WO2022221250A1

WO2022221250A1 - Novel compositions for taste masking

Info

Publication number: WO2022221250A1
Application number: PCT/US2022/024377
Authority: WO
Inventors: Diana KLASER CHENG; Michell Eve HUBER; Hassan Mustaq UBAIDEEN
Original assignee: International Flavors & Fragrances Inc.
Priority date: 2021-04-12
Filing date: 2022-04-12
Publication date: 2022-10-20

Abstract

Novel compositions and methods are provided for masking off-taste in a consumable such as astringency, sourness, bitterness, the lingering aftertaste in steviol glycoside and the beany off-taste in plant-based protein.

Description

NOVEL COMPOSITIONS FOR TASTE MASKING Status of Related Application

This application claim priority to U.S. Provisional Patent Application No. 63/173,682, filed April 12, 2021, the contents hereby incorporated by reference as if set forth in its entirety.

Field of the Invention The present invention relates to novel compositions and methods for masking off-taste in a consumable.

Background of the Invention

Food industry has made significant effort to modify and harmonize taste as well as to eliminate and reduce off-taste in food products. The basic categories of taste are salty, sweet, sour, bitter and urn ami. Additional taste may also include, for example, metallic, burning, pungent, astringent and many more. Accordingly, the categories of off-taste are very broad and include any unwanted taste. The discovery of new taste modifiers that mask unpleasant off-taste enables the creation of well-balanced flavors. For example, there has been increasing concern about high levels of consumption of both fat and sugar, and a corresponding concern about lower levels of animal- based protein consumption. The food industry has addressed those concerns by providing a variety of products enriched with proteins isolated from plants. Flowever, plant proteins available in the market have undesirable astringent and strong off-taste due to, for example, polyphenols, flavonoids, isoflavones, terpenes and glucosinolates associated therewith. Removal of these components in the production of protein concentrates and plant protein isolates is one approach but these components have a number of health benefits and their removal increases processing costs. Otherwise, more sugar or fat is added to cover bitterness and adjust flavor perception. Flavorists simply “over flavor” their products to hide the offending taste. This approach is wholly unsatisfactory, especially for health-conscious consumers where reduced fat and sugar content is a common goal. As an alternative, artificial sweeteners and some other sugar substitutes such as steviol glycosides are used as noncaloric sweeteners to substitute sugar. Flowever, these non sugar sweeteners themselves also leave unpleasant lingering flavor such as bitter and metallic aftertaste, which limits their applications in consumables. Therefore, other approaches for masking various off-taste such as, for example, astringency, sourness, bitterness, lingering aftertaste and beaniness have been sought. Summary of the Invention

This invention provides novel compositions and methods for use thereof in masking off- taste in a consumable such as astringency, sourness, bitterness, the lingering aftertaste in steviol glycoside and the beany off-taste in plant-based protein.

In one embodiment, the present invention is directed to a method of masking off-taste in a consumable by adding an olfactory effective amount of a compound represented by Formula I:

Formula I wherein R¹ is FI or -CFh, and R², R³ and R⁴ are each independently absent or selected from the group consisting of -OF! and -OCFh; a salt thereof; or a mixture thereof to the consumable. In another embodiment, the present invention is directed to a method of masking off-taste in a consumable by adding an olfactory effective amount of 2-(benzyloxy)-6-(((3,4-dihydroxy-4- (hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2Fl-pyran-3,4,5-triol to the consumable. In another embodiment, the present invention is directed to a consumable comprising an olfactory effective amount of the compound of Formula I, wherein the consumable has off-taste of astringency, sourness, bitterness, lingering aftertaste or beany off-taste.

In another embodiment, the present invention is directed to a consumable comprising an olfactory effective amount of 2-(benzyloxy)-6-(((3,4-dihydroxy-4-

(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2Fl-pyran-3,4,5-triol, wherein the consumable has off-taste of astringency, sourness, bitterness, lingering aftertaste or beany off-taste.

These and other embodiments of the present invention will be apparent by reading the following specification. Detailed Description of the Invention

Formula I of the present invention is illustrated, for example, by following examples.

2-(Benzyloxy)-6-(((3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2- yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (Structure 1)

2-(((3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-6-((4- methoxybenzyl)oxy)tetrahydro-2H-pyran-3,4,5-triol (Structure 2)

2-(((3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-6-((4-hydroxy- 3-methoxybenzyl)oxy)tetrahydro-2H-pyran-3,4,5-triol (Structure 3)

2-(((3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-6-((3,4,5- trimethoxybenzyl)oxy)tetrahydro-2H-pyran-3,4,5-triol (Structure 4)

Those with skill in the art will recognize that Formula I of the present invention contains chiral centers, thereby providing a number of isomers. It is intended herein that the compounds described herein include the isomeric mixtures, as well as individual isomers that may be separated using techniques known to those having skill in the art. Suitable techniques include chromatography such as high-performance liquid chromatography, referred to as HPLC, and particularly gel chromatography and solid phase microextraction, referred to as SPME. For example, Structure 1 includes (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((((2R,3R,4R)-3,4-dihydroxy-4- (hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (icariside F2, CAS No. 115009-57-9), (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((((2S,3R,4R)-3,4-dihydroxy-4- (hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol, (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((((2R,3R,4S)-3,4-dihydroxy-4-

(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol, and a mixture thereof. The intensity of a sour taste in a consumable is determined by both free hydrogen ions and undissociated hydrogen ions, which are approximately equal in the sour taste on a molar basis (Li, et al. Food Chem. 2005, 185:200-204). Hosokawa, et al. use amino acids including proline, aspartic acid and glutamic acid to modify the sourness of a citrus fruit drink but there remain problems such as unpleasant aftertaste, discolored products as well as unpleasant smell (JP 58- 138363). Sugar provides sweetness and also masks off-flavors such as bitterness and sourness.

However, reduced use of sugar in consumables is driven by consumer interest in eating healthier foods. As one example, by employing a sweetener or a sweetness enhancer such as 2-(benzyloxy)- 6-(((3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (WO 2012/107207), less sugar is needed to achieve a desired sweetness level, which may result in less calories. But unlike sugar, non-sugar sweeteners or sweetness enhancers generally have no effect in masking off-flavors. Thus, when less sugar is used in the presence of non-sugar sweeteners or sweetness enhancers in consumables such as fruit juices, yogurt, and plant protein beverages, additional compositions remain needed to balance the sour taste and astringent mouthfeel. A consumable acid is an acid that is edible or suitable for human consumption at a given amount. A consumable acid includes, for example, but not limited to, acetic acid, allantoic acid, a-ketoglutaric acid, ascorbic acid, aspartic acid, benzoic acid, cetostearic acid, citramalic acid, citric acid, formic acid, fumaric acid, galacturonic acid, glucoronic acid, glutamic acid, glyceric acid, glycolic acid, hydrochloric acid, isocitric acid, lactic acid, lactarimic acid, lactoisocitric acid, malic acid, oxalacetic acid, oxalic acid, phosphoric acid, pyroglutamic acid, pyrrolidinonecarboxylic acid, pyruvic acid, quinic acid, shikimic acid, succinic acid, sulphuric acid and tartaric acid. A consumable acid is a flavor compound that contributes to the sour taste of a consumable. The term “a consumable acid” is understood to mean one or more of the consumable acids as described herein. A consumable acid may cause undesirable sour and astringent off-taste.

Artificial sweeteners and other sugar substitutes are commonly used in diet to reduce the sugar and calories. Sugar substitutes are any non-sugar sweeteners. Artificial sweeteners are considered one type of sugar substitutes. Some popular artificial sweeteners include acesulfame potassium, aspartame, neotame, saccharin, sucralose and advantame. Other popular sugar substitutes include sugar alcohols such as erythritol, hydrogenated starch hydrolysate, isomalt, lactitol, maltitol, mannitol, sorbitol and xylitol; natural sweeteners such as agave nectar, date sugar, fruit juice concentrate, honey, maple syrup and molasses; and other sweeteners such as steviol glycosides, tagatose and trehalose. Steviol glycosides are natural constituents of the plant Stevia rebaudiana ( S . rebaudiand), which belongs to the sunflower family ( Compositae or Asteraceae). The leaves of S. rebaudiana contain different steviol glycosides. Steviol glycosides also occur in the related species Stevia phlebophylla and in the plant Rubus chingii of the rose family ( Rosaceae ). A steviol glycoside is understood to mean a naturally occurring compound as described above or a derivative thereof. The steviol glycoside of the present invention includes, for example, but not limited to, steviolmonoside, steviol- 19-0-P-D-glucosidc, rubusoside, steviolbioside, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, dulcoside B, isostcviol- 19-0-P-D-glucosidc, 1 S -hydroxy rubusoside, 15-oxorubusoside, suavioside A, suavioside B, suavioside Cl, suavioside C2, suavioside Dl, suavioside D2, suavioside E, suavioside F, suavioside G, suavioside H, suavioside I, suavioside J, suavioside K, suavioside L, suavioside Ql, suavioside Q2, suavioside Rl, suavioside R2, suavioside SI, suavioside S2, 9-hydroxysuavioside H, 9-hydroxysuavioside J, 15-oxosuavioside L, 15-oxo-16- epi-suavioside L, 16P-hydroxysuaviosidc L, 16a-hydroxysuavioside L, paniculoside IV, sugeroside, a derivative such as a glycosylated derivative thereof and a combination thereof. The glycosylated derivatives can be prepared via transglycosylation reactions with, for example, but not limited to, glucose, fructose, galactose, rhamnose, ribose, mannose, arabinose, fucose, maltose, lactose, sucrose, rutinose, sorbose, xylulose, ribulose, rhammulose and xylose. These sugar substitutes exhibit undesirable taste attributes such as lingering bitter and metallic aftertaste. A plant protein is understood to mean a plant protein-containing material. There is a recent rise in popularity of plant proteins. Plant-based food products containing the plant proteins are generally more affordable. They are also perceived by customers as the healthy and sustainable alternatives to animal meat products. The plant proteins available in the market include, for example, but not limited to, soy protein, pea protein, wheat protein, oat protein, corn protein, peanut protein, silk protein, rice protein, almond protein, walnut protein, flaxseed protein, red bean protein, sunflower seed protein, mung bean protein, pumpkin seed protein, watermelon seed protein, highland barley protein, hemp protein, mushroom protein, shiitake protein, algae protein, tomato seed protein, rapeseed protein, potato protein, sacha inchi protein, fava protein, millet protein, lotus seed protein, black soybean protein and white kidney protein. However, plant proteins have undesirable bitter, astringent and beany off-taste.

A preservative is understood to mean a compound that prevents the degradation or breakdown of a composition or another compound. For example, a preservative eliminates or inhibits micro-organism such as yeast, fungi, bacteria or mold. The preservative of the present invention includes ail preservatives approved for use in food and/or beverage compositions such as chemical preservatives including benzoates, sorbates (e.g., potassium sorbate, calcium sorbate and sodium sorbate), propionates, nitrites and phosphates (e.g., calcium phosphate); antioxidants including sulfites (e.g., sodium sulfite, sodium bisulfite, sodium metabisulfite, potassium bisulfite and potassium metabisulfite), vitamin E (tocopherol), vitamin C (ascorbic acid) and butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT); chelating agents including disodium ethylenediaminetetraacetic acid (EDTA), polyphosphates (e.g., sodium hexametaphosphate) and citric acid; and a mixture thereof. A preservative may exhibit undesirable sour and astringent off- taste.

Thus, it is of particular need to develop taste modifiers that mask the unpleasant off-taste in a consumable such as astringency, sourness, bitterness, the lingering aftertaste in steviol glycoside and the beany off-taste in plant-based protein. US 2002/0193342 A1 describes the addition of sucralose to a product to mask the unpleasant taste of an amino acid component other than arginine. WO 2017/037181 A1 teaches the use of one or more off-note blocking compounds including fatty acids, carbonyls, sweet brown, esters, sweeteners, lactones and juice derivatives to block, mask or modify the undesirable off-note of a non-animal derived protein. Bertelsen, et al. (/. Sci. Food Agric. (2018) 98(10): 3860-3869) describe xylitol, sucrose, a-cyclodextrin, and maltodextrin as bitter-masking agents of an enzyme- treated soy protein in an aqueous model and in a bread model. GB 201304301 DO teaches the addition of octadecalactone to a consumable product base to reduce off-taste such as the bitterness of whey protein or high-intensity sweeteners. US 9,668,505 B2 describes edible films and gummi confectioneries including, e.g., fruit flavors, GSB Natural Masking Agent, hydrogenated and ethoxylated glycerol esters, and nucleotides that mask the taste of bitter tasting foods and/or foods that contain proteins. Further, EP 2058297 Al describes the use of alkamides for masking the astringent taste of an unpleasantly tasting substance.

Compounds of the present invention can be synthesized or extracted from a plant. 2- (Benzyloxy)-6-(((3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2yl)oxy)methyl)tetrahydro- 2H-pyran-3,4,5-triol (Structure 1), which is now identified in Adenophora stenanthina, has never been reported previously. Roots of Adenophora species including Adenophora stenanthina are used in traditional Chinese medicine for maintaining or improving respiratory wellness. An isomer of Structure 1, icariside F2, has been identified in various plants such as, for example, but not limited to Angelica sinensis, Annona squamosa, Apium graveolens, Atractylodes japonica, Atractylodes lancea, Bretschneidera sinensis, Bupleurum falcatum, Camellia sinensis, Canthium berberidifolium, Clausena lansium, Coriandrum sativum, Crepidiastrum lanceolatum, Dendrophthoe pentandra, Dioecrescis erythroclada, Epimedium diphyllum, Epimedium grandiflorum, Eucommia ulmoides, fennel, Ficus elastica, Foeniculum vulgare, Glehnia littoralis, Globularia alypum, Glochidion assamicum, Glochidion rubrum, Goldfussia pentstemonoides, Grevillea robusta, Helichrysum arenarium, Holmskioldia sanguinea, Hylomecon vernalis, Illicium oligandrum, Lemna paucicostata, Ligusticum chuanxiong, Ligusticum sinensis, Lychnophora ericoides, Magnolia thailandica, Petroselinum crispum (parsley), Phyllodium pulchellum, Picrasma quassioides, Pimpinella anisum, Piper retrofractum, Prunus padus (Rosaceae), Pyrus bourgaeana, Rhododendron brachycarpum, Sanchezia nobilis, Salvia officinalis (sage), Serissa japonica, Solenostemma argel, strawberry, Vitis vinifera, Xanthoxylum piperitum and Zanthoxylum schinifolium. Icariside F2 is also found in plants or extracts having possible medicinal uses. For example, Helichrysum arenarium is used as a folk medicine to treat the disease of digestive system (Wang, et al., Zhongguo Yaowu Huaxue Zazhi (2012), 22(3):220-222, 226). Potential anti- inflammatory, anti-septic, antitumor and cytotoxic activities of icariside F2 are also reported (Bai, et al., J. Agric. Food Chem. (2015) 63(8):2198-2205; Ma et al., Carbohydr. Res. (2011) 346(9): 1165-1168; Yoo, et al, J. Funct. Foods (2015) 16:448-459; Peng, et al., Molecules (2019) 24(17):3124; Lee, et al., Arch. Pharm. Res. (2012) 35(3):415-421; Curr. Org. Chem. (2008) 12(18): 1648-1660). In addition, icariside F2 is proposed as an agent for skin-lightening and anti chloasma (Yamashita-Higuchi, et al, Chem. Pharm. Bull. (2014) 62(4):364-372). Further, icariside F2 may function as a flavor and aroma precursor in pepper, tea and tobacco (Jiang, et al. , J. Agric. Food Chem. (2001) 49(12):5888-5894; Sakata, et al., Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (1996), 38^th: 511-516; Wu, et al, Sepu (2009), 27(6):820-824).

However, nothing in the prior art teaches the off-taste masking effect of any of these compounds. It has now been surprisingly discovered that Formula I of the present invention is effective in masking the off-taste in a consumable such as astringency, sourness, bitterness, the lingering aftertaste in steviol glycoside and the beany off-taste in plant-based protein. Particularly, 2-(benzyloxy)-6-(((3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2yl)oxy)methyl)tetrahydro- 2H-pyran-3,4,5-triol (Structure 1) has demonstrated unexpected and superior masking effect of the off-taste in a consumable such as astringency, sourness, bitterness, the lingering aftertaste in steviol glycoside and the beany off-taste in plant-based protein.

The term “a salt thereof’ is understood to include, for example, but not limited to, a monohydrate salt or solvate. A salt can also be formed between a cation and a negatively charged group; examples of a suitable cation include sodium ion, potassium ion, magnesium ion, calcium ion, iron ion, and an ammonium cation such as tetramethylammonium ion. A salt further includes those containing quaternary nitrogen atoms. A solvate refers to a complex formed between an active compound and a pharmaceutically acceptable solvent. Examples of a pharmaceutically acceptable solvent include water, ethanol, isopropanol, ethyl acetate, acetic acid, ethanolamine, or a mixture thereof.

The component having astringency, sourness, bitterness, the lingering aftertaste and the beany off-taste can be an acid, carbohydrate sweetener, artificial sweetener, protein or preservative that is inherently present in the consumable ( e.g ., in food products containing fruits and fermented foods and beverages such as yogurt and wine) or said component is added to the consumable. In certain embodiments, the component having sour off-taste is a consumable acid. In other embodiments, the component having bitter, astringent and beany off-taste is a protein. A protein with bitter, astringent and beany off-taste can include an amino acid, protein hydrolysate or protein component of a consumable, in particular a plant protein or milk of grass-eating animals. In other embodiments, the component having unwanted lingering aftertaste is a sweetener. Sweeteners of the present invention include, but are not limited to, carbohydrate sweeteners such as sucrose, fructose, glucose, high fructose corn syrup (containing fructose and glucose), xylose, allulose, arabinose, rhamnose, and sugar alcohols, such as erythritol, xylitol, mannitol, sorbitol, inositol, or artificial sweeteners and some other sugar substitutes as described above, or a combination thereof. In other embodiments, the component having sour and astringent off-taste is a preservative. Examples of preservatives include, for example, but are not limited to, benzoates, sorbates, propionates, nitrites and phosphates.

The term “mask” or “masking” is understood to mean the covering, disguising, and/or obscuring an astringent, bitter, and/or off-flavor by the addition of a compound of Formula I, wherein the component associated with the astringency, sourness, bitterness, lingering aftertaste and the beany off-taste remains unchanged, but its unpleasant taste is not perceived by a human consuming said consumable.

The term “olfactory effective amount” is understood to mean the amount of a compound used in a consumable to mask the off-taste in a consumable, wherein the compound reduces and/or suppresses the off-taste such as astringency, sourness, bitterness, the lingering aftertaste in steviol glycoside and the beany off-taste in plant-based protein. The olfactory effective amount may vary depending on many factors including other ingredients, their relative amounts and the olfactory effect that is desired. Any amount of an off-taste masking compound that provides the desired degree of off-taste masking effect without exhibiting any off-taste can be used.

In the present invention, when added to a consumable as an exogenous additive, in pure form or as plant extract, Formula I is used in an amount effective to reduce or suppress the off-taste of a component of the consumable having astringency, sourness, bitterness, the lingering aftertaste and the beany off-taste. In certain embodiments, the olfactory effective amount ranges from about 0.1 parts per billion to about 2000 parts per million by weight, more preferably from about 1 part per billion to about 1000 parts per million by weight, even more preferably from about 10 parts per billion to about 500 parts per million by weight. The term “ppb” is understood to mean part per billion by weight. The term “ppm” is understood to mean part per million by weight. Additional materials can also be used in conjunction with the compounds of the present invention to encapsulate and/or deliver the off-taste masking effect. Some well-known materials are, for example, but not limited to, polymers, oligomers, other non-polymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars and solid surface materials such as zeolite and silica. Some preferred polymers include polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum arabic, alginate, chitosan, polylactide, poly(melamine-formaldehyde), poly(urea-formaldehyde), or a combination thereof.

A consumable includes, for example, a food product (e.g., a beverage), a sweetener such as a natural sweetener or an artificial sweetener, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product.

In some embodiments, a consumable is a food product including, for example, but not limited to, fruits, vegetables, juices, meat products such as ham, bacon and sausage, egg products, fruit concentrates, gelatins and gelatin-like products such as jams, jellies, preserves and the like, milk products such as ice cream, sour cream and sherbet, icings, syrups including molasses, corn, wheat, rye, soybean, pea, mung bean, oat, rice and barley products, nut meats and nut products, cakes, cookies, confectionaries such as candies, gums, fruit flavored drops, and chocolates, chewing gums, mints, creams, pies and breads. In a certain embodiment, the food product is a beverage including, for example, but not limited to, coffee, tea, carbonated soft drinks, such as COKE and PEPSI, non-carbonated soft drinks and other fruit drinks, sports drinks such as GATORADE and alcoholic beverages such as beers, wines and liquors. A consumable also includes prepared packaged products, such as granulated flavor mixes, which upon reconstitution with water provide non-carbonated drinks, instant pudding mixes, instant coffee and tea, coffee whiteners, malted milk mixes, pet foods, livestock feed, tobacco, and materials for baking applications, such as powdered baking mixes for the preparation of breads, cookies, cakes, pancakes, donuts and the like. A consumable also includes diet or low-calorie food and beverages containing little or no sucrose. A preferred consumable includes carbonated beverages. Consumables further include condiments such as herbs, spices and seasonings such as sauces and gravies, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners. In other embodiments, a consumable is a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition or a cosmetic product. Preferred compositions are pharmaceutical compositions containing naringenin, one or more pharmaceutically acceptable excipients, and one or more active agents that exert a biological effect other than sweetness enhancement. Such active agents include pharmaceutical and biological agents that have an activity other than taste enhancement. Such active agents are well known in the art (See, e.g., The Physician's Desk Reference). Such compositions can be prepared according to procedures known in the art, for example, as described in Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton, PA. In one embodiment, such an active agent includes a bronchodilator, an anorexiant, an antihistamine, a nutritional supplement, a laxative, an analgesic, an anesthetic, an antacid, a H2 -receptor antagonist, an anticholinergic, an antidiarrheal, a demulcent, an antitussive, an antinauseant, an antimicrobial, an antibacterial, an antifungal, an antiviral, an expectorant, an anti-inflammatory agent, an antipyretic and a mixture thereof. In another embodiment, the active agent is selected from the group consisting of an antipyretic and analgesic, e.g., ibuprofen, acetaminophen or aspirin, a laxative, e.g., phenolphthalein dioctyl sodium sulfosuccinate, an appetite depressant, e.g., an amphetamine, phenylpropanolamine, phenylpropanolamine hydrochloride, or caffeine, an antacid, e.g., calcium carbonate, an antiasthmatic, e.g., theophylline, an antidiarrheal, e.g., diphenoxylate hydrochloride, an agent against flatulence, e.g., simethecon, a migraine agent, e.g., ergotamine tartrate, a psychopharmacological agent, e.g., haloperidol, a spasmolytic or sedative, e.g., phenobarbital, an antihyperkinetic, e.g., methyldopa or methylphenidate, a tranquilizer, e.g., a benzodiazepine, hydroxyzine, meprobramate or phenothiazine, an antihistaminic, e.g., astemizol, chlorpheniramine maleate, pyridamine maleate, doxl amine succinate, brompheniramine maleate, phenyltoloxamine citrate, chlorcyclizine hydrochloride, pheniramine maleate, or phenindamine tartrate, a decongestant, e.g., phenylpropanolamine hydrochloride, phenylephrine hydrochloride, pseudoephedrine hydrochloride, pseudoephedrine sulfate, phenylpropanolamine bitartrate, or ephedrine, a beta-receptor blocker, e.g., propranolol, an agent for alcohol withdrawal, e.g., disulfuram, an antitussive, e.g., benzocaine, dextromethorphan, dextromethorphan hydrobromide, noscapine, carbetapentane citrate, and chlophedianol hydrochloride, a fluorine supplement, e.g., sodium fluoride, a local antibiotic, e.g., tetracycline or clindamycin, a corticosteroid supplement, e.g., prednisone or prednisolone; an agent against gout, e.g., colchicine or allopurinol, an antiepileptic, e.g., phenytoin sodium, an agent against dehydration, e.g., electrolyte supplements, an antiseptic, e.g., cetylpyridinium chloride, a NSAID, e.g., acetaminophen, ibuprofen, naproxen, or a salt thereof, a gastrointestinal active agent, e.g., loperamide and famotidine, an alkaloid, e.g., codeine phosphate, codeine sulfate, or morphine, a supplement for trace elements, e.g., sodium chloride, zinc chloride, calcium carbonate, magnesium oxide, and other alkali metal salts and alkali earth metal salts; a vitamin, an ion-exchange resin, e.g., cholestyramine, a cholesterol-depressant and lipid-lowering substance, an antiarrhythmic, e.g., N-acetylprocainamide and an expectorant, e.g., guaifenesin. Examples of dietary supplements or nutraceuticals include, for example, but are not limited to, an enteral nutrition product for treatment of nutritional deficit, trauma, surgery, Crohn's disease, renal disease, hypertension, obesity and the like, to promote athletic performance, muscle enhancement or general well-being or inborn errors of metabolism such as phenylketonuria. In particular, such compositions can contain one or more amino acids which have a bitter or metallic taste or aftertaste. Such amino acids include, for example, but are not limited to, an essential amino acid such as L isomers of leucine, isoleucine, histidine, lysine, methionine, phenylalanine, threonine, tryptophan, tyrosine and valine. Dental hygienic compositions are known in the art and include, for example, but not limited to, a toothpaste, a mouthwash, a plaque rinse, a dental floss, a dental pain reliever (such as ANBESOL) and the like. In one embodiment, the dental hygienic composition includes one natural sweetener. In another embodiment, the dental hygienic composition includes more than one natural sweetener. In yet another embodiment, the dental hygienic composition includes sucrose and corn syrup, or sucrose and aspartame. A cosmetic product includes, for example, but not limited to, a face cream, a lipstick, a lip gloss and the like. Other suitable cosmetic products of use in this invention include a lip balm, such as CHAPSTICK or BURT’S BEESWAX Lip Balm.

The invention is described in greater detail by the following non-limiting examples. Materials were purchased from Aldrich Chemical Company unless noted otherwise.

Example I: Preparation of Plant Extract

Plant extract of Adenophora stenanthina root can be obtained by processes such as, for example, but not limited to, ethanol precipitation of aqueous root extract followed by extraction of aqueous root extract with aqueous ethanol solution, and enzyme hydrolysis of root powder and extract.

A carbohydrase (commercially available from Novozymes) was added to a solution of Adenophora stenanthina root powder (commercially available from AuNutra Industries Inc.). The mixture was heated to and maintained at a temperature ranging from 30 to 65 °C with agitation for 4-24 hours. The temperature was raised to 65-85 °C for about 30 minutes before the reaction mixture was cooled to room temperature. The resulting mixture was filtered under vacuum. Solvent was removed by rotary evaporation under reduced pressure to provide plant extract in dry powder form. Plant extract powder may also be obtained by spray drying the resulting mixture with a carrier such as, for example, gum acacia, maltodextrin, or tapioca starch.

Alternatively, the root extract of Adenophora stenanthina was dissolved in water at a weight ratio from 1 : 1 to 1 : 10 with heating. Ethanol was added at a weight ratio of ethanol to water from 5:1 to 10:1 to provide a precipitate. The precipitate was collected through centrifugation or filtration and dried under vacuum at about 40 °C to provide plant extract containing icariside F2 from about 0.001 to about 0.5% by weight.

In addition, icariside F2 was purchased (commercially available at Sigma- Aldrich Corp.).

Example II: Preparation of Base Solutions and Test Samples

A sucrose solution (4%) was prepared in water.

Just Cranberry^® Juice was used to make a 10% cranberry juice base solution.

A steviol glycoside base solution was prepared in water at a concentration of 0.08%. In addition, Vitaminwater® Zero revive fruit punch was purchased.

Soy protein base solutions were prepared in water at concentrations of 1 and 5%.

Pea protein base solutions (NUTRALYS^®, commercially available at Roquette America Inc.) were prepared in water at concentrations of 1 and 5%.

Citric acid base solutions were prepared in water at concentrations of 0.05 and 0.08%.

An astringency base solution was prepared in water containing 0.08% citric acid and 0.02% tannic acid.

2014 Rosemount Estate Diamond Label Shiraz (South Eastern Australia) was purchased and used as an alcoholic beverage base.

A plant protein burger containing pea protein, mung bean protein and rice protein was prepared with a total protein level at 15-20%.

A sodium benzoate solution was prepared in water at a concentration of 0.015% and used as a preservative base.

Base solutions served as controls. Icariside F2 and plant extract (prepared according to Example I) were each diluted in various base solutions to provide test samples of different concentrations. Example III: Organoleptic Properties of Structure 1 Compound

The inherent organoleptic properties of icariside F2 were evaluated in water and are reported in the following:

Icariside F2 exhibited very slight astringency at 0.01 ppm or higher in water.

In addition, the organoleptic properties of icariside F2 in sucrose solution (prepared according to Example II) were further evaluated and are reported in the following:

Icariside F2 exhibited very slight astringency at 0.1 ppm or higher in sucrose solution (4%). Icariside F2 did not alter the taste profile of sucrose solution. Example IV : Off-taste Masking in Fruit Juice

Cranberry juice base solution tasted sour, astringent and puckering notes. Test samples were prepared in cranberry juice base solution containing (i) icariside F2 ranging from 0.0001 to 1.5 ppm; and (ii) icariside F2-containing plant extract at 25, 50 and 100 ppm, respectively. The off-taste of fruit juice was evaluated using a scale of 0 to 10, where 0 = none, 1-2 = very weak, 3-4 = weak, 5-6 = moderate, 7-8 = strong, and 9-10 = extremely strong. Averaged scores and taste profile of the control and test samples are reported in the following:

Icariside F2 and icariside F2-containing plant extract both reduced the sourness of cranberry juice.

Example V : Off-Taste Masking in Steviol Glycoside Solution

Steviol glycoside base solution (prepared according to Example II) and Vitaminwater® Zero revive fruit punch both showed green off-note with lingering aftertaste. Test samples were prepared in steviol glycoside base solution and Vitaminwater® Zero revive fruit punch, respectively, containing (i) icariside F2 at 0.1 ppm; and (ii) icariside F2- containing plant extract at 100 ppm (prepared according to Example II).

Test samples with the addition of icariside F2 tasted less sweet intensity in linger. Test samples containing the plant extract tasted less green with less lingering aftertaste.

Example VI: Off-Taste Masking in Soy Protein Solution

Soy protein base solutions (prepared according to Example II) tasted slightly chalky and astringent with beany off-note and bitterness.

Test samples were prepared in soy protein base solutions containing (i) icariside F2 at 0.1 ppm; and (ii) icariside F2-containing plant extract at 100 ppm (prepared according to Example II). Test samples with the addition of icariside F2 tasted less astringent and less bitter. Test samples containing the plant extract tasted less chalky and less bitter.

Example VII: Off-taste Masking in Pea Protein Solution Pea protein base solutions (prepared according to Example II) displayed bitter, astringent and beany off-taste.

Test samples were prepared in pea protein base solutions containing (i) icariside F2 at 0.1 ppm; and (ii) icariside F2-containing plant extract at 100 ppm (prepared according to Example II).

Test samples with the addition of icariside F2 tasted less astringent and less bitter. Test samples containing the plant extract tasted less bitter with less pea aroma. Example VIII: Off-taste Masking in Preserve Base Solution

Preserve base (prepared according to Example II) displayed sour, astringent and bitter off-taste. Test samples were prepared in pea protein base solutions containing (i) icariside F2 at 0.01 ppm; and (ii) icariside F2-containing plant extract at 50 ppm (prepared according to Example II).

Test samples with the addition of icariside F2 or icariside F2-containing plant extract tasted less sour, astringent or bitter.

Example IX: Off-taste Masking in Other Applications

Citric base solutions (prepared according to Example II) displayed upfront and lingering sourness. Icariside F2-containing plant extract (100 ppm, prepared according to Example II) masked both upfront and lingering sourness.

Astringency base solution (prepared according to Example II) displayed astringency and bitterness. Icariside F2-containing plant extract (100, 200 or 250 ppm, prepared according to Example II) reduced both astringency and bitterness.

Alcoholic beverage base (prepared according to Example II) tasted astringent, sour and bitter. Icariside F2-containing plant extract (100 ppm, prepared according to Example II) reduced astringency, sourness and bitterness. Test samples of plant protein burgers containing plant extract (100 and 200 ppm, prepared according to Example II) showed reduced bitterness and beaniness with improved savory and salty notes.

Claims

WHAT IS CLAIMED IS:

1. A method of masking off-taste in a consumable comprising the step of adding an olfactory effective amount of a compound represented by Formula I:

Formula I wherein R¹ is H or -CH3, and R², R³ and R⁴ are each independently absent or selected from the group consisting of -OH and -OCH3; a salt thereof; or a mixture thereof to the consumable.

2. The method of claim 1, wherein the compound is 2-(benzyloxy)-6-(((3,4-dihydroxy-4- (hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol, a salt thereof, or a mixture thereof.

3. The method of claim 1, wherein the olfactory effective amount is from about 0.1 parts per billion to about 2000 parts per million.

4. The method of claim 1, wherein the olfactory effective amount is from about 1 part per billion to about 1000 parts per million.

5. The method of claim 1, wherein the olfactory effective amount is from about 10 parts per billion to about 500 parts per million.

6. The method of claim 1, wherein the consumable comprising a consumable acid selected from the group consisting of acetic acid, allantoic acid, A-ketoglutaric acid, ascorbic acid, aspartic acid, benzoic acid, cetostearic acid, citramalic acid, citric acid, formic acid, fumaric acid, galacturonic acid, glucoronic acid, glutamic acid, glyceric acid, glycolic acid, hydrochloric acid, isocitric acid, lactic acid, lactarimic acid, lactoisocitric acid, malic acid, oxalacetic acid, oxalic acid, phosphoric acid, pyroglutamic acid, pyrrolidinonecarboxylic acid, pyruvic acid, quinic acid, shikimic acid, succinic acid, sulphuric acid, tartaric acid, and a mixture thereof.

7. The method of claim 1 , wherein the consumable comprising a plant protein selected from the group consisting of soy protein, pea protein, wheat protein, oat protein, corn protein, peanut protein, silk protein, rice protein, almond protein, walnut protein, flaxseed protein, red bean protein, sunflower seed protein, mung bean protein, pumpkin seed protein, watermelon seed protein, highland barley protein, hemp protein, mushroom protein, shiitake protein, algae protein, tomato seed protein, rapeseed protein, potato protein, sacha inchi protein, fava protein, millet protein, lotus seed protein, black soybean protein, white kidney protein, and a mixture thereof.

8. The method of claim 1 , wherein the consumable comprising a steviol glycoside selected from the group consisting of stevioside, rubusoside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, a glycosylated derivative thereof, and a mixture thereof.

9. The method of claim 1 , wherein the consumable comprising a preservative selected from the group consisting of a benzoate, a sorbate, a propionate, a nitrite, a phosphate, and a mixture thereof.

10. A consumable comprising an olfactory effective amount of a compound represented by Formula I:

Formula I wherein R¹ is H or -CFh, and R², R³ and R⁴ are each independently absent or selected from the group consisting of -OH and -OCH3; a salt thereof; or a mixture thereof, wherein the consumable has off-taste.

11. The consumable of claim 10, wherein the compound is 2-(benzyloxy)-6-(((3,4-dihydroxy- 4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol.

12. The consumable of claim 10, wherein the olfactory effective amount is from about 0.1 parts per billion to about 2000 parts per million.

13. The consumable of claim 10, wherein the olfactory effective amount is from about 1 part per billion to about 1000 parts per million.

14. The consumable of claim 10, wherein the olfactory effective amount is from about 10 parts per billion to about 500 parts per million.

15. The consumable of claim 10 comprising a consumable acid selected from the group consisting of acetic acid, allantoic acid, A-ketoglutaric acid, ascorbic acid, aspartic acid, benzoic acid, cetostearic acid, citramalic acid, citric acid, formic acid, fumaric acid, galacturonic acid, glucoronic acid, glutamic acid, glyceric acid, glycolic acid, hydrochloric acid, isocitric acid, lactic acid, lactarimic acid, lactoisocitric acid, malic acid, oxalacetic acid, oxalic acid, phosphoric acid, pyroglutamic acid, pyrrolidinonecarboxylic acid, pyruvic acid, quinic acid, shikimic acid, succinic acid, sulphuric acid, tartaric acid, and a mixture thereof.

16. The consumable of claim 10 comprising a plant protein selected from the group consisting of soy protein, pea protein, wheat protein, oat protein, corn protein, peanut protein, silk protein, rice protein, almond protein, walnut protein, flaxseed protein, red bean protein, sunflower seed protein, mung bean protein, pumpkin seed protein, watermelon seed protein, highland barley protein, hemp protein, mushroom protein, shiitake protein, algae protein, tomato seed protein, rapeseed protein, potato protein, sacha inchi protein, fava protein, millet protein, lotus seed protein, black soybean protein, white kidney protein, and a mixture thereof.

17. The consumable of claim 10 comprising a steviol glycoside selected from the group consisting of stevioside, rubusoside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, a glycosylated derivative thereof, and a mixture thereof.

18. The consumable of claim 10 comprising a preservative selected from the group consisting of a benzoate, a sorbate, a propionate, a nitrite, a phosphate, and a mixture thereof.