CN1032651C - Method for refining stevioside - Google Patents
Method for refining stevioside Download PDFInfo
- Publication number
- CN1032651C CN1032651C CN 93117563 CN93117563A CN1032651C CN 1032651 C CN1032651 C CN 1032651C CN 93117563 CN93117563 CN 93117563 CN 93117563 A CN93117563 A CN 93117563A CN 1032651 C CN1032651 C CN 1032651C
- Authority
- CN
- China
- Prior art keywords
- fatty alcohol
- water
- stevioside
- mixture
- thinner
- 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.)
- Expired - Fee Related
Links
- 235000019202 steviosides Nutrition 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 22
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 title claims abstract description 16
- 229940013618 stevioside Drugs 0.000 title claims abstract description 16
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000007670 refining Methods 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000003085 diluting agent Substances 0.000 abstract 1
- 235000013373 food additive Nutrition 0.000 abstract 1
- 239000002778 food additive Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- ILRCGYURZSFMEG-UHFFFAOYSA-N Salidroside Natural products OC1C(O)C(O)C(CO)OC1OCCC1=CC=C(O)C=C1 ILRCGYURZSFMEG-UHFFFAOYSA-N 0.000 description 12
- ILRCGYURZSFMEG-RQICVUQASA-N salidroside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OCCC1=CC=C(O)C=C1 ILRCGYURZSFMEG-RQICVUQASA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 229920003266 Leaf® Polymers 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 3
- 241000544066 Stevia Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- -1 alcohol compound Chemical class 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 238000005272 metallurgy Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- 101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 1
- 229930186291 Dulcoside Natural products 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000001512 FEMA 4601 Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 description 1
- 244000228451 Stevia rebaudiana Species 0.000 description 1
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000019203 rebaudioside A Nutrition 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- OMHUCGDTACNQEX-OSHKXICASA-N steviolbioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OMHUCGDTACNQEX-OSHKXICASA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
A method for refining stevioside used as food additive comprises liquid-liquid extracting crude water solution with fatty alcohol or fatty alcohol plus diluent, and back-extracting with water. Concentrating and drying the raffinate phase and the water phase obtained by back extraction respectively to obtain refined stevioside. The invention has simple process flow, white product, purity of more than 90 percent and no peculiar smell.
Description
The present invention relates to a kind of process for purification of foodstuff additive, particularly by the process for purification of the Steviosides that extracts in the leaf of sweet Stevia and the stem.
Steviosides is the novel sweetener that extracts from stevioside plant (Stevia Rebau diana) cured leaf and stem, the mixture that it is made up of eight kinds of saponins, wherein stevioside (Stevioside) accounts for 60-80%, stevioside A (Rebaudioside A) accounts for 10-30%, and all the other are stevioside B, C, D, E, Dulcoside and Steviobioside.
Steviosides product on the domestic and international market is many at present makes with resin adsorption method.This method, such as the Japanese Patent spy open clear 64-25790 and Chinese patent CN90 103875 announcement.The resin adsorption method yield is higher, and energy consumption is lower.But its shortcoming is: adopt the weak base anion-exchange resin decolouring, decolorizing efficiency is low, as decolouring with common strongly basic anion exchange resin, then this resin is in use very easily poisoned, since second circulation, the decolouring capacity reduces rapidly, and therefore, the product of Sheng Chaning often is with little yellow in this way.On high performance liquid chromatography (HPLC) figure more impurity honeybee is arranged, product has peculiar smell, and total salidroside content is 74-85%.Next is that the product purity of producing in this way can not satisfy the requirement of producing gourmet food and beverage sweetener, can not satisfy the requirement that is used to produce α-Portugal's synanthrin base stevioside raw material.
Chinese patent CN90104544.6 has disclosed a kind of method of removing peculiar smell, with the Petroleum ether extraction degreasing of stevioside product, uses anhydrous alcohol solution again, and calcium hydroxide, alumina adsorption, filtration, drying, yield are 80%.This method step is many, and reagent consumption is many, and industrial production is had any problem, and yield is on the low side.The Japanese Patent spy opens and adopts the methanol crystallization method to make the product that contains glucoside amount 96.6% among the clear 62-65158.But this law need be unfavorable for safety in production with a large amount of deleterious methyl alcohol, and colory stevioside A then is present in impurity and is difficult in the mother liquor reclaiming, and makes this method rate of recovery low.The Japanese Patent spy opens among the clear 56-109568 and to propose with total carbon atom number is 4 to 8 (to use C
4-C
8The expression, as follows) ethers, C
4-C
7Ester class or C
1-C
4The chloro alkanes extract solid stevioside enriched material or its aqueous solution as solvent, but the extraction efficiency of these solvents is low, products obtained therefrom still is faint yellow, product purity is lower.
The object of the present invention is to provide that a kind of technology is simple, product purity is high, the process for purification of the Steviosides of free from extraneous odour.
The present invention has adopted solvent extraction technology to carry out purifying, that is to say that the mixture that adds thinner with Fatty Alcohol(C12-C14 and C12-C18) or Fatty Alcohol(C12-C14 and C12-C18) carries out liquid-liquid extraction, and said Fatty Alcohol(C12-C14 and C12-C18) is to be 4 to 8 (C with total carbon atom number
4-C
8Expression, as follows) positive structure the simplification compound of isomery Fatty Alcohol(C12-C14 and C12-C18) or more than two kinds the mixture of above-mentioned alcohol make extraction agent.Said thinner can be C
6-C
10Hydro carbons, C
4-C
8Carboxylic acid esters, C
6-C
8Ketone or C
6-C
8Ether compound in one matter or its any mixture, the content of alcohol compound should be 5-100% in the organic phase.Extraction can be carried out under 10-35 ℃ temperature, and two contact compares (organic phase/water) for 0.5-3, can be with intermittent type or continous way counter-current extraction, and extraction progression is generally the 3-6 level.Raffinate water concentrating under reduced pressure, drying can be got total salidroside content greater than 95% Steviosides.With deionized water load organic phases is stripped, strip aqueous concentrating under reduced pressure, drying can be got total salidroside content greater than 90% Steviosides.Organic phase after the use can reclaim with distillation method.
The present invention compared with prior art, technical process is simple, the products obtained therefrom free from extraneous odour does not have impurity peaks on HPLC figure, purity is greater than more than 90%.
For further specifying the present invention, be several specific embodiments below:
Get 5 kilograms of exsiccant sweet Stevia cured leafs, adding 50 liters of tap water leached 1 hour in 70 ℃ hot water, leach altogether three times, discard residual leaf at last and get 122 liters of leach liquors, in leach liquor, add 500 gram industrial ferrous sulfates, stir half an hour, add 10% milk of lime again to pH9, produce green precipitate this moment, leaves standstill half an hour, remove by filter precipitate 116 liters of clear liquids.Clear liquid is passed through adsorption resin column, 10 liters of CO3 type macroporous adsorbent resins (Beijing Inst. of Chemical Metallurgy, Ministry of Nuclear Industry's product) absorption is housed in the post to finish with 25 liter of 70% ethanol elution adsorption resin column, with the stevioside of wash-out absorption, with this elutriant by desalting column and decolorizing column to remove ionogen and pigment.1 liter of J101 Zeo-karb (Beijing Inst. of Chemical Metallurgy, Ministry of Nuclear Industry's product) is housed in the desalting column, 1 liter of RCO4 anionite-exchange resin (nuclear industry Beijing emtallurgy research institute product) is housed in the decolorizing column, use 2.5 liter of 70% alcohol flushing desalination, decolorizing column again, effluent liquid and the elutriant after desalination, decolouring are merged.Again this solution is distilled out ethanol and part moisture content in distillation tower, get 4 liters of concentrated solutions, this liquid is divided into 4 equal portions, carry out following operation respectively.
Reference examples is got 1 liter of above-mentioned concentrated solution, and the following concentrate drying of decompression gets 1 38 grams and has micro-yellow powder.By standard GB 8270-87 methods analyst salidroside content 86%, dullness E
1% 370Be 0.120, it is 86.5% that HPLC analyzes the salidroside content summation, and impurity peaks accounts for 11%, and product has a small amount of peculiar smell.
Embodiment 1: get above-mentioned concentrated solution and make water for 1 liter, with 500 milliliters of primary isoamyl alcohol and 500 milliliters of organic phases that ethyl acetate is made, in extractor, carry out the extraction of 4 stage countercurrents, the raffinate water is through concentrating under reduced pressure, the dry 108 gram white powders that get, through HPLC analyzing total salidroside content 96.5%, wherein stevioside accounts for 70%, and stevioside A accounts for 22.5%, all the other five kinds of glucosides account for 4%, do not see impurity peaks.Press GB8270-87 and analyze salidroside content 95%, E
1% 370Be 0.040, the product free from extraneous odour.
The organic phase water is stripped, and strip aqueous is pressed GB8270-87 methods analyst salidroside content 90%, E through concentrating under reduced pressure, dry that white powder 12 restrains
1% 370Be 0.020, the product free from extraneous odour.
Embodiment 2: get above-mentioned concentrated solution and make water for 1 liter, carry out the extraction of 4 stage countercurrents with the organic phase that 500 milliliters of butanols and 500 milliliters of No. 120 industrial napthas are mixed with in extractor, the raffinate water is through concentrating under reduced pressure, dry 105 gram white powders, press GB8270-87 methods analyst salidroside content 95%, E
1% 370Be 0.045, the product free from extraneous odour.The organic phase water is stripped, and strip aqueous is through concentrating under reduced pressure, and is dry that white powder 14 restrains, and presses GB8270-87 methods analyst salidroside content 90%, E
1% 3700.025 product free from extraneous odour.
Embodiment 3: get above-mentioned concentrated solution and make water for 1 liter, with 250 milliliters of sec-butyl alcohols, 250 milliliters of primary isoamyl alcohol and 500 milliliters of organic phases that dibutyl ether is mixed with, in extractor, carry out the extraction of 4 stage countercurrents, the raffinate water is through concentrating under reduced pressure, the dry 107 gram white powders that get are pressed GB8270-87 methods analyst salidroside content 97%, E
1% 370Be 0.041, the product free from extraneous odour.The organic phase water is stripped, and strip aqueous is through concentrating under reduced pressure, and is dry that white powder 12 restrains, and presses GB8270-87 methods analyst salidroside content 91%, E
1% 370Be 0.020, the product free from extraneous odour.
The general glycoside rate of recovery of the present invention is greater than 90%.
Claims (1)
1, a kind of process for purification of Steviosides, adopt solvent extraction technology to carry out purifying, the invention is characterized in that adding thinner with Fatty Alcohol(C12-C14 and C12-C18) or Fatty Alcohol(C12-C14 and C12-C18) carries out intermittent type or continous way counter-current extraction to the solution of stevioside raw product under temperature is 10-35 ℃, extraction progression is 3～6, the volume ratio of organic phase and water is 0.5～3, the load organic phases water is stripped, raffinate water and strip aqueous are through concentrating, drying obtains high purity product, said Fatty Alcohol(C12-C14 and C12-C18) is meant that total carbon atom number is 4 to 8 normal fatty alcohol or the simplification compound of isomery Fatty Alcohol(C12-C14 and C12-C18) or the mixture of two or more above-mentioned alcohol, and said thinner is C
6-C
10Hydro carbons, C
4-C
8Carboxylic acid esters, C
4-C
8Ketone or C
4-C
8Ether compound in one matter or its any mixture, in the mixture of Fatty Alcohol(C12-C14 and C12-C18) and thinner, Fatty Alcohol(C12-C14 and C12-C18) content is 5-100%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93117563 CN1032651C (en) | 1993-09-21 | 1993-09-21 | Method for refining stevioside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93117563 CN1032651C (en) | 1993-09-21 | 1993-09-21 | Method for refining stevioside |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1100727A CN1100727A (en) | 1995-03-29 |
| CN1032651C true CN1032651C (en) | 1996-08-28 |
Family
ID=4992075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 93117563 Expired - Fee Related CN1032651C (en) | 1993-09-21 | 1993-09-21 | Method for refining stevioside |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1032651C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7923541B2 (en) | 2006-12-15 | 2011-04-12 | Chengdu Wagott Pharmaceutical Co., Ltd. | High-purity rebaudioside A and method of extracting same |
| US8299224B2 (en) | 2009-10-15 | 2012-10-30 | Purecircle Sdn Bhd | High-purity Rebaudioside D |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8334006B2 (en) | 2005-10-11 | 2012-12-18 | Purecircle Sdn Bhd | Process for manufacturing a sweetener and use thereof |
| US9107436B2 (en) | 2011-02-17 | 2015-08-18 | Purecircle Sdn Bhd | Glucosylated steviol glycoside as a flavor modifier |
| US8257948B1 (en) | 2011-02-17 | 2012-09-04 | Purecircle Usa | Method of preparing alpha-glucosyl Stevia composition |
| US8337927B2 (en) | 2005-10-11 | 2012-12-25 | Purecircle Sdn Bhd | Process for manufacturing a sweetener and use thereof |
| US8790730B2 (en) | 2005-10-11 | 2014-07-29 | Purecircle Usa | Process for manufacturing a sweetener and use thereof |
| US8318459B2 (en) | 2011-02-17 | 2012-11-27 | Purecircle Usa | Glucosyl stevia composition |
| CN101194707B (en) * | 2008-01-07 | 2010-10-20 | 青岛润德生物科技有限公司 | High purity stevioside glycoside refining process |
| CN101503435B (en) * | 2009-03-26 | 2011-07-06 | 李善汪 | Method for purifying stevioside by secondary ion exchange |
| US10888099B2 (en) | 2009-11-12 | 2021-01-12 | Purecircle Sdn Bhd. | Granulation of a Stevia sweetener |
| BR112012011382B1 (en) | 2009-11-12 | 2018-02-06 | Purecircle Usa Inc. | METHOD FOR PRODUCING A STEVIA GRANULATE SWEETENER AND SWEETENER |
| US20150344512A1 (en) | 2011-12-19 | 2015-12-03 | Purecircle Usa Inc. | Methods of purifying steviol glycosides and uses of the same |
| US10696706B2 (en) | 2010-03-12 | 2020-06-30 | Purecircle Usa Inc. | Methods of preparing steviol glycosides and uses of the same |
| MX346137B (en) | 2010-12-13 | 2017-03-08 | Purecircle Usa Inc | Highly soluble rebaudioside d. |
| WO2012108894A1 (en) | 2011-02-10 | 2012-08-16 | Purecircle Usa | Stevia composition |
| US9603373B2 (en) | 2011-02-17 | 2017-03-28 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US11690391B2 (en) | 2011-02-17 | 2023-07-04 | Purecircle Sdn Bhd | Glucosylated steviol glycoside as a flavor modifier |
| US9474296B2 (en) | 2011-02-17 | 2016-10-25 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9894922B2 (en) | 2011-05-18 | 2018-02-20 | Purecircle Sdn Bhd | Glucosyl rebaudioside C |
| EP2713763B1 (en) | 2011-05-31 | 2019-01-23 | PureCircle USA Inc. | Stevia composition |
| BR122018015762B1 (en) | 2011-06-03 | 2021-03-16 | Purecircle Usa Inc | composition of soluble stevia and composition of food, drink, pharmaceutical or cosmetic comprising said composition |
| PL2720561T3 (en) | 2011-06-20 | 2019-05-31 | Purecircle Usa Inc | Stevia composition |
| US9771434B2 (en) | 2011-06-23 | 2017-09-26 | Purecircle Sdn Bhd | Products from stevia rebaudiana |
| US10480019B2 (en) | 2011-08-10 | 2019-11-19 | Purecircle Sdn Bhd | Process for producing high-purity rubusoside |
| BR112014004581B1 (en) | 2011-09-07 | 2020-03-17 | Purecircle Usa Inc. | High solubility stevia sweetener, production method, powder, sweetener and flavor compositions, food ingredient, food, drink and cosmetic or pharmaceutical product of said sweetener |
| BR112014014965B1 (en) | 2011-12-19 | 2021-01-05 | The Coca-Cola Company | drink comprising glycosides |
| US9752174B2 (en) | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| MX395285B (en) | 2012-05-22 | 2025-03-25 | Purecircle Sdn Bhd | HIGH PURITY STEVIOL GLUCOSIDES. |
| ES2817049T5 (en) | 2013-06-07 | 2023-11-10 | Purecircle Usa Inc | Stevia extract containing selected steviol glycosides as a taste, flavor and sweetness profile modifier |
| US10952458B2 (en) | 2013-06-07 | 2021-03-23 | Purecircle Usa Inc | Stevia extract containing selected steviol glycosides as flavor, salty and sweetness profile modifier |
| EP3936513B1 (en) | 2014-09-02 | 2024-05-22 | PureCircle USA Inc. | Stevia extracts enriched in rebaudioside d, e, n and/or o and process for the preparation thereof |
| MX2018005148A (en) | 2015-10-26 | 2018-08-01 | Purecircle Usa Inc | Steviol glycoside compositions. |
| EP3389403A4 (en) | 2015-12-15 | 2019-09-04 | PureCircle USA Inc. | STEVIOL GLYCOSIDE COMPOSITIONS |
-
1993
- 1993-09-21 CN CN 93117563 patent/CN1032651C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7923541B2 (en) | 2006-12-15 | 2011-04-12 | Chengdu Wagott Pharmaceutical Co., Ltd. | High-purity rebaudioside A and method of extracting same |
| US8299224B2 (en) | 2009-10-15 | 2012-10-30 | Purecircle Sdn Bhd | High-purity Rebaudioside D |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1100727A (en) | 1995-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1032651C (en) | Method for refining stevioside | |
| US11891411B2 (en) | Industrial utilization method for Stevia rebaudiana and stevioside and chlorogenic acid of Stevia rebaudiana | |
| CN110845328B (en) | Method for preparing high-purity carnosic acid from rosemary ointment byproducts | |
| CN111848342B (en) | Method for separating and extracting natural ferulic acid from oryzanol-containing rice bran oil soapstock | |
| CN115109112B (en) | A kind of industrial production method of mogroside to increase the content of mogroside V | |
| CN108383890B (en) | Preparation method of high-content ginsenoside Re extract | |
| CN101407535B (en) | Preparation of high-purity Momordica grosvenori mogroside V | |
| CN112920034A (en) | Method for extracting 6-gingerol with content of more than or equal to 98% | |
| CN1168698C (en) | Macroporous resin adsorption process of extracting chlorogenic acid in high content | |
| CN1321961C (en) | New method for picking-up purified resveratrol from giant knotweed | |
| CN111187328B (en) | A kind of method for preparing mogrosinol | |
| CN113501759A (en) | Method for obtaining chlorogenic acid and isochlorogenic acid from stevia rebaudiana residue | |
| CN110917240B (en) | Continuous method for separating multiple effective components from cyclocarya paliurus | |
| CN1253940A (en) | Method for extracting tea-polyphenol from tea | |
| CN113527087B (en) | A kind of preparation method of high-purity ferulic acid | |
| US10301341B2 (en) | Technology for extracting and preparing high-purity raffinose from defatted wheat germ | |
| CN111349127A (en) | Method for producing stevioside | |
| CN112920043A (en) | Preparation method of carnosic acid with content of more than 99% | |
| CN113801003B (en) | Industrial extraction method of cannabidiol | |
| CN113248555B (en) | Preparation method of high-purity gentiopicroside | |
| CN111187315A (en) | Extraction system and extraction process of stevioside | |
| CN108912203B (en) | Preparation method of ginsenoside CK | |
| CN113861248A (en) | Method for treating heavy metals in pomegranate peel extracting solution and purifying punicalagin | |
| CN114014828A (en) | Method for recovering quercetin from stevioside extraction residues and application of quercetin | |
| CN1699392A (en) | Process for preparing total glucosides of picrorhiza rhizome |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |