Novel compositions for taste masking

Abstract

The use of lutein-alcohol adducts in providing off-taste masking effect in consumables is provided.

Description

[0001] IFF101100-WO-PCT

[0002] NOVEL COMPOSITIONS FOR TASTE MASKING

[0003] 5 Status of Related Application

[0004] This application claims priority to U.S. Provisional Application No. 63 / 699,269, filed September 26, 2024, the contents hereby incorporated by reference as if set forth in its entirety.

[0005] Field of the Invention

[0006] The present invention relates to novel compositions and methods for masking off-taste such as bitterness, astringency and / or lingering aftertaste that are associated with various components in consumables.

[0007] Background of the Invention

[0008] Some food components exhibit bitter, astringent and / or lingering aftertaste. These components include, for example, but not limited to, sugar substitutes including natural sugar substitutes such as steviol glycosides; artificial sweeteners such as aspartame, sucralose, neotame, acesulfame potassium and saccharin; carbohydrate sweeteners; plant or animal proteins; preservatives such as citric acid, sorbic acid, benzoic acid, sulfur dioxide, nitrate and nitrite; salts thereof or mixtures thereof. Such components can be inherently present in or added to the consumables. The off-taste has limited the applications of these components in food industry.

[0009] Thus, it is of particular need to develop taste modifiers that mask and / or reduce the off- taste associated with these components without affecting other desirable sensory traits.

[0010] IFF101100-WO-PCT Specification Summary of the Invention

[0011] The present invention has demonstrated that lutein-alcohol adducts suppress and reduce bitterness, astringency and / or lingering aftertaste that are associated with various food components such as natural sugar substitutes, artificial sweeteners, proteins, preservatives or 5 mixtures thereof.

[0012] In one embodiment, the present invention is directed to a method of masking an off-taste of bitterness, astringency and / or lingering aftertaste of a component in a consumable; wherein the component is selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof; and wherein the method comprises the step of adding to the consumable an olfactory effective amount of a lutein-alcohol adduct represented by formula I (lutein-R) set forth below:

[0013] ,

[0014]

[0015] wherein R is provided by an alcohol represented by R-OH, and wherein the alcohol is selected from the group consisting of ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, tert-butanol. methanol, 1-pentanol, 2-pentanol, 2-methyl-1-butanol, 2-methyl-2- butanol, 3-methyl-2-butanol, neopentyl alcohol, hexanols such as 2-methyl-1-pentanol, heptanols such as 1-heptanol, octanols such as 1-octanol, 2-octanol and 2-ethylhexanol, ethylene glycol, 1,3-propanediol, propylene glycol, butanediols such as 1,4-butanediol, glycerol, butanetriols such as 1,2,4-butanetriol, diethylene glycol, furfuryl alcohol, 2-(2-methoxyethoxy)ethanol, propylene glycol methyl ether and a mixture thereof.

[0016] In another embodiment, the present invention is directed to a method of masking an off- taste of bitterness, astringency and / or lingering aftertaste of a component in a consumable; wherein the component is selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof; and wherein the method 30 comprises the step of adding to the consumable an olfactory effective amount of lutein-propylene glycol adduct (lutein-PG).

[0017] Page 2 of 25 IFF101100-WO-PCT Specification In another embodiment, the present invention is directed to a composition comprising a component selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof; and an olfactory effective amount of a lutein-alcohol adduct of Formula I (lutein-R); wherein the component exhibits an off-taste of 5 bitterness, astringency and / or lingering aftertaste; and wherein lutein-R masks the off-taste of the component.

[0018] In another embodiment, the present invention is directed to a composition comprising a component selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof; and an olfactory effective amount of lutein-PG; wherein the component exhibits an off-taste of bitterness, astringency and / or lingering aftertaste; and wherein lutein-PG masks the off-taste of the component.

[0019] In another embodiment, the present invention is directed to a consumable containing a component selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof; and an olfactory effective amount of a lutein-alcohol adduct of Formula I (lutein-R); wherein the component exhibits an off-taste of bitterness, astringency and / or lingering aftertaste; and wherein lutein-R masks the off-taste of the component.

[0020] In another embodiment, the present invention is directed to a consumable containing a component selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof; and an olfactory effective amount of lutein-PG; wherein the component exhibits an off-taste of bitterness, astringency and / or lingering aftertaste; and wherein lutein-PG masks the off-taste of the component.

[0021] These and other embodiments of the present invention will be apparent by reading the following specification.

[0022] Page 3 of 25 IFF101100-WO-PCT Specification Detailed Description of the Invention

[0023] There has been increasing effort by food industry to reduce added sugar consumption in recent years by replacing refined sugar with sugar substitutes and artificial sweeteners. Sugar substitutes and artificial sweeteners are intense sweeteners and are many times sweeter than 5 regular sugar but provide fewer calories. Sugar substitutes include, for example, but not limited to, natural sugar substitutes such as steviol glycosides, thaumatin, Luo Han Guo and mono ammonium glycyrrhizinate (MAG). Steviol glycosides contain one or more intensely sweet glycosides derived from the leaves of a stevia (Stevia rebaudiana). Sugar substitutes have been widely used as noncaloric sweeteners to substitute sugar.

[0024] 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-O-β-D-glucoside, rubusoside, steviolbioside, stevioside, rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside G (Reb G), rebaudioside H (Reb H), rebaudioside I (Reb I), rebaudioside J (Reb J), rebaudioside K (Reb K), rebaudioside L (Reb L), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), dulcoside A, dulcoside B, isosteviol-19-O-β-D-glucoside, 15β- hydroxyrubusoside, 15-oxorubusoside, suavioside A, suavioside B, suavioside C1, suavioside C2, suavioside D1, suavioside D2, suavioside E, suavioside F, suavioside G, suavioside H, suavioside I, suavioside J, suavioside K, suavioside L, suavioside Q1, suavioside Q2, suavioside R1, suavioside R2, suavioside S1, suavioside S2, 9-hydroxysuavioside H, 9-hydroxysuavioside J, 15- oxosuavioside L, 15-oxo-16-epi-suavioside L, 16β-hydroxysuavioside L, 16α-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.

[0025] Artificial sweeteners may include, for example, but not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin and neohesperidin dihydrochalcone (NHDC).

[0026] However, when used in consumables, these non-sugar sweeteners leave astringency, licorice flavor and / or unpleasant lingering aftertaste such as lingering sweetness, bitterness and metallic aftertaste.

[0027] Page 4 of 25 IFF101100-WO-PCT Specification There is a further concern in food industry about lower levels of animal-based protein consumption. To address this concern, food industry has provided a variety of products enriched with proteins isolated from plants. A plant protein includes a plant amino acid, a plant peptide, a plant protein hydrolysate or a mixture thereof. However, plant proteins such as soy proteins and 5 pea proteins have bitter, 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 also increases processing costs.

[0028] In addition, preservatives are commonly used by food industry to prevent food from spoiling and changing in taste or appearance so to protect food quality and increase shelf life. However, preservatives such as citric acid, sorbic acid, benzoic acid, sulfur dioxide, nitrate, nitrite or a salt thereof may exhibit bitter and astringent off-taste.

[0029] The undesirable off-taste associated with various food components has limited their applications. Thus, it is of particular need to develop taste modifiers that mask and reduce these off-taste of these components in the consumables.

[0030] Lutein is found in high quantity in some foods especially in egg yolk and corn as well as in some colored fruits. vegetables and flowers including kiwi, grapes, spinach, orange juice, zucchini, kale, spinach, broccoli, peas, parsley and Marigold flowers (Tagetes erecta) (Perrone et al., Oxidative Medicine and Cellular Longevity (2016), 2016:5381540; Hu et al., Biotechnology Advances (2018), 36(1): 54-67; Alotaibi et al., Annals of Agricultural Sciences (2021), 66(2): 162-168). Lutein has been a subject of interest due to its promising nutrient. It is reported that the oxidized lutein acts as an antioxidant, thus protecting the retina (Khachik et al., Investigative Ophthalmology & Visual Science (1997), 38: 1802-1811; Roberts et al., Journal of Ophthalmology (2015), 2015: 687173).

[0031] However, there is no report on the preparation of lutein-alcohol adducts, let alone any flavor use associated with lutein-alcohol adducts. It has now been surprisingly discovered that lutein-alcohol adducts especially lutein-PG are particularly effective in masking bitterness, astringency and / or unpleasant lingering aftertaste caused by various food components such as natural sugar substitutes, artificial sweeteners, proteins, preservatives and mixtures thereof.

[0032] Page 5 of 25 IFF101100-WO-PCT Specification Lutein (CAS 127-40-2) is commercially available. It can also be prepared by known methods (See, for example, Lin et al., Bioresource Technology (2015), 184: 421-428). Lutein- alcohol adducts can be chemically prepared according to procedures known in the art, for example, as described in US5080817. Lutein-alcohol adducts can also be obtained through 5 alcohol solvolysis of lutein containing materials including foods, fruits, vegetables and flowers such as Marigold flowers. Common acid catalysts used in alcohol solvolysis include, for example, but not limited to, inorganic acids such as sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid and the like and organic acid such as citric acid, acetic acid, lactic acid, oxalic acid, malic acid, uric acid, formic acid, methanesulfonic acid and the like.

[0033] For example, lutein-alcohol adducts can be prepared via a general scheme depicted as follows:

[0034] ,

[0035]

[0036] wherein R is provided by an alcohol represented by R-OH, and wherein the alcohol is selected from the group consisting of ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, tert-butanol. methanol, 1-pentanol, 2-pentanol, 2-methyl-1-butanol, 2-methyl-2- butanol, 3-methyl-2-butanol, neopentyl alcohol, hexanols such as 2-methyl-1-pentanol, heptanols such as 1-heptanol, octanols such as 1-octanol, 2-octanol and 2-ethylhexanol, ethylene glycol, 1,3-propanediol, propylene glycol, butanediols such as 1,4-butanediol, glycerol, butanetriols such as 1,2,4-butanetriol, diethylene glycol, furfuryl alcohol, 2-(2-methoxyethoxy)ethanol, propylene glycol methyl ether and a mixture thereof.

[0037] Page 6 of 25 IFF101100-WO-PCT Specification The terms “off-taste,” “aftertaste” and “after taste” are the same and are understood to mean bitterness, astringency, licorice flavor, unpleasant lingering aftertaste such as lingering sweetness, bitterness or metallic aftertaste and / or beany and earthy taste associated with a food component as described herein.

[0038] 5

[0039] The term “mask” or “masking” is understood to mean covering, disguising and / or obscuring a bitter, astringent and / or off-taste of a component in a consumable by adding to the consumable an olfactory effective amount of a lutein-R, in particular, lutein-PG, wherein the component remains unchanged, but its undesirable taste is less or not perceived by a human consuming the consumable. The taste or flavor profile of the consumable improves through an addition to the consumable of lutein-R, in particular, lutein-PG, compared to the taste or flavor profile of a comparative consumable in the absence of lutein-R, in particular, lutein-PG.

[0040] The term “olfactory effective amount” is understood to mean the amount of a lutein- alcohol adduct used in a consumable to mask bitterness, astringency and / or lingering aftertaste associated with a component contained in the consumable, wherein the component is a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof or a mixture thereof.

[0041] 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 a lutein-alcohol adduct that provides the desired degree of bitterness, astringency and / or lingering aftertaste masking effect without exhibiting off-taste can be used. In certain embodiments, the olfactory effective amount ranges from about 0.1 parts per billion to about 500 parts per million by weight of a consumable, more preferably from about 1 part per billion to about 100 parts per million by weight of a consumable, even more preferably from about 10 parts per billion to about 50 parts per million by weight of a consumable. The term “ppb” is understood to mean part per billion by weight. The term “ppm” is understood to mean part per million by weight.

[0042] A consumable includes, for example, a food product (e.g., a beverage), a sweetener such 30 as a natural sweetener or an artificial sweetener, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product. The consumable may further contain a flavoring.

[0043] Page 7 of 25 IFF101100-WO-PCT Specification A natural sweetener includes, for example, but not limited to, sucrose, fructose, glucose, high fructose corn syrup, Stevia rebaudiana compositions including pure components of Reb A, stevioside, and Reb D, xylose, arabinose, or rhamnose, as well as sugar alcohols such as erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof. An artificial sweetener 5 includes, for example, but not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.

[0044] A flavoring is a preparation that provides a consumable with a particular taste and / or smell. A flavoring with modifying properties is a subset of the flavoring. It is added to the consumable to reduce off-notes and / or improve overall profile. The flavorings with modifying properties of the present invention include, for example, but not limited to, a stevia composition including stevioside, steviolbioside Reb A, Reb B, Reb C, Reb D, Reb E, Reb F, dulcoside A, dulcoside B, rubusoside, alpha-glucosyl stevia, fructosyl stevia, galactosyl stevia, beta-glucosyl stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, 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. In one embodiment, the flavorings with modifying properties of the present invention include Reb A, Reb C, rubusoside, Reb D, mogroside V, Luo Han Guo, monatin acid, a salt thereof, a glycosylated derivative thereof and a combination thereof. The flavorings with modifying properties of the present invention exhibit weak intrinsic sweetness. Some other flavorings of the present invention include, for example, but not limited to, curculin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobtain, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, cyclocarioside I and a combination thereof.

[0045] 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, 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- Page 8 of 25 IFF101100-WO-PCT Specification 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 5 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. Consumables further include condiments such as herbs, spices and seasonings, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners.

[0046] 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, doxlamine succinate, brompheniramine maleate, phenyltoloxamine citrate, chlorcyclizine hydrochloride, pheniramine maleate, or phenindamine tartrate, a decongestant, e.g., phenylpropanolamine hydrochloride, phenylephrine hydrochloride,

[0047] Page 9 of 25 IFF101100-WO-PCT Specification 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., 5 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.

[0048] 30

[0049] Page 10 of 25 IFF101100-WO-PCT Specification The term “sweetness” or “sweetness intensity” is understood to mean the relative strength of sweet sensation as observed or experienced by an individual, e.g., a human, or a degree or amount of sweetness detected by a taster, for example on the scale from 0 (none) to 8 (very strong) used in sensory evaluations according to the procedure described in American Society for 5 Testing Materials, Special Technical Publication-434: “Manual on Sensory Testing Methods,” ASTM International, West Conshohocken, PA. (1996). In certain embodiments, modification of sweet perception may also affect the perception of other basic tastes. For example, increasing sweetness may decrease the perception of sourness, bitterness and salty (Mojet et al., Chemical Senses (2004), 29: 671-681). Thus, sweet modulation may reduce, mask and balance other flavors. A balanced flavor profile can be achieved through modulating basic tastes.

[0050] The term “sweet mouthfeel” is understood to mean syrupy and / or sugar-like mouthfeel. Sweet mouthfeel provides perception of syrupiness that is viscous or thick, which resembles mouthfeel provided by high concentrations of sugar.

[0051] Additional materials can also be used in conjunction with lutein-R compounds of the present invention to encapsulate and / or deliver the bitterness, astringency, licorice flavor and / or unpleasant lingering aftertaste 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.

[0052] The invention is described in greater detail by the following non-limiting examples. Materials were purchased from Aldrich Chemical Company unless noted otherwise.

[0053] Page 11 of 25 IFF101100-WO-PCT Specification Example I: Preparation of Lutein-PG

[0054]

[0055] 5 Lutein (3.2 g) was added to a 1-L round bottom flask. Phosphoric acid (85%, 1.85 g) was then added followed by propylene glycol (PG) (440 g). The reaction mixture was agitated at 95 °C for about 7 hours and then cooled down to room temperature. Preparative HPLC was performed with a Zorbax SB-Aq C18 column (Agilent Technologies, Inc.) to isolate lutein-PG (3.0 g), whose structure was elucidated by analyzing high resolution LCMS, UV absorbance and 10 proton and carbon NMR spectra.

[0056] 1H NMR (600 MHz, ACETONE-d6) δ: 6.70-6.79 (m, 4H), 6.18-6.46 (m, 9H), 5.61-5.64 (m, 1H), 5.55 (dd, J=15.5 Hz, 9.9 Hz, 1H), 3.88-3.96 (m, 2H), 3.37 (d, J = 5.8 Hz, 2H), 1.99-2.02 (m, 9H), 1.95 (s, 3H), 2.45 (d, J=9.0 Hz, 2H), 2.31-2.36 (m, 2H), 1.76-1.83 (m, 2H), 1.74 (s, 3H), 1.63 (s, 15 3H), 1.41-1.46 (m, 2H), 1.10 (d, J=6.1 Hz, 3H), 1.09 (s, 3H), 1.07(s, 3H), 1.00(s, 3H), 0.87(s, 3H)

[0057] Page 12 of 25 IFF101100-WO-PCT Specification Example II: Preparation of Lutein and Lutein-PG Solutions and Testing Procedure

[0058] Preparation of Lutein and Lutein-PG Water Solutions: Water solutions of lutein and lutein-PG (prepared as above in Example I) were prepared and used in the following examples. Water 5 solutions of lutein and lutein-PG at concentrations ranging from 2 ppb to 5 ppm were each evaluated for innate taste and smell. Both lutein and lutein-PG displayed paint-like, floral and slight honey notes.

[0059] Testing Procedure: The masking effect on bitterness, astringency and / or lingering aftertaste 10 associated with various food components was evaluated by a group of 26 trained panelist. Each provided a rank of masking intensity using the intensity scales of 0 to 5, where 0 represents “no masking effect,” 1 represents “minimal masking intensity” and 5 represents “the most masking intensity.” The average of the reported making intensity is presented in the following examples.

[0060] 15

[0061] Page 13 of 25 IFF101100-WO-PCT Specification Example III: Masking Effect on Reb A

[0062] A Reb A base solution (200 ppm) was prepared in water. The base solution exhibited astringency, licorice flavor, lingering sweetness and bitterness and metallic aftertaste. The flavor profile of the Reb A solution with added lutein-PG and lutein was further evaluated and is 5 reported in the following:

[0063]

[0064] In contrast, the flavor profile of Reb A solutions with added lutein at concentrations of 0.002, 0.02, 0.1, 0.144, 1, 10, 20 and 40 ppm was shown to be similar to that of the Reb A base 10 solution. Thus, lutein has no masking effect on Reb A off-taste.

[0065] Page 14 of 25 IFF101100-WO-PCT Specification Example IV: Masking Effect on Tropicana® Zero Sugar Classic Lemonade Tropicana®Zero Sugar Classic Lemonade (“Tropicana®lemonade”) contains steviol glycosides and stevia leaf extract, and exhibits astringency, licorice flavor, lingering sweetness and bitterness and metallic aftertaste. The flavor profile of Tropicana®lemonade with added 5 lutein-PG and lutein was further evaluated and is reported in the following:

[0066]

[0067] In contrast, the flavor profile of Tropicana®lemonade solutions with added lutein at concentrations of 0.002, 0.02, 0.1, 0.5, 1, 5, 10 or 20 ppm was shown to be similar to that of the 10 Tropicana®lemonade base solution. Thus, lutein has no masking effect on Tropicana®lemonade off-taste.

[0068] Page 15 of 25 IFF101100-WO-PCT Specification Example V: Masking Effect on Additional Sweeteners

[0069] The masking effect of lutein-PG on additional sweeteners was evaluated. Base solutions of additional sweeteners in water or additional sweetener-containing base consumables were prepared and evaluated as controls. Corresponding samples with added lutein-PG and lutein 5 were further prepared and evaluated. The results are reported as follows:

[0070] Masking Effect on Reb C

[0071]

[0072] 10 Masking Effect on Reb M

[0073]

[0074] Masking Effect on Oikos®Triple Zero Vanilla

[0075] Oikos®Triple Zero Vanilla (“Oikos®Vanilla”) contains stevia leaf extract and exhibits 15 astringent, bitter and lingering aftertaste that is associated with stevia leaf extract.

[0076]

[0077] Page 16 of 25 IFF101100-WO-PCT Specification Masking Effect on Thaumatin

[0078]

[0079] Masking Effect on Luo Han Guo

[0080]

[0081] 5

[0082] Masking Effect on Mono Ammonium Glycyrrhizinate (MAG)

[0083]

[0084] 10 Masking Effect on Aspartame

[0085]

[0086] Page 17 of 25 IFF101100-WO-PCT Specification Masking Effect on Sucralose, Acesulfame potassium (Ace-K) and Citric Acid Mixture Sucralose, Ace-K and citric acid mixture can be used to provide sweetness. A water solution of sucralose (0.06 ppm), Ace-K (0.04 ppm) and citric acid (0.5 ppm) (“Mixture”) was prepared as the base solution.

[0087]

[0088] 5

[0089] Masking Effect on Neohesperidin Dihydrochalcone (NHDC)

[0090]

[0091] 10 Masking Effect on Citric Acid

[0092]

[0093] Page 18 of 25 IFF101100-WO-PCT Specification Masking Effect on Pea Protein

[0094] A solution of TRUPRO®pea protein (Solae LLC) in water (5%) was prepared as the base solution.

[0095]

[0096] 5

[0097] Masking Effect on Soy Protein

[0098] A solution of SUPRO®soy protein (Solae LLC) in water (5%) was prepared as the base solution.

[0099]

[0100] 10

[0101] Page 19 of 25

Claims

IFF101100-WO-PCT Specification WHAT IS CLAIMED IS:

1. A method of masking an off-taste of a component in a consumable comprising the step of adding to the consumable an olfactory effective amount of a lutein-alcohol adduct;5 wherein the off-taste of the component is bitterness, astringency, licorice flavor and / or unpleasant lingering aftertaste; andwherein the lutein-alcohol adduct is represented by formula I set forth below:,wherein R is provided by an alcohol represented by R-OH; and wherein the alcohol is selected from the group consisting of ethanol, 1-propanol, isopropanol, 1- butanol, 2-butanol, isobutanol, tert-butanol. methanol, 1-pentanol, 2-pentanol, 2-methyl- 1-butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, neopentyl alcohol, hexanols such as 2-methyl-1-pentanol, heptanols such as 1-heptanol, octanols such as 1-octanol, 2-octanol and 2-ethylhexanol, ethylene glycol, 1,3-propanediol, propylene glycol, butanediols such as 1,4-butanediol, glycerol, butanetriols such as 1,2,4-butanetriol, diethylene glycol, furfuryl alcohol, 2-(2-methoxyethoxy)ethanol, propylene glycol methyl ether and a mixture thereof.

2. The method of claim 1, wherein the lutein-alcohol adduct is lutein-propylene glycol adduct.

3. The method of claim 1, wherein the component is selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof.

4. The method of claim 1, wherein the olfactory effective amount is from about 0.1 parts 30 per billion to about 500 parts per million by weight of the consumable.Page 20 of 25IFF101100-WO-PCT Specification 5. The method of claim 1, wherein the olfactory effective amount is from about 1 part per billion to about 100 parts per million by weight of the consumable.

6. The method of claim 3, wherein the sugar substitute is selected from the group consisting 5 of a steviol glycoside, thaumatin, Luo Han Guo, mono ammonium glycyrrhizinate, aspartame, sucralose, neotame, acesulfame potassium, saccharin, neohesperidin dihydrochalcone, a salt thereof and a mixture thereof.

7. The method of claim 3, wherein the protein is a plant protein selected from the group consisting of a pea protein, a soy protein and a mixture thereof.

8. A composition comprising a component and an olfactory effective amount of a lutein- alcohol adduct;wherein the component exhibits an off-taste of bitterness, astringency, licorice flavor and / or unpleasant lingering aftertaste;wherein the lutein-alcohol adduct is represented by formula I set forth below:,wherein R is provided by an alcohol represented by R-OH; and wherein the alcohol is selected from the group consisting of ethanol, 1-propanol, isopropanol, 1- butanol, 2-butanol, isobutanol, tert-butanol. methanol, 1-pentanol, 2-pentanol, 2-methyl- 1-butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, neopentyl alcohol, hexanols such as 2-methyl-1-pentanol, heptanols such as 1-heptanol, octanols such as 1-octanol, 2-octanol and 2-ethylhexanol, ethylene glycol, 1,3-propanediol, propylene glycol, butanediols such as 1,4-butanediol, glycerol, butanetriols such as 1,2,4-butanetriol, diethylene glycol, furfuryl alcohol, 2-(2-methoxyethoxy)ethanol, propylene glycol methyl ether and a mixture thereof; and30 wherein the lutein-alcohol adduct masks the off-taste of the component.Page 21 of 25IFF101100-WO-PCT Specification 9. The composition of claim 8, wherein the lutein-alcohol adduct is lutein-propylene glycol adduct.

10. The composition of claim 8, wherein the component is selected from the group consisting 5 of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof.

11. The composition of claim 8, wherein the olfactory effective amount is from about 0.1 parts per billion to about 500 parts per million by weight of the composition.

12. The composition of claim 8, wherein the olfactory effective amount is from about 1 part per billion to about 100 parts per million by weight of the composition.

13. The composition of claim 10, wherein the sugar substitute is selected from the group consisting of a steviol glycoside, thaumatin, Luo Han Guo, mono ammonium glycyrrhizinate, aspartame, sucralose, neotame, acesulfame potassium, saccharin, neohesperidin dihydrochalcone, a salt thereof and a mixture thereof.

14. The composition of claim 10, wherein the protein is a plant protein selected from the group consisting of a pea protein, a soy protein and a mixture thereof.Page 22 of 25IFF101100-WO-PCT Specification 15. A consumable comprising a component and an olfactory effective amount of a lutein- alcohol adduct;wherein the component exhibits an off-taste of bitterness, astringency, licorice flavor and / or unpleasant lingering aftertaste;5 wherein the lutein-alcohol adduct is represented by formula I set forth below:,wherein R is provided by an alcohol represented by R-OH; and wherein the alcohol is selected from the group consisting of ethanol, 1-propanol, isopropanol, 1- butanol, 2-butanol, isobutanol, tert-butanol. methanol, 1-pentanol, 2-pentanol, 2-methyl- 1-butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, neopentyl alcohol, hexanols such as 2-methyl-1-pentanol, heptanols such as 1-heptanol, octanols such as 1-octanol, 2-octanol and 2-ethylhexanol, ethylene glycol, 1,3-propanediol, propylene glycol, butanediols such as 1,4-butanediol, glycerol, butanetriols such as 1,2,4-butanetriol, diethylene glycol, furfuryl alcohol, 2-(2-methoxyethoxy)ethanol, propylene glycol methyl ether and a mixture thereof; and whereinthe consumable is selected from the group consisting of a food product, a sweetener, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product.

16. The consumable of claim 15, wherein the lutein-alcohol adduct is lutein-propylene glycol adduct.

17. The consumable of claim 15, wherein the component is selected from the group consisting of a sugar substitute, an artificial sweetener, a protein, a preservative, a salt thereof and a mixture thereof.30 18. The consumable of claim 15, wherein the olfactory effective amount is from about 0.1 parts per billion to about 500 parts per million by weight of the consumable.Page 23 of 25IFF101100-WO-PCT Specification 19. The consumable of claim 17, wherein the sugar substitute is selected from the group consisting of a steviol glycoside, thaumatin, Luo Han Guo, mono ammonium glycyrrhizinate, aspartame, sucralose, neotame, acesulfame potassium, saccharin, neohesperidin dihydrochalcone, a salt thereof and a mixture thereof.

520. The consumable of claim 17, wherein the protein is a plant protein selected from the group consisting of a pea protein, a soy protein and a mixture thereof.10Page 24 of 25

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