KR20060086444A - Mixture with wintergreen odor and flavor - Google Patents

Abstract

The invention relates to a mixture of compounds having the sensory properties of wintergreen, to fragrance and flavoring compositions containing said mixture and to flavored and perfumed products containing said mixture, to a method of adding a wintergreen flavor, odor or note to (non-wintergreen) flavored or perfumed products. Further the present invention relates to the use of said mixture as an enhancement, or as complete or partial replacement for methyl salicylate, in particular in chewing gum, foods, dentifrices, mouthwashes and other orally consumable products. The mixture comprises or consists of dihydroanethole, o- anisaldehyde, 1,3-dimethoxybenzene, 2'-hydroxyacetophenone, and optionally 2-methoxyacetophenone.

Description

Mixture with Wintergreen Odor and Flavor}

The present invention relates to mixtures of compounds having the sensory properties of wintergreen, fragrance and flavor divergent compositions containing said mixtures and flavored and perfumed products containing said mixtures, (non It relates to a method for adding the flavor, aroma or note of wintergreen to a flavored or flavored product of wintergreen. The present invention further relates to the use of such mixtures, in particular, as adjuvant or complete or partial replacement of methyl salicylate in chewing gum, foods, dentifrices, mouthwashes and other oral ingestion products.

Methyl salicylate (2-hydroxybenzoic acid methyl ester) is a commonly used flavoring agent. It is a major component of the wittergreen oil obtainable by steam distillation from parts of plants, especially leaves. Methyl salicylate is also produced by esterification of salicylate with methanol.

The sensory properties (flavor and taste) of methyl salicylate are depicted as warm, sweet, phenolic wintergreens.

Methyl salicylate is a flavor and aroma compound commonly used to provide the sensory properties of wintergreens. It is used in perfumes, foods, beverages, candy, chewing gum, oral care products and the like. It is also used to enhance the flavor of mint flavored products, for example, products which are primarily seasoned by peppermint or spearmint oil.

Methyl salicylate is also used as an active ingredient in topically applied anesthetic ointments to promote relief of myalgia, arthritis and similar diseases. Salicylic acid derivatives, the most famous acetyl salicylic acid (known more as aspirin) have pharmaceutical properties such as analgesics, anticoagulants, antipyretics and antifungal activity. Such pharmaceuticals generally exhibit some toxicity. Methyl salicylate itself is known to be toxic at certain doses and above.

Products added with methyl salicylate have gained widespread consumer acceptance, but the use of such compounds with pharmaceutical properties and toxicity has the potential to be subject to government regulations that limit the bad reputation or use, or prohibit use entirely. It is dangerous.

In addition methyl salicylate is not stable in alkaline media. Instability in such alkaline media limits the number and type of compositions and products from which methyl salicylate can be successfully introduced.

The utility of the replacement compound for methyl salicylate will be quite high.

U.S. Patent 5,795,616 relates to the use of 2'-hydroxypropiophenone as a flavor component. More specifically, it relates to the use of 2'-hydroxypropiophenone as an adjuvant or complete or partial replacement of methyl salicylate in chewing gum, foods, dentifrices, mouthwashes and other oral ingestion compositions. Although this document describes the use of 2'-hydroxypropiophenone as a flavor and replacement for methyl salicylate, the best results are achieved when using a mixture of 2'-hydroxypyrophenone and methyl salicylate. . More preferred replacement amount of methyl salicylate is about 10-50 wt%.

WO 01/68044 discloses an oral composition comprising a ingredient which imparts a flavor of wintergreen and having an alkaline pH, wherein the ingredient imparting a flavor of wintergreen is 2'-hydroxypropiophenone.

To date no satisfactory non-salicylate substituents have been provided to replace methyl salicylates in fragrance and / or flavor divergent compositions.

The present invention provides a mixture MS having the sensory properties of wintergreen. Mixture MS comprises or consists of compounds A, B, C and D.

Optionally, the mixture MS is complete by adding a significant amount of compound E.

Mixture MS:

compound synonym CAS- # FEMA- # A 1-methoxy-4-propyl-benzene Dihydroanetol; p-propylanisole 104-45-0 2930 B 2-methoxybenzaldehyde o-anisaldehyde 135-02-4 - C 1,3-dimethoxybenzene Resorcinol dimethyl ether; m-methoxyanisole 151-10-0 2385 D 1- (2-hydroxyphenyl) -ethanone 2'-hydroxyacetophenone; o-acetylphenol 118-93-4 3548 E 1- (2-methoxyphenyl) -methanone 2'-methoxyacetophenone; Acetylanisole 579-74-8 -

A feature and one main advantage of the present invention is that the flavor, aroma or character of wintergreens in the fragrance and flavor divergent composition or the product flavored or flavored by the mixture MS according to the invention, preferably methyl salicylate and / or ethyl It is provided without the use of salicylate.

The fragrance and flavor divergent compositions according to the invention comprise organoleptically effective amounts of the mixture MS. Preferably such aroma or flavor divergent composition is (i) generated by the amount of the mixture present, or (ii) retains the flavor or aroma of the enhanced wintergreen.

The present invention further provides improved flavored or flavored products. The term "added product" in the present invention means a product which is prepared to be taken orally or at least taken orally.

The present invention provides the use of a mixture MS to enhance or replace methyl salicylate in the fragrance and flavor divergent compositions used in flavored or flavored products. When used as a substitute for methyl salicylate, the replacement may be partial or complete.

In one aspect of the invention the flavored product of wintergreens containing methyl salicylate as flavor or odorant is enhanced by the addition of the mixture MS. Preferably the weight ratio of methyl salicylate to mixture MS in the flavored or flavored product is about 10: 1 to 1:20, more preferably about 4: 1 to 1:10.

In an embodiment of the present invention the pH of the fragrance or flavor divergent composition or the flavored or flavored product is alkaline. This means that the pH reaches about 7.5 to about 12. In certain embodiments the pH is at least 7.5, preferably from about 8.5 to 10.5.

In one embodiment there is provided a method of reducing the amount of methyl salicylate in the aroma and flavor divergent composition of wintergreen. The method includes modifying the formulation of the savory product of wintergreen by replacing at least a portion of methyl salicylate with a mixture MS. In a preferred embodiment, all methyl salicylates are replaced.

Further aspects of the invention are set forth in the appended claims and will become apparent from further detailed description.

The present invention provides a non-salicylate mixture "hereinafter also referred to as mixture MS" which has a sensory profile very similar to methyl salicylate and can replace methyl salicylate. This causes the mixture MS to substitute methyl salicylate in any amount of the original content of methyl salicylate, depending on the application.

Mixture MS comprises or consists of compounds A, B, C and D and optionally compound E. Mixture MS is recognized as novel.

Preferably the amount of compounds A), B), C) and D) and the ratio of compounds A): B): C): D) in the mixture MS should be adjusted such that the mixture provides the flavor or aroma of wintergreen. .

The preferred weight of the compound in the mixture MS according to the invention is as follows.

compound synonym Parts by weight A 1-methoxy-4-propyl-benzene Dihydroanetol 5-80 B 2-methoxybenzaldehyde o-anisaldehyde 10-90 C 1,3-dimethoxybenzene m-methoxyanisole 100-500 D 1- (2-hydroxyphenyl) -ethanone 2'-hydroxyacetophenone 100-500 E 1- (2-methoxyphenyl) -ethanone 2'-methoxyacetophenone 0-200

Preferably the weight ratio of compound A: B: C: D: E in the mixture MS is about 5-80: 10-90: 100-500: 100-500: 0-200, more preferably about 10-40: 20 -70: 150-400: 150-400: 50-150.

The sensory properties of each of Compounds A through E are as follows (Leffingwell & Associates-Database, Flavor-Base Professional 2001, Tobacco Edition, GRAS & EC Flavor Chemicals Report):

compound Sensory properties A 1-methoxy-4-propyl-benzene Sweet, herbal, anise-like aroma and taste B 2-methoxybenzaldehyde Sweet and fragrant, floral, anise-like, cinnamon-like aroma, fragrant C 1,3-dimethoxybenzene Sweet, Flowery, Earthy, Root Beer, Chemical D 1- (2-hydroxyphenyl) -ethanone Sharp, Cherry-Almond-Hawthorn-Harse, Cinnamon, Naphthyl, Cherry Seed, Comarin, Phenolic, Tobacco, Honey E 1- (2-methoxyphenyl) -ethanone Herbal, Phenolic Wintergreen, Chemical, Medical, Turbid

Since none of the compounds A to D show the aroma or flavor of the wintergreen, it is surprising that mixing the compounds A to D produces a mixture with typical wintergreen flavor and aroma.

The sensory properties of the mixture MS and methyl salicylate according to the invention were evaluated at the same concentrations in the sweet water taste test, respectively. 500 mg each of the mixture MS and methyl salicylate according to the present invention was dissolved in 10 mL of ethanol. And 1 mL of this solution was dissolved in 100 mL of 5 wt% sugar aqueous solution.

The weight ratio of compound A: B: C: D in mixture MS is 20: 40: 250: 250.

Sensory characteristics were evaluated on a scale of 1 (very weak) to 10 (very strong), respectively, according to the following descriptors.

Descriptor Methyl salicylate Mixture MS Winter green 8 7 sweet 7 7 Medicinal 7 6 Phenolic 5 5 Shock 7 8 burglar 8 8

When compound E is added to the mixture consisting of compounds A to D, the sensory properties of the compound become more harmonious and closer to methyl salicylate.

When o-anisaldehyde is replaced by the same amount of p-anisaldehyde, the sensory properties of such a mixture can be described as more coumarinic, vanilla-like, green rakes, unlike typical wintergreens.

As described above, the fragrance or flavor divergent composition according to the invention will retain the flavor or aroma of (i) generated or (ii) enhanced wintergreen by the amount of the mixture. In a preferred embodiment the fragrance or flavor divergent composition according to the invention comprises methyl salicylate. In this case the ratio by weight of methyl salicylate: mixture of mixtures MS (A), B), C) and D)) is typically from 10: 1 to 1:20, preferably from 4: 1 to 1:10. to be.

A flavored or flavored product according to the invention comprises (i) mixture MS or (ii) aroma or flavor divergent composition (the composition itself comprising the mixture MS) according to the invention.

Preferably the product retains the flavor or aroma of (i) generated or (ii) enhanced wintergreen by the amount of the mixture MS.

In a preferred embodiment the flavored or flavored product according to the invention is chewing gum, toothpaste or mouthwash.

Preferred products according to the invention have from about 7.5 to about 12, especially if they do not comprise methyl salicylate.

The flavored product according to the invention contains about 0.05 to 5% by weight of mixture MS (mixture MS according to the invention). The flavored product according to the invention preferably comprises about 0.05 to 2% by weight of the mixture MS.

Depending on the needs of the individual, the product according to the invention may or may not contain methyl salicylate. In a preferred embodiment the product contains methyl salicylate in (i) none or in amounts of (ii) organoleptically effective amounts or (iii) 0.1 wt% or less. Most of these products are adjusted to pH 7.5-12 (see above).

The present invention provides a method for adding the flavor, flavor or characteristic of winter green to a product or for enhancing the flavor, flavor or characteristic of winter green to a product. The method comprises the steps of (a) adding a product (in a mixture according to the invention) mixture MS or (b) an effective amount of the fragrance or flavor dispersing composition according to the invention to the product. The product preferably comprises (i) no methyl salicylate after (a) addition of the mixture MS or (b) the composition according to the invention, or (ii) up to a sensory effective amount or (iii) 0.1 It is preferable to contain in weight% or less. The composition is preferably chewing gum, toothpaste or mouthwash.

In addition, the present invention provides a method for reducing the amount of methyl salicylate in the fragrance or flavor divergent composition of wintergreen, comprising the step of replacing some or all of the methyl salicylate in the composition with a mixture MS (ie, the mixture of the present invention). Provide a method.

Ingredients that may be present in the flavored and flavored products according to the invention may exert additional effects. For example, preservatives, abrasives, anti-acne, skin aging inhibitors, antibacterial agents, anticellulose, anti-dandruff, anti-inflammatory agents, anti-inflammatory agents, inflammation inhibitors, antimicrobial agents, antioxidants, astringents, antiperspirants, preservatives, Antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, depilators, surfactants, deodorants, antiperspirants, emollients, emulsifiers, enzymes, essential oils ), Fibers, film formers, fixers, foam formers, foam stabilizers, antifoams, foam boosters, antifungal agents, gelling agents, gel formers, hair care agents, hair shaping agents, hair smoothing (smoothing), moisture supply, moisturizing material, hygroscopic material, bleach, reinforcing agent, decontamination agent, optical brightener, penetrant, oil repellents, friction reducer, lubricant, moisturizing cream, ointment, opaque agent, Plasticizers, covering agents, poly Polish, sheen agent, polymer, powder, protein, refatting agent, abrasive, silicone, skin soothing agent, skin cleanser, skin care agent, skin treatment agent, skin-whitening agent, skin protectant, skin Softeners, Cooling Agents, Skin Cooling Agents, Warming Agents, Skin Warming Agents, Stabilizers, UV-Absorbents, UV Filters, Cleaners, Softeners, Suspending Agents, Skin Tanning Agents, Thickeners, Vitamins, Oils, Waxes, Fats , Phospholipids, saturated fatty acids, mono or polyunsaturated fatty acids, -hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, pigment protectants, pigments, anticorrosive agents, aromas, flavors, fragrances or alcohols, polyols, electrolytes, It may be a conventional component of cosmetic or dermatological formulations such as organic solvents or silicone derivatives.

In addition, the combination of the mixture MS and the cooling agent is particularly advantageous. Examples of cooling agents include 1-menthol, mentonglycerol acetal, menthyl lactate, substituted menthyl-3-carboxamides (eg N-ethylmentyl-3-carboxamide), 2-isopropyl-N, 2, 3-trimethylbutanamide, substituted cyclohexanecarboxamide, 3-mentoxypropane-1,2-diol, 2-hydroxyethyl menthylcarbonate, 2-hydroxypropyl menthylcarbonate, N-acetylglycine Menthyl ester, menthyl hydroxycarboxylate (eg menthyl-3-hydroxybutyrate), monomentyl succinate, 2-mercaptocyclodecanone, menthyl-2-pyrrolidin-5-onecarboxylate are mentioned Can be.

In the novel flavor formulations and flavor diverging compositions, the mixture MS can be used as the sole flavoring agent or in combination with other flavor compounds to give the composition the flavor of wintergreen or the character of wintergreen. More specifically, the mixture MS according to the present invention is advantageously mixed with peppermint oil, spearmint oil, menthol, cinnamon flavor, anise, root beer flavor, bubble gum flavor, spice flavor, citrus oil and fruit flavor. Such flavor dissipating compositions include natural or artificial ingredients or a mixture of both. The combination of a cooling agent such as menthol, menton ketal, N-substituted-p-mentane carboxamide and 3-1-mentoxypropane-1,2-diol with the mixture MS according to the invention is particularly sufficient.

The mixture MS according to the invention produces surprisingly enhanced effects in combination with other directions in the fragrance composition and in the flavored product as well as in the single direction.

As described above, the fragrance or flavor divergent composition according to the present invention comprises a sensory effective amount of the mixture MS.

The amount of mixture MS according to the invention in the fragrance composition according to the invention is generally about 0.05 to 99% by weight, preferably 5 to 90% by weight, more preferably 10 to 70% by weight, based on the total weight of the fragrance composition. .

The amount of the mixture MS according to the invention in the flavor dispersing composition according to the invention is generally about 0.05 to 99% by weight, preferably 1 to 80% by weight, more preferably 5 to 50% by weight, based on the total weight of the flavor dissipation composition. %to be.

In general, products flavored according to the present invention contain about 0.05 to 5%, typically about 0.2 to 2%, by weight of the flavored composition of the present invention.

Generally, products flavored according to the present invention contain the fragrance composition of the present invention from about 0.05 to 5%, typically from about 0.2 to 2% by weight of the final flavored product.

Typically the flavored product contains a mixture MS of the present invention about 0.05 to 5%, preferably about 0.1 to 2% by weight of the final flavored composition.

Typically the flavored product contains the mixture MS of the present invention about 0.05 to 2% by weight, preferably about 0.1 to 0.5% by weight of the final flavored product.

The exact dosage will depend on the desired aroma of the final product or the nature of the flavor dispersing composition and the choice of the perfume expert or flavor expert combining the flavor dispersing composition.

Additive products include foods, beverages, sweets, pharmaceuticals, chewing gum, mouthwashes, toothpastes, and other items consistent with the above definition. The flavored product, in particular the oral composition, may be in the form conventional in the art such as, for example, pastes, gels, mousses, aerosols, gums, lozenges, powders, creams and the like, and double-compartment dispensers It can also be formulated into a system usable as.

The invention particularly relates to the use of the mixture MS as a flavoring agent for oral care products and confectionary products, such as, for example, chewing gum, candy, edible films, rejuvenating capsules, pharmaceutical preparations, dentifrices, toothpastes, mouthwashes and the like. It is about. In products where methyl salicylate is currently used, the mixture MS can be used to enhance the wintergreen flavor or to replace some or all of the compounds.

In a preferred embodiment, the flavored product is chewing gum. Such chewing gum typically contains about 0.25 to about 3 weight percent of the total flavor weight, and most typically contains about 0.8 to 1.5 weight percent.

Generally such chewing gum comprises a water soluble bulk portion, a water insoluble chewable gum base portion and a typically water insoluble flavor component.

The water soluble bulk portion disappears with the portion of the flavor over time during chewing. The gum base remains in the mouth throughout chewing.

Insoluble gum bases generally include elastomers, resins, fats and oils, waxes, emollients and inorganic fillers. The insoluble gum base is about 5 to about 95 weight percent of the gum and more preferably about 20 to 30 weight percent. All percentage values represent weight percentages.

The gum base also generally includes a filler component. The filler component can be calcium carbonate, magnesium carbonate, talc, dicalcium phosphate, and the like. The filler comprises about 5% to about 60% of the gum base. Preferably the filler consists of about 5% to about 50% of the gum base. The gum base also contains emollients, including glycerol monostearate and glycerol triacetate. In addition, the gum base may also include additional ingredients such as antioxidants, pigments and emulsifiers. It is possible in the present invention to use a commercially acceptable gum base.

The water soluble portion of the chewing gum may further contain emollients, sweeteners and flavors and combinations thereof. The softener is added to the chewing gum to optimize the chewing ability of the gum and tactile sensation in the mouth. Softeners, also known as plasticizers, generally comprise from about 0.1% to about 15% of chewing gum. Emollients in the present invention include glycerin, lecithin and combinations thereof. Water-soluble sweetener solutions such as sorbitol, hydrogenated starch hydrolysis products, corn syrup and combinations thereof can be used as emollients and binders in gum.

Sweeteners that can be used in the chewing gum in the present invention include both sugar and sugar free ingredients. Sugar sugar sweeteners include saccharide-containing ingredients commonly known in the art, including but not limited to sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, Galactose, corn syrup solids, alone or in combination. Sugar-free sweeteners include, but are not limited to, sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, hydrogenated isomaltulose, tagatose, which are commonly lacking in known sugars and have sweetening properties. ^® and such sugar alcohols alone or in combination. High-strength sweeteners such as aspartame, sucralose, cyclate, acesulfame-K, dihydrocalon, glycyrrhizin, alitam, saccharin and their acceptable salts for food are added directly to the gum Can be.

Those skilled in the art will appreciate that any combination of sugar / sugar free sweeteners may be incorporated into the chewing gum. Those skilled in the art will also recognize that the sweetener will be present in the chewing gum completely or partially as a water soluble bulking agent and the softener will be combined with a sweetener such as a water soluble sweetener solution.

Generally chewing gum is prepared by sequentially adding various chewing gum ingredients to commercially available mixers known in the art. After the ingredients are thoroughly mixed, the gum mass is discharged from the mixer and rolled into sheets to be cut into rods, extruded into large chunks, or cast into pellets to form the desired shape. Generally the ingredients are mixed by first melting the gum base and then adding it to a working mixer. The base can also be melted in the mixer itself. Pigments may also be added at this time. Softeners, such as glycerin, may then be added as part of the syrup and bulking agent. Additional portions of the bulking agent may be added to the mixer.

Preferably the flavor component is added to the gum mixture at the end of the mixing process. The entire mixing process takes about 5 to 15 minutes, but longer mixing times may be required. Those skilled in the art will appreciate that various modifications to the above described processes are possible.

In a preferred embodiment the flavored product is a toothpaste.

Toothpastes flavored with the mixture MS according to the invention include, for example, polishing systems (polishing agents or polishes) which are silicic acid, calcium carbonate, calcium phosphate, aluminum oxide and / or hydroxyl apatite; Surfactants which are, for example, sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropylbetaine; Humectants, for example glycerol and / or sorbitol; Carboxymethyl cellulose, polyethylene glycol, carrageenan, Laponite ^® phosphorus thickeners; Sweeteners, for example saccharin; Stabilizers and for example sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluoride, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, It consists of an active ingredient which is cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide and / or sodium bicarbonate.

The mixture MS of the present invention in toothpaste and chewing gum is used at a concentration of 0.05 to 2% by weight, preferably 0.1 to 1% by weight, more preferably 0.1 to 0.5% by weight. The content of the mixture MS according to the invention in the sucking candy is from 0.01 to 2% by weight, preferably from 0.05 to 1% by weight and more preferably from 0.1 to 0.5% by weight.

In another preferred embodiment the flavored product is a mouthwash.

The content of the mixture MS according to the invention is 0.01 to 1% by weight, preferably 0.1 to 0.5% by weight in ready-to-use mouthwashes. The content of the composition containing the mixture MS according to the invention in the concentrate of the mouthwash is from 0.01 to 20% by weight, preferably from 0.1 to 10% by weight, more preferably from 3 to 5% by weight.

High concentrations in ready-to-use flavored products, for example 5% by weight, result in less typical wintergreen taste profiles, ie phenolic and medicinal characteristics, than those generally accepted and preferred by consumers.

When the final product containing the mixture MS of the present invention is used, the mixture MS of the present invention or a composition containing the same is particularly suitable for refreshing breath and neutralizing or reducing bad breath.

The use of the mixture MS of the present invention or compositions containing such mixtures in oral care products such as mouthwashes and toothpastes and chewing gums include triclosan, zinc citrate, zinc sulfate, polyphosphate and pyrophosphate, bicarbonate, Strontium salts and potassium salts, tin pyrophosphate, tin chloride, aluminum lactate, hydrogen peroxide, fluoride, vitamins, cetylpyridinium chloride and, for example, sodium lauryl sulfate, sodium lauryl sarcosinate, cocamidopropylbetaine Emulsifiers such as aspartame, saccharin, acesulfame-K, sorbitol; Badly caused by substances such as xylitol cyclate (e.g. sodium cyclate), sucralose, altam, neotam, saumatin, neohesperidin DC, maltitol, lactitol or sweeteners that are chewing gum base Especially bitter taste may be blocked or neutralized.

A further advantage of the inventive mixtures MS is their stability in toothpastes based on chalk or bicarbonate, which makes it difficult to introduce flavor divergence due to alkaline pH.

Examples of aromas, flavors and aromas used in the products according to the invention are described in K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th. See Ed., Wiley-VCH, Weinheim 2001.

In particular, amber bugless tincture; Amiris oil; Angelica seed oil; Angelica root oil; Anise fruit oil; Valerian oil; Basil oil; Wood morse absolute; Laurel feeding; Mugwort oil; Benzoin resins; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calmus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassia absolut; Casterium Absolute; Counted leaf oil; Cedar wood oil; Sister oils; Citronella oil; Lemon oil; Copaiba balsam; Copaiba balsam oil; Coriander oil; Coasters root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute; Oak mos absolute; Elemi oil; Estragone oil; Eucalyptus citridora oil; Eucalyptus oil; Fennel oil; Spruce needle oil; Galvanium oil; Galvanium resin; Germanium oil; Grape fruit oil; Guac Wood U; Gurjun balsam; Gurjun balsam oil; HeliCrism Absolute; Helicre fiber; Ginger oil; Iris root absolute; Iris root oil; Jasmine absolute; Calmus oil; Blue chamomile oil; Roman chamomile oil; Carrot seed oil; Cascarilla oil; Fine needle oil; Sparemint oil; Caraway oil; Rabdanum oil; Rabdanium absolute; Rabdanium resins; Labandine Absolute; Labandine oil; Lavender absolute; Lavender oil; Lemongrass oil; Rosemary oil; Distilled lime oil; Extruded lime oil; Linaloe oil; Lichia Kubebayu; Laurel leaf oil; Mace oil; Marjoram oil; Mandarin oil; Mazoi bark oil; Mimosa absolute; Musk seed oil; Musk tincture; Clary sage oil; Nutmeg oil; Mir absolute; Mir oil; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Olibanium absolute; Olibanium oil; Opofanax oil; Orange flower absolut; Orange oil; Organic oils; Palmarose; Patchouli oil; Perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Pettigrain oil; Peppermint oil; Pepper oil; Pimento oil; Pine oil; Penny royal oil; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Dalmation Sage Oil; Spanish sage oil; Sandalwood oil; Celery seed oil; Spike lavender oil; Japanese anise oil; Styrex oil; Tagetes oil; Fir oil; Tea tree oil; Turpentine oil; Thyme oil; Tolu balsam; Tongka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; Verbena oil; Vetiver oil; Juniper oil; Wineless oil; Absinthe oil; Winter green oil; Ylang-ylang; Hishop u; Civet absolute; Cinnamon leaf oil; Extracts derived from natural raw materials such as essential oils such as cinnamon hull oil, concrete, absolute, resins, resinoids, balsams, tinctures; And their separations or components separated therefrom;

For example, 3-karen; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; Bisabolene; Camphor; Cariophyllene; Cedrene; Farnesene; Limonene; Longipolene; Myrsen; Osmenene; Valencene; Individual directions selected from the group of hydrocarbons such as (E, Z) -1, 3, 5-undecatriene;

For example, hexanol; Octanol; 3-octanol; 2,6-dimethylheptanol; 2-methylheptanol, 2-methyloctanol; (E) -2-hexenol; (E)-and (Z) -3-hexenol; 1-octen-3-ol; A mixture of 3,4,5,6,6-pentamethyl-3 / 4-heptene-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-dekenol; 10-undekenol; Aliphatic alcohols such as 4-methyl-3-deken-5-ol; And for example hexanal; Heptane; Octanal; Nonanal egg; Decanal; Undecane; Dodecanal; Tridecanal; 2-methyloctanal; 2-methylnonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecal; (E) -4-dekenal; 2-dodekenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanal diethyl acetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; Aliphatic aldehydes such as citronellyl oxyacetaldehyde and their 1,4-dioxacycloalkene-2-ones;

For example, 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; Aliphatic ketones such as 2,4,4,7-tetramethyl-6-octen-3-one and oximes thereof; For example, 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-metcaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; Aliphatic sulfur-containing compounds such as 1-mentene-8-thiol;

For example, 2-nonenenitrile; 2-tridekennitrile; 2,12-tridekennitrile; 3,7-dimethyl-2,6-octadienenitrile; Aliphatic nitriles such as 3,7-dimethyl-6-octenitrile;

For example, (E)-and (Z) -3-hexenyl formate; Ethyl acetoacetate; Isoamyl acetate; Hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E)-and (Z) -3-hexenyl acetate; Octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; Ethyl butyrate; Butyl butyrate; Isoamyl butyrate; Hexyl butyrate; (E) and (Z) -3-hexenyl isobutyrate; Hexyl crotonate; Ethyl isovalerate; Ethyl 2-methylpentanoate; Ethyl hexanoate; Allyl hexanoate; Ethyl heptanoate; Allyl heptanoate; Ethyl octanoate; Ethyl (E, Z) -2,4-decadienoate; Methyl 2-octynoate; Methyl 2-noninoate; Allyl 2-isoamyloxyacetate; Aliphatic carboxylic acids and esters thereof such as methyl 3,7-dimethyl-2,6-octadienoate;

For example, citronellol; Geraniol; Nerol; Linarool; Labandurol; Nerolidol; Farnesol; Tetrahydrolinarool; Tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol; Acyclic terpene alcohols such as 2,6-dimethyl-2,5,7-octatrien-1-ol; And their formate, acetate, propionate, isobutyrate, butyrate, isovalerate, pentanoate, hexanoate, crotonate, tiglynate, 3-methyl-2-butenoate salts;

For example, geraniol; Neral; Citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undekenal; Acyclic terpene aldehydes and ketones such as geranyl acetone; And geranial, neral, dimethyl and diethyl acetal of 7-hydroxy-3,7-dimethyloctanal;

For example, menthol; Isofuregol; Alpha-terpineol; Terpineol-4; Mentan-8-ol; Mentan-1-ol; Mentan-7-ol; Borneol; Isobornaneol; Linarool oxide; Nopol; Cedrol; Amberlinol; Cyclic terpene alcohols such as vetiverol and guaiol; And their formate, acetate, propionate, isobutyrate, butyrate, isovalerate, pentanoate, hexanoate, crotonate, tiglynate, 3-methyl-2-butenoate;

For example, menton; Isomentone; 8-mercaptomentan-3-one; Carbon; Camphor; Fenchon; Alpha-ionone; Beta-ionone; Alpha-n-methylionone; Beta-n-methylionone; Alpha-isomethylionone; Beta-isomethylionone; Alpha-theory; Alpha-damascone; Beta-damascone; Beta-damaskenone; Delta-damascone; Gamma-damascone; 1- (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8 (5H) -one; Nutcanone; Dihydronutcanone; Alpha-cinenesal; Beta-senensal; Cyclic terpene aldehydes and ketones such as acetylated cedarwood oil (methyl cedryl ketone);

For example, 4-tert-butylcyclohexanal; 3,3,5-trimethylcyclohexanal; 3-isocampylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecaten-1-ol; Cyclic alcohols such as 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

For example, alpha-3,3-trimethylcyclohexylmethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -butene-1ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; Cyclic aliphatic alcohols such as 1- (2,2,6-trimethylcyclo-hexyl) hexan-3-ol;

For example, cineol; Cedryl methyl ether; Cyclododecyl methyl ether; (Ethoxymethoxy) cyclododecane; Alpha-cedrene epoxides; 3a, 6,6,9a-tetramethyldodecahydronaphtho [2,1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1,5,9-trimethyl-13-oxabicyclo [10.1.0] trideca-4,8-diene; Rose oxide; Cyclic and cyclic aliphatic ethers such as 2- (2,4-dimethyl-3-cyclohexen-1yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;

For example, 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-l-one; 3-methyl-cis-2-penten-l-yl-2-cyclopenten-l-one; 3-methyl-2-pentyl-2-cyclopenten-l-one; 3-methyl-4-cyclopentadekenone; 3-methyl-5-cyclopentadekenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexanedeken-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) -danone; 5-cyclohexadeken-1-one; 8-cyclohexadeken-1-one; 9-cycloheptadeken-1-one; Cyclic ketones such as cyclopentadecanone;

For example, 2,4-dimethyl-3-cyclohexenecarbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarbaldehyde; Cyclic aliphatic aldehydes such as 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;

For example, 1- (3,3-dimethylcyclohexyl) -4-penten-l-one; 1- (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-l-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; cyclic aliphatic ketones such as tert-butyl 2,4-dimethyl-3-cyclohexen-1-yl ketone;

For example, 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate; Esters of cyclic alcohols such as 4,7-methanooctahydro-5 or 6-indenyl acetate;

For example, allyl 3-cyclohexylpropionate; Allyl cyclohexyloxyacetate; Methyl dihydrozasmonate; Methyl jasmonate; Methyl 2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Esters of cyclic aliphatic carboxylic acids such as ethyl 2-methyl-1,3-dioxolane-2-acetate;

Aromatic hydrocarbons such as, for example, styrene and diphenylmethane;

For example, benzyl alcohol; 1-phenylethyl alcohol; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; Aromatic aliphatic alcohols such as 1- (4-isopropylphenyl) ethanol;

For example benzyl acetate; Benzyl propionate; Benzyl isobutyrate; Benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; Alpha-trichloromethylbenzyl acetate; Alpha, alpha-dimethylphenylethyl acetate; Alpha, alpha-dimethylphenylethyl butyrate; Cinnamic acetate; 2-phenoxyethyl isobutyrate; Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids such as 4-methoxybenzyl acetate; For example, 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl 1-ethoxyethyl ether; Phenylacetaldehyde dimethyl acetal; Phenylacetaldehyde diethyl acetal; Hydratropaldehyde dimethyl acetal; Phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; Aromatic aliphatic ethers such as 4,4a, 5,9b-tetrahydro-2,4-dimethyllindeno [1,2-d] -m-dioxine;

For example, benzaldehyde; Phenylacetaldehyde; 3-phenylpropanal; Hydratropaldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-methyl-3- (4-tert-butylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; Cinnamic aldehyde; Alpha-butyl cinnamic aldehyde; Alpha-amylcinnamaldehyde; Alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) -propanal; Aromatic and aromatic aliphatic aldehydes such as 2-methyl-3- (4-methylenedioxyphenyl) propanal;

For example, acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; Benzophenones; 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone; 1- [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; Aromatic and aromatic aliphatic ketones such as 5 ′, 6 ′, 7 ′, 8′-tetrahydro-3 ′, 5 ′, 5 ′, 6 ′, 8 ′, 8′-hexamethyl-2-acetonaphtone;

For example, benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate; Benzyl benzoate, methyl phenylacetate; Ethyl phenylacetate; Geranyl phenylacetate; Phenylethyl phenylacetate; Methyl cinnamate; Ethyl cinnamate; Benzyl cinnamic acid; Phenylethyl cinnamic acid; Shin Nam Il Shin Nam Eight; Allyl phenoxyacetate; Isoamyl salicylate; Hexyl salicylate; Cyclohexyl salicylate; Cis-3-hexenyl salicylate; Benzyl salicylate; Phenylethyl salicylate; Methyl 2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Aromatic and aromatic aliphatic carboxylic acids such as ethyl 3-methyl-3-phenylglycidate;

For example, 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; Cinnamic nitrile; 5-phenyl-3-methyl-2-pentenenitrile; 5-phenyl-3-methylpentanenitrile; Methyl anthranilate; Methyl N-methylanthranilate; Schiff of 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde with methyl anthranilate Schiff base; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; Indole; Scartol; 2-methoxy-3-isopropylpyrazine; Nitrogen-containing aromatic compounds such as 2-isobutyl-3-methoxypyrazine;

For example, estradiol; Anethol; Eugenol; Eugenyl methyl ether; Isoeugenol; Isoeugenyl methyl ether; Thymol; Carbakrol; Diphenyl ether; Beta-naphthyl methyl ether; Beta-naphthyl ethyl ether; Beta-naphthyl isobutyl ether; 1,4-dimethoxybenzene; Eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; phenols such as p-cresyl phenylacetate, phenyl ethers and phenyl esters;

For example, 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; Heterocyclic compounds such as 2-ethyl-3-hydroxy-4H-pyran-4-one;

For example, 1,4-octane oxide; 3-methyl-1,4-octane oxide; 1,4-nonan oxide; 1,4-decanoxide, 8-deken-1,4-oxide; 1,4-undecanoxide; 1,4-dodecane oxide; 1,5-decanoxide; 1,5-dodecaneoxide, 1,15-pentadecanoxide; Cis and trans-11-pentadekene-1,15-oxide; Cis- and trans-12-pentadekene-1,15-oxides; 1,16-hexadecaneoxide; 9-hexadeken-1,16-oxide; 10-oxa-1,16-hexadecaneoxide; 11-oxa-1,16-hexadecaneoxide; 12-oxa-1,16-hexadecaneoxide; Ethylene 1,12-dodecanedioate; Ethylene 1,13-tridecanedioate; Coumarin; 2,3-dihydrocoumarin; Lactones such as octahydrocomarin.

The fragrance or flavor divergent composition containing the mixture MS of the present invention may be in liquid form, either pure or diluted with a solvent. Suitable solvents for this purpose are ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin And so on.

In addition, the fragrance or flavor divergent composition containing the mixture MS of the present invention can be adsorbed onto a carrier which can finely disperse the fragrance or flavor in the product and release them in a controlled manner during use. As such a carrier, organic materials such as porous inorganic materials such as light sulphate, silica gel, zeolite, gypsum, clay, clay particles, gas concrete, etc., or materials of wood and cellulose type may be used.

The fragrance or flavor divergent composition containing the mixture MS of the present invention may be added to a subject that is microencapsulated or spray dried, respectively, in the form of an incorporation complex or in the form of a compression molding to be flavored or flavored in that form.

The properties of the fragrance or flavor divergent composition modified in this way can be further optimized by optionally "coating" with a material suitable for more targeted fragrance or flavor release. Wax like polymers such as, for example, polyvinyl alcohol can be used for this purpose.

Microencapsulation of the fragrance or flavor divergent composition can be carried out by, for example, a "coacervation method" using a capsule material made from a polyurethane-like material or soft gelatin. Spray dried aroma or flavor divergent compositions can be prepared by spray drying emulsions or dispersions containing, for example, aroma or flavor divergent compositions in which starch, protein dextrin and vegetable gum modified with a carrier are used. Inclusion complexes can be prepared, for example, by introducing a dispersion of aroma or flavor divergent compositions and cyclodextrins or urea derivatives into a suitable solvent, for example. Extrusions can be obtained by melting the fragrance or flavor dispersing composition with a suitable wax like material and solidifying and injecting, for example, in a suitable solvent such as isopropanol.

Preparations for example perfume extracts, eau de parfum, eau de toilette, aftershave, eau de cologne, pre-shave products, splash cologne and flavored refreshing towels, and for example floor cleaners, windows Detergents for cleaning, dishwashing detergents, bath and sanitary containers, scouring milk, solid and liquid WC cleaners, carpet cleaners with powdery foams, liquid laundry detergents, powdered laundry detergents, Acidic, alkaline and neutral cleaning agents such as, for example, laundry pretreatments such as bleach, immersion and decontamination agents, fabric softeners, cleaning soaps, cleaning tablets, disinfectants, surface disinfectants, and liquid or gel form or solid carriers. Waxes and polishes such as air cleaners, aerosol sprays, floor waxes, shoe creams, furniture polishes, and solid and liquid soaps, shower gels, Body care compositions such as shampoos, shaving soaps, shaving foams, bath oils, for example skin creams and lotions, face creams and lotions, sunscreen creams and lotions, aftershave creams and lotions, hand creams and lotions, foot creams and lotions Cosmetic emulsions in the form of oil-in-water, water-in-oil, water-in-oil, such as depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, for example hair sprays, hair gels, hair setting lotions, hair rinses Hair care products such as permanent and semi-permanent hair dyes, hair shaping compositions such as cold wave and hair smoothing compositions, hair tonics, hair creams and lotions such as armpit sprays, roll-ons, deodorant sticks, Deodorants and antiperspirants such as deodorant creams, for example, decorative cosmetic products such as eyeshadows, nail varnishes, foundations, lipsticks, mascara, candles, Au oils, incense stick, pesticide, insecticide, containing the mixture MS according to the present invention for flavoring direction of the propellant composition may be used in a modified form of the concrete form, the solution or above.

The following examples are intended to illustrate the use of the mixtures MS (compounds A), B), C) D) and optionally mixtures E) of the invention. However, the use of the mixture MS of the present invention is not limited to the following examples.

Hereinafter, unless stated otherwise, the amount means weight.

<Example 1>

compound Parts by weight of composition X Parts by weight of composition Y Parts by weight of composition Z Eucalyptol 100 100 100 L-menthol 500 500 500 L-mentyl acetate 130 130 130 L-carbon 20 20 20 Anetol 100 100 100 Methyl salicylate 150 - 25 Mixture MSa - 150 125

The mixture MSa consists of 3.7 wt% dihydroanetol, 7.1 wt% o-anisaldehyde, 44.6 wt% 1,3-dimethoxybenzene and 44.6 wt% 2'-hydroxyacetophenone.

Compositions X to Z were mixed and individually added to the silica based toothpaste. The amount was 1.2% by weight based on the total weight of the toothpaste.

Compositions X to Z were mixed and individually added to chewing gum. The amount was 1.2% by weight based on the total weight of the chewing gum.

Sensory properties, as such and as added products of Compositions X to Z, were evaluated by eight trained examiners. Compositions X to Z and the flavored product showed a typical wintergreen taste with only minor differences in some aspects.

<Example 2>

A clear toothpaste gel was prepared having a capsule consisting of the following formulation and loaded with the mixture MS1.

ingredient Parts by weight 1. Sorbitol, 70% strength 2. Distilled water 3. Saccharin 4. Sodium monofluorophosphate 5. Trisodium phosphate 6. Polyethylene glycol PEG 1500 (PEG 32) 7. Polishing silica gel 8. Silica gel for thickener 9. Sodium Carboxymethyl cellulose 10. Sodium lauryl sulfate 11. Mixture MS1 12. Capsules stained blue and red 13. 4-hydroxybenzoic acid methyl ester 61.50 11.40 0.20 1.10 0.10 5.50 8.00 8.00 0.60 1.50 1.00 1.00 0.10

The mixture MS1 was 4.5 wt% dihydroanetol, 8.9 wt% o-anisaldehyde, 37.3 wt% 1,3-dimethoxybenzene, 34.3 wt% 2'-hydroxyacetophenone and 15 wt% 2 '-Methoxyacetophenone.

Toothpaste has a typical wintergreen flavor.

<Example 3>

A calcium carbonate toothpaste (pH = 9.6) was prepared, consisting of the following formulations and fed a mixture of MS2.

ingredient Parts by weight 1. Calcium Carbonate 2. Sorbitol 3. Hydrogenated Silica 4. Sodium Monoflurophosphate 5. Trisodium Phosphate 6. Titanium Dioxide 7. Sodium Carboxymethyl Cellulose 8. Sodium Lauryl Sulfate 9. Sodium Saccharin 10. Sodium Fluoride 10. Mixture MS2 11.Additional flavor 12.Water 40.00 27.00 2.00 0.80 0.50 1.00 0.90 2.00 0.20 0.20 0.70 0.40 24.30

Mixture MS2 comprises 2.8% by weight of dihydroanetol; 7.0% by weight o-anisaldehyde, 39.4% by weight 1,3-dimethoxybenzene, 42.3% by weight 2'-hydroxyacetophenone and 8.5% by weight 2'-methoxyacetophenone.

Further flavoring agents include l-menthol, l-carbon, anetol and the cooling compounds N-ethyl-p-mentan-3-carboxamide, l-mentillactate. l-menthol glycol carbonate and l-menthol propyleneglycol carbonate.

The flavor and sensory profile of these alkaline calcium carbonate toothpastes have remained stable for a long time.

Toothpaste, which has a cooling effect, long lasting and refreshing breath, has a good winter green flavor without bitterness or taste.

<Example 4>

With the following formulation, a ready-to-use mouthwash was prepared with the mixture MS2.

ingredient Parts by weight ethanol 7.00 glycerin 12.00 Sodium Floride 0.05 Pluronic F-127 ^® (BASF, Surfactant) 1.40 Na-phosphate buffer pH 7.0 1.10 Sorbic acid 0.20 Sodium saccharin 0.10 Additive flavoring agents such as mixture MS2 and Example 3 0.25 Pigment FD & C Blue # 1 0.01 water Added to 100 parts by weight

Example 5

Two wintergreen flavored chewing gums with the inventive mixture Msa (see Example 1) were prepared according to the following formulation.

compound Parts by weight of composition Cx Parts by weight of composition Cy Sugar 60.60 60.60 Gum base 21.00 21.00 Corn syrup 16.50 16.50 glycerin 1.30 1.30 lecithin 0.15 0.15 Perfemint oil 0.40 0.40 L-menthol 0.10 0.10 N-ethyl-p-mentan-3-carboxamide 0.05 0.05 Methyl salicylate 0.20 - Mixture MSa 0.55 0.75

Chewing gum formulation Cx contains a reduced amount of methyl salicylate.

Methyl salicylate in the chewing gum formulation Cy is completely replaced by the mixture MSa.

The chewing gum formulation is added to the gum base at a temperature of about 85 to 90 ° C. and added with mixing lecithin followed by one third of the corn syrup and sugar, until a homogeneous mixture is obtained, i. Mix again for 5 minutes. Subsequently, methyl salicylate and / or mixture MSa and glycerin were added and mixed for about 2 minutes each, then the remaining sugar was added and mixed until a homogeneous mixture was obtained, ie for about 2 minutes. The formulation was cooled at about 40-45 [deg.] C. and menthol and carboxamide compounds were added and mixed. The formulation thus obtained was cut into slab form.

Sensory evaluation studies were conducted on the formulations. Chewing gum formulations Cx and Cy have shown a characteristic wintergreen taste and long-lasting cooling and breathing refreshing action.

<Example 6>

With the following formulation, the fragrance composition (fragrance oil) to which the mixture MS1 was added was prepared.

compound Parts by weight Red berry extract 50 Bergamot oil without bergapten 80 Cardamom Absolute 25 Cyclopentadecaneoxide (1) 150 Cypress oil 5 Eugenol 50 Ginger Oil Synthesis 60 Methyl dihydrozasmonate 100 Iso E Super ^® (2) 150 Amarocit ^® (1) 50 Muscon 50 Clary Sage You 75 Vertocitral ^® (1) 45 Vetiver 10 Mixture MS1 as in Example 2 110

 Supplier:

(1) Jim Leeds Gembeha Ko. Kage, Holzminden, Germany

(2) International Flavor & Fragrance, Union Beach, New Jersey, USA

Claims (17)

A) dihydroanetol, B) o-anisaldehyde, C) 1,3-dimethoxybenzene, D) optionally with 2'-hydroxyacetophenone E) A mixture comprising or consisting of 2-methoxyacetophenone. The method of claim 1, And the ratio of the amounts of the compounds A), B), C) and D) and the compounds A), B), C) and D) is adjusted to have the flavor or aroma of wintergreen. The method according to claim 1 or 2, Wherein the ratio of A): B): C): D): E) is by weight about 5-80: 10-90: 100-500: 100-500: 0-200 by weight. A fragrance or flavor diverging composition which contains the mixture according to any one of claims 1 to 3 in a sensory effective amount. The method of claim 4, wherein Wherein said composition retains the flavor or aroma of wintergreen (i) generated or (ii) enhanced by the amount of the mixture. The method of claim 5, Including methyl salicylate, wherein the weight part of the mixture of methyl salicylate to A), B), C) and D) is from 10: 1 to 1:20, preferably from 4: 1 to 1:10. A fragrance or flavor divergent composition characterized by the above-mentioned. A flavored or flavored product containing (i) a mixture according to any one of claims 1 to 3 or (ii) an aromatic or flavor divergent composition according to any one of claims 4 to 6. The method of claim 7, wherein The product is characterized in that it retains the flavor or aroma of wintergreen (i) generated or (ii) enhanced by the amount of the mixture. The method according to claim 7 or 8, The product is a product characterized in that the chewing gum, toothpaste or mouthwash. The method according to any one of claims 7 to 9, The product is characterized in that the pH is from about 7.5 to about 12. The method according to any one of claims 7 to 10, If the product is a flavored product, the product contains from about 0.05 to 5% by weight of the mixture according to any one of claims 1 to 3. The method according to any one of claims 7 to 10, In the case of added products, the product contains from about 0.05 to 2% by weight of the mixture according to any one of claims 1 to 3. The method according to any one of claims 7 to 12, The product is characterized in that it contains no methyl salicylate (i) at all or (ii) up to a sensory effective amount or (iii) up to 0.1% by weight. adding or introducing into the product an effective amount of (a) a mixture according to any one of claims 1 to 3 or (b) an aromatic or flavor divergent composition according to any one of claims 4 to 6. Adding a wintergreen flavor, flavor or feature to the product, comprising, or enhancing the wintergreen flavor, flavor or feature of the product. The method of claim 13, The product may be prepared by (i) adding methyl salicylate after (a) adding a mixture according to any one of claims 1 to 3 or (b) a composition according to any one of claims 4 to 6. No content at all, or (ii) up to a sensory effective amount or (iii) up to 0.1 weight percent. The method of claim 13, Said product is chewing gum, toothpaste or mouthwash. A method for reducing the amount of methyl salicylate in a fragrance or flavor divergent composition of wintergreen, comprising the step of replacing part or all of the methyl salicylate in the composition with a mixture according to any one of claims 1 to 3. .