WO2015094688A1 - Stabilized steviol glycoside in concentrated syrup - Google Patents
Stabilized steviol glycoside in concentrated syrup Download PDFInfo
- Publication number
- WO2015094688A1 WO2015094688A1 PCT/US2014/068552 US2014068552W WO2015094688A1 WO 2015094688 A1 WO2015094688 A1 WO 2015094688A1 US 2014068552 W US2014068552 W US 2014068552W WO 2015094688 A1 WO2015094688 A1 WO 2015094688A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- syrup concentrate
- rebaudioside
- methyl cellulose
- acid
- polyoxyethylene
- Prior art date
Links
- 235000020357 syrup Nutrition 0.000 title claims abstract description 84
- 239000006188 syrup Substances 0.000 title claims abstract description 84
- 235000019202 steviosides Nutrition 0.000 title claims description 56
- 239000004383 Steviol glycoside Substances 0.000 title claims description 50
- 235000019411 steviol glycoside Nutrition 0.000 title claims description 50
- 229930182488 steviol glycoside Natural products 0.000 title claims description 50
- 150000008144 steviol glycosides Chemical class 0.000 title claims description 50
- 235000008504 concentrate Nutrition 0.000 claims abstract description 76
- 239000012141 concentrate Substances 0.000 claims abstract description 76
- 239000000654 additive Substances 0.000 claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 54
- DRSKVOAJKLUMCL-MMUIXFKXSA-N u2n4xkx7hp 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]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DRSKVOAJKLUMCL-MMUIXFKXSA-N 0.000 claims abstract description 52
- 230000000996 additive effect Effects 0.000 claims abstract description 51
- 239000003381 stabilizer Substances 0.000 claims abstract description 44
- 230000002378 acidificating effect Effects 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000000243 solution Substances 0.000 claims description 77
- 229930006000 Sucrose Natural products 0.000 claims description 72
- 239000005720 sucrose Substances 0.000 claims description 72
- 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 claims description 66
- -1 polyoxyethylene octyl phenyl ether Polymers 0.000 claims description 48
- 229920000609 methyl cellulose Polymers 0.000 claims description 36
- 235000010981 methylcellulose Nutrition 0.000 claims description 36
- 239000001923 methylcellulose Substances 0.000 claims description 36
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 27
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 27
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 27
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 27
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 27
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 26
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- 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 claims description 20
- 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 19
- 239000001512 FEMA 4601 Substances 0.000 claims description 16
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 16
- 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 claims description 16
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 16
- 235000019203 rebaudioside A Nutrition 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
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- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 claims description 8
- 235000021314 Palmitic acid Nutrition 0.000 claims description 8
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 8
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- 125000006353 oxyethylene group Chemical group 0.000 claims description 7
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- 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 6
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 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 claims 1
- 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 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 abstract description 9
- 235000009508 confectionery Nutrition 0.000 description 12
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- 235000019634 flavors Nutrition 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 7
- 229930182470 glycoside Natural products 0.000 description 7
- 150000002338 glycosides Chemical class 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000011550 stock solution Substances 0.000 description 7
- NLMKTBGFQGKQEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hexadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO NLMKTBGFQGKQEV-UHFFFAOYSA-N 0.000 description 6
- UDKCHVLMFQVBAA-UHFFFAOYSA-M Choline salicylate Chemical compound C[N+](C)(C)CCO.OC1=CC=CC=C1C([O-])=O UDKCHVLMFQVBAA-UHFFFAOYSA-M 0.000 description 6
- 244000228451 Stevia rebaudiana Species 0.000 description 6
- 230000006641 stabilisation Effects 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- 244000215068 Acacia senegal Species 0.000 description 5
- 229920003091 Methocel™ Polymers 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 235000019223 lemon-lime Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 230000008685 targeting Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 3
- 239000007979 citrate buffer Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000544066 Stevia Species 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QSIDJGUAAUSPMG-CULFPKEHSA-N steviolmonoside Chemical compound 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]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QSIDJGUAAUSPMG-CULFPKEHSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 235000016795 Cola Nutrition 0.000 description 1
- 235000011824 Cola pachycarpa Nutrition 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 235000012098 RTD tea Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001222723 Sterna Species 0.000 description 1
- QFVOYBUQQBFCRH-UHFFFAOYSA-N Steviol Natural products C1CC2(C3)CC(=C)C3(O)CCC2C2(C)C1C(C)(C(O)=O)CCC2 QFVOYBUQQBFCRH-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 210000000692 cap cell Anatomy 0.000 description 1
- 235000012174 carbonated soft drink Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000019543 dairy drink Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000015897 energy drink Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000008123 high-intensity sweetener Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 235000019533 nutritive sweetener Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000021572 root beer Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QFVOYBUQQBFCRH-VQSWZGCSSA-N steviol Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)CC1)C[C@H]2[C@@]2(C)[C@H]1[C@](C)(C(O)=O)CCC2 QFVOYBUQQBFCRH-VQSWZGCSSA-N 0.000 description 1
- 229940032084 steviol Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/36—Terpene glycosides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/045—Organic compounds containing nitrogen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
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- A23L29/05—Organic compounds containing phosphorus as heteroatom
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/055—Organic compounds containing sulfur as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/25—Exudates, e.g. gum arabic, gum acacia, gum karaya or tragacanth
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to steviol glycosides. More specifically, the present invention relates to providing steviol glycosides in concentrated syrup.
- Steviol glycosides are sweet-tasting compounds extracted from the stevia plant (Stevia rebaudiana Bertoni) that are of particular interest.
- WO2013/036366 describes a process for the preparation of highly soluble sweet glycosides from a Stevia rebaudiana Bertoni plant, and more particularly for preparation of highly soluble compositions containing rebaudioside D.
- This method for producing a sweetener comprises the steps of providing Stevia sweetener powder, solubilizing it in water under gradient temperature treatment conditions, to produce highly stable concentrated solution, and spray drying the highly stable concentrated solution to obtain a highly soluble Stevia sweetener powder.
- Steviol glycosides are sweet-tasting compounds extracted from the stevia plant (Stevia rebaudiana Bertoni).
- Rebaudioside A is one of the steviol glycosides that is widely used as a sweetener in beverages.
- Rebaudioside A has a sweetness potency of 250 times that of sucrose and an equilibrium solubility in water at about 8000 ppm.
- Rebaudioside A is known to have off-tastes, such as bitter, licorice, or lingering aftertaste.
- Blends of rebaudioside A and other steviol glycosides at specific ratios were found to significantly improve the taste quality over rebaudioside A alone.
- an acidic stabilized syrup concentrate containing rebaudioside B comprising:
- polyoxyethylene having from about 10 to about 100 oxyethylene repeating units that is etherifed with a C 16-19 alkyl alcohol;
- sucrose monoesters of lauric, palmitic or stearic acid sucrose monoesters of lauric, palmitic or stearic acid
- polysorbate comprising from about 20 to about 80 oxyethylene repeating units and esterified with a fatty acid selected from lauric acid, palmitic acid, stearic acid deoiled lecithins;
- the stabilizer additive is selected from the group consisting of polyoxyethylene (20) cetyl ether (such as Brij®58), polyoxyethylene (100) stearyl ether (such as Brij®S-100), polyoxyethylene (40) stearate (such as POE (40) stearate), tannic acid, a sucrose monoester of monopalmitate (such as Habo monoester P90), a sucrose monoester of palmitate/stearate having a ratio of stearate/palmitate of from 4: 1 to 1 :4 (such asquela® SP50, Sisierna® SP70, and Sisterna® PS750 ), polyoxyeihylenesofbitan monolaurate (such as Tween® 20), polyoxyeihylenesorbiian monopalmitate (such as Tween® 40), polyoxyethylenesorbitan monostearaie (such as Tween® 60), polyoxyethylene sorbitan monooleate (such as Tween®
- polyoxyethylene octyl phenyl ether Triton X-100
- sodium dodecyl sulfate sodium dodecyl sulfate
- methyl cellulose with molecular weight less than 100 such as Methocel' M El 5
- hydroxypropyl methyl cellulose such as Methocel 1 M E19
- deoiled lecithins such as Metarin CP and Lecigran 1000P
- gum Arabic and mixtures thereof.
- Acidic stabilized syrup concentrates made by the present method are particularly useful as precursors to beverages as "throw syrups" due to their stability and unique compositional profile.
- the surprising ability to solubilize larger amounts of the usually difficult to solubilize rebaudioside B permits preparation of syrups having unique and excellent flavor profiles.
- the present invention additionally provides acidic stabilized syrup concentrate compositions comprising rebaudioside B at a concentration of ai least 500 ppm and stabilizer additive selected from the group consisting of
- polyoxyethylene having from about 0 to about 100 oxyethylene repeating units that is etherifed with a C 6-19 alkyl alcohol;
- sucrose monoesters of lauric, palmitic or stearic acid sucrose monoesters of lauric, palmitic or stearic acid
- polysorbate comprising from about 20 to about 80 oxyethylene repeating units and esterified with a fatty acid selected from lauric acid, palmitic acid, stearic acid and oleic acid:
- the stabilizer additive of the acidic syrup concentrate is selected form the group consisting of polyoxyethylene (20) cetyl ether (such as Brij®58), polyoxyethylene (100) stearyl ether (such as Brij®S-100), polyoxyethylene
- palmitate/stearate having a ratio of stearate/palmitate of from 4: 1 to 1 :4 (such as Sisie na® SP50, Sisterna® SP70, and Si sterna® PS750 ), polyoxyethylenesorbitan monolaurate (such as Tween® 20), polyoxyethylenesorbitan monopalmitate (such as Tween® 40), polyoxyethylenesorbitan monostearate (such as Tween® 60), polyoxyethylene sorbitan monooleate (such as Tween® 80), polyoxyethylene octyl phenyl ether (Triton X-100), sodiimi dodecyl sulfate, methyl cellulose with molecular weight less than 100 (such as MethocelTM El 5), hyroxypropyl methyl cellulose (such as Methocel IM El 9), deoiled lecithins (such as Metarin CP and Lecigran 1000P), gum Arabic, and mixtures thereof.
- the stabilizer additive comprises sucrose monoester and methyl cellulose at a weight ratio of from about 1 : 1 to aboiit 5: 1 sucrose monoester to methyl cellulose.
- the stabilizer additive comprises sucrose monoester and methyl cellulose at a weight ratio of from about 2: 1 to about 4: 1 sucrose monoester to methyl cellulose,
- the stabilizer additive comprises sucrose monoester and methyl cellulose at a weight ratio of about 3: 1 sucrose monoester to methyl cellulose.
- the sucrose monoester is sucrose monoester of monopalmitate and the methyl cellulose is hydroxypropyl methyl cellulose.
- the method comprises the step a) of dissolving rebaudioside B in a solution having a pH of from about 7 to 9, or in another embodiment from about 7 to 8, to form a syrup concentrate having a rebaudioside B concentration of at least 500 ppm.
- the syrup concentrate has a rebaudioside B
- the syrup concentrate has a rebaudioside B concentration of from about 600 ppm to about 1300 ppm. In an embodiment, the syrup concentrate has a rebaudioside B
- the syrup concentrate has a rebaudioside B concentration of from about 800 ppm to about 1000 ppm.
- the syrup concentrate of step a) further comprises one or more additional steviol glycosides.
- steviol glycosides include rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, stevioside,
- the syrup concentrate of step a) further comprises one or more of rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, stevioside, stevioibioside, and ste iolmonoside.
- the syrup concentrate of step a) further comprises rebaudioside A and rebaudioside D.
- a stabilizer additive is an ingredient that provides an increase the amount of steviol glycoside that can be solvated in a composition at a given temperature as compared to a like composition that does not contain the stabilizer additive, or that pennits steviol glycoside to remain solvated in a composition at a gi ven temperature for a longer time than a like composition that does not contain the stabilizer additive.
- a “stabilized syrup concentrate” and an “acidic stabilized syrup concentrate” are compositions comprising a stabilizer additive in an amount effective to increase the amount of steviol glycoside that can be solvated in a composition at a given temperature as compared to a like composition that does not contain the siabilizer additive, or that permits steviol glycoside to remain solvated in a composition at a given temperature for a longer time than a like composition that does not contain the stabilizer additive.
- the stabilizer additives reduce sweet linger of steviol glycosides.
- stabilizer additives such as sucrose
- a stabilizer additive selected from the group consisting of polyoxyethylene (20) DCyl ether (such as Brij®58), polyoxyethylene (100) stearyl ether (such as Brij®S-100), polyoxyethylene (40) stearate (such as POE (40), tannic acid, a sucrose monoester of nionopalmitate (such as Habo monoester P90), a sucrose monoester of palmitate/stearate having a ratio of stearate/palmitate of from 4: 1 to 1 :4 (such as Mamaa® SP50, Sisterna® SP70, and Sisterna® PS750 ), polyoxyethylenesorbitan monolaurate (such as Tween® 20), polyoxyethylenesorbitan monopalmitate (such as Tween® 40), polyoxyethylenesorbitan monostearate (such as Tween® 60), polyoxyethylene
- hyroxypropyl methyl cellulose such as MethoeelTM E19
- deoiled lecithins such as Metarin CP and Lecigran 1000P
- gum arable and mixtures thereof to form a stabilized syrup concentrate.
- an additive is selected from the group of sucrose monoesters and hydroxypropyS methyl cellulose, such as Habo monoester P90, Methoeel El 9, Tween 80, 7LF carboxymethyl cellulose, and SP70 sucrose ester.
- the stabilizer additive is selected from the group consisting of tannic acid, a sucrose monoester of palmitate/stearate having a ratio of stearate/palmitate of from 4: 1 to 1 :4, polyoxyethylene (20) cetyl ether, and mixtures thereof.
- a stabilizer additive including a particular weight ratio of sucrose monoester to meihyl cellulose proved particularly beneficial for allowing rebaudioside B to remain in solution.
- ratio when used in reference to the stabilizer additive refers to the weight ratio.
- Weight ratio refers to the ratio of two components in a composition on a weight basis. The concentration of other ingredients in the composition are not used, and do not affect, the weight ratio calculation. For example, if 10 grams of component A and 20 grams of component B are used in a composition, the weight ratio of components A to B is 0.5.
- the stabilizer additive comprises sucrose monoester and methyl cellulose at a weight ratio of from about 1 : 1 to about 5: 1 sucrose monoester to methyl cellulose. In another embodiment, the stabilizer additive comprises sucrose monoester and methyl cellulose at a weight ratio of from about 2: 1 to about 4: 1 sucrose monoester to methyl cellulose. In yet another embodiment, the stabilizer additive comprises sucrose monoester and methyl cellulose at a weight ratio of about 3: 1 sucrose monoester to methyl cellulose. In some of these embodiments, the sucrose monoester is sucrose monoester of monopalmitate and the methyl cellulose is hydroxypropyl methyl cellulose.
- the ratio of rebaudioside B present in the stabilized syrup concentrate to stabilizer additive present in the stabilized syrup concentrate of step b) is from about 1 :0.1 to about 1 : 1 by weight. In an embodiment, the ratio of rebaudioside B to stabilizer additive in step b) is from about 1 :0.3 to about :0.8 by weight.
- the ratio of steviol glycosides present in the stabilized syrup concentrate to stabilizer additive present in the stabilized syrap concentrate of step b) is from about 1 :0.1 to about 1 : 1 by weight. In an embodiment, the ratio of steviol glycosides to stabilizer additive in step b) is from about 1 :0.3 to about 1 :0.8 by weight.
- the stabilizer additive is added by first preparing a stabilizer additive stock solution comprising from about 0.5% to about 50% by weight of the stabilizer additive in water, and mixing the stabilizer additive stock solution with the syrup concentrate in an amount effective to achieve a desired steviol glycoside to stabilizer additive weight ratio in the stabilized syrup concentrate.
- This mixing is, in an embodiment, carried out under thorough mixing conditions at from about 15°C to about 35°C. In an embodiment, the mixing is carried out by a vortex mixer or a homogenizer.
- step c) the pH of the syrap concentrate is lowered to a pH of 2-5 to form an acidic stabilized syrup concentrate.
- the pH of the stabilized syrap concentrate is lowered to a pH of 2-4 to form an acidic stabilized syrup concentrate.
- the pH of the stabilized syrap concentrate is lowered to a pH of 2-3 to form an acidic stabilized syrap concentrate.
- the H of the stabilized syrup concentrate is lowered in step c) by addition of a buffer solution.
- buffer solution comprises an acid selected from the group consisting of citric acid, malic acid, lactic acid, phosphoric acid, tartaric acid, and mixtures thereof.
- buffer solution comprises sodium citrate and sodium benzoate.
- the mixing in step c) is carried out under thorough mixing conditions.
- steps a), b) and c) are independently carried out at a temperature of from about 15°C to about 45°C.
- the present method may further comprise a step d) of removing undissolved solids from the acidic stabilized syrup concentrate.
- the removal of undissolved solids comprises the steps of centrifugation and filtration.
- the removal of undissolved solids comprises the step of decanting a supernatant with subsequent filtration.
- the acidic stabilized syrup concentrate is stored without mixing for a period of time of about 4 to 60 hours, or from about 10 to 50 hours, or from about 18 to 40 hours prior to centrifugation or decanting and/or after centrifugation or decanting and prior to filtration. In an embodiment, this storage is carried out at a temperature of from about 0°C to about 45°C or from about 3°C to about ! 5°C.
- the step of centrifugation of the acidic stabilized syrup concentrate is earned out at a centrifuge rate of from about 1000 to about 40,000 rpm, or at a centrifuge rate of from about 5000 to about 30,000 rpm, or at a centrifuge rate of from about 8000 to about 15,000 rpm. In an embodiment, the step of
- centrifugation of the acidic stabilized syrup concentrate is carried out at any of the above rates for a time of from about 1 minute to about 20 minutes, or for a time of from about 2 minute to about 10 minutes, or for a time of from about 3 minute to about 8 minutes.
- the undissolved solids are filtered using a filter having a pore size of less than or equal to about 1 micron. In an embodiment, the undissolved solids are filtered using a filter having a pore size of from about 0.8 to about 0.1 microns. In an embodiment, the undissolved solids are filtered using a filter having a pore size of from about 0.7 to about 0.22 microns. In an embodiment, the undissolved solids are filtered using a filter having a pore size of from about 0.55 to about 0.35 microns.
- the acidic stabilized syrup concentrate is substantially free of undissolved solids that will not pass through a filter having a pore size of 1 micron. In an embodiment, the acidic stabilized syrup concentrate is substantially free of undissolved solids that will not pass through a filter having a pore size of 0.8 micron, or alternatively of 0.7 micron, or alternatively of 0.45 micron, or alternatively of 0.3 micron, or alternatively of 0.22 micron. In an embodiment, step d) is carried out at a temperature of from about 15°C to about 45°C.
- the acidic stabilized syrup concentrate may comprise additional ingredients, such as flavorants, preservatives, emulsifiers, colorants, nutritive sweeteners, high intensity sweeteners, vitamins, mineral salts, and clouding agents.
- the flavorant is selected from the group consisting of lemon, lime, orange, grape, lemon-lime, cola, root beer, peach, kiwi, ami mixtures thereof.
- the optional additional ingredients may be added at any stage in the process of preparation of the acidic stabilized syrup concentrate.
- the optional additional ingredients are added after step d) of removing undissolved solids from the acidic stabilized syrup concentrate.
- beverage compositions that include the sweetener compositions of the present disclosure.
- beverages include carbonated soft drinks, ready to drink teas, sports drinks, dairy drinks, yogurt-containing drinks, alcoholic beverages, energy drinks, flavored waters, vitamin drinks, fruit drinks, and fruit juices.
- a series of syrup solutions were prepared (on a w/w basis) targeting 0,26% steviol glycosides (including approximately 800 ppm rebaudioside B) in 0.05 M citrate buffer at pH 3.2.
- the solutions also contained 17.7% sucrose, 0,085% sodium benzoate, and 1% flavor (lemon lime flavor from Kerry group. New Jersey).
- sucrose monoester of monopalmitate Habo monoester P90
- hydroxypropyl methyl cellulose (MethoceiTM E19 from DOW Chemical, Michi gan) were added as listed in Table 1 below.
- solution 1 includes a 3 : 1 weight ratio of sucrose monoester of monopalmitate to hydroxypropyl methyl cellulose, while solution 4 includes a 1 : 1 weight ratio.
- Other solutions include alternative weight ratios.
- the solutions were then stored at 6°C for four days. Precipitate formation is noted in Table 3 over time. On the fourth day a sample of supernatant was filtered through a 0,45 ⁇ filter and analyzed by liquid chromatography. Table 1: Additive addition to syrap samples.
- Solution 1 had the greatest stability with no precipitate observed over 4 days and also had the greatest amount of steviol glycosides remaining in solution.
- the combinations of sucrose monoester of monopalmitate and hydroxypropyl methylcellulose gum had the greatest stability vs. control or solutions with only one additive. More specifically, the 3:1 weight ratio of sucrose monoester of
- test solutions containing increasing amounts of rebaudioside B were prepared. Each test solution contained a 3 : 1 combination of sucrose monoester of monopalmitate and hydroxypropyl methylcellulose, respectively. Control samples were also prepared without sucrose monoester of monopalmitate and hydroxypropyl methylcellulose.
- the targeted amounts of rebaudioside B were 350 ppm, 425 ppm, and 500 ppm (w/w) in a 0.05M citric acid buffer at pH 3.1 in solution 1, 2, and 3, respectively.
- the test solutions all contained 180 ppm sucrose monoester of
- test solutions containing sucrose monoester of monopalmitate and hydroxypropyl methylcellulose gum had higher rebaudioside B concentrations remaining in solution than the controls after 3 days of storage.
- the test solutions contained a 3: 1 ratio of sucrose monoester of monopalmitate and hydroxypropyl methylcellulose.
- Solution 1 contained about a weight ratio of 3:1 of sucrose monoesier of monopalmitate to hydroxypropyl methyl cellulose.
- a series of lemon-lime flavored sodas were prepared for sensory evaluation. These solutions contained (on a w/w basis) 3.12% sucrose, 0.26% steviol glycosides, 0.015% sodium benzoate, 0.018% flavor, and 0.01M citric acid at pH 3.2. In addition, these solutions contained varying amounts of sucrose monoesier of monopalmitate (Habo monoester P90) and hydroxypropyl methyl cellulose gum (Methocel El 9) to determine the impact of sensory perception of sweet linger. The concentrations are listed in Table 8. The solutions were evaluated by 3 panelists and the summary of the sensory observations is listed in Table 9.
- Table 9 Summary of the sensory observations of the soda solutions containing Habo monoester P90 and Methocel El .
- sucrose monoester of monopalmitate As the concentration of sucrose monoester of monopalmitate increased the sweet linger of the steviol glycosides decreased. As shown, a ratio of 1 : 1 resulted in a slight sweet linger and a ratio of 3 : 1 resulted in no sweet linger. The ratio of 2: 1 sucrose monoester of monopalmiiaie to hydroxypropyl methylcellulose was preferred, which resulted in a very slight sweet linger.
- a series of syrup solutions were prepared (on a w/w basis) targeting 0.22% steviol glycosides (including approximately 750 ppm reb B) in 0.05M acidic citrate buffer at pH 3.2.
- the solutions also contained 20.4% sucrose, 0.085% sodium benzoate, and 1% flavor (lemon lime flavor from Kerry group, New Jersey).
- sucrose monoester of monopalmitate Habo monoester P90 from Compass Foods, Singapore
- Table 1 1 Solut ton stability observation over four da ys.
- the solutions containing additives were able to remain soluble through 4 days of storage.
- a ratio of 1 : 1 to 2: 1 of sucrose monoester of monopalmitate to hydroxypropyl methylceilulose is preferred.
- a stock solution (on a w/w basis) of 3% mixed steviol glycoside and 0.9% sodium benzoate solution was prepared.
- the pH of the stock solution is adjusted to pH 7.5 with sodium hydroxide to fully dissolve all the steviol glycosides.
- a I M citric acid buffer at pH 2 was also prepared.
- a Shiseido Capcell PAK CI 8 column, type MGII, (5 um, 4.6 x 250 mm) is used for steviol glycoside analysis using a gradient as described in Table 2. The column is maintained at 55°C.
- emulsifiers or tannic acid increased the solubility of steviol glycosides in acidic solution.
- the main increase is in the solubility of rebaudioside B, which has a very low solubility at pH 2.5.
- the additives increased the solubility of rebaudioside B 2-3 fold.
- the best additives in this study are tannic acid and Brij 58 (polyoxyeihylene (20) cetyl ether), followed by Tween 20.
- Table 13 Steviol glycoside concentration in supernatant after storage at 4°C for 20 hours.
- Tween 80 polyoxyethylenesorbitan
- RA rebaudioside A
- stv stevioside
- Example 6 The experiment is conducted according to the procedure set out in Example 6, except for the mixed steviol glycoside stock solution, which also contains
- rebaudioside D rebaudioside D.
- Each experiment contains the following components: 0.15 ml of 3% stock steviol glycoside solution, 0.1 ml of 1 % additive or emulsifiers listed in Table 14, 0.75 mi of deionized water.
- the solution was mixed for 5 seconds by vortex before being acidified with the addition of 0.05 ml of 1 M citric acid buffer, pH 2.
- the solution was mixed again for 5 seconds and stored at 4°C for 20 hours before analysis by HPLC.
- Table 14 shows that all treatments with additives increased the solubility of rebaudioside D and rebaudioside A and rebaudioside B, compared to the control, but the impact on rebaudioside B was the greatest.
- the most effective additives for rebaudioside B as shown in this table arequela PS750,quela SP70, Brij 58, and tannic acid.
- quela PS750 is a 75% monoester of palniitate/stearate.
- quela SP70 is a 70% monoester of stearate/palmitate.
- a 0.3% solution of mixed steviol glycoside was prepared according to the procedure set out in Example 6 and mixed with 0.1% of Brij 58, PS750, or tannic acid at pH 2.5 with 0,05 M citric acid buffer. The solution was mixed continuously in a rotating mixer for 20 hours at room temperature. After 20 hours, the solution was maintained at 4°C for another 24 hours without mixing. The concentration of steviol glycosides in solution was determined by separating the supernatant from precipitate by filtration through a 0.45 micron filter and diluting the supernatant 1 :6 with
- a 0.3% solution of mixed steviol glycoside was prepared according to the procedure set out in Example 6. 0.01%, 0.05% or 0.1% of tannic acid was mixed with the mixed steviol glycoside solution at pH 2.5, After mixing, the vials were stored at 4°C for 8 hours before analysis. The concentration of steviol glycosides in the supernatant was measured by HPLC after filtering away precipitates in the solution and diluting 1 :6 with deionized water. The level of increase in each glycoside is shown in Table 6 below. There is a dose response between tannic acid concentration in the solution and the amount of soluble rebaudioside B. The effect on rebaudioside A and rebaudioside D is minimal.
- a solution of each stabilization additive was prepared (on a w/w basis) targeting final concentrations listed below in 8.5ml. 0.3g of dry glycoside mixture was then added to the solution targeting 0.3%) final concentration. 1 ml of 1% potassium benzoate was added to each solution at a targeted final concentration of 0.1% (w/w). The solutions were mixed thoroughly to ensure full dissolution. 0.5ml of 1M citric acid solution, pH adjusted to 2.5, was added to each solution to make a final
- the terms "about” or “approximately” mean within an acceptable range for the particular parameter specified as determined by one of ordinary skill in the art, which will depend in part on how the value is measured or determined, e.g., the limitations of the sample preparation and measurement system. Examples of such limitations include preparing the sample in a wet versus a diy environment, different instruments, variations in sample height, and differing requirements in signal-to-noise ratios. For example, “about” can mean greater or lesser than the value or range of values stated by 1/10 of the stated values, but is not intended to limit any value or range of values to only this broader definition. For instance, a concentration value of about 30% means a concentration between 27% and 33%. Each value or range of values preceded by the term “about” is also intended to encompass the embodiment of the stated absolute value or range of values.
- the term can mean within an order of magnitude, preferably within 5-fold, and more preferably within 2-fold, of a value.
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Abstract
Description
Claims
Priority Applications (8)
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JP2016540041A JP2017500863A (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycosides in concentrated syrup |
MX2016007813A MX2016007813A (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup. |
CN201480072663.2A CN105899088A (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup |
US15/104,605 US20160309761A1 (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup |
EP14872462.8A EP3082461A4 (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup |
CA2933024A CA2933024A1 (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup |
AU2014366958A AU2014366958A1 (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup |
AU2018247334A AU2018247334A1 (en) | 2013-12-16 | 2018-10-12 | Stabilized steviol glycoside in concentrated syrup |
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US201361916488P | 2013-12-16 | 2013-12-16 | |
US61/916,488 | 2013-12-16 |
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PCT/US2014/068552 WO2015094688A1 (en) | 2013-12-16 | 2014-12-04 | Stabilized steviol glycoside in concentrated syrup |
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US (1) | US20160309761A1 (en) |
EP (1) | EP3082461A4 (en) |
JP (1) | JP2017500863A (en) |
CN (1) | CN105899088A (en) |
AU (2) | AU2014366958A1 (en) |
CA (1) | CA2933024A1 (en) |
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US12016357B2 (en) | 2015-05-20 | 2024-06-25 | Cargill, Incorporated | Glycoside compositions |
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BR112019017614A2 (en) * | 2017-02-27 | 2020-03-24 | Pepsico, Inc. | COMPOSITIONS AND METHODS TO ENHANCE SWEETNESS |
CA3071805C (en) * | 2017-09-01 | 2024-06-18 | Fuji Oil Holdings Inc. | Oil and fat composition containing unsaturated fatty acid |
BR112020006822B1 (en) * | 2017-10-06 | 2023-03-07 | Cargill, Incorporated | METHOD FOR MAKING A COMPOSITION OF YERBA MATE EXTRACT |
JP2022527518A (en) | 2019-04-06 | 2022-06-02 | カーギル インコーポレイテッド | Sensory modifier |
GB2593412A (en) * | 2019-06-19 | 2021-09-29 | Tate & Lyle Ingredients Americas Llc | Liquid concentrate composition |
CN110150624A (en) * | 2019-06-24 | 2019-08-23 | 江苏科乐欣生物有限公司 | A kind of compound concentration Sugarless syrups and its production method containing steviol glycoside |
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- 2014-12-04 CA CA2933024A patent/CA2933024A1/en not_active Abandoned
- 2014-12-04 US US15/104,605 patent/US20160309761A1/en not_active Abandoned
- 2014-12-04 JP JP2016540041A patent/JP2017500863A/en active Pending
- 2014-12-04 MX MX2016007813A patent/MX2016007813A/en unknown
- 2014-12-04 AU AU2014366958A patent/AU2014366958A1/en not_active Abandoned
- 2014-12-04 EP EP14872462.8A patent/EP3082461A4/en not_active Withdrawn
- 2014-12-04 CN CN201480072663.2A patent/CN105899088A/en active Pending
- 2014-12-04 WO PCT/US2014/068552 patent/WO2015094688A1/en active Application Filing
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2018
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AU2014366958A1 (en) | 2016-06-30 |
AU2018247334A1 (en) | 2018-11-08 |
MX2016007813A (en) | 2016-11-28 |
US20160309761A1 (en) | 2016-10-27 |
JP2017500863A (en) | 2017-01-12 |
EP3082461A4 (en) | 2017-06-28 |
EP3082461A1 (en) | 2016-10-26 |
CN105899088A (en) | 2016-08-24 |
CA2933024A1 (en) | 2015-06-25 |
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