CN108864222A - A kind of preparation method of high-purity steviosides RD and RM - Google Patents
A kind of preparation method of high-purity steviosides RD and RM Download PDFInfo
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- CN108864222A CN108864222A CN201810654176.7A CN201810654176A CN108864222A CN 108864222 A CN108864222 A CN 108864222A CN 201810654176 A CN201810654176 A CN 201810654176A CN 108864222 A CN108864222 A CN 108864222A
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- 235000019202 steviosides Nutrition 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011259 mixed solution Substances 0.000 claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 239000012452 mother liquor Substances 0.000 claims abstract description 19
- 229910021642 ultra pure water Inorganic materials 0.000 claims abstract description 15
- 239000012498 ultrapure water Substances 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 239000004383 Steviol glycoside Substances 0.000 claims abstract description 9
- 229930182488 steviol glycoside Natural products 0.000 claims abstract description 9
- 235000019411 steviol glycoside Nutrition 0.000 claims abstract description 9
- 150000008144 steviol glycosides Chemical class 0.000 claims abstract description 9
- 239000012141 concentrate Substances 0.000 claims abstract description 6
- 238000012797 qualification Methods 0.000 claims abstract description 6
- 238000010790 dilution Methods 0.000 claims abstract description 5
- 239000012895 dilution Substances 0.000 claims abstract description 5
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 4
- 239000003480 eluent Substances 0.000 claims abstract description 4
- 239000006185 dispersion Substances 0.000 claims abstract description 3
- 238000011067 equilibration Methods 0.000 claims abstract description 3
- 235000019441 ethanol Nutrition 0.000 claims description 27
- 238000011068 loading method Methods 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 5
- 238000000825 ultraviolet detection Methods 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 2
- 235000019640 taste Nutrition 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 239000000523 sample Substances 0.000 abstract description 12
- 239000012488 sample solution Substances 0.000 abstract description 2
- RPYRMTHVSUWHSV-CUZJHZIBSA-N rebaudioside D 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]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 RPYRMTHVSUWHSV-CUZJHZIBSA-N 0.000 description 30
- GSGVXNMGMKBGQU-PHESRWQRSA-N rebaudioside M Chemical compound C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSGVXNMGMKBGQU-PHESRWQRSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 7
- 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 7
- 239000001512 FEMA 4601 Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- 235000019203 rebaudioside A Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- 229940013618 stevioside Drugs 0.000 description 4
- 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 description 4
- 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 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000019605 sweet taste sensations Nutrition 0.000 description 3
- 244000228451 Stevia rebaudiana Species 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 that is Substances 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention relates to the preparation methods of high-purity steviosides RD and RM a kind of, and specific step is as follows：（1）Resin dispersion is stirred evenly in the mixed solution of second alcohol and water, and is fitted into chromatographic column, rinses compacting chromatographic column bed with the mixed solution of second alcohol and water；（2）Steviol glycoside mother liquor sugar dope is taken to be diluted to mother liquor sugar dilution；（3）By step（2）Obtained sample liquid continues to flow through chromatographic column；（4）After end of the sample, chromatographic column is rinsed with ultrasonic water；（5）After chromatography column equilibration, chromatographic column is eluted using the mixed solution of second alcohol and water as eluent, detects purity；The collection liquid of purity qualification is merged, collection liquid is obtained；（6）Collection liquid is concentrated, concentrate is obtained；（7）Concentrate is recrystallized, RD and RM can be obtained；The invention discloses Super 200-X19 resins using ultrapure water as sample solution, and the mixed solution of second alcohol and water is eluent, and the RD in mother liquor sugar mixed liquor and RM after extracting to steviol glycoside are effectively extracted.
Description
Technical field
The present invention relates to the preparation methods of high-purity steviosides RD and RM a kind of, belong to native chemical field.
Background technique
STEVIA REBAUDIANA originates in Paraguayan Guarani, and the beginning of the thirties in last century has scientific research personnel to extract from its leaf and has
Substance, that is, steviol glycoside of sweet taste.Steviol glycoside contains the tetracyclic diterpene class monomer there are many heterogeneity, according to different degrees of
Available different degrees of sweet taste mouthfeel after glycosylation modified.The stevioside of content relative abundance in stevioside glycosides compound
（Stevioside, STV）, content rebaudioside-A (RA) etc. be widely used to the fields such as beverage, food, flavouring, dairy products.Though
Right stevioside and content rebaudioside-A (RA) have high sugariness, but in mouthfeel there is also except sweet taste with for rear bitter taste, compare it
Under, rebaudioside D (RD) and rebaudioside M (RM) have better mouthfeel characteristic.
It mainly looks after the research of the method for purification of one-components such as STV, RA in steviol glycoside in the world at present, therefore exists
The mother liquor sugar of a large amount of steviol glycoside crystallization（Turn brilliant mother liquor sugar after extracting RA, STV）It needs to handle.If stevia rebaudianum can be utilized
Glucosides mother liquor sugar is raw material, continues to extract RD and RM, then fully using raw material and can obtain bigger economy
Benefit.There is Chinese patent（CN201711154894.X）Provide recrystallization method altogether：Successively using ethyl alcohol and methanol to mother
Liquid sugar dry powder is recrystallized, but a large amount of methanol and ethyl alcohol must be used during this, then is necessarily led to a large amount of organic molten
Agent waste liquid, and recrystallization process needs to carry out repeatedly, process is cumbersome and energy consumption is larger, is unfavorable for carrying out industrialized production.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, provides the preparation side of a kind of high-purity steviosides RD and RM
Method, to solve problems of the prior art.
To achieve the above object, the technical solution adopted by the present invention is as follows：
A kind of preparation method of high-purity steviosides RD and RM, specific step is as follows：The wherein relationship of component.
（1）Chromatographic column fills column, rinses：It by resin dispersion in the mixed solution of second alcohol and water, stirs evenly, and is packed into extremely
In chromatographic column, compacting chromatographic column bed is rinsed with the mixed solution of second alcohol and water and impregnates 2h, ultrapure water to efflux is without alcohol
Taste；
（2）Sample preparation：It takes steviol glycoside mother liquor sugar dope and is diluted with ultrapure water, mother liquor sugar dilution is made, it is spare；
（3）Loading：By step（2）Obtained sample liquid continues to flow through chromatographic column；
（4）Balance：After end of the sample, chromatographic column is rinsed with ultrasonic water；
（5）Elution：After chromatography column equilibration, chromatographic column is eluted using the mixed solution of second alcohol and water as eluent, root
According to UV detection case, efflux is collected, detects purity；The collection liquid of purity qualification is merged, collection liquid is obtained；
（6）Concentration：Collection liquid is concentrated, concentrate is obtained；
（7）Recrystallization：Concentrate is recrystallized, RD and RM can be obtained；
As an improvement of the present invention, the step（1）Middle resin is Super 200-X19 sphere material.
As an improvement of the present invention, the step（1）The volume ratio of second alcohol and water in the mixed solution of second alcohol and water
For 1-89:9；The concentration of ethyl alcohol is 90% in the mixed solution of second alcohol and water.
As an improvement of the present invention, the step（1）The middle mixed solution with second alcohol and water rinses the speed of chromatographic column
The column volume that degree is 1-4 times per hour.
As an improvement of the present invention, the step（2）The concentration of middle mother liquor sugar dilution is 2-50%.
As an improvement of the present invention, the step（3）Speed of the middle sample liquid Jing Guo chromatographic column is 1-4 times per hour
Column volume.
As an improvement of the present invention, the step（3）Center pillar volume of resins and the volume ratio of mother liquor sugar dope are
100:1-4。
As an improvement of the present invention, the step（4）The volume of middle ultrasound water is 1-3 times of column volume.
As an improvement of the present invention, the step（5）The volume ratio of second alcohol and water in the mixed solution of second alcohol and water
For 1-21:9.
As an improvement of the present invention, the step（5）The mixed solution of middle second alcohol and water is to wash to chromatographic column
When de-, speed is 1-4 times of column volume per hour.
The technical scheme is that the Super 200-X19 tree produced using Nanjing Gen Shan Biotechnology Co., Ltd
Rouge, the resin are the polystyrene series sphere materials of crosslinking, can achieve the purpose for extracting RD and RM；Its process includes will
The resin is packed into chromatographic column as stationary phase, the mother liquor sugar sample containing RD, RM to be separated is flowed through chromatographic column, then again
The RD and RM that are adsorbed in Super 200-X19 solid phase are eluted.
Due to using the above technology, the present invention compared with the prior art, is had the advantage that as follows：
The invention discloses Super 200-X19 resins can be using ultrapure water as sample solution, and the mixed solution of second alcohol and water is to wash
De- liquid, RD in mother liquor sugar mixed liquor and RM after extracting to steviol glycoside are effectively extracted, and are had good selectivity,
It is high-efficient, favorable reproducibility, it is at low cost, be easy industrialization the advantages that, avoid during use a large amount of organic solvents.
Specific embodiment
With reference to embodiment, the present invention is furture elucidated.
Embodiment 1：
Preparation of samples：34.54 mL of mother liquor sugar dope will be weighed, 20% concentration is diluted to ultrapure water；
Purifying：Using 50 × 440 mm glass columns, Super 200-X19 resin（Nanjing Gen Shan Biotechnology Co., Ltd）For
Separating medium, 863.5 mL of packed column volume rinse chromatographic column with 90% ethyl alcohol and water mixed solution of 2 times of column volumes and impregnate 2h
Afterwards, then with 3 times of column volume ultrapure water chromatographic columns；By sample with the continuous loading of flow velocity of 4 times of column volumes per hour, loading knot
Shu Hou is gone to rinse chromatographic column with the ultrapure water of 1 times of column volume；Then with 30% ethyl alcohol and water mixed solution with 4 times of cylinders per hour
Long-pending speed elution, is in charge of collection according to UV detection case.The collection liquid of purity qualification is merged, is just concentrated, recrystallize can
Obtain 20.5g RD and RM.
Embodiment 2：
Preparation of samples：3.19 mL of mother liquor sugar dope will be weighed, 15% concentration is diluted to ultrapure water；
Purifying：Using 26 × 300 mm glass columns, Super 200-X19 resin（Nanjing Gen Shan Biotechnology Co., Ltd）For
Separating medium, 159.5 mL of packed column volume rinse chromatographic column with 90% ethyl alcohol and water mixed solution of 1 times of column volume and impregnate 2h
Afterwards, with 4 times of column volume ultrapure water chromatographic columns；By sample with the continuous loading of flow velocity of 2 times of column volumes per hour, end of the sample
Afterwards, it is gone to rinse chromatographic column with the ultrapure water of 2 times of column volumes；Then with 40% ethyl alcohol and water mixed solution with 2 times of column volumes per hour
Speed elution, collection is in charge of according to UV detection case.The collection liquid of purity qualification is merged, is just concentrated, recrystallized and can obtain
To 2.75g RD and RM.
Embodiment 3：
Preparation of samples：0.603 mL of mother liquor sugar dope will be weighed, 50% concentration is diluted to ultrapure water；
Purifying：Using 16 × 100 mm glass columns, Super 200-X19 resin（Nanjing Gen Shan Biotechnology Co., Ltd）For
Separating medium, 20.1 mL of packed column volume rinse chromatographic column with 90% ethyl alcohol and water mixed solution of 4 times of column volumes and impregnate 2h
Afterwards, with 2 times of column volume ultrapure water chromatographic columns；By sample with the continuous loading of flow velocity of 1 times of column volume per hour, end of the sample
Afterwards, it is gone to rinse chromatographic column with the ultrapure water of 3 times of column volumes；Then with 30% ethyl alcohol and water mixed solution with 1 times of column volume per hour
Speed elution, collection is in charge of according to UV detection case.The collection liquid of purity qualification is merged, is just concentrated, recrystallized and can obtain
To 0.5g RD and RM.
Above-described embodiment is only the preferred technical solution of the present invention, and is not construed as limitation of the invention, the present invention
Protection scope should with claim record technical solution, including claim record technical solution in technical characteristic etc.
It is protection scope with alternative, i.e., equivalent replacement within this range is improved, also within protection scope of the present invention.
Claims (10)
1. a kind of preparation method of high-purity steviosides RD and RM, which is characterized in that specific step is as follows：
（1）Chromatographic column fills column, rinses：It by resin dispersion in the mixed solution of second alcohol and water, stirs evenly, and is packed into chromatography
In column, compacting chromatographic column bed is rinsed with the mixed solution of second alcohol and water and impregnates 2h, ultrapure water to efflux is without alcohol taste；
（2）Sample preparation：It takes steviol glycoside mother liquor sugar dope and is diluted with ultrapure water, mother liquor sugar dilution is made, it is spare；
（3）Loading：By step（2）Obtained sample liquid continues to flow through chromatographic column；
（4）Balance：After end of the sample, chromatographic column is rinsed with ultrasonic water；
（5）Elution：After chromatography column equilibration, chromatographic column is eluted using the mixed solution of second alcohol and water as eluent, root
According to UV detection case, efflux is collected, detects purity；The collection liquid of purity qualification is merged, collection liquid is obtained；
（6）Concentration：Collection liquid is concentrated, concentrate is obtained；
（7）Recrystallization：Concentrate is recrystallized, RD and RM can be obtained.
2. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（1）Middle resin is Super 200-X19.
3. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（1）The volume ratio of second alcohol and water is 1-89 in the mixed solution of second alcohol and water:9；Ethyl alcohol in the mixed solution of second alcohol and water
Concentration is 90%.
4. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（1）The middle mixed solution with second alcohol and water rinses the column volume that the speed of chromatographic column is 1-4 times per hour.
5. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（2）The concentration of middle mother liquor sugar dilution is 2-50%.
6. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（3）Speed of the middle sample liquid Jing Guo chromatographic column is 1-4 times of column volume per hour.
7. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（3）Center pillar volume of resins and the volume ratio of mother liquor sugar dope are 100:1-4.
8. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（4）The volume of middle ultrasound water is 1-3 times of column volume.
9. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：The step
Suddenly（5）The volume ratio of second alcohol and water is 1-21 in the mixed solution of second alcohol and water:9.
10. the preparation method of high-purity steviosides RD and RM according to claim 1 a kind of, it is characterised in that：It is described
Step（5）The mixed solution of middle second alcohol and water is when eluting to chromatographic column, and speed is 1-4 times of column volume per hour.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229201A (en) * | 2019-06-25 | 2019-09-13 | 浙江天草生物科技股份有限公司 | A kind of process preparing high-purity steviosides RM |
| CN111187316A (en) * | 2020-02-14 | 2020-05-22 | 南京全凯生物基材料研究院有限公司 | Method for extracting rebaudioside D and rebaudioside M from stevioside mother liquor |
| CN115536715A (en) * | 2022-08-17 | 2022-12-30 | 浙江天草生物科技股份有限公司 | Method for extracting stevioside RD |
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| CN107105733A (en) * | 2014-09-26 | 2017-08-29 | 谱赛科美国股份有限公司 | Stevia components, production method and purposes |
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|---|---|---|---|---|
| WO2011112892A1 (en) * | 2010-03-12 | 2011-09-15 | Purecircle Usa Inc. | High-purity steviol glycosides |
| CN104684414A (en) * | 2011-12-19 | 2015-06-03 | 可口可乐公司 | Method for purifying steviol glycosides and use thereof |
| CN104151378A (en) * | 2014-08-12 | 2014-11-19 | 济南汉定生物工程有限公司 | Rebaudioside M purification method |
| CN107105733A (en) * | 2014-09-26 | 2017-08-29 | 谱赛科美国股份有限公司 | Stevia components, production method and purposes |
| CN105503975A (en) * | 2016-01-08 | 2016-04-20 | 谱赛科（江西）生物技术有限公司 | Method for synthesizing stevioside RM through cation exchange resin catalyzed synthesis |
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| CN110229201A (en) * | 2019-06-25 | 2019-09-13 | 浙江天草生物科技股份有限公司 | A kind of process preparing high-purity steviosides RM |
| CN111187316A (en) * | 2020-02-14 | 2020-05-22 | 南京全凯生物基材料研究院有限公司 | Method for extracting rebaudioside D and rebaudioside M from stevioside mother liquor |
| CN115536715A (en) * | 2022-08-17 | 2022-12-30 | 浙江天草生物科技股份有限公司 | Method for extracting stevioside RD |
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