Mogroside Compounds and Uses Thereof

Abstract

The present disclosure generally relates to the compound isomogroside IV E In some embodiments, the present disclosure relates to various formulations and uses of isomogroside IV. E In some embodiments, the compositions are edible compositions, such as, but not limited to, packaged food and beverage products and tabletop sweeteners. In some aspects, the present disclosure provides specific compositions containing such mogroside compounds, such as compositions containing such mogroside compounds and one or more other sweeteners. In other aspects, the present disclosure provides methods for reducing the calorie content of sweetened products, such as sweetened foods or beverages. TIFF2022526205000009.tif73150

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of priority to PCT Application No. PCT / CN2019 / 081409, filed April 4, 2019, which is incorporated by reference herein as if set forth in its entirety.

[0002] Technical Field The present disclosure generally relates to a compound, isomogroside IV, having the formula shown in FIG. 1, also referred to herein as “MC1.” E The present disclosure relates to various formulations and uses of MC1. In some aspects, the disclosure provides compositions containing MC1. In some embodiments, the compositions are edible compositions, such as, but not limited to, packaged food and beverage products and tabletop sweeteners. In some aspects, the disclosure provides specific compositions containing such flavanone derivatives, such as compositions containing such flavanone derivatives and one or more other sweeteners. In some other aspects, the disclosure provides methods for reducing the calorie content of sweetened products, such as sweetened food or beverage products.

[0003] 2. Description of Related Art The gustatory system provides sensory information about the chemical composition of the external world. Taste transduction is one of the more complex forms of chemically triggered sensation in animals. Taste signaling is found throughout the animal kingdom, from simple metazoans to the most complex vertebrates. Mammals are thought to have five basic taste modalities: sweet, bitter, sour, salty, and umami.

[0004] Sweetness is the most commonly perceived taste when eating foods that are high in sugar. Mammals generally perceive sweetness as a pleasant sensation, except when excessive. Caloric sweeteners such as sucrose and fructose are examples of prototypic sweet tastants. Although a variety of non-caloric and low-caloric alternatives exist, these caloric sweeteners remain the primary means by which edible products produce the perception of sweetness when consumed.

[0005] Metabolic disorders and related diseases, such as obesity, diabetes, and cardiovascular disease, are major public health concerns worldwide. And their prevalence has been increasing at an alarming rate in almost all developed countries. Caloric sweeteners are a major driver of this trend, as they are included in various packaged food and beverage items to make them more palatable to consumers. In many cases, non-caloric or low-caloric substitutes can be used in place of sucrose and fructose in foods and beverages. Even so, these compounds impart a different sweetness to caloric sweeteners, and many consumers do not consider them suitable replacements. Furthermore, such compounds can be difficult to formulate into certain products. In some cases, they are used as partial replacements for caloric sweeteners, but their mere presence can cause many consumers to perceive unpleasant off-tastes, such as astringent, bitter, metallic, and licorice flavors. As such, currently available low-calorie sweeteners face certain challenges in their adoption. Thus, there is a continuing need to discover and develop non-caloric or low-caloric sweeteners that may be more acceptable to consumers.

[0006] Summary of the Invention The present disclosure relates to isomogroside IV, also referred to herein as "MC1." E This relates to the discovery of a compound having the following chemical structure: [ka] and impart certain beneficial taste characteristics when used in combination with other sweeteners and flavor modifying compounds and when formulated in certain solid forms.

[0007] In a first aspect, the present disclosure provides isomogroside IV E to provide.

[0008] In a second aspect, the disclosure provides solid forms, such as crystalline polymorphs, co-crystals, and solvates, of the compounds of the first aspect.

[0009] In a third aspect, the disclosure provides formulations of the compounds of the first aspect or the solid forms of the second aspect for use in edible products such as food and beverages, and in combination with other sweeteners, flavor modifiers, mouthfeel enhancers, and the like.

[0010] In a fourth aspect, the disclosure provides the use of a compound of the first aspect, a solid form of the second aspect, or a formulation of the third aspect for modifying or imparting a flavor, e.g., for imparting sweetness to an edible product, such as a food or beverage product.

[0011] Further aspects, and embodiments thereof, are described in the following detailed description, drawings, abstract, and claims.

[0012] The following drawings are provided for the purpose of illustrating various embodiments of the compositions and methods disclosed herein. The drawings are provided for illustrative purposes only and are not intended to illustrate preferred compositions or preferred methods or to serve as the basis for any limitation on the scope of the invention as recited in the claims. [Brief description of the drawings]

[0013] [Figure 1] This is the chemical formula for the compound isomogroside IVE. [Diagram 2]LC-HR-MS spectrum of (1S,4R,9beta,11alpha,24R)-1-{[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (isomogroside IVE). [Diagram 3] H NMR spectrum of (1S,4R,9beta,11alpha,24R)-1-{[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (isomogroside IVE). [Figure 4] C NMR spectrum of (1S,4R,9beta,11alpha,24R)-1-{[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (isomogroside IVE).

[0014] Detailed Description The following detailed description describes various aspects and embodiments provided herein. These descriptions should be read from the perspective of a person skilled in the relevant art. As such, they may not necessarily contain information that is known to such a person skilled in the art.

[0015] definition The following terms and phrases have the meanings set forth below unless otherwise indicated herein. This disclosure may use other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings they would have to one of ordinary skill in the art within the context of this disclosure. In some cases, a term or phrase may be defined in the singular or plural. In such cases, it is understood that any term in the singular may include its plural counterpart and vice versa, unless expressly indicated otherwise.

[0016] As used herein, "solvate" refers to a compound formed by the interaction of one or more solvent molecules with one or more compounds described herein. In some embodiments, the solvate is a edible acceptable solvate, such as a hydrate.

[0017] As used herein, "sweetener," "sweet flavoring agent," "sweet tastant," or "sweet compound" refers to a compound or a edible acceptable salt thereof that produces a detectable sweet flavor in a subject, e.g., a compound that activates the T1R2 / T1R3 receptor in vivo.

[0018] As used herein, "ppm" refers to a concentration in mg / kg based on the total weight of the composition.

[0019] As used herein, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. For example, reference to "a substituent" includes a single substituent as well as two or more substituents, and the like.

[0020] As used herein, "for example, for instance," "such as," or "including" is meant to introduce examples that further clarify a more general subject matter. Unless expressly indicated otherwise, such examples are provided only as an aid in understanding the embodiments set forth in the present disclosure and are not intended to be limiting in any way. Additionally, these phrases do not imply any kind of selection of the disclosed embodiments.

[0021] As used herein, "comprise" or "comprises" or "comprising" or "comprised of" refers to an open-ended group. This means that the group may contain additional elements in addition to those explicitly listed. For example, the phrase "comprising A" means that A must be present, but other elements may also be present. The terms "comprise", "having", "consisting of" and their grammatical variations have the same meaning. In contrast, "consist of" or "consists of" refers to a closed group. For example, the phrase "consisting of" means that A is present and that only A is present.

[0022] As used herein, "optionally" means that the event described thereafter may or may not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event occurs one or more times.

[0023] As used herein, "or" should be given its broadest reasonable interpretation and should not be limited to either / or construction. Thus, the phrase "comprising A or B" means that A can be present and B is not present, or B is present and A is not present, or both A and B are present. Furthermore, for example, if A defines a class that can have multiple elements, e.g., A1 and A2, one or more elements of the class can be present at the same time.

[0024] Chemical structures are often shown using a "skeletal" format in which carbon atoms are not explicitly represented and hydrogen atoms attached to carbon atoms are omitted entirely. For example, the structure [ka] represents butane (i.e., n-butane). Additionally, aromatic groups such as benzene are represented by showing one of the contributing resonance structures. For example, the structure [ka] represents toluene.

[0025] Other terms not included in this subsection are defined elsewhere in this specification.

[0026] Mogroside Compounds In a first aspect, the present disclosure provides a compound having the formula: [ka] The present invention provides a mogroside compound, which is a compound represented by the formula:

[0027] The compound of the above formula is referred to herein as (1S,4R,9beta,11alpha,24R)-1-{[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside, or by the abbreviation "MC1."

[0028] The sugar moieties depicted in the above structure are shown in closed ring form. The structures also encompass forms in which the depicted sugar moieties are in their open, acyclic form.

[0029] Isotopes may exist in the compounds described. Each chemical element represented in the compound structure may include any isotope of said element. For example, in the compound structure, hydrogen atoms may be explicitly disclosed or may be understood to exist in the compound. In any position of the compound where a hydrogen atom may exist, the hydrogen atom may be any isotope of hydrogen, including but not limited to hydrogen-1 (protium) and hydrogen-2 (deuterium). Thus, reference to a compound herein includes all possible isotopic forms, unless the context clearly indicates otherwise.

[0030] Solid forms and solutions of mogroside compounds In another aspect, the disclosure provides various solid forms of the MC1 compound.

[0031] In some embodiments, MC1 compound exists as a crystalline solid, either in substantially pure form or in a formulation as described below.Crystalline solid can have any suitable polymorphic form, such as any polymorphic form obtained by recrystallization in any suitable solvent system according to the techniques commonly used in the field of polymorph screening.

[0032] In some other embodiments, the MC1 compound exists as an amorphous solid or semi-amorphous solid, meaning that it does not have a regular crystal structure. Such solids can be produced using standard techniques such as spray drying.

[0033] In some embodiments, the MC1 compound exists as a solvate. This is a pseudo-form of the compound in which one or more solvent molecules (such as water molecules) are incorporated into the crystal structure. Any suitable solvent or combination of solvents can be used, including but not limited to water, methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, isobutanol, ethyl acetate, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol. In some embodiments, the present disclosure provides a hydrate of the MC1 compound. Such solvates can be generated by any suitable means, such as the techniques typically used by those skilled in the art in polymorph and solvate screening.

[0034] In some other embodiments, the MC1 compound is present as a co-crystal with one or more other compounds, such as one or more other sweetener compounds. The MC1 compound can form a co-crystal with any suitable compound. Non-limiting examples of such suitable compounds include fructose, glucose, galactose, sucrose, lactose, maltose, allulose, sugar alcohols (such as erythritol, sorbitol, xylitol), sucralose, steviol glycosides (such as natural stevioside compounds, such as rebaudioside A, rebaudioside E, and rebaudioside M), other mogrosides (mogroside V, isomogroside V, siamenoside I, isomogroside III, and the like). E, 1,6-α isomer of siamenoside I), aspartame, saccharin, acesulfame K, cyclamate, inulin, isomalt, and maltitol. Such co-crystals can be produced by any suitable means, such as those described in U.S. Patent Application Publication No. 2018 / 0363074, which is incorporated herein by reference.

[0035] In some embodiments, the MC1 compound is in the form of dry particles.Such dry particles can be formed by standard techniques in the art, such as dry granulation and wet granulation.Such particles can also contain a number of diluents, including inert diluents such as calcium carbonate, sodium carbonate, lactose, calcium phosphate, and sodium phosphate; granulating and disintegrating agents such as starch, cellulose-based materials, and alginic acid; binding agents such as gelatin, guar gum, and acacia; and lubricants such as magnesium stearate, stearic acid, and talc.Other excipients typically used in food and beverage products, such as typical food ingredients, can also be included.

[0036] In some embodiments, the MC1 compound is in the form of a liquid solution or liquid suspension. Such compositions may also include carboxymethylcellulose, methylcellulose, hydroxypropylmethylcellulose, sodium alginate, polyvinylpyrrolidone, gum tragacanth, and gum acacia. The dispersing agent or wetting agent may be a naturally occurring phosphatide such as lecithin, or a condensation product of an alkylene oxide with a fatty acid, such as polyoxyethylene stearate, or a condensation product of ethylene oxide with a long chain aliphatic alcohol, such as heptadecaethyl-enoxycetanol, or a condensation product of ethylene oxide with a partial ester derived from a fatty acid and a hexitol, such as polyoxyethylene sorbitol monooleate, or a condensation product of ethylene oxide with a partial ester derived from a fatty acid and a hexitol anhydride, such as polyethylene sorbitan monooleate. Such compositions may also include one or more colorants, one or more flavoring agents, and the like. Such liquid suspensions and solutions have a liquid carrier. Usually, the liquid carrier includes water. In some such cases, liquid composition is an emulsion, such as oil-in-water or water-in-oil emulsion.Furthermore, in some cases, the polarity of water is too high to dissolve MC1 compound to the target concentration.In such cases, it may be desirable to introduce water-miscible solvents, such as alcohols, glycols, polyols, into the solvent to increase the solubility of MC1 compound.

[0037] In some embodiments, MC1 compound is in the form of solution. That is, it is solvated in liquid carrier. In some embodiments, liquid carrier is aqueous carrier. Such solution can be diluted to any suitable concentration.

[0038] Formulations, Uses, and Methods In another aspect, the present disclosure provides formulations, uses, and methods using MC1 compounds. In another aspect, the present disclosure provides edible compositions containing MC1 compounds. In another aspect, the present disclosure provides the use of MC1 compounds for sweetening edible compositions. In another aspect, the present disclosure provides the use of MC1 compounds for reducing the bitterness of edible compositions. In another aspect, the present disclosure provides the use of MC1 compounds for enhancing the sweetness of edible compositions. In some embodiments thereof, the edible composition contains another sweetener (according to any of the embodiments described below). In another aspect, the present disclosure provides the use of MC1 compounds for enhancing the umami taste of edible compositions. In another aspect, the present disclosure provides the use of MC1 compounds for reducing the sourness of edible compositions.

[0039] The present disclosure also provides methods corresponding to each of the aforementioned uses. Thus, in certain related aspects, the present disclosure provides a method for enhancing the sweetness of an edible composition, comprising adding an amount (e.g., an effective amount for enhancing sweetness) of an MC1 compound to the edible composition. In some other related aspects, the present disclosure provides a method for sweetening an edible composition, comprising adding an amount (e.g., an effective amount for sweetening) of an MC1 compound to the edible composition. In some other related aspects, the present disclosure provides a method for reducing the bitterness of an edible composition, comprising adding an amount (e.g., an effective amount for reducing bitterness) of an MC1 compound to the edible composition.

[0040] The above-mentioned uses and methods generally include the use of MC1 compound in a composition containing one or more additional components.For example, in at least one embodiment, the present disclosure provides a composition containing MC1 compound, in which MC1 compound accounts for at least 1% by weight, or at least 2% by weight, or at least 3% by weight, or at least 5% by weight, or at least 10% by weight, or at least 20% by weight, or at least 30% by weight, or at least 40% by weight of the composition on a dry weight basis (e.g., based on the total weight of the composition excluding the weight of any liquid carrier).In a related embodiment, the present disclosure provides a solid-state composition containing MC1 compound, in which MC1 compound accounts for at least 1% by weight, or at least 2% by weight, or at least 3% by weight, or at least 5% by weight, or at least 10% by weight, or at least 20% by weight, or at least 30% by weight, or at least 40% by weight of the solid-state composition based on the total weight of the composition. In another related aspect, the present disclosure provides an edible composition containing an MC1 compound, wherein the concentration of the MC1 compound in the edible composition is at least 10 ppm, or at least 15 ppm, or at least 20 ppm, or at least 25 ppm, or at least 30 ppm, or at least 40 ppm, or at least 50 ppm, or at least 75 ppm, or at least 100 ppm, or at least 150 ppm, or at least 200 ppm, or at least 250 ppm, or at least 300 ppm. In another related aspect, the present disclosure provides an edible composition containing an MC1 compound, wherein the edible composition contains another sweetener, such as sucrose, fructose, xylitol, erythritol, allulose, glucose, or a combination thereof. In another related aspect, the present disclosure provides a concentrated sweetener composition containing any of the mogroside compounds of the aforementioned aspects, including any of the aforementioned embodiments or combinations of the embodiments thereof, and optionally another sweetener.

[0041] In certain specific embodiments, the edible composition contains sucrose and an MC1 compound. In some such embodiments, the addition of an MC1 compound allows the use of less sucrose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of a comparable product that uses more sucrose. In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions can be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below. In another embodiment, the edible composition is a beverage, such as a soda. Sucrose can be added in any suitable form, such as natural syrup (sugar cane syrup).

[0042] In certain specific embodiments, the edible composition contains fructose and MC1 compound. In some such embodiments, the addition of MC1 compound allows the use of less fructose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of the equivalent product that uses more fructose. In some embodiments, the concentration of MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of MC1 compound is at least 5 ppm. In some embodiments, the edible composition is a food product, such as any of those specifically listed below. In another embodiment, the edible composition is a beverage, such as a soda, etc. The fructose can be provided in any suitable form, such as natural syrup or high fructose corn syrup.

[0043] In certain specific embodiments, the edible composition contains high fructose corn syrup and MC1 compound.In some such embodiments, the addition of MC1 compound allows the use of less high fructose corn syrup (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the sweetness characteristic level of the equivalent product that uses more high fructose corn syrup.In some embodiments, the concentration of MC1 compound is 1000ppm or less, or 900ppm or less, or 800ppm or less, or 700ppm or less, or 600ppm or less, or 500ppm or less, or 400ppm or less, or 300ppm or less, or 200ppm or less, or 100ppm or less, or 50ppm or less, or 25ppm or less, or 10ppm or less.In some further such embodiments, the concentration of MC1 compound is at least 5ppm. In some embodiments, the edible composition is a food product, such as any of those specifically listed below: In another embodiment, the edible composition is a beverage, such as a soda.

[0044] In certain specific embodiments, the edible composition contains glucose (e.g., D-glucose in either its alpha or beta form, or a combination thereof) and an MC1 compound.In some such embodiments, the addition of an MC1 compound allows the use of less glucose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of a comparable product that uses more glucose.In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less.In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions may be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below. In another embodiment, the edible composition is a beverage, such as a soda. The glucose can be added in any suitable form, such as a natural syrup.

[0045] In certain specific embodiments, the edible composition contains sucralose and MC1 compound.In some such embodiments, the addition of MC1 compound allows the use of less sucralose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the sweetness characteristic level of the equivalent product that uses more sucralose.In some embodiments, the concentration of MC1 compound is 1000ppm or less, or 900ppm or less, or 800ppm or less, or 700ppm or less, or 600ppm or less, or 500ppm or less, or 400ppm or less, or 300ppm or less, or 200ppm or less, or 100ppm or less, or 50ppm or less, or 25ppm or less, or 10ppm or less.In some further such embodiments, the concentration of MC1 compound is at least 5ppm.Such edible composition can be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below: In another embodiment, the edible composition is a beverage, such as a soda.

[0046] In certain specific embodiments, an edible composition contains a rebaudioside (such as rebaudioside A, rebaudioside D, rebaudioside E, rebaudioside M, or any combination thereof) and an MC1 compound. In some such embodiments, the addition of the MC1 compound allows for the use of less rebaudioside (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the level of sweetness characteristics of a comparable product using more rebaudioside. In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions may be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below. In another embodiment, the edible composition is a beverage, such as a soda.

[0047] In certain specific embodiments, the edible composition contains acesulfame K and an MC1 compound. In some such embodiments, the addition of the MC1 compound allows the use of less acesulfame K (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of a comparable product that uses more acesulfame K. In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions may be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below: In another embodiment, the edible composition is a beverage, such as a soda.

[0048] In certain specific embodiments, the edible composition contains allulose and MC1 compound.In some such embodiments, the addition of MC1 compound allows the use of less allulose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of the equivalent product that uses more allulose.In some embodiments, the concentration of MC1 compound is 1000ppm or less, or 900ppm or less, or 800ppm or less, or 700ppm or less, or 600ppm or less, or 500ppm or less, or 400ppm or less, or 300ppm or less, or 200ppm or less, or 100ppm or less, or 50ppm or less, or 25ppm or less, or 10ppm or less.In some further such embodiments, the concentration of MC1 compound is at least 5ppm.Such edible composition can be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below. In some particular embodiments, the edible composition is a protein bar or a meal replacement bar. In another embodiment, the edible composition is a beverage, such as a soda.

[0049] In certain specific embodiments, the edible composition contains erythritol and an MC1 compound. In some such embodiments, the addition of an MC1 compound allows the use of less erythritol (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of a comparable product that uses more erythritol. In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions can be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below: In another embodiment, the edible composition is a beverage, such as a soda.

[0050] In certain specific embodiments, the edible composition contains aspartame and an MC1 compound. In some such embodiments, the addition of an MC1 compound allows the use of less aspartame (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of a comparable product that uses more aspartame. In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions may be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below: In another embodiment, the edible composition is a beverage, such as a soda.

[0051] In certain specific embodiments, the edible composition contains cyclamate and MC1 compound. In some such embodiments, the addition of MC1 compound allows the use of less cyclamate (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieves the level of sweetness characteristics of a comparable product that uses more cyclamate. In some embodiments, the concentration of MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of MC1 compound is at least 5 ppm. Such edible composition may be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below: In another embodiment, the edible composition is a beverage, such as a soda.

[0052] In certain specific embodiments, the edible composition contains another mogroside (mogroside III, mogroside IV, mogroside V, siamenoside I, isomogroside V, mogroside IV E , Isomogroside IV, Mogroside III E, 11-oxomogroside V, 1,6-α isomer of siamenoside I, and any combination thereof) and an MC1 compound. In some such embodiments, the addition of the MC1 compound allows the use of less of another mogroside (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) while still achieving the level of sweetness characteristics of a comparable product using more of another mogroside. In some embodiments, the concentration of the MC1 compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some further such embodiments, the concentration of the MC1 compound is at least 5 ppm. Such edible compositions may be in any suitable form. In some embodiments, the edible composition is a food product, such as any of those specifically listed below. In another embodiment, the edible composition is a beverage, such as a soda. Additional mogroside compounds that can be suitably used are described in US Patent Application Publication No. 2017 / 0119032.

[0053] In certain embodiments of any of the aspects and embodiments described herein relating to an edible composition, the edible composition is a non-naturally occurring product, such as a composition specially manufactured for the production of a flavored product, such as a processed food or beverage.

[0054] Typically, the compounds disclosed and described herein can be provided individually or in combination in a composition, such as an edible composition. In one embodiment, the compounds disclosed and described herein can be provided individually or in combination to impart a more sugar-like temporal or flavor profile to a sweetener composition by combining one or more compounds disclosed and described herein with one or more sweeteners in a sweetener composition. In another embodiment, the compounds disclosed and described herein can be provided individually or in combination to increase or enhance the sweetness of a composition by contacting the composition with a compound disclosed and described herein to form a modified composition.

[0055] Thus, in some embodiments, the composition according to any of the above aspects (including any of the uses or methods) contains an MC1 compound. In some embodiments, the composition further comprises a vehicle. In some embodiments, the vehicle is water. In some other embodiments, the vehicle is a bulking agent. In some embodiments, the MC1 compound is present at a concentration below its sweetness perception threshold. In some other embodiments, the MC1 compound is present at a concentration above its sweetness perception threshold.

[0056] In some embodiments, an additional sweetener is present. The additional sweetener can be present in any suitable concentration, depending on factors such as the potency of the sweetener as a sweetener, its water solubility, and the like. For example, in some embodiments, the additional sweetener is present in an amount of 0.1% to 12% by weight. In some embodiments, the additional sweetener is present in an amount of 0.2% to 10% by weight. In some embodiments, the additional sweetener is present in an amount of 0.3% to 8% by weight. In some embodiments, the additional sweetener is present in an amount of 0.4% to 6% by weight. In some embodiments, the additional sweetener is present in an amount of 0.5% to 5% by weight. In some embodiments, the additional sweetener is present in an amount of 1% to 2% by weight. In some embodiments, the additional sweetener is present in an amount of 0.1% to 5% by weight. In some embodiments, the additional sweetener is present in an amount of 0.1% to 4% by weight. In some embodiments, the additional sweetener is present in an amount of 0.1% to 3% by weight. In some embodiments, the additional sweetener is present in an amount of 0.1% to 2% by weight. In some embodiments, the additional sweetener is present in an amount of 0.1% to 1% by weight. In some embodiments, the additional sweetener is present in an amount of 0.1% to 0.5% by weight. In some embodiments, the additional sweetener is present in an amount of 0.5% to 10% by weight. In some embodiments, the additional sweetener is present in an amount of 2% to 8% by weight. In some further embodiments of the embodiments described in this paragraph, the additional sweetener is sucrose, fructose, glucose, xylitol, erythritol, glucose, allulose, or a combination thereof.

[0057] In some further embodiments, the additional sweetener is present in an amount between 10 ppm and 1000 ppm. In some embodiments, the additional sweetener is present in an amount between 20 ppm and 800 ppm. In some embodiments, the additional sweetener is present in an amount between 30 ppm and 600 ppm. In some embodiments, the additional sweetener is present in an amount between 40 ppm and 500 ppm. In some embodiments, the additional sweetener is present in an amount between 50 ppm and 400 ppm. In some embodiments, the additional sweetener is present in an amount between 50 ppm and 300 ppm. In some embodiments, the additional sweetener is present in an amount between 50 ppm and 200 ppm. In some embodiments, the additional sweetener is present in an amount between 50 ppm and 150 ppm. In some further embodiments of the embodiments described in this paragraph, the additional sweetener is any of the derivatives described above, such as steviol glycosides, mogrosides, glycoside derivatives (e.g., glucosylates), or any combination thereof.

[0058] The composition can include any suitable sweetener or combination of sweeteners. In some embodiments, the sweetener is a sweetener composition containing natural sugars such as common saccharide sweeteners such as sucrose, fructose, glucose, and corn syrup (such as high fructose corn syrup) or other syrups or sweetener concentrates derived from natural fruit-based and vegetable-based sources. In some embodiments, the sweetener is sucrose, fructose, or a combination thereof. In some embodiments, the sweetener is sucrose. In some other embodiments, the sweetener is selected from natural rare sugars including D-allose, D-psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-albinose, D-turanose, and D-leucrose. In some embodiments, the sweetener is selected from semi-synthetic "sugar alcohol" sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, and the like. In some embodiments, the sweetener is selected from artificial sweeteners such as aspartame, saccharin, acesulfame-K, cyclamate, sucralose, and alitame. In some embodiments, the sweetener is selected from the group consisting of cyclamic acid, mogrosides, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, allulose, neotame, and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysates (HSH), stevioside, rebaudioside A, other sweet stevia-based glycosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), karela, and other guanidine-based sweeteners. In some embodiments, the additional sweetener is a combination of two or more of the sweeteners described in this paragraph. In some embodiments, the sweetener may be a combination of two, three, four, or five sweeteners disclosed herein. In some embodiments, the additional sweetener is sugar.In some embodiments, the additional sweetener is a combination of one or more sugars and other natural and artificial sweeteners. In some embodiments, the additional sweetener is a sugar. In some embodiments, the sugar is cane sugar. In some embodiments, the sugar is sugar beet sugar. In some embodiments, the sugar may be sucrose, fructose, glucose, or a combination thereof. In some embodiments, the sugar is sucrose. In some embodiments, the sugar is a combination of fructose and glucose.

[0059] In some embodiments, the additional sweetener may also include one or more natural or synthetic carbohydrate-containing sweetener compositions, such as, for example, corn syrup, high fructose corn syrup, high maltose corn syrup, glucose syrup, sucralose syrup, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysates (HSH), or other syrups or sweetener concentrates derived from natural fruit- or vegetable-based sources, or semi-synthetic "sugar alcohol" sweeteners, such as polyols. Non-limiting examples of polyols in some embodiments include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomaltooligosaccharides, reduced xylooligosaccharides, reduced gentiooligosaccharides, reduced maltose syrup, reduced glucose syrup, isomaltulose, maltodextrin, and the like, as well as sugar alcohols or any other carbohydrate that can be reduced without adversely affecting the taste, or combinations thereof.

[0060] Additional sweeteners include, but are not limited to, agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugar, coconut syrup, date sugar, fructans (also called inulin fiber, fructooligosaccharides, or oligofructose), green stevia powder, stevia rebaudiana, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E , rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M, and other sweet stevia-based glycosides, stevioside, stevioside extract, honey, Jerusalem artichoke syrup, licorice root, Monk fruit (fruit, powder, or extract), Lucuma (fruit, powder, or extract), maple sap (e.g., sugar maple (Acer saccharum, black maple (Acer nigrum), red maple (Acer rubrum), silver maple (Acer saccharinum), Norway maple (Acer platanoides), ash maple (Acer negundo), bigleaf maple (Acer macrophyllum), bigleaf maple (Acer grandidentatum), Rocky Mountain maple (Acer glabrum), and silver maple (Acer mono), maple syrup, maple sugar, walnut sap (e.g., Juglans cinerea, Juglans nigra, Juglans ailatifolia, and Juglans regia), birch sap (e.g., Betula alba), papyrifera), yellow birch (Betula alleghaniensis), sweet beach (Betula lenta), river birch (Betula nigra), gray birch (Betula populifolia), and silver birch (Betula pendula).Sycamore sap (e.g., sap extracted from the American sycamore tree (Platanus occidentalis)), ironwood sap (e.g., sap extracted from the American asada (Ostrya virginiana)), muscovado, molasses (e.g., blackstrap molasses), molasses sugar, monatin, monellin, cane sugar (also called natural sugar, unrefined cane sugar, or sucrose), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, cassava syrup (also called tapioca syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt powder, beet sugar, sugar cane sugar, crystalline fruit juice crystals, caramel, carbitol, carob syrup, white sugar, hydrogenated starch hydrolysates, hydrolyzed canned juice, hydrolyzed starch, invert sugar, anethole, arabinogalactan, arop, syrup, P-4000, acesulfame potassium (also called acesulfame K or ace-K), alitame (also called acrame), advantame, aspartame, bayunoside, neotame, benzamide derivatives, bernadame, candelille, carrerame , and other guanidine-based sweeteners, vegetable fiber, corn sugar, coupling sugar, curculin, cyclamate, cyclocaryoside I, demerara, dextran, dextrin, maltodextrin, dulcin, sucrose, vulgin, dulcoside A, dulcoside B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucine, gluconic acid, gluconolactone, glucosamine, glucoronic acid, glycerol, glycine, glycyphyllin, glycyrrhizin , glycyrrhetinic acid monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, jiaogulan, hernandursin, isomerized liquid sugar, jalab, chicory root dietary fiber, kynurenine derivatives (N'-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine, etc.), galactitol, ritesse, ligicane, lycasin, ragduname, guanidine, falernum, mabinlin I, mabinlin II, maltol, multisorb,Maltodextrin, maltotriol, mannosamine, miraculin, starch syrup, mogrosides (such as mogroside IV, mogroside V, and neomogroside), mukurodiosides, nanosugar, naringin dihydrochalcone, neohesperidin dihydrochalcone, nib sugar, nigerooligosaccharides, norbu, olgate syrup, osladin, pekmez, pentadin, periandrin I, perillaldehyde, perillartine , petphyllum, phenylalanine, phlomisoside I, phlorodizin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refiner syrup, rub syrup, rubusoside, serigeain A, shugr, siamenoside I, siraitia grosvenorii, soy oligosaccharides, Splenda, SRI oxime V, steviol glycosides, steviolbioside, stevioside, strogin 1, 2 and 4, sucronate, sucrononate, sugar, suosan, phloridzin, super aspartame, tetrasaccharide, threitol, molasses, trilobtain, tryptophan and derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanilla sugar, volemitol, birch syrup, aspartame-acesulfame, asguline, and combinations or blends of any two or more thereof.

[0061] In yet another embodiment, the additional sweetener may be a chemically or enzymatically modified natural high-intensity sweetener. The modified natural high-intensity sweetener includes glycosylated natural high-intensity sweeteners such as glucosyl-, galactosyl-, or fructosyl-derivatives containing 1 to 50 glycoside residues. The glycosylated natural high-intensity sweeteners can be produced by enzymatic transglycosylation reactions catalyzed by various enzymes with transglycosylation activity. In some embodiments, the modified sweeteners may be substituted or unsubstituted.

[0062] Additional sweeteners also include combinations of any two or more of any of the aforementioned sweeteners. In some embodiments, the sweetener may include a combination of two, three, four, or five of the sweeteners disclosed herein. In some embodiments, the sweetener may be a sugar. In some embodiments, the sweetener may be a combination of one or more sugars and other natural and artificial sweeteners. In some embodiments, the sweetener is a caloric sweetener, such as sucrose, fructose, xylitol, erythritol, or combinations thereof. In some embodiments, the edible composition is free or (in some embodiments) substantially free of stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides, or rebaudiosides. For example, in some embodiments, the edible composition contains no stevia-derived sweeteners, or contains stevia-derived sweeteners at a concentration of 1000 ppm or less, or 500 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 20 ppm or less, or 10 ppm or less, or 5 ppm or less, or 3 ppm or less, or 1 ppm or less.

[0063] The MC1 compound can be present in the edible composition in any suitable amount. In some embodiments, the MC1 compound is present in an amount sufficient to enhance the taste of the composition (e.g., enhance sweetness, reduce sourness, or reduce bitterness). Thus, in some embodiments, the edible composition contains the MC1 compound at a concentration of 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 450 ppm or less, or 400 ppm or less, or 350 ppm or less, or 300 ppm or less, or 250 ppm or less, or 200 ppm or less, or 150 ppm or less, or 100 ppm or less, or 50 ppm or less, or 40 ppm or less, or 30 ppm or less, or 20 ppm or less. In some embodiments, the mogroside compound is present in a minimal amount, such as 1 ppm or 5 ppm. Thus, in some embodiments, the edible composition comprises an edible composition having a nutrient content of from 1 ppm to 1000 ppm, or from 1 ppm to 900 ppm, or from 1 ppm to 800 ppm, or from 1 ppm to 700 ppm, or from 1 ppm to 600 ppm, or from 1 ppm to 500 ppm, or from 1 ppm to 450 ppm, or from 1 ppm to 400 ppm, or from 1 ppm to 350 ppm, or from 1 ppm to 300 ppm, or from 1 ppm to 250 ppm, or from 1 ppm to 200 ppm, or from 1 ppm to 150 ppm, or from 1 ppm to 100 ppm, or from 1 ppm to 50 ppm, or from 1 ppm to 40 ppm, or from 1 ppm to 30 ppm, or from 1 ppm to 20 ppm. m, or 5 ppm to 1000 ppm, or 5 ppm to 900 ppm, or 5 ppm to 800 ppm, or 5 ppm to 700 ppm, or 5 ppm to 600 ppm, or 5 ppm to 500 ppm, or 5 ppm to 450 ppm, or 5 ppm to 400 ppm, or 5 ppm to 350 ppm, or 5 ppm to 300 ppm, or 5 ppm to 250 ppm, or 5 ppm to 200 ppm, or 5 ppm to 150 ppm, or 5 ppm to 100 ppm, or 5 ppm to 50 ppm, or 5 ppm to 40 ppm, or 5 ppm to 30 ppm, or 5 ppm to 20 ppm.In embodiments in which a sweetener such as sucrose or fructose is present, the weight to weight ratio of sweetener to MC1 compound in the edible composition ranges from 1000:1 to 50000:1, or from 1000:1 to 10000:1, or from 2000:1 to 8000:1.

[0064] Edible compositions or sweetener concentrates containing MC1 compounds may, in certain embodiments, contain any additional ingredient or combination of ingredients commonly used in food and beverage products, including, but not limited to, the following: acids, such as citric acid, phosphoric acid, ascorbic acid, sodium sulfate, lactic acid, or tartaric acid; bitter components such as caffeine, quinine, green tea, catechins, polyphenols, green robusta coffee extract, green coffee extract, potassium chloride, menthol, or proteins (such as proteins and protein isolates derived from plants, algae, or fungi); Coloring agents such as caramel color, red #40, yellow #5, yellow #6, blue #1, red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta carotene, turmeric curcumin, or titanium dioxide; preservatives, such as sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfite, sorbic acid, or benzoic acid; Antioxidants such as ascorbic acid, calcium disodium EDTA, alpha tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol, or sodium hexametaphosphate; For example, resveratrol, Co-Q10, omega-3 fatty acids, theanine, choline chloride (cytocholine), fibersol, inulin (chicory root), taurine, ginseng extract, guanine extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucoronolactone, inositol, bioflavonoids, echinacea, ginkgo biloba, yerba mate, flaxseed oil, garcinia cambogia husk extract, white tea extract, ribose, milk thistle extract, grape seed extract, pyrodixine HCl (vitamin B6), cyanocobalamin (vitamin B 12), vitamins or functional ingredients such as niacinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, cupric sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate, or zinc sulfate; clouding agents such as ester gum, brominated vegetable oil (BVO), or sucrose acetate isobutyrate (SAIB); buffers, such as sodium citrate, potassium citrate, or salts; Flavors such as propylene glycol, ethyl alcohol, glycerin, gum arabic (gum acacia), maltodextrin, modified corn starch, dextrose, natural flavors, natural flavors including other natural flavors (natural flavors WONF), natural and artificial flavors, artificial flavors, silicon dioxide, magnesium carbonate, or tricalcium phosphate; or Starches and stabilizers such as pectin, xanthan gum, carboxymethylcellulose (CMC), polysorbate 60, polysorbate 80, medium chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum arabic (gum acacia), inulin, or carrageenan.

[0065] Edible compositions or sweetener concentrates containing MC1 compounds can have any suitable pH. In some embodiments, the mogroside compounds enhance the sweetness of sweeteners over a wide range of pH, for example, from low to neutral pH. Low and neutral pH includes, but is not limited to, pH of 1.5-9.0, or 2.5-8.5; 3.0-8.0; 3.5-7.5; and 4.0-7. In certain embodiments, the MC1 compounds can enhance the perceived sweetness of a fixed concentration of sweetener in taste tests at compound concentrations of 50 μM, 40 μM, 30 μM, 20 μM, or 10 μM at both low and neutral pH values. In certain embodiments, the enhancement factor of the compounds disclosed and described herein, individually or in combination, at low pH is substantially similar to the enhancement factor of the compounds at neutral pH. Due to such consistent sweetness enhancement properties under a wide range of pH, the compounds disclosed and described herein can be widely used, individually or in combination, in a wide variety of foods and beverages.

[0066] The edible compositions described according to any of the foregoing embodiments, in certain embodiments, also contain one or more additional flavor modifying compounds, such as a sweetness enhancing compound (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), a bitterness blocking compound, an umami enhancing compound, a sour or licorice taste reducing compound, a saltiness enhancing compound, a cooling effect enhancing compound, or any combination of the foregoing.

[0067] Therefore, in some embodiments, the edible composition disclosed herein contains MC1 compound combined with one or more other sweetness enhancing compounds.Such sweetness enhancing compounds include, but are not limited to, naturally occurring compounds such as hesperitin, naringenin, glucosylated steviol glycoside, or synthetic compounds such as any compounds described in U.S. Patent No. 8,541,421; U.S. Patent No. 8,815,956; U.S. Patent No. 9,834,544; U.S. Patent No. 8,592,592; U.S. Patent No. 8,877,922; U.S. Patent No. 9,000,054; and U.S. Patent No. 9,000,051, and U.S. Patent Application Publication No. 2017 / 0119032. MC1 compounds may be used in a range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, e.g. 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:8, 1:9, 1:10, 1:1 ... The MC1 compound may be used in combination with such other sweetener enhancers in any suitable ratio (w / w) of 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1. In some embodiments of any of the above embodiments, the MC1 compound is combined with a glucosylated steviol glycoside in any of the above ratios. As used herein, the term "glucosylated steviol glycoside" refers to the product of enzymatic glucosylation of a natural steviol glycoside compound. Glucosylation usually occurs through glycosidic bonds such as α-1,2, α-1,4, α-1,6, β-1,2, β-1,4, and β-1,6.In some embodiments of any of the above embodiments, the MC1 compound is combined with 3-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2,2-dimethyl-N-propyl-propanamide in any of the above ratios.

[0068] In some further embodiments, the edible composition disclosed herein contains MC1 compound combined with one or more umami enhancing compounds.Such umami enhancing compounds include but are not limited to naturally occurring compounds such as ericamide, or synthetic compounds such as any compounds described in U.S. Patent No. 8,735,081; U.S. Patent No. 8,124,121; and U.S. Patent No. 8,968,708. MC1 compounds may be used in a range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, e.g. 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, Any suitable ratio (w / w) of 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1 may be used in combination with such umami enhancers.

[0069] In some further embodiments, the edible compositions disclosed herein contain an MC1 compound in combination with one or more cooling effect enhancing compounds, including but not limited to naturally occurring compounds such as menthol or its analogs, or synthetic compounds such as any of the compounds described in U.S. Patents 9,394,287 and 10,421,727. MC1 compounds may be used in a range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, e.g. 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:8, 1:9, 1:10, 1:1 ... 1:1, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1 in any suitable ratio (w / w).

[0070] In some further embodiments, the edible composition disclosed herein contains MC1 compound combined with one or more bitterness-blocking compounds.Such bitterness-blocking compounds include, but are not limited to, naturally occurring compounds such as menthol or its analogs, or synthetic compounds such as any compounds described in U.S. Patent Nos. 8,076,491; 8,445,692; and 9,247,759. MC1 compounds may be used in a range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, e.g. 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, Any suitable ratio (w / w) of 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1 may be used in combination with such bitter blockers.

[0071] In some further embodiments, the edible compositions disclosed herein contain an MC1 compound in combination with one or more acidity modulating compounds. The MC1 compound is in the range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:8, 1:9, 1:10, 1:11, 1:10 ... The acidity modulating compounds may be used in any suitable ratio (w / w) of 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.

[0072] In some further embodiments, the edible compositions disclosed herein contain MC1 compounds in combination with one or more palatability improving compounds. Such palatability improving compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, etc. The MC1 compounds may be in the range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:8, 1:9, 1:10 ... The composition may be used in combination with such mouthfeel improvers in any suitable ratio (w / w) of 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.

[0073] In some further embodiments, the edible compositions disclosed herein contain MC1 compounds in combination with one or more flavor masking compounds. Such flavor masking compounds include, but are not limited to, cellulosic materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonate salts), and the like. The MC1 compounds are in the range of 1:1000-1000:1, or 1:100-100:1, or 1:50-50:1, or 1:25-25:1, or 1:10-10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, Any suitable ratio (w / w) of 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1 may be used in combination with such flavor masking compounds.

[0074] In some aspects related to the above-mentioned aspects and embodiments, the present disclosure provides the use of MC1 compounds to enhance the flavor of a flavored composition, such as a flavored product. Such a flavored composition can use any suitable flavor, such as any of the flavors described above.

[0075] Flavoured Products and Concentrates In certain aspects, the present disclosure provides a flavored product comprising any of the compositions of the five aspects described above. In some embodiments, the flavored product is a beverage, such as soda, flavored water, tea, etc. In some other embodiments, the flavored product is a food product, such as yogurt.

[0076] In some embodiments where the flavored product is a beverage, the beverage may be selected from the group consisting of fortified sparkling beverages, cola, lemon-lime flavored sparkling beverages, orange flavored sparkling beverages, grape flavored sparkling beverages, strawberry flavored sparkling beverages, pineapple flavored sparkling beverages, ginger ale, root beer, fruit juice, fruit flavored juice, fruit juice drink, nectar, vegetable juice, vegetable flavored juice, sports drink, energy drink, fortified water drink, vitamin fortified water, near water drink, coconut water, tea type beverage, coffee, cocoa beverage, beverage containing dairy ingredients, beverage containing grain extract, and smoothie. In some embodiments, the beverage may be a soft drink.

[0077] In certain embodiments of any of the aspects and embodiments described herein relating to flavored products, the flavored product is a non-naturally occurring product, such as a packaged food or beverage item.

[0078] Further non-limiting examples of food and beverage products or formulations include sweet coatings, frostings, or glazes for such products or any of those products within the soup category, the dried prepared food category, the beverage category, the ready meal category, the canned or preserved food category, the frozen prepared food category, the refrigerated prepared food category, the snack food category, the baked goods category, the confectionery category, the dairy category, the ice cream category, the meal replacement category, the pasta and noodle category, the sauces, dressings, condiments category, the baby food category, and / or the spreads category.

[0079] In general, the soup category refers to canned / preserved, dehydrated, instant, refrigerated, UHT, and frozen soups. For the purposes of this definition, soup means a liquid cooked food prepared from meat, poultry, fish, vegetables, grains, fruits, and other ingredients and may contain visible portions of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed, or filled, ready to drink, semi-concentrated, or concentrated, and may be served hot or cold, as the first or main dish of a meal, or as a snack between meals (sipped like a beverage). Soups can be used as ingredients to prepare other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups).

[0080] The dehydrated and culinary food category generally refers to: (i) cooking aid products such as powders, granules, pastes, concentrated liquid products, e.g., concentrated bouillons, bouillons, and bouillon-like products in pressed cube, tablet, powder, or granule form, sold separately as finished products or as ingredients in products, sauces, and recipe mixes (regardless of technology); (ii) meal solution products such as dehydrated soup mixes, dehydrated instant soups, dehydrated cooked soups, dehydrated or ambient cooked ready-made dishes, and meals and single-serving meals including pasta, potato, and rice dishes; and (iii) meal garnish products such as condiments, marinades, salad dressings, salad toppings, dips, bread, batter mixes, shelf-stable spreads, barbecue sauces, liquid recipe mixes, concentrates, and sauce or sauce mixes including recipe mixes for salads, whether dehydrated, liquid, or frozen, sold as finished products or as ingredients in products.

[0081] The beverage category generally refers to beverages, beverage mixes, and concentrates, including, but not limited to, carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready-to-drink beverages, liquid concentrated formulations for preparing beverages such as sodas, and dry powdered beverage precursor mixes. The beverage category also includes alcoholic beverages, soft drinks, sports drinks, isotonic drinks, and hot drinks. Alcoholic beverages include, but are not limited to, beer, cider / perry, FAB, wine, and spirits. Soft drinks include, but are not limited to, carbonated beverages, such as cola and non-cola carbonated drinks; fruit juices, such as juices, nectars, juice drinks, and fruit-flavored drinks; bottled waters, such as sparkling water, spring water, and refined / table water; functional beverages, such as sports drinks, energy drinks, or elixirs, which may be carbonated or non-carbonated; and concentrates, such as ready-to-drink liquid concentrates and powder concentrates. Hot or cold drinks include, but are not limited to, coffee or iced coffee, such as fresh coffee, instant coffee, and blended coffee; tea or iced tea, such as black tea, green tea, white tea, oolong tea, and flavored tea; and other beverages, including flavored, malt, or plant-based powders, granules, blocks, or tablets mixed with milk or water.

[0082] The snack food category generally refers to any food that may be a light, informal meal, such as, but not limited to, sweet and savory snacks and snack bars. Examples of snack foods include, but are not limited to, fruit snacks, chips / crisps, extruded snacks, tortilla / corn chips, popcorn, pretzels, nuts, and other sweet and savory snacks. Examples of snack bars include, but are not limited to, granola / muesli bars, breakfast bars, energy bars, fruit bars, and other snack bars.

[0083] The baked goods category generally refers to any edible product whose manufacturing process involves exposure to heat or excessive sunlight. Examples of baked goods include, but are not limited to, bread, rolls, cookies, muffins, cereals, toaster pastries, pastries, waffles, tortillas, biscuits, pies, bagels, tarts, quiches, cakes, any baked goods, and any combination thereof.

[0084] The ice cream category generally refers to frozen desserts that contain cream, sugar, and flavors. Examples of ice cream include, but are not limited to, ice cream for store consumption; take-out ice cream; frozen yogurt and specialty ice cream; soy, oat, bean (e.g., red bean and mung bean), and rice-based ice cream.

[0085] The confectionery category generally refers to edible products that have a sweet taste. Examples of confectionery include, but are not limited to, candy, gelatin, chocolate confectionery, sugar confectionery, gum, and the like, and any combination of products.

[0086] The meal replacement category generally refers to any food product intended to replace a regular meal, especially for people with health and fitness concerns. Examples of meal replacements include, but are not limited to, weight loss and recovery products.

[0087] The ready meal category generally refers to any food that can be served as a meal without extensive preparation or processing. Ready meals include products to which the manufacturer has added recipe "skill," thus facilitating speed, completeness, and convenience. Examples of ready meals include, but are not limited to, canned / preserved, frozen, dried, and refrigerated ready meals; dinner mixes; frozen pizza; refrigerated pizza; and pre-prepared salads.

[0088] The pasta and noodles category includes, but is not limited to, canned, dried, and refrigerated / fresh pasta; and any pasta and / or noodles, such as plain, instant, refrigerated, frozen, and snack noodles.

[0089] The canned / preserved food category includes, but is not limited to, canned / preserved meat and meat products, fish / seafood, vegetables, tomatoes, beans, fruit, ready meals, soups, pasta, and other canned / preserved foods.

[0090] Frozen processed food categories include, but are not limited to, frozen processed red meat, processed poultry, processed fish / seafood, processed vegetables, meat substitutes, processed potatoes, bakery products, desserts, ready meals, pizza, soups, noodles, and other frozen foods.

[0091] Dry processed food categories include, but are not limited to, rice, dessert mixes, dried ready meals, dehydrated soups, instant soups, dried pastas, plain noodles, and instant noodles. Refrigerated processed food categories include, but are not limited to, refrigerated processed meats, processed fish / seafood products, lunch kits, fresh cut fruit, ready meals, pizza, prepared salads, soups, fresh pastas, and noodles.

[0092] The sauces, dressings, and condiments category includes, but is not limited to, tomato paste and puree, bouillon / stock cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy-based sauces, pasta sauces, wet / cooking sauces, dry sauces / powder mixes, ketchup, mayonnaise, mustard, salad dressings, vinaigrettes, dips, pickle products, and other sauces, dressings, and condiments.

[0093] Baby food categories include, but are not limited to, milk-based or soy-based formulas; as well as cooked, dried, and other baby foods.

[0094] Spread categories include, but are not limited to, jams and preserves, honey, chocolate spreads, nut-based spreads, and yeast-based spreads.

[0095] The dairy category generally refers to edible products made from mammalian milk. Examples of dairy products include, but are not limited to, drinking dairy products, cheese, yogurt, and sour milk beverages, as well as other dairy products.

[0096] Further examples of flavoured products, particularly food and beverage products or formulations, are given below. Exemplary edible compositions include one or more of confectionery, chocolate confectionery, tablets, count lines, self lined / soft lines in bags, boxed assortments, standard boxed assortments, twist wrapped miniatures, seasonal chocolates, chocolates with toys, alfajores, other chocolate confectionery, mints, standard mints, strong mints, hard candies, lozenges, gums, jellies and chewing confectionery, toffees, caramels and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, bread, packaged / commercial bread, unpackaged / specialty bread, sweet bread, cake, packaged / commercial cake, unpackaged / specialty cake, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savory biscuits and crackers, bread substitutes, breakfast cereals, rte cereals, home breakfast cereals, flakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, ice cream for store consumption, individually packaged dairy ice cream ice cream, individually wrapped ice cream, multipack dairy ice cream, multipack ice cream, takeaway ice cream, takeaway dairy ice cream, ice cream desserts, bulk ice cream, takeaway ice cream, frozen yogurt, specialty ice cream, dairy products, milk, raw / pasteurized milk, raw / pasteurized full fat milk, raw / pasteurized semi-skimmed milk, long life / uht milk, long life / uht full fat milk, long life / uht semi-skimmed milk, long life / uht non-fat milk, goat milk, condensed / evaporated milk, plain co Condensed / evaporated milk, flavoured, functional and other condensed milk, flavoured milk beverages, dairy only flavoured milk beverages, flavoured milk beverages with fruit juice, soy milk, sour milk beverages, cultured milk beverages, coffee whiteners, milk powder, flavoured milk powder beverages, cream, cheese, processed cheese, spreadable processed cheese, non-spreadable processed cheese, non-processed cheese, spreadable non-processed cheese, hard cheese, packaged hard cheese, non-packaged hard cheese, yogurt,Plain / Natural Yogurt, Flavoured Yogurt, Yogurt with Fruit, Probiotic Yogurt, Drinkable Yogurt, Drinkable Yogurt, Probiotic Drinkable Yogurt, Refrigerated & Shelf-Stable Desserts, Dairy-Based Desserts, Soy-Based Desserts, Chilled Snacks, Fromagee Frais & Quark, Plain Fromagee Frais & Quark, Flavoured Fromagee Frais & Quark, Flavoured Fromagee Frais & Quark, Sweet & Savoury Snacks, Fruit Snacks, Chips / Crisps, Extruded Snacks, Tortilla / Corn Chips, Popcorn, Pretzels, Nuts, Other Sweet & Savoury Snacks, Snack Bars, Granola Bars, Breakfast Bars, Energy Bars, Fruit Bars, Other Snack Bars, Meal Replacement Products, Slimming Products, Recovery Drinks, Ready Meals, Canned Ready Meals, Frozen Ready Meals, Dehydrated Ready Meals, Refrigerated Ready Meals, Dinner Mixes, Frozen Pizza, Refrigerated Pizza, Soup, Canned Soups, Dehydrated Soups, Instant Soups, Refrigerated Soups, Hot Soups, Frozen Soups, Pasta, Canned Pasta, Dried Pasta , refrigerated / fresh pasta, noodles, plain noodles, instant noodles, cup / bowl instant noodles, pouch instant noodles, chilled noodles, snack noodles, canned food, canned meat and meat products, canned fish / seafood, canned vegetables, canned tomatoes, canned beans, canned fruit, canned ready meals, canned soups, canned pasta, other canned foods, frozen foods, frozen processed red meat, frozen processed poultry, frozen processed fish / seafood, frozen processed vegetables, frozen meat substitutes, frozen potatoes, oven baked potato chips, other oven baked potato products, non-oven baked frozen potatoes, frozen base Curry Products, Frozen Desserts, Frozen Ready Meals, Frozen Pizza, Frozen Soups, Frozen Noodles, Other Frozen Foods, Dehydrated Foods, Dessert Mixes, Dehydrated Ready Meals, Dehydrated Soups, Instant Soups, Dehydrated Pasta, Plain Noodles, Instant Noodles, Cup / Bowl Instant Noodles, Pouch Instant Noodles, Refrigerated Foods, Refrigerated Processed Meats, Refrigerated Fish / Seafood Products, Refrigerated Processed Fish, Refrigerated Battered Fish, Refrigerated Smoked Fish, Refrigerated Lunch Kits, Refrigerated Ready Meals, Refrigerated Pizza, Refrigerated Soups, Refrigerated / Fresh Pasta, Chilled Noodles, Oils & Fats, Olive Oil, Vegetable & Seed Oils, Cooking Fats,butter, margarine, spreadable fats and oils, functional spreadable fats and oils, sauces, dressings and condiments, tomato paste and puree, bouillon / stock cubes, stock cubes, gravy granules, liquid stocks and fonds, herbs and spices, fermented sauces, soy based sauces, pasta sauces, wet sauces, dry sauces / powder mixes, ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings, regular salad dressings, low fat salad dressings, vinaigrettes, dips, pickle products, other sauces, dressings and condiments, baby food, formula, standard formula, follow-up formula, toddler formula, hypoallergen formula, prepared baby food, dry baby food, other baby food, spreads, jams and preserves, honey, chocolate spreads, nut based spreads, and yeast based spreads. Exemplary edible compositions also include confectionery, bakery products, ice cream, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dry foods, refrigerated foods, fats and oils, baby foods, or spreads, or mixtures thereof. Exemplary edible compositions also include solid or liquid concentrate compositions for preparing breakfast cereals, sweetened drinks, or beverages, ideally to allow for reduced concentrations of known sugar sweeteners or artificial sweeteners.

[0097] Some embodiments provide chewable compositions that may or may not be intended to be swallowed. In some embodiments, the chewable compositions may be gums, chewing gums, sweetened gums, sugarless gums, functional gums, bubble gums, which contain the compounds disclosed and described herein, individually or in combination.

[0098] In some embodiments, the MC1 compound modulates the sweetness or other taste characteristics of other natural or synthetic sweet tastants and edible compositions made therefrom. In one embodiment, the MC1 compound can be used or provided at its ligand-enhanced concentration. For example, in some such embodiments, the MC1 compound is present in the edible composition at a concentration ranging from 0.001 ppm to 100 ppm, or at a narrower selection range of 0.1 ppm to 50 ppm, 0.01 ppm to 40 ppm, 0.05 ppm to 30 ppm, 0.01 ppm to 25 ppm, or 0.1 ppm to 30 ppm, or 0.1 ppm to 25 ppm, or 1 ppm to 30 ppm, or 1 ppm to 25 ppm.

[0099] In some embodiments, the MC1 compound is provided in a flavored concentrated formulation suitable for further processing, for example to produce a ready-to-use (i.e., ready-to-serve) product. By "flavored concentrated formulation" is meant a formulation that needs to be reconstituted with one or more dilution media to become a ready-to-use composition. The term "ready-to-use composition" is used interchangeably herein with "edible composition", which means any substance that can be taken orally, whether or not it is intended for ingestion, alone or together with other substances. In one embodiment, the ready-to-use composition includes a composition that can be directly ingested by humans or animals. The flavored concentrated formulation is used to impart or modify one or more flavors to a dilution medium, typically by mixing or diluting with one or more dilution media, such as any ingestible or edible ingredient or product. Such a use process is often referred to as reconstitution. Reconstitution can be carried out in a domestic or industrial environment. For example, a frozen fruit juice concentrate can be reconstituted with water or other aqueous medium by a consumer in the kitchen to obtain a ready-to-drink fruit juice beverage. In another example, a soft drink syrup concentrate can be reconstituted with water or other aqueous medium by a large commercial scale manufacturer to produce a ready-to-drink soft drink. Flavored concentrated formulations have higher concentration of flavoring agent or flavor modifying agent than ready-to-use composition, so flavored concentrated formulations are typically not suitable for direct consumption without reconstitution.There are many advantages to the use and manufacture of flavored concentrated formulations.For example, one advantage is that flavored concentrated formulations can be reconstituted at the time of use by adding suitable solvent, solid or liquid, so that weight and volume for transportation are reduced.

[0100] In certain embodiments of any aspect and embodiment described herein that refers to a sweetener or flavoring concentrate, the sweetener or flavoring concentrate is a non-naturally occurring product, such as a composition specially manufactured for the production of a flavored product, such as a food or beverage item.

[0101] In some embodiments, the flavored concentrated formulation contains the MC1 compound, a carrier, and at least one optional auxiliary. The term "carrier" refers to a normally inert auxiliary substance, such as a solvent, binder, bulking agent, or other inert medium, which is used in combination with the compound and one or more optional auxiliary agents to form a formulation. For example, for flavored concentrated formulations, the carrier can be water or starch. In some embodiments, the carrier is the same as the dilution medium for reconstituting the flavored concentrated formulation; in other embodiments, the carrier is different from the dilution medium. The term "carrier" as used herein includes, but is not limited to, edible acceptable carriers.

[0102] The term "auxiliary agent" refers to an additive that supplements, stabilizes, maintains, or enhances the intended function or effectiveness of an active ingredient, such as a compound of the present invention. In one embodiment, the at least one auxiliary agent comprises one or more flavoring agents. The flavoring agents may be any flavor known to a person skilled in the art or a consumer, such as flavors of chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof. In another embodiment, the at least one auxiliary agent comprises one or more sweeteners. The one or more sweeteners may be any sweetener described in this application. In another embodiment, the at least one auxiliary agent comprises one or more ingredients selected from the group consisting of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described in U.S. Pat. No. 6,468,576, the contents of which are incorporated herein by reference in their entirety for all purposes.

[0103] In some embodiments, the flavored concentrated formulations may be in a form selected from the group consisting of liquids, including solutions and suspensions, solids, foams, pastes, gels, creams, and combinations thereof, such as liquids containing a certain amount of solids. In one embodiment, the flavored concentrated formulations are in the form of liquids, such as aqueous and non-aqueous. In some embodiments, the flavored concentrated formulations may be carbonated or non-carbonated.

[0104] The flavored concentrated formulation may further include a freezing point depressant, a nucleating agent, or both as at least one auxiliary. A freezing point depressant is an ingestible compound or agent that can depress the freezing point of the liquid or solvent to which the compound or agent is added. That is, a liquid or solution containing the freezing point depressant has a lower freezing point than a liquid or solvent without the freezing point depressant. In addition to depressing the starting freezing point, the freezing point depressant can also reduce the water activity of the flavored concentrated formulation. Examples of freezing point depressants include, but are not limited to, carbohydrates, oils, ethyl alcohol, polyols such as glycerol, and combinations thereof. Nucleating agent refers to an ingestible compound or agent that can promote nucleation. The presence of a nucleating agent in the flavored concentrated formulation can improve the mouthfeel of the frozen blush of the frozen slush by increasing the number of desirable ice crystallization centers, and aid in maintaining the physical properties and performance of the slush at freezing temperatures. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

[0105] In some embodiments, the flavored concentrated formulations are formulated to have a low water activity to extend shelf life. Water activity is the ratio of the vapor pressure of water in the formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the flavored concentrated formulation has a water activity of less than about 0.85. In another embodiment, the flavored concentrated formulation has a water activity of less than about 0.80. In another embodiment, the flavored concentrated formulation has a water activity of less than about 0.75.

[0106] In some embodiments, the flavored concentrated formulation has the compound at a concentration that is at least 2 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 5 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 10 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 15 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 20 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 30 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 40 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 50 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrated formulation has the compound at a concentration that is at least 60 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavored concentrate formulation has the compound at a concentration that is up to 100 times the concentration of the compound in the ready-to-use composition.

[0107] The sweetener or flavor concentrate described according to any of the foregoing embodiments, in certain embodiments, also contains one or more additional mogroside compounds, such as a sweetness enhancing compound (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), a bitterness masking compound (e.g., eriodictyol, homoeriodictyol, sterubin, and salts or glycoside derivatives thereof, as well as vanillyl lignans, such as matairesinol and other compounds described in WO 2012 / 146584), an umami enhancing compound (e.g., rubemamine, rubesenamine, (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide, etc.), a sour and / or licorice taste reducing compound, a saltiness enhancing compound, a cooling effect enhancing compound, or any combination of the foregoing.

[0108] In some embodiments, the edible composition containing the MC1 compound also contains one or more vanilla flavor compounds, such as 4-hydroxy-3-methoxy-benzaldehyde or 2-hydroxy-4-methoxybenzaldehyde. Such edible compositions can be suitably used in a variety of different flavored products, such as coffee-based beverages, protein mixes, meal replacement beverages, ice cream, etc.

[0109] Tabletop Composition In some further aspects, the present disclosure provides a tabletop sweetener composition comprising: (a) at least one sweetener composition according to any of the preceding aspects and embodiments thereof (i.e., a composition comprising a sweetener and an MC1 compound); and (b) at least one bulking agent.

[0110] The tabletop sweetener composition can be in any suitable form, including, but not limited to, an amorphous solid, a crystal, a powder, a tablet, a liquid, a cube, a sugar-coated or coated product, a granular product, an encapsulated form enriched in or coated on a wet or dry carrier / particle, or a combination thereof.

[0111] The tabletop sweetener composition may contain other additives known to those skilled in the art. These additives include, but are not limited to, air-forming agents, bulking agents, carriers, fibers, sugar alcohols, oligosaccharides, sugars, high-intensity sweeteners, nutritive sweeteners, flavors, flavor enhancers, flavor stabilizers, acidulants, anti-caking agents, and free-flowing agents. Such additives are described, for example, by H. Mitchell (H. Mitchell, SWEETENERS AND SUGAR ALTERNATIVES IN FOOD TECHNOLOGY, Blackwell Publishing Ltd, 2006, which is incorporated herein by reference in its entirety). The term "flavor" as used herein may include flavors known to those skilled in the art, such as natural and artificial flavors. These flavors may be selected from synthetic flavor oils and flavor aroma oils or oils, oleoresins, and extracts derived from plants, leaves, flowers, fruits, etc., and combinations thereof. Non-limiting representative flavor oils include spearmint oil, cinnamon oil, wintergreen oil (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, nutmeg oil, allspice, sage oil, mace, bitter almond oil, and cassia oil.Also useful flavors are artificial, natural, and synthetic fruit flavors such as vanilla, and citrus oils such as lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences such as apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, plum, cherry, raspberry, blackberry, tropical fruits, mango, mangosteen, pomegranate, and papaya.Other promising flavors include milk flavors, butter flavors, cheese flavors, cream flavors, and yogurt flavors; vanilla flavors; tea or coffee flavors, such as green tea flavors, oolong tea flavors, tea flavors, cocoa flavors, chocolate flavors, and coffee flavors; mint flavors, such as peppermint flavors, spearmint flavors, and Japanese mint flavors; asafoetida flavors, ajowan flavors, anise flavors, angelica flavors, fennel flavors, allspice flavors, cinnamon flavors, chamomile flavors, mustard flavors, cardamom flavors, caraway flavors, cumin flavors, clove flavors, pepper flavors, coriander flavors, sassafras flavors, savory flavors, pepper flavors, perilla flavors, juniper berry flavors, ginger flavors, star anise flavors, horseradish flavors, thyme flavors, tarragon flavors, dill flavors, chili flavors, nutmeg flavors, basil flavors, marjoram flavors, rosemary flavors, bay leaf flavors, and wasabi (Japanese These flavoring agents include spicy flavors such as spiced spices (horseradish) flavors; alcoholic flavors such as wine flavors, whiskey flavors, brandy flavors, rum flavors, gin flavors, and liqueur flavors; floral flavors; and vegetable flavors such as onion flavors, garlic flavors, cabbage flavors, carrot flavors, celery flavors, mushroom flavors, and tomato flavors. These flavoring agents can be used in liquid or solid form and can be used separately or mixed. Commonly used flavors include mints, such as peppermint, menthol, spearmint, artificial vanilla, cinnamon derivatives, and various fruit flavors, whether used separately or mixed.Flavors may also provide breath freshening properties when used in combination with cooling agents, particularly mint flavors.

[0112] Flavors can also provide breath freshening properties, especially mint flavors, when used in combination with cooling agents. These flavors can be used in liquid or solid form, and can be used separately or mixed. Other useful flavors can be used, including aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarbyl acetate, eugenyl formate, p-methylamisole, etc. Generally, any flavor or food additive can be used, as described in CHEMICALS USED IN FOOD PROCESSING, Publication 1274, pp. 63-258 (National Academy of Sciences). This publication is incorporated herein by reference.

[0113] Additional examples of aldehyde flavors include, but are not limited to, acetaldehyde (apple), benzaldehyde (cherry, almond), anisaldehyde (licorice, anise), cinnamaldehyde (cinnamon), citral or alpha-citral (lemon, lime), neral or beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope or piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde (spicy fruity flavors), butyraldehyde (butter, cheese), valeraldehyde ( Butter, cheese), citronellal (modified, many varieties), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits), 2-ethylbutyraldehyde (berry fruits), hexenal or trans-2 (berry fruits), tolylaldehyde (cherry, almond), veratraldehyde (vanilla), 2,6-dimethyl-5-heptenal or melonal (melon), 2,6-dimethyloctanal (green fruits), and 2-dodecenal (citrus, mandarin), cherry, grape, strawberry shortcake, and mixtures thereof. This list of flavors is merely illustrative and is not intended to limit either the term "flavor" or the overall scope of the present disclosure.

[0114] In some embodiments, the flavors can be used either in liquid form and / or in dry form. When used in the latter form, suitable drying means can be used, such as spray drying the oil. Alternatively, the flavors can be absorbed or encapsulated in water-soluble materials such as cellulose, starch, sugar, maltodextrin, gum arabic, etc. The actual techniques for producing such dry forms are well known.

[0115] In some embodiments, the tabletop sweetener can be made to resemble brown sugar, in which case compounds that impart brown notes can be added to the composition to make it taste more similar to brown sugar.

[0116] In some embodiments, the flavors can be used in many different physical forms known in the art to provide an initial burst of flavor and / or a lasting sensation of flavor, including, but not limited to, free forms, such as spray dried, powdered, beaded forms, encapsulated forms, and mixtures thereof.

[0117] Suitable bulking agents include, but are not limited to, maltodextrin (10DE, 18DE, or 5DE), corn syrup solids (20 or 36DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose, and cellulose derivatives, and the like, and mixtures thereof. In addition, granulated sugar (sucrose) or other caloric sweeteners, such as crystalline fructose, other carbohydrates, or sugar alcohols, can be used as bulking agents because they homogenize the ingredients well without adding significant calories.

[0118] In one embodiment, the at least one bulking agent can be a bulking agent described in U.S. Patent No. 8,993,027. In another embodiment, the at least one bulking agent can be a bulking agent described in U.S. Patent No. 6,607,771. In another embodiment, the at least one bulking agent can be a bulking agent described in U.S. Patent No. 6,932,982.

[0119] In some embodiments, the tabletop sweetener composition may further comprise at least one anti-caking agent. The phrases "anti-caking agent" and "flow agent" as used herein refer to any composition that prevents, reduces, inhibits, or inhibits at least one sweetener from adhering to, binding to, or contacting another sweetener molecule. Alternatively, an anti-caking agent may refer to any composition that aids in the homogeneity and uniform dissolution of ingredients. Non-limiting examples of anti-caking agents include cream of tartar, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pa.), and tricalcium phosphate. In one embodiment, the anti-caking agent is present in the tabletop sweetener composition in an amount of about 0.001 to about 3% by weight of the tabletop sweetener composition.

[0120] In some embodiments, the sweetener composition of any of the above aspects and embodiments thereof is encapsulated using typical means for encapsulating flavor or fragrance compounds. Non-limiting examples of such techniques are described in U.S. Patent Application Publication Nos. 2016 / 0235102, 2019 / 0082727, 2018 / 0369777, 2018 / 0103667, 2016 / 0346752, 2015 / 0164117, 2014 / 0056836, 2012 / 0027866, 2010 / 0172945 ... No. 2007 / 0128234, and U.S. Patent Nos. 7,488,503, 6,416,799, 5,897,897, 5,786,017, 5,603,971, 4,689,235, 4,610,890, 3,704,137, 3,041,180, and 2,809,895. All of the aforementioned patent publications and patents are incorporated herein by reference as if set forth in their entirety herein.

[0121] Working Example Example 1 - Extraction and characterization Siraitia grosvenorrii extract (60 kg, pale yellow liquid, 3.5% mogroside V) obtained from Gui Lin Layn Natural Ingredients Corp. (Shanghai, China) was dissolved in 150 L of deionized water and loaded onto an XAD macroporous resin. The resin was then eluted with water, 5% aqueous EtOH, and 95% aqueous EtOH, and the last mogroside-rich fraction was collected as Frac1 (5.0 kg). Frac1 was then eluted onto a C18 flash chromatography column (Daiso ODS, 40–70 μm, 100 * The sample was further fractionated on a C18 flash chromatography column (Daiso ODS, 40-70 μm, 100 mm). After loading the sample, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN in water, and 100% ACN at a flow rate of 70 mL / min, and 16 fractions were collected (Frac. 35-50). Frac. 46 (49 g) was eluted on a C18 flash chromatography column (Daiso ODS, 40-70 μm, 100 * 490 mm, 26% ACN aqueous solution, 70 mL / min), Sephadex LH-20 column (55 * 1500 mm, 18% ACN aqueous solution, 0.3~1.5 mL / min), and preparative HPLC (YMC ODS, 5 μm, 10 * Further purification with 250 mm, 14–21% aqueous ACN, 4.5 mL / min) gave (1S,4R,9beta,11alpha,24R)-1-{[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (isomogroside IV E Compound 11a) was obtained (50 mg, purity: 96%).

[0122] By referring to the mass spectrometry and NMR analysis shown in Figures 2 to 4, the compound was found to have the following structure: [ka] was estimated.

[0123] Example 2 - Sensory Test Sensory testing was performed by a group of about five panelists. Samples of the purified compound were tasted at a concentration of 250 ppm in a water base and perceived as having an intense sweetness, about 200-300 times sweeter than sucrose. Panelists also found that the sweetness of isomogroside IV compared to mogroside V was significantly higher than that of isomogroside IV. E The sweetness, licorice flavor, and lingering aftertaste of the tea were evaluated on a scale of 1 to 10. The results are shown in Table 1. As shown in Table 1, the panelists E was perceived as slightly sweeter than mogroside V, with no statistically significant differences in the liquorice taste and lingering aftertaste.

[0124] [Table 1]

Claims

1. For sweetening an edible composition or enhancing the sweetness of an edible composition, a compound of the following formula (I): 【Chemistry 1】 The use of mogroside compounds, which are compounds of the

2. 2. The use according to claim 1, wherein the mogroside compound is present in the edible composition at a concentration ranging from 1 ppm to 1000 ppm.

3. 3. The use according to claim 1 or 2, wherein the edible composition contains one or more additional sweeteners.

4. 4. The use of claim 3, wherein the one or more additional sweeteners are selected from the group consisting of sucrose, fructose, glucose, allulose, sugar alcohols, sucralose, aspartame, acesulfame potassium, cyclamate, steviol glycosides, other mogrosides, and any combination thereof.

5. 5. The use according to any one of claims 1 to 4, wherein the edible composition contains one or more flavor modifying compounds selected from the group consisting of sweetness enhancing compounds, umami enhancing compounds, cooling effect enhancing compounds, sourness reducing compounds, bitterness blocking compounds, taste masking compounds, mouthfeel improving compounds, and combinations thereof.

6. 6. The use according to any one of claims 1 to 5, wherein the edible composition is a food product, optionally containing a filler, a starch, or a combination thereof.

7. The use according to any one of claims 1 to 5, wherein the edible composition is a beverage, optionally containing an aqueous carrier.

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