CN108042812A - A kind of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion and preparation method thereof - Google Patents
A kind of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of rhizoma chuanxiong volatile oil hydroxypropyl beta cyclodextrin clathrate, rhizoma chuanxiong volatile oil and hydroxypropyl beta cyclodextrin envelope-bulk to weight ratio are 1 in the inclusion compound:4~1:8, the hydroxypropyl beta cyclodextrin is by by beta cyclodextrin, propylene oxide and deionized water in molar ratio 1:2~3:60~65 carry out etherification reaction in alkaline conditions, and neutralized after reaction, filtering, washing, extracting are made.The special hydroxypropyl beta cyclodextrin solubility of the present invention is high, and its empty size is agreed with rhizoma chuanxiong volatile oil molecular size, it is more easy to include, the utilization rate of rhizoma chuanxiong volatile oil can be improved, inclusion compound recovery rate and inclusion compound oil content, and preparation process is simple for process, etherification time is short, reaction condition is mild, and impurity content is low.Rhizoma chuanxiong volatile oil hydroxypropyl beta cyclodextrin clathrate inclusion essential oil rate rate of the present invention is high, and inclusion effect is good, and inclusion compound high income, and stability is good, organic solvent-free residual.
Description
Technical field
The present invention relates to the field of Chinese medicines, more particularly, to a kind of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion and
Its preparation method.
Background technology
Rhizoma Chuanxiong is Umbelliferae Jehol Ligusticum Rhizome platymiscium, and dry rhizome is one of China's traditional Chinese medicine, is called " the gas in blood
Medicine ", has effects that blood-activating and qi-promoting, wind-expelling pain-stopping, and volatile oil is its important active ingredient.Ligusticumic wood lactone is rhizoma chuanxiong volatile oil
In principle active component and evaluate Rhizoma Chuanxiong quality important indicator, account for the 58% of rhizoma chuanxiong volatile oil.According to research reports,
There is preventive and therapeutic effect to cardiovascular and cerebrovascular diseases such as atherosclerosis, vasculitis and cerebral thrombuss, and have very strong spasmolysis, relieving asthma, town
It is set for using, can be clinically used for treatment bronchitis and gynecological disease.
Since volatile oil has certain volatility, easily scatter and disappear during preparation and storage, influence the stabilization of preparation
Property, and inclusion technique can increase drug solubility, cover drug flavor, therefore in order to improve its utilization rate, prepared by volatile oil
It is one of common method into cyclodextrin inclusion compound.
Beta-cyclodextrin (β-CD) is mostly used in the prior art to be included to volatile oil, but beta-cyclodextrin dissolves in water
Very little is spent, and with certain renal toxicity and hemolytic, limits application range.Hydroxypropyl-β-cyclodextrin (HP- β-CD) be β-
The hydroxypropyl derivatives of cyclodextrin (β-CD), compared with its parent β-CD, not only water solubility is high, to thermostabilization, and to kidney, muscle
It is almost non-stimulated with mucous membrane, it is considered to be a kind of low toxicity, safe and effective water-soluble inclusion material.But existing hydroxypropyl-
Beta-cyclodextrin is for including rhizoma chuanxiong volatile oil, and inclusion rate is not high, and rhizoma chuanxiong volatile oil utilization rate is low, and stability is bad, and prepares
Journey is cumbersome, is unfavorable for mass producing.
The content of the invention
The defects of the purpose of the present invention is overcoming the prior art, a kind of rhizoma chuanxiong volatile oil utilization rate height is provided, inclusion compound returns
The strong rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion of high income, stability, and its preparation method is easy to operate, during preparation
Between it is short, heavy industrialization quantity-produced needs can be met
To achieve these goals, the present invention provides a kind of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion, the inclusion
Rhizoma chuanxiong volatile oil and hydroxypropyl-β-cyclodextrin envelope-bulk to weight ratio are 1 in object:4~1:8, the hydroxypropyl-β-cyclodextrin is logical
Cross what following methods obtained：
By beta-cyclodextrin, propylene oxide and deionized water in molar ratio 1:2~3:60~65 carry out ether in alkaline conditions
Change reaction, neutralized after reaction, filtering, washing, extracting are made.
It is preferred that rhizoma chuanxiong volatile oil and hydroxypropyl-β-cyclodextrin envelope-bulk to weight ratio are 1 in above-mentioned inclusion compound:8.
Preferred volume weight ratio of the present invention is ml:g.
The reaction temperature of above-mentioned etherification reaction is 65~70 DEG C, and pressure is 1~2MPa, 1~3h of reaction time.
Above-mentioned etherification reaction neutral and alkali condition is addition lithium hydroxide, sodium hydroxide or ammonium hydroxide.
Rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion of the present invention, is prepared by the following method to obtain：
(1) hydroxypropyl-β-cyclodextrin is taken to be put into reaction vessel, be dissolved in water, put in constant temperature blender with magnetic force, with
1000-1200r·min-1Speed stirs, and adds in rhizoma chuanxiong volatile oil, and constant temperature is stirring while adding to setting time, obtain hydroxy propyl-Beta-
Cyclodextrin encapsulated liquid；
(2) hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (1) for 24 hours, is filtered, respectively with distilled water and anhydrous
Ethyl alcohol washing filters product, until color is pure white, non-volatile oil gas taste, vacuum drying 3-5h to obtain the final product.
The temperature that constant temperature stirs in above-mentioned steps (1) is set as 45-55 DEG C, and the time is set as 1.5-2.5h；Preferable temperature
For 50 DEG C, the preferably time is 2h.
The preparation method of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion of the present invention, specifically includes following step
Suddenly：
(1) by beta-cyclodextrin, propylene oxide and deionized water in molar ratio 1:2~3:60~65 carry out in alkaline conditions
Hydroxy propyl-Beta-cyclodextrin is made in etherification reaction, neutralized after reaction, filtering, washing, extracting.
(2) hydroxypropyl-β-cyclodextrin is taken to be put into reaction vessel, be dissolved in water, put in constant temperature blender with magnetic force, with
1000-1200r·min-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil, constant temperature is stirring while adding to setting time, obtains hydroxypropyl
Group-beta-cyclodextrin includes liquid；
(3) hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (2) for 24 hours, is filtered, respectively with distilled water and anhydrous
Ethyl alcohol washing filters product, until color is pure white, non-volatile oil gas taste, vacuum drying 3-5h to obtain the final product.
In above-mentioned steps (1) reaction temperature of etherification reaction be 65~70 DEG C, pressure be 1~2MPa, the reaction time 1~
3h, alkaline condition are addition lithium hydroxide, sodium hydroxide or ammonium hydroxide.
The temperature that constant temperature stirs in above-mentioned steps (2) is set as 45-55 DEG C, and the time is set as 1.5-2.5h；Preferable temperature
For 50 DEG C, the preferably time is 2h.
Compared with prior art, beneficial effects of the present invention are：
(1) the special hydroxypropyl-β-cyclodextrin solubility of the present invention is high, and its empty size and rhizoma chuanxiong volatile oil molecule are big
It is small to agree with, it is more easy to include, the utilization rate of rhizoma chuanxiong volatile oil, inclusion compound recovery rate and inclusion compound oil content can be improved, and prepared
Process is simple, and etherification time is short, and reaction condition is mild, and impurity content is low.
(2) rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion inclusion essential oil rate rate of the present invention is high, inclusion effect
Fruit is good, and inclusion compound high income, and stability is good, organic solvent-free residual.
(3) preparation process of the invention is simple, short preparation period, favorable reproducibility.
(4) material therefor of the present invention is simple and easy to get, and stock utilization is high, reduces cost.
Specific embodiment
The preferred embodiment of the present invention is more fully described below with reference to specific embodiment.
Embodiment 1
A kind of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion, its preparation method be,
(1) by beta-cyclodextrin, propylene oxide and deionized water in molar ratio 1:2:In 60 input autoclaves, while add in few
It measures lithium hydroxide and carries out etherification reaction, reaction temperature passes through after reaction for 65 DEG C, pressure 1.0MPa, reaction time 1.5h
It neutralizes, filter, ethyl alcohol washs, hydroxypropyl-β-cyclodextrin is made in acetone extraction separation.
(2) 8g hydroxypropyl-β-cyclodextrins is taken to be put into reaction vessel, are dissolved in water, are put in constant temperature blender with magnetic force, with
1000r·min-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil 1ml, 50 DEG C of constant temperature, 2h stirring while adding obtains rhizoma chuanxiong volatile oil
Hydroxypropyl-β-cyclodextrin includes liquid；
(3) rhizoma chuanxiong volatile oil hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (2) for 24 hours, is filtered, uses steam respectively
Distilled water and absolute ethyl alcohol washing filter product, until color is pure white, non-volatile oil gas taste, 40 DEG C of vacuum drying 3.5h to obtain the final product.
Embodiment 2
A kind of preparation method of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion,
(1) by beta-cyclodextrin, propylene oxide and deionized water in molar ratio 1:3:In 65 input autoclaves, while add in few
It measures sodium hydroxide and carries out etherification reaction, reaction temperature passes through after reaction for 65 DEG C, pressure 1.5MPa, reaction time 1.5h
It neutralizes, filter, ethyl alcohol washs, hydroxypropyl-β-cyclodextrin is made in acetone extraction separation.
(2) 7g hydroxypropyl-β-cyclodextrins is taken to be put into reaction vessel, are dissolved in water, are put in constant temperature blender with magnetic force, with
1000r·min-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil 1ml, 48 DEG C of constant temperature, and 2.5h stirring while adding obtains Rhizoma Chuanxiong volatilization
Oily hydroxypropyl-β-cyclodextrin includes liquid；
(3) rhizoma chuanxiong volatile oil hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (2) for 24 hours, is filtered, uses steam respectively
Distilled water and absolute ethyl alcohol washing filter product, until color is pure white, non-volatile oil gas taste, 40 DEG C of vacuum drying 4h to obtain the final product.
Comparative example 1
(1) 8g hydroxypropyl-β-cyclodextrins (commercially available) is taken to be put into reaction vessel, is dissolved in water, puts constant temperature blender with magnetic force
On, with 1000rmin-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil 1ml, 50 DEG C of constant temperature, 2h stirring while adding obtains Rhizoma Chuanxiong
Volatile oil hydroxypropyl-β-cyclodextrin includes liquid；
(2) rhizoma chuanxiong volatile oil hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (1) for 24 hours, is filtered, uses steam respectively
Distilled water and absolute ethyl alcohol washing filter product, until color is pure white, non-volatile oil gas taste, 40 DEG C of vacuum drying 3.5h to obtain the final product.
Comparative example 2
(1) by beta-cyclodextrin, propylene oxide and deionized water in molar ratio 1:5:In 80 input autoclaves, while add in few
It measures sodium hydroxide and carries out etherification reaction, reaction temperature is 80 DEG C, pressure 0.5MPa, reaction time 1h, in passing through after reaction
It separates and hydroxypropyl-β-cyclodextrin is made with filtering, ethyl alcohol washing, acetone extraction.
(2) 15g hydroxypropyl-β-cyclodextrins is taken to be put into reaction vessel, are dissolved in water, are put in constant temperature blender with magnetic force, with
700r·min-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil 1ml, 40 DEG C of constant temperature, 5h stirring while adding obtains rhizoma chuanxiong volatile oil hydroxyl
Propyl-beta-cyclodextrin includes liquid；
(3) rhizoma chuanxiong volatile oil hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (2) for 24 hours, is filtered, uses steam respectively
Distilled water and absolute ethyl alcohol washing filter product, until color is pure white, non-volatile oil gas taste, 40 DEG C of vacuum drying 4h to obtain the final product.
Comparative example 3
(1) 8g beta-cyclodextrins (commercially available) is taken to be put into reaction vessel, is dissolved in water, puts in constant temperature blender with magnetic force, with
1000r·min-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil 1ml, 50 DEG C of constant temperature, 2h stirring while adding obtains rhizoma chuanxiong volatile oil
Hydroxypropyl-β-cyclodextrin includes liquid；
(2) rhizoma chuanxiong volatile oil hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (1) for 24 hours, is filtered, uses steam respectively
Distilled water and absolute ethyl alcohol washing filter product, until color is pure white, non-volatile oil gas taste, 40 DEG C of vacuum drying 4h to obtain the final product.
Inclusion compound testing result is shown in Table 1 made from above-described embodiment and comparative example.
Inclusion compound made from 1 embodiment of the present invention of table and comparative example compares
| Inclusion essential oil rate | Inclusion compound recovery rate | Inclusion compound oil content | |
| Embodiment 1 | 97.86 | 91.36 | 89.78 |
| Embodiment 2 | 97.05 | 90.79 | 86.52 |
| Comparative example 1 | 90.72 | 83.94 | 81.63 |
| Comparative example 2 | 91.94 | 84.75 | 82.47 |
| Comparative example 3 | 90.48 | 81.89 | 76.58 |
Note：For volatile oil utilization rate to weigh the important indicator of inclusion effect, volatile oil utilization rate is higher, and inclusion effect is got over
It is good, but inclusion compound yield also has a certain impact in production.Calculation formula is as follows：
Volatilize oil quality/volatile oil input quality × 100% in inclusion essential oil rate (%)=inclusion compound
Inclusion compound recovery rate (%)=inclusion amount of substance/(β-CD add in quality+volatile oil and add in quality) × 100%
Volatilize oil quality/inclusion amount of substance × 100% in inclusion compound oil content (%)=inclusion compound
Inclusion compound yield and inclusion rate assay method：
It presses《Chinese Pharmacopoeia》Version (one) annex determination of volatile oil method carries out within 2015.By the accurate title of gained drying inclusion compound
Weight, puts in the round-bottomed flask equipped with zeolite, adds distilled water about 300mL, connects volatile oil determination apparatus, and slightly boiling simultaneously keeps 5h, until oil
Stop heating when amount is not further added by, place 30min, reading obtains volatilization oil volume.
Claims (10)
1. a kind of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion, it is characterised in that rhizoma chuanxiong volatile oil and hydroxyl in the inclusion compound
Propyl-beta-cyclodextrin envelope-bulk to weight ratio is 1:4~1:8, the hydroxypropyl-β-cyclodextrin obtains by the following method：
By beta-cyclodextrin, propylene oxide and deionized water in molar ratio 1:2~3:60~65 carry out being etherified instead in alkaline conditions
Should, neutralized after reaction, filtering, washing, extracting are made.
2. rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that in the inclusion compound
Rhizoma chuanxiong volatile oil is 1 with hydroxypropyl-β-cyclodextrin envelope-bulk to weight ratio:8.
3. rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that etherification reaction
Reaction temperature is 65~70 DEG C, and pressure is 1~2MPa, 1~3h of reaction time.
4. rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that the alkalescence
Condition is addition lithium hydroxide, sodium hydroxide or ammonium hydroxide.
5. rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 1, it is characterised in that the inclusion compound is
It is prepared by the following method：
(1) hydroxypropyl-β-cyclodextrin is taken to be put into reaction vessel, be dissolved in water, put in constant temperature blender with magnetic force, with 1000r
min-1Speed stirs, and adds in rhizoma chuanxiong volatile oil, constant temperature is stirring while adding to setting time, obtains rhizoma chuanxiong volatile oil hydroxy propyl-Beta-ring
Dextrin includes liquid；
(2) hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (1) for 24 hours, is filtered, respectively with distilled water and absolute ethyl alcohol
Washing filters product, until color is pure white, non-volatile oil gas taste, vacuum drying 3-5h to obtain the final product.
6. rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 5, it is characterised in that in step (1)
The temperature of constant temperature stirring is set as 45-55 DEG C, and the time is set as 1.5-2.5h.
7. rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 5, it is characterised in that in step (1)
The temperature of constant temperature stirring is set as 50 DEG C, and the time is set as 2h.
8. the rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion described in any one claim in claim 1-7
Preparation method, it is characterised in that comprise the following steps：
(1) hydroxypropyl-β-cyclodextrin is taken to be put into reaction vessel, be dissolved in water, put in constant temperature blender with magnetic force, with 1000-
1200r·min-1Speed stirs, and is slowly added to rhizoma chuanxiong volatile oil, constant temperature is stirring while adding to setting time, obtains rhizoma chuanxiong volatile oil
Hydroxypropyl-β-cyclodextrin includes liquid；
(2) hydroxypropyl-β-cyclodextrin inclusion liquid refrigeration obtained by step (1) for 24 hours, is filtered, respectively with distilled water and absolute ethyl alcohol
Washing filters product, until color is pure white, non-volatile oil gas taste, vacuum drying 3-5h to obtain the final product.
9. the preparation method of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 8, it is characterised in that
The temperature that constant temperature stirs in step (1) is set as 45-55 DEG C, and the time is set as 1.5-2.5h.
10. the preparation method of rhizoma chuanxiong volatile oil hydroxypropyl-beta-cyclodextrin inclusion according to claim 8, feature exist
The temperature that constant temperature stirs in step (1) is set as 50 DEG C, and the time is set as 2h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113144220A (en) * | 2021-04-30 | 2021-07-23 | 中国药科大学 | Beta-cyclodextrin inclusion compound, gel preparation, preparation method and application thereof |
| CN113289032A (en) * | 2021-06-02 | 2021-08-24 | 京津冀联创药物研究（北京）有限公司 | Cyclodextrin oil inclusion compound and preparation method thereof |
| CN113481726A (en) * | 2021-07-28 | 2021-10-08 | 爱慕股份有限公司 | Preparation method of botanical anti-mosquito textile fabric |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113144220A (en) * | 2021-04-30 | 2021-07-23 | 中国药科大学 | Beta-cyclodextrin inclusion compound, gel preparation, preparation method and application thereof |
| CN113289032A (en) * | 2021-06-02 | 2021-08-24 | 京津冀联创药物研究（北京）有限公司 | Cyclodextrin oil inclusion compound and preparation method thereof |
| CN113481726A (en) * | 2021-07-28 | 2021-10-08 | 爱慕股份有限公司 | Preparation method of botanical anti-mosquito textile fabric |
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Application publication date: 20180518 |