NZ755861A - Sweetening compositions - Google Patents
Sweetening compositionsInfo
- Publication number
- NZ755861A NZ755861A NZ755861A NZ75586117A NZ755861A NZ 755861 A NZ755861 A NZ 755861A NZ 755861 A NZ755861 A NZ 755861A NZ 75586117 A NZ75586117 A NZ 75586117A NZ 755861 A NZ755861 A NZ 755861A
- Authority
- NZ
- New Zealand
- Prior art keywords
- range
- present
- sweetening
- tannic acid
- amount
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 134
- YWPVROCHNBYFTP-OSHKXICASA-N Rubusoside 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]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 YWPVROCHNBYFTP-OSHKXICASA-N 0.000 claims abstract description 50
- 229920001864 tannin Polymers 0.000 claims abstract description 27
- 235000018553 tannin Nutrition 0.000 claims abstract description 27
- 239000001648 tannin Substances 0.000 claims abstract description 27
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 claims abstract description 19
- 239000000284 extract Substances 0.000 claims abstract description 17
- LRBQNJMCXXYXIU-NRMVVENXSA-N Tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 60
- 239000001263 FEMA 3042 Substances 0.000 claims description 35
- 229940033123 Tannic Acid Drugs 0.000 claims description 35
- 229920002258 tannic acid Polymers 0.000 claims description 35
- 235000015523 tannic acid Nutrition 0.000 claims description 35
- 235000019202 steviosides Nutrition 0.000 claims description 34
- 239000004383 Steviol glycoside Substances 0.000 claims description 29
- 235000019411 steviol glycoside Nutrition 0.000 claims description 29
- 150000008144 steviol glycosides Chemical class 0.000 claims description 29
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 claims description 17
- 239000005720 sucrose Substances 0.000 claims description 17
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-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 16
- AIONOLUJZLIMTK-AWEZNQCLSA-N Hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 claims description 16
- VGEREEWJJVICBM-UHFFFAOYSA-N Phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 claims description 16
- 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 claims description 16
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 claims description 8
- 229960001587 hesperetin Drugs 0.000 claims description 8
- 235000010209 hesperetin Nutrition 0.000 claims description 8
- 229940032084 steviol Drugs 0.000 claims description 8
- GSTCPEBQYSOEHV-QNDFHXLGSA-N 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C=C1O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 GSTCPEBQYSOEHV-QNDFHXLGSA-N 0.000 claims description 7
- 239000001689 FEMA 4674 Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 3
- 235000013361 beverage Nutrition 0.000 abstract description 34
- ARGKVCXINMKCAZ-UZRWAPQLSA-N Neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 abstract description 13
- ARGKVCXINMKCAZ-NRRCNVALSA-N Neohesperidin Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1Oc1cc(O)c2C(=O)C[C@@H](c3cc(O)c(OC)cc3)Oc2c1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](C)O1 ARGKVCXINMKCAZ-NRRCNVALSA-N 0.000 abstract description 13
- BAQAVOSOZGMPRM-JVFSCRHWSA-N (2R,3R,4R,5R,6R)-2-[(2S,3R,4R,5R)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-5-chloro-6-(hydroxymethyl)oxane-3,4-diol Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@]1(CCl)[C@H](O)[C@@H](O)[C@H](CCl)O1 BAQAVOSOZGMPRM-JVFSCRHWSA-N 0.000 abstract description 9
- 239000004376 Sucralose Substances 0.000 abstract description 9
- 235000019408 sucralose Nutrition 0.000 abstract description 9
- WBZFUFAFFUEMEI-UHFFFAOYSA-N Acesulfame potassium Chemical compound [K+].CC1=CC(=O)NS(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-N 0.000 abstract description 7
- 235000016976 Quercus macrolepis Nutrition 0.000 abstract description 7
- 244000305267 Quercus macrolepis Species 0.000 abstract description 7
- CVHZOJJKTDOEJC-UHFFFAOYSA-N Saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 abstract description 7
- IAOZJIPTCAWIRG-QWRGUYRKSA-N Aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 abstract description 6
- 229960003438 Aspartame Drugs 0.000 abstract description 6
- 108010011485 Aspartame Proteins 0.000 abstract description 6
- 229940081974 Saccharin Drugs 0.000 abstract description 6
- 239000000605 aspartame Substances 0.000 abstract description 6
- 235000010357 aspartame Nutrition 0.000 abstract description 6
- 235000019204 saccharin Nutrition 0.000 abstract description 6
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 abstract description 6
- 229940109275 Cyclamate Drugs 0.000 abstract description 4
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Sodium cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 abstract description 4
- 229940109529 Pomegranate Extract Drugs 0.000 abstract description 3
- 241000544066 Stevia Species 0.000 abstract 5
- 239000000306 component Substances 0.000 description 43
- 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 25
- 240000001132 Stevia rebaudiana Species 0.000 description 19
- 235000000346 sugar Nutrition 0.000 description 18
- 235000014633 carbohydrates Nutrition 0.000 description 17
- 206010013911 Dysgeusia Diseases 0.000 description 15
- 235000003599 food sweetener Nutrition 0.000 description 15
- 235000014214 soft drink Nutrition 0.000 description 15
- 239000003765 sweetening agent Substances 0.000 description 15
- 230000035807 sensation Effects 0.000 description 12
- 235000019615 sensations Nutrition 0.000 description 12
- DRSKVOAJKLUMCL-UHFFFAOYSA-N Rebaudioside B Chemical compound C1CC2C3(C)CCCC(C)(C(O)=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 DRSKVOAJKLUMCL-UHFFFAOYSA-N 0.000 description 11
- LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 10
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
- CANAPGLEBDTCAF-MORBOXIVSA-N Dulcoside 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](C)O6)[C@@H](O)[C@H](O)[C@H](CO)O5)(C4)CC3)CC2)CCC1 CANAPGLEBDTCAF-MORBOXIVSA-N 0.000 description 8
- 239000001512 FEMA 4601 Substances 0.000 description 8
- 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 8
- HELXLJCILKEWJH-NCGAPWICSA-N Stevioside A3 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 8
- 239000003623 enhancer Substances 0.000 description 8
- 230000002708 enhancing Effects 0.000 description 8
- 235000001727 glucose Nutrition 0.000 description 8
- 235000019203 rebaudioside A Nutrition 0.000 description 8
- 235000015897 energy drink Nutrition 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 150000008163 sugars Chemical class 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 6
- QSRAJVGDWKFOGU-WBXIDTKBSA-N Rebaudioside C Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 description 6
- UEDUENGHJMELGK-VESORUSYSA-N Stevioside 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](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 UEDUENGHJMELGK-VESORUSYSA-N 0.000 description 6
- 239000008122 artificial sweetener Substances 0.000 description 6
- 235000021311 artificial sweeteners Nutrition 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 6
- -1 neotarne Chemical compound 0.000 description 6
- RMLYXMMBIZLGAQ-HZMBPMFUSA-N (2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid Chemical compound C1=CC=C2C(C[C@](O)(C[C@H](N)C(O)=O)C(O)=O)=CNC2=C1 RMLYXMMBIZLGAQ-HZMBPMFUSA-N 0.000 description 5
- 235000019658 bitter taste Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 230000001603 reducing Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229940077731 Carbohydrate nutrients Drugs 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 229940074391 Gallic acid Drugs 0.000 description 4
- 235000014360 Punica granatum Nutrition 0.000 description 4
- 240000006764 Punica granatum Species 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 4
- SRBFZHDQGSBBOR-SQOUGZDYSA-N Xylose Natural products O[C@@H]1CO[C@@H](O)[C@@H](O)[C@@H]1O SRBFZHDQGSBBOR-SQOUGZDYSA-N 0.000 description 4
- 235000014171 carbonated beverage Nutrition 0.000 description 4
- 235000004515 gallic acid Nutrition 0.000 description 4
- 235000021096 natural sweeteners Nutrition 0.000 description 4
- 229940013618 stevioside Drugs 0.000 description 4
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 3
- 239000001776 FEMA 4720 Substances 0.000 description 3
- 239000005715 Fructose Substances 0.000 description 3
- 240000004670 Glycyrrhiza echinata Species 0.000 description 3
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 3
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 3
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 3
- 241000282619 Hylobates lar Species 0.000 description 3
- 229940010454 Licorice Drugs 0.000 description 3
- 241001092459 Rubus Species 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920001461 hydrolysable tannin Polymers 0.000 description 3
- 235000014063 licorice root Nutrition 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- GHBNZZJYBXQAHG-KUVSNLSMSA-N (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(3S,8S,9R,10R,11R,13R,14S,17R)-17-[(2R,5R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H](CC[C@@H](C)[C@@H]1[C@]2(C[C@@H](O)[C@@]3(C)[C@H]4C(C([C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]6[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O6)O)O5)O)CC4)(C)C)=CC[C@H]3[C@]2(C)CC1)C)C(C)(C)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GHBNZZJYBXQAHG-KUVSNLSMSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 240000002268 Citrus limon Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- MFTSECOLKFLUSD-UHFFFAOYSA-N Hexahydroxydiphenic acid Chemical group OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C(O)C=C1C(O)=O MFTSECOLKFLUSD-UHFFFAOYSA-N 0.000 description 2
- CDAISMWEOUEBRE-GPIVLXJGSA-N Inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 2
- 229960000367 Inositol Drugs 0.000 description 2
- GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 235000009421 Myristica fragrans Nutrition 0.000 description 2
- RLLCWNUIHGPAJY-RYBZXKSASA-N Rebaudioside E Natural products O=C(O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)[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](O)[C@H](CO)O5)(C4)CC3)CC2)CCC1 RLLCWNUIHGPAJY-RYBZXKSASA-N 0.000 description 2
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- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- LKDRXBCSQODPBY-DPYQTVNSSA-N β-D-tagatopyranose Chemical compound OC[C@@]1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-DPYQTVNSSA-N 0.000 description 1
Abstract
The invention relates to a sweetening composition comprising a natural sweet-tasting carbohydrate, a stevia compound, rubusoside, and tannin, wherein component d) is present in an amount in the range from 1 mg/l to 400 mg/l. The invention also relates to a sweetening composition comprising a natural sweet-tasting carbohydrate, a stevia compound, rubusoside, tannin and oak extract or pomegranate extract. The invention further relates to a sweetening composition comprising acesulfam or aspartame, sucralose, a stevia compound, saccharin or cyclamate, neohesperidin, and tannin in an amount in the range from 1 mg/l to 400 mg/l. Moreover, the invention relates to a sweetening composition comprising a) 0,1 to 50 g/l of a natural sweet-tasting carbohydrate, b) 40 to 120 g/l of a natural sweet-tasting carbohydrate different from a), and c) 30 to 300 mg/l of rubusoside. And, the invention is about the use of said sweetening compositions for sweetening and preparing beverages. sweet-tasting carbohydrate, a stevia compound, rubusoside, tannin and oak extract or pomegranate extract. The invention further relates to a sweetening composition comprising acesulfam or aspartame, sucralose, a stevia compound, saccharin or cyclamate, neohesperidin, and tannin in an amount in the range from 1 mg/l to 400 mg/l. Moreover, the invention relates to a sweetening composition comprising a) 0,1 to 50 g/l of a natural sweet-tasting carbohydrate, b) 40 to 120 g/l of a natural sweet-tasting carbohydrate different from a), and c) 30 to 300 mg/l of rubusoside. And, the invention is about the use of said sweetening compositions for sweetening and preparing beverages.
Description
WO 2018/122383 PCT/EP2017/084826
Sweetening compositions
Description
The present invention relates to sweetening compositions, their use for the preparation of
sweetening syrups and beverages as well as to the preparation of said beverages.
Common soft drinks usually contain significant amounts of natural sugars such as sucrose,
glucose, fructose or mixtures thereof. The caloric content of these natural sugars usually is
in the range from 3.6 to 3.9 keal/g. Many attempts have been made to reduce the caloric
content of beverages such as soft drinks. In some instances natural sugars have been re»
placed by steviol glycosides. Some steviol glycosides have a sweetening power which is
about 240 to 400 times that of natural sugar sucrose. Steviol glycosides are derived from
extracts of the leaves of the stevia plant (Stevie rebaudicma Ber-tom"). The four major steviol
glyeosides found in the leaves of the stevia plant are stevioside (about 5 to 10 wt-%), rebau—
(iioside A (about 2 to 4 wt—%), rebaudioside CL (about 1 to 2 wt-»%} and duleoside A (about
0.5 to 1 wt—%). Further steviol glycosides which are found in the extract of the leaves of the
stevia plant, however in rather minute quantities, are rebaudioside B, rebaudioside D and
rebaudioside E. Tlie common aglycon of all steviol glyeosides is steviol which belongs to the
class of cliterpenes.
Unfortunately, beverages sweetened with steviol glyeosides suffer some drawbacks which
for many consumers outway the calorie content of conventional beverages. Steviol glyco-
sides are known to cause a bitter and/or licoriee—lil<e aftertaste, in some instances also a
metallic aftertaste. In addition, the sweet sensation is retarded to some extent, that is, the
sweetening exhibit a so—called lingering. In some cases steviol glycosides are also responsi-
ble for a blunt or dry mouthfeel.
In El’ 2 519 118 sweetening compositions are disclosed containing a sweetener and at least
one sweetness enhancer chosen from terpenes, flavonoids, amino acids, proteins, polyols,
other known natural sweeteners, seeowianrmarane glycosides, and analogues thereof. Snit-
WO 2018/122383 PCT/EP2017/084826
able sweetening enhancer are reported to include stevia sweeteners, such as stevioside, ste-
violbioside, rebaudioside A, rebaudioside B, rebauclioside C, rebandioside D, rebauclioside
F, ancl dulcoside A. The at: least one sweetness enhancer has to be present in the composite
tion in an amount at or below the sweetness detection threshold level of the at least one
sweetness enhancer, and the at least one sweetener and the at least one sweetness enhancer
are different.
In E? 2 386 211 the use of rubusoside for masking, reducing or suppressing a bitter, sour
and/or astringent taste impression of a bitter, sour and/or astringent-tasting substance is
described. Compositions containing rubusoside shall mask, reduce or suppress in food
products and in pharrnaceuticals the bitter, sour and/or astringent taste impression of
compouncls such as steviosides and reljaudioside A.
And, W0 2008/049256 addresses a sweetened consumable comprising a) at least 0.0001
% of at least one sweetener, wherein said sweetener includes sucrose, fructose, glucose,
high fructose corn syrup, corn syrup, xylose, arabinose, rhamnose, eryfliritol, xylitol, man-
nitol, sorbitol, inositol, acesulfame potassium, aspartame, neotarne, sucralose, saccharine,
or combinations thereof, wherein said at least one sweetener or sweetener combination is
present in a concentration above the sweetness ‘detection threshold in a concentration of at
least isosweet to 2% sucrose, and b) at least one sweetness enhancer selected from the
group consisting of naringin dihydrochalcone, mogroside V, swingle extract, rubusoside,
rubus extract, stevioside, and rebauclioside A. Each sweetness enhancer shall be present in
a concentration near its sweetness detection thresholzi. For naringin dihyclrochalcone this
concentration shall be from .2 to 60 ppm, for rubusoside from 1.4 ppm to 56 ppm, for rubus
extract from 2 ppm to 80 ppm, for mogroside V from 0.4 ppm to 12.5 ppm, for swingle ex—
tract from 2 to no ppm, for steviosicle from 2 to 60 ppm, and for rebandioside A from 1 to
DPT“-
Also many other attempts have been made to overcozrne the afore-mentioned shortcomings
of steviol glycoside sweeteners such as a bitter and/ or licorice-like aftertaste, a blunt or dry
mouthfeel and/or a sweet aftertaste.
For example, according to W0 2012/073121 A2 the bitter aftertaste of steviol glycosides
shall be decreased or eliminated by the reduction or elimination of rebaudioside C or
dulcoside A or both from stevia compositions. However, it has been found that the reduc-
tion of rebaudioside C and/or dulcoside A as such does not guarantee a reduction in bitter
aftertaste. Moreover, even with stevia compositions being void of rebaudioside C or
WO 2018/122383 PCT/EP2017/084826
dulcoside A consumers experience a slow onset and sometimes even a longer duration of
the sweetness sensation.
In W0 2008/147726 it is described that a more suganlilte flavor profile shall be obtained
by sweetener compositions comprising at least a) one sweetness enhancer such as urea or
thiourea, b) at least one sweetener comprising a carbohydrate sweetener, a natural high-
potency sweetener, a synthetic high-potency sweetener or a combination thereof such as
rebaudioside compounds, sucralose, aspartame or acesulfarne potassium, and c) at least
one sweet taste improving composition selected from the group consisting of carbohy-
drates, polyols, amino acids, or mixtures thereof.
New sweetened beverage formulations which do not exhibit a bitter aftertaste shall be ob-
tained according to El’ 2 474 240 A1 by use of rebaudioside D and an acidulant comprising
at least lactic acid and one or both of tartaric acid and citric acid, and no phosphoric acid.
From W0 2011/146463 A2 it can be derived that the bitterness in an otherwise sweet com-
position containing steviol glycosides shall be masked by incorporating an increased
amount, relative to naturally occurring compositions, of rebaudioside D.
EP 2 486 806 A1 discloses a low-calorie orange juice drink which makes use of a mixture of
84. wt—% rebaudioside A and 16 wt—% rehaudioside D. Ditierent from a low»-calorie orange
juice having been sweetened with a conventional stevia extract a pleasant taste similar to
sucrose, a full mouthfeel, and no bitterness and no aftertaste shall be observed during sen—
sory evaluation. A similar outcome was reported for a zero-calorie carbonated beverage.
According to WC) 2008/ 112967 A1 the metallic aftertaste experienced with beverages con-
taining conventional steviol glycosides shall be masked by the presence of anisic acid.
And, in WC 2012/109585 A1 it is disclosed that attributes such as bitterness, sweet after-
taste and licorice flavor of steviol glycosides may be overcome by sweetening compositions
comprising a blend of rebandioside A, rebaudioside B and steviol glycosides, in particular
when the ratio of rebaudioside B to total steviol glycosides in the blend ranges from 0.5 %
to about 50 % and more preferably from about 5 % to about 40 %.
Sucrose being the standard natural sweetener has a characteristic time and intensity sweet-
ness profile. Whereas some artificial sweeteners have a more rapid onset of sweetness than
sucrose, most artificial sweeteners such as stevia compounds have not only a significantly
slower onset but ai/so exhibit a significantly longer linger than sucrose. The afore~
WO 2018/122383 PCT/EP2017/084826
mentioned drawbacks associated with the use of steviol glycosides are still not overcome to
a satisfactory extent. It is therefore desirable to obtain beverages, which contain less or no
natural sweeteners, and which have a much improved sweetness and aroma profile.
Accordingiy, there still is a need to provide low-calorie beverages which do not exhibit a
delayed onset of the sensation of sweetness and which, optionally, also do not suffer from a
bitter or licorice-like aftertaste and / or which do not cause a blunt or dry xnouthfeel. Hence,
it has been a major goal of the present invention to attain a temporal sweetening profil sirn~
ilar or even essentially identicai to that of natural sugar, Le. a natural sweetening profile, in
particular with respect to both the onset of sweetness and its lingering time.
The problem underlying the present invention has surprisingly been solved by a sweetening
composition according to a first embodiment comprising a) at least one natural sweet-
tasting carbohydrate, in) at least one stevia compound, c) rubusoside and/or at least one
rubusoside derivative and/or neohesperidin and/or thaumatine and/or phloretin and/or
trilobatin and/or monatin and/or hesperetin and/or at least one enzyme—1:reated steviol
glycoside, in particular rubusoside or at least one rubusoside derivative or neohesperidin or
at least one enzyme~treated steviol glycoside or any combination thereof, and d) at least one
tannin, in particular tannic acid and/ or at least one tannic acid derivative or a composition
or extract containing tannic acid and/or at least one tannic acid derivative in an amount,
based on the at least one tannin, in particular tannic acid and the at least one tannic acid
derivative.
With said first embodirnentthe at least one tannin, in particular tannic acid and/or at least
one tannic acid derivative or a composition or extract containing tannic acid and/ or at least
one tannic acid derivative, are to be present in an amount, based on the at least one tannin,
in particular tannic acid and the at least one tannic acid derivative, in the range from 1 mg/l
to 400 mg/l, preferably in the range from 10 mg/l to 300 mg/l and more preferably in the
range from 25 to 250 mg/1, if the composition of said first embodiment is an aqueous corn~
position, in particular in the ‘form of a beverage.
Alternatively or simultaneously, said first embodiment of a sweetening composition can be
characterized in that, based on the total weight of component b), component c), in particu-
lar the rubusoside and] or at least one rubusoside derivative, and component cl), in particu~
lar tannic acid and/or at least one tannic acid derivative, the component b) is present in an
amount in the range from 45 to 75 wt—%, the component c), in particular the rubusoside
and/ or at ieast one rubusoside derivative, is present in an amount in the range from 2 to 40
WO 2018/122383 PCT/EP2017/084826
wI:~%, and the component d), in particular tannic acid and/or at least one tannic acid deriv-
ative, is present in an amount in the range from 2 to 40 wt~%, wherein in each case the sum
of components h), c) and :1) always adds up to 100 wt—%. The weight ranges are in particu-
lar applicable for an alternative embodiment in which the composition of said first embod-
iment represents a dry mixture, in particular in powder and/or particulate form.
According to a preferred embodiment the aforementioned alternate forms of the first em~
bodiment of a sweetening composition, based on the total weight of component b), compo-
nent C), in particular the rubusoside and/or at least one ruhusosicle derivative, and compo-
nent d), in particular tannic acid and / or at least one tannic acid derivative, the component
b) is present in an amount in the range from 50 to 70 wt~%, in particular 55 to 65 wt-%, the
component c), in particular the ruhusoside and/or at least one rubusoside derivative, is
present in an amount in the range from 5 to 35 wt—%, in particular 10 to 30 wt-%, and the
component d), in particular tannic acid and / or at least one tannic acid derivative, is present
in an amount in the range from 5 to 35 wt~%, in particular 19 to 30 wt—%, wherein in each
case the sum of components b), c) and d) always adds up to 100 wt-%.
The at least one natural swe-et—tasting carbohydrate of the first embodiment in particular is
sucrose. And, among the at least one stevia compound of the first embodiment those are
preferred selected from the group consisting of steviol glycosides, rebaudiosides and mix-
tures thereof.
Among the compounds of component c) of the first embodiment of the sweetening compo-
sition of the present invention ruhusoside and/or at least one rubusoside derivative are
preferred, rubusoside being particularly preferred.
Tannins in the meaning of the present invention shall comprise polyphenols, in particular
so—called plant polyphenols, which exhibit an astringent sensation. It is presently believed
that said astringent sensation is caused by or associated with a binding reaction of said po-l~
yphenols to proteins. For example, tannic acid coagulates all:-umen and gelatin. Tannins
usually have two or three phenolic hydroxyl groups on the phenyl ring. Tannins can, for
example, be classified into pyrogallol type tannins and the catechol type tannins. Tannins
can also be classified into so-called. hydrolysable tannins, e.g. based on ellagic acid and gal-
lic acid, and condensed tannins, e.g. based on catechol. Tannins of the present invention
can be derived from any of the aforementioned classified groups.
WO 2018/122383 PCT/EP2017/084826
Suitable tannins encompass for example ellagitannins, such as punicalagin and geranii, and
gallotannins which belong to the class of hydrolysable tannins, as well as stilbenoicls such
as astringin or resveratrol. Ellagitannins usually contain various numbers of hexahy-
droxydiphenoyl (HHDP) units, as well as galloyl units and,’ or sanguisorboyl units bound to
sugar moiety. Suitable representatives of tannins also comprise epigallocatechin gallate,
epicatechin gallate, and phlorotannins.
Tannins can for example be obtained from extracts of oak or of pomegranates, in particular
pomegranate rind. extracts. For example, gallic acid is found in gallnuts, sumac, witch hazel,
tea leaves, oak bark,
The composition or extract containing at least one tannin, in particular tannic acid and/ or
at least one tannic acid derivative, can be derived from seeds, hark, cones, husk, and/or
heartwood of oak, pomegranate, chestnut, gallnut or mimosa, in particular from oak or
pomegranate.
Tannic acid in the meaning of the present invention in particular comprises ‘polygalloyl glu-
coses and polygalloyl qninic acid esters with the number of galloyl moieties per molecule in
particular ranging from 2 up to 12, in particular 3 to 12, eg. decagailoyl glucose. According-
ly, tannic acid in the meaning of the present invention can be understood to be, for exam-
ple, formed of gallic acid molecules and glucose. Tannic acid will usually hydrolyze into
glucose and gallic acid and/or ellagic acid units. In general, with the term tannic acid both
an individual compound as well as a mixture of two or more compounds is meant.
Enz.yme—treated steviol glycosides include those steviol glycosides having been treated with,
for example, cyclomaltodextrin glucanotransferase (CC-Ease).
The compounds of component c) of the first embodiment of the present invention, in par-
ticular rubusoside or a rubusoside derivative or neohesperidin or enzyme—treated steviol
glycosides, and even more particular rubusosicle, have been found with the compositions of
the present invention to assist in improving its sweetening profile at the onset so that the
sweetening sensation is shifted towards the actual consumption of the sweetening composi-
tion of a product containing said sweetening composition of the first emboditnent of the
present invention. Rubusoside (CAS No: 64849339-4) can be found in leaves of Rubus
suavissimus S. Lee (Chinese sweet leaf). Rubusosides in the meaning of the present inven-6
tion shall also comprise enzyinatically-treated. rubusosides.
WO 2018/122383 PCT/EP2017/084826
With the sweetening cotnpositions according to said first embodiment it is preferred that
the at least one natural sweet-tasting carbohydrate, in particular sucrose, is present in an
amount in the range from 5 to 80 g/l, preferably in the range from 15 g/l to 70 g/l and more
preferably in the range from 25 to 55 g/3. Alternatively or in addition in said sweetening
compositions of the first embodiment rubusoside and / or at least one rubusoside derivative
preferably is present in an amount in the range from 20 to 200 mg/1, more preferably in the
range from 20 mg/l to 150 mg/l and in particular in the range from 30 to 125 mg/l.
The problem underlying the present invention has also been solved by a sweetening compo-
sition, also referred to as second embodiment of a sweetening composition of the present
invention, comprising a) at least one natural ewe-et—tasting carbohydrate, in particular su-
crose, lo) at least one stevia compound, in particular selected from the group consisting of
stcviol glycosides, rebaudiosides and mixtures thereof, cl rubusoside and/’ or at least one
rubusoside derivative and/or neohesperidin and/or thaumatine and/or phloretin and/or
trilobatin and/or monatin and/or hesperetin and/or at least one enzyme~treated steviol
glycoside, in particular rubusoside or at least one rubusoside derivative or neohesperidin or
at least one enzyme-treated steviol glycoside or any combination thereof, d) tannic acid
and/ or at least one tannic acid derivative and e) oak extract and/or pomegranate extract.
Among the compounds of component c) of the second embodiment of the sweetening co1n~
position of the present invention ruhusoside and/ or at least one ruhusoside derivative are
preferred, rubusoside being particularly preferred.
In said second embodimentof the sweetening composition of the present invention the at
least one natural sweet—tasting carbohydrate, in particular sucrose, is preferably present in
an amount in the range from 5 to 80 g/l, more preferably in the range from 15 g/i to 7o g/l
and in particular in the range from 25 to 55 g/l. Alternatively or in addition in said sweete:n—
ing compositions of the second embodiment rubusoside and/or at least one rubusoside
derivative is preferably present in an amount in the range from 2o to 20:) mg/l, more pref?»
erably in the range from 20 mg/l to 150 mg/l and in particular in the range from 30 to 125
mg/l. And, again, alternatively or in addition in said second embodiment of the sweetening
composition of the present invention the total amount of tannic acid and/ or at least one
tannic acid derivative is preferably present in an amount in the range from 1 mg/l to 4oo
mag/1, more preferably in the range from 10 mg/l to 300 mg/l and in particular in the range
from 25 to 250 mg/l.
WO 2018/122383 PCT/EP2017/084826
The problem underlying the present invention has also been solved by a sweetening compo-
sition, also referred to as third embodiment of a sweetening composition of the present in-
vention, comprising a) acesulfam and/or aspartam, in particular acesulfarn, bl sucralose
and/or at least one stevia compound, in particular selected from the group consisting of
steviol glycosides, rebaudiosides and mixtures thereof, and/or saccharin and/or cyclarnate,
C) ncohesperidin and/or thaumatine and/or rubusoside and/or at least one rubusoside de-
rivative and./or phloretin and/or trilohatin and/ or monatin and/or hesperetin, cl) at least
one tannin, in particular tannic acid and/ or at least one tannic acid derivative or a composi-
tion or extract containing tannic acid and/or at least one tannic acid derivative.
Among the compounds of component c) of the third embodiment of the sweetening compo-
sition of the present invention neohesperidine and ruhusoside are preferred, neohesperi-
dine being particularly preferred.
in this third embodiment component d), based on the at least one tannin, in particular tan-
nic acid and the at icast one tannic acid derivative, is present in an amount in the range
from 1 mg/l to 400 mg/l, preferably in the range from 10 mg/l to 300 mg/l and more pref-
erably in the range from 25 to 250 mg/l.
Such a sweetening composition according to the third embodiment of the invention is par-
ticularly preferred which comprises a) acesulfam and/ or aspartame, in particular acesul-
fam, h) sucralose or saccharin or at least one ate-via compound, in particular selected from
the group consisting of steviol glycosides, rehaudiosides and mixtures thereof, c) neohe-
speridin, and d) at least one tannin, in particular tannic acid and/' or at least one tannic acid
derivative or a composition or extract containing tannic acid and/or at least one tannic acid
derivative, wherein component d), based on the at least one tannin, in particular tannic acid
and the at least one tannic acid derivative, is present in an amount in the range from 1 mg/l
to 400 mg/l, preferably in the range from to mg/l to 300 mg/l and more preferably in the
range from 25 to 250 mg/ l if the composition of said third embodiment is an aqueous com-
position, in particular in the form of a beverage.
Alternatively or simultaneously, said third embodiment of a sweetening composition can be
characterized in that, based on the total weight of component a), in particular acesulfarn,
component b), in particular sucralose, component c), in particular neohesperidine, and
component d), in particular tannic acid and/ or at least one tannic acid derivative, the com-
ponent a) is present in an amount in the range from 10 to 50 wt-%,‘the component b) is pre-
sent in an amount in the range from 15 to 65 wt—%, the component c) is present in an
WO 2018/122383 PCT/EP2017/084826
amount in the range from 0,1 to 4 wt-%, and the component :1) is present in an amount in
the range from 5 to 50 wt—%, wherein in each case the sum of components a, b), c) and cl)
always adds up to 100 Wt—%.
According to a preferred embodiment the aforementioned alternate forms of the third em—
bodiment of a sweetening composition, baserl on the total weight of component a), in par
ticular acesnlfam, component b), in particular sucralose, component c), in particular nee»
hesperidine, and component d), in particular tannic acid and/or at least one tannic acid
derivative, the component at) is present in an amount in the range from 15 to 45 wt=%, in
particular 20 to 40 wt-%,the component in) is present in an amount in the range from 20 to
55 wt~%, in particular 30 to 45 wt~%, the component C) is present in an amount in the range
from 0,2 to 3 wt-%, in particular 0,5 to 2 wt—%, and the component d) is present in an
amount in the range from 10 to 40 wt—%, in particular 15 to 35 wt—%, wherein in each case
the sum of components a), b), c) and cl) always adds up to 100 Wt-%,
Particularly preferable results as to an improved sweetening profile, i.e. a sweetening pro-
file coming close to or being even essentially identical to that of natural sugar, that is a so-
called natural sweetening profile, is obtained with the third embodiment of the sweetening
composition of the present invention in which component b) comprises or consists of su-
cralose, saecharin and cyclamate or, alternatively, in which component b) comprises or
consists of at least one stevia compound, in particular selected from the group consisting of
steviol glycosides, rebaudiosides and mixtures thereof, saccharin and cyclamate.
In the sweetening compositions of the third embodiment of the invention, in particular in
the form of an aqueous composition, preferably in the form of a beverage, acesulfam and/ or
aspartame is preferably present in an amount in the range from 25 to 250 mg/l, more pref-
erably in the range from 50 to 200 mg/l and in particular in the range from 75 to 150 mg/l.
Alternatively or in addition? in said sweetening compositions of the third embodiment of
the invention sucralose preferably is present in an amount in the range from 20 to 750
mg/l, more preferably in the range from 40 mg/1 to 550 mg/l and in particular in the range
from no to 450 mg/’l. And, alternatively or in addition, in said sweetening compositions of
the third embodiment of the invention, and also in the preferred embodiment of the first
and second embodiment, neohesperidin preferably is present in an amount in the range
from o.oi mg/l to 20 mg/l, more preferably in the range from 0,1 mg/l to 15 mg/l and in
particular in the range from 1,0 to 10 mg/l. Alternatively or in acicijltion, in said sweetening
compositions of the third embodiment of the invention saccharin preferably is present in an
amount in the range from 10 mg/l to 750 mg/'1, more preferably in the range from 20 mg/l
WO 2018/122383 PCT/EP2017/084826
to 50o mg/l and in particular in the range from 30 to 400 mg/l, And, alternatively or in
addition, in said sweetening compositions of the third embodiment of the invention eyela-
mate preferably is present in an amount in the range from 10 mg/l to 500 mg/1, more pref-
erably in th.e range from 50 mg/1 to 300 mg/l and in particular in the range from 75 to 200
mg/l. And, alternatively or in addition, in said sweetening compositions ofthe third embod-
iment of the invention, and also in the preferred embodiment of the first and second em-
bodiment, thaumatine preferably is present in an amount in the range from 0.01 mg/l to 10
mg/l, more preferably in the range from 0,05 ‘mg/l to 5 mg/l and in particular in the range
from o,1 to 2 mg/l. And, alternatively or in addition, in said sweetening compositions of the
third embodiment of the invention rubusoside and/or at least one rubusoside derivative
preferably is present in an amount in the range from 5 to 200 mg/1, more preferably in the
range from 10 mg/1 to 150 mg/l and in particular in the range from 20 to 125 mg/l. And,
alternatively or in addition, in said sweetening compositions of the third embodiment of the
invention, and also in the preferred embodiment of the first and second embodiment,
phloretin preferably is present in an amount in the range from 1 to 250 mg/l, more prefera-
bly in the range from 5 mg/l to 20o mg/l and in particular in the range from 10 to 150 mg/l.
And, alternatively or in addition, in said sweetening compositions of the third embodiment
of the invention, and also in the preferred embodiment of the first and second embodiment,
trilobatin preferably is present in an amount in the range from 0,1 to 250 mg/1, more pref-
erably in the range from 1 mg/l to 1200 mg/l and in particular in the range from 5 to 150
mg/l. And, alternatively or in addition, in said sweetening compositions of the third embod-
iment of the invention, and also in the preferred embodiment of the first and second em.-
bodiment, rnonatin preferably is present in an amount in the range from 0.01 mg/l to 20
mg/l, more preferably in the range from 0,1 mg/l to 110 mg/l and in particular in the range
from 0,05 to 5 mgfl. And, alternatively or in addition, in said sweetening compositions of
the third embodiment of the invention hesperetin preferably is present in an amount in the
range from 1 to 750 mg/l, more preferably in the range from 10 mg/l to 50o mg/l and in
particular in the range from 25 to 250 mg/1.
In the sweetening compositions according to the first, second and third embodiment of the
present invention the at least one stevia compound preferabiy is a mixture comprising, in
particular consisting of, rebaudioside A, rebaudioside B and rebaudioside D wherein, based
on the total weight of rebaudioside A, rebaudioside B and rebaudioside D, rebandioside A is
present in an amount in the range from 80.0 to 99.0 wt—%, rebaudioside B is present in an
amount in the range from 0.1 to 1.5 wt—%, and rebaudioside D is present in an amount in
the range from 0.9 to 18.5 wt-%.
WO 2018/122383 PCT/EP2017/084826
Moreover, in the sweetening compositions according to the first, second and third embod-
iment of the present invention the at least one stevia eomponncl preferably is a mixture
comprising, in particular consisting of, rebeuclioside A, rehauclioside B and rehaudioside I)
wherein, based on the totai weight of rebaudioside A, rebaudiosicle B and rebaudioside D,
rebaudioside A is present in an amount in the range from 85.0 to 95.0 wt—%, rebaudioside B
is present in an amount in the range from 0.2 to 1.2 wt~%, and rehaudioside D is present in
an amount in the range from 4.8 to 13.8 wt-%.
Furthermore, in the sweetening compositions according to the first, seeoncl and third em-
bodiment of the present invention rebaudioside A is present in an amount in the range
from 86.0 to 94.3 wt-%, rebaudioside B is present in an amount in the range from 0.3 to
0.9 Wt»-%, and rehaudioside D is present in an amount in the range from 5.4 to 13.1 wt—%, in
each case based on the total weight of rehaudioside A, rebaudioside B and rebaudioside D.
In a particular preferred version of the sweetening compositions according to the first, sec~
ond and third embodiment of the present invention rehauclioside A is present in an amount
in the range from 90.5 to 94.0 wt-%, rehaudioside B is present in amount in the range from
0.2 to 1.0 wt—% and rebaudioside D is present in amount in the range from 5.8 to 8.5 wt-%,
based on the total weight of rebaudiosicle A, rehaudioside B and rebaudioside D, or
rehandioeide A is present in an amount in the range from 90.9 to 94.4 wt—%, rebeudioside B
is present in amount in the range from 0.2 to 0.5 wt-% and rebaudioside D is present in
amount in the range from 5.4 to 8.6 wt-%, in each case based on the total weight of rebau—
clioside A, rebaucliosicle B and rebaudioside D.
Steviolglycosides such as rebauciioside A, reband.iosicle B, rebaudioeide D, rehaudioside C,
rebauclioside E, rehaudioside F, stevioside, dnleosicle, ruhusoside and steviolhioside can be
detected and determined according to HPLC~UV as specified in J ECFA (2010) Steviol Gly-
eosides, FAD J ECFA Monograph 10, FAQ, Rome.
The problem underlying the present invention has also been solved by a sweetening compo»
sition, also referred to as fourth embodiment of a sweetening composition of the present
invention, comprising a) 0,1 to 50 g/l of a natural sweet-tasting carbohydrate, in particular
selected from the group consisting of natural sweet—tasting monosaccharirles, h) 40 to 120
g/l of a natural sweebtasting carbohydrate different from as), in particular selected from the
group consisting of natural sweebtasting disaecharides, and c) 30 to 300 mg/l rubusoeide
and/or at least one ruhueoside derivative and/or 0.01 mg/l to 20 mg/l, preferably in the
WO 2018/122383 PCT/EP2017/084826
range from 0,1 mg/i to 15 mg/l and more preferably in the range from 1,0 to 10 mg/l, neo-
hesperidin, or (1.01 mg/l to 10 mg/l, preferably in the range from 0,05 mg/l to 5 mg/l and
more preferably in the range from 0,1 to 2 mg/l, thaumatine or 1 to 250 mg/l, preferably in
the range from 5 mg/l to 200 mg/l and more preferably in the range from 10 to 150 mg/l,
phloretin or 0,1 to 250 mg/1, preferably in the range from 1 mg/l to 20o mg/l and more
preferably in the range from 5 to 150 mg/l, trilobatin or 0,01 mg/l to 20 mg/1, preferably in
the range from 0,1 mg/1 to 10 mg/l and more preferably in the range from o,o5 to 5 mg/l,
monatin or 1 to 750 mg/1, preferably in the range from 111 mg/l to 500 mg/l and more pref-
erably in the range from 25 to 250 mg/l, hesperetin or at least one enzyn1e~treated steviol
glyeosirle or any mixture thereof, in particular rubusosicle and/or at least one rubusoside
derivative am:l/ or neohesperidin and/or at least one enzymotreated steviol glyeoside.
Among the compounds of component C) of the fourth embodiment of the sweetening com-
position of the present invention rubusoside and/or at least one rubusoside derivative are
preferred, rubusoside being particularly preferred.
Said versions of the fourth embodiment of the present. invention are particularly preferred
which comprise a) o,5 to 30 g/l. of a natural sweet—tasting carbohydrate selected from the
group consisting of natural sweet-tasting rnonosaceharides, b) 70 to 110 g/l of a natural
sweet~tasting carbohydrate selected from the group consisting of natural sweet-tasting di-
saccharides, and e) 40 to 220 mg/l rubusosicile and/or at least one rubusoside derivative or
0,1 mg/l to 15 mg/l and ‘preferably 1,0 to 10 mg/l neohesperidin, or o,o5 mg/l to 5 mg/l and
preferably 0,1 to 2 mg/l thaumatine or 5 mg/l to 20o mg/l and preferably 1o to 150 mg/l
phloretin or 1 mg/l to 200 mg/l and preferably 5 to 150 mg/l trilobatin or 1),: mg/l to 10
mg/l and preferably o,o5 to 5 mg/l monatin or 10 mg/l to 500 mg/l and preferably 25 to
250 mg/l hesperetin,
In the sweetening compositions of the first to fourth embodiment of the present invention
the at least one natural sweet—tasting carbohydrate preferably is selected from the group
consisting of a natural sweet-tasting monosaccharide, a natural sweet—tasting disaceharide,
a sweet-tasting sugar alcohol and a mixture thereof. While said the sweet—tasting natural
monosaccharide preferably is selected from the group Consisting of fructose, glucose, man-
nose, rhamnose, xylose, tagatose, galactose, and mixtures thereof, said sweet-tasting natu-
ral disaeeharide is preferably selected from the group consisting of sucrose, lactose, maltose
and mixtures thereof. Moreover, said sweet-«tasting sugar alcohol preferably is selected
from the group consisting of erythritol, glycerol, lactltol, maltitol, mannitol, sorbitol, xylitol,
galaetitol and mixtures thereof,
WO 2018/122383 PCT/EP2017/084826
With the sweetening compositions of the first to fourth embodiment of the present inven-
tion it is particularly preferred to make use of sucrose as the sweet—tasting natural disaccha-
ride.
The sweetening compositions of the first to fourth embodiment of the present invention can
further comprise at least one flavoring ingredient selected from the group consisting of ga-
langal, cocoa, cinnamon, lemon, lemon juice concentrate, coca leaf, orange, orange oil, corn
mint, pine, cardamom, mace, clove, lime, lime oil, nutmeg, nutmeg oil, mustard seeds,
mustard seed oil, caramel, rosemary, pepper, honey, ginger, vanilla, licorice; licorice ex-
tract, cola nut and cola nut extract or mixtures thereof.
In a particularly preferred embodiment the sweetening compositions of the first to fourth
embodiment of the present invention further comprise taurine and/ or caffeine. According-
ly, the sweetening compositions of the first to fourth embodiment of the present invention
can be used for sweetening beverages, in particular soft drinks or energy drinks.
Interestingly, the sweetening compositions of the present invention are also suited to pre-
pare precursor compositions in the form of a syrup which can be easily stored and trans-
ported and can be used on demand for the preparation of in particular carbonated beverag-
The problem underlying the present invention has also been solved by a beverage compris-
ing; a sweetening composition according to any of the first to fourth embodiment of the pre-
sent invention. Here, the sweetening composition according to any of the first to fourth
embodiments of the present invention can already as such represent an aqueous composi-
tion, in particular a beverage. Aiternatively, said sweetening composition according to any
of the first to fourth embodiments of the present invention, without added water present,
can also represent a dry mixture, in particular in powder and/or particulate form. However,
even if the sweetening composition according to any of the first to fourth embodiments of
the present invention represent aqueous compositions still further ingredients such as fla-
vors or thickening agents may be added to form, for example, a commercial beverage.
Suitable beverages according to preferred embodiments are characterized in that rebaudi—
oside A, B and D in combination are present in the beverage in a concentration in the range
from 0.01 to 1.0 g/l, preferably from (32.05 to (3.75 g/l and more preferably from 0.1 to 0.6
g/l (determin.e~d at ambient temperature and 1 bar).
WO 2018/122383 PCT/EP2017/084826
Also those beverages according to the present invention are preferred in which the sweet-
tasting natural carbohydrates and the sweet-tasting sugar alcohols are present in combinae
tion in the beverage in a concentration not above 40 g/l, preferably in the range from 5 g/l
to 35 g/i and more preferably in the range from 10 g/l to 25 g/l (determined at ambient
temperature and 1 bar). Ambient temperature in the meaning of the present invention shall
mean room temperature, is a temperature in the range from 20°C to 25°C.
The beverages of the present invention comprise, in particular carbonated, soft drinks and
energy drinks. Suitable soft drinks also include cola—flavored soft drinks, wherein cola-
fiavorecl soft drinks also encompass cola-flavored-type soft drinks. Also these beverages,
when being sweetened with the sweetening composition in accordance with the present
irrvention, do not or do essentially not exhibit a slow onset of the sensation of sweetness but
provide a rather harmonic sweetening profile and do not or do essentially not have a bitter
or licorice-like aftertaste.
It is another benefit of sweetening compositions of the first to fourth embodiment of the
present invention that beverages can be obtained which, if at ail, contain natural sugars
such as sweetwtasthig carbohydrates andfor sweet—tasting sugar alcohois in a very reduced
amount.
The sweetening compositions of the first to fourth embodiment of present invention can
also comprise, for example when usedwith energy drinks, further ingredients such as sodi-
um citrate, glncoronolactone, inositol, at least one vitamin, e.g. niacin, pantothenic acid,
vitamin B6, vitamin B12, riboflavin, caustic caramel, caustic sulfite caramel, ammonia car-
amel, sulfite ammonia caramel or ascorbic acid or mixtures thereof.
The sweetening composition of the present invention can be used for sweetening beverages,
in particular soft drinks or energy drinks. The beneficial effects coming along with the use
of the sweetening composition of the present invention can in particular also be accom-
plished with carbonated beverages.
The problem of the present invention has also been solved by a method comprising the
steps of a) providing a sweetening composition according to the first to fourth embodiment
of the present invention, b) providing water and c) mixing components provided under a)
and la). The process of the present invention particularly further comprises the step (step
d}) of carbonating the beverage.
WO 2018/122383 PCT/EP2017/084826
According to another embodiment, the process of the present invention can further com-
prise the step of adding at least one thickening agent, at least one sweet—tasting natural car-
bohydrate, at least one sweetntasting sugar alcohol, at least one organic acid and/ or at least
one flavoring ingredient to the sweetening composition according to the first to fourth em~
bodiment of the present invention or to a mixture comprising water and one of said sweet»
ening compositions of the present invention. The aforementioned components may also be
added to water prior to mixing with any of said sweetening compositions of the present
invention. Here, the definitions provided above for thickening agent, sweet—tasting natural
carbohydrate, sweet—tasting sugar alcohol, organic acid and flavoring ingredient are appli-
cable as well both in terms of general information and preferred embodiments.
Furthermore, it is also possible that the sweet—tasting natural carbohydrates and/or at least
one sweet-tasting sugar alcohol are added to the mixture comprising water and one of the
first to fourth embodiment of the sweetening compositions of thevpresent invention prior to
and / or after the carbonating step, preferably prior to the carbonating step.
The first to fourth embodiments of the sweetening compositions of the present invention as
well as the beverages of the present invention, e. g. soft drinlrs or energy drinks, in one em-
bodiment can also comprise common additives such as amino acids, coloring agents, bulk-
ing agents, modified starches, texturizers, preservatives, antioxidants, emulsifiers, stabi-
iizers, gelling agents or arbitrary mixtures thereof.
With the present invention it hasvbeen surprisingly found that sweetening compositions are
accessible which do not exhibit a slow onset in the sweetening sensation. As an additionai
effect it is also possible to arrive at such sweetening compositions which do not have a bit-
ter aftertaste and/or which also do not have a metailic aftertaste. Moreover, it has surpris-
ingiy been found that with the sweetening cornpositions of the present invention an aroma
or sweetening profile can be accomplished which resembles that of beverages having been
sweetened with natural sugars, even with carbonated beverages. Furthermore, it has sur-
prisingly been found that with at least one tannin, in particular tannic acid and/ or tannic
acid derivatives, being present in the compositions of the present invention the long-lasting
sweetening sensations of artificial sweeteners as, for example, stevia compounds can be
shortened furnishing a natural or an essential natural sweetening sensation, that is a sweet-
ening profiie regularly caused by known high caloric sugars.
It is, thus, possible with the sweetening composition of the present invention to prepare
beverages, in particuiar carbonated beverages, such as soft drinks and energy drinks which
WO 2018/122383 PCT/EP2017/084826
though having a significantly reduced caloric content exhibit an improved sweetness and
aroma profile and which in a preferred embodiment also do not differ significantly in their
taste from conventional beverages having been sweetened with natural sugars and] or artifi-
cial sweeteners. This also includes that a sweetened sensation is perceived by the consumer
already at the very beginning. In addition, with the sweetening composition of the present
invention beverages can be obtained which do not have an insipid or blunt taste or mouth-
feel.
In the meaning of the present invention artificial sweeteners shall comprise all sweeteners
different from natural sweeteners such as natural rnonosaecharide and disaecharide sweet-
eners, e.g. glucose and sucrose.
The beverages of the present invention comprise, in particular carbonated, soft drinks and
energy drinks. Suitable soft drinks also include cola-flavored soft drinks, wherein cola-
ilavored soft drinks also encompass cola—ilaVored—type soft drinks. Also these beverages,
when being sweetened with the sweetening composition in accordance with the present
invention, do not or do essentially not exhibit a slow onset of the sensation of sweetness but
provide 3 rather harmonic sweetening profile and do not or do essentially not have a bitter
or licorice—1ike aftertaste.
That is, with the present invention, in particular with the combined use of rubusoside
and/ or at least one rubusoside derivative and/ or neohesperidin and/ or thegurnatine and/’ or
phloretin and/’ or trilobatin and/or rnonatin and/or hesperetin and/or at least one enzyme-
treated steviol glyc-oside, inparticnlar rubusoside and / or at least one rubusoside derivative,
and at least one tannin, in particular tannic acid and/or a tannic acid derivative, beverages
are accessible which though having been sweetened or eo—sweetened with artificial sweet-
eners such as stevia compounds exhibit a temporal sweetness profile as to onset time, dura-
tion, i.e. linger, and, if need be, intensity of sweetness being rather similar to that of su—
crose. Accordingly, the present invention not only allows shifting the slow onset of, for ex-
ample, stevia compounds towards that of sucrose, i.e. thereby exhibiting a more rapid on~
set, but also aids in significantly reducing the lingering effect.
Although modifications and changes maybe suggested by those skilled in the art, it is the
intention of the applicant to embody within the patent warranted hereon all changes and
modifications as reasonably and probably come within the scope of this contribution to the
art. The features of the present invention which are believed to be novel are set forth in de-
tail in the appended claims. The features disclosed in the description and in the claims
WO 2018/122383 PCT/EP2017/084826
could be essential alone 01‘ in every cornbinatian far the realization of the ixwention in its
different embodiments.
Claims (1)
- ClaimsA sweetening composition comprisingat least one natural sweet-tasting carbohydrate, in particular sucrose,at least one Stevie compound, in particular selected from the group consist-ing of steviol glycosicles, rebaudiosides and mixtures thereof,rnhusoside and/or at least one rubusoside derivative and/or neohesperidinand/ or thaumatine and/or phloretin and/ or trilobatin and/ or rnonatinand/or hesperetin and/or at least one enzyrne~treated steviol glycoside, inparticuiar rubusoside or at least one rubnsoside derivative or neohesperidinor at least one enzymewtreated steviol glycoside or any combination thereof,at least one tannin, in particular tannic acid anéf or at least one tannic acidderivative or a composition or extract containingtannic acid and/ or at leastone tannic acid derivative,wherein component (1), in particular tannic acid and/ or at least one tannicacid derivative, is present in an amount, based on the at least one tannin, inparticular tannic acid and the at least one tannic acid derivative, in the rangefrom 1 _mg/l to .400 mg/l, preferably in the range from 10 mg/1 to 300 mg/land more preferably in the range from 25 to 250 mg/1,and/ orwherein based on the total weight of component lo), component c), in par-ticular rubusoside and/ or at least one rubusoside derivative, and componentcl), in particular tannic acid and/ or at least one tannin acici derivative, thecomponent b) is present in an amount in the range from 45 to 75 wt-%, thecomponent (3), in particular the rubusosicle and/ or at least one rubusosidederivative, is present in an amount in the range from 2 to ago wt—%, and thecomponent d), in particular tannic acid and/’ or at least one tannic acid deriwative, is present in an amount in the range from 2 to 40 wt——%, wherein ineach case the sum of components b), c) and ti) aiwaye adds up to 100 wt~%.The sweetening composition according to claim 1, whereinthe at least one natural sweet—tasting, carbohydrate, in particular sucrose, is presentin an amount in the range from 5 to 80 g/l, preferably in the range from 15 g/1 to 70g/l and more preferably in the range from 25 to 55 g/1, and/or whereinWO
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/395,432 | 2016-12-30 | ||
EP16207626.9 | 2016-12-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ755861A true NZ755861A (en) |
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