are all had good dissolving power, and physical stability is higher；Because surface tension is relatively low, therefore easily through the hydrated sheath of gastrointestinal wall, medicine can directly contact with gastrointestinal epithelial cell, promotes drug absorption, improves bioavailability；Can obstacle through lymphatic absorption, when overcoming first pass effect and macromole by gastrointestinal tract epithelial cell film after oral。
But, the preparation of microemulsion there is also a lot of difficulties。Owing to microemulsion needing substantial amounts of emulsifying agent, along with emulsifier content increase and accumulation in vivo certainly will produce certain toxicity, and the particle diameter of microemulsion and stability thereof all can be produced great impact by co-emulsifier, oil phase and the proportion relation between them。
Summary of the invention
The technical problem that present invention mainly solves: be slightly soluble in water for ferulic acid self, it is dissolved in hot water, ethanol and ethyl acetate, internal metabolism is rapid, blood drug level and bioavailability are low, and prepare now in microemulsion and need substantial amounts of emulsifying agent, along with increasing and problem that accumulation in vivo certainly will produce certain toxicity of emulsifier content, the preparation method providing a kind of ferulic acid microemulsion formulation, tea saponin and Hexadecanoyl chloride are reacted generation tea saponin cetylate as naturally occurring emulsifying agent by the present invention, ferulic acid is dissolved in formation ferulic acid solution in ethanol co-emulsifier, itself and oil phase again, tea saponin cetylate emulsifying agent is mixed in proportion formation microemulsion concentrate, add hot water and dilute to obtain microemulsion, the present invention is prepared into tea saponin cetylate as naturally occurring emulsifying agent, emulsifying effectiveness is good, asepsis environment-protecting, and ferulic acid is made microemulsion formulation, its preparation is simple, stable in properties, the bioavailability of medicine is high。
In order to solve above-mentioned technical problem, the technical solution adopted in the present invention is:
(1) weigh 2～5g tea saponin and 5～12g potassium carbonate loads in 500mL flask, N is being added by solid-to-liquid ratio 1:5 in flask, dinethylformamide, stir to solid dissolving, stirring reaction 20～30min at 0～5 DEG C is put in ice-water bath after dissolving, it is slowly added dropwise 5～8mL Hexadecanoyl chloride after reaction, controls 3～5min and drip off, after dropping, continue stirring reaction 1～2h；
(2) after above-mentioned reaction terminates, it is added thereto to distilled water by reactant liquor volume ratio 3:1, continue stirring reaction 15～20min, reactant liquor in bottle is added macroporous resin adsorption 2～3h, with clear water rinse resin to clarification after adsorption equilibrium, the ethanol every time adding 60～80mL mass fraction 90% in the resin after cleaning resolves, repeated resolution 3～5 times, the desorbed solution rotary evaporation obtained is removed ethanol, regulating desorbed solution pH with mass concentration 25% hydrochloric acid is 3.5～4.0, extract 2～3 times with the mixed liquor of petroleum ether and ethyl acetate volume ratio 5:2 after adjustment, remove fatty acid, by aqueous phase spin concentration 2～3h at 55～60 DEG C, by concentrated solution lyophilization, obtain tea saponin cetylate；
(3) measuring 120～150mL dehydrated alcohol as co-emulsifier, be added thereto to 5～8g ferulic acid, at 40～50 DEG C, ultrasonic dissolution 20～30min obtains ferulic acid solution, standby；
(4) agent by weight, choose 15～30 parts of above-mentioned ferulic acid solution and the tea saponin cetylate mixing of 20～40 parts of oil phases, 40～50 parts of steps (3) respectively, high-speed stirred 5～10min under 3000～6000rpm, put in the water bath with thermostatic control of 30～50 DEG C after stirring, being stirred when 1000～1500rpm, stirring is slowly added 60～70 DEG C of hot water, till solution becomes muddiness again from turbid solution change clarification, it is cooled to room temperature, forms ferulic acid microemulsion formulation。
Described oil phase is one of following components: Oleum sesami, Oleum Ricini, Semen Maydis oil, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen。
The method of the application of the present invention: the microemulsion of the present invention can be made into oral liquid, tablet, capsule, also apply be applicable in injection, lotion, liniment, patch or electuary, oral liquid, tablet, capsule take after under physiological body temperature, gastrointestinal motility effect, meet water or gastro-intestinal Fluid is dispersed into the particle diameter nano level microemulsion particles about below 420nm, it is appreciated that in the absorption of human body。
The invention has the beneficial effects as follows:
(1) present invention is prepared into tea saponin cetylate as naturally occurring emulsifying agent, and emulsifying effectiveness is good, asepsis environment-protecting；
(2) present invention incites somebody to action and ferulic acid is made microemulsion formulation, and its preparation is simple, stable in properties, and the bioavailability of medicine is high。
Detailed description of the invention
First weigh 2～5g tea saponin and 5～12g potassium carbonate loads in 500mL flask, N is being added by solid-to-liquid ratio 1:5 in flask, dinethylformamide, stir to solid dissolving, stirring reaction 20～30min at 0～5 DEG C is put in ice-water bath after dissolving, it is slowly added dropwise 5～8mL Hexadecanoyl chloride after reaction, controls 3～5min and drip off, after dropping, continue stirring reaction 1～2h；After reaction terminates, it is added thereto to distilled water by reactant liquor volume ratio 3:1, continue stirring reaction 15～20min, reactant liquor in bottle is added macroporous resin adsorption 2～3h, with clear water rinse resin to clarification after adsorption equilibrium, the ethanol every time adding 60～80mL mass fraction 90% in the resin after cleaning resolves, repeated resolution 3～5 times, the desorbed solution rotary evaporation obtained is removed ethanol, regulating desorbed solution pH with mass concentration 25% hydrochloric acid is 3.5～4.0, extract 2～3 times with the mixed liquor of petroleum ether and ethyl acetate volume ratio 5:2 after adjustment, remove fatty acid, by aqueous phase spin concentration 2～3h at 55～60 DEG C, by concentrated solution lyophilization, obtain tea saponin cetylate；Measuring 120～150mL dehydrated alcohol as co-emulsifier, be added thereto to 5～8g ferulic acid, at 40～50 DEG C, ultrasonic dissolution 20～30min obtains ferulic acid solution, standby；Agent by weight, choose 15～30 parts of above-mentioned ferulic acid solution and 20～40 parts of oil phases, 40～50 parts of tea saponin cetylate mixing respectively, high-speed stirred 5～10min under 3000～6000rpm, put in the water bath with thermostatic control of 30～50 DEG C after stirring, being stirred when 1000～1500rpm, stirring is slowly added 60～70 DEG C of hot water, till solution becomes muddiness again from turbid solution change clarification, it is cooled to room temperature, forms ferulic acid microemulsion formulation。
Described oil phase is one of following components: Oleum sesami, Oleum Ricini, Semen Maydis oil, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen。
Example 1
First weigh 2g tea saponin and 5g potassium carbonate loads in 500mL flask, N is being added by solid-to-liquid ratio 1:5 in flask, dinethylformamide, stir to solid dissolving, stirring reaction 20min at 0 DEG C is put in ice-water bath after dissolving, it is slowly added dropwise 5～8mL Hexadecanoyl chloride after reaction, controls 3min and drip off, after dropping, continue stirring reaction 1h；After reaction terminates, it is added thereto to distilled water by reactant liquor volume ratio 3:1, continue stirring reaction 15min, reactant liquor in bottle is added macroporous resin adsorption 2h, with clear water rinse resin to clarification after adsorption equilibrium, the ethanol every time adding 60mL mass fraction 90% in the resin after cleaning resolves, repeated resolution 3 times, the desorbed solution rotary evaporation obtained is removed ethanol, regulating desorbed solution pH with mass concentration 25% hydrochloric acid is 3.5, extract 2 times with the mixed liquor of petroleum ether and ethyl acetate volume ratio 5:2 after adjustment, remove fatty acid, by aqueous phase spin concentration 2h at 55 DEG C, by concentrated solution lyophilization, obtain tea saponin cetylate；Measuring 120mL dehydrated alcohol as co-emulsifier, be added thereto to 5g ferulic acid, at 40 DEG C, ultrasonic dissolution 20min obtains ferulic acid solution, standby；Agent by weight, choose 15 parts of above-mentioned ferulic acid solution and 40 parts of oil phases, 45 parts of tea saponin cetylate mixing respectively, high-speed stirred 5min at 3,000 rpm, put in the water bath with thermostatic control of 30 DEG C after stirring, being stirred when 1000rpm, stirring is slowly added 60 DEG C of hot water, till solution becomes muddiness again from turbid solution change clarification, it is cooled to room temperature, forms ferulic acid microemulsion formulation。
Described oil phase is one of following components: Oleum sesami, Oleum Ricini, Semen Maydis oil, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen。
The microemulsion of the present invention can be made into oral liquid, tablet, capsule, also apply be applicable in injection, lotion, liniment, patch or electuary, oral liquid, tablet, capsule take after under physiological body temperature, gastrointestinal motility effect, meet water or gastro-intestinal Fluid is dispersed into the particle diameter nano level microemulsion particles about 430nm, it is appreciated that in the absorption of human body。
Example 2
First weigh 4g tea saponin and 8g potassium carbonate loads in 500mL flask, N is being added by solid-to-liquid ratio 1:5 in flask, dinethylformamide, stir to solid dissolving, stirring reaction 25min at 3 DEG C is put in ice-water bath after dissolving, it is slowly added dropwise 6mL Hexadecanoyl chloride after reaction, controls 4min and drip off, after dropping, continue stirring reaction 1.5h；After reaction terminates, it is added thereto to distilled water by reactant liquor volume ratio 3:1, continue stirring reaction 17min, reactant liquor in bottle is added macroporous resin adsorption 2.5h, with clear water rinse resin to clarification after adsorption equilibrium, the ethanol every time adding 70mL mass fraction 90% in the resin after cleaning resolves, repeated resolution 4 times, the desorbed solution rotary evaporation obtained is removed ethanol, regulating desorbed solution pH with mass concentration 25% hydrochloric acid is 3.8, extract 2 times with the mixed liquor of petroleum ether and ethyl acetate volume ratio 5:2 after adjustment, remove fatty acid, by aqueous phase spin concentration 2.5h at 57 DEG C, by concentrated solution lyophilization, obtain tea saponin cetylate；Measuring 125mL dehydrated alcohol as co-emulsifier, be added thereto to 6g ferulic acid, at 45 DEG C, ultrasonic dissolution 25min obtains ferulic acid solution, standby；Agent by weight, choose 20 parts of above-mentioned ferulic acid solution and 30 parts of oil phases, 50 parts of tea saponin cetylate mixing respectively, high-speed stirred 8min under 4500rpm, put in the water bath with thermostatic control of 40 DEG C after stirring, being stirred when 1250rpm, stirring is slowly added 65 DEG C of hot water, till solution becomes muddiness again from turbid solution change clarification, it is cooled to room temperature, forms ferulic acid microemulsion formulation。
Described oil phase is one of following components: Oleum sesami, Oleum Ricini, Semen Maydis oil, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen。
The microemulsion of the present invention can be made into oral liquid, tablet, capsule, also apply be applicable in injection, lotion, liniment, patch or electuary, oral liquid, tablet, capsule take after under physiological body temperature, gastrointestinal motility effect, meet water or gastro-intestinal Fluid is dispersed into the particle diameter nano level microemulsion particles about 450nm, it is appreciated that in the absorption of human body。
Example 3
First weigh 5g tea saponin and 12g potassium carbonate loads in 500mL flask, N is being added by solid-to-liquid ratio 1:5 in flask, dinethylformamide, stir to solid dissolving, stirring reaction 30min at 5 DEG C is put in ice-water bath after dissolving, it is slowly added dropwise 8mL Hexadecanoyl chloride after reaction, controls 5min and drip off, after dropping, continue stirring reaction 2h；After reaction terminates, it is added thereto to distilled water by reactant liquor volume ratio 3:1, continue stirring reaction 20min, reactant liquor in bottle is added macroporous resin adsorption 3h, with clear water rinse resin to clarification after adsorption equilibrium, the ethanol every time adding 80mL mass fraction 90% in the resin after cleaning resolves, repeated resolution 5 times, the desorbed solution rotary evaporation obtained is removed ethanol, regulating desorbed solution pH with mass concentration 25% hydrochloric acid is 4.0, extract 3 times with the mixed liquor of petroleum ether and ethyl acetate volume ratio 5:2 after adjustment, remove fatty acid, by aqueous phase spin concentration 3h at 60 DEG C, by concentrated solution lyophilization, obtain tea saponin cetylate；Measuring 150mL dehydrated alcohol as co-emulsifier, be added thereto to 8g ferulic acid, at 50 DEG C, ultrasonic dissolution 30min obtains ferulic acid solution, standby；Agent by weight, choose 30 parts of above-mentioned ferulic acid solution and 30 parts of oil phases, 40 parts of tea saponin cetylate mixing respectively, high-speed stirred 10min under 6000rpm, put in the water bath with thermostatic control of 50 DEG C after stirring, being stirred when 1500rpm, stirring is slowly added 70 DEG C of hot water, till solution becomes muddiness again from turbid solution change clarification, it is cooled to room temperature, forms ferulic acid microemulsion formulation。
Described oil phase is one of following components: Oleum sesami, Oleum Ricini, Semen Maydis oil, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen。
The microemulsion of the present invention can be made into oral liquid, tablet, capsule, also apply be applicable in injection, lotion, liniment, patch or electuary, oral liquid, tablet, capsule take after under physiological body temperature, gastrointestinal motility effect, meet water or gastro-intestinal Fluid is dispersed into the particle diameter nano level microemulsion particles about 460nm, it is appreciated that in the absorption of human body。
Claims (2)
1. the preparation method of a ferulic acid microemulsion formulation, it is characterised in that concrete preparation process is:
(1) weigh 2～5g tea saponin and 5～12g potassium carbonate loads in 500mL flask, N is being added by solid-to-liquid ratio 1:5 in flask, dinethylformamide, stir to solid dissolving, stirring reaction 20～30min at 0～5 DEG C is put in ice-water bath after dissolving, it is slowly added dropwise 5～8mL Hexadecanoyl chloride after reaction, controls 3～5min and drip off, after dropping, continue stirring reaction 1～2h；
(2) after above-mentioned reaction terminates, it is added thereto to distilled water by reactant liquor volume ratio 3:1, continue stirring reaction 15～20min, reactant liquor in bottle is added macroporous resin adsorption 2～3h, with clear water rinse resin to clarification after adsorption equilibrium, the ethanol every time adding 60～80mL mass fraction 90% in the resin after cleaning resolves, repeated resolution 3～5 times, the desorbed solution rotary evaporation obtained is removed ethanol, regulating desorbed solution pH with mass concentration 25% hydrochloric acid is 3.5～4.0, extract 2～3 times with the mixed liquor of petroleum ether and ethyl acetate volume ratio 5:2 after adjustment, remove fatty acid, by aqueous phase spin concentration 2～3h at 55～60 DEG C, by concentrated solution lyophilization, obtain tea saponin cetylate, standby；
(3) measuring 120～150mL dehydrated alcohol as co-emulsifier, be added thereto to 5～8g ferulic acid, at 40～50 DEG C, ultrasonic dissolution 20～30min obtains ferulic acid solution, standby；
(4) agent by weight, choose 15～30 parts of above-mentioned ferulic acid solution and the tea saponin cetylate mixing of 20～40 parts of oil phases, 40～50 parts of steps (3) respectively, high-speed stirred 5～10min under 3000～6000rpm, put in the water bath with thermostatic control of 30～50 DEG C after stirring, being stirred when 1000～1500rpm, stirring is slowly added 60～70 DEG C of hot water, till solution becomes muddiness again from turbid solution change clarification, it is cooled to room temperature, forms ferulic acid microemulsion formulation。
2. the preparation method of a kind of ferulic acid microemulsion formulation according to claim 1, it is characterised in that: described oil phase is one of following components: Oleum sesami, Oleum Ricini, Semen Maydis oil, Oleum Gossypii semen, soybean oil, Oleum Arachidis hypogaeae semen。
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110123755A (en) * | 2019-06-30 | 2019-08-16 | 重庆大学 | A kind of nano oil-in-water emulsion and its preparation method and application based on ferulic acid levamisol salt |
| CN114479034A (en) * | 2021-12-23 | 2022-05-13 | 江苏金隆新材料有限公司 | High-temperature-resistant ferulic acid-based unsaturated resin and preparation method thereof |
| US20220168251A1 (en) * | 2020-12-02 | 2022-06-02 | Nhat Hai New Technology Joint Stock Company | Process for production of a nano-microemulsion system of ferulic |
-
2016
- 2016-03-17 CN CN201610151239.8A patent/CN105687134A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110123755A (en) * | 2019-06-30 | 2019-08-16 | 重庆大学 | A kind of nano oil-in-water emulsion and its preparation method and application based on ferulic acid levamisol salt |
| US20220168251A1 (en) * | 2020-12-02 | 2022-06-02 | Nhat Hai New Technology Joint Stock Company | Process for production of a nano-microemulsion system of ferulic |
| CN114479034A (en) * | 2021-12-23 | 2022-05-13 | 江苏金隆新材料有限公司 | High-temperature-resistant ferulic acid-based unsaturated resin and preparation method thereof |
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