CN1803801A - Method for preparing ellagic acid by pomegranate rind - Google Patents
Method for preparing ellagic acid by pomegranate rind Download PDFInfo
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- CN1803801A CN1803801A CN 200510002081 CN200510002081A CN1803801A CN 1803801 A CN1803801 A CN 1803801A CN 200510002081 CN200510002081 CN 200510002081 CN 200510002081 A CN200510002081 A CN 200510002081A CN 1803801 A CN1803801 A CN 1803801A
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Abstract
The invention relates to a process for preparing ellagic acid by using pomegranate peel as raw material through the steps of solvent extraction, evaporation condensation, acid hydrolysis and crystallization.
Description
Technical field:
The present invention relates to a kind of is the method for feedstock production ellagic acid with the pomegranate rind.
Background technology:
Ellagic acid (ellagic acid) is a kind of natural polyphenol component that extensively is present in the plant tissues such as various mushy fruits, nut (C14H6O8), and it is the dimerization derivative of gallic acid, is a kind of polyphenol dilactone.Natural ellagic acid is a kind of polyphenolic substance, and is different with cis gallic acid and tannin thereof, and it is present in the fruit of various plants, is trans gallic acid tannin structure.
Ellagic acid has stronger anti peroxidation of lipid, the ability of Mulberry Extract, can suppress the canceration that polynuclear aromatics, aflatoxin and aromatic amine etc. cause.Its major physiological function has:
(1) to the restraining effect of HIV (human immunodeficiency virus);
(2) anticancer/anti-mutation performance: suppressing the Metabolic activity of carcinogen, remove carcinogenic toxicity, is the carcinogens scavenging agent, occupies DNA on the position that may react with carcinogenic substance or its metabolite;
(3) antioxygenation;
(4) other effect: have stomach and intestine dynamics, urogenital dynamic action; Has antibiotic, antiviral efficacy; Has coagulation function; Other discovers that ellagic acid also has step-down, sedative effect.
Over past ten years, owing to found the anti-mutation of ellagic acid, anticancer change effect, and, caused that people pay close attention to widely to the restraining effect of chemical carcinogen.The preparation method of ellagic acid mainly contains following several method:
A kind of is to extract ellagic acid from plant.Occurring in nature contains a small amount of ellagic acid (1%) in the plants such as the redwood certain kind of berries, strawberry, pomegranate and fern.At present, it is being raw material with strawberry, pomegranate that four or five tame factories are arranged in the world approximately, can produce content and be about 5% natural ellagic acid extract, is used for foodstuff additive; Can produce highly purified ellagic acid with this technology, but owing to be subjected to raw materials cost higher, and in the raw material ellagic acid content restriction and have little significance.
Another kind method is to produce ellagic acid by gallic acid or gallic acid ester by the oxypolymerization effect under the enzyme effect (to see: Nrusingha C.Mishra and Barry Gold.Synthesis of
13C-and
14C-labelled ellagic acid[J] .Journal of Labelled Compounds andRadiopharmaceuticals, 1990,8:927-941), and the preparation method of this ellagic acid, productive rate is 20～30%.But the preparation process of used gallic acid (ester) itself is very complicated very, enzyme also needs refining purifying, and also has a kind of quinones substance of the unknown in the product, the ratio of itself and ellagic acid is 1: 2.4, for the product separation purifying has brought very big difficulty, therefore present this method of less usefulness is carried out the production of ellagic acid.
European patent (EP 0 390 107A2 Kiyoshi M., Yasuhiko I., Katsumi Y., etal) disclosing another kind of method, to prepare productive rate be 50～60% ellagic acid, with the Turkey-galls is raw material, use methanol extraction, it is 7.9 that insolubles filtration rear filtrate is transferred pH by 40% NaOH solution, adds 1.89gNaHCO
3In the U.S. Erlenmeyer flask of love he of 250mL, 25 ℃ of joltings of temperature 20 hours, shake fast 200rpm, every 20mL reaction solution adds 4mL0.1mol/L hydrochloric acid, and centrifugation obtains precipitation, precipitation is dissolved in 4mL methyl alcohol, with high performance liquid chromatography (255nm, TSK ODS120A post, 25cm), it is moving phase that the phosphate buffered saline buffer of M/30 pH7.0 and methyl alcohol were made into mixed solution with 7: 3, reaction yield 48.0%.
But but Turkey-galls is the insect gall of animal, though belong to Chinese medicine only limit to external application, therefore, is that the ellagic acid of production feedstock production can not be used for foodstuff additive with the Turkey-galls.The ellagic acid quality that obtains is lower, and outward appearance and color are relatively poor.Add that to state method steps various, the cycle is long, and the production cost height is difficult for extensive the operation.
Summary of the invention:
The object of the present invention is to provide a kind of is raw material with the pomegranate rind, prepares the method for ellagic acid through solvent extraction, evaporation concentration, acidification hydrolization and crystallization.Method of the present invention with China a large amount of be raw material by people's depleted pomegranate rind, can prepare expensive medical high purity ellagic acid, technology is simple, is suitable for industry to be amplified.
The invention main points:
Technical process is as follows:
The present invention is a kind of method of preparing ellagic acid by pomegranate rind, in turn includes the following steps:
A. organic solvent extraction
After the pomegranate rind of oven dry pulverized, join concentration and be in 20～60% the aqueous ethanolic solution, refluxing decocts, and the time of decoction is 2～6 hours, and the aqueous ethanolic solution of the Weibull that obtains is concentrated, reclaim ethanol after, obtain the Weibull concentrated solution.
B. acidifying
The 1-2 that the Weibull concentrated solution that steps A is obtained is diluted with water to original volume doubly adds 98% the vitriol oil, and the volume of the vitriol oil of adding is 4～8% of a reaction solution cumulative volume, under 100-110 ℃, and stirring reaction 4～8 hours.
C. solid-liquid separation
Behind the reacting liquid filtering that step B is obtained, filter cake obtains the thick product of ellagic acid through washing, drying, and purity is about 50%;
D. solvent crystallization purifying
The thick product of ellagic acid is added methyl alcohol, after extracting 3～9 hours under 70～80 ℃ of temperature, extraction liquid is concentrated into saturated, reduce to crystallizing at room temperature, behind the reacting liquid filtering, filter cake is through washing, drying, and obtaining purity is faint yellow ellagic acid product more than 95%.
In order to improve productive rate in the organic solvent extraction process of steps A, decoction can divide secondary to finish, each 1～3 hour.
In order to improve purity in the solvent crystallization purifying of step D, extraction can divide finishes each 1～3 hour for two to three times.
The invention effect:
It is ellagic acid product more than 95% that the present invention adopts solvent extraction, evaporation concentration, acidification hydrolization and crystalline method can obtain purity.This method technology is simple, is fit to scale operation.China is pomegranate plantation big country, and its pericarp is except that being partly used for Chinese medicinal materials, and major part is all abandoned by people, has caused very big waste.With the pomegranate rind is the expensive ellagic acid of raw material production, has boundless economic outlook.
Embodiment:
Embodiment 1:
(1) organic solvent extraction
40 kilograms of Pomegranate Rinds, 40% the ethanolic soln that adds 200L refluxes and decocts, and decocting number of times is 2 times, each 1 hour, centrifugal, merge supernatant liquor, obtain the aqueous ethanolic solution 350L of Weibull, concentrate and reclaim ethanol, obtain 80L Weibull concentrated solution.
(2) acidifying
The above-mentioned Weibull concentrated solution that obtains adds water to 150L, adds the vitriol oil of 8L98%, and 105 ℃ were reacted 4 hours.
(3) solid-liquid separation
Reacting liquid filtering, filter cake washing 2～3 times, drying gets thick ellagic acid product 4.55kg, and purity is 50.2%.
(4) solvent crystallization
With the thick product 75 ℃ of extractions of 60L methyl alcohol that obtain, extraction times is 3 times, each 1 hour, and solid-liquid separation, merge liquid, evaporation concentration is to 15L, and crystallisation by cooling filters crystal, drying obtains 1.85 kilograms of faint yellow ellagic acid powder, and purity is 97.5%, and yield is 79.0%.
Embodiment 2:
(1) organic solvent extraction
40 kilograms of Pomegranate Rinds, 60% the ethanolic soln that adds 300L refluxes and decocts, and decocting number of times is 2 times, each 2 hours, centrifugal, merge supernatant liquor, obtain the aqueous ethanolic solution 420L of Weibull, concentrate and reclaim ethanol, obtain 100L Weibull concentrated solution.
(2) acidifying
The above-mentioned Weibull concentrated solution that obtains adds water to 200L, adds the 9L98% vitriol oil, 105 ℃ of reaction 5hr.
(3) solid-liquid separation
Reacting liquid filtering, filter cake washing 2～3 times, drying gets thick ellagic acid product 3.59g, and purity is 55.6%.
(4) solvent crystallization
With the thick product 75 ℃ of extractions of 60L methyl alcohol that obtain, extraction times is 2 times, each 2 hours, and solid-liquid separation, merge liquid, evaporation concentration is to 15L, and crystallisation by cooling filters crystal, drying obtains the faint yellow ellagic acid powder of 1.68kg, and purity is 99.1%, and yield is 83.4%.
Embodiment 3:
(1) organic solvent extraction
40 kilograms of Pomegranate Rinds, 50% the ethanolic soln that adds 250L refluxes and decocts, and decocting number of times is 2 times, each 3 hours, centrifugal, merge supernatant liquor, obtain the aqueous ethanolic solution 380L of Weibull, concentrate and reclaim ethanol, obtain 90L Weibull concentrated solution.
(2) acidifying
The above-mentioned Weibull concentrated solution that obtains adds water to 150L, adds the 7.5L vitriol oil, and 110 ℃ were reacted 6 hours.
(3) solid-liquid separation
Reacting liquid filtering, filter cake washing 2～3 times, drying gets thick ellagic acid product 4.25g, and purity is 52.4%.
(4) solvent crystallization
With the thick product 75 ℃ of extractions of 70L methyl alcohol that obtain, extraction times is 3 times, each 2 hours, and solid-liquid separation, merge liquid, evaporation concentration is to 20L, and crystallisation by cooling filters crystal, drying obtains the faint yellow ellagic acid powder of 1.76kg, and purity is 98.2%, and yield is 77.6%.
Claims (3)
1. the method for a preparing ellagic acid by pomegranate rind in turn includes the following steps:
A. organic solvent extraction
After the pomegranate rind of oven dry pulverized, join concentration and be in 20～60% the aqueous ethanolic solution, refluxing decocts, and the time of decoction is 2～6 hours, with the aqueous ethanolic solution of the Weibull that obtains concentrate reclaim ethanol after, obtain the Weibull concentrated solution;
B. acidifying
The 1-2 that the Weibull concentrated solution that steps A is obtained is diluted with water to original volume doubly adds 98% the vitriol oil, and the volume of the vitriol oil of adding is 4～8% of a reaction solution cumulative volume, under 100-110 ℃, and stirring reaction 4～8 hours;
C. solid-liquid separation
Behind the reacting liquid filtering that step B is obtained, filter cake obtains the thick product of ellagic acid through washing, drying;
D. solvent crystallization purifying
The thick product of ellagic acid is added methyl alcohol, after extracting 3～9 hours under 70～80 ℃ of temperature, extraction liquid is concentrated into saturated, reduce to crystallizing at room temperature, behind the reacting liquid filtering, filter cake obtains faint yellow ellagic acid product through washing, drying.
2. according to the method for claim 1, it is characterized in that: in the organic solvent extraction process of steps A, decoct and divide secondary to finish each 1～3 hour.
3. according to the method for claim 1, it is characterized in that: in the solvent crystallization purifying of step D, extraction divides finishes each 1～3 hour two to three times.
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| CNB200510002081XA CN100497343C (en) | 2005-01-14 | 2005-01-14 | Method for preparing ellagic acid by pomegranate rind |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101974043A (en) * | 2010-11-03 | 2011-02-16 | 西安应化生物技术有限公司 | Method for preparing punicalagin and ellagic acid from pomegranate rind |
| CN101434608B (en) * | 2008-12-12 | 2011-04-27 | 桂林莱茵生物科技股份有限公司 | Preparation of high-purity ellagic acid |
| CN101718690B (en) * | 2009-12-11 | 2011-11-09 | 天津市林业果树研究所 | Method for measuring content of ellagic acid substance in raspberry |
| CN102250981A (en) * | 2010-05-21 | 2011-11-23 | 北京化工大学 | Method for preparing ellagic acid by solid fermentation with granatum as raw material |
| CN101747388B (en) * | 2008-12-19 | 2012-01-11 | 成都华高药业有限公司 | Method for simultaneously extracting punicalagin and ellagic acid from pomegranate bark |
| CN102453038A (en) * | 2010-11-03 | 2012-05-16 | 张守力 | Method for extracting ellagic acid from pomegranate peels |
| CN102807570A (en) * | 2012-08-17 | 2012-12-05 | 中国林业科学研究院林产化学工业研究所 | Method for preparing gallogen by platycarya strobilacea fruit |
| CN102892416A (en) * | 2010-04-08 | 2013-01-23 | 株式会社建康爱 | Pomegranate extract having high ellagic acid content, and use of pomegranate extract |
| CN104341431A (en) * | 2014-09-30 | 2015-02-11 | 桂林三宝生物科技有限公司 | Method for extracting ellagic acid from pomegranate peel |
| CN106344633A (en) * | 2016-09-28 | 2017-01-25 | 江苏春申堂药业有限公司 | Preparation method of pericarpium granati extract under normal temperature |
| CN106565736A (en) * | 2016-11-13 | 2017-04-19 | 北京化工大学 | Method for preparing ellagic acid in pomegranate bark through steam explosion |
| CN106632380A (en) * | 2016-11-21 | 2017-05-10 | 东北林业大学 | Process for producing high-purity ellagic acid by desolvation crystallization method |
| CN110357900A (en) * | 2019-08-02 | 2019-10-22 | 中国科学院新疆理化技术研究所 | A kind of intermediate processing obtaining ellagic acid from pomegranate rind extract |
| CN113480556A (en) * | 2021-07-13 | 2021-10-08 | 劲牌有限公司 | Preparation method of ellagic acid in oak |
| CN115960114A (en) * | 2022-12-29 | 2023-04-14 | 陕西嘉禾药业有限公司 | Method for preparing high-content ellagic acid from pomegranate rind |
| IT202200005339A1 (en) * | 2022-03-18 | 2023-09-18 | Simona Rapposelli | EXTRACTION METHOD AND EXTRACTS SO OBTAINED |
| WO2024009260A1 (en) | 2022-07-07 | 2024-01-11 | Universidade De Aveiro | Method for the recovery of ellagic acid from industrial pulp mill streams |
-
2005
- 2005-01-14 CN CNB200510002081XA patent/CN100497343C/en active Active
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101434608B (en) * | 2008-12-12 | 2011-04-27 | 桂林莱茵生物科技股份有限公司 | Preparation of high-purity ellagic acid |
| CN101747388B (en) * | 2008-12-19 | 2012-01-11 | 成都华高药业有限公司 | Method for simultaneously extracting punicalagin and ellagic acid from pomegranate bark |
| CN101718690B (en) * | 2009-12-11 | 2011-11-09 | 天津市林业果树研究所 | Method for measuring content of ellagic acid substance in raspberry |
| CN102892416B (en) * | 2010-04-08 | 2015-10-21 | 株式会社建康爱 | Containing the Punica granatum L. extract of a large amount of ellagic acid and the purposes of Punica granatum L. extract |
| CN102892416A (en) * | 2010-04-08 | 2013-01-23 | 株式会社建康爱 | Pomegranate extract having high ellagic acid content, and use of pomegranate extract |
| CN102250981A (en) * | 2010-05-21 | 2011-11-23 | 北京化工大学 | Method for preparing ellagic acid by solid fermentation with granatum as raw material |
| CN102250981B (en) * | 2010-05-21 | 2013-09-18 | 北京化工大学 | Method for preparing ellagic acid by solid fermentation with granatum as raw material |
| CN102453038A (en) * | 2010-11-03 | 2012-05-16 | 张守力 | Method for extracting ellagic acid from pomegranate peels |
| CN101974043B (en) * | 2010-11-03 | 2012-05-23 | 西安应化生物技术有限公司 | Method for preparing punicalagin and ellagic acid from pomegranate rind |
| CN101974043A (en) * | 2010-11-03 | 2011-02-16 | 西安应化生物技术有限公司 | Method for preparing punicalagin and ellagic acid from pomegranate rind |
| CN102807570A (en) * | 2012-08-17 | 2012-12-05 | 中国林业科学研究院林产化学工业研究所 | Method for preparing gallogen by platycarya strobilacea fruit |
| CN102807570B (en) * | 2012-08-17 | 2015-09-02 | 中国林业科学研究院林产化学工业研究所 | The fragrant fruit of a kind ofization prepares the method for ellagic acid |
| CN104341431A (en) * | 2014-09-30 | 2015-02-11 | 桂林三宝生物科技有限公司 | Method for extracting ellagic acid from pomegranate peel |
| CN106344633A (en) * | 2016-09-28 | 2017-01-25 | 江苏春申堂药业有限公司 | Preparation method of pericarpium granati extract under normal temperature |
| CN106565736A (en) * | 2016-11-13 | 2017-04-19 | 北京化工大学 | Method for preparing ellagic acid in pomegranate bark through steam explosion |
| CN106565736B (en) * | 2016-11-13 | 2019-01-04 | 北京化工大学 | A method of Ellagic Acid in Granati Cortex is prepared using steam blasting |
| CN106632380A (en) * | 2016-11-21 | 2017-05-10 | 东北林业大学 | Process for producing high-purity ellagic acid by desolvation crystallization method |
| CN110357900A (en) * | 2019-08-02 | 2019-10-22 | 中国科学院新疆理化技术研究所 | A kind of intermediate processing obtaining ellagic acid from pomegranate rind extract |
| CN113480556A (en) * | 2021-07-13 | 2021-10-08 | 劲牌有限公司 | Preparation method of ellagic acid in oak |
| IT202200005339A1 (en) * | 2022-03-18 | 2023-09-18 | Simona Rapposelli | EXTRACTION METHOD AND EXTRACTS SO OBTAINED |
| WO2024009260A1 (en) | 2022-07-07 | 2024-01-11 | Universidade De Aveiro | Method for the recovery of ellagic acid from industrial pulp mill streams |
| CN115960114A (en) * | 2022-12-29 | 2023-04-14 | 陕西嘉禾药业有限公司 | Method for preparing high-content ellagic acid from pomegranate rind |
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| CN100497343C (en) | 2009-06-10 |
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