Composition for sustained release of caffeine

Abstract

The present disclosure relates to complexes containing caffeine and tannic acid, and emulsions and beverages containing these complexes that delay the release of caffeine. Methods for preparing the complexes and emulsions and beverages containing the caffeine-tannic acid complexes are also described.

Description

[Technical field]

[0001] The present disclosure relates to complexes containing caffeine and tannic acid and emulsions containing these complexes. The complexes delay the release of caffeine when used in beverages. A method for preparing beverages containing the tannic acid and caffeine complexes is also described. [Background technology]

[0002] Caffeine is one of the most widely used pharmacologically active compounds. Previous studies have determined that caffeine is absorbed by the gastrointestinal tract with peak concentrations occurring between 15 and 120 minutes after ingestion ("Caffeine use in sports, pharmacokinetics in man, and cellular mechanisms of action," Crit Rev Food Sci Nutr. 2005;45(7-8);535-62). Prolonging the release of caffeine from beverages such as soft drinks allows the body to absorb caffeine gradually, avoiding jitteriness and the "caffeine crash." Summary of the Invention

[0003] In a first aspect, the present disclosure provides a complex comprising caffeine and tannic acid. In a first embodiment of the first aspect, the weight / weight ratio of caffeine to tannic acid in the complex is about 10:1 to about 1:10. In a second embodiment of the first aspect, the weight / weight ratio of caffeine to tannic acid in the complex is about 5:1 to about 1:5. In a third embodiment of the first aspect, the weight / weight ratio of caffeine to tannic acid in the complex is about 4:1 to about 1:4. In a fifth embodiment of the first aspect, the weight percentage of caffeine in the complex is about 23% to about 35%. In a sixth embodiment of the first aspect, the weight percentage of caffeine in the complex is about 35% to about 53%.

[0004] In a seventh embodiment of the first aspect the complex comprises an additional compound selected from the group consisting of citric acid, dopamine, maleic acid, malonic acid, and oxalic acid.

[0005] In a second aspect, the present disclosure provides an emulsion comprising an oil phase comprising at least one oil comprising a complex comprising caffeine and tannic acid, and an aqueous phase comprising water. In a first embodiment of the second aspect, the emulsion further comprises one or more stabilizers. In a second embodiment of the second aspect, the emulsion further comprises one or more emulsifiers.

[0006] In a third embodiment of the second aspect, the emulsion further comprises from about 2% to about 30% by weight of at least one oil. In a fourth embodiment of the second aspect, the emulsion comprises from about 5% to about 10% by weight of at least one oil. In a fifth embodiment of the second aspect, the at least one oil is selected from the group consisting of one or more edible oils, one or more edible waxes, and combinations thereof. In a sixth embodiment of the second aspect, the at least one oil is selected from the group consisting of ghee, mustard oil, olive oil, rice bran oil, linseed oil, peanut oil, sesame oil, almond oil, cashew oil, canola oil, soybean oil, avocado oil, walnut oil, grape seed oil, sunflower oil, medium chain triglycerides, coconut oil, palm kernel oil, carnauba wax, beeswax, paraffin wax, rice bran wax, candelilla wax, sunflower wax, sugarcane wax, propolis wax, shellac wax, and combinations thereof. In a seventh embodiment of the second aspect, the at least one oil is selected from the group consisting of sunflower oil and medium chain triglycerides.

[0007] In an eighth embodiment of the second aspect, the emulsion comprises from about 0.1% to about 15% by weight of the complex. In a ninth embodiment, the emulsion comprises from about 1% to about 4% by weight of the complex.

[0008] In a tenth embodiment, the emulsion comprises from about 0.002% to about 8% by weight of one or more stabilizers. In an eleventh embodiment of the second aspect, the emulsion comprises from about 0.08% to about 1.2% by weight of one or more stabilizers. In a twelfth embodiment of the second aspect, the one or more stabilizers are selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof. In a thirteenth embodiment of the second aspect, the one or more stabilizers are selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, and combinations thereof.

[0009] In a fourteenth embodiment of the second aspect, the emulsion comprises about 4% to about 40% by weight of one or more emulsifiers. In a fifteenth embodiment of the second aspect, the emulsion comprises about 10% by weight of one or more emulsifiers. In a sixteenth embodiment of the second aspect, the one or more emulsifiers are selected from the group consisting of agar, carrageenan, gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, and combinations thereof. In a seventeenth embodiment of the second aspect, the one or more stabilizers are gum arabic.

[0010] In a third aspect, the present disclosure provides a process for preparing a complex comprising caffeine and tannic acid, the process comprising adding tannic acid and caffeine to ethanol or aqueous ethanol and spray drying the resulting solution.

[0011] In a fourth aspect, the present disclosure provides a process for preparing a complex comprising caffeine and tannic acid, the process comprising adding an aqueous solution of tannic acid to an aqueous solution of caffeine and filtering the resulting suspension.

[0012] In a fifth aspect, the present disclosure provides a process for preparing an emulsion comprising a complex comprising caffeine and tannic acid, the process comprising adding a mixture of the complex, at least one oil, and optionally one or more stabilizers to a mixture of water and optionally one or more emulsifiers, and mixing at high speed.

[0013] In a sixth aspect, the present disclosure provides a beverage comprising an emulsion comprising a complex comprising caffeine and tannic acid. [Brief description of the drawings]

[0014] The present disclosure is illustrated by way of example and not by way of limitation in the accompanying drawings.

[0015] [Figure 1A] 1 shows the FT IR spectrum of caffeine.

[0016] [Figure 1B] 1 shows the FT IR spectrum of tannic acid.

[0017] [Figure 2A] 1 shows the FT IR spectrum of a 1:1 mixture of caffeine and tannic acid.

[0018] [Figure 2B] 1 shows the FT IR spectrum of a complex containing tannic acid:caffeine in a 1:1 wt / w ratio.

[0019] [Diagram 3] FT IR spectra of a 1:3 mixture of caffeine and tannic acid, a complex containing 1:3 wt / w caffeine:tannic acid prepared by aqueous precipitation method, and a complex containing 1:3 wt / w caffeine:tannic acid.

[0020] [Figure 4]FIG. 1 shows the caffeine release rate from caffeine-tannic acid complexes containing various amounts of tannic acid as determined by dialysis using dialysis bags with a molecular weight cutoff of 14,000 and centrifugation.

[0021] [Diagram 5] FIG. 1 shows the caffeine release rate from a complex containing tannic acid, caffeine, and an additional organic acid as determined by dialysis using a dialysis bag with a molecular weight cutoff of 14,000.

[0022] [Figure 6] FIG. 1 shows the caffeine release rate from complexes containing tannic acid, caffeine, and various amounts of dopamine, as determined by dialysis using dialysis bags with a molecular weight cutoff of 14,000.

[0023] [Figure 7A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 1% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0024] [Figure 7B] FIG. 1 shows the change in the amount of encapsulated caffeine over time when an emulsion containing 1% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0025] [Figure 8A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 4% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0026] [Figure 8B] FIG. 13 shows the change in the amount of encapsulated caffeine over time when an emulsion containing 4% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0027] [Figure 9A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 5% stearic acid and 1% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0028] [Figure 9B] FIG. 1 shows the change in the amount of encapsulated caffeine over time when an emulsion containing 5% stearic acid and 1% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0029] [Figure 10A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 5% stearic acid and 4% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0030] [Figure 10B] FIG. 1 shows the change in the amount of encapsulated caffeine over time when an emulsion containing 5% stearic acid and 4% sorbitan trioleate was subjected to dialysis conditions and analyzed using a 1K filter.

[0031] [Figure 11A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 1% polyglycerol polyricinoleate (PGPR) was subjected to dialysis conditions and analyzed using a 1K filter.

[0032] [Figure 11B] FIG. 1 shows the change in the amount of encapsulated caffeine over time when an emulsion containing 1% PGPR was subjected to dialysis conditions and analyzed using a 1K filter.

[0033] [Figure 12A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 4% PGPR was subjected to dialysis conditions and analyzed using a 1K filter.

[0034] [Figure 12B] FIG. 13 shows the amount of caffeine encapsulated over time when an emulsion containing 4% PGPR was subjected to dialysis conditions and analyzed using a 1K filter.

[0035] [Figure 13A] FIG. 1 shows the change in the amount of free caffeine over time when an emulsion containing 8% PGPR was subjected to dialysis conditions and analyzed using a 1K filter.

[0036] [Figure 13B] FIG. 1 shows the amount of caffeine encapsulated over time when an emulsion containing 8% PGPR was subjected to dialysis conditions and analyzed using a 1K filter.

[0037] [Figure 14A] 1 shows the change in the amount of free caffeine over time when an emulsion containing medium chain triglycerides is subjected to dialysis conditions using a dialysis bag with a molecular weight cutoff of 14,000.

[0038] [Figure 14B] FIG. 1 shows the amount of caffeine encapsulated over time when emulsions containing medium chain triglycerides are subjected to dialysis conditions using dialysis bags with a molecular weight cutoff of 14,000.

[0039] [Figure 15A] FIG. 1 shows the amount of caffeine encapsulated over time when emulsions containing sunflower oil are subjected to dialysis conditions using dialysis bags with a molecular weight cutoff of 14,000.

[0040] [Figure 15B] FIG. 1 shows the amount of caffeine released over time from emulsions containing sunflower oil subjected to dialysis conditions using dialysis bags with a molecular weight cut off of 14,000.

[0041] [Figure 16] FIG. 1 shows the amount of caffeine encapsulated over time in various emulsions subjected to dialysis conditions using dialysis bags with a molecular weight cutoff of 14,000.

[0042] [Figure 17] 1 shows the amount of caffeine released from a representative beverage containing a representative emulsion when subjected to simulated gastric conditions. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0043] definition The singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise.

[0044] As used herein, the term "or" indicates a logical branch (i.e., and / or) and not an exclusive branch, unless expressly indicated as such by the terms "either," "unless," "alternatively," and words of similar effect.

[0045] As used herein, the term "about" refers to ±10% of the stated value, unless otherwise specified, and unless the upper limit of the range exceeds 100% of the composition, in which case the upper limit of the range is limited to 99.9%. Thus, by way of example only, a composition containing about 10% by weight of a given component may have 9-11% by weight of the compound. Similarly, a composition containing about 95% by weight of a given component may have 85.5-99.9% by weight of the component in the composition.

[0046] As used herein, "beverage" refers to an edible formulation suitable for drinking. Examples of beverages include, but are not limited to, soft drinks, fountain drinks, frozen ready-to-drink beverages, coffee drinks, tea drinks, sports drinks, juices, dairy drinks, and alcoholic beverages. Beverages may be carbonated or non-carbonated and may be clear, i.e., transparent, translucent, or opaque. As used herein, "fountain beverage" refers to a beverage prepared by combining a beverage syrup with water, which may be optionally carbonated at or just prior to consumption.

[0047] As used herein, the term "emulsifying agent" refers to an agent that allows the aqueous phase and the oil phase to blend into an emulsion. Examples of suitable emulsifying agents include, but are not limited to, agar, carrageenan, protein-derived emulsifiers (e.g., whey protein isolate and sodium caseinate), gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, and combinations thereof. Additional examples of emulsifying agents will be apparent to those skilled in the art of food or beverage formulation, given the benefit of this disclosure.

[0048] As used herein, the term "stabilizer" refers to an agent that stabilizes the caffeine-tannic acid complex in one or more oils of the emulsion described herein.Exemplary stabilizers include, but are not limited to, sorbitan trioleate, stearic acid, ethyl cellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof.Further examples of stabilizers will be apparent to those skilled in the art of food or beverage formulation, given the benefit of this disclosure.

[0049] All percentages provided herein are by weight unless otherwise specified.

[0050] Caffeine-Tannic Acid Complex The present disclosure provides a complex comprising caffeine and tannic acid. In certain embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 10:1 to about 1:10. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 9:1 to about 1:9. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 8:1 to about 1:8. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 7:1 to about 1:7. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 6:1 to about 1:6. In certain embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 5:1 to about 1:5. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 4:1 to about 1:4. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 2:1 to about 1:4. In some embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 2:1 to about 1:3. In certain embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 1:1. In certain embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 1:2. In certain embodiments, the weight / weight ratio of caffeine to tannic acid in the complex may be about 1:3.

[0051] In certain embodiments, the weight percentage of caffeine in the complex may be about 5% to about 95%. In some embodiments, the weight percentage of caffeine in the complex may be about 10% to about 90%. In some embodiments, the weight percentage of caffeine in the complex may be about 15% to about 85%. In some embodiments, the weight percentage of caffeine in the complex may be about 20% to about 80%. In some embodiments, the weight percentage of caffeine in the complex may be about 20% to about 70%. In some embodiments, the weight percentage of caffeine in the complex may be about 20% to about 60%. In some embodiments, the weight percentage of caffeine in the complex may be about 20% to about 50%. In some embodiments, the weight percentage of caffeine in the complex may be about 23% to about 35%. In some embodiments, the weight percentage of caffeine in the complex may be about 35% to about 53%. In certain embodiments, the weight percentage of caffeine in the complex is about 5%, about 10%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, about 25%, about 26%, about 27%, about 28%, about 29%, about 30%, about 31%, about 32%, about 33%, about 34%, about 35%, about 36%, about 37%, about 38%, about 39%, about 40%, about 41%, about 42%, about 43%, about 44%, about 45%, about 46%, about 47%, about 48%, about 49%, about 50%, about 51%, about 52%, about 53%, about 54%, about 55%, about 56%, about 57%, about 58%, about 59%, about 60%, about 61%, about 62%, about 63%, about 64%, about 65%, about 66%, about 67%, about 68%, about 69%, about 70%, about 71%, about 72%, about 73%, about 74%, about 75%, about 76%, about 77%, about 78%, about 79%, about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, about 99%, about 100%, about 101%, about 102%, about 103%, about 104%, about 105%, about 106%, about 107%, about 108%, about 109%, about %, about 38%, about 39%, about 40%, about 41%, about 42%, about 43%, about 44%, about 45%, about 46%, about 47%, about 48%, about 49%, about 50%, about 51%, about 52%, about 53%, about 54%, about 55%, about 56%, about 57%, about 58%, about 59%, about 69%, about 65%, about 70%, about 75%, about 80%, about 85%, or about 90%.

[0052] In certain embodiments, the complex may include caffeine, tannic acid, and an additional compound selected from the group consisting of citric acid, dopamine, maleic acid, malonic acid, and oxalic acid. Without being bound by any particular theory, it is believed that under the conditions described herein, tannic acid forms hydrogen bonds with caffeine molecules to provide a stable complex that, when used in a beverage, slows the release of caffeine from the beverage. The formation of the caffeine-tannic acid complex is supported by spectroscopic analysis, such as FT-IR data, which are discussed elsewhere herein. Surprisingly, the FT-IR spectrum of the caffeine-tannic acid complex is significantly different from the spectrum of a non-complexed mixture of caffeine and tannic acid. This data demonstrates that the caffeine and tannic acid molecules are associated with each other within the complex.

[0053] Compositions containing the complex The present disclosure further provides aqueous emulsions comprising the complexes described herein. These emulsions provide a sustained release of caffeine when used in beverages. Without being bound to a particular theory, it is believed that the emulsion particles encapsulate the caffeine complexes and delay the release of free caffeine into the beverage. The emulsions of the present disclosure include caffeine-tannic acid complexes, water (as part of the aqueous phase dispersed throughout the emulsion), one or more oils (as part of the oil phase dispersed throughout the emulsion), optionally one or more emulsifiers, and optionally one or more stabilizers. The emulsions can be water-in-oil emulsions or oil-in-water emulsions. In a typical embodiment, the emulsions are oil-in-water emulsions.

[0054] In certain embodiments, the emulsion can include from about 0.1% to about 15% by weight of the complex comprising caffeine and tannic acid. In certain embodiments, the emulsion can include from about 0.1% to about 12% by weight of the complex comprising caffeine and tannic acid. In certain embodiments, the emulsion can include from about 0.1% to about 10% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 0.15% to about 8% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 0.2% to about 6% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 0.25% to about 5% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 0.50% to about 4.5% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 0.75% to about 4% by weight of a complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 1% to about 3.5% by weight of a complex comprising caffeine and tannic acid. In some embodiments, the emulsion can include from about 1.5% to about 3% by weight of a complex comprising caffeine and tannic acid.In some embodiments, the emulsion comprises about 0.1 wt%, about 0.15 wt%, about 0.2 wt%, 0.25 wt%, about 0.35 wt%, about 0.45 wt%, about 0.55 wt%, about 0.65 wt%, about 0.75 wt%, about 0.80 wt%, about 0.85 wt%, about 0.90 wt%, about 1.0 wt%, about 1.25 wt%, about 1.5 wt%, about 1.75 wt%, about 2.0 wt%, about 2.25 wt%, about 2.5 wt%, about 2.75 wt%, about 3.0 wt%, about 3.25 wt%, about 3.5 wt%, about 3.75 wt%, about 4.0 wt%, The composition may comprise about 4.25%, about 4.5%, about 4.75%, about 5%, about 5.25%, about 5.5%, about 5.75%, about 6%, about 6.25%, about 6.5%, about 6.75%, about 7%, about 7.25%, about 7.5%, about 7.75%, about 8%, about 8.25%, about 8.5%, about 8.75%, about 9%, about 9.25%, about 9.5%, about 9.75%, about 10%, about 12%, or about 15% by weight of a complex comprising caffeine and tannic acid.

[0055] In some embodiments, the emulsion can comprise an oil phase comprising about 2% to about 30% by weight of at least one oil. In some embodiments, the emulsion can comprise an oil phase comprising about 2% to about 25% by weight of at least one oil. In some embodiments, the emulsion can comprise an oil phase comprising about 2% to about 20% by weight of at least one oil. In some embodiments, the emulsion can comprise an oil phase comprising about 5% to about 10% by weight of at least one oil. In some embodiments, the emulsion can comprise about 6% to about 9% by weight of at least one oil. In some embodiments, the emulsion can comprise about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 15%, about 18%, about 20%, about 23%, about 25%, about 28%, or about 30% by weight of at least one oil.

[0056] Typically, in certain embodiments, the at least one oil can comprise one or more edible oils and / or one or more edible waxes. In some embodiments, the at least one oil can comprise one or more oils selected from the group consisting of ghee, mustard oil, olive oil, rice bran oil, linseed oil, peanut oil, sesame oil, almond oil, cashew oil, canola oil, soybean oil, avocado oil, walnut oil, grape seed oil, sunflower oil, medium chain triglycerides, coconut oil, palm kernel oil, carnauba wax, beeswax, paraffin wax, rice bran wax, candelilla wax, sunflower wax, sugarcane wax, propolis wax, shellac wax, and combinations thereof. In some embodiments, the at least one oil can comprise sunflower oil or medium chain triglycerides. In some embodiments, the at least one oil can comprise sunflower oil. In some embodiments, the at least one oil can comprise medium chain triglycerides.

[0057] Typically, in certain embodiments, the caffeine-tannic acid complex may be contained within the dispersed oil phase of the emulsion. In certain embodiments, the oil phase may comprise about 5% to about 50% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the oil phase may comprise about 10% to about 45% by weight of the complex. In some embodiments, the oil phase may comprise about 15% to about 40% by weight of the complex. In some embodiments, the oil phase may comprise about 20% to about 35% by weight of the complex. In some embodiments, the oil phase may comprise about 25% to about 35% by weight of the complex comprising caffeine and tannic acid. In some embodiments, the oil phase is about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, 20%, about 21%, about 22%, about 23%, about 24%, about 25%, about 26%, about 27%, about 28%, about 29%, about 30%, about 31%, about 32%, about 33%, about 34%, about 35%, about 36%, about 37%, about 38%, about 39%, about 40%, about 41%, about 42%, about 43%, about 44%, about 45%, about 46%, about 47%, about 48%, about 49%, about 50%, about 51%, about 52%, about 53%, about 54%, about 55%, about 56%, about 57%, about 58%, about 59%, about 60%, about 61%, about 62%, about 63%, about 64%, about 65%, about 66%, about 67%, about 68%, about 69%, about 70%, about 71%, about 72%, about 73%, about 74%, about 75%, about 76%, about 77%, about 78%, about 79%, about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, about 99%, about 100%, about 101%, about 102%, about 103%, about 104%, about 10 %, about 30% by weight, about 31% by weight, about 32% by weight, about 33% by weight, about 34% by weight, about 35% by weight, about 36% by weight, about 37% by weight, about 38% by weight, about 39% by weight, about 40% by weight, about 41% by weight, about 42% by weight, about 43% by weight, about 44% by weight, about 45% by weight, about 46% by weight, about 46% by weight, about 48% by weight, about 49% by weight, or about 50% by weight of a complex comprising caffeine and tannic acid.

[0058] The emulsions described herein may further comprise one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.002% to about 8% by weight of one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.002% to about 6% by weight of one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.002% to about 4% by weight of one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.002% to about 2% by weight of one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.003% to about 1.5% by weight of one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.005% to about 1% by weight of one or more stabilizers. In some embodiments, the emulsions may comprise from about 0.01% to about 0.9% by weight of one or more stabilizers. In some embodiments, the emulsion can include from about 0.05% to about 0.8% by weight of one or more stabilizers. In some embodiments, the emulsion can include from about 0.1% to about 0.8% by weight of one or more stabilizers. In some embodiments, the emulsion can include from about 0.2% to about 0.7% by weight of one or more stabilizers. In some embodiments, the emulsion can include from about 0.3% to about 0.6% by weight of one or more stabilizers. In some embodiments, the emulsion comprises about 0.002%, about 0.003%, about 0.004%, about 0.005%, about 0.01%, about 0.05%, about 0.1%, about 0.15%, about 0.2%, about 0.25%, about 0.3%, about 0.35%, about 0.4%, about 0.45%, about 0.5%, about 0.55%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, about 25%, about 26%, about 27%, about 28%, about 29%, about 30%, about 31%, about 32%, about 33%, about 34%, about 35%, about 36%, about 37%, about 38%, about 39%, about 40%, about 41%, about 42%, about 43%, about 44%, about 45%, about 46%, about 47%, about 48%, about 49%, about 50%, about 51%, about 52%, about 53%, about 54%, about 55%, about 55%, about 55%, about 56%, about 57%, about 58%, about 59%, about 60%, about 61%, about 62%, about 63%, about 64%, about 65%, about 65%, about 66%, about 67%, about 68%, about 69 ... %, about 0.6%, about 0.65%, about 0.7%, about 0.75%, about 0.8%, about 0.85%, about 0.9%, about 1%, about 1.2%, about 1.4%, about 1.6%, about 1.8%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, or about 8% by weight of one or more stabilizers.

[0059] In some embodiments, the oil phase of the emulsion can include one or more stabilizers. In certain embodiments, the oil phase can include from about 0.1% to about 30% by weight of one or more stabilizers. In some embodiments, the oil phase can include from about 0.1% to about 25% by weight of one or more stabilizers. In some embodiments, the oil phase can include from about 0.1% to about 20% by weight of one or more stabilizers. In certain embodiments, the oil phase can include from about 0.1% to about 10% by weight of one or more stabilizers. In some embodiments, the oil phase can include from about 0.2% to about 9% by weight of one or more stabilizers. In some embodiments, the oil phase can include from about 0.5% to about 8% by weight of one or more stabilizers. In some embodiments, the oil phase can include from about 1% to about 8% by weight of one or more stabilizers. In some embodiments, the oil phase can comprise about 0.1%, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 12%, about 15%, about 20%, about 25%, or about 30% by weight of one or more stabilizers.

[0060] In some embodiments, the one or more stabilizers may be selected from the group consisting of sorbitan trioleate, stearic acid, ethyl cellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof.

[0061] In some embodiments, the one or more stabilizers can include sorbitan trioleate, stearic acid, ethyl cellulose, polyglycerol polyricinoleate, and combinations thereof. In some embodiments, the one or more stabilizers can include sorbitan trioleate. In some embodiments, the one or more stabilizers can include stearic acid. In some embodiments, the one or more stabilizers can include ethyl cellulose. In some embodiments, the one or more stabilizers can include polyglycerol polyricinoleate. In some embodiments, the one or more stabilizers can include a mixture of sorbitan trioleate and stearic acid.

[0062] The emulsions described herein can also include an aqueous phase. In certain aspects, the emulsion can include about 80% to about 98% by weight of the aqueous phase. In some embodiments, the emulsion can include about 85% to about 95% by weight of the aqueous phase. In some embodiments, the emulsion can include about 90% to about 95% by weight of the aqueous phase. In some embodiments, the emulsion can include about 91% to about 94% by weight of the aqueous phase. In some embodiments, the emulsion can include about 92% by weight of the aqueous phase.

[0063] The emulsions described herein may further comprise one or more emulsifiers. In some embodiments, the emulsions may comprise from about 4% to about 40% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 4% to about 30% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 4% to about 20% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 4% to about 15% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 5% to about 14% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 6% to about 13% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 7% to about 12% by weight of one or more emulsifiers. In some embodiments, the emulsions may comprise from about 8% to about 11% by weight of one or more emulsifiers. In some embodiments, the emulsion can comprise about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 20%, about 25%, or about 30% by weight of one or more emulsifiers.

[0064] Typically, the aqueous phase can include one or more emulsifiers. In some embodiments, the emulsion can include about 5% to about 40% by weight of one or more emulsifiers. In some embodiments, the emulsion can include about 5% to about 30% by weight of one or more emulsifiers. In some embodiments, the emulsion can include about 5% to about 20% by weight of one or more emulsifiers. In some embodiments, the emulsion can include about 5% to about 15% by weight of one or more emulsifiers. In some embodiments, the aqueous phase can include about 6% to about 14% by weight of one or more emulsifiers. In some embodiments, the aqueous phase can include about 7% to about 13% by weight of one or more emulsifiers. In some embodiments, the aqueous phase can include about 8% to about 12% by weight of one or more emulsifiers. In some embodiments, the aqueous phase can include about 9% to about 11% by weight of one or more emulsifiers. In some embodiments, the aqueous phase can comprise about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 20%, about 25%, about 30%, about 35%, or about 40% by weight of one or more emulsifiers.

[0065] In some embodiments, the one or more emulsifiers may be selected from the group consisting of agar, carrageenan, gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, one or more protein-derived emulsifiers (e.g., whey protein isolate and / or sodium caseinate), or mixtures thereof. In some embodiments, the one or more emulsifiers may be gum arabic.

[0066] In certain embodiments, the emulsion can comprise: a) about 5% to about 30% by weight of at least one oil, comprising about 20% to about 40% by weight of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 10:1 to about 1:10, optionally comprising about 0.1% to about 10% by weight of one or more stabilizers; and b) an aqueous phase, optionally comprising about 5% to about 15% by weight of one or more stabilizers. In some embodiments, the emulsion comprises: a) about 5% to about 30% by weight of at least one oil selected from the group consisting of ghee, mustard oil, olive oil, rice bran oil, linseed oil, peanut oil, sesame oil, almond oil, cashew oil, canola oil, soybean oil, avocado oil, walnut oil, grape seed oil, sunflower oil, medium chain triglycerides, coconut oil, palm kernel oil, carnauba wax, beeswax, paraffin wax, rice bran wax, candelilla wax, sunflower wax, sugarcane wax, propolis wax, shellac wax, and combinations thereof; , about 20% to about 40% by weight of a complex comprising a caffeine:tannic acid weight / weight ratio of about 10:1 to about 1:10, and optionally about 0.1% to about 10% by weight of one or more stabilizers selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof; and b) an aqueous phase optionally comprising about 5% to about 15% by weight of one or more emulsifiers selected from the group consisting of agar, carrageenan, gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, and combinations thereof.

[0067] In certain embodiments, the emulsion can comprise: a) about 5% to about 10% by weight of at least one oil, comprising about 20% to about 40% by weight of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 10:1 to about 1:10, optionally about 0.1% to about 10% by weight of one or more stabilizers; and b) an aqueous phase, optionally comprising about 5% to about 15% by weight of one or more stabilizers. In some embodiments, the emulsion comprises: a) about 5% to about 10% by weight of at least one oil selected from the group consisting of ghee, mustard oil, olive oil, rice bran oil, linseed oil, peanut oil, sesame oil, almond oil, cashew oil, canola oil, soybean oil, avocado oil, walnut oil, grape seed oil, sunflower oil, medium chain triglycerides, coconut oil, palm kernel oil, carnauba wax, beeswax, paraffin wax, rice bran wax, candelilla wax, sunflower wax, sugarcane wax, propolis wax, shellac wax, and combinations thereof; , about 20% to about 40% by weight of a complex comprising a caffeine:tannic acid weight / weight ratio of about 10:1 to about 1:10, and optionally about 0.1% to about 10% by weight of one or more stabilizers selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof; and b) an aqueous phase optionally comprising about 5% to about 15% by weight of one or more emulsifiers selected from the group consisting of agar, carrageenan, gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, one or more protein derived emulsifiers (e.g., whey protein isolate and / or sodium caseinate), and combinations thereof.

[0068] In certain embodiments, the emulsion can comprise: a) about 6% to about 9% by weight of at least one oil, comprising about 20% to about 40% of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 5:1 to about 1:5, and optionally about 0.2% to about 9% by weight of one or more stabilizers; and b) an aqueous phase, optionally comprising about 8% to about 12% by weight of one or more emulsifiers. In some embodiments, the emulsion comprises: a) about 6% to about 9% by weight of at least one oil selected from the group consisting of ghee, mustard oil, olive oil, rice bran oil, linseed oil, peanut oil, sesame oil, almond oil, cashew oil, canola oil, soybean oil, avocado oil, walnut oil, grape seed oil, sunflower oil, medium chain triglycerides, coconut oil, palm kernel oil, carnauba wax, beeswax, paraffin wax, rice bran wax, candelilla wax, sunflower wax, sugarcane wax, propolis wax, shellac wax, and combinations thereof. and b) at least one oil comprising about 20% to about 40% by weight of a complex comprising a caffeine:tannic acid weight / weight ratio of about 5:1 to about 1:5, and optionally about 0.2% to about 9% by weight of one or more stabilizers selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof; and c) an aqueous phase optionally comprising about 8% to about 12% by weight of one or more emulsifiers selected from the group consisting of agar, carrageenan, gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, one or more protein derived emulsifiers (e.g., whey protein isolate and / or sodium caseinate), and combinations thereof.

[0069] In certain embodiments, the emulsion can include: a) about 8% of at least one oil, comprising about 30% by weight of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 1:3, and comprising about 0.2% by weight to about 9% by weight of one or more stabilizers; and b) an aqueous phase comprising about 10% by weight of one or more emulsifiers. In some embodiments, the emulsion can include: a) about 8% by weight of at least one oil selected from the group consisting of sunflower oil, medium chain triglycerides, and carnauba wax, comprising about 30% by weight of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 1:3, and comprising about 0.2% by weight to about 9% by weight of one or more stabilizers selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, and combinations thereof; and b) an aqueous phase comprising 10% by weight of gum arabic.

[0070] In certain embodiments, the emulsion can include: a) about 8% of at least one oil, comprising about 30% by weight of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 1:1, and comprising about 0.2% to about 9% by weight of one or more stabilizers; and b) an aqueous phase comprising about 10% by weight of one or more emulsifiers. In some embodiments, the emulsion can include: a) about 8% by weight of at least one oil selected from the group consisting of sunflower oil, medium chain triglycerides, and carnauba wax, comprising about 30% by weight of a complex comprising caffeine:tannic acid in a weight / weight ratio of about 1:1, and comprising about 0.2% to about 9% by weight of one or more stabilizers selected from the group consisting of sorbitan trioleate, stearic acid, ethylcellulose, polyglycerol polyricinoleate, and combinations thereof; and b) an aqueous phase comprising 10% by weight of gum arabic.

[0071] process In certain embodiments, the caffeine-tannic acid complex can be prepared by adding a solution of tannic acid in water at an appropriate concentration to a solution of caffeine in water at an appropriate concentration while mixing under high shear conditions to form a precipitate, and then isolating, drying, and grinding the precipitate. Typically, the amount of tannic acid added to water is based on its solubility at a given temperature such that the entire amount of tannic acid is soluble in the amount of water used. In some embodiments, tannic acid can be added to water at room temperature. In some embodiments, tannic acid can be added to water at about 60°C. Similarly, the amount of caffeine initially added to water is based on its solubility at a given temperature such that the entire amount of caffeine is soluble in the amount of water used. In some embodiments, caffeine can be added to water at room temperature. In some embodiments, caffeine can be added to water at about 60°C.

[0072] In some embodiments, the caffeine-tannic acid complex can be prepared by adding an appropriate amount of tannic acid and an appropriate amount of caffeine to absolute ethanol or ethanol containing 0.1% to 60% w / w water, stirring until a solution is formed, and then spray drying the resulting solution. In some embodiments, the ethanol can include about 0.5% to about 55% w / w water. In some embodiments, the ethanol can include about 1% to about 50% w / w water. In some embodiments, the ethanol can include about 2% to about 40% w / w water. In some embodiments, the ethanol can include about 3% to about 30% w / w water. In some embodiments, the ethanol can include about 4% to about 20% w / w water. In some embodiments, the ethanol can comprise about 0.1%, about 0.5%, about 1%, about 2%, about 3%, about 4%, 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%, or about 80% w / w of water.

[0073] In certain embodiments, for the purpose of preparing the emulsion described herein, the precipitate can be ground into a small powder and passed through a sieve. In certain embodiments, the sieve used can be a 40 mesh sieve. In some embodiments, the resulting powder can be passed through a jet mill before preparing the emulsion.

[0074] In some embodiments, the emulsions provided herein can be prepared by adding a caffeine-tannic acid complex to at least one oil. In some embodiments, if the oil phase includes a stabilizer, the stabilizer can be added to the mixture of the oil and the caffeine-tannic acid complex. In some embodiments, the oil, stabilizer, and complex can be combined in a grinding chamber, and the resulting mixture can be further processed with non-reactive grinding balls, such as zirconium oxide grinding balls. In some embodiments, the grinding balls can be about 2 mm in diameter, although balls of other diameters can be used as appropriate. In some embodiments, the grinding balls can be about 0.5 mm, about 1 mm, or about 2 mm in diameter. In some embodiments, the mixture can be ground in the chamber for about 1 to about 50 hours. In some embodiments, the mixture can be ground in the chamber for about 1 to about 24 hours. In some embodiments, the mixture can be ground in the chamber for about 1 to about 20 hours. In some embodiments, the mixture can be ground in the chamber for about 1 to about 15 hours. In some embodiments, the mixture can be ground in the chamber for about 1 to about 10 hours. In some embodiments, the mixture can be ground in the chamber for about 1 to about 8 hours. In some embodiments, the mixture can be milled in the chamber for about 1 to about 6 hours. In some embodiments, the mixture can be milled in the chamber for about 1 to about 4 hours. In some embodiments, the mixture can be milled in the chamber for about 24 to about 50 hours. In some embodiments, the mixture can be milled in the chamber for about 30 to about 45 hours. In some embodiments, the mixture can be milled in the chamber for about 35 to about 40 hours. In some embodiments, the mixture can be milled at about 500 to about 2000 rpm. In some embodiments, the mixture can be milled at about 500 to about 1500 rpm. In some embodiments, the mixture can be milled at about 750 to about 1250 rpm. In some embodiments, the mixture can be milled at about 900 to about 1100 rpm. In some embodiments, the mixture can be milled at about 1000 rpm.In some embodiments, the mixture can be ground in the chamber at a temperature of about 15° C. to about 90° C. In some embodiments, the mixture can be ground in the chamber at a temperature of about 15° C. to about 75° C. In some embodiments, the mixture can be ground in the chamber at a temperature of about 15° C. to about 60° C. In some embodiments, the mixture can be ground in the chamber at a temperature of about 15° C. to about 50° C. In some embodiments, the mixture can be ground in the chamber at a temperature of about 18° C. to about 35° C. In some embodiments, the mixture can be ground in the chamber at a temperature of about 20° C. to about 30° C. Typically, in some embodiments, the resulting slurry can be separated from the grinding balls.

[0075] In certain embodiments where the emulsion includes an emulsifier, the emulsifier can be added to the aqueous phase prior to emulsification. In some embodiments, the aqueous phase can be prepared by slowly adding one or more emulsifiers to warm water. In some embodiments, the water can be heated to a temperature of about 40° C. to about 60° C. In some embodiments, the water can be heated to a temperature of about 50° C. In some embodiments, the mixture can be cooled after addition.

[0076] In some embodiments, the resulting oil and water phases can be combined and emulsified. In certain embodiments, the oil phase can be added to the water phase. In other embodiments, the water phase can be added to the oil phase. In certain embodiments, the oil and water phases can be combined simultaneously at the same speed or at different speeds. In some embodiments, the combined oil and water phases can be mixed under high speed. In some embodiments, the combined oil and water phases can be mixed in a high shear mixer. In some embodiments, the combined oil and water phases can be mixed at about 10,000 to about 30,000 rpm. In some embodiments, the combined oil and water phases can be mixed at about 15,000 to about 25,000 rpm. In some embodiments, the combined oil and water phases can be mixed at about 20,000 rpm. In some embodiments, the combined oil and water phases can be mixed for about 30 seconds to about 5 minutes. In some embodiments, the combined oil and water phases can be mixed for about 1 minute.

[0077] beverage The present disclosure also provides beverage syrups and beverages comprising the emulsions disclosed herein. For example, in some embodiments, the beverage can contain one or more of the emulsions described herein in a volume sufficient to provide a caffeine concentration in the beverage of about 50 ppm to about 900 ppm. In some embodiments, the caffeine concentration in the beverage can be about 75 ppm to about 850 ppm, about 100 ppm to about 800 ppm, about 125 ppm to about 750 ppm, about 150 ppm to about 700 ppm, about 175 ppm to about 650 ppm, about 200 ppm to about 550 ppm of caffeine, or about 225 ppm to about 500 ppm. In some embodiments, the caffeine concentration in the beverage can be about 50 ppm, about 75 ppm, about 100 ppm, about 125 ppm, about 150 ppm, about 175 ppm, about 200 ppm, about 225 ppm, about 250 ppm, about 275 ppm, about 300 ppm, about 325 ppm, about 350 ppm, about 375 ppm, about 400 ppm, about 425 ppm, about 450 ppm, about 475 ppm, about 500 ppm, about 525 ppm, about 550 ppm, about 575 ppm, about 600 ppm, about 625 ppm, about 650 ppm, about 675 ppm, about 700 ppm, about 725 ppm, about 750 ppm, about 775 ppm, or about 800 ppm. In some embodiments, the concentration of caffeine in the beverage may be about 400 ppm.

[0078] In certain embodiments, a portion of the caffeine remains bound to tannic acid for about 30 minutes to about 180 minutes after the beverage is consumed. In some embodiments, a portion of the caffeine remains bound to tannic acid for about 45 minutes to about 150 minutes, or about 60 minutes to about 120 minutes after the beverage is consumed. In some embodiments, a portion of the caffeine remains bound to tannic acid for about 30 minutes, about 40 minutes, about 50 minutes, about 60 minutes, about 70 minutes, about 80 minutes, about 90 minutes, about 100 minutes, about 120 minutes, about 130 minutes, about 140 minutes, about 150 minutes, about 160 minutes, about 170 minutes, or about 180 minutes after the beverage is consumed.

[0079] In certain embodiments, 90 minutes after the beverage is consumed, the percentage of caffeine bound to tannic acid may be about 50% to about 99%. In some embodiments, the percentage of caffeine bound to tannic acid may be about 65% to about 95%, about 70% to about 90%, or about 75% to about 85%. In some embodiments, 90 minutes after the beverage is consumed, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 99% of the caffeine is bound to tannic acid.

[0080] In certain embodiments, the beverage can be a carbonated or non-carbonated soft drink, a fountain drink, a frozen ready-to-drink beverage, coffee, tea or other brewed beverage, a dairy beverage, a flavored water, an enhanced water, a juice such as fruit juice (including diluted and ready-to-drink concentrated juices), a fruit juice flavored drink, an enhanced beverage such as a sports drink, a smoothie, an energy drink, or an alcoholic beverage. In certain embodiments, the beverage can be a carbonated soft drink. In some embodiments, the beverage can be a caffeinated water.

[0081] In certain embodiments, the beverage may include one or more sweeteners, including low-calorie carbohydrate sweeteners, natural high-potency sweeteners, synthetic high-potency sweeteners, other sweeteners, and combinations thereof.

[0082] Examples of suitable low calorie carbohydrate sweeteners include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, D-tagatose, trehalose, galactose, rhamnose, cyclodextrins (e.g., α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose, or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, gluco Examples of such sugars include no-lactone, abequose, galactosamine, xylo-oligosaccharides (xylotriose, xylobiose, etc.), gentio-oligoscaccharides (gentio-oligoscaccharides) (gentio-biose, gentiotriose, gentiotetraose, etc.), galactooligosaccharides, sorbose, nigero-oligosaccharides, fructooligosaccharides (kestose, nystose, etc.), maltotetraol, maltotriol, maltooligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, etc.), lactulose, melibiose, raffinose, rhamnose, ribose, isomerized liquid sugars such as high fructose corn / starch syrup (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, and glucose syrup.

[0083] As used herein, the phrase "natural high intensity sweeteners" includes rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, rebaudioside R, rebaudioside S, rebaudioside T, rebaudioside U, rebaudioside V, dulcoside A, rubusoside, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo (Luo Han Guo sweetener, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobtain, bayounoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, and cyclocaryoside I.

[0084] Natural high-potency sweeteners also include modified natural high-potency sweeteners. Modified natural high-potency sweeteners include natural high-potency sweeteners that have been modified naturally. For example, modified natural high-potency sweeteners include, but are not limited to, natural high-potency sweeteners that have been fermented, contacted with enzymes, derivatized, or substituted. In one embodiment, at least one modified natural high-potency sweetener can be used in combination with at least one natural high-potency sweetener. In another embodiment, at least one modified natural high-potency sweetener can be used without a natural high-potency sweetener. Modified natural high-potency sweeteners can be used in place of natural high-potency sweeteners or in combination with natural high-potency sweeteners for any of the embodiments described herein.

[0085] As used herein, the phrase "synthetic sweetener" refers to any composition that is not found in nature and is a high-intensity sweetener.Non-limiting examples of synthetic sweetener suitable for the present invention include, but are not limited to, sucralose, acesulfame potassium, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-La-aspartyl]-L-phenylalanine 1-methyl ester, N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-La-aspartyl]-L-phenylalanine 1-methyl ester, N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-La-aspartyl]-L-phenylalanine 1-methyl ester, and their salts (as appropriate), and their combinations.

[0086] Carbon dioxide can be used to provide effervescence in certain embodiments of the beverages disclosed herein. Any of the techniques and carbonation devices known in the art for carbonating beverages can be used. Carbon dioxide can improve the taste and appearance of the beverage and can help protect the purity of the beverage by inhibiting and / or destroying undesirable bacteria. In certain embodiments, for example, the beverage can have a CO2 level of up to about 4.0 volumes of carbon dioxide. In other embodiments, for example, the beverage can have about 0.5 to 5.0 volumes of carbon dioxide. As used herein, one volume of carbon dioxide refers to the amount of carbon dioxide absorbed by a given amount of a given liquid, such as water at 60°F (16°C) and 1 atmosphere pressure. The volume of gas occupies the same space as the liquid in which it is dissolved. The carbon dioxide content can be selected by one of skill in the art based on the level of effervescence desired and the effect of carbon dioxide on the taste or mouthfeel of the beverage.

[0087] In some embodiments, the beverage may further include additional ingredients, including any of those typically found in beverage compositions. Examples of such additional ingredients include, but are not limited to, caramel and other colorants or dyes, foaming or defoaming agents, gums, emulsifiers, tea solids, cloudiness components, and mineral and non-mineral dietary supplements. Examples of non-mineral dietary supplement ingredients are known to those skilled in the art and include, for example, antioxidants and vitamins (such as vitamins A, D, E (tocopherol), C (ascorbic acid), B (thiamine), B2 (riboflavin), B6, B12, and K), niacin, folic acid, biotin, and combinations thereof. Optional non-mineral dietary supplements are typically present in amounts generally accepted under good manufacturing practice. Exemplary amounts may be from about 1% to about 100% of the Recommended Daily Value (RDV), where RDVs have been established. In certain exemplary embodiments, the non-mineral dietary supplement ingredient(s) may be present in an amount of about 5% to about 20% of the RDV, where established.

[0088] In certain embodiments, the beverage may also include one or more preservatives. Solutions with a pH of less than 4 (especially those with a pH of less than 3) are typically "micro-stable", i.e., resistant to microbial growth and suitable for long-term storage prior to consumption without the need for additional preservatives. However, additional preservative systems may be used if desired. As used herein, the term "preservative system" or "preservative" includes any suitable preservative approved for use in beverage compositions, including, but not limited to, known chemical preservatives such as benzoates (such as sodium benzoate, calcium benzoate, and potassium benzoate), sorbates (such as sodium sorbate, calcium sorbate, and potassium sorbate), citrates (such as sodium citrate and potassium citrate), polyphosphates (such as sodium hexametaphosphate (SHMP)), and mixtures thereof, as well as antioxidants such as ascorbic acid, EDTA, BHA, BHT, TBHQ, dehydroacetic acid, dimethyl dicarbonate, ethoxyquin, heptylparaben, and combinations thereof. Preservatives may be used in amounts not exceeding the maximum concentrations mandated under applicable laws and regulations. In some embodiments, the beverage may include potassium sorbate.

[0089] In certain embodiments, the beverage may include an antioxidant selected from the group consisting of rutin, quercetin, flavonone, flavone, dihydroflavonol, flavonol, flavandiol, leucoanthocyanidin, flavanol glycoside, flavonone glycoside, isoflavonoid, and neoflavonoid. In particular, flavonoids include, but are not limited to, quercetin, eriocitrin, neoeriocitrin, narirutin, naringin, hesperidin, hesperetin, neohesperidin, neoponcirin, poncirin, rutin, isorhoifolin, rhoifolin, diosmin, neodiosmin, sinensetin, nobiletin, tangeritin, catechin, catechin gallate, epigallocatechin, epigallocatechin gallate, oolong tea polymerized polyphenol, anthocyanin, heptamethoxyflavone, daidzin, daphne ... It can be isein, biochanin A, prunetin, genistin, glycitein, glycitin, genistein, 6,7,4' trihydroxyisoflavone, morin, apigenin, vitexin, vulcarein, apiin, cupresflavone, dathistin, diosmetin, fisetin, galangin, gossypetin, geraldol, hinokiflavone, primuletin, pratol, luteolin, myricetin, orientin, robinetin, quercetagetin, and hydroxy-4-flavone.

[0090] The beverages described herein may also optionally include one or more suitable food-grade acids. Exemplary acids include water-soluble organic acids and their salts, including, but not limited to, phosphoric acid, sorbic acid, ascorbic acid, benzoic acid, citric acid, tartaric acid, propionic acid, butyric acid, acetic acid, succinic acid, glutaric acid, maleic acid, malic acid, valeric acid, caproic acid, malonic acid, aconitic acid, potassium sorbate, sodium benzoate, sodium citrate, amino acids, and any combination thereof. In certain embodiments, the beverage includes malic acid and / or phosphoric acid.

[0091] In some embodiments, the emulsion can be used to prepare a beverage. In some embodiments, the emulsion can be added to a beverage syrup that can be diluted to provide a beverage. In some embodiments, the emulsion can be added to a pre-prepared beverage.

[0092] The embodiments described herein are further described with reference to the following examples. These examples are for illustrative purposes only, and the embodiments described herein should not be construed as being limited to these examples. Rather, the embodiments should be construed as embracing any and all variations that become evident as a result of the teachings provided herein. EXAMPLES

[0093] Example 1A: General procedure for preparing caffeine-tannic acid complex Tannic acid was added to water and stirred until completely dissolved. In a separate vessel, caffeine was added to water and stirred until completely dissolved. The caffeine solution (1.5% w / w in water) was placed under shear at 3000 rpm and treated with tannic acid solution (either 1 or 3 equivalents of 1.5% w / w tannic acid solution depending on the complex formed) at a rate of 200 g / min. For analytical purposes, the mixture was allowed to equilibrate overnight and analysis was carried out using the procedure described in Example 2.

[0094] To isolate the solid complex, the precipitate was collected by filtration, dried, hand ground, and then passed through a 40 mesh sieve. The resulting powder was optionally passed through a jet mill (Fluid Energy Processing and Equipment Company, Model 00 Jet-O-Mizer system) according to the manufacturing procedure specified by.

[0095] Example 1B: Preparation of caffeine-tannic acid complex using spray drying A mixture of 150 g tannic acid, 50 g caffeine, and 800 g aqueous ethanol containing 5% w / w water was gently stirred until the solution became clear. The solution was spray dried to obtain a caffeine-tannic acid complex, while maintaining the evaporation temperature below 178° C. to avoid caffeine sublimation.

[0096] Example 1C: Alternative preparation of caffeine-tannic acid complex using spray drying A mixture of 150 g tannic acid, 100 g caffeine, 650 g aqueous ethanol (5% w / w), and 100 g water was gently stirred until the solution was clear. The solution was spray dried to obtain a caffeine-tannic acid complex, while maintaining the evaporation temperature below 178° C. to avoid caffeine sublimation.

[0097] Example 2: Procedure for analyzing caffeine-tannic acid complexes using centrifugation A sample of the aqueous caffeine-tannic acid mixture prepared in Example 1 was pipetted into the sample holder of a centrifuge tube with 1) a 1K molecular weight cut-off membrane (to remove any water-soluble components with a molecular weight less than 1 kDa, such as free caffeine). The tube was centrifuged at 5,300 rpm for 30 minutes (Beckman Coulter Life Science Avanti JE Rotor: JS5.3 swinging bucket rotor) to filter the sample through the cut-off membrane. The filtrate was prepared for ultra-performance liquid chromatography to analyze the amount of free caffeine. The free caffeine content in the filtrate from the 3:1 complex preparation was determined to be 230 ppm. The free caffeine content in the filtrate from the 1:1 complex preparation was determined to be 1300 ppm.

[0098] Samples of the 1:1 wt / wt caffeine:tannic acid and 1:3 wt / wt caffeine:tannic acid complexes were analyzed by FT IR and compared to uncomplexed mixtures of the same ratios of reagents. As shown in Figures 1A, 1B, 2A, 2B, and 3, the FT IR spectra of the complexes differ from those of the mixed reagents, further confirming that caffeine and tannic acid are associated within the complex.

[0099] Example 3: Procedure for determining the release rate of caffeine from tannic acid complexes using dialysis Each caffeine-tannic acid complex (0.2 g) was added to 9.8 g of water and placed in a dialysis bag, which was sealed on both sides. The bag was placed in a beaker containing 90 g of water and gently stirred. At each sampling time, an aliquot was taken from the water outside the dialysis bag and filtered through a 0.1 μm filter. The caffeine content of the resulting filtrate was analyzed by HPLC. As shown in Figure 4, all caffeine-tannic acid complexes delayed the release of caffeine.

[0100] Example 4: General procedure for preparing caffeine-tannic acid-additional acid complex Caffeine (1 g) was added to water (99 g) and stirred until all solids were dissolved. Tannic acid (2 g) and additional acid (oxalic acid, malonic acid, maleic acid, or citric acid, 3 g) were added to 95 g of water and the mixture was stirred until all solids were dissolved. The resulting tannic acid solution was slowly added to the aqueous caffeine solution and the resulting mixture was stirred for 5 minutes before being centrifuged to collect the precipitate. Caffeine release was determined by dialysis as described in Example 5.

[0101] Example 5: Procedure for determining the release rate of caffeine from caffeine-tannic acid complexes using dialysis Each conjugate from Example 4 (0.2 g) and water (9.8 g) were added to a dialysis bag, which was then sealed at each end. The bag was placed in 90 g of water. At each sampling time, an aliquot was removed from the water outside the dialysis bag and filtered through a 0.1 μm filter. The caffeine content of the resulting filtrate was analyzed by HPLC. The results are shown in Figure 5. All conjugates provided a delayed release of caffeine compared to unconjugated caffeine.

[0102] Example 6: Procedure for preparing caffeine-tannic acid-dopamine complex Caffeine (1 g) was added to water (99 g) and stirred until all solids were dissolved. Tannic acid (2 g or 3 g) and dopamine (3 g) were added to 95 g of water and the mixture was stirred until all solids were dissolved. This solution was slowly added to the aqueous caffeine solution and the resulting mixture was stirred for 5 minutes and then centrifuged to collect the precipitate. Caffeine release was determined by dialysis. Each complex (0.2 g) and water (9.8 g) were added to a dialysis bag and each end was sealed. The bag was placed in 90 g of water. After 30 minutes, an aliquot was removed from the water outside the dialysis bag and filtered through a 0.1 μm filter. The caffeine content of the resulting filtrate was analyzed by HPLC. Samples were taken for analysis every 30 minutes for 2 hours and then every hour for an additional 5 hours. As shown in Figure 6, the complexes provided a delayed release of caffeine compared to free caffeine.

[0103] Example 7: General procedure for preparing caffeine-tannic acid emulsion The caffeine-tannic acid complex from Example 1 was dried, hand ground, and then passed through a 40 mesh sieve. The resulting powder was optionally passed through a jet mill (Fluid Energy Processing and Equipment Company, Model 00 Jet-O-Mizer system) according to the specified manufacturing procedure.

[0104] Stabilizer (polyglycerol polyricinoleate (PGPR)), sorbitan trioleate (Span® 85), sorbitan oleate (Span® 80), or ethylcellulose (Ethocel®), 1.68 g) was dissolved in oil (sunflower or medium chain triglycerides (MCT), 19.32 g) and combined with the jet-milled composite powder (9 g) in the milling chamber, treated with zirconium oxide milling balls (ball diameter 2 mm, 60 mL) and gently stirred. The milling chamber was sealed and milled in a ball mill (E-Max 220V) for 39 h at 1000 rpm and a temperature of 20 °C to 30 °C. The resulting slurry was separated from the milling balls using a vacuum flask and a mesh screen.

[0105] Deionized water (900 g) was heated to 50° C. and slowly treated with 100 g of gum arabic powder, then cooled to room temperature. The oil slurry (4 g) was added to the gum arabic solution (46 g) with stirring to ensure that the oil phase minimally stuck to the equipment and container. Once combined, the mixture was placed in a high shear mixer and combined at 20,000 rpm for 1 minute to prepare an emulsion containing 92% water phase (i.e., 10% gum arabic solution) and 8% oil phase (i.e., 8% polyglycerol polyricinoleate (PGPR) in sunflower oil, 30% complex loading; ball mill slurry). Net caffeine content: 0.6% w / w. The particle size of the emulsion was determined using a Horiba LA-950 particle size analyzer according to the manufacturer's instructions. The caffeine release profile of the emulsion was determined using the centrifugation method of Example 9 or the dialysis procedure described in Example 8.

[0106] Example 8: Procedure for determining the release rate of caffeine from emulsions using dialysis A solution of 1% caffeine in pH 3.0 buffer was added to 570 g of pH 3.0 buffer to give a 100 ppm free caffeine solution. A dialysis bag was prepared using reverse osmosis water. Excess water was removed and the bottom of the bag was folded over and clamped. The emulsion (30 g) was added to the dialysis bag and the top of the bag was folded over and clamped. A small stir bar was added to the beaker containing the caffeine spiked buffer and the dialysis bag was added to the beaker. The beaker was placed on a stir plate and stirred slowly (<100 rpm). After 5 minutes, a sample of the water outside the bag was taken into a syringe fitted with a 0.1 μm filter. The sample was slowly filtered into a glass vial and the filtrate was analyzed by ultra-performance liquid chromatography to analyze the free caffeine. Parafilm® was placed on top of the system to seal and prevent evaporation. The systems were sampled again after 1, 4, 7 and 12 days, and then optionally once a week for up to about 6 months shelf life of the emulsion.

[0107] Table 2 shows the emulsions prepared and analyzed under dialysis conditions. All emulsions contained a 92:8 wt / wt ratio of aqueous phase:oil phase, with 15% gum arabic in the aqueous phase, unless otherwise noted. The amount of free and encapsulated caffeine over time for representative examples is shown in Figures 14A-16. As shown in Figures 14A, 14B, 15A, 15B, and 16, both MCT and sunflower oil provided stable levels of encapsulated caffeine over time. [Table 1-1] [Table 1-2]

[0108] Example 9: Procedure for determining the release rate of caffeine from emulsions using centrifugation In a typical experiment, 10 g of emulsion was mixed with 140 g of pH 3 buffer. At the designed sampling time, an aliquot was removed and loaded into a centrifuge tube with a 1K molecular weight cutoff. The tube was centrifuged at 5,300 rpm for 30 minutes to filter the sample through the cutoff membrane. The amount of free and encapsulated caffeine measured over time for the emulsions shown in Table 3 are shown in Figures 7A-13B. As shown in each figure, the percentage of encapsulated caffeine (or the amount of free caffeine) remains stable over time. [Table 2]

[0109] Example 10: Preparation of Representative Beverages The ingredients shown below were combined to form a citrate buffer solution. [Table 3]

[0110] Representative beverages were prepared by diluting the 8% PGPR emulsions listed in Table 3 15-fold with citrate buffer (pH 3) to yield a caffeine concentration of 400 ppm.

[0111] Example 11: Determination of caffeine release profiles of representative beverages using a gastric model Citrate buffer (pH 3, 60 mL), gastric mucin solution (prepared from 1.5 g gastric mucin in 50 mL water, 21.5 mL of solution was used), and pepsin (0.2% solution, 21.5 mL) were combined and equilibrated to 37° C. in a water bath for at least 30 minutes. After the equilibration period, a representative drink was added and a sample was taken to represent T=0, and 1.5 N HCl was pumped in at a rate of 0.25 mL / min. HCl was added until 30.0 mL had been added or until pH=<1.8. Samples were taken every 30 minutes. After pH=<1.8 (approximately the 2 hour mark), the pump was stopped. 5 N NaOH, NaHCO3, pancreatin, and bile salts were added to simulate a shift to the upper intestine. The mixture was stirred for 3 hours and sampled every 30 minutes using the centrifugation method described in Example 9. The results are shown in FIG. 17. As shown in the graph, the release of caffeine from the beverage was delayed until the beverage reached the small intestine portion of the model. Note that the T=0 measurement indicates that there was an initial release of caffeine upon any dilution or addition of the sample to the model.

[0112] These results demonstrate that the addition of the caffeine complexes and emulsions described herein to a beverage can delay the release of caffeine after the beverage has been consumed, eliminating the jitteriness and "caffeine crash" that can be associated with consuming these beverages.

[0113] The breadth and scope of the present disclosure should not be limited by any of the above-described exemplary embodiments, but should be defined only in accordance with the following claims and their equivalents.

[0114] All patents, patent applications, and other references mentioned or referenced in this application are incorporated herein by reference in their entirety.

Claims

1. A complex containing caffeine and tannic acid.

2. The complex according to claim 1, wherein caffeine and tannic acid are present in the complex in a weight / weight ratio of about 10:1 to about 1:

10.

3. The complex according to claim 1, wherein caffeine and tannic acid are present in the complex in a weight / weight ratio of about 5:1 to about 1:

5.

4. The complex according to claim 1, wherein caffeine and tannic acid are present in the complex in a weight / weight ratio of about 4:1 to about 1:

4.

5. The complex according to claim 1, containing about 23 wt% to about 35 wt% of caffeine.

6. The complex according to claim 1, containing about 35 wt% to about 53 wt% of caffeine.

7. The complex according to claim 1, further comprising an additional compound selected from the group consisting of citric acid, dopamine, maleic acid, malonic acid, and oxalic acid.

8. a. An oil phase containing at least one oil containing the complex according to claim 1, b. An aqueous phase containing water, An emulsion comprising.

9. The emulsion according to claim 8, further comprising one or more stabilizers.

10. The emulsion according to claim 8, further comprising one or more emulsifiers.

11. The emulsion according to claim 8, wherein the emulsion contains about 2 wt% to about 30 wt% of the at least one oil.

12. The emulsion according to claim 8, wherein the emulsion contains about 5 wt% to about 10 wt% of the at least one oil.

13. The emulsion according to claim 8, wherein the at least one oil is selected from the group consisting of one or more edible oils, one or more edible waxes, and combinations thereof.

14. The emulsion according to claim 8, wherein the at least one oil is selected from the group consisting of ghee, mustard oil, olive oil, rice bran oil, linseed oil, peanut oil, sesame oil, almond oil, cashew oil, canola oil, soybean oil, avocado oil, walnut oil, grape seed oil, sunflower oil, medium-chain triglycerides, coconut oil, palm kernel oil, carnauba wax, beeswax, paraffin wax, rice bran wax, candelilla wax, sunflower wax, sugarcane wax, propolis wax, shellac wax, and combinations thereof.

15. The emulsion according to claim 8, wherein the at least one oil is selected from the group consisting of sunflower oil and medium-chain triglycerides.

16. The emulsion according to claim 8, comprising from about 0.1% to about 15% by weight of said complex.

17. The emulsion according to claim 8, comprising from about 1% to about 4% by weight of said complex.

18. The emulsion according to claim 9, wherein said emulsion comprises from about 0.002% to about 8% by weight of said one or more stabilizers.

19. The emulsion according to claim 9, wherein said emulsion comprises from about 0.08% to about 1.2% by weight of said one or more stabilizers.

20. The emulsion according to claim 9, wherein said one or more stabilizers are selected from the group consisting of sorbitan trioleate, stearic acid, ethyl cellulose, polyglycerol polyricinoleate, sucrose, and combinations thereof.

21. The emulsion according to claim 9, wherein said one or more stabilizers are selected from the group consisting of sorbitan trioleate, stearic acid, ethyl cellulose, polyglycerol polyricinoleate, and combinations thereof.

22. The emulsion according to claim 10, comprising from about 4% to about 40% by weight of said one or more emulsifiers.

23. The emulsion according to claim 10, comprising about 10% by weight of said one or more emulsifiers.

24. The emulsion according to claim 10, wherein said one or more emulsifiers are selected from the group consisting of agar, carrageenan, gellan, gelatin, guar gum, sodium alginate, xanthan gum, gum arabic, Quillaja saponaria saponin, and combinations thereof.

25. The emulsion according to claim 10, wherein said one or more emulsifiers is gum arabic.

26. A process for preparing the complex according to claim 1, comprising adding tannic acid and caffeine to absolute ethanol or aqueous ethanol, and spray-drying the resulting solution.

27. A process for preparing the complex according to claim 1, comprising adding an aqueous solution of tannic acid to an aqueous solution of caffeine, and filtering the resulting suspension.

28. A process for preparing the emulsion according to claim 8, the process comprising adding a mixture of the complex, at least one oil, and optionally one or more stabilizers to a mixture of water and optionally one or more emulsifiers, and mixing at high speed.

29. A beverage comprising the emulsion according to claim 8.

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