CA2185496A1 - Method of extracting selected sweet glycosides from the stevia rebaudiana plant - Google Patents
Method of extracting selected sweet glycosides from the stevia rebaudiana plantInfo
- Publication number
- CA2185496A1 CA2185496A1 CA002185496A CA2185496A CA2185496A1 CA 2185496 A1 CA2185496 A1 CA 2185496A1 CA 002185496 A CA002185496 A CA 002185496A CA 2185496 A CA2185496 A CA 2185496A CA 2185496 A1 CA2185496 A1 CA 2185496A1
- Authority
- CA
- Canada
- Prior art keywords
- sweet
- glycosides
- glycoside
- sweet glycosides
- liquid solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/36—Terpene glycosides
Abstract
A method of extracting selected sweet glycosides from the stevia rebaudiana plant. Firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant using a water soluble organic solvent. Secondly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor containing other sweet glycosides.
Description
TITLE OF THE INVENTION:
method of extracting selected sweet glycosides from the stevia rebaudiana plant NAMES OF INVENTORS:
John Donald Payzant James Kenneth Laidler Robert Maurice Ippolito FIELD OF THE INVENTION
The present invention relates to a method of extracting selected sweet glycosides from the stevia rebaudiana plant.
R~CRGROUND OF THE INVENTION
Japanese Patent 63173531 which issued in 1988 to Nakazato describes a method of extracting sweet glycosides from the stevia rebaudiana plant. This method includes the following steps. Firstly, extracting a liquid solution of sweet glycosides from the stevia rebaudiana plant. Secondly, passing the liquid solution of sweet glycosides through a non-polar porous resin, such as amberlite XAD-2 and eluting with a water soluble organic solvent, preferably methanol. Thirdly, concentrating and drying the eluted solution to give a powdery material.
Subsequent patents, such as Korean Patent 9007421, have added to or varied the Nakazato process in an attempt to improve the purity and yield. Korean Patent 9007421, which issued in 1990 to Pacific Chemical Company, passes the eluted solution through a column which is packed with positive ion-exchange resin (preferably Diaion SKlB) and negative ion-exchange resin (Amberite IRA 904).
Of the sweet glycosides extracted from the stevia rebaudiana plant, rebaudioside A is recognized as having the most desirable sensory properties. The problem with the above described methods is that the resulting materials contain a mixture of all of the sweet glycosides.
SU~ARY OF THE INVENTION
What is required is a method of extracting selected sweet glycosides from the stevia rebaudiana plant.
According to the present invention there is provided a method of extracting selected sweet glycosides from the stevia rebaudiana plant. Firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant using a water soluble organic solvent. Secondly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor contAin;ng other sweet glycosides.
Unlike prior art methods which produce a powdery mixture of sweet glycosides, the above described method results in a crystallized solid contAining a higher concentration of the selected sweet glycoside. The selected sweet glycoside will normally, but not necessarily be rebaudioside A.
Although beneficial results may be obtained through the method, as described above, the higher the purity of rebaudioside A the better. It is, therefore, preferred that the method include further steps. Thirdly, dissolving the crystallized solid contAining a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside.
method of extracting selected sweet glycosides from the stevia rebaudiana plant NAMES OF INVENTORS:
John Donald Payzant James Kenneth Laidler Robert Maurice Ippolito FIELD OF THE INVENTION
The present invention relates to a method of extracting selected sweet glycosides from the stevia rebaudiana plant.
R~CRGROUND OF THE INVENTION
Japanese Patent 63173531 which issued in 1988 to Nakazato describes a method of extracting sweet glycosides from the stevia rebaudiana plant. This method includes the following steps. Firstly, extracting a liquid solution of sweet glycosides from the stevia rebaudiana plant. Secondly, passing the liquid solution of sweet glycosides through a non-polar porous resin, such as amberlite XAD-2 and eluting with a water soluble organic solvent, preferably methanol. Thirdly, concentrating and drying the eluted solution to give a powdery material.
Subsequent patents, such as Korean Patent 9007421, have added to or varied the Nakazato process in an attempt to improve the purity and yield. Korean Patent 9007421, which issued in 1990 to Pacific Chemical Company, passes the eluted solution through a column which is packed with positive ion-exchange resin (preferably Diaion SKlB) and negative ion-exchange resin (Amberite IRA 904).
Of the sweet glycosides extracted from the stevia rebaudiana plant, rebaudioside A is recognized as having the most desirable sensory properties. The problem with the above described methods is that the resulting materials contain a mixture of all of the sweet glycosides.
SU~ARY OF THE INVENTION
What is required is a method of extracting selected sweet glycosides from the stevia rebaudiana plant.
According to the present invention there is provided a method of extracting selected sweet glycosides from the stevia rebaudiana plant. Firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant using a water soluble organic solvent. Secondly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor contAin;ng other sweet glycosides.
Unlike prior art methods which produce a powdery mixture of sweet glycosides, the above described method results in a crystallized solid contAining a higher concentration of the selected sweet glycoside. The selected sweet glycoside will normally, but not necessarily be rebaudioside A.
Although beneficial results may be obtained through the method, as described above, the higher the purity of rebaudioside A the better. It is, therefore, preferred that the method include further steps. Thirdly, dissolving the crystallized solid contAining a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside.
3 2~85496 Fourthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid cont~ining an even higher concentration of the selected sweet glycoside and a second waste liquor contAining other sweet glycosides. These steps are, preferably, repeated over and over until a final crystallized solid of desired purity of the selected sweet glycoside is obtained.
Although beneficial results may be obtained through the use of the method described, there are impurities present in the sweet glycosides that adversely affect both the purity and the yield obtained. Even more beneficial results may, therefore, be obtained when an intermediate step is added of removing impurities in the liquid solution of sweet glycosides by column chromatography prior to crystallization. These impurities are primarily polysaccharides.
DETATT-~n DESCRIPTION OF THE EA~rr;KK~ EMBODIMENT
The preferred method of extracting sweet glycosides from the stevia rebaudiana plant includes the following steps.
Firstly, extracting a liquid solution of sweet glycosides from the stevia rebaudiana plant. There are a variety of suitable extraction methods described in the technical literature. Beneficial results have been obtained through a hot water extraction method.
Secondly, passing the liquid solution of sweet glycosides through a chromatographic column of resin layers. There are a variety of suitable resins. It is preferred, however, that the resin be based upon acrylic ester chemistry. An example of such a resin is the Amberlite XAD-7 resin commercially available through Rhom and Haas. An alternative resin is reverse phase C18 bonded silica. During column chromatography the sweet glycosides tend to be absorbed by the resin, while polysaccharide impurities were not absorbed.
Thirdly, eluting the sweet glycosides from the resin using a water soluble organic solvent to recover the liquid solution of mixed sweet glycosides with some impurities removed. The preferred form of water soluble organic solvent is a methanol solution.
Fourthly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid cont~in;ng a higher concentration of a selected sweet glycoside and a waste liquor cont~;ning other sweet glycosides. The selected sweet glycoside will normally be rebaudioside A. The waste liquor may either be disposed of or may be subject to further crystallization to remove another of the sweet glycosides, such as stevioside.
Fifthly, dissolving the crystallized solid cont~ining a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside. The preferred form of water soluble organic solvent is a methanol solution.
Sixthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid cont~ining an even higher concentration of the selected sweet glycoside and a second waste liquor cont~;n;ng other sweet glycosides.
Seventhly, repeating steps five and six until a final crystallized solid of desired purity of the selected sweet glycoside is obtained.
It will be apparent to one skilled in the art that modifications may be made to the illustrated embodiment without departing from the spirit and scope of the invention as hereinafter defined in the Claims.
Although beneficial results may be obtained through the use of the method described, there are impurities present in the sweet glycosides that adversely affect both the purity and the yield obtained. Even more beneficial results may, therefore, be obtained when an intermediate step is added of removing impurities in the liquid solution of sweet glycosides by column chromatography prior to crystallization. These impurities are primarily polysaccharides.
DETATT-~n DESCRIPTION OF THE EA~rr;KK~ EMBODIMENT
The preferred method of extracting sweet glycosides from the stevia rebaudiana plant includes the following steps.
Firstly, extracting a liquid solution of sweet glycosides from the stevia rebaudiana plant. There are a variety of suitable extraction methods described in the technical literature. Beneficial results have been obtained through a hot water extraction method.
Secondly, passing the liquid solution of sweet glycosides through a chromatographic column of resin layers. There are a variety of suitable resins. It is preferred, however, that the resin be based upon acrylic ester chemistry. An example of such a resin is the Amberlite XAD-7 resin commercially available through Rhom and Haas. An alternative resin is reverse phase C18 bonded silica. During column chromatography the sweet glycosides tend to be absorbed by the resin, while polysaccharide impurities were not absorbed.
Thirdly, eluting the sweet glycosides from the resin using a water soluble organic solvent to recover the liquid solution of mixed sweet glycosides with some impurities removed. The preferred form of water soluble organic solvent is a methanol solution.
Fourthly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid cont~in;ng a higher concentration of a selected sweet glycoside and a waste liquor cont~;ning other sweet glycosides. The selected sweet glycoside will normally be rebaudioside A. The waste liquor may either be disposed of or may be subject to further crystallization to remove another of the sweet glycosides, such as stevioside.
Fifthly, dissolving the crystallized solid cont~ining a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside. The preferred form of water soluble organic solvent is a methanol solution.
Sixthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid cont~ining an even higher concentration of the selected sweet glycoside and a second waste liquor cont~;n;ng other sweet glycosides.
Seventhly, repeating steps five and six until a final crystallized solid of desired purity of the selected sweet glycoside is obtained.
It will be apparent to one skilled in the art that modifications may be made to the illustrated embodiment without departing from the spirit and scope of the invention as hereinafter defined in the Claims.
Claims (5)
1. A method of extracting selected sweet glycosides from the stevia rebaudiana plant, comprising the steps of:
firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant; and secondly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor containing other sweet glycosides.
firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant; and secondly, crystallizing the liquid solution of sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor containing other sweet glycosides.
2. The method as defined in Claim 1, including further steps of:
thirdly, dissolving the crystallized solid containing a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside; and fourthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid containing an even higher concentration of the selected sweet glycoside and a second waste liquor containing other sweet glycosides.
thirdly, dissolving the crystallized solid containing a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside; and fourthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid containing an even higher concentration of the selected sweet glycoside and a second waste liquor containing other sweet glycosides.
3. The method as defined in Claim 2, having the further steps of repeating steps three and four until a final crystallized solid of desired purity of the selected sweet glycoside is obtained.
4. The method as defined in Claim 2, the water soluble organic solvent being a methanol solution.
5. A method of extracting selected sweet glycosides from the stevia rebaudiana plant, comprising the steps of:
firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant;
secondly, removing impurities from the liquid solution of sweet glycosides by passing the liquid solution through a chromatographic column of resin layers;
thirdly, eluting the sweet glycosides from the resin using a water soluble organic solvent to recover the liquid solution of mixed sweet glycosides with some impurities removed;
fourthly, crystallizing the liquid solution of mixed sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor containing other sweet glycosides;
fifthly, dissolving the crystallized solid containing a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside;
sixthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid containing an even higher concentration of the selected sweet glycoside and a second waste liquor containing other sweet glycosides; and seventhly, repeating steps five and six until a final crystallized solid of desired purity of the selected sweet glycoside is obtained.
firstly, extracting a liquid solution of mixed sweet glycosides from the stevia rebaudiana plant;
secondly, removing impurities from the liquid solution of sweet glycosides by passing the liquid solution through a chromatographic column of resin layers;
thirdly, eluting the sweet glycosides from the resin using a water soluble organic solvent to recover the liquid solution of mixed sweet glycosides with some impurities removed;
fourthly, crystallizing the liquid solution of mixed sweet glycosides to obtain a crystallized solid containing a higher concentration of a selected sweet glycoside and a waste liquor containing other sweet glycosides;
fifthly, dissolving the crystallized solid containing a higher concentration of the selected sweet glycoside using a water soluble organic solvent to obtain a sweet liquor of the selected sweet glycoside;
sixthly, crystallizing the sweet liquor of the selected sweet glycoside to obtain a second crystallized solid containing an even higher concentration of the selected sweet glycoside and a second waste liquor containing other sweet glycosides; and seventhly, repeating steps five and six until a final crystallized solid of desired purity of the selected sweet glycoside is obtained.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002185496A CA2185496A1 (en) | 1996-09-13 | 1996-09-13 | Method of extracting selected sweet glycosides from the stevia rebaudiana plant |
| US09/019,558 US5962678A (en) | 1996-09-13 | 1998-02-06 | Method of extracting selected sweet glycosides from the Stevia rebaudiana plant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002185496A CA2185496A1 (en) | 1996-09-13 | 1996-09-13 | Method of extracting selected sweet glycosides from the stevia rebaudiana plant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2185496A1 true CA2185496A1 (en) | 1998-03-14 |
Family
ID=4158907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002185496A Abandoned CA2185496A1 (en) | 1996-09-13 | 1996-09-13 | Method of extracting selected sweet glycosides from the stevia rebaudiana plant |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2185496A1 (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000030464A1 (en) * | 1998-11-25 | 2000-06-02 | Irma Frey | Extract |
| WO2008091547A3 (en) * | 2007-01-22 | 2009-03-12 | Cargill Inc | Method of producing purified rebaudioside a compositions using solvent/antisolvent crystallization |
| WO2011037959A1 (en) * | 2009-09-22 | 2011-03-31 | Redpoint Bio Corporation | Novel polymorphs of rebaudioside c and methods for making and using the same |
| WO2012006742A1 (en) * | 2010-07-16 | 2012-01-19 | Justbio Inc. | Extraction method for providing an organic certifiable stevia rebaudiana extract |
| US8524785B2 (en) | 2009-09-04 | 2013-09-03 | International Flavors And Fragrances Inc. | Methods for using rebaudioside C as a flavor enhancer |
| US8609069B2 (en) | 2009-05-18 | 2013-12-17 | Redpoint Bio Corporation | Rebaudioside C and its stereoisomers as natural product sweetness enhancers |
| WO2014097319A1 (en) * | 2012-12-22 | 2014-06-26 | Sevak Niravkumar Prakashbhai | Extraction method for organic certifiable steviosides from organic stevia leaves |
| US8889841B2 (en) | 2011-11-18 | 2014-11-18 | International Flavors & Fragrances Inc. | Method for purifying rebaudioside C |
| US9131718B2 (en) | 2009-06-16 | 2015-09-15 | Epc (Beijing) Natural Products Co., Ltd. | Process for rebaudioside D |
| US9578895B2 (en) | 2010-08-23 | 2017-02-28 | Epc (Beijing) Natural Products Co., Ltd. | Rebaudioside A and stevioside compositions |
| US9795156B2 (en) | 2011-03-17 | 2017-10-24 | E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd | Rebaudioside B and derivatives |
| US10264811B2 (en) | 2014-05-19 | 2019-04-23 | Epc Natural Products Co., Ltd. | Stevia sweetener with improved solubility |
| US10357052B2 (en) | 2014-06-16 | 2019-07-23 | Sweet Green Fields USA LLC | Rebaudioside A and stevioside with improved solubilities |
| US10485256B2 (en) | 2014-06-20 | 2019-11-26 | Sweet Green Fields International Co., Limited | Stevia sweetener with improved solubility with a cyclodextrin |
-
1996
- 1996-09-13 CA CA002185496A patent/CA2185496A1/en not_active Abandoned
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000030464A1 (en) * | 1998-11-25 | 2000-06-02 | Irma Frey | Extract |
| WO2008091547A3 (en) * | 2007-01-22 | 2009-03-12 | Cargill Inc | Method of producing purified rebaudioside a compositions using solvent/antisolvent crystallization |
| US8937168B2 (en) | 2007-01-22 | 2015-01-20 | Cargill, Incorporated | Method of producing purified rebaudioside A compositions using solvent/antisolvent crystallization |
| US8609069B2 (en) | 2009-05-18 | 2013-12-17 | Redpoint Bio Corporation | Rebaudioside C and its stereoisomers as natural product sweetness enhancers |
| US9131718B2 (en) | 2009-06-16 | 2015-09-15 | Epc (Beijing) Natural Products Co., Ltd. | Process for rebaudioside D |
| US9635878B2 (en) | 2009-06-16 | 2017-05-02 | Epc (Beijing) Natural Products Co., Ltd. | Process for rebaudioside D |
| US8524785B2 (en) | 2009-09-04 | 2013-09-03 | International Flavors And Fragrances Inc. | Methods for using rebaudioside C as a flavor enhancer |
| WO2011037959A1 (en) * | 2009-09-22 | 2011-03-31 | Redpoint Bio Corporation | Novel polymorphs of rebaudioside c and methods for making and using the same |
| EP2658394A4 (en) * | 2010-07-16 | 2014-04-30 | Justbio Inc | Extraction method for providing an organic certifiable stevia rebaudiana extract |
| US8728545B2 (en) | 2010-07-16 | 2014-05-20 | Justbio Inc. | Extraction method for providing an organic certifiable Stevia rebaudiana extract |
| EP2658394A1 (en) * | 2010-07-16 | 2013-11-06 | Justbio Inc. | Extraction method for providing an organic certifiable stevia rebaudiana extract |
| WO2012006742A1 (en) * | 2010-07-16 | 2012-01-19 | Justbio Inc. | Extraction method for providing an organic certifiable stevia rebaudiana extract |
| US10285425B2 (en) | 2010-08-23 | 2019-05-14 | Epc Natural Products Co. Ltd | Rebaudioside A and stevioside compositions |
| US9578895B2 (en) | 2010-08-23 | 2017-02-28 | Epc (Beijing) Natural Products Co., Ltd. | Rebaudioside A and stevioside compositions |
| US11202462B2 (en) | 2010-08-23 | 2021-12-21 | Sweet Green Fields International Co., Limited | Rebaudioside A and stevioside compositions |
| US11510428B2 (en) | 2011-03-17 | 2022-11-29 | Sweet Green Fields International Co., Limited | Rebaudioside B and derivatives |
| US9795156B2 (en) | 2011-03-17 | 2017-10-24 | E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd | Rebaudioside B and derivatives |
| US8889841B2 (en) | 2011-11-18 | 2014-11-18 | International Flavors & Fragrances Inc. | Method for purifying rebaudioside C |
| WO2014097319A1 (en) * | 2012-12-22 | 2014-06-26 | Sevak Niravkumar Prakashbhai | Extraction method for organic certifiable steviosides from organic stevia leaves |
| US10561165B2 (en) | 2014-05-19 | 2020-02-18 | Sweet Green Fields International Co., Limited | Stevia sweetener with improved solubility |
| US10264811B2 (en) | 2014-05-19 | 2019-04-23 | Epc Natural Products Co., Ltd. | Stevia sweetener with improved solubility |
| US11206857B2 (en) | 2014-05-19 | 2021-12-28 | Sweet Green Fields International Co., Limited | Stevia sweetener with improved solubility |
| US10357052B2 (en) | 2014-06-16 | 2019-07-23 | Sweet Green Fields USA LLC | Rebaudioside A and stevioside with improved solubilities |
| US10568351B2 (en) | 2014-06-16 | 2020-02-25 | Sweet Green Fields USA LLC | Rebaudioside A and stevioside with improved solubilities |
| US11241031B2 (en) | 2014-06-16 | 2022-02-08 | Sweet Green Fields Usa, Llc | Rebaudioside A and stevioside with improved solubilities |
| US10485256B2 (en) | 2014-06-20 | 2019-11-26 | Sweet Green Fields International Co., Limited | Stevia sweetener with improved solubility with a cyclodextrin |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |