JPH02131592A - 甘味料の製造方法 - Google Patents
甘味料の製造方法Info
- Publication number
- JPH02131592A JPH02131592A JP63247371A JP24737188A JPH02131592A JP H02131592 A JPH02131592 A JP H02131592A JP 63247371 A JP63247371 A JP 63247371A JP 24737188 A JP24737188 A JP 24737188A JP H02131592 A JPH02131592 A JP H02131592A
- Authority
- JP
- Japan
- Prior art keywords
- glucosyl
- galactosyl
- reaction
- stevioside
- group
- 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.)
- Granted
Links
- 235000003599 food sweetener Nutrition 0.000 title claims description 14
- 239000003765 sweetening agent Substances 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- -1 β-galactosyl Chemical group 0.000 claims description 45
- 235000019202 steviosides Nutrition 0.000 claims description 39
- 229940013618 stevioside Drugs 0.000 claims description 29
- 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 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims 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 claims description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 13
- 239000008103 glucose Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000004383 Steviol glycoside Substances 0.000 claims description 10
- 235000019411 steviol glycoside Nutrition 0.000 claims description 10
- 229930182488 steviol glycoside Natural products 0.000 claims description 10
- 150000008144 steviol glycosides Chemical class 0.000 claims description 10
- 108010005774 beta-Galactosidase Proteins 0.000 claims description 8
- 229930182830 galactose Natural products 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000007900 aqueous suspension Substances 0.000 claims description 6
- 125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 102000005936 beta-Galactosidase Human genes 0.000 claims 1
- 230000000415 inactivating effect Effects 0.000 claims 1
- 238000006911 enzymatic reaction Methods 0.000 description 31
- 239000000047 product Substances 0.000 description 22
- 108090000790 Enzymes Proteins 0.000 description 17
- 102000004190 Enzymes Human genes 0.000 description 17
- 229940088598 enzyme Drugs 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000019640 taste Nutrition 0.000 description 14
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 102100026189 Beta-galactosidase Human genes 0.000 description 6
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000006276 transfer reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 241000194107 Bacillus megaterium Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 244000228451 Stevia rebaudiana Species 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- 241000193752 Bacillus circulans Species 0.000 description 2
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 2
- 102100022624 Glucoamylase Human genes 0.000 description 2
- 108010059881 Lactase Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000178960 Paenibacillus macerans Species 0.000 description 2
- 241001092459 Rubus Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- FYGDTMLNYKFZSV-SKJAFLLWSA-N alpha-D-Galp-(1->4)-alpha-D-Galp-(1->4)-beta-D-Galp Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@@H](CO)O[C@H](O[C@H]2[C@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-SKJAFLLWSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 229940116108 lactase Drugs 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 238000009630 liquid culture Methods 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 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 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 229920000310 Alpha glucan Polymers 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241001149409 Cystobasidium minutum Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 101100489736 Fagopyrum esculentum UGT708C1 gene Proteins 0.000 description 1
- 241000193385 Geobacillus stearothermophilus Species 0.000 description 1
- 241000580812 Hasegawazyma lactosa Species 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241001603151 Philus Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000220222 Rosaceae Species 0.000 description 1
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Landscapes
- Seasonings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63247371A JPH02131592A (ja) | 1988-10-03 | 1988-10-03 | 甘味料の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63247371A JPH02131592A (ja) | 1988-10-03 | 1988-10-03 | 甘味料の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02131592A true JPH02131592A (ja) | 1990-05-21 |
| JPH0577397B2 JPH0577397B2 (enrdf_load_stackoverflow) | 1993-10-26 |
Family
ID=17162435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63247371A Granted JPH02131592A (ja) | 1988-10-03 | 1988-10-03 | 甘味料の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02131592A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1295533A1 (en) * | 2001-09-21 | 2003-03-26 | Dainippon Ink And Chemicals, Inc. | Sweetener and process for producing the same |
| CN102250990A (zh) * | 2011-05-31 | 2011-11-23 | 江南大学 | 用β-半乳糖苷酶催化水解甜菊糖苷制备悬钩子苷的方法 |
| WO2019193358A1 (en) * | 2018-04-04 | 2019-10-10 | Optibiotix Limited | Prebiotic compositions and methods of production thereof |
| US12213501B2 (en) | 2018-04-04 | 2025-02-04 | Optibiotix Limited | Methods for modifying high intensity sweetener glycosides |
-
1988
- 1988-10-03 JP JP63247371A patent/JPH02131592A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1295533A1 (en) * | 2001-09-21 | 2003-03-26 | Dainippon Ink And Chemicals, Inc. | Sweetener and process for producing the same |
| CN100455209C (zh) * | 2001-09-21 | 2009-01-28 | 大日本油墨化学工业株式会社 | 甜味料及其制备方法 |
| CN102250990A (zh) * | 2011-05-31 | 2011-11-23 | 江南大学 | 用β-半乳糖苷酶催化水解甜菊糖苷制备悬钩子苷的方法 |
| WO2019193358A1 (en) * | 2018-04-04 | 2019-10-10 | Optibiotix Limited | Prebiotic compositions and methods of production thereof |
| US12213501B2 (en) | 2018-04-04 | 2025-02-04 | Optibiotix Limited | Methods for modifying high intensity sweetener glycosides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0577397B2 (enrdf_load_stackoverflow) | 1993-10-26 |
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