CN105597843A - Method for removing steviolbiosude (SB) through anion exchange resin - Google Patents
Method for removing steviolbiosude (SB) through anion exchange resin Download PDFInfo
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- CN105597843A CN105597843A CN201510989865.XA CN201510989865A CN105597843A CN 105597843 A CN105597843 A CN 105597843A CN 201510989865 A CN201510989865 A CN 201510989865A CN 105597843 A CN105597843 A CN 105597843A
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- exchange resin
- anion exchange
- steviol glycoside
- anion
- washed
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- 239000003957 anion exchange resin Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 17
- 229920005989 resin Polymers 0.000 claims abstract description 17
- 235000019202 steviosides Nutrition 0.000 claims description 40
- 239000004383 Steviol glycoside Substances 0.000 claims description 35
- 235000019411 steviol glycoside Nutrition 0.000 claims description 35
- 229930182488 steviol glycoside Natural products 0.000 claims description 35
- 150000008144 steviol glycosides Chemical class 0.000 claims description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 13
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 229930182478 glucoside Natural products 0.000 claims description 8
- 150000008131 glucosides Chemical class 0.000 claims description 8
- 238000002835 absorbance Methods 0.000 claims description 5
- 238000005349 anion exchange Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 244000228451 Stevia rebaudiana Species 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 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 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 235000013373 food additive Nutrition 0.000 abstract description 2
- 239000002778 food additive Substances 0.000 abstract description 2
- 235000003599 food sweetener Nutrition 0.000 abstract description 2
- 239000003765 sweetening agent Substances 0.000 abstract description 2
- 206010013911 Dysgeusia Diseases 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000011344 liquid material Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 229940013618 stevioside Drugs 0.000 description 5
- 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 5
- 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 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- OMHUCGDTACNQEX-OSHKXICASA-N Steviolbioside Natural products 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 2
- JLPRGBMUVNVSKP-AHUXISJXSA-M chembl2368336 Chemical compound [Na+].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 JLPRGBMUVNVSKP-AHUXISJXSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 241000189115 Catananche Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- FEQSXXYJWMCXJX-FMYGVZKHSA-N fusicoccin j Chemical compound O([C@H]1[C@H](O)[C@H](C)[C@@H]\2CC[C@@H](C/2=C/[C@@]2(C)[C@@H](O)CC(=C21)C(C)C)COC)[C@H]1O[C@H](COC(C)(C)C=C)[C@@H](O)[C@H](O)[C@H]1O FEQSXXYJWMCXJX-FMYGVZKHSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- -1 stevioside glycosides Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/02—Column or bed processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention relates to the field of extraction of natural efficient sweeteners in the field of food additives, and provides a method for removing steviolbiosude (SB) through anion exchange resin. According to the method, an SB-containing steviolbiosude solution is adsorbed by the treated exchange resin, and through selective adsorption of the anion exchange resin to the SB, the SB content in the solution can be reduced to below 0.5%. By the method, on one hand, the mouth feel of a product can be improved and bad aftertaste can be removed; on the other hand, an SB component in a high-SB liquid material can be removed to facilitate follow-up processing.
Description
Technical field
The present invention relates to efficiency natural sweetener in food additives field and extract field, particularly remove the side of steviol glycoside SBMethod.
Background technology
Steviol glycoside, claims again stevioside glycosides, be a kind of from the leaf of catananche's STEVIA REBAUDIANA, extract containing Multiple componentsThe mixture of diterpene glucoside, according to the division of natural plants chemistry, belongs to the glucoside of tetracyclic diterpene, and it is with high sugariness, low-heatThe features such as amount, safety non-toxic are subject to people's favor gradually, are widely used at present the industries such as food, medicine, daily chemical industry.The sugariness of stevioside and mouthfeel depend on its glucosides component and content, in 9 kinds of known components, comprise Lay bud enlightening glycosidesA (RebaudiosideA is called for short RA), stevioside (Stevioside is called for short ST), steviolbioside (Steviolbioside letterClaim SB) etc., wherein RA and the ST relative amount in total glucosides is higher, and sugariness is the highest, is equivalent to 200～350 times of sucrose,Sweet taste characteristic is also close with sucrose, is a kind of the novel of high sugariness, the feature such as low in calories, soluble, heat-resisting, stable that haveNatural sweetener. SB sugariness is only 10～15 times of sucrose, and rear pained highly seasoned, containing bad pleasant impression. Therefore, utilize resin to incite somebody to actionSB component in steviol glycoside has very important meaning for improving products taste; On the other hand, remove in high SB feed liquidSB component, facilitates subsequent treatment.
In general steviol glycoside product, all contain SB, because SB sugariness is low, rear bitterness is highly seasoned, containing bad pleasant impression. Mostly sharp at presentWith the purifying such as recrystallization method, enzyme process stevioside, and there is the bringing into of organic solvent in recrystallization technology, energy consumption is high, clearance is lowShortcoming.
Summary of the invention
The object of the invention is to overcome enzyme process to enzyme purity and actively require high, operation to control difficult problem, provide a kind of cloudy fromSub-exchange resin removes the method for steviol glycoside SB, overcome the bringing into of organic solvent in recrystallization technology, energy consumption is high, clearanceLow shortcoming, has reaction condition simply controlled, and pollution-free, cost is low, clearance advantages of higher.
Technical problem of the present invention is mainly solved by following technical proposals:
Anion exchange resin is removed a method of steviol glycoside SB, it is characterized in that: under 10～40 DEG C of temperature conditions, getAnion exchange resin packs in chromatographic column, by the steviol glycoside feed liquid containing SB, adsorbs by anion-exchange column, collects and flows outLiquid stops charging in the time that efflux jumps than absorbance, and by efflux concentrate drying, the steviol glycoside that obtains SB content≤0.5% producesProduct.
Concrete, described anion exchange resin is macroporous type or gel-type anion exchange resin.
Concrete, described steviol glycoside feed liquid is taking steviol glycoside as solute, the mixed solution that water is solvent, this steviol glycoside materialLiquid concentration is 15～300g/L, and PH is 3.5～6.
Concrete, described steviol glycoside feed liquid is passed through anion-exchange column with the speed of 0.2～4BV/h.
Concrete, described anion exchange resin needs to do pretreatment packing into before chromatographic column, adopts the NaOH water of 3.5BV5%Solution, by anion exchange resin, is washed to PH < 9; Pass through anion exchange resin, washing with the hydrochloric acid of 3.5BV5% againTo PH > 5; Finally pass through anion exchange resin with the sodium hydrate aqueous solution of 3.5BV5%, be washed to PH < 9.
Its operation principle is: under 10～40 DEG C of conditions, get processed good exchanger resin and pack in chromatographic column, blade diameter length ratio is1:8～1:2, it is 15～300g/L that high SB content steviol glycoside mother liquor sugar is mixed with to concentration, the feed liquid that PH is 4～6, by feed liquidBe adsorbed to out sweetly with the speed of 0.2～2BV/H by chromatographic column, in the time that efflux jumps than absorbance, stop charging. To flowFluid concentrate drying, can obtain the steviol glycoside product of SB content below 0.5%. Adopt the hydroxide that concentration is 0.5～10%Sodium solution carries out wash-out to pillar, and consumption is 1～5 times of resin volume, collects eluent, and eluent, through subsequent treatment, can obtainObtain the steviol glycoside byproduct of high SB content.
Utilize the selective absorption of anion exchange resin to steviol glycoside component S B, the concentration of feed liquid and pH value are handed over anionThe adsorption capacity of changing resin has certain influence, excessive or too small adsorption capacity and the efficiency that all can reduce resin of concentration.
Beneficial effect of the present invention: the steviol glycoside product SB content making by said method is below 0.5%. With there is no warpCross removal SB steviol glycoside and compare, this product sweetness is higher, and mouthfeel is purer, without bad pleasant impression, has wide market prospects.Meanwhile, this method can be avoided a large amount of organic solvents that use recrystallization method required, and can overcome enzyme process to enzyme purity and active wantingAsk problem high, that operation control is difficult. Have reaction condition simply controlled, pollution-free, cost is low, clearance advantages of higher.
Brief description of the drawings
Fig. 1 is the efficient liquid phase chromatographic analysis collection of illustrative plates of feed liquid former state in the embodiment of the present invention 1;
Fig. 2 is the efficient liquid phase chromatographic analysis collection of illustrative plates of efflux 1 in the embodiment of the present invention 1.
Detailed description of the invention
Below technical scheme of the present invention is described in further detail.
Embodiment 1
Feed concentration: 50g/L
Under 25 DEG C of conditions, to get 04D macroporous type anion exchange resin 150mL and pack in chromatographic column, blade diameter length ratio is 1:4, pressesFollowing steps are carried out pretreatment to resin: by resin, be washed to PH < 9 with the NaOH of 3.5BV5%; Use again 3.5BV5%Hydrochloric acid by resin, be washed to PH > 5; Finally pass through resin with the NaOH of 3.5BV5%, be washed to PH < 9. WillHigh SB content steviol glycoside solution (detecting total glucosides amount through efficient liquid phase chromatographic analysis is 90.05%, and wherein SB content is 4.14%)Adding water and being mixed with concentration is 50g/L, and the feed liquid that PH is 5, is adsorbed to out with the speed of 0.3BV/h feed liquid by chromatographic columnSweet, Fractional Collections efflux, while jumping, stops charging in efflux than absorbance.
Efflux 1 to efflux 5 is mixed, i.e. comprehensive sample, obtains SB content and is 0.07% steviol glycoside product, treating capacityReach 710g/L.
Adopt the sodium hydroxide solution of 300mL5% to carry out wash-out to pillar, collect eluent, eluent, through subsequent treatment, obtainsSB content is 70.57%, the steviol glycoside byproduct that total glucosides amount is 72.45%.
Embodiment 2
Feed concentration: 150g/L
Under 25 DEG C of conditions, to get 07D gel-type anion exchange resin 100mL and pack in chromatographic column, blade diameter length ratio is 1:8, pressesFollowing steps are carried out pretreatment to resin: by resin, be washed to PH < 9 with the NaOH of 3.5BV5%; Use again 3.5BV5%Hydrochloric acid by resin, be washed to PH > 5; Finally pass through resin with the NaOH of 3.5BV5%, be washed to PH < 9. WillHigh SB content steviol glycoside solution (detecting total glucosides amount through efficient liquid phase chromatographic analysis is 89.84%, and wherein SB content is 5.09%)Adding water and being mixed with concentration is 150g/L, and the feed liquid that PH is 5, is adsorbed to out with the speed of 0.2BV/H feed liquid by chromatographic columnSweet, Fractional Collections efflux, in the time that efflux jumps than absorbance, stops charging.
Efflux 1 to efflux 5 is mixed, i.e. comprehensive sample, obtains SB content and is 0.07% steviol glycoside product, treating capacityReach 727g/L.
Adopt the sodium hydroxide solution of 300mL2% to carry out wash-out to pillar, collect eluent, eluent, through subsequent treatment, obtainsSB content is 73.24%, the steviol glycoside byproduct that total glucosides amount is 75.19%.
The present embodiment is the embodiment of example of the present invention, for those skilled in the art, the invention disclosesOn the basis of application process and principle, be easy to make various types of improvement or distortion, and it is above-mentioned concrete to be not limited only to the present inventionThe described structure of embodiment, therefore previously described mode is preferred version, and does not have restrictive meaning, allThat the equivalence of doing according to the present invention changes and amendment, all in the scope protection domain of the claims in the present invention book.
Claims (5)
1. anion exchange resin is removed a method of steviol glycoside SB, it is characterized in that: under 10～40 DEG C of temperature conditions,Get anion exchange resin and pack in chromatographic column, by the steviol glycoside feed liquid containing SB, adsorb by anion-exchange column, collectEfflux stops charging in the time that efflux jumps than absorbance, by efflux concentrate drying, obtains the stevia rebaudianum of SB content≤0.5%Glucosides product.
2. a kind of anion exchange resin according to claim 1 is removed the method for steviol glycoside SB, it is characterized in that:Described anion exchange resin is macroporous type or gel-type anion exchange resin.
3. a kind of anion exchange resin according to claim 1 is removed the method for steviol glycoside SB, it is characterized in that:Described steviol glycoside feed liquid is taking steviol glycoside as solute, the mixed solution that water is solvent, and this steviol glycoside feed concentration is15～300g/L, PH is 3.5～6.
4. a kind of anion exchange resin according to claim 1 is removed the method for steviol glycoside SB, it is characterized in that:Described steviol glycoside feed liquid is passed through anion-exchange column with the speed of 0.2～4BV/h.
5. a kind of anion exchange resin according to claim 1 is removed the method for steviol glycoside SB, it is characterized in that:Described anion exchange resin needs to do pretreatment packing into before chromatographic column, the sodium hydrate aqueous solution that adopts 3.5BV5% by cloudy fromSub-exchange resin, is washed to PH < 9; Pass through anion exchange resin with the hydrochloric acid of 3.5BV5% again, be washed to PH > 5; ?Pass through anion exchange resin with the sodium hydrate aqueous solution of 3.5BV5% afterwards, be washed to PH < 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510989865.XA CN105597843A (en) | 2015-12-24 | 2015-12-24 | Method for removing steviolbiosude (SB) through anion exchange resin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510989865.XA CN105597843A (en) | 2015-12-24 | 2015-12-24 | Method for removing steviolbiosude (SB) through anion exchange resin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632541A (en) * | 2016-12-26 | 2017-05-10 | 晨光生物科技集团股份有限公司 | Method for refining and purifying steviolbioside |
| CN109354596A (en) * | 2018-10-09 | 2019-02-19 | 山东奥晶生物科技有限公司 | A kind of preparation method of efficient steviol glycoside |
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|---|---|---|---|---|
| CN1192447A (en) * | 1998-02-18 | 1998-09-09 | 南开大学 | Adsorption resin method for conectrating and separating vegetable baudy glucoside from stevioside |
| CN101366496A (en) * | 2008-09-17 | 2009-02-18 | 无锡绿色分离应用技术研究所有限公司 | Method for separating and purifying Stevioside RA and SS from Stevia rebaudiana Bertoni concentrated liquor |
| CN102050850A (en) * | 2009-10-30 | 2011-05-11 | 兴化格林生物制品有限公司 | New extraction technology of stevioside and high purity rebaudioside A |
| CN102816193A (en) * | 2012-09-13 | 2012-12-12 | 江南大学 | Method for extracting and purifying steviol glycoside from stevia rebaudiana aqueous extract by virtue of series resin column method |
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2015
- 2015-12-24 CN CN201510989865.XA patent/CN105597843A/en active Pending
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|---|---|---|---|---|
| CN1192447A (en) * | 1998-02-18 | 1998-09-09 | 南开大学 | Adsorption resin method for conectrating and separating vegetable baudy glucoside from stevioside |
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| CN109354596A (en) * | 2018-10-09 | 2019-02-19 | 山东奥晶生物科技有限公司 | A kind of preparation method of efficient steviol glycoside |
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Application publication date: 20160525 |