US20120308687A1 - Process for co-crystallizing sucrose and a natural sweetener and the product thereof - Google Patents
Process for co-crystallizing sucrose and a natural sweetener and the product thereof Download PDFInfo
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- US20120308687A1 US20120308687A1 US13/587,696 US201213587696A US2012308687A1 US 20120308687 A1 US20120308687 A1 US 20120308687A1 US 201213587696 A US201213587696 A US 201213587696A US 2012308687 A1 US2012308687 A1 US 2012308687A1
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- US
- United States
- Prior art keywords
- low calorie
- liquid product
- product according
- calorie liquid
- natural sweetener
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Links
- 235000021096 natural sweeteners Nutrition 0.000 title claims abstract description 41
- 229930006000 Sucrose Natural products 0.000 title claims abstract description 20
- 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 title claims abstract description 20
- 239000005720 sucrose Substances 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title abstract description 34
- 239000013078 crystal Substances 0.000 claims abstract description 31
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims abstract description 10
- 239000000047 product Substances 0.000 claims description 35
- 239000012263 liquid product Substances 0.000 claims description 21
- 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 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 235000013399 edible fruits Nutrition 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 7
- 235000013361 beverage Nutrition 0.000 claims description 6
- 241000219357 Cactaceae Species 0.000 claims description 5
- 244000228451 Stevia rebaudiana Species 0.000 claims description 5
- 244000185386 Thladiantha grosvenorii Species 0.000 claims description 5
- 235000011171 Thladiantha grosvenorii Nutrition 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 235000005822 corn Nutrition 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229930003231 vitamin Natural products 0.000 claims description 4
- 239000011782 vitamin Substances 0.000 claims description 4
- 229940088594 vitamin Drugs 0.000 claims description 4
- 235000013343 vitamin Nutrition 0.000 claims description 4
- 240000007154 Coffea arabica Species 0.000 claims description 3
- 235000013334 alcoholic beverage Nutrition 0.000 claims description 3
- 235000014171 carbonated beverage Nutrition 0.000 claims description 3
- 235000016213 coffee Nutrition 0.000 claims description 3
- 235000013353 coffee beverage Nutrition 0.000 claims description 3
- 235000015243 ice cream Nutrition 0.000 claims description 3
- 235000004727 Opuntia ficus indica Nutrition 0.000 claims 2
- 240000009297 Opuntia ficus-indica Species 0.000 claims 2
- 235000014443 Pyrus communis Nutrition 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 244000269722 Thea sinensis Species 0.000 claims 2
- 108700024897 plant thaumatin Proteins 0.000 claims 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims 2
- 235000003599 food sweetener Nutrition 0.000 abstract description 7
- 239000003765 sweetening agent Substances 0.000 abstract description 7
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 235000020357 syrup Nutrition 0.000 description 21
- 239000006188 syrup Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- 238000002288 cocrystallisation Methods 0.000 description 16
- 241000544066 Stevia Species 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004061 bleaching Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000004384 Neotame Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 description 4
- 235000019412 neotame Nutrition 0.000 description 4
- 108010070257 neotame Proteins 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000218218 Ficus <angiosperm> Species 0.000 description 3
- 240000001439 Opuntia Species 0.000 description 3
- 240000007326 Thaumatococcus daniellii Species 0.000 description 3
- 235000005266 Thaumatococcus daniellii Nutrition 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000003254 anti-foaming effect Effects 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 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 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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 1
- CANAPGLEBDTCAF-NTIPNFSCSA-N Dulcoside A 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@]23C(C[C@]4(C2)[C@H]([C@@]2(C)[C@@H]([C@](CCC2)(C)C(=O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC4)CC3)=C)O[C@H](CO)[C@@H](O)[C@@H]1O CANAPGLEBDTCAF-NTIPNFSCSA-N 0.000 description 1
- CANAPGLEBDTCAF-QHSHOEHESA-N Dulcoside A Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2O[C@]34CC[C@H]5[C@]6(C)CCC[C@](C)([C@H]6CC[C@@]5(CC3=C)C4)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H](O)[C@H]1O CANAPGLEBDTCAF-QHSHOEHESA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001512 FEMA 4601 Substances 0.000 description 1
- 239000001776 FEMA 4720 Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 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 1
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-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 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
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- 230000003292 diminished effect Effects 0.000 description 1
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000019203 rebaudioside A Nutrition 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 235000019202 steviosides Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose 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-QBMZZYIRSA-N 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
- C13B30/00—Crystallisation; Crystallising apparatus; Separating crystals from mother liquors ; Evaporating or boiling sugar juice
- C13B30/02—Crystallisation; Crystallising apparatus
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
- C13B50/00—Sugar products, e.g. powdered, lump or liquid sugar; Working-up of sugar
- C13B50/004—Agglomerated sugar products; Agglomeration
Definitions
- the present disclosure is related with the field of crystallization of sweetening products and more specifically, with co-crystallizing sugar and another natural sourced sweetener.
- U.S. Pat. No. 6,214,402 describes a co-crystallization process between sugar and N- ⁇ N-(3,3-dimethylbutyl)-L-alpha-aspartyl ⁇ -L-phenylalanine I-methylester.
- This disclosure is addressed to a method for preparing co-crystallized sugar comprising the steps of mixing sugar with water with stirring, heating the mixture to 120° C., seeding the mixture with a pre-mixture comprising N- ⁇ N-(3,3-dimethylbutyl)-L-alpha-aspartyl ⁇ L-phenylalanine I-methylester and sugar, removing the mixture from heat and allowing it to cool along with vigorous stirring.
- the seeding is carried out with the mixture of sugar and neotame being in the oversaturation zone, thus producing a shock seeding, which generates a non-homogeneous crystal distribution at the end of the process.
- the natural sweetener is fed after loading the batch foot in the equipment and this mixture is evaporated until saturation point is reached wherein an amount of powdered sugar and isopropyl alcohol suspension is added.
- the advantage of this methodology is that the added crystals in the seed, would be those that will be obtained at the end of the process having a homogeneous size and therefore having a lesser size variation coefficient.
- a starting liquor or syrup may have a brix of 55°, and may come from a white sugar melting, clearing, bleaching and filtering process, which generates a stock material having a better quality.
- U.S. Pat. No. 6,214,402 discloses a sugar and water mixture having 67° brix, with no previous treatment that improves or changes the characteristics of the solution.
- the present disclosure uses natural sweeteners and, besides, there is the possibility of adding some other aggregate which gives a special characteristic to said product.
- U.S. Pat. No. 4,362,757 describes a sugar crystallized product containing a heat sensitive substance, an acid substance or an inverted sugar.
- This crystallized sugar product is dry, granular, free flowing that does not become compact and is dispersible in water.
- the crystallized sugar products are formed in two steps: preparation of a sugar pre-mixture which is dry, granular or transformed with a heat sensitive substance, an inverted sugar or an acid, then it is crystallized through the concentration of the sugar syrup, adding a determined amount of pre-mixture and subjecting the mixture to impact.
- the present disclosure has notable advantages over the U.S. Pat. No. 4,362,757, because in the latter the work is done at a high temperature between 124 and 149° C. (255 and 300° F.), which increases the solubility of sucrose in water, causing the oversaturation of 95-98% of solids.
- the maximum operative temperature is 75° C. and its saturation step is reached in a percentage of solids between 79-81%.
- the process conditions have a direct impact on the final product.
- the present disclosure radically improves the size distribution of the sugar crystal.
- the present disclosure decreases the effect of temperature on the color of the final sugar and on the sugar juice or syrup resulting from the centrifugation process.
- the present disclosure improves the homogeneity of the natural sweetener and the aggregate in this case, due to the fact that the crystallization is carried out under a controlled and regulated manner, thereby avoiding oversaturation that leads to the generation of new sucrose crystals that do not contain the sweetener or the aggregate.
- This control and regulation of the temperature is done through vacuum in the equipment and constant conditions of heat through water steam.
- the oversaturation is controlled by removing the heat through water jackets or forced air flow, instead where the process can go out of control.
- the present disclosure relates to a new product formed by sugar which is co-crystallized along with other natural sweetener product and, optionally, another aggregate, said product has 100% homogeneity, increases the sweetening power by one and a half and fifty folds when compared to that of sugar and, furthermore, being a natural product it does not cause any harmful effects on the organism.
- the obtained sub-product in the centrifuging process is useful by obtaining a low calorie liquid sweetener.
- the disclosure is addressed to the preparation process of a sugar and a natural sweetener co-crystal and, optionally, another aggregate and to said product.
- the process is related with co-crystallization of sucrose with a natural sweetener in a vacuum pan under controlled pressure and temperature conditions and with the separation of the crystals from the sugar juice.
- the sub-product of the co-crystallization is used for producing a liquid sweetener having low calorie content such that a high percent of the stock material is used.
- FIG. 1 schematically shows a process in which sugar and a natural sweetener are co-crystallized for producing the co-crystal of the present disclosure and the utilization of the sub-product as a liquid natural sweetener;
- FIG. 2 shows a flow chart of a co-crystallization process according to some embodiments of the disclosure.
- Light liquor that obtained after melting a white sugar and has been subjected to clarification, bleaching with active carbon and filtration processes.
- Cooked mass Mixture of sugar and mother liquor unloaded from the vacuum pan, which comprises syrup and co-crystals of sucrose and natural sweetener.
- Co-crystallized sugar is a sugar obtained through co-crystallization of sucrose with natural sweetener.
- Syrup is the sugar juice obtained in the centrifugation and washing process of the cooked mass.
- Batch foot is the amount of light liquor and/or syrup enough for covering the calandria of the vacuum pan at the beginning of the batch.
- Brix Concentration unit equivalent to the percentage by weight of soluble solids containing a solution.
- Vacuum pan simple effect evaporation unit that operates under vacuum and which consists of a steam driven heating system, a cylinder-shaped body for cooking the mass. Feed tubing, condensates and incondensable gases output, valves and control instruments, dragging separator and condenser.
- Natural sweetener Product of natural source such as stevia, cactus pier fruit ( Opuntia ficus , indica L), Calonil (from the fruit of Momordica grosvenorii ), taumatine (from the Thaumatococcus daniellii ), corn derivatives and others.
- Stevia extract from the leave of the Stevia rebaudiana , Bertoni, which contains glycosides Stevioles as active principle (Steviosides, Rebaudioside A, Rebaudioside C and dulcoside A).
- the co-crystallization process of sugar with a natural sweetener and, optionally, an aggregate that grants some special characteristic to the product has as important characteristics obtaining a homogeneous, granular, free flowing, non-compactable product which sweetening power is between one and a half to fifty times that of sucrose, thus decreasing the calorie content per ration; in addition, it is a natural product that do not produce any deleterious effect to the human organism.
- reference number 1 corresponds to the equipment wherein the natural sweetener extract is obtained, optionally, mixed with an aggregate.
- Reference number 2 shows the vacuum pan wherein the liquor is loaded, an antifoaming agent and the prepared extract are added, under continuous mixing, the mixture is concentrated up to the range between 79° and 81° brix. At this point, the mixture is seeded with the alcoholic suspension and once the crystals are generated the liquor is slowly fed until 100% level is reached with 88° to 91° brix.
- the product obtained in 2 (cooked mass) is centrifuged in the equipment identified with numeral 3 .
- sugar co-crystallized with natural sweetener and, optionally, an aggregate is produced.
- a syrup sub-product with the natural sweetener is re-circulated as shown in reference number 2 in order to restart the co-crystallization process. This process is repeated until the syrup color complies with the specifications because during the repetition of this process said syrup tends to become darker.
- the recovered natural sweetener returns to the equipment identified in 1 wherein said sweetener is obtained and then the process restarts.
- the non-recovered syrup with natural sweetener is further treated in a bleaching step in order to, afterwards, obtain a liquid sweetener product having also low calories.
- sucrose solution light liquor or syrup
- sweetener 0.1% to 50% w/w of natural sweetener with respect to the amount of produced mass and, optionally, adding an aggregate in order to reach any special characteristic, to form a mixture
- the amount is determined by different variables such as the weight of the crystal in the mass, the initial size of the seed and the desired final size; which relate in the following manner:
- Suspension weight crystal weight in mass*((initial size/final size) 3 );
- Antifoaming substances that can be used with this disclosure are any of the following compounds: PROPEG DF 7990 M2 (produced by Protecnica Ingenieria S.A.), INTRASOL FK 35 (produced by Lipesa Colombia S.A.), Indol CS-100 (produced by Nopco Colombiana S.A.), Lipesa 9103 (produced by Lipesa Colombia), and Rhodorsil 70462 (Produced by Emulsiones Quimicas Ltda.).
- the natural sweetener used in this disclosure can be chosen among: stevia, Cactus pier fruit ( Opuntia ficus, Indica L), Calonil (from the fruit of Momordica grosvenorii ), Taumatine (from Thaumatococcus daniellii ), honey, sucralose, glucose, fructose, corn derivatives, lactose, polyols (sorbitol, Mannitol, Xilitol), Glycirine, Taumatine, Tagatose, Filodulcine, Osladine, Moneline and others. The most preferred being stevia.
- an aggregate is added in order to obtain any special characteristic such as flavor or any nutritive property.
- Said aggregate can be comprised by: calcium, citric acid, vitamins, fiber, minerals, herb extracts, etc.
- the present disclosure is also related to the sucrose and stevia co-crystal.
- Said cocrystal is characterized in that it comprises sugar, a natural sweetener and, optionally, an aggregate which give it special characteristics, and which is obtained through the above described process.
- the natural sweetener used in the crystal can be chosen among: stevia, polyols, Cactus pier fruit ( Opuntia ficus , Indica L), Calonil (from the fruit of Momordica grosvenorii ), Taumatine (from Thaumatococcus daniellii ).
- stevia is preferred.
- Said co-crystal can use some aggregates such as: calcium, citric acid, vitamins, fiber, minerals, herb extracts. Furthermore, said co-crystal has a size around 0.5-0.7 mm, preferably, 0.6 mm.
- This co-crystal has different applications in different fields such as: bakery, ice cream manufacturing, confectionary, carbonated beverages, coffees, teas, juice making, flavored water, energizing beverages, alcoholic beverages, lactic beverages, sodas.
- Said co-crystal bears a sweetening power between one and a half to fifty times that of plain sugar.
- said sweetening power is two times.
- this disclosure is also related with a sub-product obtained from the other portion of syrup mixed with 20-40% of the initial natural sweetener which is bleached with activated carbon and then mixed with water.
- This product is 1.2 to 10 times sweeter than sugar. Preferably 1.2 to 3 times and contains between 1-4 calories per gram, preferably between 1 and 2 calories per gram.
- FIG. 2 shows the flow diagram of the above explained crystallization process and that is submitted for additionally making clear the process of the present disclosure.
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Abstract
The invention relates to a preparation process of a co-crystal made of sugar and a natural sweetener and, eventually, another aggregate and with said product. The process is further related with co-crystallizing sucrose and a natural sweetener in a vacuum pan under controlled pressure and temperature conditions and separating the crystal from the sugar juice. At the end of the process, the co-crystallized sub-products are used for producing a low calorie content liquid sweetener such that in a high percentage all the stock material is used.
Description
- This is a divisional application of U.S. application Ser. No. 12/304,492, filed on Oct. 6, 2009, which application is a national stage filing under section 371 of PCT/IB2006/001664 filed on Jun. 13, 2006, each of which is incorporated herein by reference in its entirety.
- The present disclosure is related with the field of crystallization of sweetening products and more specifically, with co-crystallizing sugar and another natural sourced sweetener.
- U.S. Pat. No. 6,214,402, describes a co-crystallization process between sugar and N-{N-(3,3-dimethylbutyl)-L-alpha-aspartyl}-L-phenylalanine I-methylester. This disclosure is addressed to a method for preparing co-crystallized sugar comprising the steps of mixing sugar with water with stirring, heating the mixture to 120° C., seeding the mixture with a pre-mixture comprising N-{N-(3,3-dimethylbutyl)-L-alpha-aspartyl}L-phenylalanine I-methylester and sugar, removing the mixture from heat and allowing it to cool along with vigorous stirring.
- In connection with the state of the art documents, it is important to mention the existing differences. In said document U.S. Pat. No. 6,214,402 the sugar and neotame co-crystallization process was carried out under atmospheric pressure conditions, that is, at high temperatures, in this specific case at 120° C. In the case of the present disclosure, the product is obtained under vacuum pressure, 60 KPa-75 KPa, which corresponds to an operative temperature of 60° C.-75° C. In the latter case, the darkening of the mother liquor is significantly diminished, which darkening is promoted by high temperatures, which enhances the color of the final product.
- On the other hand, in the co-crystallization process of sugar and neotame, the seeding is carried out with the mixture of sugar and neotame being in the oversaturation zone, thus producing a shock seeding, which generates a non-homogeneous crystal distribution at the end of the process. In the co-crystallization process of the present disclosure, the natural sweetener is fed after loading the batch foot in the equipment and this mixture is evaporated until saturation point is reached wherein an amount of powdered sugar and isopropyl alcohol suspension is added. The advantage of this methodology is that the added crystals in the seed, would be those that will be obtained at the end of the process having a homogeneous size and therefore having a lesser size variation coefficient.
- Furthermore, no reference is made to separating the crystals of sugar juice or syrup in the patent for the sugar and neotame co-crystallization; a necessary operation for the obtention of a free-flowing granular product, that do not become compacted or compressed.
- In the co-crystallization process of a preferred embodiment of the present disclosure, a starting liquor or syrup may have a brix of 55°, and may come from a white sugar melting, clearing, bleaching and filtering process, which generates a stock material having a better quality. U.S. Pat. No. 6,214,402, discloses a sugar and water mixture having 67° brix, with no previous treatment that improves or changes the characteristics of the solution.
- Finally, the present disclosure uses natural sweeteners and, besides, there is the possibility of adding some other aggregate which gives a special characteristic to said product.
- U.S. Pat. No. 4,362,757 describes a sugar crystallized product containing a heat sensitive substance, an acid substance or an inverted sugar. This crystallized sugar product is dry, granular, free flowing that does not become compact and is dispersible in water. The crystallized sugar products are formed in two steps: preparation of a sugar pre-mixture which is dry, granular or transformed with a heat sensitive substance, an inverted sugar or an acid, then it is crystallized through the concentration of the sugar syrup, adding a determined amount of pre-mixture and subjecting the mixture to impact.
- The present disclosure has notable advantages over the U.S. Pat. No. 4,362,757, because in the latter the work is done at a high temperature between 124 and 149° C. (255 and 300° F.), which increases the solubility of sucrose in water, causing the oversaturation of 95-98% of solids. In the present disclosure, the maximum operative temperature is 75° C. and its saturation step is reached in a percentage of solids between 79-81%. The process conditions have a direct impact on the final product. The present disclosure radically improves the size distribution of the sugar crystal. The present disclosure decreases the effect of temperature on the color of the final sugar and on the sugar juice or syrup resulting from the centrifugation process. The present disclosure improves the homogeneity of the natural sweetener and the aggregate in this case, due to the fact that the crystallization is carried out under a controlled and regulated manner, thereby avoiding oversaturation that leads to the generation of new sucrose crystals that do not contain the sweetener or the aggregate. This control and regulation of the temperature is done through vacuum in the equipment and constant conditions of heat through water steam. In the mentioned US patent the oversaturation is controlled by removing the heat through water jackets or forced air flow, instead where the process can go out of control.
- The present disclosure relates to a new product formed by sugar which is co-crystallized along with other natural sweetener product and, optionally, another aggregate, said product has 100% homogeneity, increases the sweetening power by one and a half and fifty folds when compared to that of sugar and, furthermore, being a natural product it does not cause any harmful effects on the organism. In addition, the obtained sub-product in the centrifuging process is useful by obtaining a low calorie liquid sweetener.
- The disclosure is addressed to the preparation process of a sugar and a natural sweetener co-crystal and, optionally, another aggregate and to said product. The process is related with co-crystallization of sucrose with a natural sweetener in a vacuum pan under controlled pressure and temperature conditions and with the separation of the crystals from the sugar juice.
- At the end of the process the sub-product of the co-crystallization is used for producing a liquid sweetener having low calorie content such that a high percent of the stock material is used.
- In order to have greater clearness and understanding of the disclosure, the following figures illustrate a co-crystallization process in which:
-
FIG. 1 schematically shows a process in which sugar and a natural sweetener are co-crystallized for producing the co-crystal of the present disclosure and the utilization of the sub-product as a liquid natural sweetener; and -
FIG. 2 shows a flow chart of a co-crystallization process according to some embodiments of the disclosure. - The present description will use the terms in the sense defined as follows:
- Light liquor: that obtained after melting a white sugar and has been subjected to clarification, bleaching with active carbon and filtration processes.
- Cooked mass: Mixture of sugar and mother liquor unloaded from the vacuum pan, which comprises syrup and co-crystals of sucrose and natural sweetener.
- Co-crystallized sugar: is a sugar obtained through co-crystallization of sucrose with natural sweetener.
- Syrup: is the sugar juice obtained in the centrifugation and washing process of the cooked mass.
- Batch foot: is the amount of light liquor and/or syrup enough for covering the calandria of the vacuum pan at the beginning of the batch.
- Brix: Concentration unit equivalent to the percentage by weight of soluble solids containing a solution.
- Vacuum pan: simple effect evaporation unit that operates under vacuum and which consists of a steam driven heating system, a cylinder-shaped body for cooking the mass. Feed tubing, condensates and incondensable gases output, valves and control instruments, dragging separator and condenser.
- Natural sweetener: Product of natural source such as stevia, cactus pier fruit (Opuntia ficus, indica L), Calonil (from the fruit of Momordica grosvenorii), taumatine (from the Thaumatococcus daniellii), corn derivatives and others.
- Stevia: extract from the leave of the Stevia rebaudiana, Bertoni, which contains glycosides Stevioles as active principle (Steviosides, Rebaudioside A, Rebaudioside C and dulcoside A).
- Batch: A batch of cooked mass.
- The co-crystallization process of sugar with a natural sweetener and, optionally, an aggregate that grants some special characteristic to the product, has as important characteristics obtaining a homogeneous, granular, free flowing, non-compactable product which sweetening power is between one and a half to fifty times that of sucrose, thus decreasing the calorie content per ration; in addition, it is a natural product that do not produce any deleterious effect to the human organism.
- In
FIG. 1 ,reference number 1 corresponds to the equipment wherein the natural sweetener extract is obtained, optionally, mixed with an aggregate. Reference number 2 shows the vacuum pan wherein the liquor is loaded, an antifoaming agent and the prepared extract are added, under continuous mixing, the mixture is concentrated up to the range between 79° and 81° brix. At this point, the mixture is seeded with the alcoholic suspension and once the crystals are generated the liquor is slowly fed until 100% level is reached with 88° to 91° brix. - The product obtained in 2 (cooked mass) is centrifuged in the equipment identified with
numeral 3. Herein, sugar co-crystallized with natural sweetener and, optionally, an aggregate is produced. Furthermore, a syrup sub-product with the natural sweetener is re-circulated as shown in reference number 2 in order to restart the co-crystallization process. This process is repeated until the syrup color complies with the specifications because during the repetition of this process said syrup tends to become darker. - When the syrup falls out of the specifications due to repeated and successive cocrystallization processes (i.e., the color of the re-circulated syrup is found above 1600 UI-1800 UI), then the process continues with recovering the greater amount of the natural sweetener, taking into account its solubility in order to use the adequate solvent. This step occurs in reference number 4.
- The recovered natural sweetener returns to the equipment identified in 1 wherein said sweetener is obtained and then the process restarts.
- The non-recovered syrup with natural sweetener is further treated in a bleaching step in order to, afterwards, obtain a liquid sweetener product having also low calories.
- Finally, the crystallization process of the present disclosure comprises the following steps:
- Adding an antifoaming agent to the liquor or syrup (batch foot) in order to avoid the foam provoked by the natural sweetener in a percentage of 0.006% to 10% (w/w) to form a sucrose solution;
- Mixing with mechanical stifling the sucrose solution (light liquor or syrup) with while adding 0.1% to 50% w/w of natural sweetener with respect to the amount of produced mass and, optionally, adding an aggregate in order to reach any special characteristic, to form a mixture;
- Concentrating the above mixture up to saturation point of sucrose, 79° to 81° brix, in a vacuum pan at a working pressure of 60 KPa to 75 KPa and a temperature between 60° C. to 75° C. to form a concentrate;
- Adding a powdered sugar suspended in isopropyl alcohol to the concentrate, which is then used as seed for crystallizing the previous solution in the saturation zone. The amount is determined by different variables such as the weight of the crystal in the mass, the initial size of the seed and the desired final size; which relate in the following manner:
-
Suspension weight=crystal weight in mass*((initial size/final size)3); - Feeding the light liquor or syrup in a constant and slow manner into a sugar evaporator, maintaining the crystallized solution in the “meta-stable zone”, in order to avoid the spontaneous generation of new crystals or dilution of those previously formed. This step is carried out until the equipment reaches 100% of its level, wherein the co-crystallized sucrose and natural sweetener crystal has reached a size of 0.5 to 0.7 mm average aperture;
-
- evaporating the remaining water from the resulting suspension until reaching 88° and 91° Bx;
- unloading the resulting evaporated mass in order to carry out the separation of the crystals from the sugar juice or syrup through centrifuging at a velocity between 1100 and 1300 rpm to form a supernatant comprising the sugar juice or syrup and residual uncrystallized natural sweetener product and a pellet comprising the co-crystals;
- re-circulating a portion of the obtained supernatant at the end of the co-crystallization process (centrifuging) as necessary while it does not loose the color established by the product specifications;
- recovering from a second portion of the supernatant between 1 and 90% of the natural sweetener with a solvent in which said natural sweetener is soluble;
- Bleaching the remaining syrup and natural sweetener mixture, with a bleaching product and obtaining a low calorie liquid product, containing between 15-60% sucrose, 0.01-8% natural sweetener and 40-85% water, which has a sweetening power between 1.2 and 10 times higher than that of sugar.
- Antifoaming substances that can be used with this disclosure are any of the following compounds: PROPEG DF 7990 M2 (produced by Protecnica Ingenieria S.A.), INTRASOL FK 35 (produced by Lipesa Colombia S.A.), Indol CS-100 (produced by Nopco Colombiana S.A.), Lipesa 9103 (produced by Lipesa Colombia), and Rhodorsil 70462 (Produced by Emulsiones Quimicas Ltda.).
- The natural sweetener used in this disclosure can be chosen among: stevia, Cactus pier fruit (Opuntia ficus, Indica L), Calonil (from the fruit of Momordica grosvenorii), Taumatine (from Thaumatococcus daniellii), honey, sucralose, glucose, fructose, corn derivatives, lactose, polyols (sorbitol, Mannitol, Xilitol), Glycirine, Taumatine, Tagatose, Filodulcine, Osladine, Moneline and others. The most preferred being stevia.
- Optionally, an aggregate is added in order to obtain any special characteristic such as flavor or any nutritive property. Said aggregate can be comprised by: calcium, citric acid, vitamins, fiber, minerals, herb extracts, etc.
- The present disclosure is also related to the sucrose and stevia co-crystal. Said cocrystal is characterized in that it comprises sugar, a natural sweetener and, optionally, an aggregate which give it special characteristics, and which is obtained through the above described process.
- The natural sweetener used in the crystal can be chosen among: stevia, polyols, Cactus pier fruit (Opuntia ficus, Indica L), Calonil (from the fruit of Momordica grosvenorii), Taumatine (from Thaumatococcus daniellii). In particular, stevia is preferred.
- Said co-crystal can use some aggregates such as: calcium, citric acid, vitamins, fiber, minerals, herb extracts. Furthermore, said co-crystal has a size around 0.5-0.7 mm, preferably, 0.6 mm.
- This co-crystal has different applications in different fields such as: bakery, ice cream manufacturing, confectionary, carbonated beverages, coffees, teas, juice making, flavored water, energizing beverages, alcoholic beverages, lactic beverages, sodas.
- Said co-crystal bears a sweetening power between one and a half to fifty times that of plain sugar. Preferably said sweetening power is two times.
- Finally, this disclosure is also related with a sub-product obtained from the other portion of syrup mixed with 20-40% of the initial natural sweetener which is bleached with activated carbon and then mixed with water. This product is 1.2 to 10 times sweeter than sugar. Preferably 1.2 to 3 times and contains between 1-4 calories per gram, preferably between 1 and 2 calories per gram.
-
FIG. 2 shows the flow diagram of the above explained crystallization process and that is submitted for additionally making clear the process of the present disclosure. - 2% of stevia is added to the liquor previously fed and mixed with 0.1% of antifoaming. This new mixture is concentrated up to 80° Bx and then 20 ml of suspension is added. After the generation of the crystals liquor is fed until 100% level and an 89% brix are reached. This mass is centrifuged at 1200 rpm. The result is a white color product of co-crystallized sugar and stevia. The approximate proportion of sugar with respect to stevia is around 99.6% to 0.4%. Its sweetening power is, around, two times that of only sugar. The resulting syrup coming from the centrifugation is mixed with ethylic alcohol and 80% of the initial stevia is recovered, which is then re-circulated. The other portion of the syrup mixed with 20% of the initial stevia, is bleached with ionic interchange resin and afterwards is mixed with water. This product is 1.6 times sweeter than sugar and contains 2 calories per gram.
Claims (20)
1. A low calorie liquid product comprising:
about 15 to about 60% (w/w) of sucrose;
about 0.01 to about 8% (w/w) of natural sweetener; and
about 40 to about 85% (w/w) water,
wherein the low calorie liquid product has a sweetening power of about 1.2 to about 10 times that of sugar.
2. A low calorie liquid product according to claim 1 , wherein the natural sweetener product is selected from the group consisting of stevia, Opuntia ficus-indica L cactus pear fruit, Momordica grosvenorii fruit calonil, Thaumatococcus daniellii thaumatin, corn derivatives, and combinations thereof.
3. A low calorie liquid product according to claim 1 , wherein the natural sweetener is stevia.
4. A low calorie liquid product according to claim 1 , wherein the sucrose and the natural sweetener form co-crystals.
5. A low calorie liquid product according to claim 4 , wherein the size of the co-crystals is about 0.5 mm to about 0.7 mm.
6. A low calorie liquid product according to claim 4 , wherein the size of the co-crystals is about 0.6 mm.
7. A low calorie liquid product according to claim 1 further comprising an aggregate.
8. A low calorie liquid product according to claim 7 , wherein the aggregate is selected from the group consisting of calcium, citric acid, a vitamin, fiber, a mineral, an herb extract, and combinations thereof.
9. A consumable product comprising a low calorie liquid product according to claim 1 .
10. A consumable product according to claim 9 , wherein the consumable product is selected from the group consisting of a bakery item, an ice-cream, a confectionary item, a carbonated beverage, a coffee, a tea, a juice, a flavored water, an energy beverage, an alcoholic beverage, a lactic beverage, a soda, and combinations thereof.
11. A low calorie liquid product comprising:
about 40 to about 50% of sucrose (w/w);
about 0.5 to about 3% of natural sweetener (w/w); and
about 40 to about 85% (w/w) water, and
wherein the low calorie liquid product has a preferred sweetening power of about 1.2 to about 3 times that of sugar.
12. A low calorie liquid product according to claim 11 , wherein the natural sweetener product is selected from the group consisting of stevia, Opuntia ficus-indica L cactus pear fruit, Momordica grosvenorii fruit calonil, Thaumatococcus daniellii thaumatin, corn derivatives, and combinations thereof.
13. A low calorie liquid product according to claim 12 , wherein the natural sweetener is stevia.
14. A low calorie liquid product according to claim 11 , wherein the sucrose and the natural sweetener form co-crystals.
15. A low calorie liquid product according to claim 14 , wherein the size of the co-crystals is about 0.5 mm to about 0.7 mm.
16. A low calorie liquid product according to claim 14 , wherein the size of the co-crystals is about 0.6 mm.
17. A low calorie liquid product according to claim 11 further comprising an aggregate.
18. A low calorie liquid product according to claim 17 , wherein the aggregate is selected from the group consisting of calcium, citric acid, a vitamin, fiber, a mineral, an herb extract, and combinations thereof.
19. A consumable product comprising a low calorie liquid product according to claim 11 .
20. A consumable product according to claim 19 , wherein the consumable product is selected from the group consisting of a bakery item, an ice-cream, a confectionary item, a carbonated beverage, a coffee, a tea, a juice, a flavored water, an energy beverage, an alcoholic beverage, a lactic beverage, a soda, and combinations thereof.
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| US13/587,696 US20120308687A1 (en) | 2006-06-13 | 2012-08-16 | Process for co-crystallizing sucrose and a natural sweetener and the product thereof |
| US14/175,913 US20140154359A1 (en) | 2006-06-13 | 2014-02-07 | Process for co-crystallizing sucrose and a natural sweetener and the product thereof |
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| PCT/IB2006/001664 WO2007144683A1 (en) | 2006-06-13 | 2006-06-13 | Process for cocrystallization of saccharose and a natural sweetener and the product obtained |
| US30449209A | 2009-10-06 | 2009-10-06 | |
| US13/587,696 US20120308687A1 (en) | 2006-06-13 | 2012-08-16 | Process for co-crystallizing sucrose and a natural sweetener and the product thereof |
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| US20140154359A1 (en) * | 2006-06-13 | 2014-06-05 | Ingenio Del Cauca S.A. -Incauca S.A. | Process for co-crystallizing sucrose and a natural sweetener and the product thereof |
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| DE602005019587D1 (en) * | 2004-07-30 | 2010-04-08 | Vb Medicare Pvt Ltd | SWEET COMPOSITION WITH REDUCED CALORIE CONTENT |
| MX2008015937A (en) * | 2006-06-13 | 2009-04-01 | Ingenio Del Cauca S A Incauca | Process for cocrystallization of saccharose and a natural sweetener and the product obtained. |
-
2006
- 2006-06-13 MX MX2008015937A patent/MX2008015937A/en active IP Right Grant
- 2006-06-13 WO PCT/IB2006/001664 patent/WO2007144683A1/en not_active Ceased
- 2006-06-13 US US12/304,492 patent/US8404297B2/en active Active
-
2008
- 2008-12-12 EC EC2008008977A patent/ECSP088977A/en unknown
-
2012
- 2012-08-16 US US13/587,696 patent/US20120308687A1/en not_active Abandoned
-
2014
- 2014-02-07 US US14/175,913 patent/US20140154359A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS611377A (en) * | 1984-06-13 | 1986-01-07 | Toyo Riken Kk | Preparation of vinegar beverage good for health |
| US20060019019A1 (en) * | 2004-07-23 | 2006-01-26 | Rohaly Thomas W | Lemon beverage |
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| Smith, J., Hong-Shum, L. 2003. Food Additives Data Book. pp. 982-986. Blackwell Publishing. Online version available at: http://www.knovel.com/web/portal/browse/display?_EXT_KNOVEL_DISPLAY_bookid=1381&VerticalID=0. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140154359A1 (en) * | 2006-06-13 | 2014-06-05 | Ingenio Del Cauca S.A. -Incauca S.A. | Process for co-crystallizing sucrose and a natural sweetener and the product thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP088977A (en) | 2009-01-30 |
| US20100034945A1 (en) | 2010-02-11 |
| US20140154359A1 (en) | 2014-06-05 |
| US8404297B2 (en) | 2013-03-26 |
| MX2008015937A (en) | 2009-04-01 |
| WO2007144683A1 (en) | 2007-12-21 |
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| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: INGENIO DEL CAUCA S.A. - INCAUCA S.A., COLOMBIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:ARANGO MORENO, DIANA MARIA;REEL/FRAME:028814/0369 Effective date: 20090220 |
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| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |
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| AS | Assignment |
Owner name: INGENIO DEL CAUCA S.A. - INCAUCA S.A., COLOMBIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:ARANGO MORENO, DIANA MARIA;REEL/FRAME:037505/0370 Effective date: 20090220 |