WO1998031242A1 - Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout - Google Patents

Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout Download PDF

Info

Publication number
WO1998031242A1
WO1998031242A1 PCT/US1996/020264 US9620264W WO9831242A1 WO 1998031242 A1 WO1998031242 A1 WO 1998031242A1 US 9620264 W US9620264 W US 9620264W WO 9831242 A1 WO9831242 A1 WO 9831242A1
Authority
WO
WIPO (PCT)
Prior art keywords
product
hydroxypropiophenone
wintergreen
flavor
methyl salicylate
Prior art date
Application number
PCT/US1996/020264
Other languages
English (en)
Inventor
Michael J. Greenberg
Original Assignee
Wm. Wrigley Jr. Company
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 Wm. Wrigley Jr. Company filed Critical Wm. Wrigley Jr. Company
Priority to AU20499/97A priority Critical patent/AU2049997A/en
Priority to PCT/US1996/020264 priority patent/WO1998031242A1/fr
Publication of WO1998031242A1 publication Critical patent/WO1998031242A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • the present invention relates to the use of 2'- hydroxypropiophenone as a flavor ingredient. More particularly, the present invention relates to the use of 2'-hydroxypropiophenone as an enhancement, or as complete or partial replacement for methyl salicylate in chewing gum, foods, dentrifices, mouthwashes and other orally consumable compositions.
  • Methyl salicylate is a commonly used flavor and fragrance compound which provides the characteristic flavor of wintergreen to foods, beverages, candies, chewing gums and oral care products. It is also used to enhance the flavor of mint flavored products, for example, those flavored primarily with peppermint or spearmint oils. Methyl salicylate is also used as an active ingredient in topically applied anesthetic ointments promoted for relief of muscle aches, arthritis and similar complaints.
  • Salicylic acid derivatives most notably acetyl salicylic acid (more commonly known as aspirin) , often have pharmaceutical properties such as anagestic, anticoagulant, antipyretic and anti-fungal activity. Not surprisingly. these pharmaceutical agents are generally toxic to some degree. Methyl salicylate itself is known to be toxic at dosage levels well above those found in oral products.
  • the present invention provides improved flavor for products.
  • the term "products" refers to manufactured goods which are intended to be orally consumed or at least taken into the oral cavity. Products include foods, beverages, confections, pharmaceuticals, chewing gums, mouthwashes, toothpastes and other items meeting the above definition. Accordingly, the present invention provides for the use of 2'-hydroxypropiophenone in fiavorant compositions used in such products to enhance or replace methyl salicylate. When used as a replacement for methyl salicylate, the compound may be used alone or in combination with other wintergreen-like flavor components and the replacement may be partial or complete.
  • a wintergreen-flavored product comprising, as a fiavorant, methyl salicylate is enhanced by addition of 2'- hydroxypropiophenone.
  • the weight ratio of methyl salicylate to 2'-hydroxypropiophenone in the product is between about 1:1 and 10:1, more preferably between about 2:1 and 4:1 and most preferably about 3:1.
  • a method of reducing the level of methyl salicylate in a wintergreen-flavored product formulation comprises the steps of modifying a wintergreen-flavored product formulation by substituting 2'-hydroxypropiophenone for at least a portion of the methyl salicylate.
  • other flavor components having flavor similar to methyl salicylate are also present.
  • all of the methyl salicylate is replaced.
  • 10 to 50% by weight of the methyl salicylate is replaced.
  • about 25% by weight of the methyl salicylate is replaced.
  • a salicylate-free, wintergreen- flavored product comprises 2'-hydroxypropiophenone and optionally other non-salicylate flavor components.
  • a method of adding a wintergreen flavor note to a non-wintergreen-flavored product comprises the steps of formulating a non-wintergreen flavor, adding 2'-hydroxypropiophenone to the flavor, and adding the flavor to the product.
  • 2'- hydroxypropiophenone comprises l to 35% by weight of the flavor.
  • 2'-hydroxypropiophenone comprises 5 to 20% by weight of the flavor.
  • a chewing gum comprises a gum base, a sweetener and a flavor which comprises 2'- hydroxypropiophenone.
  • the chewing gum is a wintergreen-flavored chewing gum.
  • the chewing gum contains from about 0.01 to about 1.0% 2'- hydroxypropiophenone by weight of the chewing gum.
  • the chewing gum contains from about 0.05 to about 0.40% 2 -hydroxypropiophenone by weight of the chewing /31242
  • Methyl Salicylate (2-hydr ⁇ xybenzoic acid methyl ester) is a commonly used fiavorant. It was originally derived from natural sources but now is primarily produced by esterification of salicylic acid with ethanol. Methyl Salicylate has the following structure:
  • salicylates that is esters of salicylic acid
  • ethyl salicylate has such a flavor.
  • the inventor has now made the surprising discovery of a non-salicylate compound which has a flavor similar to methyl salicylate and which can enhance the flavor of methyl salicylate. This allows the compound to be substituted for methyl salicylate at levels of 5 to 100% by weight of the original quantity of methyl salicylate, depending on the application.
  • the compound may be used in wintergreen flavored compositions as well as in compositions flavored with mint oils and other compatible flavor systems.
  • the compound is 2'-hydroxypropiophenone and has the following structure: 8/31242
  • the present invention contemplates the use of 2'- hydroxypropiophenone as a fiavorant for chewing gums, candies, dentrifices, mouth washes and other food and oral compositions.
  • 2'-hydroxypropiophenone may be used to enhance the wintergreen flavor or to replace a portion or all of that compound.
  • 2 '-hydroxypropiophenone may be used as the sole fiavorant or it may be combined with other flavor compounds to impart a wintergreen flavor or wintergreen note to the composition. More particularly, 2'- hydroxypropiophenone may be blended with peppermint oil, spearmint oil, menthol, cinnamon flavor, anise, root beer flavor, bubble gum flavor, spice flavors, citrus oils and fruit flavors. Such flavor compositions may include natural or artificial components or blends of the two. Combinations of 2 ' -hydroxypropiophenone with cooling agents such as menthol, menthone ketals, N-substituted-p-menthane carboxamides and 3-l-menthoxypropane-l,2-diol are specifically completed.
  • cooling agents such as menthol, menthone ketals, N-substituted-p-menthane carboxamides and 3-l-menthoxypropane-l,2-diol are specifically completed.
  • 2 '-hydroxypropiophenone may comprise from about 1 to about 99 weight percent of the complete flavor blend.
  • the blend comprises 20 to 80% 2 '-hydroxypropiophenone.
  • the precise usage level will depend on the nature of the desired flavor of the final product and the preferences of the flavorist compounding the flavor composition.
  • the flavored product is a chewing gum.
  • Chewing gums typically contain about 0.25 to about 5%, and most typically about 1% flavor by weight.
  • a chewing gum comprises a water- soluble bulk portion, a water-insoluble chewable gum base portion and typically, water-insoluble flavor ingredients.
  • the water-soluble bulk portion dissipates with a portion of the flavor over time during chewing.
  • the gum base portion is retained in the mouth throughout the chew.
  • the insoluble gum base generally comprises elastomers, resins, fats and oils, waxes, softeners and 10 inorganic fillers.
  • the insoluble gum base constitutes between about 5% to about 95% of the gum, and more preferably about 20% to 30%. All percent values represent weight percent.
  • the gum base typically also includes a filler component.
  • the filler component may be calcium carbonate, magnesium carbonate, talc, dicalcium phosphate, and the like.
  • the filler may constitute between about 5% to about 60% of the gum base.
  • the filler comprises about 5% to about 50% of the gum base.
  • the gum base also contains softeners, including glycerol onostearate and glycerol triacetate.
  • gum bases may also contain additional ingredients such as antioxidants, colors, and emulsifiers. The present invention contemplates using any commercially acceptable gum base.
  • the water-soluble portion of chewing gum may further comprise softeners, sweeteners, and flavors and combinations thereof.
  • the softeners are added to the chewing gum to optimize the chewing ability and mouth feel of the gum.
  • Softeners also known in the art as plasticizers, generally constitute about 0.1% to about 15% of the chewing gum.
  • Softeners contemplated by the present invention include glycerin, lecithin and combinations thereof.
  • Aqueous sweetener solutions such as those containing sorbitol, hydrogenated starch hydrolysates, corn syrup, and combinations thereof may be used as softeners and binding agents in gum.
  • Sweeteners contemplated by the present invention for use in chewing gum include both sugar and sugarless components.
  • Sugar sweeteners generally include saccharide- containing components commonly known in the art and include, but are not limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup solids and the like, alone or in any combination.
  • Sugarless sweeteners include components with sweetening characteristics but are devoid of the commonly known sugars and comprise, but are not limited to, sugar alcohols such as sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, hydrogenated isomaltulose and the like, alone or in any combination.
  • high intensity sweeteners such as aspartame, sucralose, cyclamate, acesulfame-K, dihydrochalones, glycyrrhizin, alitame, and saccharin, and the food acceptable salts thereof.
  • any combination of sugar/sugarless sweeteners may be employed in the chewing gum.
  • a sweetener may be present in a chewing gum in whole or in part as a water-soluble bulking agent, and that the softener may be combined with a sweetener such as an aqueous sweetener solution.
  • chewing gum is manufactured by 12 sequentially adding the various chewing gum ingredients to any commercially available mixer known in the art. After the ingredients have been thoroughly mixed, the gum mass is discharged from the mixer and shaped into the desired forms such as by rolling into sheets and cutting into sticks, extruding into chunks, or casting into pellets.
  • the ingredients are mixed by first melting gum base and adding it to the running mixer. The base may also be melted in the mixer itself. Color may also be added at this time. A softener such as glycerin may then be added next along with the syrup and a portion of bulking agent. Further portions of the bulking agents may be added to the mixer.
  • the flavor ingredients are added to the gum mixture near the end of the mixing process.
  • the entire mixing procedure takes from about 5 minutes to 15 minutes, however, longer mixing times may be required.
  • the flavored product is a food, candy, mouthwash, toothpaste, or other oral product.
  • Examples 1-4 demonstrate replacement of methyl salicylate with 2 '-hydroxypropiophenone in a sweet water taste test.
  • EXAMPLE 1 A control solution for taste testing was prepared by dissolving 0.2 ml of methyl salicylate in 10 ml of ethanol. One milliliter of this solution was dissolved in 100 ml of a 5% sucrose aqueous solution.
  • EXAMPLE 2 A solution was prepared as in Example 1 except that 0.02 ml of methyl salicylate was replaced with 2'- hydroxypropiophenone (10% replacement) .
  • EXAMPLE 3 A solution was prepared as in Example 1 except that 0.05 ml of methyl salicylate was replaced with 2'- hydroxypropiophenone (25% replacement) .
  • EXAMPLE 4 A solution was prepared as in Example 1 except that 0.10 ml of methyl salicylate was replaced with 2'- hydroxypropiophenone (50% replacement) .
  • Example 3 25% Slightly astringent, slightly sweeter, slightly floral
  • Example 4 50% Astringent mouth feel, slightly bitter, sweet, slightly burning, slightly perfumery, medicinal, slight anise note.
  • Examples 5 through 8 illustrate, by way of example, the practice of various embodiments of the present invention.
  • a wintergreen flavored toothpaste having enhanced wintergreen flavor is prepared from the following formula:
  • EXAMPLE 6 A wintergreen-flavored chewing gum having a reduced methyl salicylate level is prepared according to the following formula: Percent Bv Wei ⁇ ht
  • Example 7 The chewing gum of Example 6 is formulated to be salicylate-free by substituting the following flavor compounds for those in Example 6: 17
  • EXAMPLE 8 A peppermint flavored mouthwash is given a wintergreen note without addition of methyl salicylate according to the following formula:

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Nutrition Science (AREA)
  • Confectionery (AREA)
  • Cosmetics (AREA)

Abstract

La 2'-hydroxypropiophénone est utilisée comme aromatisant pour renforcer le goût de produits aromatisés au wintergreen et pour donner une note de wintergreen aux produits non aromatisés au wintergreen. Ledit composé peut être utilisé en particulier pour remplacer partiellement ou totalement le salicylate de méthyle utilisé comme aromatisant dans des produits. Le composé de l'invention est destiné à être utilisé dans des produits consommés par voie orale, par ex. gomme à mâcher, bains de bouche, dentifrices, produits pharmaceutiques, aliments, boissons et confiseries.
PCT/US1996/020264 1997-01-15 1997-01-15 Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout WO1998031242A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU20499/97A AU2049997A (en) 1997-01-15 1997-01-15 Enhanced flavors using 2'-hydroxypropiophenone
PCT/US1996/020264 WO1998031242A1 (fr) 1997-01-15 1997-01-15 Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1996/020264 WO1998031242A1 (fr) 1997-01-15 1997-01-15 Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout

Publications (1)

Publication Number Publication Date
WO1998031242A1 true WO1998031242A1 (fr) 1998-07-23

Family

ID=22256317

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/020264 WO1998031242A1 (fr) 1997-01-15 1997-01-15 Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout

Country Status (2)

Country Link
AU (1) AU2049997A (fr)
WO (1) WO1998031242A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001068044A1 (fr) * 2000-03-14 2001-09-20 Unilever N.V. Composition orale renfermant 2'-hydroxypropiophenone
WO2022122836A1 (fr) * 2020-12-10 2022-06-16 Givaudan Sa Méthyl-fluoro-hydroxybenzoates dans des produits de consommation
WO2022180141A1 (fr) 2021-02-25 2022-09-01 Givaudan Sa Procédés de masquage de mauvais goûts

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947603A (en) * 1972-04-13 1976-03-30 Firmenich & Cie Flavoring agent
US5128154A (en) * 1989-12-28 1992-07-07 Wm. Wrigley Jr. Company Method of treating wintergreen flavors so as to eliminate undesirable offnotes associated therewith

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947603A (en) * 1972-04-13 1976-03-30 Firmenich & Cie Flavoring agent
US5128154A (en) * 1989-12-28 1992-07-07 Wm. Wrigley Jr. Company Method of treating wintergreen flavors so as to eliminate undesirable offnotes associated therewith

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001068044A1 (fr) * 2000-03-14 2001-09-20 Unilever N.V. Composition orale renfermant 2'-hydroxypropiophenone
US6436371B2 (en) 2000-03-14 2002-08-20 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Oral composition
WO2022122836A1 (fr) * 2020-12-10 2022-06-16 Givaudan Sa Méthyl-fluoro-hydroxybenzoates dans des produits de consommation
WO2022180141A1 (fr) 2021-02-25 2022-09-01 Givaudan Sa Procédés de masquage de mauvais goûts

Also Published As

Publication number Publication date
AU2049997A (en) 1998-08-07

Similar Documents

Publication Publication Date Title
US6159509A (en) Method of making chewing gum products containing perillartine
CA2634869C (fr) Compositions produisant une sensation quasiment similaire a celle du menthol
US6197288B1 (en) Malodor counteractant compositions and method for preparing and using same
US5348750A (en) Enhanced flavors using menthone ketals
US6436369B2 (en) Anti-plaque emulsions and products containing same
US20030072842A1 (en) Chewing gum having prolonged sensory benefits
EP0485170A1 (fr) Arômes améliorés utilisant des cétals de menthone
ES2656187T3 (es) Composiciones de goma humectantes de la boca y productos que las contienen
AU2007289270B2 (en) Indulgent gum base and chewing gum compositions containing same
BRPI0710245A2 (pt) impacto de complexo de fosfato de cálcio em cáries dentais
BRPI0710844A2 (pt) composição de confeito , método e kit de remineralizar e de conferir resistência a ácido a superficie dos dentes de um mamìfero
CA2020891A1 (fr) Composes antiseptiques contenant des composes d'hexahydro-5-pyrimidinamine et un surfactant amphoterique, et methode de preparation
ES2207852T3 (es) Composiciones aromatizantes potenciadas que contienen n-etil-p-mentano-3-carboxamida y metodo de fabricacion y utilizacion de las mismas.
RU2536137C2 (ru) Композиция жевательной резинки, увлажняющая рот (варианты), и содержащие их продукты
JP2002542185A (ja) 食品用酸にカルシウムを含む歯に有益なチューインガム
US5795616A (en) Enhanced flavors using 2'-hydroxypropiophenone
CA2526981C (fr) Composition de friandise dentaire antiplaque
US6899911B2 (en) Ethyl 4-(thioacetoxy)butyrate as a flavoring agent and methods for preparing and using same
US5993879A (en) Methods for using 1-methylbutyl and 1-methylhexyl esters as flavoring agents
WO2001028503A1 (fr) PRODUITS D'HYGIENE PERSONNELLE A BASE DE N-[N-(3,3-DIMETHYLBUTYL)-1-α-ASPARTYL]-L-PHENYLALANINE METHYL ESTER
WO1998031242A1 (fr) Utilisation de 2'-hydroxypropiophenone pour le renforcement du gout
CA2305769C (fr) Produits de gomme a macher contenant de la peryllartine et methode de fabrication connexe
WO1992009283A1 (fr) Composes d'hexahydro-5-pyrimidinamine stabilises en solution aqueuse et leurs procedes de preparation
GB2364231A (en) Flavouring agent
WO1997028805A1 (fr) Compositions therapeutiques contenant un compose hexahydro-5-pyrimidinamine et un compose morpholine-ether

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IS JP KE KG KP KR KZ LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG UZ VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE LS MW SD SZ UG AM AZ BY KG KZ MD RU TJ TM AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: JP

Ref document number: 1998539527

Format of ref document f/p: F

122 Ep: pct application non-entry in european phase