US20080000614A1 - Hot flavor and skin sensation composition - Google Patents

Hot flavor and skin sensation composition Download PDF

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US20080000614A1
US20080000614A1 US11/853,656 US85365607A US2008000614A1 US 20080000614 A1 US20080000614 A1 US 20080000614A1 US 85365607 A US85365607 A US 85365607A US 2008000614 A1 US2008000614 A1 US 2008000614A1
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component
composition
hot
acid
flavor
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US11/853,656
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Catherine MAUREL
Anh Le
Jerome Barra
Christian Starkenmann
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Firmenich SA
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Assigned to FIRMENICH SA reassignment FIRMENICH SA CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S NAME AND ADDRESS TO THE CORRECT ASSIGNEE (FIRMENICH SA) PREVIOUSLY RECORDED ON REEL 019919 FRAME 0325. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECTIVE ASSIGNMENT. Assignors: MAUREL, CATHERINE, BARRA, JEROME, STARKENMANN, CHRISTIAN, LE, ANH
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10Natural spices, flavouring agents or condiments; Extracts thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/82Acid flavourants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9794Liliopsida [monocotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24Thermal properties
    • A61K2800/242Exothermic; Self-heating; Heating sensation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24Thermal properties
    • A61K2800/244Endothermic; Cooling; Cooling sensation

Definitions

  • the present invention relates to the field of flavors and fragrances.
  • the present invention relates to a flavor or skin sensation composition, to the use of a hot component, a cooling component, a bitter component and optionally an acid, to prepare a flavor or skin sensation composition and to food or body care products comprising the composition.
  • the present invention aims at providing an ingredient suitable for foods but also for topically administered body care products, such as shampoos and lotions, the ingredient providing a clean, warming trigeminal sensation substantially free of undesired off-notes typically associated with natural extracts, such as the black pepper extracts (spicy, earthy off-note) or mustard oil (pungent sulfury effect), for example.
  • Capsaicin naturally present in various plant species of the Capsicum gender, is a well-known compound providing a strongly warming, hot trigeminal sensation and would thus be ideally employed in compositions providing a warming sensation to a food product.
  • the use of capsaicin and its derivatives is limited by the fact that it may cause skin irritations. What is more, capsicum oleoresin has a pungent and oily off-note, which further puts a hindrance to its use in foods or body care products.
  • the present invention now provides a hot, warming effect devoid of oily off-notes and skin-irritation effects typical for capsaicin.
  • it provides a flavor or skin sensation composition providing a clean, hot trigeminal effect while reducing the amount of capsaicin present in the composition.
  • the present invention further provides ingredients synergistically interacting with hot compounds in a way that the hot intensity is increased, in order to reduce the amount of hot, warming ingredients in a flavor composition.
  • the present inventors found that by preparing a composition comprising at least a hot component, a cooling component and a bitter component, a clean hot and/or warming sensation was provided, which is devoid of oily off-notes and further undesired characteristics.
  • the sensation was particularly useful, clean and positively evaluated in food products, oral care and body care products.
  • the present invention provides, in a first aspect, a flavor or skin sensation composition
  • a flavor or skin sensation composition comprising, a hot component, a cooling component, a bitter component and optionally an acid component.
  • the present invention provides the use of a composition according to the invention, to prepare a flavor, perfume or skin sensation composition.
  • the present invention provides the use of a composition according to the invention, to provide a hot flavor to a food product.
  • the invention provides a method to confer, enhance, improve or modify the hot and clean taste to a food product, the method comprising the steps of adding to the food product a flavor composition according to the invention.
  • the invention provides a food product, an oral care product, a pharmaceutical product and a body care product comprising the flavor or skin sensation composition of the invention.
  • FIG. 1 shows a comparison of the taste profiles of four hot ingredients, including the composition of the present invention (according to Example 1), from sugar-free hard-boiled candy application perceived by trained panelists. Statistically significant at 99% (**) and 99.9% (***) level of confidence.
  • FIG. 2 shows comparison of the hot intensity, flavor intensity and overall liking of sugar-free hard-boiled candy application comprising (A) the hot composition of the present invention (according to Example 1), and, (B) capsicum oleoresin as perceived by trained panelists at iso-hot intensity. Statistically significant at 99% (**) level of confidence.
  • composition of the present invention comprises a hot component, a cooling component, a bitter component, and optionally an acid component.
  • the hot taste is a hot, clean taste if evaluated by a skilled panel of experienced tasters and has significantly reduced off-notes and oily organoleptic properties if compared to equally hot compositions based on natural extracts alone or other compositions than those of the present invention.
  • Significantly reduced preferably refers to statistically significance at a confidence level of at least 90% and established with a panel of at least 15 tasters.
  • the present invention provides a composition comprising a hot component, a cooling component a bitter component and optionally an acid component.
  • the present invention provides a composition comprising a hot component, a cooling component and a bitter component.
  • the present invention provides a composition comprising a hot component, a cooling component, a bitter component and an acid.
  • the hot component is an ingredient, which provides a hot, warming sensation when brought into contact with the oral cavity or the skin.
  • the hot component provides a hot, warming sensation mediated by the trigeminal nerve.
  • ingredients typically used in the food and oral care industry that can serve as hot component for the purpose of the invention include piperine, pelargonyl vanillyl amide, vanillyl butyl amide, vanillin butyl ether, eugenol, gingerol, polygodial, shogoal, galangal acetate, capsaicin(N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide and/or (6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide), capsaicin analogues and mixtures comprising two or more of these.
  • the hot component consists of 5-90% of capsicum oleoresin, and 10-95% of at least one other hot ingredient.
  • natural extracts which can directly be used for working the present invention, such as black pepper extract, mustard oil, ginger oleoresin, jambu oleoresin, capsicum oleoresin, Japanese pepper extract, chilli pepper extract, Zealandn pepper extract, for example.
  • Other examples of hot, warming compounds are disclosed in European patent application EP 1 121 927 A2, in particular in claim 6 of this reference, which is enclosed herein.
  • the cooling component is preferably a purified compound, but may also be provided in the form of an extract, which provides, when brought in contact with the skin or oral cavity, a cooling sensation, which is mediated by the trigeminal nerve.
  • the cooling component is selected from the group consisting of menthol, menthyl succinate, menthyl lactate, p-menthane-3,8-diol, 8-p-menthen-3-ol (COOLACT P®, Takasago), 3-(3′-P-menthanyloxy)-1,2-propanediol (COOLANT AGENT 10®, Takasago), menthone glycerol ketal (FRESCOLAT® MGA, Haarmann & Reimer), 2-(1-methylpropyl)-1-cyclohexanone (FRESKOMENTHE®, Givaudan), N-ethyl-3-P-menthanecarboxamide (WS-3, Millennium Specialty Chemicals), aspartic acid, N-(4-hydroxy-3-methoxybenzyl)nonanamide, 5-[5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-2,
  • Cooling agents such as those mentioned above are commercially obtainable and their synthesis is well-known to the skilled person. Some of the above and further cooling agents are disclosed to the skilled person, for example in H. R. Watson, Flavor: Its Chemical, Behavioral and Commercial Aspects Apt, C. M. Ed. Westview; Boulder Colo. ⁇ (1977), 31-50. This reference comprises a list of about 1200 cooling and/or minty compounds, including WS compounds, developed by the Wilkinson-Sword company.
  • the bitter component is a compound or, more generally, an extract having bitter organoleptic properties.
  • Bitterness is one of five recognized basic tastes (besides sweet, salty, sour and umami) and is mediated by taste buds at the back of the tongue. It can readily be attributed to compounds, ingredients, for example.
  • the bitter component is selected from bitter triterpenes, glucosides of monoterpenes, sesquiterpenic lactones, humulone, lupulone, flavonones, quinines, and mixtures of these.
  • Examples for bitter plant extracts include Quassia extract (also called bitter ash extract, FEMA No. 2971), quinquina extract, chamomile oils (FEMA No. 2272 to 2274), gentian root extract (FEMA No. 2506), hops extracts and oils (FEMA No. 2578 to 2580, artichoke leaves oil, just to mention a few.
  • the composition of the present invention further comprises an acid.
  • the acid is food-grade and hence suitable for human consumption.
  • the acid is a C 2 -C 8 , more preferably a C 2 -C 6 organic acid.
  • suitable acids are citric acid, acetic acid, succinic acid, pyruvic acid, lactic acid, propionic acid, malonic acid, oxalic acid, amongst many others.
  • inorganic acids which are acceptable for human consumption may be used, equally, for example, HCl, H 3 PO 4 (phosphoric acid), H 2 SO 4 (nitric acid), etc.
  • any or all of the hot component, the cooling component and/or the bitter component, if present, is/are present in the form of a natural extract.
  • the present composition may comprise both, natural extracts and isolated, for example chemically synthesised compounds. Accordingly, in an embodiment, any of the hot component, and/or the bitter component, if present, is/are present in the form of a natural extract.
  • Natural extracts comprise extracts made by any extraction method and include aqueous extracts, alcohol extracts, essential oils, supercritical fluids extract, hydrodistillated extract, for example.
  • any or all of the hot component, the cooling component and/or the bitter ingredient, if present, is/are present in the form of isolated compounds.
  • the cooling component and the acid are present in the form of pure, isolated compounds, or solutions with defined quantity of the isolated compound, for example.
  • the composition of the present invention preferably comprises at least one solvent, or a mixture of solvents, to dissolve the different components of the composition according to the invention.
  • Solvents of current use for the preparation of a flavoring formulation are also well known in the art and the solvent is most of the time part of a flavoring composition.
  • Solvent currently used in this framework include for instance benzyl alcohol, propylene glycol, triacetine, neobee, vegetable oils, ethanol or limonene.
  • a mixture of solvents may be useful to dissolve hydrophobic and hydrophilic components in the same solution.
  • the components of the present invention may be is a solution comprising 20-95%, preferably 40-90%, more preferably 50-85% of solvent.
  • percentages are percentages by weight, unless otherwise indicated. Similarly, if proportions are indicated as parts, parts of weight are meant.
  • composition of the invention may further comprise other ingredients typically used in flavor compositions, for example.
  • the composition may comprise further flavors.
  • the composition may also comprise adjuvants that allow the composition to meet technical requirements, such as stability or tonality persistence.
  • stability or tonality persistence Today, the range of products types and product formulations that are flavored has become so extensive and subjected to frequent changes that an approach made on a product-by-product basis and on the definition for each case of the adjuvants that can be used is impractical. This is why a list of adjuvants currently used in flavoring formulations is not given here.
  • a skilled person in the art for example a flavorist is capable of choosing these ingredients as a function of the product to be flavored and of the nature of the flavoring ingredients contained in the formulation.
  • the composition of the invention further comprises a lift enhancer.
  • Lift enhancers are adjuvants capable of increasing the volatility of the other flavors or compounds of the composition of the invention, preferably without inferring or contributing to the flavor or other organoleptic properties of a flavor composition.
  • Examples of lift enhancers belong to various chemical groups and include alcohols, aldehydes, ketals, esters, ethers or sulfur compounds, for example.
  • lift enhancers typically used in industry are ethyl acetate, acetaldehyde, ethanol, acetal, acetone, butyraldehyde, propionaldehyde, dimethylsulfide, ethyl formate, propylmercaptan, butylmercaptan, methylethylcetone.
  • the composition of the present invention comprises 0.5-60% by weight of a hot component, 0.5-60% of a cooling component, 0.05-50% of a bitter component and optionally 0-60% of an acid component or acid and 0-40% of a lift enhancer.
  • the composition comprises 1-50% of a hot component, 1-50% of a cooling component and 0.1-20% of a bitter component.
  • the composition comprises 1-50% of a hot component, 1-50% of a cooling component, 0.1-20% of a bitter component and 1-50% of an acid component.
  • the composition comprises 2-40% of a hot component, 2-40% of a cooling agent, 0.2-20% of a bitter compound and 2-40% of an acid. Even more preferably, the composition comprises 4-30% of a hot component, 4-30% of a cooling agent, 0.5-15% of a bitter compound and 4-30% of an acid. Preferably, these compositions comprises 0.5-10% of a lift enhancer.
  • the above percentages refer to the amount of plant extracts as concerns the hot and the bitter component, because hot and bitter principles are mainly commercialized in the form of extracts.
  • the percentages of cooling agent and acid are valid for pure, isolated compounds, because these components are generally commercialized as pure compounds, or solutions with known dilution of the active principle, for example the cooling agent.
  • these percentages do not consider the amounts of other ingredients, such as solvents and adjuvants or other flavors, possibly being present in a flavor composition, but only refer to the part contributing to enhance a warming sensation given by combination of hot component, cooling agents, as well as an acid and/or a bitter component, and, optionally, a lift enhancer.
  • composition of the invention can be made by simply mixing all components of the invention with a solvent at room temperature, preferably at the weight-ratios mentioned above.
  • the present invention provides the use of a composition according to the invention to prepare a flavor or a skin sensation composition.
  • the present invention provides of a composition according to the invention to provide a hot flavor to a food product.
  • the present invention provides a method for imparting a hot taste to a food product, the method comprising the steps of adding to the food product the composition of the present invention.
  • composition of the invention may be used directly as it is or added to food products as discussed below.
  • the present invention provides a food product comprising the composition of the present invention.
  • the composition of the invention may directly be added to a food product at the stage where flavors are generally added.
  • the liquid composition may be encapsulated in a matrix, such as a carbohydrate, phospholipid, or protein matrix, such as a gelatin matrix, for example, or any bioactive matrix, in order to provide a shelf-stable, dry form of the flavor or skin composition of the invention.
  • the present invention provides a delivery system comprising the composition of the present invention.
  • the delivery system is in the form of a particulate composition and/or a powder.
  • the composition may be encapsulated following standard procedures in spray-dried powders.
  • the composition may be encapsulated in a matrix, which is in a glassy state at room temperature.
  • the composition of the invention may be encapsulated in rod-like granules the preparation of which is disclosed in U.S. Pat. No. 4,707,367.
  • the composition of the invention may be used in liquid food products and/or in products that are solid.
  • the food product is selected from the group consisting of a confectionery product, a bakery product, a beverage carbonated or non-carbonated, a alcoholic drink, a dairy product, a soy product, a soup, a dressing, a gravy, a condiment, a sauce, and a dip, a snack, noodles, chips, meat and fish, for example.
  • confectionery products examples include chocolates, candies, chewing gums, for example.
  • the present invention provides an oral care product according to the invention.
  • the product may be a toothpaste, a tooth-gel, a mouthwash.
  • the present invention provides a pharmaceutical product comprising the flavor composition according to the invention.
  • a pharmaceutical product comprising the flavor composition according to the invention.
  • examples of such products are syrups, drugs provides in tablets or capsules.
  • the present invention provides a body care product comprising the composition of the present invention.
  • the composition of the invention is put in a lip balm, a shampoo, a soap, a cream, and/or a body lotion, a perfume.
  • the composition comprises a hot component and a cooling component, human skin will be susceptible to make a unique sensational experience when getting in contact with the composition of the present invention.
  • the products of the present invention such as foods, beverages, pharmaceuticals, oral care and body care products may be prepared following known procedures and the composition of the invention may be added in liquid or encapsulated particulate form, depending on the product, to the product at the same time as flavors or perfumes are typically added.
  • a composition providing hot, warming trigeminal properties was prepared according to Table 1 below. All components were mixed under stirring in food-grade solvents. The composition, when tasted as such, provided a strong and clean hot, warming taste. Earthy, oily off-notes and the peppery note typical for piperine were not detected or strongly reduced. TABLE 1 Components for hot trigeminal composition Ingredient Characteristics Origin % by weight Piperine Hot component Aldrich 1) , FEMA 2) No. 8.1 2909 Menthol nat. Cooling agent Aldrich, FEMA No. 5.5 2665 Quassia Bitter component Chart 4) , FEMA No. 0.2 extract 3) 2971 Acetic acid Acid Aldrich, FEMA No.
  • a further hot flavor and skin sensation composition was prepared with the same procedure as in Example 1, but with the components indicated in Table 2 below.
  • the composition when tasted as such, provided a strong and clean hot, warming taste. Earthy and oily off-notes typical for capsaicin were not detected.
  • TABLE 2 Components for hot trigeminal composition Ingredient Characteristics Origin % by weight Capsicum Hot component Penta 6) , FEMA No. 1.3 oleoresin 2234 Menthol nat. Cooling agent Aldrich, FEMA No. 5.5 2665 Quassia extract 3) Bitter component Chart 4) , FEMA No. 0.2 2971 Acetic acid Acid Aldrich, FEMA No. 3 2006 Ethyl acetate Lift enhancer Aldrich, FEMA No. 2.5 2414 Neobee Solvent Stepan 5) 43.75 Triacetin Solvent Aldrich, FEMA No. 43.75 2007 6) Penta Manufacturing, Livingston, USA
  • Isomalt (100 g) and water (30 g) were mixed and heated to 160-165° C. in a copper pan. At 165° C., the copper pan was removed from the gas frame and placed in a warm water bath (40° C.). After a few seconds, the copper pan was removed and the temperature checked. When temperature reached 135° C., the flavoring system according to Table 3 was added. The mixture comprising isomalt and was further complemented with 1% of an aqueous solution containing Aspartame (10%) and Acesulfame-K (5%).
  • hot flavors were added according to Table 2 below, in which hot extracts commercially obtained were diluted in the same proportions as in Example 1 (80.2% of solvents) to provide flavor solutions allowing easy handling and dosing.
  • the cooked mass was then poured at ambient temperature (at less than 40% relative humidity) in appropriate Teflon molds.
  • Flavor components of different samples of sugar-free hard-boiled candy Flavor (19.8%) in Origin and Dosage in solvent Code candy (w/w) Black pepper Chart, FEMA 0.05% extract 1) 2846 Mustard oil Fleurchem 7) 0.05% FEMA 2034 Capsicum Penta, 0.05% oleoresin FEMA 2234 Hot Mix Example 1 0.05% 7) Fleurchem Inc., Flemington, USA Sensory Evaluation of Composition of the Invention In Candy
  • Example 3 The different sugar-free hard-boiled candies obtained in Example 3 were evaluated by 20 trained panelists in one tasting session and tested two samples each, which were presented in a blind and randomized manner. The intensity of each attribute (hot, pungent, spicy, peppery, oily, off-notes and overall intensity) was evaluated on a 0 to 10 linear scale from absent to strong. For data analysis, a Student's t-test was performed to identify differences between the two samples.
  • the composition of the invention (“hot mix”) provides a cleaner hot taste compared to single ingredient like a capsicum oleoresin with its pungent and oily off-notes, black pepper extracts with their typical peppery spicy earthy character, or a mustard oil with its pungent sulfury effect. ( FIG. 1 ).
  • the hot intensity with the composition of the invention is stronger than with black pepper extract or mustard and nearly as strong as that of capsicum oleoresin. Therefore, the blend of the present invention is capable of partly replacing capsaicin content (capsaicin present in capsicum oleoresin, for example).
  • the purpose of this example is to prepare sweets based on different hot trigeminal ingredients at iso-hot intensity (having the same hot intensity as perceived by a panel) to compare gustative properties other than hotness.
  • Example 4 the same procedure as in Example 3 was performed to prepare sugar-free hard boiled candy, with the difference that other quantities of hot ingredients were added, as shown in Table 4 below.
  • a lemon-flavor was added at 0.06% to the present candies.
  • the composition of the invention hot mix
  • the composition of Example 1 Table 1
  • a 20 wt. % solution of capsicum oleoresin was used in the same solvents as in Example 1.
  • Flavor components of different samples of sugar-free hard-boiled candy Dosage in Origin and Candy Flavor Code (w/w) Lemon Firmenich 0.060% Hot Mix Example 1 0.030% Lemon Firmenich 0.060% Capsicum Fleurchem 0.013% oleoresin FEMA 2234 Sensory Evaluation of Hard-Boiled candy at Iso-Hot Intensity
  • the trained panelists participated in one tasting session and tested the two samples above each (present invention and capsicum oleoresin), which were presented in a blind and randomized manner.
  • the intensity of each attribute was evaluated on a 0 to 10 linear scale from hot intensity, flavor intensity and overall liking.
  • a Student's t-test was performed to identify significant differences between the two samples.
  • composition of the present invention provided a significantly (p ⁇ 0.1) stronger flavor intensity and over-all liking than candies comprising capsicum oleoresin. Therefore, the composition present invention is suitable to replace capsicum oleoresin to provide hot, warming trigeminal properties while being organoleptically preferred by consumers.
  • composition of the present invention was prepared according to standard procedures. Once, a glassy matrix of carbohydrates comprising 9% of a flavor composition according to Example 1, but at double concentration (hot composition: 39.6%; solvents: 61.4%) was prepared according to the procedure outlined in U.S. Pat. No. 4,707,367 to obtain a particulate composition of rod-like granules.
  • a spray-dried powder of encapsulated flavor composition was prepared in a carbohydrate matrix (50% maltodextrin, 40% modified starch) with 20% load of the same concentrated composition as for the rod-like granules obtained above.
  • carbohydrate matrix 50% maltodextrin, 40% modified starch
  • an encapsulate of the composition of the invention having the double flavor load of the spray-dried encapsulate obtained above was prepared.
  • Sugar-free, cinnamon-flavored chewable tablets were prepared in that crystalline sorbitol (97.9%), aspartame (0.05%), acesulfame-K (0.05%) and magnesium stearate (2%) were mixed for 5 minutes in a Turbula (WAB AG, Basel, Switzerland). The flavoring system was added with dosages indicated in Table 5. After additional blending (1 minute), tablets of 1.20 g weight and 20 mm diameter were prepared using a Specac (Portmann Instruments, Biel, Switzerland) at a 0.40-ton compression pressure.
  • cinnamon and hot-flavored tablets comprising the composition of the invention in different encapsulated forms were compared by trained panelists according to the procedure of Examples 3 and 4. Tablets were sucked for 3 minutes while intensity was recorded at minutes 0.5, 1, 2 and 3. After 1 minute, sample 1 started to show higher hot intensity, which difference increased in the following minute to result in a significantly higher hot intensity with tablets comprising rod-like granules encapsulating the composition of the invention.
  • Sugar-free chewing gums were prepared by the following standard procedure: Crystalline sorbitol, acesulfame K and aspartame were blended in a Turbula blender. Half the blend was mixed with a pre-warmed Sierra gum base (Cafosa) in a Winkworth sigma-blade mixer at 50-55° C. for 2 minutes. The remaining powder blend was then added along with a humectant syrup (LYCASIN® 80/55, SORBIT®, glycerin) and mixed for a further 7 minutes. Finally, the flavoring system was added and mixed for one minute at the dosages indicated in Table 6 below.
  • Flavors in chewing gums comprising the hot, warming composition of the invention
  • Dosage Flavor of liquid/ load in granules/ liquid/ powder in granules/ chewing Sample Flavor Origin powder (%) gum (%) 1, 2 Liquid NOVAMINT ® 100 1 peppermint from Firmenich flavor SA, Geneva 1 Rod-like Example 5 9 0.52 granules of composition of the invention 2 Spray dried Example 5 20 1.15 powder with composition of the invention
  • Chewing gums with a clean, hot taste without earthy or oily of-notes were obtained.
  • Toothpaste Comprising the Composition of the Invention
  • Part 2 Solution of Powder Ingredients Ingredients Amount Percent Distilled Water 1500.00 grams 50.74% Saccharin Sodium 10.00 grams 0.34% Sodium Benzoate 5.00 grams 0.17% Sodium Fluoride 16.00 grams 0.54% (Supplier: Riedel de Haen AG - Germany) Polyethylene Glycol 1500 150.00 grams 5.07% Titanium Dioxide 25.00 grams 0.85% Sorbitol 70 1250.00 grams 42.29% (Supplier: Neosorb 70/70 Roquette Freres) Total 2956.00 grams 100.00% Procedure:
  • Part 3 Solution of Sodium lauryl sulfate Ingredients Amount Percent Sodium Lauryl Sulphate 75.00 grams 6.38% (Texapon K12 Supplier: Cognis Gmbh - Germany) Distilled Water 200.00 grams 17.02% Sorbosil TC 15 600.00 grams 51.06% (Supplier: Crosfield Limited) Sorbosil AC 77 300.00 grams 25.53% (Supplier: Crosfield Limited) Total 1175.00 grams 100.00% Procedure:
  • a juice-containing beverage was prepared by blending the following ingredients until uniform. Ingredient % By Weight Apple Juice Concentrate, 68° Brix 16.910% Natural Apple Flavor 0.150% Natural Allspice Flavor 0.050% Natural Cinnamon Flavor 0.005% Spray dried powder of the 0.025% invention (Example 5) Water 82.860% Total 100.000%
  • the resulting beverage was subsequently heat processed at 90° C. and held at this temperature for one minute. After the hold time, the beverage was packaged into 300 ml glass bottles and capped. The beverage was cooled to below 32° C. within 30 minutes.
  • this type of “Hot” Spiced Cider Juice Beverage is consumed warm to perceive the desired effect.
  • the beverage can also be consumed cold and offers a pleasant warming sensation.
  • a low-calorie functional carbonated soft drink has been prepared by utilizing the following formulation: Syrup Ingredient Weight to Volume Potassium Benzoate 2.10 g Sucralose 1.20 g Acesulfame-K 0.35 g Citric Acid 12.00 g Vitamin A Palmitate 0.15 g Ascorbic Acid 0.03 g Vitamin E Acetate 0.02 g Grapefruit Flavor 0.03 g Spray dried powder of the invention (Example 5) 0.18 g Natural flavor Sugar Top Notes 0.12 g Water QS Total 1000.00 ml Beverage Preparation
  • a dry blended mixture flavor was prepared according to the following composition: Salt 20.00% MSG 5.00% Ribonucleotide 0.20% Sugar 10.00% Yeast Extract Powder 10.00% Chilli Powder 3.00% Onion Powder 2.00% Garlic Powder 2.00% Tomato Powder 5.00% Whey Powder 42.30% Paprika Oleoresin 0.08% Neobee 0.22% Inventive composition of Example 1 0.20% 100.00%
  • This dry blended mixture was dispersed evenly at a rate of 7% onto unsalted potato crisps.
  • the invention's chips were founded to have a smoother, more rounded heat effect, than chips flavored with a dry blended mixture flavor having the same composition but not the invention's composition.

Abstract

The present invention relates to a flavor and skin sensation composition providing a hot or warming sensation upon consumption or application, respectively. The composition comprises a hot, warming component, a cooling component and a bitter component. In an embodiment, the composition further comprises an acid component. The composition provides a clean hot taste free of oily or earthy off-notes. Consumers prefer the composition over hot, warming compositions comprising essentially natural extracts.

Description

    CROSS-REFERENCE TO RELATED APPLICATION(S)
  • This application is a continuation of International application PCT/IB2006/051102 filed on Apr. 11, 2006, the entire content of which is expressly incorporated herein by reference thereto.
  • TECHNICAL FIELD
  • The present invention relates to the field of flavors and fragrances. In particular, the present invention relates to a flavor or skin sensation composition, to the use of a hot component, a cooling component, a bitter component and optionally an acid, to prepare a flavor or skin sensation composition and to food or body care products comprising the composition.
  • BACKGROUND OF THE INVENTION
  • The particular sensations mediated by the trigeminal nerve, such as cooling, warming, pungent and salivating are becoming more appreciated by consumers in food, body care and perfumed products. These trigeminal compounds are capable of providing unique characteristics to a large variety of foods and they are even perceived on the skin of the body. Accordingly, European patent application EP 1 121 927 A2, discloses a composition causing different skin sensations, the composition comprising a cooling sensate, a warming sensate and a tingling sensate.
  • Today, the compounds providing different trigeminal sensations are often found in natural extracts, such as oleoresins, in which high concentrations of these compounds are present. Natural extracts as such, however, often entail off-notes, oily organoleptic properties, or otherwise disturbing gustative characteristics and it is therefore an objective to provide a trigeminal sensation devoid of off-notes, sulfury effects and oily, heavy notes.
  • In particular, it is an objective of the present invention to provide a hot, warming trigeminal sensation devoid of off-notes as present in many natural extracts or even pure compounds. In other words, the present invention aims at providing an ingredient suitable for foods but also for topically administered body care products, such as shampoos and lotions, the ingredient providing a clean, warming trigeminal sensation substantially free of undesired off-notes typically associated with natural extracts, such as the black pepper extracts (spicy, earthy off-note) or mustard oil (pungent sulfury effect), for example.
  • Capsaicin, naturally present in various plant species of the Capsicum gender, is a well-known compound providing a strongly warming, hot trigeminal sensation and would thus be ideally employed in compositions providing a warming sensation to a food product. However, the use of capsaicin and its derivatives is limited by the fact that it may cause skin irritations. What is more, capsicum oleoresin has a pungent and oily off-note, which further puts a hindrance to its use in foods or body care products.
  • SUMMARY OF THE INVENTION
  • Therefore, the present invention now provides a hot, warming effect devoid of oily off-notes and skin-irritation effects typical for capsaicin. In particular, it provides a flavor or skin sensation composition providing a clean, hot trigeminal effect while reducing the amount of capsaicin present in the composition. The present invention further provides ingredients synergistically interacting with hot compounds in a way that the hot intensity is increased, in order to reduce the amount of hot, warming ingredients in a flavor composition.
  • Remarkably, the present inventors found that by preparing a composition comprising at least a hot component, a cooling component and a bitter component, a clean hot and/or warming sensation was provided, which is devoid of oily off-notes and further undesired characteristics. The sensation was particularly useful, clean and positively evaluated in food products, oral care and body care products.
  • Accordingly, the present invention provides, in a first aspect, a flavor or skin sensation composition comprising, a hot component, a cooling component, a bitter component and optionally an acid component.
  • In a second aspect, the present invention provides the use of a composition according to the invention, to prepare a flavor, perfume or skin sensation composition.
  • In a third aspect, the present invention provides the use of a composition according to the invention, to provide a hot flavor to a food product.
  • In a fourth aspect, the invention provides a method to confer, enhance, improve or modify the hot and clean taste to a food product, the method comprising the steps of adding to the food product a flavor composition according to the invention.
  • In further aspects, the invention provides a food product, an oral care product, a pharmaceutical product and a body care product comprising the flavor or skin sensation composition of the invention.
  • BRIEF DESCRIPTION OF THE DRAWING
  • In the figures,
  • FIG. 1 shows a comparison of the taste profiles of four hot ingredients, including the composition of the present invention (according to Example 1), from sugar-free hard-boiled candy application perceived by trained panelists. Statistically significant at 99% (**) and 99.9% (***) level of confidence.
  • FIG. 2 shows comparison of the hot intensity, flavor intensity and overall liking of sugar-free hard-boiled candy application comprising (A) the hot composition of the present invention (according to Example 1), and, (B) capsicum oleoresin as perceived by trained panelists at iso-hot intensity. Statistically significant at 99% (**) level of confidence.
  • DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
  • The composition of the present invention comprises a hot component, a cooling component, a bitter component, and optionally an acid component.
  • Preferably, the hot taste is a hot, clean taste if evaluated by a skilled panel of experienced tasters and has significantly reduced off-notes and oily organoleptic properties if compared to equally hot compositions based on natural extracts alone or other compositions than those of the present invention. Significantly reduced preferably refers to statistically significance at a confidence level of at least 90% and established with a panel of at least 15 tasters.
  • Accordingly, the present invention provides a composition comprising a hot component, a cooling component a bitter component and optionally an acid component. For example, the present invention provides a composition comprising a hot component, a cooling component and a bitter component. Preferably, the present invention provides a composition comprising a hot component, a cooling component, a bitter component and an acid.
  • The hot component is an ingredient, which provides a hot, warming sensation when brought into contact with the oral cavity or the skin. In particular, the hot component provides a hot, warming sensation mediated by the trigeminal nerve.
  • Examples of ingredients typically used in the food and oral care industry that can serve as hot component for the purpose of the invention include piperine, pelargonyl vanillyl amide, vanillyl butyl amide, vanillin butyl ether, eugenol, gingerol, polygodial, shogoal, galangal acetate, capsaicin(N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide and/or (6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide), capsaicin analogues and mixtures comprising two or more of these. Preferably, the hot component consists of 5-90% of capsicum oleoresin, and 10-95% of at least one other hot ingredient. Generally, most of the compounds mentioned above are present in natural extracts, which can directly be used for working the present invention, such as black pepper extract, mustard oil, ginger oleoresin, jambu oleoresin, capsicum oleoresin, Japanese pepper extract, chilli pepper extract, Tasmanian pepper extract, for example. Other examples of hot, warming compounds are disclosed in European patent application EP 1 121 927 A2, in particular in claim 6 of this reference, which is enclosed herein.
  • Similarly, the cooling component is preferably a purified compound, but may also be provided in the form of an extract, which provides, when brought in contact with the skin or oral cavity, a cooling sensation, which is mediated by the trigeminal nerve.
  • In a preferred embodiment, the cooling component is selected from the group consisting of menthol, menthyl succinate, menthyl lactate, p-menthane-3,8-diol, 8-p-menthen-3-ol (COOLACT P®, Takasago), 3-(3′-P-menthanyloxy)-1,2-propanediol (COOLANT AGENT 10®, Takasago), menthone glycerol ketal (FRESCOLAT® MGA, Haarmann & Reimer), 2-(1-methylpropyl)-1-cyclohexanone (FRESKOMENTHE®, Givaudan), N-ethyl-3-P-menthanecarboxamide (WS-3, Millennium Specialty Chemicals), aspartic acid, N-(4-hydroxy-3-methoxybenzyl)nonanamide, 5-[5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one, 6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, 2-isopropyl-N,2,3-trimethylbutanamide (WS-23, Millennium Specialty Chemicals), and, 7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol, 3-menthyl-3,6-dioxaheptanoate, 3-menthyl methoxyacetate, 3-menthyl-3,6,9-trioxadecanoate, 3-menthyl-(2-hydroxyethoxy)acetate, menthyl-11-hydroxy-3,6,9-trioxadecanoate, 3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one (cubebol, Firmenich SA, (3S,5S,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one (cubebol, Firmenich SA), 2,3-dihydroxypropyl(1R,2S,5R)-2-isopropyl-5-methylcyclohexane carboxylate (WS-30), (3S,5S,6S,9R)- or (3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one (FRESHONE®, Firmenich), (1R,2S,5R)-N-(tert-butyl)-2-isopropyl-5-methylcyclohexanecarboxamide (WS 14) and mixtures comprising two or more of these. Trivial names and suppliers of the compounds given above are indicated in brackets.
  • Cooling agents such as those mentioned above are commercially obtainable and their synthesis is well-known to the skilled person. Some of the above and further cooling agents are disclosed to the skilled person, for example in H. R. Watson, Flavor: Its Chemical, Behavioral and Commercial Aspects Apt, C. M. Ed. Westview; Boulder Colo.© (1977), 31-50. This reference comprises a list of about 1200 cooling and/or minty compounds, including WS compounds, developed by the Wilkinson-Sword company.
  • The bitter component is a compound or, more generally, an extract having bitter organoleptic properties. Bitterness is one of five recognized basic tastes (besides sweet, salty, sour and umami) and is mediated by taste buds at the back of the tongue. It can readily be attributed to compounds, ingredients, for example. In a preferred embodiment of the invention, the bitter component is selected from bitter triterpenes, glucosides of monoterpenes, sesquiterpenic lactones, humulone, lupulone, flavonones, quinines, and mixtures of these. Examples for bitter plant extracts include Quassia extract (also called bitter ash extract, FEMA No. 2971), quinquina extract, chamomile oils (FEMA No. 2272 to 2274), gentian root extract (FEMA No. 2506), hops extracts and oils (FEMA No. 2578 to 2580, artichoke leaves oil, just to mention a few.
  • In a preferred embodiment, the composition of the present invention further comprises an acid. Preferably, the acid is food-grade and hence suitable for human consumption. Preferably, the acid is a C2-C8, more preferably a C2-C6 organic acid. Examples of suitable acids are citric acid, acetic acid, succinic acid, pyruvic acid, lactic acid, propionic acid, malonic acid, oxalic acid, amongst many others. Of course, inorganic acids which are acceptable for human consumption may be used, equally, for example, HCl, H3PO4 (phosphoric acid), H2SO4 (nitric acid), etc.
  • Besides the compounds and extracts mentioned above, many others may equally be used instead or in addition in the composition of the invention. The skilled person, for example the skilled aromatician, flavorist or perfumers, is aware of a huge number of compounds and extracts, in particular natural extracts that contain hot and warming, cooling and/or bitter active principles and can select these as desired, for example according to the product (food, body care, perfumed) to which the composition is added.
  • In an embodiment of the present invention, any or all of the hot component, the cooling component and/or the bitter component, if present, is/are present in the form of a natural extract. Of course, the present composition may comprise both, natural extracts and isolated, for example chemically synthesised compounds. Accordingly, in an embodiment, any of the hot component, and/or the bitter component, if present, is/are present in the form of a natural extract.
  • Natural extracts comprise extracts made by any extraction method and include aqueous extracts, alcohol extracts, essential oils, supercritical fluids extract, hydrodistillated extract, for example.
  • In a further embodiment of the present invention, any or all of the hot component, the cooling component and/or the bitter ingredient, if present, is/are present in the form of isolated compounds. Preferably, the cooling component and the acid are present in the form of pure, isolated compounds, or solutions with defined quantity of the isolated compound, for example.
  • Many of these compounds, extracts, and other flavoring ingredients, are listed in reference texts such as in the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of similar nature such as Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press or Synthetic Food Adjuncts, 1947, by M. B. Jacobs, van Nostrand Co., Inc. Another book of reference listing food ingredients and extracts from which the components of the present invention may be selected is the “Allured's Flavor and Fragrance Materials”, 1999, Allured Publishing Corporation, Carol Stream, USA, which is usually up-dated annually and which lists flavors and ingredients together with FEMA numbers and suppliers. Ingredients disclosed on the text-books may be useful for selecting the components of the purpose of the present invention and are thus incorporated herein by reference.
  • Furthermore, the composition of the present invention preferably comprises at least one solvent, or a mixture of solvents, to dissolve the different components of the composition according to the invention. Solvents of current use for the preparation of a flavoring formulation are also well known in the art and the solvent is most of the time part of a flavoring composition. Solvent currently used in this framework include for instance benzyl alcohol, propylene glycol, triacetine, neobee, vegetable oils, ethanol or limonene. A mixture of solvents may be useful to dissolve hydrophobic and hydrophilic components in the same solution. For example, the components of the present invention may be is a solution comprising 20-95%, preferably 40-90%, more preferably 50-85% of solvent. In the context of the present invention, percentages are percentages by weight, unless otherwise indicated. Similarly, if proportions are indicated as parts, parts of weight are meant.
  • The composition of the invention may further comprise other ingredients typically used in flavor compositions, for example. In particular, the composition may comprise further flavors. The composition may also comprise adjuvants that allow the composition to meet technical requirements, such as stability or tonality persistence. Today, the range of products types and product formulations that are flavored has become so extensive and subjected to frequent changes that an approach made on a product-by-product basis and on the definition for each case of the adjuvants that can be used is impractical. This is why a list of adjuvants currently used in flavoring formulations is not given here. However, a skilled person in the art, for example a flavorist is capable of choosing these ingredients as a function of the product to be flavored and of the nature of the flavoring ingredients contained in the formulation.
  • According to a preferred embodiment the composition of the invention further comprises a lift enhancer. Lift enhancers are adjuvants capable of increasing the volatility of the other flavors or compounds of the composition of the invention, preferably without inferring or contributing to the flavor or other organoleptic properties of a flavor composition. Examples of lift enhancers belong to various chemical groups and include alcohols, aldehydes, ketals, esters, ethers or sulfur compounds, for example. Examples for lift enhancers typically used in industry are ethyl acetate, acetaldehyde, ethanol, acetal, acetone, butyraldehyde, propionaldehyde, dimethylsulfide, ethyl formate, propylmercaptan, butylmercaptan, methylethylcetone.
  • In a preferred embodiment, the composition of the present invention comprises 0.5-60% by weight of a hot component, 0.5-60% of a cooling component, 0.05-50% of a bitter component and optionally 0-60% of an acid component or acid and 0-40% of a lift enhancer.
  • For example, the composition comprises 1-50% of a hot component, 1-50% of a cooling component and 0.1-20% of a bitter component. In another example, the composition comprises 1-50% of a hot component, 1-50% of a cooling component, 0.1-20% of a bitter component and 1-50% of an acid component.
  • Preferably, the composition comprises 2-40% of a hot component, 2-40% of a cooling agent, 0.2-20% of a bitter compound and 2-40% of an acid. Even more preferably, the composition comprises 4-30% of a hot component, 4-30% of a cooling agent, 0.5-15% of a bitter compound and 4-30% of an acid. Preferably, these compositions comprises 0.5-10% of a lift enhancer.
  • The above percentages refer to the amount of plant extracts as concerns the hot and the bitter component, because hot and bitter principles are mainly commercialized in the form of extracts. The percentages of cooling agent and acid, however, are valid for pure, isolated compounds, because these components are generally commercialized as pure compounds, or solutions with known dilution of the active principle, for example the cooling agent. Furthermore, these percentages do not consider the amounts of other ingredients, such as solvents and adjuvants or other flavors, possibly being present in a flavor composition, but only refer to the part contributing to enhance a warming sensation given by combination of hot component, cooling agents, as well as an acid and/or a bitter component, and, optionally, a lift enhancer.
  • The composition of the invention can be made by simply mixing all components of the invention with a solvent at room temperature, preferably at the weight-ratios mentioned above.
  • In an aspect, the present invention provides the use of a composition according to the invention to prepare a flavor or a skin sensation composition.
  • In a further aspect, the present invention provides of a composition according to the invention to provide a hot flavor to a food product.
  • In an aspect, the present invention provides a method for imparting a hot taste to a food product, the method comprising the steps of adding to the food product the composition of the present invention.
  • In the above uses and method, the composition of the invention may be used directly as it is or added to food products as discussed below.
  • In an aspect, the present invention provides a food product comprising the composition of the present invention. The composition of the invention may directly be added to a food product at the stage where flavors are generally added. If convenient, the liquid composition may be encapsulated in a matrix, such as a carbohydrate, phospholipid, or protein matrix, such as a gelatin matrix, for example, or any bioactive matrix, in order to provide a shelf-stable, dry form of the flavor or skin composition of the invention.
  • Therefore, in an embodiment, the present invention provides a delivery system comprising the composition of the present invention. Preferably, the delivery system is in the form of a particulate composition and/or a powder. For example, the composition may be encapsulated following standard procedures in spray-dried powders. For example, the composition may be encapsulated in a matrix, which is in a glassy state at room temperature. For example, the composition of the invention may be encapsulated in rod-like granules the preparation of which is disclosed in U.S. Pat. No. 4,707,367.
  • The composition of the invention may be used in liquid food products and/or in products that are solid. Accordingly, in a preferred embodiment of the invention, the food product is selected from the group consisting of a confectionery product, a bakery product, a beverage carbonated or non-carbonated, a alcoholic drink, a dairy product, a soy product, a soup, a dressing, a gravy, a condiment, a sauce, and a dip, a snack, noodles, chips, meat and fish, for example.
  • Examples for confectionery products include chocolates, candies, chewing gums, for example.
  • In an aspect, the present invention provides an oral care product according to the invention. For example, the product may be a toothpaste, a tooth-gel, a mouthwash.
  • In an aspect, the present invention provides a pharmaceutical product comprising the flavor composition according to the invention. Examples of such products are syrups, drugs provides in tablets or capsules.
  • In another aspect, the present invention provides a body care product comprising the composition of the present invention. For example, the composition of the invention is put in a lip balm, a shampoo, a soap, a cream, and/or a body lotion, a perfume. Given that the composition comprises a hot component and a cooling component, human skin will be susceptible to make a unique sensational experience when getting in contact with the composition of the present invention.
  • The products of the present invention, such as foods, beverages, pharmaceuticals, oral care and body care products may be prepared following known procedures and the composition of the invention may be added in liquid or encapsulated particulate form, depending on the product, to the product at the same time as flavors or perfumes are typically added.
  • EXAMPLES
  • The following examples further describe and demonstrate embodiments within the scope of the present invention. These examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention as many variations thereof are possible without departing from the spirit and scope.
  • Example 1
  • Hot Flavor and Skin Sensation Composition
  • A composition providing hot, warming trigeminal properties was prepared according to Table 1 below. All components were mixed under stirring in food-grade solvents. The composition, when tasted as such, provided a strong and clean hot, warming taste. Earthy, oily off-notes and the peppery note typical for piperine were not detected or strongly reduced.
    TABLE 1
    Components for hot trigeminal composition
    Ingredient Characteristics Origin % by weight
    Piperine Hot component Aldrich1), FEMA2) No. 8.1
    2909
    Menthol nat. Cooling agent Aldrich, FEMA No. 5.5
    2665
    Quassia Bitter component Chart4), FEMA No. 0.2
    extract3) 2971
    Acetic acid Acid Aldrich, FEMA No. 4
    2006
    Ethyl acetate Lift enhancer Aldrich, FEMA No. 2
    2414
    Neobee Solvent Stepan5) 40.1
    Triacetin Solvent Aldrich, FEMA No. 40.1
    2007

    1)www.sigmaaldrich.com;

    2)FEMA: Flavor and Extract Manufacturer's Association of the US, Suite 925, 1620 I Street, N.W, Washington, D.C. 20006;

    3)also called bitter ash extract;

    4)www.chartcorp.com

    5)www.stepan.com
  • Example 2
  • Further Hot Flavor and Skin Sensation Composition
  • A further hot flavor and skin sensation composition was prepared with the same procedure as in Example 1, but with the components indicated in Table 2 below. The composition, when tasted as such, provided a strong and clean hot, warming taste. Earthy and oily off-notes typical for capsaicin were not detected.
    TABLE 2
    Components for hot trigeminal composition
    Ingredient Characteristics Origin % by weight
    Capsicum Hot component Penta6), FEMA No. 1.3
    oleoresin 2234
    Menthol nat. Cooling agent Aldrich, FEMA No. 5.5
    2665
    Quassia extract3) Bitter component Chart4), FEMA No. 0.2
    2971
    Acetic acid Acid Aldrich, FEMA No. 3
    2006
    Ethyl acetate Lift enhancer Aldrich, FEMA No. 2.5
    2414
    Neobee Solvent Stepan5) 43.75
    Triacetin Solvent Aldrich, FEMA No. 43.75
    2007

    6)Penta Manufacturing, Livingston, USA
  • Example 3
  • Sugar-Free Hard Boiled Candy Comprising the Hot Flavor Composition
  • For different samples of sugar-free hard boiled candies were prepared with different hot, warming trigeminal ingredients according to the procedure below.
  • Isomalt (100 g) and water (30 g) were mixed and heated to 160-165° C. in a copper pan. At 165° C., the copper pan was removed from the gas frame and placed in a warm water bath (40° C.). After a few seconds, the copper pan was removed and the temperature checked. When temperature reached 135° C., the flavoring system according to Table 3 was added. The mixture comprising isomalt and was further complemented with 1% of an aqueous solution containing Aspartame (10%) and Acesulfame-K (5%). Thereafter, hot flavors were added according to Table 2 below, in which hot extracts commercially obtained were diluted in the same proportions as in Example 1 (80.2% of solvents) to provide flavor solutions allowing easy handling and dosing. The cooked mass was then poured at ambient temperature (at less than 40% relative humidity) in appropriate Teflon molds.
    TABLE 3
    Flavor components of different samples of sugar-free hard-boiled candy
    Flavor (19.8%) in Origin and Dosage in
    solvent Code candy (w/w)
    Black pepper Chart, FEMA 0.05%
    extract1) 2846
    Mustard oil Fleurchem7) 0.05%
    FEMA 2034
    Capsicum Penta, 0.05%
    oleoresin FEMA 2234
    Hot Mix Example 1 0.05%

    7)Fleurchem Inc., Flemington, USA

    Sensory Evaluation of Composition of the Invention In Candy
  • The different sugar-free hard-boiled candies obtained in Example 3 were evaluated by 20 trained panelists in one tasting session and tested two samples each, which were presented in a blind and randomized manner. The intensity of each attribute (hot, pungent, spicy, peppery, oily, off-notes and overall intensity) was evaluated on a 0 to 10 linear scale from absent to strong. For data analysis, a Student's t-test was performed to identify differences between the two samples.
  • The result can be seen in FIG. 1. The composition of the invention (“hot mix”) provides a cleaner hot taste compared to single ingredient like a capsicum oleoresin with its pungent and oily off-notes, black pepper extracts with their typical peppery spicy earthy character, or a mustard oil with its pungent sulfury effect. (FIG. 1). In addition, the hot intensity with the composition of the invention is stronger than with black pepper extract or mustard and nearly as strong as that of capsicum oleoresin. Therefore, the blend of the present invention is capable of partly replacing capsaicin content (capsaicin present in capsicum oleoresin, for example).
  • Example 4
  • Preparation of Sugar-Free Hard-Boiled Candy of Iso-Hot Intensity
  • The purpose of this example is to prepare sweets based on different hot trigeminal ingredients at iso-hot intensity (having the same hot intensity as perceived by a panel) to compare gustative properties other than hotness.
  • Accordingly, the same procedure as in Example 3 was performed to prepare sugar-free hard boiled candy, with the difference that other quantities of hot ingredients were added, as shown in Table 4 below. In addition, a lemon-flavor was added at 0.06% to the present candies. For the composition of the invention (hot mix), the composition of Example 1 (Table 1) was used. For comparison, a 20 wt. % solution of capsicum oleoresin was used in the same solvents as in Example 1.
    TABLE 4
    Flavor components of different samples of sugar-free hard-boiled candy
    Dosage in
    Origin and Candy
    Flavor Code (w/w)
    Lemon Firmenich 0.060%
    Hot Mix Example 1 0.030%
    Lemon Firmenich 0.060%
    Capsicum Fleurchem 0.013%
    oleoresin FEMA 2234

    Sensory Evaluation of Hard-Boiled Candy at Iso-Hot Intensity
  • The trained panelists participated in one tasting session and tested the two samples above each (present invention and capsicum oleoresin), which were presented in a blind and randomized manner. The intensity of each attribute was evaluated on a 0 to 10 linear scale from hot intensity, flavor intensity and overall liking. A Student's t-test was performed to identify significant differences between the two samples.
  • Sensory results are indicated in FIG. 2. It can be seen that hot intensity was virtually the same (iso-hot intensity). At iso-hot intensity, the composition of the present invention provided a significantly (p<0.1) stronger flavor intensity and over-all liking than candies comprising capsicum oleoresin. Therefore, the composition present invention is suitable to replace capsicum oleoresin to provide hot, warming trigeminal properties while being organoleptically preferred by consumers.
  • Example 5
  • Preparation of Flavored Compressed Tablets Comprising the Composition of the Invention
  • An encapsulated form of the composition of the present invention was prepared according to standard procedures. Once, a glassy matrix of carbohydrates comprising 9% of a flavor composition according to Example 1, but at double concentration (hot composition: 39.6%; solvents: 61.4%) was prepared according to the procedure outlined in U.S. Pat. No. 4,707,367 to obtain a particulate composition of rod-like granules.
  • Secondly, a spray-dried powder of encapsulated flavor composition was prepared in a carbohydrate matrix (50% maltodextrin, 40% modified starch) with 20% load of the same concentrated composition as for the rod-like granules obtained above. In this way, an encapsulate of the composition of the invention having the double flavor load of the spray-dried encapsulate obtained above was prepared.
  • Sugar-free, cinnamon-flavored chewable tablets were prepared in that crystalline sorbitol (97.9%), aspartame (0.05%), acesulfame-K (0.05%) and magnesium stearate (2%) were mixed for 5 minutes in a Turbula (WAB AG, Basel, Switzerland). The flavoring system was added with dosages indicated in Table 5. After additional blending (1 minute), tablets of 1.20 g weight and 20 mm diameter were prepared using a Specac (Portmann Instruments, Biel, Switzerland) at a 0.40-ton compression pressure.
    TABLE 5
    Encapsulated flavors for compressed tablets comprising the composition of the
    invention
    Flavor load in Dosage of
    granules/ granules/powder
    Sample Flavor Origin powder in tablet
    1, 2 Cinnamon1) Firmenich SA, 17%  1.9%
    (DURAROME ®) Geneva, Switzerland
    1 Composition Rod-like granules, 9% 0.75%
    of the see above
    invention
    2 Composition of Spray-dried powder, 20% 0.34%
    the see above
    invention

    1)Encapsulated cinnamon flavor similar to rod-like granules obtained above.
  • The cinnamon and hot-flavored tablets comprising the composition of the invention in different encapsulated forms were compared by trained panelists according to the procedure of Examples 3 and 4. Tablets were sucked for 3 minutes while intensity was recorded at minutes 0.5, 1, 2 and 3. After 1 minute, sample 1 started to show higher hot intensity, which difference increased in the following minute to result in a significantly higher hot intensity with tablets comprising rod-like granules encapsulating the composition of the invention.
  • Example 6
  • Sugar-Free Chewing Gum Comprising the Encapsulates of the Composition of the Invention
  • Sugar-free chewing gums were prepared by the following standard procedure: Crystalline sorbitol, acesulfame K and aspartame were blended in a Turbula blender. Half the blend was mixed with a pre-warmed Sierra gum base (Cafosa) in a Winkworth sigma-blade mixer at 50-55° C. for 2 minutes. The remaining powder blend was then added along with a humectant syrup (LYCASIN® 80/55, SORBIT®, glycerin) and mixed for a further 7 minutes. Finally, the flavoring system was added and mixed for one minute at the dosages indicated in Table 6 below.
    TABLE 6
    Flavors in chewing gums comprising the hot, warming
    composition of the invention
    Dosage
    Flavor of liquid/
    load in granules/
    liquid/ powder in
    granules/ chewing
    Sample Flavor Origin powder (%) gum (%)
    1, 2 Liquid NOVAMINT ® 100 1
    peppermint from Firmenich
    flavor SA, Geneva
    1 Rod-like Example 5 9 0.52
    granules of
    composition of
    the invention
    2 Spray dried Example 5 20 1.15
    powder with
    composition of
    the invention
  • Chewing gums with a clean, hot taste without earthy or oily of-notes were obtained.
  • Example 7
  • Toothpaste Comprising the Composition of the Invention
  • About 5 kg of toothpaste are prepared following the protocol and ingredients given below:
  • Part 1: Solution of Carboxy methyl cellulose
    Ingredients Amount Percent
    Carboxy Methyl Cellulose 7MXF = CMC  60.00 grams 5.66%
    (Supplier: Hercules BV Aqualon Div.)
    Glycerin 1000.00 grams 94.34%
    Total 1060.00 grams 100.00%

    Procedure:
  • Mix CMC and glycerin, using a laboratory mixer at high speed for 5-10 minutes. Let the solution hydrated for 30 minutes
  • Part 2: Solution of Powder Ingredients
    Ingredients Amount Percent
    Distilled Water 1500.00 grams 50.74%
    Saccharin Sodium 10.00 grams 0.34%
    Sodium Benzoate 5.00 grams 0.17%
    Sodium Fluoride 16.00 grams 0.54%
    (Supplier: Riedel de Haen AG - Germany)
    Polyethylene Glycol 1500 150.00 grams 5.07%
    Titanium Dioxide 25.00 grams 0.85%
    Sorbitol 70 1250.00 grams 42.29%
    (Supplier: Neosorb 70/70 Roquette Freres)
    Total 2956.00 grams 100.00%

    Procedure:
  • Pour the dry ingredients (as listed) into water using mixer Turrax for 5-10 minutes. Add Sorbitol liquid, mix 3 minutes. Add Part 1 in Part 2, and mix for 10-15 minutes.
  • Part 3: Solution of Sodium lauryl sulfate
    Ingredients Amount Percent
    Sodium Lauryl Sulphate 75.00 grams 6.38%
    (Texapon K12 Supplier: Cognis
    Gmbh - Germany)
    Distilled Water 200.00 grams 17.02%
    Sorbosil TC 15 600.00 grams 51.06%
    (Supplier: Crosfield Limited)
    Sorbosil AC 77 300.00 grams 25.53%
    (Supplier: Crosfield Limited)
    Total 1175.00 grams 100.00%

    Procedure:
  • Mix gently Sodium lauryl sulfate with water and let set for minimum 3 hours, better overnight. Pour the mix of Part 1 and Part 2 into the pan of Stephan Mixer and let set for 2-3 hours, or until the air bubbles disappear. Add Sorbosil (TC 15 and AC 77) and mix under vacuum (50-60 mBar) for 30 minutes. Open the pan and add solution of Sodium lauryl sulfate. Mix under vacuum (50-60 mBar) for 5 minutes.
  • At the end, flavors are added to the toothpaste. Accordingly, 1.5% of liquid mint flavor (NOVAMINT®, Firmenich SA, Geneva) and 1.5% of the composition of the invention obtained in Example 2 are mixed with the toothpaste to obtain an oral care product providing a hot, warming sensation.
  • Example 8
  • Beverage Applications Using an Invention's Composition
  • A juice-containing beverage was prepared by blending the following ingredients until uniform.
    Ingredient % By Weight
    Apple Juice Concentrate, 68° Brix 16.910%
    Natural Apple Flavor 0.150%
    Natural Allspice Flavor 0.050%
    Natural Cinnamon Flavor 0.005%
    Spray dried powder of the 0.025%
    invention (Example 5)
    Water 82.860%
    Total 100.000%
  • The resulting beverage was subsequently heat processed at 90° C. and held at this temperature for one minute. After the hold time, the beverage was packaged into 300 ml glass bottles and capped. The beverage was cooled to below 32° C. within 30 minutes.
  • Generally, this type of “Hot” Spiced Cider Juice Beverage is consumed warm to perceive the desired effect. By the addition of the invention's composition, the beverage can also be consumed cold and offers a pleasant warming sensation.
  • Example 9
  • Beverage Applications Using an Invention's Composition
  • A low-calorie functional carbonated soft drink has been prepared by utilizing the following formulation:
    Syrup
    Ingredient Weight to Volume
    Potassium Benzoate 2.10 g
    Sucralose 1.20 g
    Acesulfame-K 0.35 g
    Citric Acid 12.00 g
    Vitamin A Palmitate 0.15 g
    Ascorbic Acid 0.03 g
    Vitamin E Acetate 0.02 g
    Grapefruit Flavor 0.03 g
    Spray dried powder of the invention (Example 5) 0.18 g
    Natural flavor Sugar Top Notes 0.12 g
    Water QS
    Total 1000.00 ml

    Beverage Preparation
  • To prepare a 300 ml of finished beverage pour 50 ml of above-prepared beverage syrup and 250 ml carbonated water into a carbonated beverage bottle. Cap the bottle and gently shake to mix.
  • When this beverage was compared with one containing capsaicin instead of the invention's composition, the overall flavor of the invention's beverage was improved. The flavor was cleaner with less off-notes and the flavor complements the beverage's grapefruit profile better than with capsaicin.
  • Example 10
  • Savory Applications Using an Invention's Composition
  • A dry blended mixture flavor was prepared according to the following composition:
    Salt 20.00%
    MSG 5.00%
    Ribonucleotide 0.20%
    Sugar 10.00%
    Yeast Extract Powder 10.00%
    Chilli Powder 3.00%
    Onion Powder 2.00%
    Garlic Powder 2.00%
    Tomato Powder 5.00%
    Whey Powder 42.30%
    Paprika Oleoresin 0.08%
    Neobee 0.22%
    Inventive composition of Example 1 0.20%
    100.00%
  • This dry blended mixture was dispersed evenly at a rate of 7% onto unsalted potato crisps. On evaluation, the invention's chips were founded to have a smoother, more rounded heat effect, than chips flavored with a dry blended mixture flavor having the same composition but not the invention's composition.

Claims (10)

1. A flavor or skin sensation composition comprising a hot component, a cooling component, a bitter component and optionally an acid component.
2. The composition according to claim 2, which comprises 0.5-60% by weight of the hot component, 0.5-60% of the cooling component, 0.05-50% of the bitter component and 0-60% of the acid component.
3. The composition according to claim 1, in which the hot component agent is selected from the group consisting of piperine, pelargonyl vanillyl amide, vanillyl butyl amide, vanillin butyl ether, eugenol, gingerol, polygodial, shogoal, galangal acetate, capsaicin(N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide and/or (6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide), capsaicin analogs and mixtures comprising two or more of these.
4. The composition according to claim 1, in which the cooling component is selected from the group consisting of menthol, menthyl succinate, menthyl lactate, p-menthane-3,8-diol, 8-p-menthen-3-ol, 3-(3′-P-menthanyloxy)-1,2-propanediol, menthone glycerol ketal, 2-(1-methylpropyl)-1-cyclohexanone, N-ethyl-3-P-menthanecarboxamide, aspartic acid, N-(4-hydroxy-3-methoxybenzyl)nonanamide, 5-[5-(1,3-benzodioxol-5-yl)-1-(]-piperidinyl)-2,4-pentadien-1-one, 6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, 2-isopropyl-N,2,3-trimethylbutanamide, and, 7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol, 3-menthyl-3,6-dioxaheptanoate, 3-menthyl methoxyacetate, 3-menthyl-3,6,9-trioxadecanoate, 3-menthyl-(2-hydroxyethoxy)acetate, menthyl-11-hydroxy-3,6,9-trioxadecanoate, 3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, 2,3-dihydroxypropyl(1R,2S,5R)-2-isopropyl-5-methylcyclohexane carboxylate, (3S,5R,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, (3S,5S,6S,9R)-6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, (1R,2S,5R)-N-(tert-butyl)-2-isopropyl-5-methyl-cyclohexanecarboxamide and mixtures comprising two or more of these.
5. The composition according to claim 1, in which the bitter component is selected from the group consisting of bitter triterpenes, glucosides of monoterpenes, sesquiterpenic lactones, humulone, lupulone, flavonones, quinines, and mixtures comprising two or more of these.
6. The composition according to claim 1, in which the acid component is selected from the group consisting of citric acid, acetic acid, succinic acid, pyruvic acid, lactic acid, propionic acid, malonic acid, oxalic acid, HCl, H3PO4 and H2SO4.
7. A composition according to claim 1, further comprising a lift enhancer in an amount of up to 40% of the lift enhancer.
8. A food product comprising the flavor composition according to claim 1, wherein the food product is selected from the group consisting of an oral care product, a body care product and a pharmaceutical product.
9. A product comprising the flavor composition according to claim 1, wherein the product is selected from the group consisting of a confectionery product, a bakery product, a carbonated beverage, a non-carbonated beverage, an alcoholic drink, a dairy product, a soy product, a soup, a dressing, a gravy, a condiment, a sauce, and a dip, a snack, noodles, chips, meat, fish, chocolates, a candy, a chewing gum, a toothpaste, a tooth-gel, a mouthwash, a syrup, a drug provided in tablets or capsules, a lip balm, a shampoo, a soap, a cream, a body lotion and a perfume.
10. A method of preparing a flavor, perfume or skin sensation composition which comprises combining a hot component, a cooling component, a bitter component and optionally an acid component and a lift enhancer to prepare the composition.
US11/853,656 2005-04-15 2007-09-11 Hot flavor and skin sensation composition Abandoned US20080000614A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010139954A1 (en) * 2009-06-05 2010-12-09 Wei Edward Tak Treatment of eye discomfort by topical administration of a cooling agent to the external surface of the eyelid
EP2990080A1 (en) * 2014-08-28 2016-03-02 Henkel AG&Co. KGAA Oral and tooth care and cleaning agents for gum vitalisation
US11433037B2 (en) 2016-07-05 2022-09-06 Glaxosmithkline Consumer Healthcare Holdings (Us) Llc Oral dosage form containing a fast release exterior coating

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070036733A1 (en) 2005-08-12 2007-02-15 Takasago International Corp. (Usa) Sensation masking composition
JP5067529B2 (en) * 2006-12-13 2012-11-07 ライオン株式会社 Oral composition
US20100285178A1 (en) * 2007-11-15 2010-11-11 Nestec S.A. Production of food products with enhanced in mouth and mental refreshment
ES2425356T3 (en) * 2008-04-15 2013-10-14 Firmenich S.A. Sensory warmth composition
US9681678B2 (en) * 2011-04-01 2017-06-20 International Flavors & Fragrances Inc. Flavor composition containing flavone glycosides
JP5748626B2 (en) * 2011-09-21 2015-07-15 サンスター株式会社 Oral composition
JP6095364B2 (en) * 2012-12-28 2017-03-15 花王株式会社 Heating equipment
CN103300336B (en) * 2013-06-20 2014-07-30 松村辉 Essence of pickled Chinese cabbage and preparation method and application thereof
CA2994331C (en) 2015-07-31 2023-10-03 Delivra Inc. Transdermal formulations for delivery of capsaicinoids
US10517805B2 (en) 2015-12-31 2019-12-31 L'oréal Cosmetic compositions having mechanically activated warming enhancement

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0231051B2 (en) * 1983-10-03 1990-07-11 Lion Corp KORYOSOSEIBUTSU
US6159509A (en) * 1996-10-28 2000-12-12 Wm. Wrigley Jr. Company Method of making chewing gum products containing perillartine
US6322838B1 (en) * 2000-04-25 2001-11-27 Haarmann & Reimer Gmbh Mint and/or fruit flavor compositions
JP2003113019A (en) * 2001-09-28 2003-04-18 Lion Corp Skin care preparation
JP3759714B2 (en) * 2001-12-27 2006-03-29 株式会社資生堂 Itching, rough skin, sensitive skin and whitening agent by inhibiting production and release of stem cell factor
DE10226990A1 (en) * 2002-06-18 2004-03-18 Sanguibiotech Ag Topically applicable micro-emulsions with binary phase and active substance differentiation, their production and their use, in particular for supplying the skin with bioavailable oxygen
KR20050105461A (en) * 2003-02-13 2005-11-04 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 SKIN PREPARATION FOR EXTERNAL USE CHARACTERIZED BY CONTAINING SUGAR DERIVATIVE OF α,α-TREHALOSE
US20050261367A1 (en) * 2004-03-29 2005-11-24 Howard Murad Methods for treating dermatological and other health-related conditions in a patient

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010139954A1 (en) * 2009-06-05 2010-12-09 Wei Edward Tak Treatment of eye discomfort by topical administration of a cooling agent to the external surface of the eyelid
EP2990080A1 (en) * 2014-08-28 2016-03-02 Henkel AG&Co. KGAA Oral and tooth care and cleaning agents for gum vitalisation
US11433037B2 (en) 2016-07-05 2022-09-06 Glaxosmithkline Consumer Healthcare Holdings (Us) Llc Oral dosage form containing a fast release exterior coating

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CN101155522B (en) 2011-08-24
RU2007142200A (en) 2009-05-20
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AR053056A1 (en) 2007-04-18

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