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WO2025188525A1 - Nouvelles compositions pour la modulation du goût - Google Patents

Nouvelles compositions pour la modulation du goût

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Publication number
WO2025188525A1
WO2025188525A1 PCT/US2025/017463 US2025017463W WO2025188525A1 WO 2025188525 A1 WO2025188525 A1 WO 2025188525A1 US 2025017463 W US2025017463 W US 2025017463W WO 2025188525 A1 WO2025188525 A1 WO 2025188525A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
rebaudioside
sweetness
dihydroxy
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/017463
Other languages
English (en)
Other versions
WO2025188525A8 (fr
Inventor
Xiao-Qing Tang
Diana KLASER CHENG
Amarendar MADDIRALA
Michael G. Monteleone
Cor NIEDEVELD
Xiangyun Wang
Melanie CROCE
Negin SHARAFBAFI
Ajay Pratap Singh
Peter Bechmann
Pei-Fen Wu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Publication of WO2025188525A1 publication Critical patent/WO2025188525A1/fr
Publication of WO2025188525A8 publication Critical patent/WO2025188525A8/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/39—Addition of sweetness inhibitors
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • sweetness modulators have become valuable tools, which reduce the use of sugar and/or sweetness modifiers, in achieving the desired sweetness intensity and mouthfeel with reduced off-taste. Sweetness modulators have been described in the prior art.
  • WO 2013/143822 teaches the use of adenosine as sweetness modulator for certain sugars; EP 2606747 describes the use of deoxycholic acid or a derivative thereof for modulating the sweetness of consumables; WO 2013/077668 describes the sweetness modulating effect of a glycan or glycopeptide derived from soy sauce; WO 2012/107203 teaches the use of nobiletin or a derivative or a hydrate thereof as a sweetener or sweetness modulator; WO 2009/023975 describes the use of iso-mogroside V as a sweetener and sweetness modulator; US 2008/0242740 teaches aroma compositions of alkamides with hesperetin and/or 4-hydroxydihydrochalcones for modulating sweet sensory impressions; and WO 2007/014879 and WO 2007/107596 respectively teach the use of hesperetin and 4- hydroxydihydrochalcones for modulating the sweet taste of a sweet-tasting substance or
  • This invention provides a method of modulating sweetness perception, improving sweetness mouthfeel and/or masking off-taste of a sweetness modifier by adding an olfactory effective amount of a compound represented by Formula I set forth below to the sweetness modifier:
  • Formula I wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently absent or selected from the group consisting of H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 heteroalkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 heterocycloalkyl, C 1 -C 10 alkoxy, C 1 -C 10 alkylthio, C 1 -C 10 acyl, C 1 -C 10 acyloxy, aryl, aryloxy, arylthio
  • IFF10080-WO-PCT[2] Specifically, the above compound of Formula I is represented by Formula II set forth below: are each independently absent or selected from the group consisting of H, C 1 -C 4 alkyl, a sugar moiety and OR’; wherein R’ is selected from the group consisting of H, C 1 -C 4 alkyl and a sugar moiety; and wherein the dashed line represents an optional carbon-carbon bond, with the proviso that the carbon valency of 4 is satisfied.
  • R 1’ , R 2’ , R 3’ , R 4’ , R 5’ , R 6’ , R 7’ , R 8’ , R 9’ and R 10’ are defined as above; and wherein the dashed line represents an optional carbon-carbon bond, with the proviso that the carbon valency of 4 is satisfied.
  • the present invention is directed to a method of modulating sweetness perception, improving sweetness mouthfeel and/or masking off-taste of a sweetness modifier comprising the step of adding an olfactory effective amount of the compound provided above to the sweetness modifier.
  • the present invention is directed to a composition comprising a sweetness modifier and an olfactory effective amount of the compound provided above.
  • the present invention is directed to a consumable comprising a sweetness modifier and an olfactory effective amount of the compound provided above.
  • IFF10080-WO-PCT[2] Detailed Description of the Invention
  • the compounds of the present invention contain chiral centers, thereby providing a number of isomers. It is intended herein that the compounds described herein include individual isomers as well isomeric mixtures.
  • Some of the compounds of the present invention may be represented by the following structures: IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2] IFF10080-WO-PCT[2]
  • the compounds of the present invention can be synthesized or extracted from a plant.
  • Formula III compounds may be prepared via general schemes depicted as follows: IFF10080-WO-PCT[2] wherein R 1’ , R 2’ , R 3’ , R 4’ , R 5’ , R 6’ , R 7’ , R 8’ , R 9’ , R 10’ and the dashed lines are defined as above; and wherein THF represents tetrahydrofuran ((CH2)4O), Pd/C represents palladium on carbon, i-PrOH represents propan-2-ol ((CH 3 ) 2 CHOH) and DMF represents dimethylformamide ((CH3)2NCH).
  • Compounds of Formula IV can also be prepared according to known methods (e.g., Honda, et al.
  • Compounds of the present invention may also be obtainable from plant genera such as, for example, but not limited to, Agave, Bellevalia, Drimia, Eucomis, Leopoldia, Massonia, Merwilla, Muscari, Resnova, Rhodocodon, and Scilla.
  • compounds of the present invention are provided as botanical extract of a species such as, for example, but not limited to, Agave sisalana, Bellevalia eigii, Bellevalia flexuosa, Eucomis montana, Leopoldia comosa (Muscari comosum), Massonia pustulata, Massonia bifolia, Merwilla plumbea, Muscari neglectum, Muscari armeniacum, Muscari botryoides, Resnova humifusa, Rhodocodon calcicole, Rhodocodon campanulatus, Scilla luciliae, Scilla nervosa, Scilla scilloides, Scilla natalensis or Scilla zebrina.
  • a species such as, for example, but not limited to, Agave sisalana, Bellevalia eigii, Bellevalia flexuosa, Eucomis montana, Leopoldia comosa (Mus
  • the extract is enriched for the compounds of the present invention to achieve a content of about 0.01% and greater.
  • the botanical extract contains the compounds of the present invention from about 0.05 to about 95%, from about 0.1 to about 50% or from about 0.2 to about 10%. Unless otherwise specified, percentages (% s) are by weight.
  • KR2018064130 teaches the use of similar compounds in the treatment of ischemic brain damage IFF10080-WO-PCT[2] and multiple sclerosis.
  • JP2005323504A also teaches the use of similar compounds in the improvement of lipid metabolism and the treatment of diabetes.
  • nothing in the prior art teaches the modulation of sweetness perception, improvement of sweetness mouthfeel and/or off-taste masking effect of any of these compounds.
  • compounds of the present invention are effective in modulating sweetness perception, improving sweetness mouthfeel and/or masking off-taste of a sweetness modifier such as bitterness, the lingering aftertaste and astringency.
  • 5,7-dihydroxy-3-(3- hydroxy-4-methoxybenzyl)chroman-4-one contains (3R)-2,3-dihydro-5,7-dihydroxy-3-[(3- hydroxy-4-methoxyphenyl)methyl]-4H-1-benzopyran-4-one and (3S)-2,3-dihydro-5,7-dihydroxy- 3-[(3-hydroxy-4-methoxyphenyl)methyl]-4H-1-benzopyran-4-one having a weight ratio of 1 or greater.
  • sugar moiety refers to a natural or a modified sugar group that can be linear or cyclic.
  • the sugar moiety of the present invention includes, for example, but not limited to, a monosaccharide, a disaccharide or a derivative thereof.
  • the sugar moiety of the present invention includes, for example, but not limited to, glucose, fructose, sucrose, galacturonic acid or a derivative thereof.
  • a preferred sugar moiety of the present invention is glucose.
  • the term “a” or “an” is understood to mean one or more.
  • the term “a compound” is understood to mean one or more of the compounds represented by Formula I, Formula II, Formula III, Formula IV or a mixture thereof as described herein.
  • a natural sweetener includes, for example, but not limited to, sucrose, fructose, glucose, high fructose corn syrup, steviol glycosides derived from the leaves of a stevia (Stevia rebaudiana), xylose, arabinose or rhamnose, as well as sugar alcohols such as erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.
  • An artificial sweetener includes, for example, but not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin, neohesperidin dihydrochalcone (NHDC) and a combination thereof.
  • 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, steviol glycosides, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, mono ammonium glycyrrhizinate (MAG), a salt thereof, a glycosylated derivative thereof and a combination thereof.
  • 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- ⁇ -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- ⁇ -D-glucoside, 15 ⁇
  • 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.
  • 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.
  • a sweetness modifier refers to a sweetener including a natural sweetener and an artificial sweetener or a flavoring with modifying properties set forth in the above.
  • sweetness or “sweetness intensity” refers to 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 Testing Materials, Special Technical Publication-434: “Manual on Sensory Testing Methods,” ASTM International, West Conshohocken, PA. (1996).
  • a sweetness modulator refers to a preparation that modulates or intensifies the perception of the sweet taste of a sweetness modifier.
  • a sweetness modulator provides sweetness modulation without providing any noticeable sweetness by itself at its general use levels.
  • a compound of the present invention is used as a sweetness modulator.
  • 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.
  • olfactory effective amount is understood to mean the amount of a compound of the present invention used in a combination with a sweetness modifier, wherein the compound of the present invention modulates or intensifies the sweetness perception, improves the sweetness mouthfeel and/or masks the off-taste of the sweetness modifier. Its 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 sweetness modulator that provides the desired degree of sweetness modulation without exhibiting off-taste can be used.
  • the olfactory effective amount of a sweetness modulator containing a compound of the present invention ranges from about 1 ppb to about 500 ppm, preferably from about 100 ppb to about 200 ppm and more preferably form about 1 to about 50 ppm.
  • a consumable includes, for example, a food product (e.g., a beverage), a sweetener such as a natural sweetener or an artificial sweetener, a flavoring, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product.
  • the consumable may further contain a flavoring.
  • 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 yogurt, 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, chocolates, chewing gums, mints, creams, pies and breads.
  • 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.
  • Consumables further include condiments such as herbs, spices and seasonings, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners.
  • condiments such as herbs, spices and seasonings, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners.
  • a preferred consumable includes carbonated beverages, yogurt, plant-based foods and beverages and savory products.
  • a consumable also includes a vegan mayonnaise, a vegan pasta, a vegan egg, a vegan custard, a vegan soup, a vegan sauce, a vegan baked goods, a vegan dairy product (e.g., a vegan yogurt, a vegan ice cream and a vegan cheese), a vegan meat, a vegetarian mayonnaise, a vegetarian pasta, a vegetarian egg, a vegetarian custard, a vegetarian soup, a vegetarian sauce, a vegetarian baked goods, a vegetarian dairy product (e.g., a vegetarian yogurt, a vegetarian ice cream and a vegetarian cheese), a vegetarian meat and alike.
  • a vegan dairy product e.g., a vegan yogurt, a vegetarian ice cream and a vegetarian cheese
  • 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 a compound of the present invention, one or more pharmaceutically acceptable excipients and one or more active agents that exert a biological effect other than sweetness modulation.
  • 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.
  • such an active agent includes a bronchodilator, an anorexiant, an antihistamine, a nutritional supplement, a laxative, an analgesic, IFF10080-WO-PCT[2] 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.
  • 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, 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
  • 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.
  • 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.
  • 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, IFF10080-WO-PCT[2] 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.
  • the dental hygienic composition includes one natural sweetener.
  • the dental hygienic composition includes more than one natural sweetener.
  • 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 Beewax Lip Balm.
  • the present invention also provides methods for modulating the sweetness of a flavoring with modifying properties and decreasing its use level in a consumable by incorporating a compound of the present invention.
  • the invention provides a consumable containing an olfactory effective amount of a compound of the present invention and a flavoring with modifying properties in a reduced amount in order to achieve the same level of sweetness when the flavoring with modifying properties is used alone in a traditional amount.
  • the amount of flavoring with modifying properties used in a consumable can be reduced by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 95%, from about 60% to about 99% or from about 20% to about 50%.
  • a compound of the present invention can be used in a consumable as a sweetness modulator, which retains a desired sweetness but contains lower amounts of a natural sweetener or an artificial sweetener.
  • an improved carbonated soft drink can be produced with the same sweetness as the known carbonated soft drink but with lower sugar content by adding a compound of the present invention.
  • Additional materials can also be used in conjunction with a compound of the present invention to encapsulate and/or deliver the 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.
  • 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.
  • IFF10080-WO-PCT[2] The following are provided as specific embodiments of the present invention. Other modifications of this invention will be readily apparent to those skilled in the art. Such modifications are understood to be within the scope of this invention. Materials were purchased from Aldrich Chemical Company unless noted otherwise.
  • ppm is understood to stand for parts per million
  • L is understood to be liter
  • mL is understood to be milliliter
  • g is understood to be gram
  • Kg is understood to be kilogram
  • mol is understood to be mole
  • mmol is understood to be millimole
  • psi is understood to be pound-force per square inch
  • mmHg millimeters (mm) of mercury (Hg).
  • IFF as used in the examples is understood to mean International Flavors & Fragrances Inc., New York, NY, USA.
  • reaction mixture was stirred at room temperature for 30 minutes followed by addition of methanesulfonyl chloride (20.35 mL, 263.0 mmol) as a solution in anhydrous DMF (40 mL) at 50-55°C.
  • methanesulfonyl chloride 20.35 mL, 263.0 mmol
  • the obtained reaction mixture was stirred at the same temperature for another 2 hours until the reaction was complete as monitored by TLC.
  • the reaction mixture was then cooled to room temperature and poured into ice water. The resultant suspension was stirred for 30 minutes.
  • reaction mixture was then heated to 40°C and stirred under hydrogen (40 psi) until the reaction was complete as monitored by LC-MS.
  • the reaction mixture was cooled to room temperature, the solid residue was removed by filtration through a pad of Celite ® and washed once with isopropanol (10%).
  • the filtrate was washed with water (30 mL) and concentrated under reduced pressure. Water (30 mL) was added and the pH was adjusted to 6.5 with HCl (3.0 M). The obtained solution was stirred at room temperature for 1 hour.
  • the precipitate was then collected by filtration, washed with water, and dried under vacuum in an oven at 60°C overnight to provide 3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6- trihydroxyphenyl)propan-1-one as an off-white solid (1.5 g).
  • the filtrate was concentrated under reduced pressure.
  • the resultant residue was purified by HPLC and further dried under vacuum in an oven at 60 °C overnight to provide 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4- one as a white solid (0.77 g).
  • reaction mixture was then warmed up to room temperature and stirred under nitrogen until the reaction was complete as monitored by TLC (2:3 ethyl acetate/hexanes).
  • the reaction mixture was quenched with cold water and stirred at room temperature for 5 minutes.
  • the organic layer was separated, washed with brine, dried over magnesium sulfate (MgSO 4 ) and filtered. After evaporation of the solvent, the residue was purified by HPLC with water/acetonitrile eluent system. The obtained fractions were combined, frozen dried and further dried under vacuum in an oven at 55°C overnight to provide 3- (3,4-dihydroxybenzyl)-5,7-dihydroxychroman-4-one as a brown solid (100 mg).
  • Extract of Scilla scilloides bulbs was prepared in water and/or ethanol according to a method known to a skilled person (WO2020/118002). Following compounds were further isolated. 5,7-Dihydroxy-3-(4-hydroxybenzyl)chroman-4-one (Compound No. 2), 5,7- dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one (Compound No. 4), 3-(4- hydroxybenzyl)-5,7-dihydroxy-6-methoxychroman-4-one (Compound No.
  • (3S)-2,3-Dihydro- 5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-4H-1-benzopyran-4-one (Compound No. 6) is isolated from, for example, but not limited to, Rhodocodon calcicole, Rhodocodon campanulatus and Rhodocodon aff. Intermedius. In addition, 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one (Compound No.
  • a weight ratio of (3R)-2,3-dihydro-5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-4H- 1-benzopyran-4-one and (3S)-2,3-dihydro-5,7-dihydroxy-3-[(3-hydroxy-4- methoxyphenyl)methyl]-4H-1-benzopyran-4-one of 1:9 to 9:1 is required for 5,7-dihydroxy-3-(3- hydroxy-4-methoxybenzyl)chroman-4-one to provide desired taste improvement without off-notes.
  • (3R)-2,3-dihydro-5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-4H-1- benzopyran-4-one and (3S)-2,3-dihydro-5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]- 4H-1-benzopyran-4-one have a weight ratio of 1 or greater.
  • EXAMPLE VIII MODULATION OF SUCROSE SWEETNESS Water solutions of 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one (“Compound No. 4”) (obtained in EXAMPLE III) at 0,05, 1, 5, 15 and 30 ppm were all devoid of taste or smell. Sweetness intensity was provided using a scale of 0 to 10, where 0 represents the sweetness intensity of the base controls, 1 represents “minimally enhanced sweetness intensity” and 10 represents “the most enhanced sweetness intensity.” A sucrose solution (6%) was prepared in water and used as the sucrose base control.
  • 5,7- Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one was evaluated in the sucrose base control solution at 0.05, 1, 5, 15 and 30 ppm, respectively.
  • the average of the reported sweetness intensity is presented in the following examples.
  • Sweet flavors of the sucrose solution with added 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one are reported in the following: 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one provided enhanced sweetness perception in sucrose solution.
  • 5,7-Dihydroxy-3-(3-hydroxy-4- methoxybenzyl)chroman-4-one exhibited particularly superior effect at 0.05 ppm or higher.
  • a Dannon Non-Fat Plain Yogurt with added sucrose was prepared based on Applicants’ proprietary formulation.
  • An addition of 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman- 4-one (10 ppm) enhanced the perception of sweetness and sugary mouthfeel, and improved creaminess in the yogurt.
  • a sweet orange flavor carbonated drink was prepared based on Applicants’ proprietary formulations.
  • An addition of 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one (10 ppm) enhanced the perception of sweetness and improved the orange flavor in the drink.
  • 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman-4-one when used with a sweetness modifier, enhances the perception of sweetness and sugary mouthfeel, and masks off-taste such as bitterness and astringency.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation de nouveaux composés pour moduler la perception de la sucrosité, améliorer la sensation en bouche de sucrosité et/ou masquer le goût d'un modificateur de sucrosité et pour diminuer la quantité d'un modificateur de sucrosité utilisé dans un consommable.
PCT/US2025/017463 2024-03-05 2025-02-27 Nouvelles compositions pour la modulation du goût Pending WO2025188525A1 (fr)

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CN2024080039 2024-03-05
CNPCT/CN2024/080039 2024-03-05

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