WO2014145276A1 - Carbohydrate compositions - Google Patents
Carbohydrate compositions Download PDFInfo
- Publication number
- WO2014145276A1 WO2014145276A1 PCT/US2014/030010 US2014030010W WO2014145276A1 WO 2014145276 A1 WO2014145276 A1 WO 2014145276A1 US 2014030010 W US2014030010 W US 2014030010W WO 2014145276 A1 WO2014145276 A1 WO 2014145276A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- carbohydrate composition
- glycosidic
- less
- ranging
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 547
- 150000001720 carbohydrates Chemical class 0.000 title claims abstract description 522
- 238000000034 method Methods 0.000 claims abstract description 68
- 235000019621 digestibility Nutrition 0.000 claims abstract description 62
- 235000013305 food Nutrition 0.000 claims abstract description 34
- 239000000047 product Substances 0.000 claims description 74
- 238000011282 treatment Methods 0.000 claims description 71
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 66
- 239000006188 syrup Substances 0.000 claims description 60
- 235000020357 syrup Nutrition 0.000 claims description 60
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 56
- 239000008103 glucose Substances 0.000 claims description 53
- 240000008042 Zea mays Species 0.000 claims description 43
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 43
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 43
- 235000005822 corn Nutrition 0.000 claims description 43
- 229920001542 oligosaccharide Polymers 0.000 claims description 38
- 150000002482 oligosaccharides Chemical class 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 33
- 101000883066 Chassalia parviflora Circulin-F Proteins 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 238000000926 separation method Methods 0.000 claims description 24
- 239000004615 ingredient Substances 0.000 claims description 21
- 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 claims description 19
- 239000000600 sorbitol Substances 0.000 claims description 19
- 235000013325 dietary fiber Nutrition 0.000 claims description 17
- 235000013361 beverage Nutrition 0.000 claims description 14
- 239000008121 dextrose Substances 0.000 claims description 13
- 235000003599 food sweetener Nutrition 0.000 claims description 11
- 239000003765 sweetening agent Substances 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 9
- 239000000796 flavoring agent Substances 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
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- 239000007788 liquid Substances 0.000 claims description 7
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- 235000015872 dietary supplement Nutrition 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 5
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- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
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- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 40
- 150000004676 glycans Chemical class 0.000 description 29
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- 239000007858 starting material Substances 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 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 13
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
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- 230000003197 catalytic effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 239000007800 oxidant agent Substances 0.000 description 6
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- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
Definitions
- the disclosure relates to carbohydrate compositions having reduced sugar and low digestibility, methods of making the carbohydrate compositions, and food products comprising the carbohydrate compositions.
- sweeteners vary according to their carbohydrate compositions.
- One form of traditional nutrititive sweetener includes starch- derived syrups.
- starch-derived syrups With respect to the carbohydrate composition of traditional starch-derived syrups, the sweetener industry typically produces products (i.e., a syrup product obtained from the hydrolysis of starch) containing in the range of from 15% to 99% sugar (glucose or dextrose, fructose and maltose) with the most widely used syrups containing more than 25% sugar (such as, for example, 43 DE and 63 DE corn syrups).
- 25% sugar such as, for example, 25 DE, 28 DE, and 36 DE corn syrups
- 25% sugar are not very sweet and are extremely viscous and thick, making it a processing challenge to use such syrups due to, for example, high resistance to pumping, high resistance to flow, and high adhesiveness to processing equipment.
- traditional starch-derived syrups e.g. corn syrups
- carbohydrate compositions less than 25% sugar have higher concentrations of polysaccharides (DP16+), which may lead to undesirable properties in certain food applications, e.g. causing foodstuffs to harden more quickly than those having more than 25% sugar and lower
- carbohydrate materials such as polydextrose, resistant maltodextrin, and soluble corn fiber have gained popularity in recent years as substitutes for traditional carbohydrates (e.g. glucose or corn syrup or sucrose).
- traditional carbohydrates e.g. glucose or corn syrup or sucrose.
- Polydextrose, resistant maltodextrin, and soluble corn fiber are reported to be useful in food products to totally or partially replace higher calorie ingredients such as traditional carbohydrates, and to augment artificial sweeteners when replacing sugars.
- Polydextrose for example, delivers only 1 kcal/gram, which is about 25% the value of glucose or traditional starch-derived syrups.
- these reduced-sugar, reduced-calorie carbohydrates are found to lack needed functionalities in certain applications.
- these reduced- sugar, reduced-calorie carbohydrates have high viscosities due to their high molecular weights.
- water can be added to dilute these carbohydrates, resulting in higher water activity and thus more susceptibility to microbial contamination.
- the high molecular weights of these carbohydrates will result in undesired functional outcomes in food products, such as hardening.
- these reduced- sugar, reduced-calorie carbohydrates while being less digestible, often have a darker color and off-flavor that have to be removed by additional treatments such as carbon adsorption.
- a reduced-sugar, reduced-calorie, and/or low-digestibility carbohydrate composition with desirable molecular characteritics is, therefore, still needed to provide reduced-sugar and/or lower-digestible sweeteners that have desired viscosities, e.g. having satisfactory processing requirements, and desired functionalities, e.g. when used in the production of food and beverage products.
- desired viscosities e.g. having satisfactory processing requirements, and desired functionalities, e.g. when used in the production of food and beverage products.
- food manufacturers are demanding from its suppliers a reduced- sugar, lower-digestible syrup having a viscosity similar to that of a 43 DE syrup.
- FIG. 1 is a chromatogram of 2A feed from Example 2.
- FIG. 2 is a chromatogram of 2A product from Example 2, Table 4.
- FIG. 3 is a chromatogram of 2B feed from Example 2.
- FIG. 4 is a chromatogram of 2B product from Example 2, Table 4.
- FIG. 5 is a chromatogram of polydextrose from Table 4.
- FIG. 6 is a chromatogram of Promitor-L85 from Table 4.
- FIG. 7 is a graph of gas production comparing the carbohydrate composition and liquid inulin.
- FIG. 8 is a graph showing hardness for granola bars prepared with 25% reduced sugar, incorporating carbohydrate compositions made according to an embodiment of the disclosure.
- FIG. 9 is a graph showing hardness for granola bars prepared with 50% reduced sugar, incorporating carbohydrate compositions made according to an embodiment of the disclosure.
- FIG. 10 is a graph showing harness for cookies prepared with 25% and 50% reduced sugar, incorporating carbohydrate compositions made according to an embodiment of the disclosure.
- FIG. 11 is a graph showing cookie spread for cookies prepared with 25% and 50% reduced sugar, incorporating carbohydrate compositions made according to an embodiment of the disclosure.
- FIG. 12 is a chromatogram of a 36 DE corn syrup, pre- and post-enzymatic digestion.
- FIG. 13 is a chromatogram of the carbohydrate composition prepared in Example 4, pre- and post-enzymatic digestion.
- digestibility refers to the digestion of the
- the terms “low-digestibility” or “lower- digestibility” and variations thereof are intended to mean ingredients in food products that are resistant, either partially or completely, to digestion in the upper gastrointestinal tract. These ingredients may be fermented or partially fermented in the large intestine. Lower-digestible ingredients may, in certain embodiments of the disclosure, offer one or more of the following health benefits: reduced caloric content; reduced or no effect on blood glucose levels; reduced cariogenic effect; modulation of the metabolism of triglycerides; reduced cholesterol; and improved gastric emptying.
- compositions described herein may be determined by an in vitro enzymatic treatment
- DP-N refers to the degree of polymerization, where N is the number of monomeric units (e.g., glucose or dextrose units) in the saccharide, reflecting the composition of the carbohydrate.
- DPI is a saccharide with one monomeric unit (monosaccharide)
- DP2 is a saccharide with two monomeric units (disaccharide).
- DP-N is expressed as a weight percent of an individual saccharide on a total carbohydrate (also referred to interchangeably herein as "saccharide”) dry weight basis.
- N represents a range
- DP3-7 is intended to indicate the total of all DP3 through DP7 saccharides
- DP 16+ is intended to indicate the total of all saccharides DP 16 and greater.
- the term "foodstuff” is intended to mean any substance suitable for consumption as food by humans and/or animals, e.g. any food and/or beverage product.
- linkage refers to a covalent C-glycosyl bond that joins a saccharide molecule to another saccharide molecule. Both a- and ⁇ -glycosidic bonds are referred to as "linkages" as used herein.
- a 1,6-linkage can be either an a-1,6- glycosidic bond or a P-l,6-glycosidic bond that links one glucose at C-l position with another glucose at C-6 position.
- 1,4-linkage, 1,2-linkage, 1,3-linkage or 4,6-linkage include both a- and ⁇ -glycosidic bonds.
- one saccharide molecule may join more than one other saccharide molecule through more than one linkages.
- PDI polydispersity index
- M n refers to the number average molecular weight, which is the average molecular weight of all components in the carbohydrate composition
- M w refers to the weight average molecular weight.
- traditional starch-derived carbohydrates are meant to include starch-derived carbohydrates prepared by traditional means, such as acid-acid, acid-enzyme, or enzyme-enzyme conversion methods, and having about 1-99DE (dextrose equivalents), such as about 1-20DE, about 20-50DE, 25-99DE or about 65-95DE.
- the traditional starch-derived carbohydrates may, in various exemplary embodiments, be starch products, dextrin products, maltodextrin products, glucose products, or dextrose products.
- the compositions comprising the traditional starch-derived carbohydrate may, in at least certain exemplary embodiments, be aqueous (or syrup).
- oligosaccharide refers to a carbohydrate with a DP of from at least 3 to at most 15.
- DP3-6, DP3-10, DP4-5, and DPI 1-15 are all examples of oligosaccharides.
- lower oligosaccharide is intended to mean oligosaccharides on the lower end of DP3-15, including, for example, DP3-10 or DP3-5.
- higher oligosaccharide is intended to mean oligosaccharides on the lower end of DP3-15, including, for example, DP3-10 or DP3-5.
- higher oligosaccharide is intended to mean oligosaccharides on the lower end of DP3-15, including, for example, DP3-10 or DP3-5.
- higher oligosaccharide is intended to mean oligosaccharides on the lower end of DP3-15, including, for example, DP3-10 or DP3-5.
- oligosaccharide is intended to mean oligosaccharides on the higher end of DP3-15, including for example DPI 1-15, DP12-15, DP13-15, DP14-15, and DP15.
- polysaccharide refers to a carbohydrate with a DP of at least 16.
- DP16+, DP16-20, DP21-30, DP31-40, DP41-50, DP51-100, DP101-150, DP 151-250, and DP251-500 are all examples of polysaccharides.
- the carbohydrate when the carbohydrate is referred to as having a DP of at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 11, at least 12, at least 13, at least 14, or at least 15, for example, the carbohydrate is characterized as having both oligosaccharides and polysaccharides.
- the carbohydrate composition has less than 35% DP11+, the carbohydrate composition has less than about 35% oligosaccharides and polysaccharides on a dry weight basis with a degree of polymerization of at least 11.
- sucrose refers to a nutritive carbohydrate sweetener consisting of specific monosaccharides (i.e., glucose, fructose, and galactose) and/or specific disaccharides (i.e., maltose, sucrose, and lactose).
- specific monosaccharides i.e., glucose, fructose, and galactose
- specific disaccharides i.e., maltose, sucrose, and lactose
- DS refers to the percent dry solids as determined by refractive index and using the computer program, Refractive Index Dry Substance (RI-DS), Standard Analytical Method E-54, Corn Refiners Association, 6 th Edition, 1977, E-54, pp. 1-11.
- viscosity refers to the resistance of a fluid to flow.
- the viscosity of an aqueous solution may be affected by temperature and solids concentration, for example. Viscosity is expressed in terms of centipoise (cPs) at a given temperature and a given % DS.
- cPs centipoise
- the disclosure relates to methods of making lower-digestible carbohydrate compositions.
- Various embodiments described provide for compositions comprising reduced sugar levels, while managing the formation of polysaccharides by using a two-step process, including (i) a first treatment process step, and (ii) a second separation step, that, when combined in a particular manner, produce carbohydrate compositions with
- the disclosure relates to unique carbohydrate compositions having reduced-sugar content and/or lower-digestibility than known carbohydrate composition.
- the unique carbohydrate compositions according to the disclosure possess unique molecular weight profiles that may result in advantageous physical (e.g., improved viscosity) and functional properties (e.g., reduced hardening).
- the unique carbohydrate compositions of the present disclosure have physical properties and functional properties different from existing reduced- sugar, reduced-calorie carbohydrates such as polydextrose (e.g., Litesse ® polydextrose), resistant dextrins and maltodextrin (e.g., Nutriose ® resistant dextrin and Fibersol-2 ® resistant
- soluble corn fibers e.g., Promitor soluble corn fiber
- the disclosure relates to food and/or beverage products comprising the unique carbohydrate compositions.
- Methods according to various embodiments of the disclosure relate to processes comprising (i) a first treatment step comprising treating a saccharide to produce a reduced-sugar and lower-digestibility intermediate composition, followed by (ii) a second separation step comprising separating the desirable portion of the intermediate composition.
- a first treatment step comprising treating a saccharide to produce a reduced-sugar and lower-digestibility intermediate composition
- a second separation step comprising separating the desirable portion of the intermediate composition.
- the methods described herein produce a final product with a carbohydrate composition having desired physical and/or functional properties.
- One objective of the first step in the process is to treat a saccharide in such a manner as to produce an intermediate composition with lower-digestibility and reduced-sugar content, while avoiding or minimizing the formation of higher-oligosaccharide and
- the treatment process maximizes the content of lower oligosaccharides (e.g., the DP3-4, DP3-5, and DP5
- the treatment step comprises contacting a saccharide feedstock (i.e., starting material) with at least one catalyst to obtain a feed composition.
- a saccharide feedstock i.e., starting material
- the feed composition is treated by being subjected to elevated temperature, and optionally reduced pressures, to promote
- carefully controlling the time, temperature, and/or pressure allows water levels to be reduced or removed, as needed, to promote the desired degree of polymerization.
- the treatment of the feed composition as described herein may, for example, be carried out in a vessel.
- the treatment of the feed composition may be controlled in order to obtain an intermediate carbohydrate composition having specified characteristics, for example a particular molecular weight distribution of specific saccharides, a particular digestibility, a particular viscosity, a particular M n , M w , and/or PDI.
- the treatment of the feed composition may be controlled in order to produce an intermediate composition having a digestibility ranging up to about 95%, such as about 10-90%, or about 30-60%; and/or a viscosity ranging from about
- 300-8000 cPs such as about 400-7800 cPs, or about 700-3000 cPs (measured at 75% DS; 38°C).
- the treatment of the feed composition may be controlled in order to obtain an intermediate carbohydrate composition having a M n ranging from about 200-1200 Da, such as about 400-700 Da; a M w ranging from about 300-3200 Da, such as about 700-1500 Da; and/or a PDI ranging from about 1.2-3.5, such as about 1.5-3.3, or about 1.75-2.15.
- the treatment of the feed composition may be controlled in a manner to produce an intermediate composition comprising, on a dry weight basis, an amount of DP1+2 ranging from about 10-85%, such as about 20-70%, about 30-50%, about 35-45%, or about 38- 42%; an amount of DP2s ranging from about 3-30%, such as about 5-26%, or about 10-24%; an amount of DP3-5 ranging from about 5-30%, such as about 7-28%, or about 10-25%; an amount of DP3+ ranging from about 50-70%, such as about 55-65%, or about 58-62%; and an amount of DP6+ ranging from about 8-65%, such as about 10-55%.
- an amount of DP1+2 ranging from about 10-85%, such as about 20-70%, about 30-50%, about 35-45%, or about 38- 42%
- an amount of DP2s ranging from about 3-30%, such as about 5-26%, or about 10-24%
- an amount of DP3-5 ranging from
- the intermediate composition according to the disclosure comprises an amount of DP1+2 ranging from about 18-63%, such as about 20-60%, or about 24-56%; an amount of DP2s ranging from about 10-25%, such as about 12-24%; an amount of DP3-5 ranging from about 25-30%, such as about 27-29%; an amount of DP3+ ranging from about 40-80%, such as about 42-78%, or about 44-76%; and an amount of DP6+ ranging from about 15-50%, such as about 17-48%.
- the treatment of the feed composition may be controlled in order to obtain an intermediate carbohydrate composition having a ratio of DP5/DP2s in the range of about 0.401.0, such as about 0.40-0.90, such as about 0.40-0.85 or about 0.45-0.75; and a ratio of DP3-5/DP2s in the range of about 1.0-2.5, such as about 1.1-2.4, or about 1.15-2.25.
- the treatment of the feed composition may be controlled in order to obtain an intermediate carbohydrate composition having a ratio of DP5/DP1+2 up to about 0.60, such as about 0.10-0.50, about 0.10-0.45, or about 0.15-0.40; and a ratio of DP3-5/DP1+2 in the range of about 0.25-1.50, such as about 0.50-1.30.
- the treatment of the feed composition may be controlled to produce an intermediate carbohydrate composition comprising, on a dry weight basis, greater than about 40% DP3+, such as about 44-75% DP3+; and less than about 15% DP16+, such as about 1-14% DP16+.
- the treatment of the feed composition may be controlled to produce an intermediate carbohydrate composition comprising, on a dry weight basis less than about 15% DP16+, such as less than about 7%, such as less than about 3%, and such as less than about 1% DP16+.
- the desired molecular weight distribution of lower digestible oligosaccharides and polysaccharides can be achieved by controlling parameters in the processes according to the disclosure, such as, for example, time, temperature, type and concentration of saccharide, type and concentration of catalyst, ratio of the saccharide to catalyst, concentrations of cationic and anionic compounds (e.g., minerals), pH, pressure, and water concentration.
- parameters in the processes according to the disclosure such as, for example, time, temperature, type and concentration of saccharide, type and concentration of catalyst, ratio of the saccharide to catalyst, concentrations of cationic and anionic compounds (e.g., minerals), pH, pressure, and water concentration.
- the progress of the treatment step in producing an intermediate composition having a particular molecular weight distribution of oligosaccharides and polysaccharides may be monitored by in-process analytical methods, for example in-line and/or off-line chromatography (e.g. HPLC), or infrared spectroscopy (e.g. FTNIR) that provide data regarding the content of the intermediate composition.
- in-process analytical methods for example in-line and/or off-line chromatography (e.g. HPLC), or infrared spectroscopy (e.g. FTNIR) that provide data regarding the content of the intermediate composition.
- the progress of the treatment step may be monitored by monitoring the viscosity of the reaction mixture during the treatment process, and terminating the process when a pre-determined viscosity is reached.
- the viscosity of the composition inside the treatment vessel will be sensitive to the amount of oligosaccharides and polysaccharides produced (i.e., DP3+), with viscosity increasing as the amount of
- oligosaccharides and polysaccharides increase.
- Those skilled in the art can use any technique known to those of skill in the art to monitor viscosity during the treatment, including but not limited to monitoring motor amps from a vessel agitator, monitoring motor amps on a recirculation pump, and using in-line viscometers.
- one of skill in the art may monitor the progress of the treatment step (such as by the methods described above) and then correlate those results with treatment time as a function of other treatment step parameters (e.g., the saccharide used, temperature, catalyst level).
- other treatment step parameters e.g., the saccharide used, temperature, catalyst level.
- the process to obtain the intermediate composition described herein limits the formation of high levels of higher oligosaccharides and polysaccharides, and thus surprisingly enables the final carbohydrate composition with desirable physical and functional properties of the present disclosure.
- the controlled treatment of the feed composition also limits the formation of color and off-flavor in the intermediate composition, thus contributing to the lighter color and less off-flavor of the final carbohydrate compositions according to the present disclosure relative to commercially available reduced- sugar, reduced-calorie ingredients such as Litesse ® polydextrose and Promitor TM soluble corn fiber.
- the treatment process may comprise steps of providing a saccharide feedstock having a desired %DS, and adding a catalyst to produce a feed composition. Further steps of providing the feed composition into a reaction vessel and then applying vaccuum pressure and heating for a period of time, until a desired viscosity is reached. It should be noted, however, that one or more step of the treatment process may be omitted, or additional steps may be added, according to various exemplary embodiments.
- the treatment process may begin with a feed composition wherein the feedstock and catalyst are already mixed; a step of applying vaccuum pressure may be omitted; or a conventional evaporation step may be added.
- a feed composition may be prepared by adding concentrated sulfuric acid or hydrochloric acid to a feedstock chosen from 95% dextrose having
- composition may then be added to a reaction vessel and heated under 20 inches Hg vacuum to a temperature ranging from about 120-180°C for about 20-60 minutes.
- a feed composition may be prepared by adding concentrated sulfuric acid to a feedstock chosen from 95% dextrose having 65% DS, in an amount sufficient to produce a concentration of 200 ppm.
- the feed composition may then be added to a reaction vessel and heated under 20 inches Hg vacuum to a temperature ranging from about 132-144°C for about 20 minutes, after which the vaccuum may be broken and the heating continued for an additionnal 15-45 minutes under atmopheric pressure.
- a feed composition may be prepared by adding concentrated sulfuric acid to a feedstock chosen from 95% dextrose having 71% DS, in an amount sufficient to produce a concentration of 200 ppm.
- the feed composition may then be provided to an evaporator and any conventional evaporation technique used for a period of time sufficient to produce a composition having about 80-90% DS, after which the composition may be heated, optionally under 20 inches Hg vacuum, to a temperature ranging from about 120- 180°C for about 20-60 minutes.
- any combination of heating temperatures and times may be chosen to prepare an intermediate carbohydrate composition according to various embodiments of the disclosure, so long as the intermediate composition prepared comprises the desired
- the feed composition may be heated to a temperature range of about 50 to 350°C or about 50 to 250°C, such as, for example, about 80 to 210°C, about 90 to 180°C, about 100 to 180°C, about 110 to 180° C, about 120 to 180°C, about 125 to 140°C, about 125 to 135°C, about 125 to 130°C, about 130 to 140°C, about 130 to 135°C, about 135 to 140°C, or about 100 to 200°C.
- the saccharide may be heated with a catalyst to a temperature range of about 120°C to about 180°C, such as about 140°C to about 170°C, or about 143°C to about 166°C, such as about 155°C.
- the feed composition may be desireable to heat the feed composition to one temperature for one period of time, and then to a second, different temperature, for a second period of time, and so on for any number of periods of time.
- the feed composition may be heated to about the specified temperature or temperature range for the entire treatment time.
- the treatment time can range from about 5 seconds to about 5 days, depending on how the parameters cited herein are controlled.
- the treatment time can range up to about 24 hours, such as up to about 12 hours, up to about 6 hours, or up to about 2 hours.
- the treatment time can range from about 15 minutes to about 2 hours, such as about 30 minutes to about 2 hours, about 30 minutes to about 1 hour, about 20 minutes to about an hour, or about 15 minutes to about 1 hour.
- the treatment time can range from about 20 to about 30 minutes, about 30 to about 50 minutes, or about 45 to about 60 minutes. From a commercial production standpoint, it may be preferable to minimize treatment time thus keeping production of the carbohydrate compositions of the present disclosure more economical.
- the feedstock may be chosen from at least one saccharide, in any form, such as, for example, solid form or as an aqueous solution.
- the concentration of DS can range up to about 99%, such as, for example, up to about 95%, up to about 90%, up to about 85%, up to about 80%, up to about 75%, up to about 70%, or up to about 65%.
- the concentration of DS can range up to about 99%, such as, for example, up to about 95%, up to about 90%, up to about 85%, up to about 80%, up to about 75%, up to about 70%, or up to about 65%.
- the concentration of DS can range up to about 99%, such as, for example, up to about 95%, up to about 90%, up to about 85%, up to about 80%, up to about 75%, up to about 70%, or up to about 65%.
- the concentration of DS can range up to about 99%, such as, for example, up to about 95%, up to about 90%, up
- concentration of DS may range from about 30% to about 95%, such as about 35% to about 95%, about 35% to about 90%, about 40% to about 90%, or about 45% to about 90%. In yet further exemplary embodiments, the concentration of DS may range from about 25 to 75%, such as about 35 to 65%, or about 30 to 71%. In yet a further exemplary embodiment, the concentration of DS of the feedstock may range from at least 65%, such as about 65 to 75%.
- the concentration of DS may be about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, or about 95%, with the understanding that each of these numbers may represent an endpoint for either a low-end or high-end of any subrange between about 5% and about 95%.
- the concentration of DS may range from at least 65%, such as at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, or at least 95%.
- the concentration of DS in the feedstock may range from about 70% to about 95%, such as about 80% to about 90%.
- Exemplary saccharides for use as a starting material include, but are not limited to, a monosaccharide, a disaccharide, an oligosaccharide, and other starch hydrolysates (i.e., derived from the hydrolysis of starch), for example and without limitation, a glucose syrup, a corn syrup, and mixtures thereof.
- starting materials may be chosen from any and all ranges of dextrose equivalent syrups may be chosen as a starting material.
- starting materials may be chosen from 20-99DE syrups.
- a preferred exemplary embodiment of the starting material is dextrose or a dextrose syrup.
- the saccharide may be chosen from 95% dextrose corn syrup.
- a saccharide can also be combined with a polyol, such as and without limitation, sorbitol, glycerol, erthritol, xylitol, mannitol, and galactitol, and mixtures thereof.
- a polyol such as and without limitation, sorbitol, glycerol, erthritol, xylitol, mannitol, and galactitol, and mixtures thereof.
- the polyol may be incorporated into the low digestibility oligosaccharides and polysaccharides of the intermediate composition.
- the saccharide for the feedstock may also be chosen from any mixture of saccharides.
- there may be small amount of other components present in the saccharide starting materials such as, for example, proteins, ash, fat, vitamins, and minerals. However, any additional component that does not substantially interfere with the process may be present in the starting material.
- the at least one catalyst may be chosen from any alkaline or acidic catalyst, catalytic resin, metal catalyst, and any activated catalytic media.
- the catalyst is not an enzyme.
- acidic catalysts useful according to various embodiments of the disclosure include organic acids and anhydrides thereof, and inorganic acids.
- the acid catalysts can be homogeneous acid catalysts or heterogeneous acid catalysts.
- Organic acids useful according to various embodiments of the disclosure include, but are not limited to, adipic acid, acetic acid, citric acid, fumaric acid, gluconic acid, itaconic acid, lactic acid, maleic acid, malic acid, succinic acid, tartaric acids, terephthalic acids, and mixtures thereof.
- the catalyst when the catalyst is chosen from organic acids, the catalyst may be present in an amount ranging from about 0.01% to about 5% by weight, such as about 0.1% to about 3% by weight, about 0.5% to about 2%, or about 1% to about 1.5%.
- Inorganic acids useful according to various embodiments of the disclosure include, but are not limited to, hydrochloric acid, sulfuric acid, sulfurous acid, thiosulfuric acid, dithionic acid, pyrosulfuric acid, selenic acid, selenious acid, nitric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, pyrophosphoric acid, polyphosphoric acid, hypophosphoric acid, boric acid, perchloric acid, hypochlorous acid, hydrobromic acid, hydriodic acid and silicic acid, acidic alkali metal or alkaline earth metal salts of the above inorganic acids, and mixtures thereof.
- the catalyst may be chosen from sulfuric acid and hydrochloric acid.
- the catalyst when the catalyst is chosen from inorganic acids, the catalyst may be added to produce a concentration ranging up to about 1250 ppm, such as up to about 1000 ppm, up to about 750 ppm, up to about 500 ppm, or up to about 250 ppm.
- the inorganic acids may be present in an amount to produce a concentration in the range of about 20 to about 1000 ppm, or about 30 to about 500 ppm.
- catalytic resins metal catalysts, and any type of activated catalytic media
- one of skill in the art will be able to choose the appropriate type of catalytic media and method, such as, for example, a column packed with activated carbon, through which the saccharide feedstock may be pumped.
- the saccharide feedstock which may have a pH in the range of about 3.0 to about 6.0, may be treated with at least one inorganic acid, at least one organic acid, or mixtures thereof, in an amount sufficient to adjust the pH of the feed composition to a desired pH or pH range. It is within the ability of those skilled in the art to determine how much of any particular acid to add to the composition, in order to achieve the desired pH.
- the pH of the feed composition may, in various exemplary embodiments, be within a range of up to about 4.0, such as, up to about 3.0, or up to about 2.0, such as for example, about 1.2-1.9, about 1.2-1.6, or about 1.5-1.9.
- the pH of the feed composition may be about 1.0, about 1.1, about 1.2, about 1.3, about 1.4, about 1.5, about 1.6, about 1.7, about 1.8, about 1.9, about 2.0, about 2.1, about 2.2, about 2.3, about 2.4, about 2.5, about 2.6, about 2.7, about 2.8, about 2.9, about 3.0.
- the pH of the feed composition ranges from about 1.0 to about 2.5.
- At least one oxidizing agent may also be present in the feed composition.
- Oxidizing agents useful according to various embodiments of the disclosure include, but are not limited to, peroxides and peroxy acids.
- the oxidizing agent may be chosen from hydrogen peroxide, oganic peroxyacids, such as peracetic acid, performic acid and inorganic peroxyacids, such as peroxysulfutic acid.
- the oxidizing agent may be added in any amount.
- a further, optional step in the treatment process for preparing an intermediate carbohydrate composition according to the disclosure comprises treating the feed composition by subjecting the composition to reduced pressure, by any method known, such as, for example, by vaccum.
- the reduced pressure such as vacuum
- the reduced pressure that the composition may be subjected to may range up to about 29 inch Hg vacuum, such as, for example, up to about 26.5 inch Hg vacuum.
- the reduced pressure may range from about 5-29 inch Hg vacuum, such as about 10-26 inch Hg vacuum or about 15-26.5 inch Hg vacuum.
- the reduced pressure may be in the range of about 18 to about 22 inch Hg vacuum, such as about 20 inch Hg vacuum.
- the step of subjecting the composition to reduced pressure may be carried out alone or in any combination with any of the other steps described for the treatment process.
- the saccharide feedstock may be combined with the at least one catalyst either sequentially or simultaneously with other processing parameters of the treatment step.
- a saccharide may be treated with heat and/or pressure and subsequently contacted with a catalyst.
- an aqueous saccharide composition may be treated with at least one acid, and either simultaneously or subsequently treating the aqueous feed composition with heat and/or reduced pressure.
- an aqueous saccharide composition may be treated with at least one organic acid and at least one oxidizing agent, and either simultaneously or subsequently treated with heat and/or reduced pressure.
- an aqueous saccharide feedstock may be treated by adjusting the pH of the aqueous feedstock and then the pH-adjusted composition may have both at least one oxidizing agent and at least one organic acid added in a further treatment step, and either simultaneously or subsequently treated with heat and/or reduced pressure.
- a saccharide and a catalyst may be pre -blended and then simultaneously treated with heat and/or reduced pressure.
- water such as deionized water
- water may be added in any amount. It may, in certain embodiments, be desireable to add an amount of water sufficient to produce an intermediate composition comprising about 5-85% DS, such as about 25-80% DS, about 40-80% DS, about 25-70%, about 40-60%, or about 50-60% DS, the concentration depending on the selected separation step, as discussed below.
- an amount of water sufficient to prepare an intermediate composition comprising about about 30%, 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, or about 80% DS may be added.
- the intermediate composition may comprise about 60% DS.
- the solution containing the intermediate composition is then separated by any known separation process to produce at least two carbohydrate composition streams.
- a first stream is rich in DP 1+2, relative to a second stream comprising the carbohydrate composition of the current disclosure.
- the streams may be separated in order to produce a first stream comprising a carbohydrate composition comprising from about 30 to about 100%, such as from about 40 to about 100%, from about 50 to about 100%, or from about 60 to about 100%, DP1+2 on a dry weight basis, and a second stream comprising less than about 30%, such as less than about 25% DP1+2 on a dry weight basis, such as less than about 20%; an amount of DP3-5 in the range of from about 20 to about 50%, such as from about 23 to about 45%, from about 30 to about 40%, or from about 35 to about 37%, such as about 36%, on a dry weight basis; an amount of DP6+ in the range of from about 35% to about 71%, such as from about 36% to about 65%, or from about 40% to about 65%, such as about 40% to about 60%, on a dry weight basis; an amount of DP11+ less than about 40% or less than about 38%, such as in the range of from about 5% to about 38%, such as from
- the separation process can be accomplished by any known method, such as, for example, chromatographic fractionation, membrane filtration, nanofiltration, dialysis, preferential precipitation using solvents, etc., as well as any combination of these methods. It is within the ability of those skilled in the art to choose the appropriate separation method to obtain the first and second streams according to various embodiments of the disclosure.
- the separation process is controlled to remove (via a first stream) certain amounts of DPI and DP2, and optionally additional oligosaccharides, from the solution comprising the intermediate composition, so that a resulting second stream contains a reduced- sugar, lower-digestibility carbohydrate composition with the intended physical and functional properties.
- the first stream may optionally be recycled to the vessel containing the feed composition, and further subjected to the treatment process in order to produce more of the intermediate composition as described above.
- the solution containing the intermediate composition may then be subjected to a biological treatment, such as, for example yeast fermentation, that utilizes DPI and DP2 components in the intermediate composition, resulting in a stream that contains a reduced-sugar, lower-digestibility carbohydrate composition with the intended physical and functional properties.
- a biological treatment such as, for example yeast fermentation
- the second stream comprises a carbohydrate composition which exhibits reduced sugar content and lower digestibility relative to traditional nutritive sweeteners, such as, for example sucrose, high fructose corn syrup, and corn syrup.
- traditional nutritive sweeteners such as, for example sucrose, high fructose corn syrup, and corn syrup.
- the carbohydrate compositions may, according to various embodiments, comprise an amount of DP1+2 of less than about 30%, such as, for example, less than about 25%, less than about 20%, or less than about 15%. In at least one preferred embodiment, the amount of DP1+2 in the carbohydrate composition ranges from about 5% to about 15%.
- the carbohydrate composition may, according to various embodiments, comprise an amount of total DP3-5 greater than about 20%, such as, for example, greater than about 25%, greater than about 30%, greater than about 35%, greater than about 40%, or greater than about 45%.
- the amount of DP3-5 ranges from about 20% to about 50%.
- the carbohydrate composition may comprise an amount of DP3-4 in an amount up to about 25%, such as up to about 22%, for example in the range of about 8% to about 25%, or about 10% to about 22%.
- the amount of DP3-6 ranges from about 25% to about 60%, such as about 30% to about 55%.
- the carbohydrate compositions prepared according to the disclosure may comprise a ratio of (DP3-5)/DP6+ greater than about 0.25, such as, for example, greater than about 0.3, greater than about 0.4, greater than about 0.5, greater than about 0.6, greater than about 0.7, greater than about 0.8, greater than about 0.9, greater than about 1.0, greater than about 1.1, greater than about 1.2, greater than about 1.3, or greater than about 1.4.
- the ratio of (DP3-5)/DP6+ is in the range of about 0.3 to about 1.5.
- the carbohydrate compositions may comprise a ratio of (DP3-4)/DP6+ greater than about 0.1, such as greater than about 0.2, greater than about 0.3, greater than about 0.4, greater than about 0.5, for example about 0.1 to about 0.75, or about 0.15 to about 0.70.
- the carbohydrate compositions may comprise a ratio of (DP3-6)/DP6+ greater than about 0.5, such as greater than about 0.6, greater than about 0.7, greater than about 0.8, greater than about 0.9, greater than about 1.0, greater than about 1.1, greater than about 1.2, or greater than about 1.3, for example about 0.5 to about 1.4.
- the carbohydrate compositions according to the disclosure have a surprisingly lower PDI.
- the PDI of the disclosed carbohydrate compositions is generally less than about 2, such as less than about 1.95, less than about 1.90, less than about 1.85, less than about 1.80, less than about 1.75, less than about 1.70, less than about 1.65, less than about 1.60, less than about 1.55, less than about 1.50, less than about 1.45, less than about 1.40, less than about 1.35, less than about 1.30, less than about 1.25, or less than about 1.20.
- the PDI of the carbohydrate compositions may range from about 1.0 to about 2.0, such as about 1.1 to about 1.9, about 1.1 to about 1.8, about 1.2 to about 1.8, about 1.3 to about 1.8, or about 1.4 to about 1.8.
- PDI in combination with a lower mass average and lower number average molecular weight, relative to reduced- sugar, reduced-calorie carbohydrates such as Litesse ® polydextrose and
- Promitor soluble corn fiber provides carbohydrate compositions having a surprisingly reduced viscosity relative to low DE corn syrups (e.g. 25 DE and 28 DE).
- the carbohydrate compositions have a surprisingly reduced viscosity relative to commercially available reduced-sugar, reduced- calorie ingredients such as Litesse ® polydextrose and Promitor TM soluble corn fiber.
- the carbohydrate composition may comprise a combination of a PDI less than about 2, such as less than about 1.95, less than about 1.9, less than about 1.85, or less than about 1.8, such as from about 1.3 to about 1.8; a M w of less than about 2000, such as less than about 1900, less than about 1800, less than about 1700 less than about 1600, less than about 1500, less than about 1400, or less than about 1300, such as from about 500 to about 2000 or about 900 to about 1700; and a M n of less than about 1200, such as less than about 1150, less than about 1100, less than about 1050, less than about 1000, less than about 950, less than about 900, less than about 850, less than about 800, less than about 750, less than about 700, or less than about 650, such as from about 600 to about 1150; as well as any and all combinations of PDI, M w , and M n thereof.
- the carbohydrate compositions may comprise a PDI ranging from about 1.3 to about 1.8; a M w ranging from about 900 to about 1700; and a M n ranging from about 600 to about 1150.
- the carbohydrate compositions may comprise a PDI of about 1.5; a M w of about 1650; and a M n of about 1150.
- the carbohydrate compositions may comprise a PDI of about 1.4; a M w of about 1050; and a M n of about 750.
- the carbohydrate compositions prepared according to the disclosure may comprise branched saccharides with a- and/or ⁇ -glycosidic bonds at various carbon positions, such as a 1,6-; 1,4-; 1,2-; 1,3-; and 4,6-glycosidic linkages.
- the carbohydrate compositions prepared according to the disclosure have a glycosidic linkage profile similar to that of polydextrose, but with less than 10% sorbitol.
- the carbohydrate compositions may comprise less than 5% sorbitol, such as less than 1% sorbitol, substantially no sorbitol, or no sorbitol.
- the carbohydrate composition prepared according to the disclosure may comprise: 1,6-glycosidic linkages in an amount of greater than about 10%, such as greater than about 15%, for example about 10% to about 25% or about 15% to about 25%; 1,4-glycosidic linkages in an amount of less than about 30%, such as less than about 20%, such as less than about 10%; 1,2-glycosidic linkages in an amount up to about 10%, such as up to about 8%, for example from about 5% to about 7%; 1,3-glycosidic linkages in an amount up to about 10%, such as up to about 8%, for example from about 5% to about 8%, for example about 7%; and 4,6-glycosidic linkages in an amount up to about 5%, such as up to about 4%, such as, for example, about 2% to about 4%, or about 2.5% to about 3.5%.
- the carbohydrate compositions prepared according to the disclosure may comprise a ratio of l,6-/l,4-glycosidic linkages of greater than about 0.4, such as greater than about 0.5, such as greater than about 0.6, for example from about
- 0.5 to about 4.0 such as about 1.0 to about 4.0, about 1.0 to about 3.0 or about 2.0 to about 2.5, for example about 2.1; a ratio of l,6-/4,6-glycosidic linkages of greater than 1.0, such as greater than 2.0, greater than 3.0, greater than 4.0, greater than 4.5, greater than 4.6, such as about 4.5 to about 8; a ratio of l,4-/l,2-glycosidic linkages of less than 8.0, such as less than 7.0, less than 6.0, less than 5.0, or less than 4.0, for example less than 3.9, less than about 3.8, or less than about 3.5, such as less than about 3.0, such as less than about 2.0, or about 1.0 to about 3.0, or about 1.0 to about 4.0; and a ratio of l,4-/l,3-glycosidic linkages of less than about 6.0, such as less than about 5.0, less than about 4.0, less than about 3.0, such as less
- the carbohydrate compositions prepared according to the disclosure may comprise a ratio of (1,6- +l,4-)/l,2-glycosidic linkages of less than 6.4, such as less than about 6.0, such as less than about 5.5, such as less than about 5.0, such as about 4.0 to about 5.0, or 3.7 to 6.3; and a ratio of (1,6- +l,4-)/l,3-glycosidic linkages of less than 4.7, such as less than about 4.5, such as less than about 4.0, such as 3.2 to about 4.6, for example about 3.5.
- the carbohydrate composition of this disclosure may comprise a total sum of 1,6- and 1,4-glycosidic linkages less than about 35%, such as less than about 30%, for example ranging from about 20% to about 30%, such as about 23% to about 27%, for example about 25%.
- the carbohydrates and carbohydrate compositions according to the disclosure may have reduced-calorie content.
- reduced calorie content By “reduced calorie content”, “reduced calorie”, and variations thereof, which may be used interchangeably herein, it is intended that the carbohydrate composition has a lower calorie content, respectively, relative to either (1) the starting material (i.e., saccharide feedstock), or (2) traditional starch- derived carbohydrate compositions, or (3) other nutritive carbohydrates such as sucrose (or “table sugar"), maltose, lactose, glucose, galactose and fructose. At least in part, the reduced calorie content is believed to be due to the lower-digestibility of the carbohydrate compositions as well as the reduced sugar content, as described above.
- the carbohydrate compositions disclosed herein may have a calorie content that is up to about 100% lower than either the starting material or traditional forms of the component or product.
- the calorie content may be up to about 95% lower, such as up to about 90% lower, up to about 85% lower, up to about
- carbohydrate compositions made according to various embodiments of the disclosure may have about a 25-75% reduced calorie content, such as, for example, about a 40-75% or about a 40-50% reduced calorie content, relative to current traditional corn syrups and current traditional nutritive sweeteners.
- the carbohydrate compositions may have caloric values of less than about 4 kcal/g, such as less than about 3.5 kcal/g, such as less than about 3 kcal/g, such as less than about 2.5 kcal/g, such as less than about 2 kcal/g, such as less than about 1.5 kcal/g, or less than about 1 kcal/g, calculated on a dry weight basis and when ingested by a human or other mammal.
- the carbohydrate compositions may have caloric values ranging from about 1 to about 3 kcal/g.
- the terms “low-digestibility”, “lower-digestibility”, and variations thereof, which may be used interchangeably herein, are meant to indicate that the carbohydrate composition of the present disclosure has a lower degree of digestibility relative to either (1) the starting material (i.e., saccharide feedstock), or (2) traditional starch-derived carbohydrate compositions, or (3) other traditional nutritive sweeteners such as sucrose (or “table sugar"), maltose, lactose, glucose, galactose and fructose.
- the lower digestibility may be due, in part, to some amount of the carbohydrate being non-digestible or substantially non-digestible, as described above.
- the carbohydrate compositions may have a digestibility that is up to about 100% lower than either the starting material or traditional forms of the component or product.
- the digestibility may be up to about 95% lower, such as up to about 90% lower, up to about 85% lower, up to about 80% lower, up to about 75% lower, up to about 70% lower, up to about 65% lower, up to about 60% lower, up to about 55% lower, up to about 50% lower, up to about 45% lower, up to about 40% lower, up to about 35% lower, up to about 30% lower, up to about 25% lower, up to about 20% lower, up to about 15% lower, up to about 10% lower, or up to about 5% lower, with the understanding that each of these numbers may represent an endpoint for either a low-end or high-end of any subrange between about 5% and about 95%.
- digestibility may be in the range of about 5-50%, such as about 5-35%, about 5-30%, about 10-30%, or about 20-30%.
- carbohydrate compositions disclosed herein have a digestibility that is less than 100%, i.e. that is not completely digestible or that there is some percentage that is not digestible.
- the carbohydrates, carbohydrate compositions, and products disclosed herein may have a digestibility of less than about 95% (i.e. about 5% is not digestible), such as less than about 90% (i.e. about 10% is not digestible), less than about 85% (i.e.
- about 15% is not digestible
- less than about 80% i.e. that about 20% is not digestible
- less than about 75% i.e. that about 25% is not digestible
- less than about 70% i.e. that about 30% is not digestible
- less than about 65% i.e., that about 35% is not digestible
- less than about 60% i.e. about 40% is not digestible
- less than about 55% i.e. about 45% is not digestible
- less than about 50% i.e. that about 50% is not digestible
- less than about 45% i.e. that about 55% is not digestible
- less than about 40% i.e.
- the carbohydrate compositions have a digestibility ranging from about 5% to about 95%, such as about 5% to about 75%, about 5% to about 50%, or about 5% to about 35%.
- reduced sugar content is meant to indicate that the carbohydrate composition has a lower sugar content relative to either (1) the starting material (i.e., the saccharide feedstock), or (2) traditional starch-derived carbohydrate compositions, or (3) other nutritive carbohydrates such as sucrose (or “table sugar"), maltose, lactose, glucose, galactose and fructose.
- the carbohydrate compositions disclosed herein may have a sugar content that is up to about 100% lower than either the starting material or traditional forms of the component or product.
- the sugar content may be up to about 95% lower, such as up to about 90% lower, up to about 85% lower, up to about 80% lower, up to about 75% lower, up to about 70% lower, up to about 65% lower, up to about 60% lower, up to about 55% lower, up to about 50% lower, up to about 45% lower, up to about 40% lower, up to about 35% lower, up to about 30% lower, up to about 25% lower, up to about 20% lower, up to about 15% lower, up to about 10% lower, or up to about 5% lower, with the understanding that each of these numbers may represent an endpoint for either a low-end or high-end of any subrange between about 5% and about 95%.
- carbohydrate compositions made according to various embodiments of the disclosure may have about a 20-75% reduced sugar content, such as, for example, about a 25-75% or about a 25-50% reduced sugar content, relative to traditional corn syrups having similar viscosities.
- Carbohydrate compositions according to various embodiments of the disclosure may, in various embodiments, exhibit physical properties similar to that of traditional starch- derived carbohydrate compositions, such as, for example, concentration of dry solids, viscosity, color, and/or pH. However, in at least some exemplary embodiments, one or more of these physical properties may be different.
- the viscosities of the carbohydrate compositions of the present disclosure are surprisingly reduced compared to low DE corn syrups (e.g., 25 DE and 28 DE) as well as compared to commercially available reduced-sugar, reduced-calorie ingredients such as Litesse ® polydextrose and Promitor TM soluble corn fiber.
- the carbohydrate compositions have a viscosity less than 6,000 cPs, such as less than 5,800, less than 5,500 cPs, less than 5,000 cPs, less than 4,500 cPs, less than 4,000 cPs, less than 3,500 cPs, less than 3,000 cPs, less than 2,500 cPs, less than 2,000 cPs, less than 1,500 cPs, less than 1000 cPs, or less than 500 cPs, at about 75% DS and about 38° C.
- the carbohydrate compositions have a viscosity ranging from about 2000 cPs to about 6000 cPs, such as about 2500 to about 4500 cPs, at 75%DS and 38°C.
- the color of the inventive carbohydrate compositions may be comparable to that of traditional starch-derived carbohydrate compositions.
- a lighter-colored product may be desirable in certain applications. Color is determined by the following method:
- the inventive carbohydrate composition may have CIRF values of less than about 10, less than about 8, less than about 5, less than about 4, less than about 3, less than about 2, or less than about 1, measured at 50% DS.
- the carbohydrate compositions according to the disclosure have a CIRF value of less than 2, about 1 to about 8, such as about 1 to about 2, or greater than 1 to about 8, such as greater than 1 to less than 2 or ranging from 1 to 2.
- Conventional corn syrups have a CIRF of less than 1.
- reduced-sugar reduced-calorie ingreidents such as Litesse ® polydextrose, Promitor TM soluble corn fiber, resistant dextrin and resistant maltodextrin, have a CIRF value of greater than 6 measured at 50% DS.
- the carbohydrate compositions produced according to various embodiments of the disclosure comprise saccharide molecules comprising greater than 90% glucose, less than about 30% DP1+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000 daltons, a PDI ranging up to about 2.0,greater than about 15% 1,6-glycosidic linkages, a ratio of l,6-glycosidic/l,4-glycosidic linkages of greater than about 0.6, less than about 35% total 1,6-glycosidic and 1,4-glycidic linkages, and, a digestibility ranging from about 5 to about 50%.
- the carbohydrate compositions produced according to various embodiments of the disclosure comprise saccharide molecules comprising greater than 90% glucose, less than about 25% DP1+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000 daltons, a PDI ranging from about 1.1 to about 1.8,from about 15% to about 19% 1,6-glycosidic linkages, a ratio of l,6-glycosidic/l,4-glycosidic linkages ranging from about 0.7 to about 4.0, less than about 30% total 1,6-glycosidic and 1,4-glycidic linkages, and, a digestibility ranging from about 5 to about 35%.
- the carbohydrate compositions may comprise 1,4- glycosidic linkages in an amount less than about 20%, and/or a ratio of l,4-glycosidic/4,6- glycosidic linkages greater than about 4.0.
- the carbohydrate compositions may have a CIRF value of less than about 8.0.
- the carbohydrate composition may have a caloric value of less than 4 kcal/gram and/or a reduced calorie content in the range of about 25% to about 75%.
- the viscosity of the carbohydrate compositions is less than about 6000 cPs at about 75% DS and about 38°C.
- carbohydrate compositions prepared according to the disclosure comprise saccharide molecules comprising greater than 90% glucose, less than about 30% DP1+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000 daltons, a polydispersity index ranging up to about 2.0, greater than about 10% 1,6-glycosidic linkages, a ratio of 1,6- glycosidic/l,4-glycosidic linkages of greater than about 0.5, less than about 35% total 1,6- glycosidic and 1,4-glycidic linkages, and a digestibility ranging from about 5 to about 50%.
- compositions prepared according to the disclosure comprise saccharide molecules comprising greater than 90% glucose, less than about 30% DPl+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000 daltons, a polydispersity index ranging up to about 2.0, a total amount of DP3-5 greater than about 20%, a ratio of (DP3-5)/DP6+ greater than about 0.25, and a digestibility ranging from about 5 to about 50%.
- Yet further exemplary emodiments of the carbohydrate compositions prepared according to the disclosure comprise saccharide molecules comprising greater than 90% glucose, less than about 30% DPl+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000 daltons, a polydispersity index ranging up to about 2.0, a total amount of DP3-5 greater than about 20%, greater than about 10% 1,6-glycosidic linkage, a ratio of l,6-glycosidic/l,4-glycosidic linkages of greater than about 0.5, and a digestibility ranging from about 5 to about 50%.
- One exemplary embodiment comprises a treatment step comprising subjecting a feed composition comprised of a saccharide feedstock and at least one catalyst to elevated temperature, wherein said treatment step produces an intermediate composition comprising an amount of DPl+2, on a dry weight basis, ranging from about 10% to about 85%, an amount of DP3+, on a dry weight basis, ranging from about 40% to about 80%, a ratio of DP5/DP2s ranging from about 0.4 to about 1.0, an amount of DP16+, on a dry weight basis, of less than about 15%, a polydispersity index ranging from about 1.2 to about 3.5, a weight average molecular weight ranging from about 300-3200 daltons, and a viscosity ranging from about 300 cPs to about 8000 cPs, measured at 75%DS and 38°C.
- Further embodiments comprise a separation step comprising separating an intermediate composition, optionally prepared as described, into at least two streams, wherein at least one first stream comprises about 30% to about 100% DPl+2, and wherein at least one second stream comprises less than about 30% DPl+2.
- Additional embodiments according to the disclosure relate to foodstuffs or products chosen from food or beverage products or nutritional supplements, said foodstuff or product comprising a carbohydrate composition comprising saccharide molecules comprising greater than 90% glucose, less than about 30% DP1+2, on a dry weight basis, a weight average molecular weight ranging from about 500 to about 2000 daltons, a polydispersity index ranging up to about 2.0, greater than about 10% 1,6-glycosidic linkages, a ratio of l,6-glycosidic/l,4- glycosidic linkages of greater than about 0.5, less than about 35% total 1,6-glycosidic and 1,4- glycidic linkages, and a digestibility ranging from about 5 to about 50%.
- Yet further embodiments according to the disclosure relate to foodstuffs or products chosen from food or beverage products or nutritional supplements, said foodstuff or product comprising a carbohydrate composition comprising saccharide molecules comprising greater than 90% glucose, less than about 30% DP1+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000 daltons, a polydispersity index ranging up to about 2.0, a total amount of DP3-5 greater than about 20%, greater than about 10% 1,6-glycosidic linkage, a ratio of l,6-glycosidic/l,4-glycosidic linkages of greater than about 0.5, and a digestibility ranging from about 5 to about 50%.
- a carbohydrate composition comprising saccharide molecules comprising greater than 90% glucose, less than about 30% DP1+2, on a dry weight basis, a weight average molecular weight ranging up to about 2000 daltons, such as from about 500 to about 2000
- one or more of the feedstock, the feed composition, the intermediate composition, and the final carbohydrate composition do not comprise sorbitol.
- the carbohydrate composition contains substantially no sorbitol.
- the carbohydrate composition is not a mixture of 90:10 glucose: sorbitol.
- the carbohydrate composition comprises saccharide molecules comprising greater than 90% glucose, and comprising less than 10% sorbitol.
- the carbohydrate composition may comprise less than 9.5%, less than 9.0%, less than 8.5%, less than 8.0%, less than 7.5%, less than 7.0%, less than 6.5%, less than 6.0%, less than 5.5%, less than 5.0%, less than 4.5%, less than 4.0%, less than 3.5%, less than 3.0%, less than 2.5%, less than 2.0%, less than 1.5%, less than 1.0%, or less than 0.5% sorbitol, according to various exemplary embodiments.
- the carbohydrate compositions prepared according to various embodiments of the disclosure may optionally be refined, e.g. using filters, centrifuges, granular activated carbons or ion-exchange resins, and excess water can be removed by evaporation or other methods known to those skilled in the art.
- the carbohydrate compositions may thus be in any form, such as, for example, in syrup form, liquid form(e.g. aqueous), or dry form.
- Products according to various embodiments of the disclosure may have lower digestibility and/or reduced sugar, as a result of the incorporation of the carbohydrate compositions having reduced sugar and/or lower-digestibility, as described herein.
- the reduced- sugar, lower-digestible carbohydrate compositions offer properties that are of particular importance to food manufacturing practices and the properties of finished foodstuffs. These important properties include a bland, neutral taste; minimal or no sweetness; compatability with other sweetners; and imparting smooth mouthfeel to finished foods and beverages.
- the inventive carbohydrate compositions can thus be used in any product that typically incorporates traditional starch-derived carbohydrates.
- the carbohydrate compositions according to various embodiments of the disclosure may be particularly suitable in food, beverage, and nutritional supplement applications intended for consumption by both humans and animals.
- uses for the carbohydrate compositions disclosed herein include as bulking, binding and coating ingredients for cereals, bars, confectioneries, beverages and savory products; carriers for coloring agents, flavors, fragrances and essences, and high potency sweeteners; spray drying adjuncts such as for coffee extracts and tea extracts; bulking, bodying and dispersing agents such as in synthetic creams or coffee whiteners; ingredients promoting a moisture retention in bread, pastry and meats; components of dry soup mixes, bakery mixes, frosting mixes, spice mixes and blends, coverage powders, condiments, gravy mixes, sauce mixes and frozen dairy foods, and in fat mimetics.
- they are useful in the formulation of tabletting compounds which can be used in food products or pharmaceutical products, anti-caking agents, whipped products, protective coatings, agglomeration aids, and low- or reduced-calorie foods and
- foodstuffs comprising the carbohydrate compositions described herein have shown properties relative to existing reduced- sugar, reduced-calorie sweeteners, e.g. Litesse ® polydextrose, Nutriose ® resistant dextrin, Fibersol-2 ® resistant maltodextrin, and Promitor soluble corn fiber, that are just as good or are improved.
- Such properties include, but are not limited to, decreased hardness in bars, baked cookies, muffins, and the like; baked cookie spread; baked muffin height and mouthfeel; cookie dough stiffness; and sweetened coatings such as on cereals and the like.
- sweetener in various foodstuffs with some amount of a carbohydrate composition prepared according to the disclosure.
- current sweeteners may be replaced by an amount up to 100%, such as up to 90%, up to 80%, up to 75%, up to 70%, up to 60%, up to 50%, up to 40%, up to 30%, up to 25%, up to 20%, up to 15%, up to 10%, or up to 5%, by carbohydrate compositions according to the disclosure.
- the carbohydrate compositions may be useful as a fiber source.
- the reduced- sugar low-digestibility carbohydrate compositions of this disclosure produced minimal amount of intestinal gas, and thus, the composition is more tolerable to the consumer.
- the amount of a food product that comprises the carbohydrate compositions according to the disclosure as a source of fiber may contain anywhere from about 60-100%, such as about 65-100%, about 70-100%, about 75-100%, about 80-100%, about 85- 100%, about 90-100%, or about 95-100%, by weight of the carbohydrate composition.
- Food products prepared according to various exemplary embodiments according to the disclosure have lower-calorie and/or reduced sugar content, relative to similar products prepared with traditional starch-derived carbohydrate compositions.
- syrups for example corn syrups prepared from corn starch derived feedstocks
- carbohydrates and/or carbohydrate compositions according to the disclosure have lower calorie content and/or reduced sugar content than those prepared with traditional, starch-derived carbohydrates.
- inventive carbohydrate compositions described herein, made according to the processes described, and food products comprising the inventive carbohydrate compositions may have one or more of soluble dietary fiber, reduced sugar, reduced calorie content, and/or lower digestibility
- at least some inventive carbohydrate compositions, made according to the processes described, and food products comprising the inventive carbohydrate compositions may not have one or more of soluble dietary fiber, reduced sugar, reduced calorie content, and/or lower digestibility, yet are still contemplated to be within the scope of the disclosure.
- the starting material of 95% dextrose at about 65% DS having 3% maltose, 0.5% maltotriose, and 1.5% DP3+ on a dry weight basis was used.
- Concentrated sulfuric acid (H 2 SO 4 ) was added to the reaction mixture to achieve a concentration of 30-40 ppm H 2 SO 4 .
- the starting material and acid i.e., the feed composition
- the starting material and acid were pumped into a 22-L horizontal mixer (Model M/DVT-22, LittlefordDay Inc., Florence, Kentucky) equipped with the plow mixing assembly directly driven by a 3-phase, 230 V, 5HP motor and a PowerFlex 70 VFD control panel.
- the mixer was sealed and the plow was turned on at 200rpm (60 Hz).
- About 20 inches of mercury vacuum was applied with a NASH vacuum pump (Model Delta EC50M, Gardner Denver Inc., Wayne, Pennsylvania), and the content was heated for a period ranging from 20 to 60 minutes, to a temperature ranging from 120°C to 180°C by passing steam through the jacket of the mixer to remove moisture during the reaction.
- the power output from the mixing assembly and internal temperature were monitored.
- the power output provided an indirect measure of viscosity in the vessel under various treatment conditions, thus providing an indirect measure of DP16+ levels in the vessel.
- Kw kilowatts
- Enzymatic Digestibility Assay as follows. A 40 mg carbohydrate composition sample was completely dissolved in 3.98 ml of 0.05M citric acid buffer of pH 4.5 in a 10 mL test tube with cap and incubated with 20 ⁇ ⁇ of a glucoamylase and pullulanase enzyme mixture (Optimax
- the carbohydrate composition of the filtered samples was analyzed by HPLC and the net weight percentage of glucose (weight percentage of sample glucose minus weight percentage of the blank glucose) was quantified as percent digestibility of the carbohydrate composition.
- the weight percentage of glucose was obtained by injecting 10 ⁇ ⁇ of the filtered samples to a high performance liquid chromatography (HPLC) system equipped with a refractive index detector and BioRad Aminex HPX-87C column (BioRad, Hercules, California) using water as eluent at a flow rate of 0.70 mL/min and at 85°C for 12 minutes.
- HPLC high performance liquid chromatography
- BioRad Aminex HPX-87C column BioRad, Hercules, California
- the M w , M n , and PDI were determined by size-exclusion chromatography (SEC), a method in which molecules in solution are separated by their size, which correlates well to their molecular weight.
- SEC size-exclusion chromatography
- Polysaccharides (i.e., DP16+) and larger oligosaccharides (e.g., DP11 to DP15) were also determined by this SEC method.
- Pullulan standards with known molecular weights of 5900, 9600, 21100, 47100, 107000, 200000, 344000 and 708000 were purchased from Showa Denko America (New York, New York).
- Glucose, maltose, maltotriose, maltotetraose and maltohexose were purchased from Aldrich Chemicals (St. Louis, Missouri). 1% aqueous standard solutions were prepared by dissolving 0.10 gram of each standard in 10.0 mL of deionized water and then filtered through a 0.45 micron filter. Samples of the
- carbohydrate compositions were first de-ashed with 0.5 g Dowex66 and Dowex 88 mixed resins (Dow Chemical Co., Midland, Michigan) and then diluted with de-ionized water to about 1% followed by filtration through a 0.45 micron filter. 10 ⁇ ⁇ of either the standard solutions or sample solutions were injected into a HPLC system equipped with a Dionex P680 pump, a Shimadzu RID-6A detector, a 08033-TSKgel Guard PWxl guard column and 3 TOSOH
- Bioscience SEC columns (TSK-GEL G4000pwxl, G3000pwxl and G2500pwxl connected in series).
- the chromatography was performed with deionized water as the eluent at a flow rate of 0.5 mL/min at 60°C for 150 minutes.
- the resulting chromatograms were analyzed offline using Polylab SEC software.
- the DP-N composition of a saccharide specifically mono- and di- saccharides
- DPI A and DP1B are understood to be one or more monosaccharides other than glucose, with non-limiting examples including fructose, psicose, lyxose, mannose, galactose, etc., or low-molecular weight degradation products from glucose.
- DP2C is understood to be one or more disaccharides, with non-limiting examples including isomaltose, gentiobiose, cellobiose, trehalose, etc.
- DP2s is the sum of DP2 and DP2C.
- Samples 1-A, 1-B, and 1-C are exemplary embodiments with less than about 1% polysaccharides and greater than 55% DPl+2, and because of the high concentration of DPl+2, they could be heavily recycled in the first stream of the second process step.
- Samples 1-D, 1-E, and 1-F are exemplary embodiments with less than about 10% polysaccharides and less than about 55% DP1+DP2, which could be less heavily recycled in the first stream of the second process step.
- Samples 1-H, 1-1, and 1-J are examples similar to existing reduced- sugar, reduced calorie products with greater than about 15% polysaccharides and less than about 20% DP1+DP2, but with a PDI of greater than 2.
- Intermediate carbohydrate compositions were produced as described in Example 1. These intermediate compositions, designated as 2A and 2B feeds, had about 65% DP3+ (2A feed) or about 70% DP3+ (2B feed), as shown in FIGS. 1 and 3. The 2A and 2B feeds were each dissolved and diluted with de-ionized water to form a solution of about 60% DS.
- the DP3+ enriched streams were sequentially passed through a column packed with granular active carbon (Calgon Carbon Corporation) at about 70°C and a flow rate of about 1 ⁇ 2 bed volume/hour, another column packed with Dowex 66 anionic resin (Dow Chemical), and then another column packed with mixed resins of Dowex 22 and Dowex 88 (Dow Chemical) at about 50°C and a flow rate of about 3 bed volumes/hour.
- the carbon and ion-exchange resin treated solution was evaporated at about 70°C to a final syrup of about 81% DS.
- the final products i.e., carbohydrate compositions according to the present disclosure
- the carbohydrate compositions prepared according to the present disclosure have enriched levels of oligosaccharides of DP3-DP11, particularly enriched in DP3-DP5 and/or DP3-DP6.
- the 2A product has at least 1.5 to 2.1 more DP3-DP5, and/or 2.0 to 2.6 times more DP3-DP6, than the commercially-available reduced-sugar reduced- calorie products.
- the 2A product has at least 3.2 to 4.8 less polysaccharides, and/or 1.8 to 2.3 less higher oligosaccharides and polysaccharides, than the commercially- available reduced- sugar reduced-calorie products.
- Intermediate carbohydrate compositions were produced, as described in Example 1, having about 45% to about 65% DP3+. These intermediate compositions are designated as 10A-10G feeds.
- the feed materials were diluted with de-ionized water to form solutions of about 40% to about 60% DS.
- the feed solutions were continuously fed to a SMB (simulated moving bed) chromatographic system (a CSEP unit from Calgon Carbon Corporation)
- the DP3+ enriched streams were sequentially passed through a column packed with granular active carbon (Calgon Carbon Corporation) at about 70°C and a flow rate of about 1 ⁇ 2 bed volume/hour, another column packed with Dowex 66 anionic resin (Dow Chemical), and then another column packed with mixed resins of Dowex 22 and Dowex 88 (Dow Chemical) at about 50°C and a flow rate of about 3 bed volumes/hour.
- the carbon and ion-exchange resin treated solution was evaporated at about 70°C to a final syrup of about 75% to about 85% DS.
- These final products i.e., carbohydrate composition according to the present disclosure
- An intermediate carbohydrate composition having about 65% DP3+ was produced as described in Example 1. After diluted with de-ionized water to a form solution of about 60% DS, the feed solution continuously fed to a SMB (simulated moving bed) chromatographic system to produce an extract stream enriched in DP1+DP2, and a raffinate stream enriched in DP3+ oligosaccharides and polysaccharides as described in Example 3.
- SMB simulated moving bed
- the DP3+ rich stream was sequentially passed through a column packed with granular active carbon (Calgon Carbon Corporation) at about 70°C and a flow rate of about 1 ⁇ 2 bed volume/hour, another column packed with Dowex 66 anionic resin (Dow Chemical), and then another column packed with mixed resins of Dowex 22 and Dowex 88 (Dow Chemical) at about 50°C and a flow rate of about 3 bed volumes/hour.
- Cleardex 95® was added at about 8% level based on the dry weight of the mixture in order to produce a product comprising about 92% of a carbohydrate composition according to the disclosure, and about 8% of 95% dextrose corn syrup.
- the mixture was evaporated at about 70°C to a final syrup of about 80% DS.
- This final product i.e., a blend containing the carbohydrate composition of the present disclosure
- 10H1 product i.e., a blend containing the carbohydrate composition of the present disclosure
- the lOH-l product prepared in this example had about 9% glucose pre-enzymatic digestion, and about 26% glucose post-enzymatic digestion, as compared to a traditional 36DE corn syrup product in FIG. 12, which had about 13% glucose pre-enzymatic digestion and about 94% glucose post-enzymatic digestion.
- the comparison shows that, relative to the traditional 36DE corn syrup product, the carbohydrate composition prepared according to the disclosure demonstrates significantly lower digestibility.
- the permethylated material was hydrolyzed using 2 M trifluoroacetic acid (2 hours in a sealed tube at 121°C), reduced with NaBD 4 , and acetylated using acetic anhydride/trifluoroacetic acid.
- the resulting PMAAs were analyzed on a Hewlett Packard 7890A GC interfaced to a 5975C MSD (mass selective detector, electron impact ionization mode EI-MS); separation was performed on a 30m Supelco 2380 bonded phase fused silica capillary column.
- the 2A and 2B products have a very different linkage profile when compared to the commercially- available reduced-sugar low-digestibility products, Fibersol-2 ® resistant maltodextrin, Nutriose ® resistant dextrin, and Promitor TM soluble corn fiber, comprising glucose only.
- the 2A and 2B products have higher degrees of branching as indicated by higher terminal glucose (about 1.4 to about 1.93 times, or about 40% to about 93% higher), along with about 60-75% less 1,4-linkage, about 20-35% more 1,6-linkages, and a 3.5- 4.2 times higher ratio of 1,6-linkage to 1,4-linkage.
- polydextrose has about 1.17 - 1.39 times more 1,2-linkage, and times ( a 24-33% lower ratio of 1,4-linkage to 1,2-linkage.
- polydextrose is a polycondensation polymer of 90% glucose and 10% sorbitol, while the carbohydrate compositions of the present disclosure are polycondensation polymers of only glucose, or comprising less than 10% sorbitol.
- the carbohydrate composition of present disclosure was made to about 20% DS with 0.05M citric buffer of pH 4.5, then treated with 1% (on dry weight basis) enzyme (a glucoamylase and pullulanase enzyme mixture, Optimax4060, Genecor International) at 60°C for 28 hours to convert all digestible carbohydrates to glucose.
- 1% (on dry weight basis) enzyme a glucoamylase and pullulanase enzyme mixture, Optimax4060, Genecor International
- Dry yeast (2.5% on testing material dry weigh basis) was added to the enzyme-treated material and the mixture was vigorously agitated at ambient temperature for 24 hours to fully remove glucose as C0 2 gas.
- Example 7 Granola Bars Comprising Carbohydrate Compositions
- Granola bars were prepared using carbohydrate compositions according to the present disclosure, Litesse II ® polydextrose, and Promitor 85 TM soluble corn fiber, at 25% and 50% sugar reduction along with a full sugar control, as follows.
- the granola bars were prepared as follows. The oats were toasted in a tray dryer at 375°F for about 30-45 seconds until a moisture content of about 4% was achieved. At least 24 hours later, the base ingredients were combined in a lightly-greased mixing bowl. The corn syrup and honey were weighed into Thermomix Vortechniks blender (Wuppertal, DE), and the remaining dry blend was weighed together in a separate container. The oil/lecithin/flavor was then weighed together in a separate container. The syrup/water mixture was heated and mixed in the Thermomix Vorwerks blender to 70°C at speed 3-4. The dry ingredients, followed by the oil/lecithin/flavor ingredients, were added while mixing.
- the instrument test parameters were: pre-test speed 3.0mm/sec; trigger force 15.0 g; test speed 3.0mm/sec; post-test speed lO.Omm/sec. The results were analyzed for maximum force and averaged. Results are shown in FIGS. 8-9.
- Sugar cookies were prepared using carbohydrate compositions according to the present disclosure, Litesse II ® polydextrose, and Promitor 85 TM soluble corn fiber, at 25% and 50% sugar reduction along with a full sugar control, as follows.
- the sugar cookies were prepared by first scaling shortening into the bottom of a Hobart N-50 mixing bowl, and then the sugar and bulking agent (if used), NFDM, salt, and flavor were added. The dough was mixed 1 minute at speed 1, when the mixer was stopped and the bowl scraped. The dough was mixed for another 2 minutes at medium speed. The water/eggs were weighed and added to the mixture, and mixing continued for an additional 2 minutes at speed 1. The flour and baking powder were combined and added to the mixture, and mixing continued for another 1 minute at speed 1. The bowl and paddle were scraped again, and mixing resumed for another 1 minute at speed 1. The cookies were rolled and cut out as per AACC method #10-50, and baked in a reel oven at 375°F for 12 minutes.
- the cookies were tested for hardness a day after baking using TA.XT Plus texture analyzer with a 3 point bend apparatus in which a cookie was placed on parallel rails and a knife blade was used to break the cookie. Hardness of at least 6 and as many as 12 cookies was recorded. Cookies were also analyzed for spread using a standard American Association of Cereal Chemists International (AACCI #10-50) test. The width of 6 cookies was measured using a custom fixture designed for test. For cookie spread, 6 cookies were lined up and a measurement taken in millimeters. The cookies were turned 90° and the measurement taken again as per protocol and then repeated a 3 time. The measurements were averaged and results are shown in FIGS. 10-11.
- foodstuffs comprising the carbohydrate compositions described herein have shown properties relative to existing reduced- sugar, reduced-calorie sweeteners, e.g., Litesse polydextrose, Nutriose resistant dextrin, Fibersol-2 resistant maltodextrin, and Promitor soluble corn fiber, that are just as good or are improved.
- reduced-calorie sweeteners e.g., Litesse polydextrose, Nutriose resistant dextrin, Fibersol-2 resistant maltodextrin, and Promitor soluble corn fiber
- carbohydrate compositions prepared according to embodiments of the disclosure can comprise a total soluble dietary fiber content of greater than about 60% by weight of the composition.
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EP14764326.6A EP2983514A4 (en) | 2013-03-15 | 2014-03-15 | Carbohydrate compositions |
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1982003329A1 (en) * | 1981-03-31 | 1982-10-14 | David B A Silk | Glucose polymers and method of producing same |
EP0530111B1 (en) * | 1991-08-28 | 1999-06-23 | Matsutani Chemical Industries Co. Ltd. | Indigestible dextrin |
WO2000015829A1 (en) * | 1998-09-14 | 2000-03-23 | General Electric Company | FERMENTATION MEDIUM AND METHOD FOR PRODUCING α,φ-ALKANEDICARBOXYLIC ACIDS |
US6630586B1 (en) * | 1998-12-04 | 2003-10-07 | Roquette Freres | Branched maltodextrins and method of preparing them |
US20060172392A1 (en) * | 2001-02-16 | 2006-08-03 | Cargill, Incorporated | Water soluble beta-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same |
US20110061645A1 (en) * | 2008-05-09 | 2011-03-17 | Cargill, Incorporated | Low-viscosity reduced-sugar syrup, methods of making, and applications thereof |
WO2011057291A1 (en) * | 2009-11-09 | 2011-05-12 | Georgia Tech Research Corporation | Improved methods of enzymatic hydrolysis |
US20120165290A1 (en) * | 2009-05-08 | 2012-06-28 | Lubbert Dijkhuizen | Glucooligosaccharides comprising (alpha 1->4) and (alpha 1->6) glycosidic bonds, use thereof, and methods for providing them |
Family Cites Families (93)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2719179A (en) | 1951-01-25 | 1955-09-27 | Mora Peter Tibor | Branched-chain carbohydrate polymers and their preparation |
US3766165A (en) | 1966-08-17 | 1973-10-16 | Pfizer | Polysaccharides and their preparation |
FR1600591A (en) | 1968-02-14 | 1970-07-27 | ||
JPS567665B1 (en) | 1969-01-24 | 1981-02-19 | ||
US3654082A (en) | 1969-02-10 | 1972-04-04 | Cpc International Inc | Production of high maltotetraose syrup |
JPS529739B1 (en) | 1969-04-09 | 1977-03-18 | ||
IT1035516B (en) | 1969-10-24 | 1979-10-20 | Hayashibara Co | PROCEDURE FOR THE PRODUCTION OF STARCH SYRUPS |
US3756853A (en) | 1970-10-27 | 1973-09-04 | Cpc International Inc | Process for the production of nonhazing starch conversion syrups |
US3876794A (en) | 1972-12-20 | 1975-04-08 | Pfizer | Dietetic foods |
US4009291A (en) | 1974-03-25 | 1977-02-22 | General Foods Corporation | Cold water soluble stable bulked starch |
US4011392A (en) | 1975-09-02 | 1977-03-08 | The Sherwin-Williams Company | Mixed starch esters and the use thereof |
US4017363A (en) | 1975-12-19 | 1977-04-12 | Novo Industri A/S | Production of high purity glucose syrups |
US4144357A (en) | 1977-06-22 | 1979-03-13 | Johnson & Johnson | Preventing the Maillard reaction in synthetic dietary compositions |
US4182756A (en) | 1977-11-21 | 1980-01-08 | Abbott Laboratories | High calorie solutions of low molecular weight glucose polymer mixtures useful for intravenous administration |
FR2445839A1 (en) | 1979-01-08 | 1980-08-01 | Roquette Freres | HYDROLYSATE OF POSSIBLE HYDROGEN STARCH, PROCESS FOR THE PREPARATION THEREOF AND APPLICATIONS THEREOF |
JPS594119B2 (en) | 1982-03-09 | 1984-01-27 | 工業技術院長 | Method for producing oligosaccharides using amylase G4,5 |
JPS61205494A (en) | 1985-03-11 | 1986-09-11 | Sanmatsu Kogyo Kk | Production of branched dextrin and straight-chain oligosaccharide |
JPH0614872B2 (en) | 1985-03-15 | 1994-03-02 | 昭和産業株式会社 | Method for producing branched oligosaccharide syrup |
JPS61227777A (en) | 1985-04-02 | 1986-10-09 | Showa Sangyo Kk | Agent for activating growth of bifidus bacteria |
JPS6416596A (en) | 1987-07-09 | 1989-01-20 | Japan Maize Prod | Starch sugar containing maltotetraose as main component |
US4965354A (en) | 1988-02-26 | 1990-10-23 | Taito Company, Ltd. | Process for producing a condensed polysaccharide |
JP2721968B2 (en) | 1988-02-29 | 1998-03-04 | 日本食品化工株式会社 | Novel enzyme and method for producing syrup containing high content of gentio-oligosaccharide |
US4941990A (en) | 1988-03-10 | 1990-07-17 | Mclaughlin James H | Skin cleansing-cream conditioning bar |
US5266467A (en) | 1988-05-02 | 1993-11-30 | The United States Of America As Represented By The Secretary Of Agriculture | Enzymatic production of maltohexaose-rich compositions |
US5667593A (en) | 1989-01-26 | 1997-09-16 | Cultor Ltd. | Modified polydextrose and process therefor |
JP2750374B2 (en) | 1989-02-21 | 1998-05-13 | 日本食品化工株式会社 | Novel production method of β-glucooligosaccharide by oxygen method |
US5219842A (en) | 1989-08-29 | 1993-06-15 | Nihon Shokuhin Kako Co., Ltd. | Method of improving intestinal floras |
US5811542A (en) | 1989-09-08 | 1998-09-22 | Alpha-Beta Technology, Inc. | Method for producing soluble glucans |
DK165769C (en) | 1989-09-22 | 1993-06-14 | Danisco | PROCEDURE FOR PREPARING A MIXTURE OF SUCCARIDES AND USING THE MIXTURE IN THE PREPARATION OF A CALORIC FOOD |
US5087461A (en) | 1989-10-02 | 1992-02-11 | Nabisco Brands, Inc. | Double-encapsulated compositions containing volatile and/or labile components, and processes for preparation and use thereof |
JPH03133387A (en) | 1989-10-19 | 1991-06-06 | Nichiden Kagaku Kk | Production of maltooligosaccharide |
JP2729406B2 (en) | 1989-12-27 | 1998-03-18 | 松谷化学工業株式会社 | Method for producing indigestible heteropolysaccharide |
JP2829329B2 (en) | 1990-06-11 | 1998-11-25 | 塩水港精糖株式会社 | Process for producing maltopentaose starch syrup |
US5756721A (en) | 1991-01-16 | 1998-05-26 | National Starch And Chemical Investment Holding Corporation | Purification of polysaccharides |
ATE145407T1 (en) | 1991-02-20 | 1996-12-15 | Pfizer | REDUCED POLYDEXTROSE |
JP3030916B2 (en) | 1991-02-22 | 2000-04-10 | 味の素株式会社 | Method for producing β-glucooligosaccharide |
JP3142906B2 (en) | 1991-08-07 | 2001-03-07 | 日本食品化工株式会社 | Food and drink, taste, cosmetics and pharmaceuticals, and method for producing starch sugar-containing composition |
US5124162A (en) | 1991-11-26 | 1992-06-23 | Kraft General Foods, Inc. | Spray-dried fixed flavorants in a carbohydrate substrate and process |
AU649909B2 (en) | 1992-02-07 | 1994-06-02 | National Starch And Chemical Investment Holding Corporation | Purification of polysaccharides |
FR2688800B1 (en) | 1992-03-19 | 1995-06-16 | Roquette Freres | PROCESS FOR THE PREPARATION OF LOW DIGESTIBLE POLYSACCHARIDES, POSSIBLY HYDROGENIC. |
GB9219552D0 (en) | 1992-09-16 | 1992-10-28 | Unilever Plc | Processing of maltodextrins |
FR2697023B1 (en) | 1992-10-16 | 1994-12-30 | Roquette Freres | Low-calorie glucose soluble polymer and process for the preparation of this polymer. |
JPH0770165A (en) | 1993-06-28 | 1995-03-14 | Hayashibara Biochem Lab Inc | Nonreducing oligosaccharide, its production and use thereof |
FR2712891B1 (en) | 1993-11-22 | 1996-02-02 | Roquette Freres | Process for the purification of a hypocaloric soluble polymer of glucose and product thus obtained. |
JP3793590B2 (en) | 1994-06-27 | 2006-07-05 | 株式会社林原生物化学研究所 | Non-reducing saccharides, production method and use thereof |
NL1001956C2 (en) | 1995-12-21 | 1997-06-24 | Suiker Unie | Process for the preparation of purified inulin. |
EP1469081B1 (en) | 1996-05-15 | 2008-07-16 | Nihon Shokuhin Kako Co., Ltd. | Food and drink containing nigerooligosaccharide alcohols |
ES2169263T3 (en) | 1996-09-17 | 2002-07-01 | Amylum Europe Nv | PROCEDURE FOR THE PREPARATION OF GLUCOSE SYRUPS BY ENZYMATIC CONVERSION. |
AU6764998A (en) | 1997-03-19 | 1998-10-12 | Cultor Food Science, Inc. | Polymerization of mono-and disaccharides using low levels of mineral acids |
US6475552B1 (en) | 1997-03-19 | 2002-11-05 | Danisco Finland Oy | Polymerization of mono and disaccharides using low levels of polycarboxylic acids |
ATE218588T1 (en) | 1997-03-19 | 2002-06-15 | Danisco Cultor America Inc | POLYMERIZATION OF MONO- AND DISACCHARIDES IN THE PRESENCE OF SMALL AMOUNTS OF POLYCARBONIC ACIDS |
FR2766333B1 (en) | 1997-07-25 | 1999-10-01 | Roquette Freres | NOVEL SWEETENING COMPOSITION, PROCESS FOR PRODUCING THE SAME AND USES THEREOF |
US6329182B1 (en) | 1997-11-26 | 2001-12-11 | Novozymes A/S | Method of producing oligosaccharide syrups, a system for producing the same and oligosaccharide syrups |
EP1049720A1 (en) | 1998-01-20 | 2000-11-08 | Grain Processing Corporation | Reduced malto-oligosaccharides |
US6919446B1 (en) | 1998-01-20 | 2005-07-19 | Grain Processing Corp. | Reduced malto-oligosaccharides |
US6287826B1 (en) | 1998-03-09 | 2001-09-11 | Novo Nordisk A/S | Enzymatic preparation of glucose syrup from starch |
US6780990B1 (en) | 1998-03-26 | 2004-08-24 | Spi Polyols, Inc. | Hydrogenated starch hydrolysate |
US6713116B1 (en) | 1998-03-26 | 2004-03-30 | Nutrinova Inc. | Sweet-stable acidified beverages |
US6348264B1 (en) | 1998-04-27 | 2002-02-19 | Roquette Freres | Process for producing low de starch hydrolysates by nanofiltration fractionation, products obtained thereby, and use of such products |
US6068705A (en) | 1998-04-27 | 2000-05-30 | Roquette Freres | Process for producing low De starch hydrolysates by nanofiltration fractionation, products obtained thereby, and use of such products |
US5853487A (en) | 1998-04-27 | 1998-12-29 | Roquette Freres | Process for producing low de starch hydrolysates by nanofiltration fractionation and blending of resultant products, preferably in liquid form, with other carbohydrates |
US6423833B1 (en) | 1998-05-05 | 2002-07-23 | Steven J. Catani | Functional sugar polymers from inexpensive sugar sources and apparatus for preparing same |
US6126986A (en) | 1999-02-23 | 2000-10-03 | Westway Trading Corporation | Process for formulating a liquid animal feed ingredient containing sugar and neutralized carboxylic acid |
US6380379B1 (en) | 1999-08-20 | 2002-04-30 | Grain Processing Corporation | Derivatized reduced malto-oligosaccharides |
DE50107849D1 (en) | 2000-07-28 | 2005-12-01 | Henkel Kgaa | NEW AMYLOLYTIC ENZYME FROM BACILLUS SP. A 7-7 (DSM 12368) AND WASHING AND CLEANING AGENT WITH THIS NEW AMYLOLYTIC ENZYME |
GB0018849D0 (en) | 2000-08-01 | 2000-09-20 | Smithkline Beecham Plc | Novel composition and use |
JP3983522B2 (en) | 2001-11-15 | 2007-09-26 | 千葉製粉株式会社 | Method for producing branched dextrin liquid |
JP2003231694A (en) | 2002-02-06 | 2003-08-19 | Hokkaido Electric Power Co Inc:The | Method for producing saccharide polymer and glycosides |
US20050048191A1 (en) | 2003-06-23 | 2005-03-03 | Grain Processing Corporation | Dextrinized, saccharide-derivatized oligosaccharides |
FR2842222B1 (en) | 2002-07-10 | 2004-09-24 | Roquette Freres | PROCESS FOR TREATING A FIBROUS TABLECLOTH WITH AN ADHESIVE COMPOSITION BASED ON POLYMER (S) CONTAINING A PARTICULAR COMBINATION OF SACCHARIDES |
FI20021772A (en) | 2002-10-04 | 2004-04-05 | Biotie Therapies Oyj | Novel carbohydrate compositions and process for their preparation |
WO2006047176A1 (en) | 2004-10-22 | 2006-05-04 | Cargill, Incorporated | Process for the production of maltodextrins and maltodextrins |
US20060223937A1 (en) | 2005-04-04 | 2006-10-05 | Herr Donald E | Radiation curable cycloaliphatic barrier sealants |
US20060223978A1 (en) | 2005-04-04 | 2006-10-05 | Shengqian Kong | Radiation- or thermally-curable oxetane barrier sealants |
US20070116839A1 (en) | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition With C-Reactive Protein Reducing Substance and Compositions Sweetened Therewith |
US20070116825A1 (en) | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | Confection with High-Potency Sweetener |
ES2706281T3 (en) | 2005-12-20 | 2019-03-28 | Nutricia Nv | Composition of carbohydrates and decreased glucose response |
US8993039B2 (en) | 2006-01-25 | 2015-03-31 | Tate & Lyle Ingredients Americas Llc | Fiber-containing carbohydrate composition |
US7608436B2 (en) | 2006-01-25 | 2009-10-27 | Tate & Lyle Ingredients Americas, Inc. | Process for producing saccharide oligomers |
US8057840B2 (en) | 2006-01-25 | 2011-11-15 | Tate & Lyle Ingredients Americas Llc | Food products comprising a slowly digestible or digestion resistant carbohydrate composition |
EP2027160B1 (en) | 2006-06-15 | 2012-04-25 | SYRAL Belgium NV | Process for preparing randomly-bonded polysaccharides |
WO2009113652A1 (en) | 2008-03-14 | 2009-09-17 | 松谷化学工業株式会社 | Branched dextrin, process for production thereof, and food or beverage |
US9730464B2 (en) * | 2008-05-09 | 2017-08-15 | Cargill, Incorporated | Carbohydrate compositions |
US9999240B2 (en) * | 2008-05-09 | 2018-06-19 | Cargill, Incorporated | Carbohydrate compositions |
WO2010020321A1 (en) | 2008-08-20 | 2010-02-25 | Cargill, Incorporated | New polydextrose material |
US8435590B2 (en) | 2008-11-24 | 2013-05-07 | Stokely-Van Camp, Inc. | Use of novel carbohydrates and carbohydrate blends to provide a sports beverage with increased absorption |
EP2405918B2 (en) | 2009-03-13 | 2020-09-02 | The Regents of The University of California | Prebiotic oligosaccharides |
WO2010106384A1 (en) | 2009-03-16 | 2010-09-23 | Societe La Biochimie Appliquee (Solabia) | Glucooligosaccharide nutraceutical, pharmaceutical, or food compositions |
US8999066B2 (en) | 2009-04-17 | 2015-04-07 | Archer Daniels Midland Co. | Bleached dextrin and methods of forming same |
FR2945043B1 (en) | 2009-04-30 | 2019-07-26 | Roquette Freres | PROCESS FOR PURIFYING GLUCOSE POLYMERS FOR PERITONEAL DIALYSIS SOLUTIONS |
JPWO2011071179A1 (en) | 2009-12-11 | 2013-04-22 | 松谷化学工業株式会社 | Sustainable energy supplement and food and drink |
FR2955861B1 (en) | 2010-02-02 | 2013-03-22 | Roquette Freres | SOLUBLE GLUCOSE BRANCHES POLYMERS FOR PERITONEAL DIALYSIS |
US20120034366A1 (en) | 2010-08-05 | 2012-02-09 | Tate & Lyle Ingredients Americas, Inc. | Carbohydrate compositions |
-
2014
- 2014-03-15 CA CA2906984A patent/CA2906984A1/en not_active Abandoned
- 2014-03-15 WO PCT/US2014/030010 patent/WO2014145276A1/en active Application Filing
- 2014-03-15 EP EP14764326.6A patent/EP2983514A4/en active Pending
- 2014-03-15 BR BR112015023484A patent/BR112015023484A2/en not_active IP Right Cessation
- 2014-03-15 US US14/777,241 patent/US11291222B2/en active Active
- 2014-03-15 MX MX2015013157A patent/MX2015013157A/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1982003329A1 (en) * | 1981-03-31 | 1982-10-14 | David B A Silk | Glucose polymers and method of producing same |
EP0530111B1 (en) * | 1991-08-28 | 1999-06-23 | Matsutani Chemical Industries Co. Ltd. | Indigestible dextrin |
WO2000015829A1 (en) * | 1998-09-14 | 2000-03-23 | General Electric Company | FERMENTATION MEDIUM AND METHOD FOR PRODUCING α,φ-ALKANEDICARBOXYLIC ACIDS |
US6630586B1 (en) * | 1998-12-04 | 2003-10-07 | Roquette Freres | Branched maltodextrins and method of preparing them |
US20060172392A1 (en) * | 2001-02-16 | 2006-08-03 | Cargill, Incorporated | Water soluble beta-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same |
US20110061645A1 (en) * | 2008-05-09 | 2011-03-17 | Cargill, Incorporated | Low-viscosity reduced-sugar syrup, methods of making, and applications thereof |
US20120165290A1 (en) * | 2009-05-08 | 2012-06-28 | Lubbert Dijkhuizen | Glucooligosaccharides comprising (alpha 1->4) and (alpha 1->6) glycosidic bonds, use thereof, and methods for providing them |
WO2011057291A1 (en) * | 2009-11-09 | 2011-05-12 | Georgia Tech Research Corporation | Improved methods of enzymatic hydrolysis |
Non-Patent Citations (3)
Title |
---|
HOBBS, L.: "Sweeteners from Starch: Production, Properties and Uses.", STARCH: CHEMISTRY AND TECHNOLOGY, 2009, pages 797 - 832, XP055281283, Retrieved from the Internet <URL:http://nfscfaculty.tamu.edu/talcott/courses/FSTC605/Papers%20Reviewed/Sweetners%20from%20starch.pdf> * |
See also references of EP2983514A4 * |
WOICIECHOWSKI, AL ET AL.: "Acid and Enzymatic Hydrolysis to Recover Reducing Sugars from Cassava Bagasse: an Economic Study.", BRAZILIAN ARCHIVES OF BIOLOGY AND BIOTECHNOLOGY, vol. 45, no. 3, September 2002 (2002-09-01), pages 292 - 400, XP055287215 * |
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Also Published As
Publication number | Publication date |
---|---|
EP2983514A1 (en) | 2016-02-17 |
US20160015065A1 (en) | 2016-01-21 |
EP2983514A4 (en) | 2017-03-15 |
BR112015023484A2 (en) | 2017-07-18 |
MX2015013157A (en) | 2015-12-11 |
CA2906984A1 (en) | 2014-09-18 |
US11291222B2 (en) | 2022-04-05 |
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