Sensory modifier
By using the combination of caffeol monoacylglyceric acid and its salt in the steviol glycoside combination, the problem of sweet residue and bitterness is solved, achieving a more rounded sweetness experience and higher concentration application potential.
Patent Information
- Application Number
- JP2025013992
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2019-04-10
- Filing Date
- 2025-01-30
- Publication Date
- 2025-04-11
AI Technical Summary
The presence of sweet residues, bitterness and other adverse sensory properties in the existing steviol glycoside combinations limits its use in high concentration applications.
By adding an effective sensory modulator, in particular a combination of caffeoylquinic acid and its salt, wherein at least 50% of the modulator is in the form of a salt to reduce sweet residue and bitterness.
Effectively reduces the sweet residue and bitterness in the steviol glycoside combination, improves sensory properties, and provides a more rounded sweet experience at high concentrations.
Smart Images

Figure 2025061977000001_ABST
Abstract
Description
[Technical field]
[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application is a continuation of U.S. application Ser. No. 62 / 830,449, filed April 6, 2019, entitled "Sensory Modifiers," U.S. application Ser. No. 62 / 832,269, filed April 10, 2019, entitled "Sensor Modifiers," U.S. application Ser. No. 16 / 373,206, filed April 4, 2019, entitled "Steviol Glycoside Solubility Enhancers," which was published on July 25, 2019 as U.S. Patent Application Publication No. 2019 / 0223481, International Application No. PCT / US2018 / 054691, filed October 5, 2018, entitled "Steviol Glycoside Solubility Enhancers," International Application No. PCT / US2018 / 054691, filed October 6, 2017, entitled "Steviol Glycoside Solubility Enhancers," No. 16 / 374,894, filed on April 4, 2019, entitled "Methods for Making Yerba Mate Compositions," which was published on August 1, 2019 as U.S. Patent Application Publication No. 2019 / 0231834; International Application No. PCT / US2018 / 054688, filed on October 5, 2018, entitled "Methods for Making Yerba Mate Compositions;" U.S. Provisional Application No. 62 / 676,722, filed on May 25, 2018, entitled "Methods for Making Yerba Mate Extract Compositions," which was published on April 3, 2019, entitled "Sensory modifiers and enhancers for making Yerba Mate compositions," This application claims the benefit of U.S. Application No. 16 / 374,422, entitled "Sensory modifier compounds," which was published on July 25, 2019 as U.S. Patent Application Publication No. 2019 / 0223483, and International Application No. PCT / US2018 / 054743, filed October 5, 2018, entitled "Sensory modifier compounds," the entireties of which are incorporated herein by reference. [Background technology]
[0002] Steviol glycosides are a class of sweet-tasting glycosylated diterpene compounds commonly obtained from the leaves of Stevia rebaudiana. A variety of steviol glycosides are known, some of which provide a sugar-like taste profile and are 150-450 times sweeter than sugar. Such compounds are typically characterized by the presence of a single steviol skeleton and different sequences of glycosidic carbohydrate residues at the C13 and C19 positions.
[0003] In recent decades, consumers have increasingly sought low-calorie alternatives to calorie-rich products. Steviol glycosides provide a non-calorie alternative to traditional calorie sweeteners, such as sugar, glucose, sucrose, and / or fructose. However, in some cases, consumers may perceive the sensory and temporal taste profile of steviol glycosides to be somewhat different from traditional calorie sweeteners. For example, existing steviol glycoside compositions may provide a comparable reduced sweetness intensity, increased sweetness linger, increased bitterness, and unfamiliar sensory characteristics, such as astringency and metallic taste, compared to traditional sweeteners. These sensory characteristics may limit the use of steviol glycosides in various consumer products, especially those that seek to use steviol at the highest concentrations. At the same time, consumers favor steviol glycosides as a low-calorie sweetener, in part due to the possibility that such compounds can be obtained naturally from plant sources. Summary of the Invention [Problem to be solved by the invention]
[0004] The present disclosure provides, inter alia, a composition comprising a steviol glycoside component and a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or otherwise improve the sensory properties of the steviol glycoside component. The steviol glycoside component comprises one or more steviol glycosides. The sensory modifier comprises one or more caffeoylquinic acids. A portion of the sensory modifier is in salt form (corresponding to the "salt fraction"), while another portion is in acid form (corresponding to the "acid fraction"). In various embodiments, at least 50% by weight of the sensory modifier is in salt form. The sensory modifier may also be characterized as having a salt fraction that accounts for at least 50% by weight of the entire sensory modifier. Surprisingly, a combination of acid form and salt form has been found to reduce bitterness and reduce sweetness linger, and mixtures with less than 50 mol% salt may not provide the same benefits, and mixtures with more than 90 mol% may provide only a slight reduction in sweetness linger. The disclosure further provides compositions and methods of use thereof.
[0005] For example, the disclosure provides a steviol glycoside composition having reduced sweetness linger, the composition comprising a steviol glycoside component and a sensory modifier in an amount effective to reduce sweetness linger, the sensory modifier comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form.
[0006] The present disclosure also provides a steviol glycoside composition having reduced bitterness, the composition comprising a steviol glycoside component and a sensory modifier in an amount effective to reduce bitterness, the sensory modifier may comprise one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form.
[0007] The disclosure further provides a method for reducing sweetness linger from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component, the sensory modifier comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form.
[0008] The disclosure also provides a method for reducing bitterness from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component, the sensory modifier comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form.
[0009] The present disclosure further provides an aqueous steviol glycoside solution having reduced sweetness linger, the solution comprising steviol glycoside components including at least one of rebaudioside D, rebaudioside M, and rebaudioside A, the total steviol glycoside concentration being between 200 ppm and 1000 ppm, and a sensory modifier at a concentration between 200 ppm and 1000 ppm, the sensory modifier comprising a salt fraction and an acid fraction, the salt fraction being, in one embodiment, monocaffeoylquina. The sensory modifier comprises an acid salt and a salt of dicaffeoylquinic acid, the acid fraction comprising monocaffeoylquinic acid and dicaffeoylquinic acid, the salt fraction comprising 50-80% by weight of the total sensory modifier, at least a portion of which in one embodiment is prepared from yerba mate or stevia, and the aqueous steviol glycoside solution has a reduced sweetness linger compared to an aqueous steviol glycoside solution having the same steviol glycoside component at the same concentration without the sensory modifier.
[0010] The disclosure further provides an aqueous steviol glycoside solution having reduced bitterness, the composition comprising steviol glycoside components including at least one of rebaudioside D, rebaudioside M, and rebaudioside A, the total concentration of the steviol glycoside components being between 400 ppm and 800 ppm, and a sensory modifier at a concentration of between 400 ppm and 800 ppm, the sensory modifier comprising a salt fraction and an acid fraction, the salt fraction being, in one embodiment, a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid. and wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, the salt fraction represents 50-80% by weight of the total sensory modifier, and the acid fraction represents 20-50% by weight of the total sensory modifier, and at least a portion of the total sensory modifier is, in one embodiment, prepared from yerba mate or stevia, and the aqueous steviol glycoside solution has reduced bitterness compared to an aqueous steviol glycoside solution having the same concentration of steviol glycoside components without the sensory modifier.
[0011] Advantages, some of which are unexpected, are achieved by embodiments of the present disclosure. In various embodiments, the use of sensory modifiers described herein improves various sensory properties of a steviol glycoside component compared to the same steviol glycoside component without the sensory modifier. For example, the sensory modifier can provide a rounder taste profile, reduced sweetness linger, a sucrose-like mouthfeel, reduced bitterness, or a combination thereof, compared to the steviol glycoside component alone. In some embodiments, the sensory modifier can suppress undesirable sensory properties specific to Reb M and Reb N, such as astringency, metallic flavor, powdery feel, numbness, or vaporous feel.
[0012] In various embodiments, the use of a sensory modifier having a salt fraction of 50% or more by weight of the sensory modifier has the advantage of providing a reduced bitterness and / or reduced sweetness linger of the steviol glycoside components compared to salt fractions of less than 50% by weight. In further embodiments, the use of a sensory modifier having a salt fraction of 90% or less by weight of the total sensory modifier can provide a reduced sweetness linger compared to the use of a sensory modifier having a salt fraction of more than 90% by weight. [Brief description of the drawings]
[0013] The drawings illustrate generally, by way of example, but not by way of limitation, various embodiments discussed in the present document.
[0014] [Figure 1] FIG. 1 shows the structures of various steviol glycosides.
[0015] [Diagram 2] FIG. 2 shows a simplified titration curve that illustrates, even as a simple example, how changes to the acid and salt fractions do not necessarily relate to changes in pH.
[0016] It should be understood that numerous other modifications and embodiments can be devised by those skilled in the art which fall within the scope and spirit of the principles of this disclosure. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0017] Reference will now be made in detail to certain embodiments of the disclosed subject matter, examples of which are illustrated in part in the accompanying drawings. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the illustrated subject matter is not intended to limit the claims to the disclosed subject matter.
[0018] In this document, the terms "a," "an," or "the" are used to include one or more than one, unless the context clearly dictates otherwise. The term "or" is used to refer to a non-exclusive "or" unless otherwise noted. All publications, patents, and patent documents referenced in this document are incorporated herein by reference in their entirety as if each was individually incorporated by reference. In the event of inconsistent usage between this document and a document so incorporated by reference, the usage in the incorporated references should be construed as supplementary to the usage in this document. In the event of irreconcilable discrepancies, the usage in this document shall control.
[0019] Values expressed in range format should be interpreted flexibly to include not only the numerical values expressly recited as the limits of the range, but also all individual numerical values or subranges subsumed within the range as if each numerical value and subrange were expressly recited. For example, the range "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only exactly about 0.1% to about 5%, but also the individual values (e.g., 1%, 2%, 3% and 4%) and subranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the specified range. Unless otherwise indicated, the statement "about X to Y" has the same meaning as "about X to about Y". Similarly, the statement "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z" unless otherwise indicated.
[0020] Unless expressly stated, ppm (parts per million) are by weight.
[0021] The present disclosure relates to various steviol glycoside compositions having improved sensory properties, such as reduced sweetness linger and / or reduced bitterness. The present disclosure also relates generally to sensory modifiers and uses thereof. In various embodiments, the sensory modifier comprises one or more caffeoyl-substituted quinic acids and salts thereof, and at least 50% by weight of the sensory modifier is in salt form. The present disclosure further relates to methods of reducing undesirable properties associated with various steviol glycoside components to provide improved compositions compared to steviol glycoside compositions that do not include the sensory modifiers described herein. Steviol Glycosides
[0022] The present disclosure provides compositions containing steviol glycoside components and various improvements that serve to modify their sensory perception. The steviol glycoside components of the present disclosure can contain a variety of steviol glycosides.
[0023] The steviol glycoside component can include one or more steviol glycosides. In some embodiments, the term steviol glycoside refers to rebaudioside A (Reb A) (CAS#58543-16-1), rebaudioside B (Reb B) (CAS#58543-17-2), rebaudioside C (Reb C) (CAS#63550-99-2), rebaudioside D (Reb D) (CAS#63279-13-0), rebaudioside E (Reb E) (CAS#63279-14-1), rebaudioside F (Reb F) (CAS#438045-89-7), rebaudioside M (Reb M) (CAS#1220616-44-3), rubusoside (CAS#63849-39-4), dulcoside A (CAS#64432-06-0), rebaudioside I (Reb I) (MassBank Record:FU000332), rebaudioside Q (Reb Q), rebaudioside N (Reb N), rebaudioside O (Reb O), 1,2-stevioside (CAS#57817-89-7), 1,3-stevioside (Reb G), steviol-1,2-bioside (MassBank Record:FU000332). Record:FU000299), steviol-1,3-bioside, steviol-13-O-glycoside (13-SMG), steviol-19-O-glycoside (19-SMG), OPS1-5 (corresponding to compound 4 from WO 2016 / 100689), steviol glycosides including 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more glycosides, and isomers thereof. See Example 1. See also Steviol Glycosides Chemical and Technical Assessment 82nd JECFA, 2016 (prepared by Harriet Wallin, Food Agric. Org.).
[0024] Steviol glycosides generally have the formula shown in Figure 1, where steviol (R1 and R2 = H) is the aglycone backbone and R1 and R2 can each be hydrogen or one or more sugar moieties. These sugar moieties are most commonly glucose, rhamnose, or xylitol, although steviol containing fructose and deoxyglucose sugar moieties have been reported.
[0025] Steviol glycosides are not only structurally different, but various steviol glycosides can also differ in their sensory properties. For example, stevioside (containing three glucose units) and rebaudioside A (containing four glucose units) are found in higher amounts in stevia extracts and have certain sweetness properties. Both stevioside and rebaudioside A add sweetness, but can be perceived as containing bitterness properties, especially at higher concentrations. Rebaudioside A has a bitterness property that increases with concentration and can limit its use at higher concentrations (e.g., above 400 ppm).
[0026] Other steviol glycosides may contain an increased number of glycosides and are found in much smaller amounts in stevia extract. Such compounds may be referred to as "minor" steviol glycosides even when used as major components in the composition. For example, so-called minor steviol glycosides may include rebaudioside D and rebaudioside M, which are found in smaller amounts in stevia extract and contain different sweetness characteristics than the more abundant steviol glycosides. Some of the sweetness characteristics of these minor steviol glycosides may be preferred over the major steviol glycosides. For example, rebaudioside D and rebaudioside M have reduced bitterness characteristics compared to rebaudioside A. These reduced bitterness characteristics of rebaudioside D and rebaudioside M allow for a more favorable sensory experience and allow for their use in higher concentrations. However, although bitterness is reduced in rebaudioside D and rebaudioside M compared to rebaudioside A, bitterness perception can still be limiting, especially at higher concentrations. Other sensory properties can also be limiting, for example, sweetness linger can be limiting in these minor glycosides, especially at higher concentrations. Sweetness linger can be perceived as a sweetness that lingers in the mouth longer than would be expected for a comparable sugar solution. The sweetness linger of minor steviol glycosides can limit their use, especially at higher concentrations.
[0027] As described herein, the addition of a sensory modifier can change the sensory properties of a steviol glycoside composition. Furthermore, the sensory modifier can modify the sensory properties associated with a particular steviol glycoside component. For example, the sensory modifier can surprisingly reduce the sweetness linger in minor steviol glycosides, such as rebaudioside D and rebaudioside M. By reducing the sweetness linger, the sensory modifier allows for a better sensory experience with minor steviol glycosides and allows for the use of minor steviol glycosides at higher concentrations. Thus, the disclosed sensory modifiers can change the sensory properties associated with minor steviol glycosides.
[0028] In some embodiments, minor steviol glycosides may also have certain sensory properties related to sweetness intensity. The perceived sweetness intensity may be reported as SEV (sucrose equivalent value), with increasing sweetness intensity corresponding to a higher SEV. An SEV of 1 corresponds to a 1% sucrose solution, an SEV of 2 corresponds to a 2% sucrose solution, and so on. The perception of sweetness intensity generally increases with increasing concentration of minor steviol glycosides, but the perceived sweetness intensity may reach a plateau despite increasing amounts of minor steviol glycosides. This plateau of sweetness intensity may limit the use of minor steviol glycosides, especially when a higher SEV is desired. It has been found that the addition of sensory modifiers surprisingly increases the perceived sweetness intensity of minor steviol glycosides beyond the plateau normally observed, allowing minor steviol glycosides to be used at higher concentrations than previously used. For example, by combining rebaudioside M with one or more sensory modifiers, a sweetness intensity greater than SEV 11 can be achieved. In various embodiments, increasing concentrations of rebaudioside M with one or more sensory modifiers can achieve increased sweetness intensities up to about SEV 13 at about 1400 ppm rebaudioside M, thus the disclosed sensory modifiers can increase the sweetness intensity associated with minor steviol glycosides beyond that which can be perceived in the absence of the sensory modifier.
[0029] In various embodiments, the steviol glycoside component can include a mixture of two or more steviol glycosides, with one steviol glycoside predominating. For example, the steviol glycoside component can be predominantly rebaudioside M, rebaudioside N, rebaudioside D, or rebaudioside A. The predominant steviol glycoside can comprise at least or about 50%, 60%, 70%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, or 99.5% by weight of the steviol glycoside component.
[0030] The steviol glycoside components can include rebaudioside M, rebaudioside N, rebaudioside D, and rebaudioside A. In some embodiments, one or more of the steviol glycoside components are isolated from Stevia rebaudiana. In some embodiments, one or more of the steviol glycoside components are produced by fermentation with an engineered microorganism or enzymatically produced from plant-derived steviol and further isolated. For example, rebaudioside D and M can be produced by an engineered organism and then isolated to produce primarily rebaudioside D and rebaudioside M steviol glycoside components as the predominant steviol glycoside species. In some embodiments, one or more of the steviol glycosides are produced by bioconversion with enzymes and leaf extracts.
[0031] In other embodiments, steviol glycoside compositions and steviol glycoside components can include rebaudioside D and rebaudioside M in greater amounts than other steviol glycosides.
[0032] Rebaudioside M, rebaudioside D, or both can be present in the steviol glycoside component in a total amount of about 80% (by weight) or more (e.g., RM80), 90% (by weight) or more (e.g., RM90), 95% (by weight) or more (e.g., RM95), or 99% (by weight) or more of the total amount of steviol glycosides in the steviol glycoside component. Rebaudioside M can be the predominant steviol glycoside in the steviol glycoside component, and can be present in an amount ranging from about 50% to about 95%, from about 70% to about 90%, or from about 75% to about 85% of the total amount of steviol glycosides in the steviol glycoside component. Rebaudioside D can be in an amount less than rebaudioside M, such as, for example, in an amount ranging from about 5% to about 25%, about 10% to about 20%, or about 10% to about 15% of the total amount of steviol glycosides in the steviol glycoside composition. For example, the composition can contain primarily rebaudioside M and / or D and can include one or more of rebaudioside A, rebaudioside B, or stevioside in an amount of about 5% (by weight) or less, about 2% (by weight) or less, or about 1% (by weight) or less of the total amount of steviol glycosides in the steviol glycoside composition.
[0033] The steviol glycoside composition can contain various amounts of steviol glycosides. The steviol glycosides can be present in the composition in any amount desired for a particular use. For example, the steviol glycosides can be present in the composition in a total concentration of about 1 ppm to about 1000 ppm or about 1 ppm to about 2000 ppm of steviol glycosides, and such concentrations can be particularly useful when the composition is a beverage or food composition 1. In some embodiments, steviol glycosides may be present in the composition at a total concentration of steviol glycosides of about 100 ppm to about 2000 ppm, about 200 ppm to about 2000 ppm, 300 ppm to about 2000 ppm, 400 ppm to about 2000 ppm, 500 ppm to about 2000 ppm, 600 ppm to about 2000 ppm, 700 ppm to about 2000 ppm, 800 ppm to about 2000 ppm, 900 ppm to about 2000 ppm, or 1000 ppm to about 2000 ppm. In some embodiments, steviol glycosides may be present in the composition at a total concentration of greater than about 10, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 110, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, or 2000 ppm steviol glycosides. In some embodiments, steviol glycosides may be present in the composition at a total concentration of steviol glycosides of about 100 ppm to about 1000 ppm, about 200 ppm to about 1000 ppm, 300 ppm to about 1000 ppm, 400 ppm to about 1000 ppm, 500 ppm to about 1000 ppm, 600 ppm to about 1000 ppm, 700 ppm to about 1000 ppm, 800 ppm to about 1000 ppm, or 900 ppm to about 1000 ppm. In some embodiments, steviol glycosides may be present in the composition at a total concentration of steviol glycosides of about 100 ppm to about 800 ppm, about 200 ppm to about 800 ppm, 300 ppm to about 800 ppm, 400 ppm to about 800 ppm, 500 ppm to about 800 ppm, 600 ppm to about 800 ppm, or 700 ppm to about 800 ppm. In some embodiments, steviol glycosides may be present in the composition at a total concentration of steviol glycosides of about 400 ppm to about 800 ppm.
[0034] The steviol glycoside component can include various amounts of one or more individual steviol glycoside species, each of which can be present at a concentration independently defined for each species. For example, an individual steviol glycoside species can be present in the composition at a concentration of from about 1 ppm to about 1000 ppm or from about 1 ppm to about 2000 ppm. In some embodiments, steviol glycoside species may be present in the composition at a concentration of from about 100 ppm to about 2000 ppm, from about 200 ppm to about 2000 ppm, from 300 ppm to about 2000 ppm, from 400 ppm to about 2000 ppm, from 500 ppm to about 2000 ppm, from 600 ppm to about 2000 ppm, from 700 ppm to about 2000 ppm, from 800 ppm to about 2000 ppm, from 900 ppm to about 2000 ppm, or from 1000 ppm to about 2000 ppm.
[0035] For example, Reb A, Reb M, Reb D, or any combination thereof, when present, can each have a concentration of about 1 ppm to about 1400 ppm, or about 1 ppm to about 1000 ppm. In some embodiments, Reb A, Reb M, Reb D, or any combination thereof, can each be present in the composition at a concentration of about 100 ppm to about 1000 ppm, about 200 ppm to about 1000 ppm, 300 ppm to about 1000 ppm, 400 ppm to about 1000 ppm, 500 ppm to about 1000 ppm, 600 ppm to about 1000 ppm, 700 ppm to about 1000 ppm, 800 ppm to about 1000 ppm, or 900 ppm to about 1000 ppm. In some embodiments, Reb A, Reb M, Reb D, or any combination thereof, may each be individually present in the steviol glycoside composition at a concentration of greater than about 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, or 1000 ppm. In some embodiments, Reb A, Reb M, Reb D, or any combination thereof, may each be individually present in the composition at a concentration of about 100 ppm to about 800 ppm, about 200 ppm to about 800 ppm, 300 ppm to about 800 ppm, 400 ppm to about 800 ppm, 500 ppm to about 800 ppm, 600 ppm to about 800 ppm, or 700 ppm to about 800 ppm. In some embodiments, Reb A, Reb M, Reb D, or any combination thereof may be present in the composition at a concentration of about 400 ppm to about 800 ppm. Sensory Modifiers
[0036] A sensory modifier is a compound or composition that, at a certain amount, changes the sensory characteristics or sensory properties of a sweetened consumable, such as a beverage, food product, etc. Non-limiting examples of sensory characteristics that a sensory modifier can change include bitter, sour, numb, astringent, metallic, too sweet, dry, sweet, the time aspect of sweetness, and flavor impressions, such as licorice, vanilla, prune, cotton candy, and molasses flavor impressions. Sensory modifiers can enhance sensory characteristics, such as enhancing sweetness, suppress sensory characteristics, such as reducing bitterness, or change the time aspect of a sensory characteristic, for example, by reducing sweetness linger, or combinations thereof. In some embodiments, the amount used in a composition having multiple steviol glycosides and one or more sensory modifiers changes at least one sensory characteristic, for example, the combination can have a reduced bitterness or sweetness compared to one or more of the steviol glycosides in the composition, and the sensory characteristics in the resulting composition are better than expected.
[0037] The present disclosure provides, in one embodiment, a sensory modifier comprising one or more caffeoyl-substituted quinic acids and their salts. In various embodiments, the caffeoyl-substituted quinic acids include esters obtained from the carboxylic acid of caffeic acid and the alcohol of quinic acid. "Caffeoyl-substituted quinic acids" or "caffeoylquinic acids" as those terms are used herein include mono-caffeoylquinic acids and dicaffeoylquinic acids and their salts. Mono-caffeoylquinic acids include esters obtained from a single caffeic acid and quinic acid (e.g., chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), and cryptochlorogenic acid (4-O-caffeoylquinic acid)). Dicaffeoylquinic acids include esters derived from two caffeic acids and quinic acid (e.g., 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid). Thus, the sensory modifiers include both the acid and salt forms of caffeoyl-substituted quinic acids. The free acid forms of various caffeoyl-substituted quinic acids are shown in Table 1. [Table 1]
[0038] In various embodiments, the sensory modifier is quinic acid, caffeic acid, ferulic acid, sinapic acid, p-coumaric acid, esters of quinic acid, esters of caffeic acid, esters of ferulic acid, esters of sinapic acid, esters of p-coumaric acid, esters of caffeic acid and quinic acid, esters of caffeic acid and quinic acid containing a single caffeic acid moiety, esters of caffeic acid and quinic acid containing two or more caffeic acid moieties, esters of ferulic acid and quinic acid, esters of ferulic acid and quinic acid containing a single ferulic acid moiety, esters of ferulic acid and quinic acid containing two or more ferulic acid moieties, esters of sinapic acid and quinic acid, esters of a single sinapic acid moiety. and / or one or more of the following: esters of sinapic acid and quinic acid containing one or more sinapic acid moieties, esters of p-coumaric acid and quinic acid, esters of p-coumaric acid and quinic acid containing a single p-coumaric acid moiety, esters of p-coumaric acid and quinic acid containing two or more p-coumaric acid moieties, di-esters of quinic acid containing one caffeic acid moiety and one ferulic acid moiety, caffeic acid esters of 3-(3,4-dihydroxyphenyl)lactic acid, caffeic acid esters of tartaric acid, caffeic acid esters of tartaric acid containing two or more caffeic acid moieties, and / or their isomers, and the corresponding salts.
[0039] In some embodiments, the sensory modifier is chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), cryptochlorogenic acid (4-O-caffeoylquinic acid), 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, 5,6-dicaffeoylquinic acid, 6,7-dicaffeoylquinic acid, 7,8-dicaffeoylquinic acid, 8,9-dicaffeoylquinic acid, 9,10-dicaffeoylquinic acid, 10,11-dicaffeoylquinic acid, 11,12-dicaffeoylquinic acid, 12,13-dicaffeoylquinic acid, 13,14-dicaffeoylquinic acid, 14,15-dicaffeoylquinic acid, 15,16-dicaffeoylquinic acid, 17,18-dicaffeoylquinic acid, 19,19-dicaffeoylquinic acid, 20,21-dicaffeoylquinic acid, 22,23-dicaffeoylquinic acid, 24,25-dicaffeoylquinic acid, 25,26-dicaffeoylquinic acid, 26,27-dicaffeoylquinic acid, 27,28-dicaffeoylquinic acid, 28,29-dicaffeoylquinic acid, 29,30-dicaffeoylquinic acid, 30,31-dicaffeoylquinic acid, 31,32-dicaffeoylquinic acid, 32,33-dicaffeoylquinic acid, 33,34-dicaffeoylquinic acid, 34,35 The active ingredient(s) include one or more of quinic acid, 3-O-feruloyl quinic acid, 4-O-feruloyl quinic acid, 5-O-feruloyl quinic acid, 1,3-diferuloyl quinic acid, 1,4-diferuloyl quinic acid, 1,5-diferuloyl quinic acid, 3,4-diferuloyl quinic acid, 3,5-diferuloyl quinic acid, 4,5-diferuloyl quinic acid, rosmarinic acid, caftaric acid (monocaffeoyl tartaric acid), chicoric acid (dicaffeoyl tartaric acid) and salts, and / or their isomers and the corresponding salts.
[0040] In some embodiments, the sensory modifier consists essentially of one or more compounds selected from the list consisting of chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), cryptochlorogenic acid (4-O-caffeoylquinic acid), 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, and any combinations thereof, their isomers, and corresponding salts. In various embodiments, one or more alcohols of the caffeoyl moiety are replaced with hydrogen or a C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, etc.), C1-C 10 Alkenyl, C6-C 10 Aryl, C2-C 10The caffeic acid moiety is substituted with an acyl, acrylate, caffeoyl, o-coumaroyl, p-coumaroyl, m-coumaroyl, cinnamoyl, 4-hydroxycinnamoyl, feruloyl, iso-feruloyl, sinapoyl, galloyl, sulfate, phosphate, or phosphonate. Thus, the modified and substituted caffeic acid moiety results in cinnamic acid, o-coumaroyl, p-coumaric acid, m-coumaric acid, ferulic acid, and their acyl and ester forms. In various embodiments, one or more alcohols of the quinic acid moiety are C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, etc.), C1-C 10 Alkenyl, C6-C 10 Aryl, C2-C 10 Substituted with acyl, acrylate, caffeoyl, o-coumaroyl, p-coumaroyl, m-coumaroyl, cinnamoyl, 4-hydroxycinnamoyl, feruloyl, iso-feruloyl, sinapoyl, galloyl, sulfate, phosphate, or phosphonate.
[0041] The sensory modifier may include one or more of caffeic acid esters of 3-(3,4-dihydroxyphenyl)lactic acid, caffeic acid esters of tartaric acid, ferulic acid esters of quinic acid, or any other optionally substituted cinnamoyl esters of quinic acid other than caffeoylquinic acid. Examples of ferulic acid esters of quinic acid include 3-O-feruloylquinic acid, 4-O-feruloylquinic acid, 5-O-feruloylquinic acid, 1,3-diferuloylquinic acid, 1,4-diferuloylquinic acid, 1,5-diferuloylquinic acid, 3,4-diferuloylquinic acid, 3,5-diferuloylquinic acid, 4,5-diferuloylquinic acid, and combinations thereof. An example of a caffeic acid ester of 3-(3,4-dihydroxyphenyl)lactic acid is rosmarinic acid. Examples of caffeic acid esters of tartaric acid include chicoric acid (dicaffeoyl tartaric acid) and caftaric acid (monocaffeoyl tartaric acid), and combinations thereof.
[0042] In an alternative embodiment, the sensory modifier is a mixture of one or more of caffeic acid esters of 3-(3,4-dihydroxyphenyl)lactic acid, caffeic acid esters of tartaric acid, ferulic acid esters of quinic acid, or any other optionally substituted cinnamoyl esters of quinic acid other than caffeoylquinic acid. Such sensory modifiers also include their salts, such as those having a salt fraction and an acid fraction. Thus, it is further envisioned that each of the various embodiments described herein relating to caffeoylquinic acid and other sensory modifiers may be equally applicable to this alternative.
[0043] Caffeic acid has the following structure: [ka]
[0044] Quinic acid has the following structure: [ka]
[0045] The structure provided above is D-(-)-quinic acid, and the numbers shown correspond to the current IUPAC numbering.
[0046] In various embodiments, the sensory modifier may be enriched with one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid. The term "enriched" refers to an increase in the amount of one of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid compared to one or more other compounds present in the sensory modifier. Sensory modifiers enriched with one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid can modify the sensory properties of the steviol glycoside component of the composition.
[0047] One or more dicaffeoylquinic acid enriched sensory modifiers can modify the sensory properties of the steviol glycoside composition. The dicaffeoylquinic acid enriched sensory modifiers can contain 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 60% or more, 70% or more, or 80% or more, or 90% or more dicaffeoylquinic acid.
[0048] In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be mono-caffeoylquinic acid and its salts. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be chlorogenic acid (5-O-caffeoylquinic acid) and its salts. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be neochlorogenic acid (3-O-caffeoylquinic acid) and its salts. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifiers may be chlorogenic acid (4-O-caffeoylquinic acid) and its salts.
[0049] In various further embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be 1,3-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be 1,4-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be 1,5-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be 3,4-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be 3,5-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier may be 4,5-dicaffeoylquinic acid and salts thereof.
[0050] The sensory modifier may, for example, have a weight ratio of total monocaffeoylquinic acids and salts to total dicaffeoylquinic acids and salts of from 20:1 to 1:20, such as from 3:1 to 1:20. In various embodiments, the sensory modifier has a weight ratio of monocaffeoylquinic acid and salts thereof:dicaffeoylquinic acid and salts thereof of 15:1 to 1:15, 10:1 to 1:10, 5:1 to 1:5, 3:1 to 1:3, 2:1 to 1:2, 1.5:1 to 1:1.5, 5:1 to 1:1, 3:1 to 1:1, 2:1 to 1:1, 1.5:1 to 1:1.1, 1:1 to 1:20, 1:1 to 1:15, 1:1 to 1:10, 1:5 to 1:20, 1:5 to 1:15, 1:5 to 1:10, 1:2 to 1:20, 1:2 to 1:15, 1:2 to 1:10, 1:2 to 1:5, 1:1 to 1:3, 1:1 to 1:2, or 1:1 to 1:1.5. In some embodiments, the sensory modifier has a greater amount by weight of dicaffeoylquinic acid and salts of dicaffeoylquinic acid compared to the amount of monocaffeoylquinic acid and salts of monocaffeoylquinic acid. In various embodiments, the sensory modifier has a ratio of monocaffeoylquinic acid:dicaffeoylquinic acid (including salts thereof) of about 1:1. Salt Form of Sensory Modifier
[0051] The sensory modifiers provided herein contain a portion that is in salt form (corresponding to the "salt fraction") and a portion that is in acid form (corresponding to the "acid fraction"). In various embodiments, the salt fraction comprises at least 50% by weight of the entire sensory modifier. Thus, the major component of the entire sensory modifier is a compound in salt form.
[0052] Sensory modifiers can contain various types of salts, but typically contain salts that are suitable for ingestion, typically salts derived from alkali metals such as sodium and potassium, alkaline earth metals such as magnesium and calcium, and nitrogen-derived salts such as amino acids.
[0053] As described herein, the sensory modifier contains one or more caffeoyl-substituted quinic acids, as well as salt forms thereof. The salt of each caffeoyl-substituted quinic acid may be a lithium, sodium, potassium, magnesium, calcium, ammonium salt, or a mixture of any combination thereof. In various embodiments, the salt of each caffeoyl-substituted quinic acid is a sodium salt, a potassium salt, or a mixture of any combination thereof. Thus, the sensory modifier may include a sodium salt of mono-caffeoylquinic acid, a sodium salt of dicaffeoylquinic acid, a potassium salt of mono-caffeoylquinic acid, a potassium salt of dicaffeoylquinic acid, or a mixture of any combination thereof. For example, the sensory modifier may include the sodium and / or potassium salts of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, or any combination thereof.
[0054] In various embodiments, the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the total sensory modifier is in the salt form.
[0055] For example, at least or about 50%, 55%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 80%, 85%, or at least or about 90% by weight of the total sensory modifier is in salt form. In further embodiments, about 60%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85% or less, or about 90% or less, by weight of the total sensory modifier is in salt form. In still further embodiments, about 50% to 90%, 50% to 80%, 50% to 75%, 60% to 90%, 60% to 80%, 60% to 79%, 60% to 77%, 60% to 75%, 60% to 73%, 60% to 70%, 65% to 80%, 65% to 75%, 66% to 74%, 67% to 73%, 68% to 72%, 69% to 71%, 65% to 70%, 67% to 72%, 69% to 74%, or 70% to 75% by weight of the total sensory modifier is in salt form.
[0056] For example, at least or about 50%, 55%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 80%, 85%, or at least or about 90% by weight of the total salts of caffeoylquinic acids and caffeoylquinic acids are in salt form. In further embodiments, about 60%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85% or less, or about 90% or less, by weight of the total salts of caffeoylquinic acids and caffeoylquinic acids is in salt form. In still further embodiments, about 50% to 90%, 50% to 80%, 50% to 75%, 60% to 90%, 60% to 80%, 60% to 79%, 60% to 77%, 60% to 75%, 60% to 73%, 60% to 70%, 65% to 80%, 65% to 75%, 66% to 74%, 67% to 73%, 68% to 72%, 69% to 71%, 65% to 70%, 67% to 72%, 69% to 74%, or 70% to 75% by weight of the total salts of caffeoylquinic acids and caffeoylquinic acids are in salt form. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.
[0057] As used herein, "salt form" refers to an anionic form of an ionizable compound that forms an ion pair with a cation other than a hydrogen ion, such as a metal cation or a cationic ammonium compound. + , or the ammonium compound NR4 + Ionic coordination with carboxylate-COO -where each R is H or alkyl. For example, in the solid state, the carboxylate may be bound to the cation through an ionic bond. Without being limited by theory, in solution, the ionic species may be tightly paired as a close ion pair or may be separated and solvated. However, when the dissolved salt form anion is isolated from the solution, it is removed together with its paired cationic species. For example, when a salt form of a carboxylic acid is removed from a solution, the resulting compound is a metal carboxylate or other ionic compound. In various embodiments, the salt form is an alkali salt, such as a sodium or potassium salt of one or more quinic acids. One of the differences between the salt form and the acid form is that the isolation of the salt form typically results in an ionic compound that contains a metal cation, while the isolation of the acid form typically results in a neutral species that does not contain a metal cation. The salts and salt forms described herein may include mixed salts. Mixed salts include mixtures of two or more cationic species that share a common anionic partner, such as mixed potassium and sodium salts of caffeoylquinic acid.
[0058] As used herein, "acid form" refers to a carboxylic acid compound having a carboxylic acid group, -COOH. In solution, the -COOH can deprotonate to provide an ionized but non-metalated carboxylate group paired with a proton or protonated species. Thus, the acid form can be represented by -COOH, or H + Paired with -COO - For example, the dissolved acid form may provide a carboxylate that is electrically balanced by hydronium or other protonated solvent species, but the counterion is other than a metal cation or ammonium salt. In the solid state, the acid form may be characterized as a neutral, fully covalently bonded species.
[0059] In further examples, at least or about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or at least or about 45% by weight of the total sensory modifier is in acid form, in further embodiments, about 10%, 15%, 20%, 25%, 30%, 35%, 40% (or less), or less than about 50% by weight of the total sensory modifier is in acid form. In still further embodiments, between 5% and 50% by weight, between 10% and 50% by weight, between 15% and 50% by weight, between 20% and 50% by weight, between 5% and 40% by weight, between 10% and 40% by weight, between 15% and 40% by weight, between 20% and 40% by weight, between 5% and 35% by weight, between 10% and 35% by weight, between 15% and 35% by weight, between 20% and 35% by weight, between 5% and 30% by weight, between 10% and 30% by weight, between 15% and 30% by weight, between 20% and 30% by weight, between 5% and 20% by weight, between 10% and 20% by weight, between 15% and 20% by weight, between 5% and 15% by weight, between 10% and 15% by weight, or between 5% and 10% by weight of the total sensory modifier is in acid form.
[0060] In further examples, at least or about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or at least or about 45% by weight of the total of the salts of caffeoylquinic acids and the caffeoylquinic acids is in the acid form. In further embodiments, about 10%, 15%, 20%, 25%, 30%, 35%, 40% (or less), or less than about 50% by weight of the total of the salts of caffeoylquinic acids and the caffeoylquinic acids is in the acid form. In still further embodiments, 5% to 50% by weight, 10% to 50% by weight, 15% to 50% by weight, 20% to 50% by weight, 5% to 40% by weight, 10% to 40% by weight, 15% to 40% by weight, 20% to 40% by weight, 5% to 35% by weight, 10% to 35% by weight, 15% to 35% by weight, 20% to 35% by weight, 5% to 30% by weight, 10% to 30% by weight, 15% to 30% by weight, 20% to 30% by weight, 5% to 20% by weight, 10% to 20% by weight, 15% to 20% by weight, 5% to 15% by weight, 10% to 15% by weight, or 5% to 10% by weight of the total of the salts of caffeoylquinic acids and the caffeoylquinic acids is in acid form. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.
[0061] In various embodiments, the sensory modifier comprises a salt fraction and an acid fraction, the salt fraction comprises one or more of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid, the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, and the salt fraction comprises at least 50% by weight of the total sensory modifier.
[0062] For example, the salt fraction comprises at least or about 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, or at least or about 90% by weight of the total sensory modifier. In further embodiments, the salt fraction comprises about 60%, 65%, 70%, 75%, 80%, 85% or about 90% by weight of the total sensory modifier. In still further embodiments, the salt fraction comprises 50%-90%, 50%-80%, 50%-75%, 60%-90%, 60%-80%, 65%-80%, or 65%-75% by weight of the total sensory modifier. Unless otherwise specified, the weight percentage of the salt fraction should be calculated including the equilibrium cationic species.
[0063] In further examples, the salt fraction comprises at least or about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or at least or about 45% by weight of the total sensory modifier. In further embodiments, the acid fraction comprises about 10%, 15%, 20%, 25%, 30%, 35%, 40% (or less), or less than about 50% by weight of the total sensory modifier. In still further embodiments, the acid fraction comprises 5% to 50%, 10% to 50%, 15% to 50%, 20% to 50%, 5% to 40%, 10% to 40%, 15% to 40%, 20% to 40%, 5% to 35%, 10% to 35%, 15% to 35%, 20% to 35%, 5% to 30%, 10% to 30%, 15% to 30%, 20% to 30%, 5% to 20%, 10% to 20%, 15% to 20%, 5% to 15%, 10% to 15%, or 5% to 10% by weight of the total sensory modifier.
[0064] As another example, the salt fraction comprises at least or about 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, or at least or about 90% by weight of the total of the salts of caffeoylquinic acids and caffeoylquinic acids. In further embodiments, the salt fraction comprises about 60%, 65%, 70%, 75%, 80%, 85%, or about 90% by weight of the total of the salts of caffeoylquinic acids and caffeoylquinic acids. In still further embodiments, the salt fraction comprises 50%-90%, 50%-80%, 50%-75%, 60%-90%, 60%-80%, 65%-80%, or 65%-75% by weight of the total of the salts of caffeoylquinic acids and caffeoylquinic acids. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.
[0065] The sensory modifier may also be characterized as having at least 50 mol% of the total sensory modifier in salt form. For example, at least or about 50 mol%, 55 mol%, 60 mol%, 65 mol%, 70 mol%, 75 mol%, 80 mol%, 85 mol%, or at least or about 90 mol% of the total sensory modifier is in salt form. In further embodiments, about 60 mol%, 65 mol%, 70 mol%, 75 mol%, 80 mol%, 85 mol% (or less), or about 90 mol% (or less) of the total sensory modifier is in salt form. In still further embodiments, 50 mol% to 90 mol%, 50 mol% to 80 mol%, 50 mol% to 75 mol%, 60 mol% to 90 mol%, 60 mol% to 80 mol%, 60 mol% to 75 mol%, 60 mol% to 70 mol%, 65 mol% to 80 mol%, or 65 mol% to 75 mol% of the total sensory modifier is in salt form.
[0066] In further examples, at least or about 5 mol%, 10 mol%, 15 mol%, 20 mol%, 25 mol%, 30 mol%, 35 mol%, 40 mol%, or at least or about 45 mol% of the total sensory modifier is in acid form, in further embodiments, about 10 mol%, 15 mol%, 20 mol%, 25 mol%, 30 mol%, 35 mol%, 40 mol% (or less), or less than about 50 mol% of the total sensory modifier is in acid form. In still further embodiments, 5 mol% to 50 mol%, 10 mol% to 50 mol%, 15 mol% to 50 mol%, 20 mol% to 50 mol%, 5 mol% to 40 mol%, 10 mol% to 40 mol%, 15 mol% to 40 mol%, 20 mol% to 40 mol%, 5 mol% to 35 mol%, 10 mol% to 35 mol%, 15 mol% to 35 mol%, 20 mol% to 35 mol%, 5 mol% to 30 mol%, 10 mol% to 30 mol%, 15 mol% to 30 mol%, 20 mol% to 30 mol%, 5 mol% to 20 mol%, 10 mol% to 20 mol%, 15 mol% to 20 mol%, 5 mol% to 15 mol%, 10 mol% to 15 mol%, or 5 mol% to 10 mol% of the total sensory modifier is in acid form.
[0067] In yet further examples, the sensory modifier is at least 50 mol% of the total of the salt of caffeoylquinic acid and the caffeoylquinic acid. For example, at least or about 50 mol%, 55 mol%, 60 mol%, 65 mol%, 70 mol%, 75 mol%, 80 mol%, 85 mol%, or at least or about 90 mol% of the salt of caffeoylquinic acid and the caffeoylquinic acid are in salt form. In further embodiments, about 60 mol%, 65 mol%, 70 mol%, 75 mol%, 80 mol%, 85 mol% (or less), or about 90 mol% (or less) of the total of the salt of caffeoylquinic acid and the caffeoylquinic acid are in salt form. In still further embodiments, between 50 mol% and 90 mol%, between 50 mol% and 80 mol%, between 50 mol% and 75 mol%, between 60 mol% and 90 mol%, between 60 mol% and 80 mol%, between 60 mol% and 75 mol%, between 60 mol% and 70 mol%, between 65 mol% and 80 mol%, or between 65 mol% and 75 mol% of the total salts of caffeoylquinic acids and caffeoylquinic acids are in salt form, in some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.
[0068] Similarly, the salt fraction may be characterized in terms of mole percent rather than weight percent. In various embodiments, for example, the salt fraction comprises at least or about 50 mole%, 55 mole%, 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or at least or about 90 mole% of the total sensory modifier. In further embodiments, the salt fraction comprises about 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole% or about 90 mole% or less of the total sensory modifier. In still further embodiments, the salt fraction comprises 50 mole%-90 mole%, 50 mole%-80 mole%, 50 mole%-75 mole%, 60 mole%-90 mole%, 60 mole%-80 mole%, 65 mole%-80 mole%, or 65 mole%-75 mole% of the total sensory modifier.
[0069] In further examples, the acid fraction comprises at least or about 5 mol%, 10 mol%, 15 mol%, 20 mol%, 25 mol%, 30 mol%, 35 mol%, 40 mol%, or at least or about 45 mol% of the total sensory modifier. In further embodiments, the acid fraction comprises about 10 mol%, 15 mol%, 20 mol%, 25 mol%, 30 mol%, 35 mol%, 40 mol% (or less), or less than about 50 mol% of the total sensory modifier. In still further embodiments, the acid fraction constitutes 5 mol% to 50 mol%, 10 mol% to 50 mol%, 15 mol% to 50 mol%, 20 mol% to 50 mol%, 5 mol% to 40 mol%, 10 mol% to 40 mol%, 15 mol% to 40 mol%, 20 mol% to 40 mol%, 5 mol% to 35 mol%, 10 mol% to 35 mol%, 15 mol% to 35 mol%, 20 mol% to 35 mol%, 5 mol% to 30 mol%, 10 mol% to 30 mol%, 15 mol% to 30 mol%, 20 mol% to 30 mol%, 5 mol% to 20 mol%, 10 mol% to 20 mol%, 15 mol% to 20 mol%, 5 mol% to 15 mol%, 10 mol% to 15 mol%, or 5 mol% to 10 mol% of the total sensory modifier.
[0070] The sensory modifier may have, for example, a weight or molar ratio of acid:salt of 1:1 to 1:9, 1:1 to 1:8, 1:1 to 1:7, 1:1 to 1:6, 1:1 to 1:5, 1:1 to 1:4, 1:1 to 1:3, 1:1 to 1:2, or 1:1 to 1:1.5.
[0071] The various mole %, weight %, weight ratios, molar ratios of the salt fractions and salt forms described herein may relate to the sensory modifier as a whole, or in various embodiments, to a portion of the sensory modifier, such as the caffeoylquinic acid moiety, the monocaffeoylquinic acid moiety, the dicaffeoylquinic acid moiety (together with the corresponding salt).
[0072] The salt fraction, which is the mole % and weight % of the salt form of the total sensory modifier, can be determined via a variety of techniques available to one of skill in the art. For example, the salt fraction, which is the mole % and weight % of the total sensory modifier, can be determined spectroscopically (e.g., NMR or ICP-MS), experimentally (e.g., via titration), or by calculation after determining the amount of each component added to the sensory modifier.
[0073] Each of the quinic acids described herein, including each of the monocaffeoylquinic acids and dicaffeoylquinic acids, can be considered a weak acid and can exist in at least one of their conjugate acid form, conjugate base form (e.g., their salt form), and mixed conjugate acid-conjugate base form in which a fraction (e.g., molar fraction) of the compound is in the conjugate acid form and another fraction is in the conjugate base form. The fraction of the conjugate acid form to the conjugate base form for the monocaffeoylquinic acids and dicaffeoylquinic acids depends on various factors, including the pKa of each compound and the pH of the composition.
[0074] In various embodiments, for example, in an aqueous solution, the salt form of the whole sensory modifier exists in equilibrium with the acid form. For example, a particular salt form molecule can be protonated and thus converted to the acid form, and an acid form molecule can be deprotonated to yield the salt form. After approaching or achieving equilibrium, such interactions do not substantially change the overall weight percentage of a given form or fraction of the whole sensory modifier. For example, a composition having a salt fraction of 50% or more by weight of the whole sensory modifier can maintain the same proportions of salt and acid fractions, even though various compounds may exchange from one fraction to another.
[0075] In some cases, the equilibrium between the salt and acid forms may shift in response to the addition of components to the composition. For example, the addition of a buffer, salt, acid, or base can shift the equilibrium in favor of the salt or acid fraction, thus changing the weight percentage of the composition.
[0076] Furthermore, there may be a relationship between the pH of a composition and the ratio of salt fraction to acid fraction. For example, the salt fraction typically increases as the pH increases and typically decreases as the pH decreases. However, as shown in the titration curve of FIG. 2, pH is a different concept from salt fraction and acid fraction. This is clearly evident in the buffer region of the titration curve, where a proportionally large change in the concentration of base (or acid) results in a very minimal or negligible change in pH. For example, an increase in the concentration of alkali does not cause a significant increase in pH unless it begins to move outside the buffer region. The titration curve of FIG. 2 is simplified, and compositions with two or more ionizable components have more complex titration curves. The buffer region is centered around a pH that corresponds to the various pKa values of the titrated compound or mixture. For reference, the pKa of quinic acid is about 3.46, but the pKa of some quinic acid derivatives may be lower. Citric acid, a common buffer, has pKa values of about 3.10, 4.80, and 5.40 for pKa1, pKa2, and pKa3, respectively. In various embodiments, the composition provides a buffer solution at a pH in the center of the buffer region of various caffeoylquinic acid compounds, such as about 1 to about 4, about 1 to about 3, about 2 to about 4, about 3 to about 4, about 2 to about 3, about 2.5 to about 3.5, about 2.4 to about 3.6, about 2.2 to about 3, about 2.4 to about 3, about 2.6 to about 3, about 2.2 to about 3.2, about 2.4 to about 3. The composition may have a pH of about 2.2, about 2.6 to about 3.2, about 2.4 to about 3.4, about 2.4 to about 3.2, about 2.6 to about 3.0, about 2.6 to about 3.4, about 2.2 to about 2.9, about 2.3 to about 3.1, about 2.4 to about 3.2, about 2.5 to about 2.9, about 2.5 to about 3, about 2.6 to about 2.8, about 2.5 to about 2.7, or about 2.7 to about 2.9. For example, the pH can be about 2.2, about 2.3, about 2.4, about 2.5, about 2.6, about 2.7, about 2.8, about 2.9, about 3.0, about 3.1, or about 3.2. In various other embodiments, the pH can be about 3.2 to about 3.8, about 3.3 to about 3.7, about 3.3 to about 3.6, about 3.4 to about 3.7, about 3.4 to about 3.6, about 3.4 to about 4, about 3.4 to about 3.9, about 3.4 to about 3.8, about 3.4 to about 3.7, or about 3.4 to about 3.6.
[0077] In further embodiments, the composition has a pH of about 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3.0, 2.9, 2.8, 2.7, 2.6, or 2.5 (or less). In still further embodiments, the composition has a pH of about 0.5, 0.75, 1, 1.5, 1.7, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, or 3.7 (or more). The pH value can be measured, for example, by an ISFET (Ion Specific Field Effect Transistor) meter.
[0078] In various other embodiments, the composition has a pH greater than the pH at the half-equivalence point or Ka of the total sensory modifier.
[0079] In various other embodiments, the composition has a pH that is lower than the pH at the equivalence point of the total sensory modifier.
[0080] In various other embodiments, for example in a solid composition, the salt form and the acid form may be in the solid state and the ratio between the salt form and the acid form may not change. It should be understood that in various embodiments, the ratio of the salt fraction to the acid fraction in a solid composition, such as a granular tabletop sweetener, may differ from that of the resulting solution to which the solid composition is added. For example, in some embodiments, a solid-state steviol glycoside composition, upon dissolution, results in a solution having at least 50% by weight of the sensory modifier in the salt form. Effective amount of sensory modifier
[0081] The sweetness temporal profile of sucrose is considered highly desirable. The sweetness of some non-nutritive sweeteners, including rebaudioside A, is considered "sharper" than sucrose in that it has a slower or longer sweetness onset. For example, it has a longer onset time before any sweetness is perceived, followed by a rapid increase to maximum sweetness. Such a slow onset sweetener may also be called "sharp". In contrast, sucrose has a shorter onset but a less rapid increase to maximum sweetness, which may be called "rounded". Some non-nutritive sweeteners may have a sweetness that lasts longer than sucrose, i.e., the flavor takes longer to fade from peak sweetness to a level where sweetness is no longer perceived. Sweetener compositions that have a sweetness temporal profile closer to that of sucrose are considered more desirable.
[0082] The compositions of the present disclosure include a sensory modifier in an amount effective to modify the sensory properties of one or more steviol glycosides in the steviol glycoside component. For example, the sensory properties may be modified to more closely approximate the sensory profile of sucrose. In various embodiments, the sensory modifier is present in an amount effective to reduce the sweetness linger of the steviol glycosides, reduce the bitterness, or both.
[0083] A sensory panel can be used to quantify the amount of sensory modifier that is effective in reducing bitterness, reducing sweetness linger, or both. A sensory panel is a scientific and reproducible method that is essential to the food science industry. A sensory panel includes a group of three or more individual panelists. Panelists can be trained, experienced, or even skilled evaluators, but typically, panelists are not consumers or inexperienced evaluators for whom standards have not yet been established. Panelists are trained according to industry-recognized practices to avoid the influence of personal subjectivity and enhance reproducibility. For example, panelists evaluate the objective sensory characteristics of the test products, but typically do not provide subjective characteristics such as personal preferences. In various embodiments, a sensory panel can be conducted in a round table format with three, four, five, or more panelists, who discuss and evaluate each sensory characteristic and reach a consensus on the terminology and characteristics of each sample. The panel can provide a numerical scale to describe each characteristic. For example, zero may correspond to the absence of a characteristic, while another number, such as six, represents the extreme occurrence of the upper limit of the characteristic. The roundtable format may further include a panel leader who directs discussion of terminology and instructs the panel to evaluate specific products and characteristics.
[0084] For example, a sensory panel or assay can be performed to characterize the sensory properties of steviol glycoside compositions with various salt fractions of sensory modifiers. The sensory properties of the solutions can be tested by a panel of at least three, but preferably four or more, individuals with experience in tasting steviol glycoside compositions. The experienced panelists have experience tasting steviol glycosides and are familiar with the sensory properties of individual steviol glycosides and steviol glycoside blends, including sweetness linger and bitterness. These experienced panelists are also familiar with tasting steviol glycosides compared to a control sucrose solution. The experienced panelists can use a round table method to evaluate each sweetness attribute. For example, to test each solution, the experienced panelists can dispense about 2 mL of each solution into their mouth by a full volume pipette, disperse the solution by moving their tongue, and record the value of the particular sweetness attribute being tested. For each sweetness attribute, the panelists should agree on a descriptive scale for each sweetness attribute and then record the value of each sweetness attribute for this. If multiple solutions are tested during a session, the panelists can wash the palate with water. For example, the round table evaluation of sweetness linger can assign a scale of 0 to 6, with a score of 0 indicating no sweetness linger and a score of 6 indicating extreme sweetness linger. The round table evaluation of bitterness can assign a scale of 0 to 6, with a score of 0 indicating no sweetness linger and a score of 6 indicating extreme sweetness linger (0=none, 1=trace, 2=slight, 3=moderate, 4=definite, 5=strong, 6=extreme).
[0085] As a further example, the sweetness intensity of the solutions can be tested by a panel of at least four individuals experienced in tasting steviol glycoside compositions. Panelists can use a standard range of 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, and 14% sucrose solutions, which correspond to SEVs of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, and 14. To test each solution, an experienced panelist dispenses approximately 2 mL of each solution into their mouth with a full volume pipette, disperses the solution by moving their tongue, and records the SEV value of each solution based on a comparison to the 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, and 14% sucrose solutions. Between tasting solutions, panelists may rinse their palates with water. Panelists may also taste a standard range of 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, and 14% sucrose solutions at their discretion between tastings of the test solutions to ensure accurate agreement with the SEV values they recorded with the standard sucrose solutions.
[0086] The panelists may be trained panelists. Trained panelists are trained to understand the terms and sensory phenomena related to the sensory characteristics of the test products. For example, a trained panelist for testing a steviol glycoside composition will understand the terms and sensory phenomena of bitterness, sweetness linger, astringency, typical rebaudioside M and rebaudioside N phenomenon, mouthfeel, tea / floral / green, and sharp-rounded sensations that can be caused by the steviol glycoside composition. In various embodiments, the trained panelists are trained on reference samples corresponding to bitterness, sweetness linger, astringency, typical rebaudioside M and rebaudioside N phenomenon, mouthfeel, tea / floral / green, and sharp-rounded sensations, and are therefore conditioned to recognize and evaluate such criteria. Trained panelists have sufficient acuity to distinguish between the magnitude and nuances of various sensations.
[0087] A control sample is typically used as a reference point or for comparison purposes. For example, a control sample may be used to qualify the effectiveness of a sensory modifier. A control sample may be a composition such as a solution that includes a steviol glycoside component but without the sensory modifier present. Other than the sensory modifier, the control sample should be otherwise identical and contain the same steviol glycoside component at the same concentration. Other standard samples, such as standard samples used to evaluate the intensity of sensory attributes, are commonly used in sensory panels. In other embodiments, the control sample may be a modified control sample that contains a different sensory modifier, such as a competing sensory modifier, an all-acid form sensory modifier, or an all-salt form sensory modifier, for comparison purposes.
[0088] The present disclosure is not limited to sensory testing by experienced or trained panelists. For example, untrained panelists can be used. However, in the case of untrained panelists, a larger number of panelists are needed to provide reproducible results, which typically focus on subjective attributes such as preference.
[0089] Illustrative sensory assays and testing criteria for further sensory characteristics are described in the Examples provided in this disclosure.
[0090] Further description of round table sensory panels and sensory testing is described in International Application No. PCT / US2018 / 054743, published April 11, 2019 as WO 2019 / 071220, International Application No. PCT / US2018 / 054691, published April 11, 2019 as WO 2019 / 071182, U.S. Application No. 16 / 373,206, published July 25, 2019 as U.S. Patent Application Publication No. 2019 / 0223481, and U.S. Application No. 16 / 374,422, published July 25, 2019 as U.S. Patent Application Publication No. 2019 / 0223483, each of which is incorporated herein by reference in its entirety.
[0091] In some embodiments, the amount of sensory modifier effective to reduce sweetness linger can be an amount effective to reduce a sweetness linger score by at least 1 unit, where the sweetness linger score is determined by at least four panelists trained in tasting steviol glycoside solutions using a round table method using a scale of 0 to 6, with a score of 0 indicating no sweetness linger and a score of 6 indicating extreme sweetness linger. In other embodiments, the amount effective to reduce sweetness linger includes an amount effective to reduce a sweetness linger score by at least 1 unit, 2 units, 3 units, 4 units, 5 units, or 6 units. In other embodiments, the amount effective to reduce sweetness linger includes an amount effective to reduce a sweetness linger score to less than 5, 4, 3, 2, or 1 unit. In some embodiments, the amount effective to reduce sweetness linger includes an amount effective to reduce a sweetness linger score to zero.
[0092] The composition can have various amounts of the sensory modifier. The sensory modifier can be present in the composition in any amount desired for a particular use. For example, the sensory modifier can be present in the composition at a total concentration of about 1 ppm to about 1000 ppm or about 1 ppm to about 2000 ppm. In some embodiments, the sensory modifier can be present in the composition at a total concentration of about 100 ppm to about 2000 ppm, about 200 ppm to about 2000 ppm, 300 ppm to about 2000 ppm, 400 ppm to about 2000 ppm, 500 ppm to about 2000 ppm, 600 ppm to about 2000 ppm, 700 ppm to about 2000 ppm, 800 ppm to about 2000 ppm, 900 ppm to about 2000 ppm, or 1000 ppm to about 2000 ppm. In some embodiments, the sensory modifiers may be present in the composition at a total concentration greater than about 10, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 110, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, or 2000 ppm. In various embodiments, the sensory modifier may be present in the composition at a total concentration of from about 100 ppm to about 1000 ppm, from about 200 ppm to about 1000 ppm, from 300 ppm to about 1000 ppm, from 400 ppm to about 1000 ppm, from 500 ppm to about 1000 ppm, from 600 ppm to about 1000 ppm, from 700 ppm to about 1000 ppm, from 800 ppm to about 1000 ppm, or from 900 ppm to about 1000 ppm. In some embodiments, the sensory modifier may be present in the composition at a total concentration of about 100 ppm to about 800 ppm, about 200 ppm to about 800 ppm, 300 ppm to about 800 ppm, 400 ppm to about 800 ppm, 500 ppm to about 800 ppm, 600 ppm to about 800 ppm, or 700 ppm to about 800 ppm. In some embodiments, the sensory modifier may be present in the composition at a total concentration of about 400 ppm to about 800 ppm.
[0093] The amount of each sensory modifier in the various compositions described herein may vary independently. For example, monocaffeoylquinic acid, dicaffeoylquinic acid, or both may each be present in the composition at a concentration of about 1 ppm to about 1000 ppm, individually. In some embodiments, monocaffeoylquinic acid, dicaffeoylquinic acid, or both may each be present at a concentration of about 100 ppm to about 1000 ppm, about 200 ppm to about 1000 ppm, 300 ppm to about 1000 ppm, 400 ppm to about 1000 ppm, 500 ppm to about 1000 ppm, 600 ppm to about 1000 ppm, 700 ppm to about 1000 ppm, 800 ppm to about 1000 ppm, or 900 ppm to about 1000 ppm, individually. In some embodiments, the monocaffeoylquinic acid, dicaffeoylquinic acid, or both may each be present individually at a concentration of greater than about 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, or 1000 ppm. In some embodiments, the monocaffeoylquinic acid, dicaffeoylquinic acid, or both may each be present individually in the composition at a concentration of about 100 ppm to about 800 ppm, about 200 ppm to about 800 ppm, 300 ppm to about 800 ppm, 400 ppm to about 800 ppm, 500 ppm to about 800 ppm, 600 ppm to about 800 ppm, or 700 ppm to about 800 ppm. In some embodiments, the monocaffeoylquinic acids, dicaffeoylquinic acids, or both may each be present in the composition individually at a concentration of from about 400 ppm to about 800 ppm.
[0094] Botanical Sources of Sensory Modifiers In various embodiments, the sensory modifiers may be isolated from a botanical source. A variety of botanical sources contain sensory modifiers, and the sensory modifiers may be isolated from these botanical sources. Some examples of plant sources from which sensory modifiers may be isolated include eucommia ulmoides, honeysuckle, nicotiana benthamiana, artichoke, globe artichoke, cardoon, stevia rebaudiana, monk fruit, coffee, coffee bean, green coffee bean, tea, white tea, yellow tea, green tea, oolong tea, black tea, black tea, fermented tea, bamboo, heather, sunflower, blueberry, cranberry, bilberry, grouseberry, hydrangea, lingonberry, cowberry, huckleberry, grape, chicory, Echinacea purpurea, Echinacea, Eastern pellitory-of-the-wall, Upright pellitory, Lichwort, Greater celandain, celandine, Tetterwort, Nipplewort, Swallowwort, Bloodroot, Common Nettle, Stinging Nettle, Potato, Potato Leaf, Eggplant, Aubergine, Tomato, Cherry Tomato, Bitter Apple, Hawthorn Berry, Sweet Potato, Apple, Peach, Nectarine, Cherry, Sour Cherry, Wild Cherry, Apricot, Almond, Plum, Prune, Holly, Yerba Mate, Yerba Mate Tea, Guayusa, Yaupon Holly, Kuding Tea, Guarana, Cocoa, Cocoa Bean, Cacao, Cocoa Bean, Kola Nut, Kola Tree, Kola Nut, Kola Tree, Ostrich Fern, Fiddlehead Fern, Shuttlecock Fern fern, Oriental ostrich fern, Asian osmanthus, osmanthus, Bracken, Brake, Common bracken, Eagle fern, Eastern bracken fernbrakenfern, Clove, Cinnamon, Indian bay leaf, Nutmeg, Bay laurel, Bay leaf, Basil, Great basil, St. Joseph's wort, Thyme, Sage, Garden sage, Common sage, Culinary sage, Rosemary, Oregano, Wild marjoram, Marjoram, Sweet marjoram, Knotted marjoram, Pot marjoram, Dill, Anise, Star anise, Fennel, Florence fennel, Tarragon, Estragon, Artemisia vulgaris, Licorice, Liquorice, Soy, Soybean, Soyabean, Soya vean, Wheat, Common wheat, Rice, Canola, Broccoli, Cauliflower, Cabbage, Bok choy, Kale, Collard greens, Brussels sprouts, Kohlrabi, Winter's bark bark, elderflower, assa-peixe, greater burdock, valerian, and chamomile.
[0095] Some plant sources may produce sensory modifiers that are enriched in one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid. For example, sensory modifiers isolated from the yerba mate plant (Ilex paraguariensis) are enriched in monocaffeoylquinic acid and dicaffeoylquinic acid. In other aspects, sensory modifiers isolated from yerba mate plants enriched in dicaffeoylquinic acid may contain 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, 60% or more, 70% or more, or 80% or more, or 90% or more of one or more combinations of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, and salts thereof. For example, sensory modifiers isolated from other plant sources may be enriched in dicaffeoylquinic acid. In other aspects, sensory modifiers isolated from other plant sources enriched in dicaffeoylquinic acid may comprise one or more combinations of 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, 60% or more, 70% or more, or 80% or more, or 90% or more of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, and salts thereof.
[0096] The sensory modifiers may be isolated in a variety of ways. Some suitable processes are described in U.S. Application No. 16 / 373,206, filed April 4, 2019, entitled "Steviol Glycoside Solubility Enhancers" (published July 25, 2019 as U.S. Patent Application Publication No. 2019 / 0223481), International Application No. PCT / US2018 / 054691, filed October 5, 2018, entitled "Steviol Glycoside Solubility Enhancers," U.S. Provisional Application No. 62 / 569,279, filed October 6, 2017, entitled "Steviol Glycoside Solubility Enhancers," U.S. Provisional Application No. 62 / 569,279, filed April 4, 2019, entitled "Methods for Making Yerba Mate No. 16 / 374,894 (published on August 1, 2019 as U.S. Patent Application Publication No. 2019 / 0231834), entitled "Methods for Making Yerba Mate Compositions," International Application No. PCT / US2018 / 054688, filed on October 5, 2018, entitled "Methods for Making Yerba Mate Extract Compositions," and U.S. Provisional Application No. 62 / 676,722, filed on May 25, 2018, entitled "Methods for Making Yerba Mate Extract Compositions." For example, the sensory modifier may be isolated from a plant source that includes one or more of monocaffeoylquinic acid, dicaffeoylquinic acid, and salts thereof. For example, yerba mate biomass and stevia biomass can be used to prepare the sensory modifier. In one exemplary process, the sensory modifier is prepared from commercially obtained ground yerba mate biomass. Briefly, yerba mate biomass is suspended in 50% (v / v) ethanol / water and shaken for at least 1 hour, and the resulting mixture is filtered to obtain an initial extract. The initial extract is diluted with water to 35% (v / v) ethanol and refiltered. The refiltered permeate is then applied to a column of AMBERLITE® FPA 53 resin equilibrated with 35% (v / v) ethanol / water, and the column permeate is discarded.The column is washed with 35% (v / v) ethanol / water and the column permeate is discarded. The column is then eluted with 10% (w / v) FCC grade sodium chloride in 50% (v / v) ethanol / water and the eluate is retained. Nitrogen gas is spurted onto the surface of the eluate at room temperature to remove the ethanol and reduce the eluate to 1 / 3 of its original volume. The reduced volume of the eluate is then filtered through a 0.2 μm polyethersulfone filter and then decolorized by passing through a 3 kDa molecular weight cutoff membrane. The decolorized permeate is retained and desalted by passing through a nanofiltration membrane. The desalted permeate is then freeze-dried to obtain the sensory modifier. This process is also suitable for obtaining sensory modifiers from Stevia biomass and can be adapted to obtain sensory modifiers from other plant sources, such as those mentioned above.
[0097] In some embodiments, the sensory modifier may be a blend of sensory modifiers isolated from two or more botanical sources.
[0098] In some embodiments, the composition having steviol glycosides and a sensory modifier does not contain a particular compound above a particular cutoff weight percent. For example, the composition may contain less than 0.3% (wt) of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, or malic acid, or less than 0.05% (wt) of pyruvate, pyruvic acid, fumarate, fumaric acid, tartrate, tartaric acid, sorbate, sorbic acid, acetate, or acetic acid, or less than about 0.05% (wt) of chlorophyll. composition
[0099] Steviol glycosides, together with one or more sensory modifiers, may be incorporated into any known foodstuff (referred to herein as a "sweetenable composition") or other composition intended for ingestion and / or contact by the oral cavity of a human or animal, such as pharmaceutical compositions, edible gel mixtures and compositions, dental and oral hygiene compositions, foods (e.g., confectioneries, seasonings, chewing gum, cereal compositions, baked foods, bakeable foods, culinary adjuvants, dairy products, and tabletop sweetener compositions), beverages, and other beverage products (e.g., beverage mixtures, beverage concentrates, etc.). Examples of such compositions and aspects thereof are described in PCT Publication Nos. WO 2019 / 071220 and WO 2019 / 071182, and U.S. Patent Application Publication Nos. 2019 / 0223481 and 2019 / 0223483, each of which is incorporated herein by reference in its entirety.
[0100] A pharmaceutical composition includes a pharma- ceutical active substance and a pharma- ceutical acceptable carrier or excipient material. A dental composition includes an active dental substance that improves the aesthetics or health of at least a portion of the oral cavity, and a base material that is an inert substance used as a vehicle.
[0101] The steviol glycoside composition may be a tabletop sweetener composition. The tabletop sweetener composition may further include various other ingredients, such as one or more fillers, additives, anti-caking agents, functional ingredients, or any combination thereof. 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. Further, according to yet another embodiment, granulated sugar (sucrose) or other caloric sweeteners such as crystalline fructose, other carbohydrates, or sugar alcohols can be used as bulking agents to provide good content uniformity without adding significant calories. Tabletop sweetener compositions can also be embodied in liquid form, where a sweetener composition comprising a steviol glycoside component and one or more sensory modifiers is combined with a liquid carrier. Non-limiting examples of suitable carrier agents for liquid tabletop functional sweeteners include water, alcohol, polyols, glycerin-based or citric acid-based sweeteners dissolved in water, and mixtures thereof. Further aspects of tabletop sweeteners are described in PCT Publication Nos. WO 2019 / 071220 and WO 2019 / 071182, and U.S. Patent Application Publication Nos. 2019 / 0223481 and 2019 / 0223483, each of which is incorporated herein by reference in its entirety.
[0102] The steviol glycoside composition may be a beverage. As used herein, "beverage product" includes, but is not limited to, instant beverages, beverage concentrates, beverage syrups, frozen beverages, or powdered beverages. Suitable instant beverages include carbonated and non-carbonated beverages. Carbonated beverages include, but are not limited to, highly carbonated soft drinks, cola, lemon-lime flavored sparkling soft drinks, orange flavored sparkling soft drinks, grape flavored sparkling soft drinks, strawberry flavored sparkling soft drinks, pineapple flavored sparkling soft drinks, ginger ale, soft drinks, and root beer. Non-carbonated beverages include, but are not limited to, fruit juices, fruit-flavored juices, juice drinks, nectars, vegetable juices, vegetable-flavored juices, sports drinks, energy drinks, enhanced water drinks, vitamin-enhanced water drinks, mostly water drinks (e.g., water with added natural or synthetic flavorings), coconut water, tea-type beverages (e.g., black tea, green tea, black tea, oolong tea), coffee, cocoa beverages, beverages containing dairy ingredients (e.g., dairy beverages, dairy coffee, cafe latte, milk tea, fruit milk beverages), beverages containing grain extracts, smoothies, and combinations thereof. Examples of frozen beverages include, but are not limited to, iced drinks, frozen cocktails, daiquiris, pina coladas, margaritas, milkshakes, frozen coffee, frozen lemonade, granitas, and slushies. Beverage concentrates and beverage syrups can be prepared with an initial volume of liquid ingredients (e.g., water) and the desired beverage ingredients. A final strength beverage is then prepared by adding a further volume of water. The powdered beverage is prepared by dry mixing all the beverage ingredients in the absence of any liquid ingredients. A final strength beverage is then prepared by adding a final volume of water.
[0103] In one embodiment, the beverage contains a sweetener composition comprising a steviol glycoside component and a sensory modifier. Any sweetener composition comprising a steviol glycoside and a sensory modifier detailed herein may be used in the beverage. In another embodiment, a method of preparing a beverage comprises combining a liquid matrix, a steviol glycoside component, and a sensory modifier. The method may further comprise the addition of one or more sweeteners, additives, and / or functional ingredients. In yet another embodiment, a method of preparing a beverage comprises combining a liquid matrix and a sweetener composition comprising a steviol glycoside component and a sensory modifier.
[0104] In another embodiment, the beverage contains a sweetener composition containing steviol glycosides, and the steviol glycosides are present in the beverage in an amount ranging from about 1 ppm to about 10,000 ppm, such as, for example, about 25 ppm to about 800 ppm. In another embodiment, the steviol glycosides are present in the beverage in an amount ranging from about 100 ppm to about 600 ppm. In yet another aspect, the steviol glycosides are present in the beverage in an amount ranging from about 100 to about 200 ppm, about 100 ppm to about 300 ppm, about 100 ppm to about 400 ppm, or about 100 ppm to about 500 ppm. In yet another embodiment, the steviol glycosides are present in the beverage in an amount ranging from about 300 to about 700 ppm, such as, for example, about 400 ppm to about 600 ppm. In a particular embodiment, steviol glycosides are present in the beverage in an amount of about 500 ppm.
[0105] In one embodiment, the composition is a beverage, and the total glycoside content in the beverage is about 50-1500 ppm, or 100-1200 ppm, 200-1000 ppm, 300-900 ppm, 350-800 ppm, 400-600 ppm, or 450-550 ppm. In one embodiment, a steviol glycoside other than Reb D, Reb M, Reb B, and / or Reb A, or other than Reb D and / or Reb B, and optionally other than Reb G, Reb O, Reb N, and / or Reb E, e.g., a sensory modifier, is present in the beverage at about at least 1 ppm to about 600 ppm, e.g., about 50 ppm to about 500 ppm (including at least 1, 5, 10, 20, 30, 40, 50, 125, 150, 150, 175 ppm, or 200 ppm). In one embodiment, steviol glycosides other than Reb D, Reb M, Reb B, and / or Reb A, or other than Reb D and / or Reb B, and optionally Reb G, Reb O, Reb N, and / or Reb E, are present in the beverage at about 1-600 ppm, 10-400, 50-200, 75-150, 5-200, 10-100, 20-90, 30-80 ppm, etc. In one embodiment, steviol glycosides other than Reb D, Reb M, Reb B, and / or Reb A, are present at about 1-600 ppm, 10-400, 50-200, 75-150, 5-200, 10-100, 20-90, 30-80 ppm, etc. Additional Components
[0106] In some embodiments, the composition having a steviol glycoside component and a sensory modifier also contains one or more additional non-steviol glycoside sweetener compounds. The non-steviol glycoside sweetener compounds can be any type of sweetener, such as a sweetener obtained from a plant or plant product, or a physically or chemically modified sweetener obtained from a plant, or a synthetic sweetener. Exemplary non-steviol glycoside sweeteners include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrins (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altoose, and the like. sugar, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine, fucose, fuculose, glucuronic acid, gluconic acid, gluconolactone, abequase, galactosamine, xylooligosaccharides (xylotri ose, xylobiose, and other), gentiooligosaccharides (gentiobiose, gentiotriose, and gentiotetraose, and other), galactooligosaccharides, sorbose, ketotriose (dehydroxyacetone), aldotriose (glyceraldehyde), nigerooligosaccharides, fructooligosaccharides (kestose, nystose, and other), maltotetraose, maltotriose, tetrasaccharides, mannanoligosaccharides, maltooligosaccharides (maltotriose, Examples of suitable sugars include maltotetraose, maltopentaose, maltohexaose, and maltoheptaose), dextrins, lactulose, melibiose, raffinose, rhamnose, ribose, sucralose, isomerized liquid sugars such as high fructose corn / starch syrup (HFCS / HFSS) (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars, soybean oligosaccharides, glucose syrup, and combinations thereof.Where available, either the D- or L-form can be used. Non-steviol glycoside sweeteners and embodiments thereof are also described in PCT Publication Nos. WO 2019 / 071220 and WO 2019 / 071182, and U.S. Patent Application Publication Nos. 2019 / 0223481 and 2019 / 0223483, each of which is incorporated herein by reference in its entirety.
[0107] In various embodiments, the steviol glycoside composition may further optionally include a liquid carrier, a binder matrix, additional additives, and / or the like. In some aspects, the sweetener composition contains additives, including, but not limited to, carbohydrates, polyols, amino acids and their corresponding salts, polyamino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic salts, bitter compounds, flavorings and fragrances, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, bulking agents, gums, antioxidants, colorants, flavonoids, alcohols, polymers, and combinations thereof. In some aspects, the additives act to improve the temporal and flavor profile to provide the sweetener composition with a desirable taste, such as a taste similar to sucrose. Examples of such components and embodiments thereof are described in PCT Publication Nos. WO 2019 / 071220 and WO 2019 / 071182, and U.S. Patent Application Publication Nos. 2019 / 0223481 and 2019 / 0223483, each of which is incorporated by reference in its entirety.
[0108] The sweetener composition comprising the steviol glycoside component and the sensory modifier may also contain one or more functional ingredients that provide a real or perceived health benefit to the composition. Functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydrating agents, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, long chain primary aliphatic saturated alcohols, phytosterols, and combinations thereof. Examples of functional ingredients and aspects thereof are described in PCT Publication Nos. WO 2019 / 071220 and WO 2019 / 071182, and U.S. Patent Application Publication Nos. 2019 / 0223481 and 2019 / 0223483, each of which is incorporated herein by reference in its entirety.
[0109] The present invention may be better understood by reference to the following examples, which are provided by way of illustration and are not intended to be limiting of the invention to the examples set forth herein. EXAMPLES
[0110] Materials and Methods Various steviol glycoside components were tested.
[0111] The sensory modifier tested was a mixture of mono- and dicaffeoylquinic acids prepared from yerba mate and subsequently adjusted to have different salt fractions. Table 2 lists the contents and sources of the various components.
[0112] Solutions were prepared containing either steviol glycoside components alone or steviol glycoside components and sensory modifiers in a 2:1 molar ratio (which also corresponds to a 2:1 weight ratio) for use as control samples. The solutions were prepared by dissolving the steviol glycoside components and sensory modifiers in reverse osmosis water at the indicated concentrations and / or ratios. [Table 2]
[0113] An assay was conducted to characterize the sensory properties of steviol glycoside compositions with various salt fractions of sensory modifiers. The sensory properties of the solutions were tested by a panel of at least four individuals with experience tasting steviol glycoside compositions. An experienced panelist evaluated each sweetness attribute using the round table method. To test each solution, an experienced panelist dispensed approximately 2 mL of each solution into their mouth by a full volume pipette, dispersed the solution by moving their tongue, and recorded the value of the particular sweetness attribute being tested. Between tasting solutions, the panelists were allowed to wash their palate with water. For each sweetness attribute, the panelists agreed on a descriptive scale with the relative intensity assigned to each sweetness attribute, against which the value of each sweetness attribute was then recorded. Table 3 lists the scoring criteria for the various sensory attributes. [Table 3] Example 1 - Aqueous Test Samples
[0114] A mixture of mono- and dicaffeoylquinic acids was obtained from yerba mate to obtain the sensory modifier in acid form. Apart from the steviol glycoside component, the mixture of mono- and dicaffeoylquinic acids was adjusted with sodium or potassium hydroxide to obtain the sodium or potassium salt (each corresponding to 100% salt form). The obtained samples were freeze-dried to provide the sensory modifier (SM) in powder form for ready use. A series of samples was prepared from the sensory modifier. For each sample, the final concentration of the sensory modifier was 470-500 ppm (w / w) including the salt mass contribution. The preparation of each sample including the amount of each component is shown in Tables 4-6. Steviol glycoside component examples A and B were used alone as control samples and also as starting points for the sensory modifier samples. [Table 4] [Table 5] [Table 6]
[0115] For each sample, the flavor profile was compared to steviol glycoside solution alone as well as samples with different salt compositions.
[0116] Both the potassium and sodium salt forms of the sensory modifier with Reb M showed improvement over Reb M alone. Table 7 shows the sensory properties reported for each test composition. Table 8 shows the SEV values reported for each test composition and provides taster comments. As shown in Table 7, the potassium and sodium salt forms provided a substantially rounder sweetness profile for Reb M. The potassium and sodium salt forms provided substantially reduced sweetness linger and greatly reduced bitterness for both Reb M and Reb N. As shown in Table 8, the potassium and sodium salt forms provided a slightly reduced SEV. The potassium salt imparts a slightly higher astringency than the sodium salt form of the sensory modifier overall. There is a subtle cherry fruit flavor introduced with the potassium salt. Thus, it is shown that the sodium and potassium salt forms of the sensory modifier provide significant modulation of the sensory profile of the steviol glycoside components. Considering the number of different sensory attributes that can each be varied independently, it is surprising that the salt form of the sensory modifier provides desirable results in each test and overall, without a significant disadvantage in any one area. Furthermore, the reduction in bitterness and reduction in sweetness linger show highly significant improvements over samples without the sensory modifier. [Table 7] * =Typical Reb M and Reb N characteristics are astringent, metallic, powdery, numb, vaporous. ND = Not Detected [Table 8] Example 2 - Simulated Beverage Test
[0117] Simulated beverages were prepared using steviol glycoside components, sensory modifiers, and a simulated beverage system.
[0118] To prepare the simulated beverage system, citric acid (anhydrous, final concentration 0.1 wt%) and potassium citrate (monohydrate, final concentration 0.026 wt%) were dissolved in deionized water. Steviol Glycoside Component Example C was added and dissolved to this buffer system to obtain a final concentration of 350 ppm (wt / wt). Steviol Glycoside Component Example C contains rebaudiosides M and D.
[0119] A mixture of mono-caffeoylquinic acid and dicaffeoylquinic acid in acid form (i.e., 100 mole % acid fraction) was treated with sodium hydroxide to introduce salt fractions and adjust the salt mole % fraction to various mole fractions as shown in Table 9. Thus, the resulting caffeoylquinic acid mixture contained mono-caffeoylquinic acid in acid form, dicaffeoylquinic acid in acid form, mono-caffeoylquinic acid in salt form, and dicaffeoylquinic acid in salt form. The resulting mixture was freeze-dried to provide several ready-to-use sensory modifiers in powder form. These sensory modifiers are listed in Table 9 according to the mole % of sodium, which in this example corresponds to the salt fraction. Due to the similar molecular weight between the acid form and the salt form, the mole % of Na can be interpreted as approximately equal to the weight %.
[0120] A series of test beverages were then prepared by combining the beverage system and sensory modifiers described above. For each simulated beverage sample obtained, the final concentration of sensory modifier was 250 ppm (w / w), which was adjusted based on the total mass of sensory modifier, excluding the contribution of salt mass. For each sample, the flavor profile was compared with steviol glycoside solution alone, as well as with samples with different salt fractions. After tasting each sample, the panel voted based on personal preference on which salt fraction provided a better sweetness profile.
[0121] As shown in the table, all samples within the 50 mol% to 80 mol% salt fraction range were preferred, with the most optimal composition being 70 mol%. At higher salt levels, from 80 mol% salt to 100 mol% salt, the product was not effective in reducing the sweetness linger of Reb M and had an unpleasant, musty, earthy flavor. At 60 mol% to 80 mol% salt, the product was very effective in reducing the sweetness linger and bitterness of Reb M, and the unpleasant musty flavor became subtle. At 70 mol% salt, the musty flavor was very mild, the sweetness was present initially, with a clean, rounded taste profile, and a very reduced sweetness linger. At less than 60 mol% salt, the astringency became more and more pronounced, along with a tongue-coating and tingling sensation.
[0122] The data shows that a certain range of salt fraction (mol % of salt) of the sensory modifier results in significant reduction of bitterness and sweetness linger. This result is particularly surprising because it cannot be predicted by looking at the acid form alone or the salt form alone. For example, the acid form alone (0 mol % salt) resulted in undesirable sourness and astringency. The salt form alone (100 mol % salt) resulted in similar results to those without any sensory modifier. Neither the acid form alone nor the salt form alone resulted in any significant reduction in bitterness or sweetness linger. Therefore, it is surprising that the combination of acid and salt results in the beneficial effect of reducing bitterness and reducing sweetness linger. It is also surprising that this benefit is not achieved in all cases where both salt and acid are present, for example, a mixture of less than 50 mol % salt does not provide the same benefit, and a mixture of more than 90 mol % begins to provide only a slight reduction in sweetness linger. [Table 9] Exemplary embodiments
[0123] This disclosure provides the following exemplary embodiments, the numbering of which should not be construed as designating a level of importance.
[0124] Embodiment 1 relates to a steviol glycoside composition, the composition comprising: Steviol glycoside components, a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or both; The sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, at least 50% by weight of the sensory modifier being in the salt form.
[0125] Embodiment 2 relates to a steviol glycoside composition having reduced sweetness, the composition comprising: Steviol glycoside components, a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or both; The sensory modifier comprises a salt fraction and an acid fraction, the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid; The acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid; The salt fraction constitutes at least 50% by weight of the total sensory modifier.
[0126] Embodiment 3 relates to a steviol glycoside composition according to embodiment 1 or 2, wherein the sensory modifier comprises one or more of chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), cryptochlorogenic acid (4-O-caffeoylquinic acid), 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid, and salts thereof.
[0127] Embodiment 4 relates to a steviol glycoside composition according to any one of embodiments 1 to 3, wherein the sensory modifier is a mixture of one or more monocaffeoylquinic acids and one or more dicaffeoylquinic acids and salts thereof.
[0128] Embodiment 5 relates to a steviol glycoside composition according to any one of embodiments 2 to 4, wherein the monocaffeoylquinic acid is one or more of chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), or cryptochlorogenic acid (4-O-caffeoylquinic acid).
[0129] Embodiment 6 relates to a steviol glycoside composition according to any one of embodiments 2 to 5, wherein the monocaffeoylquinate is one or more of a salt of 3-O-caffeoylquinic acid, a salt of 4-O-caffeoylquinic acid, or a salt of 5-O-caffeoylquinic acid.
[0130] Embodiment 7 relates to a steviol glycoside composition according to any one of embodiments 2 to 5, wherein the dicaffeoylquinic acid salt is one or more of a salt of 1,3-dicaffeoylquinic acid, a salt of 1,4-dicaffeoylquinic acid, a salt of 1,5-dicaffeoylquinic acid, a salt of 3,4-dicaffeoylquinic acid, a salt of 3,5-dicaffeoylquinic acid, or a salt of 4,5-dicaffeoylquinic acid.
[0131] Embodiment 8 relates to a steviol glycoside composition according to any one of embodiments 2 to 5, wherein the dicaffeoylquinic acid is one or more of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid.
[0132] Embodiment 9 relates to a steviol glycoside composition according to any one of embodiments 1 to 8, wherein 10% by weight or more of the sensory modifier is dicaffeoylquinic acid and its salts.
[0133] Embodiment 10 relates to a steviol glycoside composition according to any one of embodiments 1 to 9, wherein 25% by weight or more of the sensory modifier is dicaffeoylquinic acid and its salts.
[0134] Embodiment 11 relates to a steviol glycoside composition according to any one of embodiments 1 to 10, wherein 50% by weight or more of the sensory modifier is dicaffeoylquinic acid and its salts.
[0135] Embodiment 12 relates to a steviol glycoside composition according to any one of embodiments 1 to 11, wherein the sensory modifier is a mixture having a ratio of monocaffeoylquinic acid and salts of monocaffeoylquinic acid:dicaffeoylquinic acid and salts of dicaffeoylquinic acid of 3:1 to 1:3.
[0136] Embodiment 13 relates to a steviol glycoside composition according to any one of embodiments 1 to 12, wherein the sensory modifier has a ratio of about 1:1 of monocaffeoylquinic acid and salts of monocaffeoylquinic acid:dicaffeoylquinic acid and salts of dicaffeoylquinic acid.
[0137] Embodiment 14 relates to a steviol glycoside composition according to any one of embodiments 1 to 13, wherein the sensory modifier is a mixture of 40% to 60% by weight of dicaffeoylquinic acid and its salts.
[0138] Embodiment 15 relates to a steviol glycoside composition according to any one of embodiments 1 to 14, wherein 90% by weight or less of the sensory modifier is in salt form.
[0139] Embodiment 16 relates to a steviol glycoside composition according to any one of embodiments 1 to 15, wherein 80% by weight or less of the sensory modifier is in salt form.
[0140] Embodiment 17 relates to a steviol glycoside composition according to any one of embodiments 1 to 16, wherein 50% to 90% by weight of the sensory modifier is in salt form.
[0141] Embodiment 18 relates to a steviol glycoside composition according to any one of embodiments 1 to 17, wherein 60% to 80% by weight of the sensory modifier is in salt form.
[0142] Embodiment 19 relates to a steviol glycoside composition according to any one of embodiments 1 to 18, wherein 65% to 75% by weight of the sensory modifier is in salt form.
[0143] Embodiment 20 relates to a steviol glycoside composition according to any one of embodiments 1 to 19, wherein at least 10% by weight of the sensory modifier is in acid form.
[0144] Embodiment 21 relates to a steviol glycoside composition according to any one of embodiments 1 to 20, wherein at least 20% by weight of the sensory modifier is in acid form.
[0145] Embodiment 22 relates to a steviol glycoside composition according to any one of embodiments 1 to 21, wherein 20% to 40% by weight of the sensory modifier is in acid form.
[0146] Embodiment 23 relates to a steviol glycoside composition according to any one of embodiments 1 to 22, wherein 25% to 35% by weight of the sensory modifier is in acid form.
[0147] Embodiment 24 relates to a steviol glycoside composition according to any one of embodiments 2 to 23, wherein the salt fraction constitutes at least 60% by weight of the total sensory modifier.
[0148] Embodiment 25 relates to a steviol glycoside composition according to any one of embodiments 2 to 23, wherein the salt fraction constitutes less than 90% by weight of the total sensory modifier.
[0149] Embodiment 26 relates to a steviol glycoside composition according to any one of embodiments 2 to 23, wherein the salt fraction constitutes less than 80% by weight of the total sensory modifier.
[0150] Embodiment 27 relates to a steviol glycoside composition according to any one of embodiments 2 to 23, wherein the salt fraction constitutes 60-80% by weight of the total sensory modifier.
[0151] Embodiment 28 relates to a steviol glycoside composition according to any one of embodiments 2 to 23, wherein the salt fraction constitutes 65-75% by weight of the total sensory modifier.
[0152] Embodiment 29 relates to a steviol glycoside composition according to any one of embodiments 2 to 28, wherein the acid fraction comprises at least 10% by weight of the total sensory modifier.
[0153] Embodiment 30 relates to a steviol glycoside composition according to any one of embodiments 2 to 29, wherein the acid fraction comprises at least 20% by weight of the total sensory modifier.
[0154] Embodiment 31 relates to a steviol glycoside composition according to any one of embodiments 2 to 30, wherein the acid fraction constitutes 20-40% by weight of the total sensory modifier.
[0155] Embodiment 32 relates to a steviol glycoside composition according to any one of embodiments 2 to 31, wherein the acid fraction constitutes 25 to 35% by weight of the total sensory modifier.
[0156] Embodiment 33 relates to a steviol glycoside composition according to any one of embodiments 1 to 32, wherein the sensory modifier comprises one or more salts selected from sodium, potassium, magnesium, and calcium.
[0157] Embodiment 34 relates to a steviol glycoside composition according to any one of embodiments 1 to 33, wherein the sensory modifier comprises one or more sodium salts.
[0158] Embodiment 35 relates to a steviol glycoside composition according to any one of embodiments 1 to 34, wherein the sensory modifier comprises one or more potassium salts.
[0159] Embodiment 36 relates to a steviol glycoside composition according to any one of embodiments 1 to 35, wherein the sensory modifier comprises a mixture of one or more potassium salts and one or more sodium salts.
[0160] Embodiment 37 relates to a steviol glycoside composition according to any one of embodiments 1 to 36, wherein the composition has a pH higher than the pH at the half-equivalence point of the sensory modifier.
[0161] Embodiment 38 relates to a steviol glycoside composition according to any one of embodiments 1 to 37, wherein the composition has a pH lower than the pH at the equivalence point of the sensory modifier.
[0162] Embodiment 39 relates to a steviol glycoside composition according to any one of embodiments 1 to 38, wherein the composition has a pH of less than 4.0.
[0163] Embodiment 40 relates to a steviol glycoside composition according to any one of embodiments 1 to 39, wherein the composition has a pH of 1.7 to 4.0.
[0164] Embodiment 41 relates to a steviol glycoside composition according to any one of embodiments 1 to 40, wherein the composition has a pH greater than 2.0.
[0165] Embodiment 42 relates to a steviol glycoside composition according to any one of embodiments 1 to 41, wherein the composition has a pH greater than 2.5.
[0166] Embodiment 43 relates to a steviol glycoside composition according to any one of embodiments 1 to 42, wherein at least a portion of the sensory modifier is prepared from a plant source.
[0167] Embodiment 44 relates to a steviol glycoside composition according to any one of embodiments 1 to 43, wherein the plant source is yerba mate, rosemary, chicory, stevia, artichoke, coffee, or a mixture thereof.
[0168] Embodiment 45 relates to a steviol glycoside composition according to any one of embodiments 1 to 44, wherein at least a portion of the sensory modifier is prepared from yerba mate.
[0169] Embodiment 46 relates to a steviol glycoside composition according to any one of embodiments 1 to 45, wherein at least a portion of the sensory modifier is prepared from stevia.
[0170] Embodiment 47 relates to a steviol glycoside composition according to any one of embodiments 1 to 46, wherein the steviol glycoside component comprises one or more of rebaudioside D, rebaudioside M, rebaudioside O, rebaudioside N, rebaudioside A, or a combination thereof.
[0171] Embodiment 48 relates to a steviol glycoside composition according to any one of embodiments 1 to 47, wherein the steviol glycoside component comprises rebaudioside D, rebaudioside M, or a combination thereof.
[0172] Embodiment 49 relates to a steviol glycoside composition according to any one of embodiments 1 to 48, wherein at least 80% by weight of the steviol glycoside component is rebaudioside M, based on the total weight of steviol glycosides in the steviol glycoside composition.
[0173] Embodiment 50 relates to a steviol glycoside composition according to any one of embodiments 1 to 49, wherein at least 90% by weight of the steviol glycoside component is rebaudioside M, based on the total weight of steviol glycosides in the steviol glycoside composition.
[0174] Embodiment 51 relates to a steviol glycoside composition according to any one of embodiments 1 to 50, wherein the composition comprises from 100 ppm to 1600 ppm of steviol glycosides.
[0175] Embodiment 52 relates to a steviol glycoside composition according to any one of embodiments 1 to 51, wherein the composition comprises at least 200 ppm of a steviol glycoside component.
[0176] Embodiment 53 relates to a steviol glycoside composition according to any one of embodiments 1 to 52, wherein the composition comprises from 200 ppm to 1000 ppm of the steviol glycoside component.
[0177] Embodiment 54 relates to a steviol glycoside composition according to any one of embodiments 1 to 53, wherein the composition comprises at least 300 ppm of the steviol glycoside component.
[0178] Embodiment 55 relates to a steviol glycoside composition according to any one of embodiments 1 to 54, wherein the composition comprises 400 ppm to 800 ppm of the steviol glycoside component.
[0179] Embodiment 56 relates to a steviol glycoside composition according to any one of embodiments 1 to 55, wherein the composition comprises at least 300 ppm of the steviol glycoside component.
[0180] Embodiment 57 relates to a steviol glycoside composition according to any one of embodiments 1 to 56, wherein the composition comprises from 100 ppm to 1600 ppm of rebaudioside M.
[0181] Embodiment 58 relates to a steviol glycoside composition according to any one of embodiments 1 to 57, wherein the composition comprises at least 200 ppm of rebaudioside M.
[0182] Embodiment 59 relates to a steviol glycoside composition according to any one of embodiments 1 to 58, wherein the composition comprises from 200 ppm to 1000 ppm of rebaudioside M.
[0183] Embodiment 60 relates to a steviol glycoside composition according to any one of embodiments 1 to 59, wherein the composition comprises at least 300 ppm of rebaudioside M.
[0184] Embodiment 61 relates to a steviol glycoside composition according to any one of embodiments 1 to 60, wherein the composition comprises from 400 ppm to 800 ppm of rebaudioside M.
[0185] Embodiment 62 relates to a steviol glycoside composition according to any one of embodiments 1 to 61, wherein the composition comprises at least 500 ppm of rebaudioside M.
[0186] Embodiment 63 relates to a steviol glycoside composition according to any one of embodiments 1 to 62, wherein the composition comprises from 100 ppm to 1600 ppm of a sensory modifier.
[0187] Embodiment 64 relates to a steviol glycoside composition according to any one of embodiments 1 to 63, wherein the composition comprises at least 200 ppm of a sensory modifier.
[0188] Embodiment 65 relates to a steviol glycoside composition according to any one of embodiments 1 to 64, wherein the composition comprises from 200 ppm to 1000 ppm of a sensory modifier.
[0189] Embodiment 66 relates to a steviol glycoside composition according to any one of embodiments 1 to 65, wherein the composition comprises at least 300 ppm of a sensory modifier.
[0190] Embodiment 67 relates to a steviol glycoside composition according to any one of embodiments 1 to 66, wherein the composition comprises from 400 ppm to 800 ppm of a sensory modifier.
[0191] Embodiment 68 relates to a steviol glycoside composition according to any one of embodiments 1 to 67, wherein the composition comprises at least 500 ppm of a sensory modifier.
[0192] Embodiment 69 relates to a steviol glycoside composition according to any one of embodiments 1 to 68, wherein the composition comprises from 50 ppm to 1400 ppm of a salt of caffeoylquinic acid.
[0193] Embodiment 70 relates to a steviol glycoside composition according to any one of embodiments 1 to 69, wherein the composition comprises at least 100 ppm of a salt of caffeoylquinic acid.
[0194] Embodiment 71 relates to a steviol glycoside composition according to any one of embodiments 1 to 70, wherein the composition comprises from 100 ppm to 900 ppm of a salt of caffeoylquinic acid.
[0195] Embodiment 72 relates to a steviol glycoside composition according to any one of embodiments 1 to 71, wherein the composition comprises at least 150 ppm of a salt of caffeoylquinic acid.
[0196] Embodiment 73 relates to a steviol glycoside composition according to any one of embodiments 1 to 72, wherein the composition comprises from 200 ppm to 720 ppm of a salt of caffeoylquinic acid.
[0197] Embodiment 74 relates to a steviol glycoside composition according to any one of embodiments 1 to 73, wherein the composition comprises at least 250 ppm of a salt of caffeoylquinic acid.
[0198] Embodiment 75 relates to a steviol glycoside composition according to any one of embodiments 1 to 74, wherein the composition comprises a weight ratio of steviol glycoside component to sensory modifier of from 1:0.3 to 1:3.
[0199] Embodiment 76 relates to a steviol glycoside composition according to any one of embodiments 1 to 75, wherein the composition comprises a weight ratio of steviol glycoside component to sensory modifier of from 1:0.3 to 1:1.
[0200] Embodiment 77 relates to a steviol glycoside composition according to any one of embodiments 1 to 76, wherein the composition comprises a weight ratio of the steviol glycoside component to the sensory modifier of about 2:1.
[0201] Embodiment 78 relates to a steviol glycoside composition according to any one of embodiments 1 to 77, wherein the amount effective to reduce sweetness linger is determined by at least four panelists trained in tasting steviol glycoside compositions using a round table method using a scale of 0 to 6, where a score of 0 indicates no sweetness linger and a score of 6 indicates extreme sweetness linger, and the sweetness linger score is reduced by at least 1 unit compared to a control sample not containing a sensory modifier.
[0202] Embodiment 79 relates to a steviol glycoside composition according to any one of embodiments 1 to 78, wherein an effective amount reduces sweetness linger by at least 2 units compared to a control sample not containing a sensory modifier.
[0203] Embodiment 80 relates to a steviol glycoside composition according to any one of embodiments 1 to 79, wherein an effective amount reduces sweetness linger by at least 3 units compared to a control sample not containing a sensory modifier.
[0204] Embodiment 81 relates to a steviol glycoside composition according to any one of embodiments 1 to 80, wherein the effective amount reduces sweetness linger to less than 3 units compared to a control sample not containing a sensory modifier.
[0205] Embodiment 82 relates to a steviol glycoside composition according to any one of embodiments 1 to 81, wherein the steviol glycoside composition has reduced sweetness linger compared to a steviol glycoside that does not contain a sensory modifier.
[0206] Embodiment 83 relates to a steviol glycoside composition according to any one of embodiments 1 to 82, wherein the bitterness-reducing effective amount is determined by at least four panelists trained in tasting steviol glycoside compositions using a round table method using a scale of 0 to 6, where a score of 0 indicates no sweetness linger and a score of 6 indicates extreme sweetness linger, and the sweetness linger score is reduced by at least 1 unit compared to a control sample not containing a sensory modifier.
[0207] Embodiment 84 relates to a steviol glycoside composition according to any one of embodiments 1 to 83, wherein the effective amount reduces bitterness by at least 2 units compared to a control sample not containing a sensory modifier.
[0208] Embodiment 85 relates to a steviol glycoside composition according to any one of embodiments 1 to 83, wherein the effective amount reduces bitterness by at least 3 units compared to a control sample not containing a sensory modifier.
[0209] Embodiment 86 relates to a steviol glycoside composition according to any one of embodiments 1 to 83, wherein the effective amount reduces the bitter taste to less than 2 units compared to a control sample not containing a sensory modifier.
[0210] Embodiment 87 relates to a steviol glycoside composition according to any one of embodiments 1 to 83, wherein the effective amount reduces the bitter taste to less than 1 unit compared to a control sample not containing a sensory modifier.
[0211] Embodiment 88 relates to a steviol glycoside composition according to any one of embodiments 1 to 87, wherein the steviol glycoside composition has a reduced bitterness compared to a control sample not containing a sensory modifier.
[0212] Embodiment 89 relates to a steviol glycoside composition according to any one of embodiments 1 to 88, wherein the composition is an aqueous solution.
[0213] Embodiment 90 relates to a steviol glycoside composition according to any one of embodiments 1 to 89, wherein the composition is in a solid form.
[0214] Embodiment 91 relates to a steviol glycoside composition according to any one of embodiments 1 to 90, wherein the composition is a lyophilized powder.
[0215] Embodiment 92 relates to a steviol glycoside composition according to any one of embodiments 1 to 91, wherein the steviol glycoside component is at a concentration of 200 to 1000 ppm and the sensory modifier is at a concentration of 200 to 1000 ppm.
[0216] Embodiment 93 relates to a steviol glycoside composition according to any one of embodiments 1 to 92, wherein the steviol glycoside component is at a concentration of 400 to 800 ppm and the sensory modifier is at a concentration of 400 to 800 ppm.
[0217] Embodiment 94 relates to a steviol glycoside composition according to any one of embodiments 1 to 93, wherein the composition has a reduced sweetness linger compared to the same composition without a sensory modifier.
[0218] Embodiment 95 relates to a steviol glycoside composition according to any one of embodiments 1 to 94, wherein the composition has a reduced bitter taste compared to the same composition without the sensory modifier.
[0219] Embodiment 96 relates to a steviol glycoside composition according to any one of embodiments 1 to 95, wherein the sensory modifier is in an amount effective to reduce sweetness linger.
[0220] Embodiment 97 relates to a steviol glycoside composition according to any one of embodiments 1 to 96, wherein the sensory modifier is in an amount effective to reduce bitterness.
[0221] Embodiment 98 relates to a steviol glycoside composition according to any one of embodiments 1 to 97, wherein the sweetness linger, the bitterness, or both are associated with rebaudioside M, rebaudioside N, rebaudioside O, rebaudioside D, or a combination thereof.
[0222] Embodiment 99 relates to a beverage comprising the steviol glycoside composition according to any one of embodiments 1 to 98.
[0223] Embodiment 100 relates to a pharmaceutical composition, a dental composition, a chewing gum, or a solid food comprising the steviol glycoside composition according to any one of embodiments 1 to 98.
[0224] Embodiment 101 relates to a method for reducing undesirable sensory properties of an aqueous solution of steviol glycosides, the method comprising dissolving a composition according to any one of embodiments 1 to 98 in an aqueous solution of steviol glycosides.
[0225] Embodiment 102 relates to the method of embodiment 99, wherein the undesirable sensory characteristic is bitterness, sweetness linger, sharp taste, harshness, astringency, or rebaudioside M characteristics.
[0226] Embodiment 103 relates to the method of embodiment 101, wherein the undesirable sensory property is bitterness.
[0227] Embodiment 104 relates to the method of embodiment 101, wherein the undesirable sensory characteristic is sweetness linger.
[0228] Embodiment 105 relates to the method of embodiment 101, wherein the undesirable sensory characteristic is a rebaudioside M type characteristic selected from one or more of metallic, powdery, numb, and vapor-like characteristics.
[0229]
[00136] Embodiment 106 relates to a method for reducing sweetness linger from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component; The sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, at least 50% by weight of the sensory modifier being in the salt form.
[0230]
[0081] Embodiment 107 relates to a method for reducing sweetness linger from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component; The sensory modifier comprises a salt fraction and an acid fraction, the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid; The acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid; The salt fraction constitutes at least 50% by weight of the total sensory modifier.
[0231]
[00136] Embodiment 108 relates to a method for reducing bitterness from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component; The sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, at least 50% by weight of the sensory modifier being in the salt form.
[0232]
[00136] Embodiment 109 relates to a method for reducing bitterness from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component; The sensory modifier comprises a salt fraction and an acid fraction, the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid; The acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid; The salt fraction constitutes at least 50% by weight of the total sensory modifier.
[0233] Embodiment 110 relates to a method according to any one of embodiments 99 to 107, wherein the steviol glycoside component and the sensory modifier are added simultaneously.
[0234] Embodiment 111 is steviol glycoside components including at least one of rebaudioside D, rebaudioside M, and rebaudioside A, the total concentration of the steviol glycoside components being 200 ppm to 1000 ppm; A sensory modifier having a concentration of 200 ppm to 1000 ppm is contained in an aqueous solution of steviol glycoside having reduced sweetness linger. The sensory modifier comprises a salt fraction and an acid fraction, the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid; The acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid; the salt fraction comprises 50-80% by weight of the total sensory modifier, at least a portion of which is prepared from yerba mate or stevia; The aqueous steviol glycoside solutions have a reduced sweetness linger compared to aqueous steviol glycoside solutions having the same steviol glycoside components at the same concentrations without a sensory modifier.
[0235] Embodiment 112 is a steviol glycoside component including at least one of rebaudioside D, rebaudioside M, and rebaudioside A, the steviol glycoside component having a total concentration of 400 ppm to 800 ppm; and a sensory modifier having a concentration of 400 ppm to 800 ppm. The sensory modifier comprises a salt fraction and an acid fraction, the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid; The acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid; the salt fraction constitutes 50-80% by weight of the total sensory modifier and the acid fraction constitutes 20-50% by weight of the total sensory modifier; at least a portion of the sensory modifier is prepared from yerba mate or stevia; The aqueous steviol glycoside solutions have a reduced bitter taste compared to aqueous steviol glycoside solutions having the same steviol glycoside components at the same concentrations without the sensory modifier.
[0236] Embodiment 113 is about 200 to about 800 ppm of steviol glycoside constituents including rebaudioside D and rebaudioside M, wherein rebaudioside M is at least 80% by weight of the steviol glycoside constituents; and about 200 to about 400 ppm of a sensory modifier, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form.
[0237] Embodiment 114 relates to a steviol glycoside composition of claim 113, wherein the composition has a rounded taste profile, little sweetness linger, a sucrose-like mouthfeel, little astringency, and little bitterness.
[0238] Embodiment 115 relates to a steviol glycoside composition of claim 113, wherein the composition has a rounded taste profile, little sweetness linger, a sucrose-like mouthfeel, little astringency, and little bitterness. (Aspect 1) 1. A steviol glycoside composition, comprising: Steviol glycoside components, a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or both; 1. A steviol glycoside composition, comprising: a) a weight ratio of steviol glycoside component to sensory modifier of from 1:0.3 to 1:3; or b) the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight, preferably 50% to 90%, 50% to 80%, or 60% to 90% by weight of the sensory modifier is in salt form. (Aspect 2) 1. A steviol glycoside composition, comprising: Steviol glycoside components, a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or both; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; a) the weight ratio of steviol glycoside components to sensory modifier is from 1:0.3 to 1:3; or b) the salt fraction constitutes at least 50% by weight of the sensory modifier, preferably from 50% to 90% by weight, 50% to 80% by weight, or 60% to 90% by weight of the sensory modifier. (Aspect 3) 3. The steviol glycoside composition of claim 1 or 2, wherein the sensory modifier comprises one or more of 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid, and salts thereof. (Aspect 4) 2. The steviol glycoside composition of claim 1, wherein the sensory modifier is a mixture of one or more monocaffeoylquinic acids or salts thereof and one or more dicaffeoylquinic acids or salts thereof. (Aspect 5) 5. The steviol glycoside composition of claim 2 or 4, wherein the monocaffeoylquinic acid is one or more of 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, or 5-O-caffeoylquinic acid. (Aspect 6) 5. The steviol glycoside composition of claim 2 or 4, wherein the mono-caffeoylquinate is one or more of a salt of 3-O-caffeoylquinic acid, a salt of 4-O-caffeoylquinic acid, or a salt of 5-O-caffeoylquinic acid. (Aspect 7) 5. The steviol glycoside composition of claim 2 or 4, wherein the dicaffeoylquinic acid is one or more of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid. (Aspect 8) 5. The steviol glycoside composition of claim 2 or 4, wherein the dicaffeoylquinic acid salt is one or more of a salt of 1,3-dicaffeoylquinic acid, a salt of 1,4-dicaffeoylquinic acid, a salt of 1,5-dicaffeoylquinic acid, a salt of 3,4-dicaffeoylquinic acid, a salt of 3,5-dicaffeoylquinic acid, or a salt of 4,5-dicaffeoylquinic acid. (Aspect 9) 9. The steviol glycoside composition according to any one of claims 1 to 8, wherein 10% by weight or more, 25% by weight or more, or 50% by weight or more of the sensory modifier is dicaffeoylquinic acid and its salts. (Aspect 10) 10. The steviol glycoside composition of any one of the preceding claims, wherein the sensory modifier is a mixture having monocaffeoylquinic acid and salts of monocaffeoylquinic acid:dicaffeoylquinic acid and salts of dicaffeoylquinic acid in a ratio of 3:1 to 1:20, a ratio of 3:1 to 1:3, a ratio of 2:1 to 1:2, a ratio of 3:1 to 1:1, or a ratio of 2:1 to 1:1. (Aspect 11) 11. The steviol glycoside composition according to any one of the preceding claims, wherein the sensory modifier comprises 40% by weight to 60% by weight of dicaffeoylquinic acid and its salts. (Aspect 12) The steviol glycoside composition according to any one of Aspects 1 and 3 to 9, wherein 50% to 90% by weight, 50% to 80% by weight, 60% to 90% by weight, 60% to 80% by weight, or 65% to 75% by weight of the sensory modifier is in a salt form. (Aspect 13) 10. The steviol glycoside composition according to any one of claims 1 and 3 to 9, wherein at least 10% by weight, at least 20% by weight, between 20% by weight and 40% by weight, or between 25% by weight and 35% by weight of the sensory modifier is in acid form. (Aspect 14) 12. The steviol glycoside composition of any one of claims 2 to 11, wherein the salt fraction comprises at least 60% by weight of the total sensory modifier. (Aspect 15) 15. The steviol glycoside composition according to any one of aspects 2 to 14, wherein the salt fraction constitutes less than 90% by weight, less than 80% by weight, 60-80% by weight, or 65-75% by weight of the total sensory modifier. (Aspect 16) 16. The steviol glycoside composition of any one of claims 2 to 15, wherein the acid fraction comprises at least 10% by weight, at least 20% by weight, 20-40% by weight, or 20-40% by weight of the total sensory modifier. (Aspect 17) 17. The steviol glycoside composition of any one of the preceding claims, wherein the sensory modifier comprises a sodium salt of caffeoylquinic acid, a potassium salt of caffeoylquinic acid, or both. (Aspect 18) 18. The steviol glycoside composition of any one of the preceding claims, wherein the sensory modifier comprises a mixture of one or more potassium salts of caffeoylquinic acids and one or more sodium salts of caffeoylquinic acids. (Aspect 19) 19. The steviol glycoside composition of any one of claims 1 to 18, wherein the composition has a pH greater than the pH at the half-equivalence point of the sensory modifier. (Aspect 20) 20. The steviol glycoside composition of any one of claims 1 to 19, wherein the composition has a pH lower than the pH at the equivalence point of the sensory modifier. (Aspect 21) 21. The steviol glycoside composition of any one of the preceding claims, wherein the composition has a pH of less than 4.0, e.g., between 1.7 and 4.0. (Aspect 22) 22. The steviol glycoside composition of any one of the preceding claims, wherein the composition has a pH greater than 2.0 or greater than 2.5. (Aspect 23) 23. The steviol glycoside composition of any one of the preceding claims, wherein at least a portion of the sensory modifier is prepared from a plant source. (Aspect 24) 24. The steviol glycoside composition of claim 23, wherein the botanical source is yerba mate, rosemary, chicory, stevia, globe artichoke, coffee, or a mixture thereof. (Aspect 25) 23. The steviol glycoside composition of any one of the preceding claims, wherein at least a portion of the sensory modifier is prepared from yerba mate. (Aspect 26) 23. The steviol glycoside composition of any one of the preceding claims, wherein at least a portion of the sensory modifier is prepared from stevia. (Aspect 27) 27. The steviol glycoside composition of any one of the preceding claims, wherein the steviol glycoside component comprises rebaudioside D, rebaudioside M, or both. (Aspect 28) 2. The steviol glycoside composition of claim 1, wherein at least 80% or at least 90% by weight of the steviol glycoside component is rebaudioside M. (Aspect 29) 29. The steviol glycoside composition of any one of the preceding claims, wherein the composition comprises from 100 ppm to 1600 ppm of the steviol glycoside component. (Aspect 30) 30. The steviol glycoside composition of any one of the preceding claims, wherein the composition comprises at least 200 ppm, at least 300 ppm, between 200 ppm and 1000 ppm, or between 400 ppm and 800 ppm of the steviol glycoside component. (Aspect 31) 30. The steviol glycoside composition of any one of the preceding claims, wherein the composition comprises from 100 ppm to 1600 ppm of rebaudioside M. (Aspect 32) 2. The steviol glycoside composition of claim 1, wherein the composition comprises at least 200 ppm, at least 300 ppm, at least 500 ppm, between 200 ppm and 1000 ppm, or between 400 ppm and 800 ppm of rebaudioside M. (Aspect 33) 33. The steviol glycoside composition of any one of the preceding claims, wherein the composition comprises from 100 ppm to 1600 ppm of the sensory modifier. (Aspect 34) 2. The steviol glycoside composition of claim 1, wherein the composition comprises at least 200 ppm, at least 300 ppm, at least 500 ppm, between 200 ppm and 1000 ppm, or between 400 ppm and 800 ppm of the sensory modifier. (Aspect 35) 35. The steviol glycoside composition of any one of the preceding claims, wherein the composition comprises from 50 ppm to 1400 ppm of the salt of caffeoylquinic acid. (Aspect 36) 36. The steviol glycoside composition of any one of the preceding claims, wherein the composition comprises at least 100 ppm, at least 150 ppm, at least 250 ppm, or between 100 ppm and 900 ppm of a salt of caffeoylquinic acid. (Aspect 37) 2. The steviol glycoside composition according to claim 1, wherein the weight ratio of steviol glycoside components to sensory modifier is from 1:0.3 to 1:1. (Aspect 38) 37. The steviol glycoside composition according to any one of claims 2 to 36, wherein the weight ratio of steviol glycoside component to sensory modifier is from 1:0.3 to 1:1. (Aspect 39) 39. The steviol glycoside composition of any one of aspects 1-38, wherein the amount effective to reduce sweetness linger is determined by at least four panelists trained in tasting steviol glycoside compositions using a round table method using a scale of 0 to 6, where a score of 0 indicates no sweetness linger and a score of 6 indicates extreme sweetness linger, and the sweetness linger score is reduced by at least 1 unit, at least 2 units, or at least 3 units compared to a control sample not containing the sensory modifier. (Aspect 40) 40. The steviol glycoside composition of claim 39, wherein the amount of sensory modifier reduces the sweetness linger score to less than 3 units compared to a control sample not containing the sensory modifier. (Aspect 41) 41. The steviol glycoside composition of any one of claims 1 to 40, wherein the steviol glycoside composition has reduced sweetness linger compared to a control sample not containing the sensory modifier. (Aspect 42) 42. The steviol glycoside composition of any one of the preceding claims, wherein the amount effective to reduce bitterness is determined by at least four panelists trained in tasting steviol glycoside compositions using a round table method using a scale of 0 to 6, where a score of 0 indicates no bitterness and a score of 6 indicates extreme bitterness, and the bitterness score is reduced by at least 1 unit, at least 2 units, or at least 3 units compared to a control sample not containing the sensory modifier. (Aspect 43) 43. The steviol glycoside composition of claim 42, wherein the amount of sensory modifier reduces the bitterness score by less than 2 units or less than 1 unit compared to a control sample not containing the sensory modifier. (Aspect 44) 44. The steviol glycoside composition of any one of claims 1 to 43, wherein the steviol glycoside composition has a reduced bitterness compared to a control sample not containing the sensory modifier. (Aspect 45) 45. The steviol glycoside composition of any one of the preceding claims, wherein the composition is an aqueous solution. (Aspect 46) 46. The steviol glycoside composition of any one of the preceding claims, wherein the composition is in a solid form. (Aspect 47) 47. The steviol glycoside composition according to any one of the preceding claims, wherein the steviol glycoside components are present at a concentration of 200 to 1000 ppm and the sensory modifier is present at a concentration of 200 to 1000 ppm. (Aspect 48) 48. The steviol glycoside composition according to any one of the preceding claims, wherein the steviol glycoside components are present at a concentration of 400 to 800 ppm and the sensory modifier is present at a concentration of 400 to 800 ppm. (Aspect 49) A beverage comprising the steviol glycoside composition according to any one of aspects 1 to 48. (Aspect 50) 50. A method for reducing undesirable sensory properties of an aqueous solution of steviol glycosides, comprising preparing an aqueous solution of the composition described in any one of aspects 1-49. (Aspect 51) 51. The method of claim 50, wherein the undesirable sensory characteristic is bitterness, sweetness linger, sharp taste, harshness, astringency, or rebaudioside M type characteristics, or any combination thereof. (Aspect 52) 1. A method for reducing sweetness linger from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component; The method of claim 1, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form. (Aspect 53) 1. A method for reducing sweetness linger from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; The method, wherein the salt fraction comprises at least 50% by weight of the total sensory modifier. (Aspect 54) 1. A method for reducing bitterness from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component; The method of claim 1, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form. (Aspect 55) 1. A method for reducing bitterness from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; The method, wherein the salt fraction comprises at least 50% by weight of the total sensory modifier. (Aspect 56) 56. The method of any one of aspects 52 to 55, wherein the steviol glycoside component and the sensory modifier are added simultaneously. (Aspect 57) An aqueous solution of steviol glycosides having reduced sweetness linger, steviol glycoside components including at least one of rebaudioside D, rebaudioside M, and rebaudioside A, the total concentration of the steviol glycoside components being 200 ppm to 1000 ppm; A sensory modifier having a concentration of 200 ppm to 1000 ppm; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; the salt fraction constitutes 50-80% by weight of the total sensory modifier, and at least a portion of the sensory modifier is prepared from yerba mate or stevia; The aqueous steviol glycoside solution has a reduced sweetness linger compared to an aqueous steviol glycoside solution having the same concentration of steviol glycoside components without the sensory modifier. (Aspect 58) An aqueous solution of steviol glycosides having reduced bitterness, steviol glycoside components including at least one of rebaudioside D, rebaudioside M, and rebaudioside A, the total concentration of the steviol glycoside components being 400 ppm to 800 ppm; A sensory modifier at a concentration of 400 ppm to 800 ppm; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; the salt fraction constitutes 50-80% by weight of the total sensory modifier, and the acid fraction constitutes 20-50% by weight of the total sensory modifier; at least a portion of said sensory modifier is prepared from yerba mate or stevia; The aqueous steviol glycoside solution has a reduced bitter taste compared to an aqueous steviol glycoside solution having the same steviol glycoside component at the same concentration without the sensory modifier. (Aspect 59) 1. A steviol glycoside composition comprising: about 200 to about 800 ppm of steviol glycoside constituents comprising rebaudioside D and rebaudioside M, wherein rebaudioside M is at least 80% by weight of the steviol glycoside constituents; and about 200 to about 400 ppm of a sensory modifier, the sensory modifier being a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form, preferably 50% to 90%, 50% to 80%, or 60% to 90% by weight.
Claims
1. 1. A steviol glycoside composition, comprising: Steviol glycoside components, a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or both; 1. A steviol glycoside composition comprising: a) a weight ratio of steviol glycoside component to sensory modifier of from 1:0.3 to 1:3; or b) the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form, preferably 50% to 90%, 50% to 80%, or 60% to 90% by weight.
2. 1. A steviol glycoside composition, comprising: Steviol glycoside components, a sensory modifier in an amount effective to reduce sweetness linger, reduce bitterness, or both; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; a) the weight ratio of steviol glycoside component to sensory modifier is from 1:0.3 to 1:3; or b) the salt fraction constitutes at least 50% by weight of the sensory modifier, preferably from 50% to 90%, 50% to 80%, or 60% to 90% by weight of the sensory modifier.
3. 3. The steviol glycoside composition of claim 1 or 2, wherein the sensory modifier comprises one or more of 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid, and salts thereof.
4. 2. The steviol glycoside composition of claim 1, wherein the sensory modifier is a mixture of one or more monocaffeoylquinic acids or salts thereof and one or more dicaffeoylquinic acids or salts thereof.
5. 5. The steviol glycoside composition of claim 2 or 4, wherein the monocaffeoylquinic acid is one or more of 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, or 5-O-caffeoylquinic acid.
6. 5. The steviol glycoside composition of claim 2 or 4, wherein the mono-caffeoylquinate is one or more of a salt of 3-O-caffeoylquinic acid, a salt of 4-O-caffeoylquinic acid, or a salt of 5-O-caffeoylquinic acid.
7. 5. The steviol glycoside composition of claim 2 or 4, wherein the dicaffeoylquinic acid is one or more of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid.
8. 5. The steviol glycoside composition of claim 2 or 4, wherein the dicaffeoylquinic acid salt is one or more of a salt of 1,3-dicaffeoylquinic acid, a salt of 1,4-dicaffeoylquinic acid, a salt of 1,5-dicaffeoylquinic acid, a salt of 3,4-dicaffeoylquinic acid, a salt of 3,5-dicaffeoylquinic acid, or a salt of 4,5-dicaffeoylquinic acid.
9. 9. The steviol glycoside composition of claim 1, wherein at least 10% by weight, at least 25% by weight, or at least 50% by weight of the sensory modifier is dicaffeoylquinic acid and its salts.
10. 10. The steviol glycoside composition of claim 1, wherein the sensory modifier is a mixture having a ratio of monocaffeoylquinic acid and salts of monocaffeoylquinic acid:dicaffeoylquinic acid and salts of dicaffeoylquinic acid of 3:1 to 1:20, a ratio of 3:1 to 1:3, a ratio of 2:1 to 1:2, a ratio of 3:1 to 1:1, or a ratio of 2:1 to 1:
1.
11. 11. The steviol glycoside composition of claim 1, wherein the sensory modifier comprises 40% to 60% by weight of dicaffeoylquinic acid and its salts.
12. 10. The steviol glycoside composition of any one of claims 1 and 3-9, wherein 50% to 90%, 50% to 80%, 60% to 90%, 60% to 80%, or 65% to 75% by weight of the sensory modifier is in salt form.
13. 10. The steviol glycoside composition of any one of claims 1 and 3-9, wherein at least 10% by weight, at least 20% by weight, between 20% by weight and 40% by weight, or between 25% by weight and 35% by weight of the sensory modifier is in acid form.
14. 12. The steviol glycoside composition of claim 2, wherein the salt fraction comprises at least 60% by weight of the total sensory modifier.
15. 15. The steviol glycoside composition of claim 2, wherein the salt fraction comprises less than 90% by weight, less than 80% by weight, 60-80% by weight, or 65-75% by weight of the total sensory modifier.
16. 16. The steviol glycoside composition of any one of claims 2 to 15, wherein the acid fraction comprises at least 10% by weight, at least 20% by weight, 20-40% by weight, or 20-40% by weight of the total sensory modifier.
17. 17. The steviol glycoside composition of claim 1, wherein the sensory modifier comprises a sodium salt of caffeoylquinic acid, a potassium salt of caffeoylquinic acid, or both.
18. 18. The steviol glycoside composition of any one of claims 1 to 17, wherein the sensory modifier comprises a mixture of one or more potassium salts of caffeoylquinic acids and one or more sodium salts of caffeoylquinic acids.
19. 19. The steviol glycoside composition of claim 1, wherein the composition has a pH greater than the pH at the half-equivalence point of the sensory modifier.
20. 20. The steviol glycoside composition of claim 1, wherein the composition has a pH lower than the pH at the equivalence point of the sensory modifier.
21. 21. The steviol glycoside composition of any one of claims 1 to 20, wherein the composition has a pH of less than 4.0, for example, from 1.7 to 4.
0.
22. 22. The steviol glycoside composition of any one of claims 1 to 21, wherein the composition has a pH greater than 2.0 or greater than 2.
5.
23. 23. The steviol glycoside composition of any one of claims 1 to 22, wherein at least a portion of the sensory modifier is prepared from a plant source.
24. 24. The steviol glycoside composition of claim 23, wherein the botanical source is yerba mate, rosemary, chicory, stevia, globe artichoke, coffee, or a mixture thereof.
25. 23. The steviol glycoside composition of any one of claims 1 to 22, wherein at least a portion of the sensory modifier is prepared from yerba mate.
26. 23. The steviol glycoside composition of any one of claims 1 to 22, wherein at least a portion of the sensory modifier is prepared from stevia.
27. 27. The steviol glycoside composition of any one of claims 1 to 26, wherein the steviol glycoside component comprises rebaudioside D, rebaudioside M, or both.
28. 2. The steviol glycoside composition of claim 1, wherein at least 80% or at least 90% by weight of the steviol glycoside component is rebaudioside M.
29. 29. The steviol glycoside composition of any one of claims 1 to 28, wherein the composition comprises from 100 ppm to 1600 ppm of the steviol glycoside component.
30. 30. The steviol glycoside composition of any one of claims 1 to 29, wherein the composition comprises at least 200 ppm, at least 300 ppm, between 200 ppm and 1000 ppm, or between 400 ppm and 800 ppm of the steviol glycoside component.
31. 30. The steviol glycoside composition of any one of claims 1 to 29, wherein the composition comprises from 100 ppm to 1600 ppm of rebaudioside M.
32. 2. The steviol glycoside composition of claim 1, wherein the composition comprises at least 200 ppm, at least 300 ppm, at least 500 ppm, between 200 ppm and 1000 ppm, or between 400 ppm and 800 ppm of rebaudioside M.
33. 33. The steviol glycoside composition of any one of claims 1 to 32, wherein the composition comprises from 100 ppm to 1600 ppm of the sensory modifier.
34. 2. The steviol glycoside composition of claim 1, wherein the composition comprises at least 200 ppm, at least 300 ppm, at least 500 ppm, from 200 ppm to 1000 ppm, or from 400 ppm to 800 ppm of the sensory modifier.
35. 35. The steviol glycoside composition of any one of claims 1 to 34, wherein the composition comprises from 50 ppm to 1400 ppm of a salt of caffeoylquinic acid.
36. 36. The steviol glycoside composition of any one of claims 1 to 35, wherein the composition comprises at least 100 ppm, at least 150 ppm, at least 250 ppm, or between 100 ppm and 900 ppm of a salt of caffeoylquinic acid.
37. 2. The steviol glycoside composition of claim 1, wherein the weight ratio of steviol glycoside component to sensory modifier is from 1:0.3 to 1:
1.
38. 37. The steviol glycoside composition of any one of claims 2 to 36, wherein the weight ratio of steviol glycoside component to sensory modifier is from 1:0.3 to 1:
1.
39. 39. The steviol glycoside composition of claim 1, wherein the amount effective to reduce sweetness linger is determined by at least four panelists trained to taste steviol glycoside compositions using a round table method using a scale of 0 to 6, where a score of 0 indicates no sweetness linger and a score of 6 indicates extreme sweetness linger, and the sweetness linger score is reduced by at least 1 unit, at least 2 units, or at least 3 units compared to a control sample not containing the sensory modifier.
40. 40. The steviol glycoside composition of claim 39, wherein the amount of sensory modifier reduces a sweetness linger score by less than 3 units compared to a control sample not containing the sensory modifier.
41. 41. The steviol glycoside composition of any one of claims 1 to 40, wherein the steviol glycoside composition has reduced sweetness linger compared to a control sample not containing the sensory modifier.
42. 42. The steviol glycoside composition of claim 1, wherein the amount effective to reduce bitterness is determined by at least four panelists trained to taste steviol glycoside compositions using a round table method using a scale of 0 to 6, where a score of 0 indicates no bitterness and a score of 6 indicates extreme bitterness, and the bitterness score is reduced by at least 1 unit, at least 2 units, or at least 3 units compared to a control sample not containing the sensory modifier.
43. 43. The steviol glycoside composition of claim 42, wherein the amount of sensory modifier reduces a bitterness score by less than 2 units or less than 1 unit compared to a control sample not containing the sensory modifier.
44. 44. The steviol glycoside composition of any one of claims 1 to 43, wherein the steviol glycoside composition has a reduced bitter taste compared to a control sample not containing the sensory modifier.
45. 45. The steviol glycoside composition of any one of claims 1 to 44, wherein the composition is an aqueous solution.
46. 46. The steviol glycoside composition of any one of claims 1 to 45, wherein the composition is in a solid form.
47. 47. The steviol glycoside composition of any one of claims 1 to 46, wherein the steviol glycoside component is at a concentration of 200 to 1000 ppm and the sensory modifier is at a concentration of 200 to 1000 ppm.
48. 48. The steviol glycoside composition of any one of claims 1 to 47, wherein the steviol glycoside component is at a concentration of 400 to 800 ppm and the sensory modifier is at a concentration of 400 to 800 ppm.
49. A beverage comprising the steviol glycoside composition of any one of claims 1 to 48.
50. 50. A method for reducing undesirable sensory properties of an aqueous solution of steviol glycosides, comprising preparing an aqueous solution of the composition of any one of claims 1 to 49.
51. 51. The method of claim 50, wherein the undesirable sensory characteristic is bitterness, sweetness linger, sharp taste, harshness, astringency, or rebaudioside M type characteristics, or any combination thereof.
52. 1. A method for reducing sweetness linger from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component; The method of claim 1, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form.
53. 1. A method for reducing sweetness linger from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the sweetness linger of the steviol glycoside component; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; The method, wherein the salt fraction comprises at least 50% by weight of the total sensory modifier.
54. 1. A method for reducing bitterness from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component; The method of claim 1, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form.
55. 1. A method for reducing bitterness from a steviol glycoside component in an edible composition, comprising combining the steviol glycoside component with a sensory modifier in an amount effective to reduce the bitterness of the steviol glycoside component; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; The method, wherein the salt fraction comprises at least 50% by weight of the total sensory modifier.
56. 56. The method of any one of claims 52 to 55, wherein the steviol glycoside component and the sensory modifier are added simultaneously.
57. An aqueous solution of steviol glycosides having reduced sweetness linger, steviol glycoside components comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside A, wherein the total concentration of the steviol glycoside components is from 200 ppm to 1000 ppm; a sensory modifier at a concentration of 200 ppm to 1000 ppm; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; the salt fraction comprises 50-80% by weight of the total sensory modifier, at least a portion of which is prepared from yerba mate or stevia; The aqueous steviol glycoside solution has a reduced sweetness linger compared to an aqueous steviol glycoside solution having the same concentration of steviol glycoside components without the sensory modifier.
58. An aqueous solution of steviol glycosides having reduced bitterness, steviol glycoside components comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside A, wherein the total concentration of the steviol glycoside components is between 400 ppm and 800 ppm; a sensory modifier at a concentration of 400 ppm to 800 ppm; the sensory modifier comprises a salt fraction and an acid fraction; the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid; the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid; the salt fraction comprises 50-80% by weight of the total sensory modifier and the acid fraction comprises 20-50% by weight of the total sensory modifier; at least a portion of said sensory modifier is prepared from yerba mate or stevia; The aqueous steviol glycoside solution has a reduced bitter taste compared to an aqueous steviol glycoside solution having the same steviol glycoside component at the same concentration without the sensory modifier.
59. 1. A steviol glycoside composition comprising: from about 200 to about 800 ppm of a steviol glycoside component comprising rebaudioside D and rebaudioside M, wherein rebaudioside M is at least 80% by weight of said steviol glycoside component; and about 200 to about 400 ppm of a sensory modifier, the sensory modifier being a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, wherein at least 50% by weight of the sensory modifier is in salt form, preferably 50% to 90%, 50% to 80%, or 60% to 90% by weight.
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