CN110283077A - A kind of preparation process extracting high-purity Rosmarinic acid from rosemary - Google Patents
A kind of preparation process extracting high-purity Rosmarinic acid from rosemary Download PDFInfo
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- CN110283077A CN110283077A CN201910609696.0A CN201910609696A CN110283077A CN 110283077 A CN110283077 A CN 110283077A CN 201910609696 A CN201910609696 A CN 201910609696A CN 110283077 A CN110283077 A CN 110283077A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention proposes a kind of from rosemary extracts the preparation process of high-purity Rosmarinic acid, extracted by ethyl alcohol, acid condition filtering, transformation solvent, sylvite saturation are precipitated, acidification and repeated recrystallize, obtained Rosmarinic acid of the purity 99% or more.Preparation method technical process described herein is easy, extracts yield height, and yield is big, and utilization rate of active components is high, it is easily industrialized and produces in batches, Product Safety is good, solvent recoverable used in preparation process, production cost is low, and generation dangerous waste is few, and environmental pollution is small.
Description
Technical field
The present invention relates to plant component extraction technical field, in particular to one kind extracts high-purity rosemary from rosemary
The preparation process of acid.
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.
Rosmarinic acid (Rosmarinicacid, abbreviation RosA) is isolated one kind from Lamiaceae plant rosemary
Water-soluble natural phenolic acid class compound, be distributed it is relatively broad, be primarily present in Labiatae, Boraginaceae, Curcurbitaceae, Tiliaceae,
In umbelliferous various plants, especially with content highest in Chun Xing section and comfrey.Rosmarinic acid is a kind of natural anti-oxidation
Agent has stronger antioxidant activity, and antioxidant activity is better than vitamin E, caffeic acid, chlorogenic acid, and folic acid etc. helps to prevent
Only cell damage caused by free radical, therefore reduce the risk of cancer and artery sclerosis.Rosmarinic acid has stronger anti-inflammatory
Activity, while Rosmarinic acid also has antibacterial, the activity of antiviral and antitumor, and have and inhibit acute and chronic infection, uvioresistant
Line, the additive for inhibiting the characteristics such as elastin degradation that Rosmarinic acid has been made to become cosmetics.Currently, Rosmarinic acid pharmacy,
Its important application value has been embodied in the fields such as food, cosmetics.
Rosemary extracts in industry and prepares that high-content Rosmarinic acid Product Process is few, and industrialized production mostly uses at present
Macroporous resin adsorption partition method, production low efficiency, environmental pollution is serious.And it is simple by solvent extraction, displacement, again tie
Brilliant technique, it is difficult to obtain high-purity Rosmarinic acid product.
Summary of the invention
For mirror with this, it is an object of the invention to propose a kind of preparation work that high-purity Rosmarinic acid is extracted from rosemary
Skill.
The preparation process of the present invention that high-purity Rosmarinic acid is extracted from rosemary is achieved in that
A kind of preparation process extracting high-purity Rosmarinic acid from rosemary, comprising the following steps:
Step 1: choosing rosemary cured leaf, ethanol solution is added, extract twice, merge into extracting solution A；
Step 2: the extracting solution A that step 1 is obtained is concentrated under reduced pressure, the medicinal extract of acquisition, filtering, collects filtrate, and with filter
For liquid with the water washing filter residue of equimultiple, it is extracting solution B that washing water merges with filter liquor；
Step 3: in step 2 gained extracting solution B, acid solution is added, alkali tune PH is stood；
Step 4: step 3 acquired solution being filtered, precipitate is separated, obtains extracting solution C；
Step 5: obtaining extracting solution C and n-butanol, extraction is added, stratification releases water phase, and extract liquor is depressurized dense
Contracting, cooling and standings obtain precipitate A.
Step 6: step 5 gained precipitate A is added in KOH solution, the sylvite saturated solution of heat is configured, adjusts PH, it will
Solution is cooling, crystallizes, and filters, and washing obtains precipitate B；
Step 7: step 6 gained precipitate B being added in ethanol solution, acid solution is then added, is dissolved by heating, is adjusted
PH, cooling and standings recrystallization, obtains precipitate C；
Step 8: step 7 gained precipitate C is added in ethyl alcohol, is dissolved by heating, filtering, and filtrate cooling and standings is taken to tie again
Crystalline substance, and will be repeated several times, obtain precipitate D；
Step 9: step 8 gained precipitate D is added into water, is dissolved by heating, cooling and standings recrystallization, and will be repeated several times, institute
Obtaining crystal is resulting high-purity Rosmarinic acid.
Further, in the step 1, the concentration of ethanol solution is 90%-95%, and additional amount is rosemary cured leaf weight
5-10 times, Extracting temperature be 60-70 DEG C, extraction time 40-60min.
Further, in the step 2, when reduced pressure, temperature is 60-70 DEG C, vacuum degree be -0.07MPa to -
0.09MPa, concentration time 4-6h.
Further, in the step 3, acid solution is phosphoric acid, hydrochloric acid or citric acid, time of repose 24-48h；It adjusts
PH is 2-4.
Further, in the step 5, the dosage of n-butanol is 1-1.5 times of extracting solution C weight, extraction time 20-
30min；It is 65-75 DEG C that temperature, which is concentrated under reduced pressure, and vacuum degree is that -0.08MPa arrives -0.1MPa, concentration time 3-4h；Stand crystallization
Time is 12-24h.
Further, in the step 6, KOH replaces with basic potassium salt or weak acid formula sylvite；The PH of the potassium salt soln
For 7-9.
Further, in the step 7, the PH is 1-2, and acid solution is phosphoric acid or hydrochloric acid, solution temperature 60-70
DEG C, time of repose 12-24h.
Further, in the step 8, the additional amount of ethyl alcohol is 1-1.5 times of precipitate C weight, solution temperature 60-
70 DEG C, time of repose 12-24h.
Further, in the step 9, the additional amount of water is 1-1.5 times of precipitate C weight, solution temperature 60-70
DEG C, time of repose 12-24h.
Further, in the step 9, the purity of Rosmarinic acid is 99% or more.
Compared with prior art, the invention has the benefit that
1) purity is high of Rosmarinic acid obtained by the application, content is 99% or more；
2) 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；
3) 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 Rosmarinic acid from rosemary, comprising the following steps:
Step 1: choosing rosemary cured leaf, ethanol solution is added, extract twice, merge into extracting solution A；
Step 2: the extracting solution A that step 1 is obtained is concentrated under reduced pressure, the medicinal extract of acquisition, filtering, collects filtrate, and with filter
For liquid with the water washing filter residue of equimultiple, it is extracting solution B that washing water merges with filter liquor；
Step 3: in step 2 gained extracting solution B, acid solution is added, alkali tune PH is stood；
Step 4: step 3 acquired solution being filtered, precipitate is separated, obtains extracting solution C；
Step 5: obtaining extracting solution C and n-butanol, extraction is added, stratification releases water phase, and extract liquor is depressurized dense
Contracting, cooling and standings obtain precipitate A.
Step 6: step 5 gained precipitate A is added in KOH solution, the sylvite saturated solution of heat is configured, adjusts PH, it will
Solution is cooling, crystallizes, and filters, and washing obtains precipitate B；
Step 7: step 6 gained precipitate B being added in ethanol solution, acid solution is then added, is dissolved by heating, is adjusted
PH, cooling and standings recrystallization, obtains precipitate C；
Step 8: step 7 gained precipitate C is added in ethyl alcohol, is dissolved by heating, filtering, and filtrate cooling and standings is taken to tie again
Crystalline substance, and will be repeated several times, obtain precipitate D；
Step 9: step 8 gained precipitate D is added into water, is dissolved by heating, cooling and standings recrystallization, and will be repeated several times, institute
Obtaining crystal is resulting high-purity Rosmarinic acid.
Further, in the step 1, the concentration of ethanol solution is 90%-95%, and additional amount is rosemary cured leaf weight
5-10 times, Extracting temperature be 60-70 DEG C, extraction time 40-60min.
Further, in the step 2, when reduced pressure, temperature is 60-70 DEG C, vacuum degree be -0.07MPa to -
0.09MPa, concentration time 4-6h.
Further, in the step 3, acid solution is phosphoric acid, hydrochloric acid or citric acid, time of repose 24-48h；It adjusts
PH is 2-4.
Further, in the step 5, the dosage of n-butanol is 1-1.5 times of extracting solution C weight, extraction time 20-
30min；It is 65-75 DEG C that temperature, which is concentrated under reduced pressure, and vacuum degree is that -0.08MPa arrives -0.1MPa, concentration time 3-4h；Stand crystallization
Time is 12-24h.
Further, in the step 6, KOH replaces with basic potassium salt or weak acid formula sylvite；The PH of the potassium salt soln
For 7-9.
Further, in the step 7, the PH is 1-2, and acid solution is phosphoric acid or hydrochloric acid, solution temperature 60-70
DEG C, time of repose 12-24h.
Further, in the step 8, the additional amount of ethyl alcohol is 1-1.5 times of precipitate C weight, solution temperature 60-
70 DEG C, time of repose 12-24h.
Further, in the step 9, the additional amount of water is 1-1.5 times of precipitate C weight, solution temperature 60-70
DEG C, time of repose 12-24h.
According to method made above, the partial parameters in conjunction with shown in table 1-2 prepare embodiment 1-4, comparative example 1-4.
Table 1:
| Unit | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | |
| Concentration of alcohol | % | 90 | 92 | 95 | 94 |
| Additional amount | Times | 6 | 8 | 10 | 5 |
| Extracting temperature | ℃ | 60 | 70 | 65 | 65 |
| Extraction time | min | 50 | 40 | 60 | 55 |
| PH | —— | 4 | 3 | 2 | 3 |
| Additional amount | Times | 1 | 1 | 1.5 | 1.5 |
| Extraction time | min | 30 | 25 | 25 | 20 |
| PH | —— | 7 | 8 | 9 | 8 |
| PH | —— | 1 | 2 | 2 | 1 |
| Solution temperature | ℃ | 70 | 70 | 60 | 60 |
| Additional amount | Times | 12 | 24 | 12 | 12 |
| Additional amount | Times | 12 | 24 | 12 | 12 |
Table 2:
| Unit | Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
| Concentration of alcohol | % | 95 | 80 | 100 | 90 |
| Additional amount | Times | 8 | 15 | 15 | 3 |
| Extracting temperature | ℃ | 65 | 65 | 80 | 50 |
| Extraction time | min | 30 | 40 | 50 | 60 |
| PH | —— | 1 | 2 | 5 | 3 |
| Additional amount | Times | 2 | 1 | 0.5 | 1 |
| Extraction time | min | 20 | 30 | 40 | 30 |
| PH | —— | 6 | 8 | 8 | 10 |
| PH | —— | 1 | 2 | 3 | 4 |
| Solution temperature | ℃ | 50 | 80 | 60 | 60 |
| Additional amount | Times | 10 | 36 | 24 | 24 |
| Additional amount | Times | 10 | 36 | 24 | 24 |
Comparative example 5:
Lack step 5, extracting solution C is concentrated under reduced pressure after obtaining medicinal extract, is added in KOH solution, remaining step is according to implementation
It is prepared by example 2.
Comparative example 6:
Lack step 6, precipitate A is directly subjected to step 7, remaining is prepared according to embodiment 2.
Comparative example 7:
Ethanol solution in step 7 is changed to water, remaining is prepared according to embodiment 2.
Comparative example 8:
Lack step 8, remaining is prepared according to embodiment 2.
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 | |
| Rosmarinic acid concentration | % | 99.2 | 99.6 | 99.1 | 99.3 | 95.9 | 91.7 |
| Extracted amount | g | 9.78 | 10.16 | 9.83 | 9.66 | 8.35 | 7.59 |
Table 4:
| Unit | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 | |
| Rosmarinic acid concentration | % | 92.5 | 94.1 | 89.6 | 83.5 | 87.4 | 88.6 |
| Extracted amount | g | 8.16 | 8.56 | 7.09 | 6.74 | 7.37 | 8.29 |
As can be seen that resulting Rosmarinic acid purity is 99% or more according to the given preparation method of the application.Beyond this Shen
Please give method, then will affect the purity and yield 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 Rosmarinic acid from rosemary, which comprises the following steps:
Step 1: choosing rosemary cured leaf, ethanol solution is added, extract twice, merge into extracting solution A；
Step 2: the extracting solution A that step 1 is obtained is concentrated under reduced pressure, the medicinal extract of acquisition, filtering, collects filtrate, and with same with filtrate
The water washing filter residue of equimultiple, washing water merge with filter liquor, are extracting solution B；
Step 3: in step 2 gained extracting solution B, acid solution is added, alkali tune PH is stood；
Step 4: step 3 acquired solution being filtered, precipitate is separated, obtains extracting solution C；
Step 5: obtaining extracting solution C and n-butanol is added, extraction, stratification releases water phase, and extract liquor is concentrated under reduced pressure, cold
But it stands, obtains precipitate A.
Step 6: step 5 gained precipitate A being added in KOH solution, the sylvite saturated solution of heat is configured, PH is adjusted, by solution
It is cooling, it crystallizes, filters, washing obtains precipitate B；
Step 7: step 6 gained precipitate B is added in ethanol solution, acid solution is then added, is dissolved by heating, PH is adjusted, it is cold
But recrystallization is stood, precipitate C is obtained；
Step 8: step 7 gained precipitate C is added in ethyl alcohol, is dissolved by heating, filtering, and filtrate cooling and standings is taken to recrystallize,
And will be repeated several times, obtain precipitate D；
Step 9: step 8 gained precipitate D is added into water, is dissolved by heating, cooling and standings recrystallization, and will be repeated several times, gained is brilliant
Body is resulting high-purity Rosmarinic acid.
2. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 1, the concentration of ethanol solution is 90%-95%, and additional amount is 5-10 times of rosemary cured leaf weight, and Extracting temperature is
60-70 DEG C, extraction time 40-60min.
3. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 2, when reduced pressure, temperature is 60-70 DEG C, and vacuum degree is that -0.07MPa arrives -0.09MPa, concentration time 4-6h.
4. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 3, acid solution is phosphoric acid, hydrochloric acid or citric acid, time of repose 24-48h；Adjusting PH is 2-4.
5. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 5, the dosage of n-butanol is 1-1.5 times of extracting solution C weight, extraction time 20-30min；Temperature, which is concentrated under reduced pressure, is
65-75 DEG C, vacuum degree is that -0.08MPa arrives -0.1MPa, concentration time 3-4h；The standing crystallization time is 12-24h.
6. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 6, KOH replaces with basic potassium salt or weak acid formula sylvite；The PH of the potassium salt soln is 7-9.
7. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 7, the PH is 1-2, and acid solution is phosphoric acid or hydrochloric acid, and solution temperature is 60-70 DEG C, time of repose 12-24h.
8. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that described
In step 8, the additional amount of ethyl alcohol is 1-1.5 times of precipitate C weight, and solution temperature is 60-70 DEG C, time of repose 12-
24h。
9. according to claim 1 in re-crystallization step, which is characterized in that in the step 9, the additional amount of water is precipitate
1-1.5 times of C weight, solution temperature are 60-70 DEG C, time of repose 12-24h.
10. the preparation process of high-purity Rosmarinic acid is extracted from rosemary according to claim 1, which is characterized in that institute
It states in step 9, the purity of Rosmarinic acid is 99% or more.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112915040A (en) * | 2021-01-28 | 2021-06-08 | 晨光生物科技集团股份有限公司 | Rosemary extract with low ash content and high water solubility and preparation method thereof |
| CN114736123A (en) * | 2021-12-28 | 2022-07-12 | 海南舒普生物科技有限公司 | Method for extracting high-purity rosmarinic acid |
-
2019
- 2019-07-08 CN CN201910609696.0A patent/CN110283077A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112915040A (en) * | 2021-01-28 | 2021-06-08 | 晨光生物科技集团股份有限公司 | Rosemary extract with low ash content and high water solubility and preparation method thereof |
| CN112915040B (en) * | 2021-01-28 | 2023-12-08 | 晨光生物科技集团股份有限公司 | Rosemary extract with low ash content and high water solubility and preparation method thereof |
| CN114736123A (en) * | 2021-12-28 | 2022-07-12 | 海南舒普生物科技有限公司 | Method for extracting high-purity rosmarinic acid |
| CN114736123B (en) * | 2021-12-28 | 2023-10-03 | 海南舒普生物科技有限公司 | Method for extracting high-purity rosmarinic acid |
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Application publication date: 20190927 |