CN110305180A - A kind of preparation process extracting high-purity ursolic acid from rosemary - Google Patents
A kind of preparation process extracting high-purity ursolic acid from rosemary Download PDFInfo
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- CN110305180A CN110305180A CN201910609698.XA CN201910609698A CN110305180A CN 110305180 A CN110305180 A CN 110305180A CN 201910609698 A CN201910609698 A CN 201910609698A CN 110305180 A CN110305180 A CN 110305180A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Abstract
The invention proposes a kind of from rosemary extracts the preparation process of high-purity ursolic acid, it is extracted by using different solvents, it is separated by filtration crystallization and purification, obtain black bearberry acid product of the purity 99% or more, the black bearberry acid product and content 20%-40% carnosic acid product of content 5%-20%, 40%-60% and 50-70% can also be obtained simultaneously.The preparation process raw material availability disclosed by the invention for extracting high-purity ursolic acid is high, and solvent repetitive cycling uses, and environmental pollution is small, industrialized production easy to accomplish.
Description
Technical field
The present invention relates to plant product processing technique fields, in particular to a kind of that high-purity ursolic acid is extracted from rosemary
Preparation process.
Background technique
Rosemary, Labiatae shrub, property like temperature climate, originate in the northern Mediterranean of European Region and Africa, far away from
Caowei Kingdom just once introduces a fine variety China period, occasionally has application in present gardens.Can extract from the flower and leaf of rosemary has excellent resist
The antioxidant and Rosemary Oil of oxidisability.Rosemary antioxidant is widely used in medicine, fried food, rich oil food and each
The fresh-keeping of quasi-grease is guaranteed the quality；And to be then used for fragrance, air freshener, driving ants and sterilization, desinsection etc. daily for rosemary essence
Chemical industry.Rosemary is a kind of rare natural perfume plant, the season of growth can distribute a kind of faint scent, has to clear away heart-fire and refresh oneself
Effect.Its stem, leaf and flower has pleasant fragrance, and the aromatic oil that colored and spray extracts can be used for deploying air freshener, perfume (or spice)
The cosmetic materials such as water, perfumed soap, most notable toner make of rosemary, and can be in beverage, skin care oil, hair tonic
It is used in agent, washing cream.There are the antioxygens such as carnosic acid, carnosol, rosmanol, ursolic acid, Rosmarinic acid in rosemary
Chemical conversion point.
Ursolic acid resource is wide, and toxicity is low, have extensive bioactivity, especially anticancer, it is antitumor, anti-oxidant, anti-inflammatory,
Effect in terms of liver protection, reducing blood lipid is significant, significant.Discovered in recent years, ursolic acid not only to it is a variety of it is carcinogenic, promote cancer objects have to
Anti- effect, and the growth of Several Kinds of Malignancy cell can be inhibited.Meanwhile ursolic acid and its derivative also have inhibition to virus
Activity.Therefore, the pharmacological activity of ursolic acid increasingly causes the concern of drug brainstrust.It is studied recently as to ursolic acid
Deepen continuously so that it starts to be widely used in clinic.
Rosemary extracts in industry and prepares that high-content ursolic acid Product Process is few, and industrialized production mostly uses greatly at present
Hole resin adsorption partition method, production low efficiency, environmental pollution is serious.And simple pass through solvent extraction, displacement, recrystallization
Technique, it is difficult to obtain 90% black bearberry acid product.
Summary of the invention
Mirror is a kind of from fan to obtain with acid-base reagent it is an object of the invention to mainly be replaced and assisted by solvent with this
The preparation process of high-purity ursolic acid is repeatedly extracted in perfume.
It is of the present invention to be achieved in that
A kind of preparation process extracting high-purity ursolic acid from rosemary, comprising the following steps:
Step 1: choosing rosemary and pass through the Rosmarinus officinalis extract that ethanol extraction process obtains in industrialized production, be added
5-10 times of Rosmarinus officinalis extract powder measures 65%-75% ethanol solution, and heating extraction filters while hot, and gained filter residue is by above-mentioned heavy
It is multiple to extract for several times, obtain primary fat-soluble Rosmarinus officinalis extract filter residue A；
Step 2: step 1 gained filtrate being merged, is concentrated under reduced pressure, obtains medicinal extract, it is 20%- that content is obtained after washing is dry
40% carnosic acid product；
Step 3: take step 1 gained filter residue A, be added to 10-15 times and measure in 85% ethyl alcohol, be added aqueous slkali, adjust PH to
11-14, stirring and dissolving 20-30min, after microwave treatment, filtering discards filter residue, and acid solution is added in filtrate, adjust pH value to
2-4, room temperature stand 1-2h, filter again, are filter residue B by gained filter residue and drying；
Step 4: step 3 gained filtrate decompression being concentrated, medicinal extract is obtained, is filtered, and adds water washing to neutrality filter residue, is done
It is dry, obtain the low content black bearberry acid product that content is 5%-20%；
Step 5: the petroleum ether or n-hexane that step 3 gained filter residue B is measured with 10-20 times are extracted for several times, are filtered, filter residue
It spontaneously dries or recycling design is dry, be filter residue C；
Step 6: step 5 gained filter residue C addition being measured into acetic acid for 10-15 times, dissolves by heating, filters while hot, by gained filter residue
Drying is washed, the black bearberry acid product that content is 50%-70% is obtained；
Step 7: step 6 gained filtrate natural cooling being stood still for crystals, is filtered；
Step 8: step 7 gained filter residue being repeated several times according to step 7, last time filter residue ethyl alcohol and moisture step are washed
It washs, it is dry, obtain filter residue D；
Step 9: by step 8 gained filter residue D, water is measured with 5-10 times and is dissolved, addition NaOH solution adjusting pH value to 11-14,
Stirring and dissolving filters after microwave treatment, discards filter residue；
Step 10, step 9 gained filtrate is concentrated, and starts to stop concentration immediately after there is crystallization, potassium salt soln is added, stirs
It mixes, filters, obtain filter residue, be washed with water, obtain filter residue E after dry；
Step 11: step 10 gained filter residue E being added to 10-15 times and is measured in acetic acid solution, is filtered, gained filtrate stands knot
Crystalline substance, filtering gained filter residue repeat this step for several times, and drying, as the high-purity black bearberry is washed with water in the filter residue finally obtained
Acid, purity is 99% or more.
Further, the filtrate solvent recycling in the step 2, step 4, step 5 and step 7；Step 2 and step 4 are returned
Etoh solvent is harvested to obtain, step 5 recycling obtains solvent petroleum ether or n-hexane, and step 7 recycling design obtains acetic acid, step 9
Recycling design obtains acetic acid.
Further, in the step 1, Extracting temperature is 65-80 DEG C, extraction time 45min-60min.
Further, in the step 3 and step 9, Microwave Extraction condition is microwave power 100-140W, extraction time 5-
10min；The aqueous slkali is NaOH solution.
Further, in the step 3, the acid solution is phosphoric acid or hydrochloric acid or two kinds of sour mixtures.
Further, in the step 5, the Extracting temperature of petroleum ether or n-hexane is 65-75 DEG C, and each extraction time is
45-60min。
Further, in the step 6, the temperature of solution is 70-80 DEG C, dissolution time 30min-45min.
Further, in the step 6, the acetic acid can be replaced methanol, ethyl alcohol, butanol, ethyl acetate, acetic acid third
Ester or butyl acetate.
Further, in the step 10, the potassium salt soln is the saturated solution of potassium chloride, potassium sulfate.
Further, in the step 11, the black bearberry acid product of gained high-purity, the mass fraction of ursolic acid 99% with
On.
Compared with prior art, the invention has the benefit that
1) purity is high of ursolic acid obtained by the application, content is 99% or more；
2) the application can also obtain the black bearberry acid product of content 5%-20%, 40%-60% and 50-70% simultaneously, with
And content 20%-40% carnosic acid product；
3) the application technical process is easy, extracts yield height, and yield is big, and utilization rate of active components is high, it is easy to accomplish industry
Change and produce in batches, and the safety of product is good；
4) the application solvent recoverable, production cost is low, and generation dangerous waste is few, and environmental pollution is small.
Specific embodiment
For the technical solution in the present invention is clearly and completely described in conjunction with the embodiments, it is clear that inventor says
It is bright, but it is only a part of the embodiment of the present invention that following embodiment is described, instead of all the embodiments.Based on the present invention
In embodiment, every other implementation obtained by those of ordinary skill in the art without making creative efforts
Example, shall fall within the protection scope of the present invention.
A kind of preparation process extracting high-purity ursolic acid from rosemary, comprising the following steps:
Step 1: choosing rosemary and pass through the Rosmarinus officinalis extract that ethanol extraction process obtains in industrialized production, be added
5-10 times of Rosmarinus officinalis extract powder measures 65%-75% ethanol solution, and heating extraction filters while hot, and gained filter residue is by above-mentioned heavy
It is multiple to extract for several times, obtain primary fat-soluble Rosmarinus officinalis extract filter residue A；
Step 2: step 1 gained filtrate being merged, is concentrated under reduced pressure, obtains medicinal extract, it is 20%- that content is obtained after washing is dry
40% carnosic acid product；
Step 3: take step 1 gained filter residue A, be added to 10-15 times and measure in 85% ethyl alcohol, be added aqueous slkali, adjust PH to
11-14, stirring and dissolving 20-30min, after microwave treatment, filtering discards filter residue, and acid solution is added in filtrate, adjust pH value to
2-4, room temperature stand 1-2h, filter again, are filter residue B by gained filter residue and drying；
Step 4: step 3 gained filtrate decompression being concentrated, medicinal extract is obtained, is filtered, and adds water washing to neutrality filter residue, is done
It is dry, obtain the low content black bearberry acid product that content is 5%-20%；
Step 5: the petroleum ether or n-hexane that step 3 gained filter residue B is measured with 10-20 times are extracted for several times, are filtered, filter residue
It spontaneously dries or recycling design is dry, be filter residue C；
Step 6: step 5 gained filter residue C addition being measured into acetic acid for 10-15 times, dissolves by heating, filters while hot, by gained filter residue
Drying is washed, the black bearberry acid product that content is 50%-70% is obtained；
Step 7: step 6 gained filtrate natural cooling being stood still for crystals, is filtered；
Step 8: step 7 gained filter residue being repeated several times according to step 7, last time filter residue ethyl alcohol and moisture step are washed
It washs, it is dry, obtain filter residue D；
Step 9: by step 8 gained filter residue D, water is measured with 5-10 times and is dissolved, addition NaOH solution adjusting pH value to 11-14,
Stirring and dissolving filters after microwave treatment, discards filter residue；
Step 10, step 9 gained filtrate is concentrated, and starts to stop concentration immediately after there is crystallization, potassium salt soln is added, stirs
It mixes, filters, obtain filter residue, be washed with water, obtain filter residue E after dry；
Step 11: step 10 gained filter residue E being added to 10-15 times and is measured in acetic acid solution, is filtered, gained filtrate stands knot
Crystalline substance, filtering gained filter residue repeat this step for several times, and drying, as the high-purity black bearberry is washed with water in the filter residue finally obtained
Acid, purity is 99% or more.
Further, the filtrate solvent recycling in the step 2, step 4, step 5 and step 7；Step 2 and step 4 are returned
Etoh solvent is harvested to obtain, step 5 recycling obtains solvent petroleum ether or n-hexane, and step 7 recycling design obtains acetic acid, step 9
Recycling design obtains acetic acid.
Further, in the step 1, Extracting temperature is 65-80 DEG C, extraction time 45min-60min.
Further, in the step 3 and step 9, Microwave Extraction condition is microwave power 100-140W, extraction time 5-
10min；The aqueous slkali is NaOH solution.
Further, in the step 3, the acid solution is phosphoric acid or hydrochloric acid or two kinds of sour mixtures.
Further, in the step 5, the Extracting temperature of petroleum ether or n-hexane is 65-75 DEG C, and each extraction time is
45-60min。
Further, in the step 6, the temperature of solution is 70-80 DEG C, dissolution time 30min-45min.
Further, in the step 6, the acetic acid can be replaced methanol, ethyl alcohol, butanol, ethyl acetate, acetic acid third
Ester or butyl acetate.
Further, in the step 10, the potassium salt soln is the saturated solution of potassium chloride, potassium sulfate.
According to method made above, the parameter in conjunction with shown in table 1-2 prepares embodiment 1-4, comparative example 1-4.
Table 1:
Table 2:
Comparative example 5:
Lack step 1-2, directly adopt the extraction of 85% ethyl alcohol, remaining step is prepared according to embodiment 3.
Comparative example 6:
Lack step 3, do not have to acid-base method separating and removing impurities, remaining is prepared according to embodiment 3.
Comparative example 7:
Lack step 9-10, after step 8 obtains ursolic acid crude product, direct repeated recrystallize, remaining is according to embodiment 3
Preparation.
Comparative example 8:
Lack microwave treatment, remaining is prepared according to embodiment 3.
As a result as shown in table 3-4, wherein extracted amount is every 100g raw material finished product acquisition amount.
Table 3:
| Unit | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Comparative example 1 | Comparative example 2 | |
| Black bearberry acid concentration | % | 99.2 | 99.5 | 99.7 | 99.4 | 95.2 | 94.8 |
| Extracted amount | g | 5.46 | 5.73 | 5.94 | 5.80 | 5.13 | 4.51 |
Table 4:
| Unit | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 | |
| Black bearberry acid concentration | % | 93.1 | 92.1 | 87.6 | 86.4 | 91.2 | 94.3 |
| Extracted amount | g | 4.28 | 4.16 | 4.09 | 3.74 | 4.25 | 4.63 |
As can be seen that resulting ursolic acid purity is 99% or more according to the given preparation method of the application.Beyond the application
Given method then will affect the purity of final products.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of preparation process for extracting high-purity ursolic acid from rosemary, which comprises the following steps:
Step 1: choosing rosemary and pass through the Rosmarinus officinalis extract that ethanol extraction process obtains in industrialized production, fan is added and changes
5-10 times of fragrant extract powder measures 65%-75% ethanol solution, and heating extraction filters while hot, and gained filter residue is mentioned by above-mentioned repetition
Access time obtains primary fat-soluble Rosmarinus officinalis extract filter residue A；
Step 2: step 1 gained filtrate being merged, is concentrated under reduced pressure, obtains medicinal extract, it is 20%-40% that content is obtained after washing is dry
Carnosic acid product；
Step 3: taking step 1 gained filter residue A, be added to 10-15 times and measure in 85% ethyl alcohol, aqueous slkali is added, adjust PH to 11-
14, stirring and dissolving 20-30min, after microwave treatment, filtering discards filter residue, and acid solution is added in filtrate, adjusts pH value to 2-
4, room temperature stands 1-2h, filters again, is filter residue B by gained filter residue and drying；
Step 4: step 3 gained filtrate decompression is concentrated, medicinal extract is obtained, is filtered, and adds water washing to neutrality filter residue, it is dry,
Obtain the low content black bearberry acid product that content is 5%-20%；
Step 5: the petroleum ether or n-hexane that step 3 gained filter residue B is measured with 10-20 times are extracted for several times, are filtered, and filter residue is natural
Dry or recycling design is dry, is filter residue C；
Step 6: step 5 gained filter residue C addition being measured into acetic acid for 10-15 times, dissolves by heating, filters while hot, by gained residue washing
It is dry, obtain the black bearberry acid product that content is 50%-70%；
Step 7: step 6 gained filtrate natural cooling being stood still for crystals, is filtered；
Step 8: step 7 gained filter residue being repeated several times according to step 7, last time filter residue ethyl alcohol and moisture step washing are done
It is dry, obtain filter residue D；
Step 9: by step 8 gained filter residue D, measuring water dissolution with 5-10 times, NaOH solution is added and adjusts pH value to 11-14, stirring
It dissolves, is filtered after microwave treatment, discard filter residue；
Step 10, step 9 gained filtrate is concentrated, and starts to stop concentration immediately after there is crystallization, potassium salt soln, stirring, mistake is added
Filter, obtains filter residue, is washed with water, and obtains filter residue E after dry；
Step 11: step 10 gained filter residue E is added to 10-15 times and is measured in acetic acid solution, is filtered, gained filtrate stands still for crystals,
Filtering gained filter residue repeats this step for several times, and drying, the as high-purity ursolic acid is washed with water in the filter residue finally obtained,
Purity is 99% or more.
2. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
Filtrate solvent recycling in step 2, step 4, step 5 and step 7；Step 2 and step 4 recycling obtain etoh solvent, and step 5 is returned
Solvent petroleum ether or n-hexane are harvested to obtain, step 7 recycling design obtains acetic acid, and step 9 recycling design obtains acetic acid.
3. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 1, Extracting temperature is 65-80 DEG C, extraction time 45min-60min.
4. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 3 and step 9, Microwave Extraction condition is microwave power 100-140W, extraction time 5-10min；The aqueous slkali is
NaOH solution.
5. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 3, the acid solution is phosphoric acid or hydrochloric acid or two kinds of sour mixtures.
6. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 5, the Extracting temperature of petroleum ether or n-hexane is 65-75 DEG C, and each extraction time is 45-60min.
7. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 6, the temperature of solution is 70-80 DEG C, dissolution time 30min-45min.
8. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 6, the acetic acid can be replaced methanol, ethyl alcohol, butanol, ethyl acetate, propyl acetate or butyl acetate.
9. the preparation process according to claim 1 for extracting high-purity ursolic acid from rosemary, which is characterized in that described
In step 10, the potassium salt soln is the saturated solution of potassium chloride, potassium sulfate.
10. the preparation process of high-purity ursolic acid according to claim 1, which is characterized in that in the step 11, gained is high
The black bearberry acid product of purity, the mass fraction of ursolic acid is 99% or more.
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Cited By (2)
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| CN114907206A (en) * | 2022-06-23 | 2022-08-16 | 海南舒普生物科技有限公司 | Preparation method of high-content water-soluble carnosic acid powder product |
| CN114907206B (en) * | 2022-06-23 | 2024-05-14 | 海南舒普生物科技有限公司 | Preparation method of high-content water-soluble carnosic acid powder product |
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