Antimicrobial mixtures

Abstract

An antimicrobial mixture is proposed which comprises or (essentially) consists of (a) at least one flavouring agent having an unsaturated six-membered ring structure, and (b) at least one physiological freshener.

Description

Technical Field

[0001] The present invention relates to the field of oral care and proposes new compositions for combating dental plaque and biofilm on teeth. Background Art

[0002] Nowadays, the treatment of oral diseases such as caries or periodontitis focuses on preventive actions. Therefore, reducing the damage of dental plaque / biofilm and the associated bacteria has become a focus. The main methods are mechanical removal of dental plaque and the use of toothpaste or mouthwash containing active ingredients that are known to control specific bacteria in dental plaque. One of these well-known antimicrobial active ingredients is carvacrol.

[0003] Looking at the biofilm as a whole, the complexity of naturally occurring biofilms is a huge challenge when it comes to the development of suitable test systems. As a result, applied solutions with specific anti-biofilm properties are virtually unknown and rarely used. Related prior art

[0004] EP 1830926 B1 (COLGATE) relates to mixtures effective as antibacterial, antiplaque, anti-inflammatory, antioxidant and anti-halitosis oral compositions. The active ingredients contain one or more active compounds from oregano extracts, such as thymol, carvacrol and rosmarinic acid. The oral composition may be in the form of a mouthwash; a dentifrice, including toothpaste, gel, powder; an animal product; a film; or a confectionery, such as a lozenge, etc.

[0005] WO 2006 053458A1 (GIVAUDAN) relates to antiseptic preparations for contact with the human body, in particular washing preparations including liquid soaps, which contain perfume ingredients active against Gram-negative bacteria, hydrotropes and surfactants. Such compositions are only in contact with the target site, such as the skin surface, for a short time, usually not more than 30 seconds.

[0006] WO 2008 068683A1 (FIRMENICH) relates to a flavoring composition for oral care products, confectionery products or beverages. The composition comprises an antimicrobial ingredient and optionally at least one currently used flavoring ingredient, wherein the antimicrobial ingredient comprises 3,4-dimethylphenol and one or more antimicrobial flavoring ingredients, all of which have a minimum inhibitory concentration of 1000 parts per million or less against two or more strains selected from the group consisting of Fusobacterium nucleatum, Fusobacterium sp., Porphyromonas gingivalis, Prevotella intermedia, Klebsiella pneumoniae, Veillonella alcalescens, Bacteroides melaninogenicus / Bacteroides forsythus, Selenomonas sputagena, Porphyromonas endodontalis, Prevotella melaninogenicus, and melaninogenica) and Streptococcus mutans.

[0007] WO 2011 055708A1 (LION) relates to a liquid composition for oral use, which contains a nonionic surfactant, a humectant selected from glycerol, propylene glycol, polyethylene glycol and sorbitol, 1-menthol, a paraben and a flavoring material selected from 3-octanol, 3-octyl acetate, 3-octanone and fenchone.

[0008] DE 10 2014 221451 A1 (HENKEL) relates to an oral and tooth care and cleaning product which contains, based on its weight, 1 to 60% by weight of at least one humectant selected from sorbitol, glycerol or mixtures thereof, 0.1 to 5% by weight of at least one cooling agent selected from menthol, menthyl lactate or mixtures thereof and 0.1 to 5% by weight of an oily extract from Sorrel leaves, which exhibits improved cleaning properties and prevents new dental plaque and has a long-lasting antibacterial action.

[0009] FR 3105732 A1 (EZAL) relates to a composition containing thymol or an essential oil containing thymol; carvacrol or an essential oil containing carvacrol, eucalyptol or an essential oil containing eucalyptol, eugenol or an essential oil containing eugenol, limonene or an essential oil containing limonene, and an aqueous gelling agent. It also relates to the use of the composition as an oral hygiene product and as a medicament, in particular for the treatment and / or prevention of oral pathologies and for the prevention and / or reduction of the formation of dental plaque.

[0010] US 5,346,615 A ​​(COLGATE) claims an antiplaque oral composition, such as a toothpaste, a gel dentifrice, a tooth powder, a mouthwash or rinse, a tooth hardener, an anticalculus composition, a chewing gum or a lozenge, comprising triclosan as an antiplaque component, the antiplaque action of which is unexpectedly and beneficially enhanced by the presence in the oral composition of a phenolic flavoring agent, such as eucalyptol, thymol, methyl salicylate, menthol, phenol, halogenated derivatives thereof and mixtures thereof.

[0011] US 5,945,087 A (PFIZER) discloses an oral rinse and dentifrice composition comprising a phenol selected from menthol, eucalyptol, methyl salicylate, thymol, triclosan and mixtures thereof, and cyclodextrin. The composition can be used to delay the formation of dental plaque, treat gingivitis and treat the presence of microorganisms in the oral cavity.

[0012] US2009 163530AA (LEUNG) claims an edible film comprising pullulan and an antimicrobially effective amount of the essential oils thymol, methyl salicylate, eucalyptol and menthol. The edible film is effective in killing plaque-producing bacteria that can lead to plaque, gingivitis and bad breath.

[0013] US2012 014884AA (COLGATE) discloses novel uses of specific menthol-derived compounds in methods of providing oral and systemic health benefits, and methods of up-regulating or down-regulating periodontal disease metabolites.

[0014] JP 2014 043441A2 (SUNSTAR) provides a composition for oral cavity and a Candida biofilm formation inhibitor containing geraniol and menthol. Purpose of the Invention

[0015] The object of the present invention is therefore to provide new active substances or active compositions capable of combating biofilms, in particular dental plaque in the oral cavity, which at the same time Highly effective against all or at least most types of microorganisms that cause such biofilms, even at low concentrations; Gentle on mucous membranes; Exhibit a pleasant fresh flavour; and Improved antimicrobial activity. Summary of the invention

[0016] The first object of the present invention relates to an antimicrobial mixture comprising or (essentially) consisting of the following ingredients: (a) at least one flavoring agent, and (b) at least one physiological cooling agent, wherein the flavoring agent is selected from the group consisting of unsaturated 6-membered ring structures of the following formulae (I) to (IX): wherein R, R1, R2 and R3 independently of one another represent hydrogen, C1-C3 alkyl or C3 alkenyl, C1-C3 alkoxy or acetate, and n represents 0 or 1.

[0017] When the above-mentioned general flavoring agents, in particular carvacrol, are combined with physiological cooling agents, a surprising new synergistic effect is observed in the fight against the microorganisms that cause biofilm in the oral cavity. The antibacterial effect against the decisive bacterial strains present in human saliva can be improved by this synergistic effect. The new mixture is particularly effective for bacterial strains selected from Porphyromonas gingivalis, Fusobacterium nucleatum, Prevotella intermedia and / or Streptococcus mutans. The product is mild to the mucous membrane and provides a fresh and pleasant taste.

[0018] A synergistic effect of natural oils containing the above-mentioned flavoring agents in general, and carvacrol in particular, with physiological cooling agents has also been observed. Flavoring

[0019] In a preferred embodiment, the unsaturated six-membered ring structure forming component (a) is selected from the group consisting of carvacrol, thymol, eugenol, eugenyl acetate, dianthramide B, myrtenol, cumenol and mixtures thereof, and essential oils containing at least one of the structures, such as oregano oil, thyme essential oil or marjoram essential oil.

[0020] Carvacrol (or cymophenol) It is a preferred flavoring agent and is a monoterpenoid phenol with the characteristic warm smell of oregano. It can be produced synthetically or extracted from a variety of natural sources. Carvacrol is found in oregano essential oil, thyme oil, oil extracted from pepper grass and wild bergamot. The essential oils of oregano and thyme subspecies contain between 5% and 75% carvacrol, while the savory subspecies contains between 1% and 45% carvacrol. Origanum majorana and Dittany of Crete are rich in carvacrol, with contents of 50% and 60-80%, respectively. It is also found in Agave and Lippia graveolens (Mexican oregano), both of the Verbenaceae family. Carvacrol has strong disinfectant, fungicidal and bactericidal effects and is used in mouthwashes, toothpastes and alcohol solutions for skin disinfection because of its pleasant taste (see Heinz Lüllmann, Klaus Mohr, Lutz Hein: Pharmakologie und Toxikologie, Georg Thieme, Stuttgart, 2010, p. 451.)

[0021] Thymol (also known as 2-isopropyl-5-methylphenol, IPMP) It is a natural monoterpenoid phenol derivative of p-cymene and an isomer of carvacrol. It is present in the oils of thyme, oregano, marjoram, ajwain and various other plants. It is a white crystalline substance with a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the unique, rich flavor of the seasoning crop thyme, and thymol is also produced by common thyme.

[0022] Eugenol It is an allyl chain substituted guaiacol. It is a colorless to pale yellow aromatic oily liquid extracted from certain essential oils, notably cloves, nutmeg, cinnamon, basil, and bay leaf. It is present in clove bud oil in concentrations of 80-90% and in clove leaf oil in concentrations of 82-88%. Eugenol has a pleasant, spicy, clove-like odor. The name is derived from Eugenia caryophyllata, the Linnaean nomenclature term previously used for cloves. The currently accepted name is Syzygiumaromaticum.

[0023] Eugenyl acetate, also known as acetyleugenol Is a phenylpropanoid compound found in cloves. In certain extract preparations, it is second only to the related compound eugenol in abundance. Like eugenol, it is found in a variety of plants such as Acacia nilotica and Piper betle and has similar antibacterial and antifungal properties against Candida albicans and Streptococcus mutans. It inhibits platelet aggregation and has partial agonist activity at AhR.

[0024] Myrtenol It is a bioactive isolate of Taxus spp. Physiological cooling agent

[0025] The physiological cooling agents forming component (b) are added to provide a cooling sensation and increase the antimicrobial activity of the composition. They are preferably selected from the types described in the following table (including their optical isomers and racemates):

[0026] The first important representative of the substances forming component (b) is monomenthyl succinate, which as a substance was patented as early as 1963 by the Brown & Williamson Tobacco Company (US 3,111,127) and as a refrigerant is the subject of the property rights US 5,725,865 and 5,843,466 (V. Mane Fils). Succinate and the similar monomenthyl glutarate are important representatives of monomenthyl esters based on dibasic and polybasic carboxylic acids:

[0027] Examples of the use of these substances can be found, for example, in the printed documents WO 2003 043431 (Unilever) or EP 1 332 772 A1 (IFF).

[0028] The next important menthol compounds which are preferred in the sense of the present invention include menthol and polyols, for example glycols, glycerol or carbohydrate carbonates, for example menthol ethylene glycol carbonate, menthol propylene glycol carbonate, menthol 2-methyl-1,2-propanediol carbonate or the corresponding sugar derivatives:

[0029] The use of such substances as cigarette coolants is the subject of, for example, US Pat. No. 3,419,543 (Mold et al.), published in 1968; their use as physiological coolants is claimed in DE 4226043 A1 (H&R).

[0030] For purposes of the present invention, preferred menthol compounds are menthone glycerol acetal, menthone glycerol ketal and menthyl lactate, with menthyl lactate being most preferred.

[0031] The former structure is obtained by esterification of lactic acid with menthol, the latter by acetylation of menthone with glycerol (see DE 2608226A1, H&R). This group of compounds also includes 3-(l-menthoxy)-1,2-propanediol, also known as coolant 10 (US 6,328,982, TIC) and 3-(l-menthoxy)-2-methyl-1,2-propanediol, which has an additional methyl group.

[0032] For example, 3-(1-menthyloxy)-1,2-propanediol is prepared starting from menthol according to the following scheme (see US 4,459,425, Takasago):

[0033] An alternative route for the reaction of menthol with epichlorohydrin in the first step is described in US 6,407,293 and US 6,515,188 (Takasago). The following is a summary of preferred menthol compounds characterized by CO bonding:

[0034] Among these substances are menthone glycerol acetal / ketal and menthyl lactate as well as menthol ethylene glycol carbonate and menthol propylene glycol carbonate.

[0035] In the 1970s, menthol compounds with a CC bond in the 3-position were first developed, and many of their representatives can also be used in the sense of the present invention. These substances are generally referred to as WS types. Its base is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1). All other WS types are derived from this structure, such as the types WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30, which are also preferred in the sense of the present invention. The following two figures show the synthesis route:

[0036] Esters derived from WS-1 are described, for example, in US 4,157,384, and the corresponding N-substituted amides are described in J. Soc. Cosmet. Chem. pp. 185-200 (1978).

[0037] Preferred physiological cooling agents include menthyl lactate, menthyl propylene glycol carbonate, menthone glycerol acetal / ketal and 3-(-)-menthoxy)propane-1,2-diol.

[0038] In another preferred embodiment, components (a) and (b) may be present in a weight ratio of about 1:99 to about 99:1, preferably 10:90 to about 90:10, preferably about 20:80 to about 80:20, more preferably about 40:60 to about 60:40. Solvents

[0039] In another preferred embodiment, the mixture according to the invention may include a solvent, such as water, ethanol, 1,2-propylene glycol, 1,3-propylene glycol, triacetin, vegetable oils, triglycerides or glycerol and triethyl citrate or mixtures thereof. If solvents are present, their amount is generally from about 5 to about 95% by weight, preferably from about 10 to about 75% by weight, more preferably from about 25 to about 50% by weight.

[0040] If present, aromatic solvents are generally present in an amount of about 5 to about 95 weight percent, preferably about 10 to 90 weight percent, and more preferably 20 to 80 weight percent. Aromatic compounds

[0041] In another preferred embodiment, the mixture according to the invention may comprise an aromatic compound selected from the group consisting of anethole, acetylanisole, acetaldehyde, acetylmethylbenzene, 2-acetylpyrazine, 2-acetylpyridine, 2-acetylthiazoline, 2-acetylthiazole, allyl caproate, α-amylcinnamaldehyde, p-anisaldehyde, anisol, dimethylisopropyldithiazine, benzaldehyde, benzyl acetate, l-borneol, butyric acid, butyl acetate, 3-butenylphthalide, decanoic acid, l-carvone, d-carvone, carvone, cis-carvyl acetate, caryophyllene, 1,8-cineole, 1,4-cineole, cinnamyl acetate, citral, citronellal, citronellol, citronellyl acetate, Cumaldehyde, cyclopentadecalactone, α-damascenone, β-damascenone, α-damascenone, β-damascenone, δ-decanoic acid, γ-decanoic acid, dehydromenthyl furanolide, dihydromenthyl furanolide, 2,3-diethylpyrazine, dihydroanethole, dihydrocarvone, dihydrocoumarin, β-dihydroionone, dimethyl anthranilate, dimethyl sulfide, dimethylpyrazine, Sotolon, diphenyl ether, divanillin, 2,4-decadienal, δ-dodecalactone, γ-dodecalactone, acetic acid, ethyl acetate, ethyl butyrate, 2-ethylmethyl butyrate, ethyl hexanoate, ethyl octanoate, ethyl cinnamate, ethyl isobutyrate, ethyl vanillin, ethyl lactate, ethyl maltol, methyl Ethyl thiopropionate, 4-ethylphenol, ethyl isovalerate, eugenol, fench alcohol, furanone, filbertone, raspberry ketone, methyl raspberry ether, furfuryl mercaptan, undecantriene, geraniol, geranyl acetate, geranyl isobutyrate, guaiacol, jasmonate, 2-heptanone, 4-Z-heptenal, γ-caprolactone, γ-heptyl lactone, 3-Z-hexenol, 2-E-hexenol, hexanol, hexyl acetate, 3-Z-hexenyl acetate, 2-E-hexenyl acetate, α-hexyl cinnamaldehyde, 3-Z-hexenyl acetate, dehydrolinalool, indole, α-irone, α-ionone, β-ionone, isoamyl acetate, isoamyl butyrate Esters, isopentyl isovalerate, isobutyl acetate, isobutylthiazole, isobutylaldehyde, isovaleraldehyde, isoeugenol, isomenthone, isopropyl-methoxypyrazine, isobutylmethoxypyrazine, 2,4-isopropylmethylpyrazine, isopulegol, jasminolactone, cis-jasmone, camphor, oxoisophorone, cresol, d-limonene, l-linalool, d-linalool, linalyl acetate, linalool oxide, maltol, methylcyclopentenolone, L-menthone, D-menthone, L-menthol, D-menthol, neomenthol, L-menthyl acetate, D-menthyl acetate, massoia lactone, melonal, 1,8-menthyl mercaptan, 4,7,7-trimethyl-6-thiobicyclo[3.2.1] Octane (1,8-Epithiomenthane), 8,3-thiomenthanone, menthofuranolide, menthadienylacetate, 2,3-methoxymethylpyrazine, methyl anthranilate, methyl salicylate, thymol, methyl butyrate, 2-methylbutyl acetate, methyl cinnamate, 2,3-methyl furanthiol, 2,3-methyltetrahydrofuranthiol, jasmine Methyl lycoside, methyl dihydrojasmonate, methyl thiobutyrate, 1,3-methylthiohexyl acetate, 1,3-methylthiohexanol, methylthiopropionaldehyde, myrtenal, naringin, neral, nerol, neryl acetate, γ-nonalactone, δ-nonalactone, 2-E-nonenal, 6-Z-nonenal, 6-Z-nonenol, nootkatone, dihydronootkatone, 1,3-octenol, γ-octalactone, δ-octalactone, Pelitorine, 1,3-pentenone, amyl acetate, phenylacetaldehyde, phenylethanol, phenylethyl acetate, piperitanat, isopentenyl mercaptan, isopentenyl thioacetate, rose oxide, rubenamine, rubescenamine, sabinene hydrate, skatole, phenyl glycol acetate, terpineol, 4-terpene alcohol, 1,3-thiohexanol, 1,3-thiohexyl acetate, 2,4,4-thiopentanone, Trimethylpyrazine, δ-undecalactone, γ-undecalactone, 2,4-decadienal, 2,4-nonadienal, 2,6-nonadienal, 2,4-undecadienal, vanillin, vinylguaiacol, whiskey lactone, cinnamaldehyde, cinnamyl alcohol, diallyl disulfide, allyl isothiocyanate, hexanal, E-2-hexenal, octanal, decanal, tridecanal, 12-methyltridecanal, α-pinene, β-pinene, piperitone, and mixtures thereof. Oral Composition

[0042] Another object of the present invention relates to a preferred non-therapeutic oral and / or oral care composition, which contains an antimicrobial composition preferably in an amount of about 0.001 to about 1.5% by weight, more preferably about 0.01 to about 0.8% by weight, most preferably about 0.02 to about 0.3% by weight, calculated on the composition.

[0043] Typical examples of suitable oral compositions include toothpaste, mouthwash, (tooth) chewing gum, (hard-boiled) candy and compressed tablets. The preparation and composition of the oral composition are described below: Toothpaste and mouthwash

[0044] Toothpaste or toothpaste cream is generally understood to be a paste preparation of water, thickener, humectant, abrasive or polishing agent, surfactant, sweetener, flavoring agent, deodorant and an agent effective against oral and dental diseases. In the toothpaste according to the present invention, any commonly used polishing agent can be used, such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicate, calcium pyrophosphate, fine-grained synthetic resin, silicon dioxide, aluminum oxide and trihydrated aluminum oxide. Particularly suitable polishing agents for use in toothpastes according to the present invention are fine-grained xerogel silica, hydrogel silica, precipitated silica, trihydrated aluminum oxide and fine-grained α-alumina, or mixtures of these polishing agents. The amount of such polishing agents is preferably about 15% to 40% by weight of the weight of the toothpaste. Preferred wetting agents for toothpastes of the present invention include low molecular weight polyethylene glycol, glycerol, sorbitol or mixtures thereof, in an amount of up to about 50% by weight of the weight of the toothpaste. Among the known thickeners used with the toothpaste according to the present invention, particularly preferred are thickening fine-grained gel silica and nonionic hydrophilic colloids, such as hydroxyethylcellulose, hydroxypropyl guar gum, hydroxyethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol and plant gums, such as tragacanth, agar, carrageenan, gum arabic and xanthan gum. The flavor and aroma required for the preparation according to the present invention can be obtained by adding components (a) and / or (b) and optionally (c). It is also advantageous to add a caries inhibitor in the form of an alkali metal salt of, for example, an alkali metal fluoride, an alkali metal monofluorophosphate or an organic phosphonic acid to the oral preparation. In addition, the oral preparation according to the present invention may contain other standard auxiliaries, such as dyes, preservatives and sunscreens, such as titanium dioxide. For mouthwashes, the oral composition according to the present invention can be easily combined with a water-alcohol solution containing different amounts of essential oils, emulsifiers, astringents and conditioning drug extracts, anti-caries additives and flavoring agents. chewing gum

[0045] Chewing gum generally consists of a water-insoluble base component, a water-soluble component and additives that provide, for example, a particular flavor.

[0046] The water-insoluble matrix, also referred to as "gum base", generally comprises natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, softeners, dyes and optional waxes. The base generally accounts for 5 to 95% by weight of the whole composition, preferably 10 to 50% by weight, more particularly 20 to 35% by weight. In a typical embodiment of the invention, the matrix is ​​composed of 20 to 60% by weight of synthetic elastomers, 0 to 30% by weight of natural elastomers, 5 to 55% by weight of plasticizers, 4 to 35% by weight of fillers, 5 to 35% by weight of softeners and a small amount of additives, such as dyes, antioxidants, etc., provided that they are at most soluble in water in small amounts.

[0047] Suitable synthetic elastomers are, for example, isobutylene / isoprene copolymers ("butyl elastomers") having an average molecular weight (measured by GPC) of 10,000 to 100,000 and preferably 50,000 to 80,000, styrene / butadiene copolymers (styrene:butadiene ratio, for example 1:3 to 3:1), polyvinyl acetate having an average molecular weight (measured by GPC) of 2,000 to 90,000 and preferably 10,000 to 65,000, polyisoprene, polyethylene, vinyl acetate / vinyl laurate copolymers, and mixtures thereof. Examples of suitable natural elastomers are rubbers, such as smoked or liquid latex or guayuls, and natural gums, such as jelutong, lechi caspi, perillo, sorva, massaranduba balata, nispero, rosindinba, chicle, gutta hang kan and mixtures thereof. The choice of synthetic and natural elastomers and the proportions in which they are mixed depend mainly on whether the bubbles are produced using chewing gum ("bubble gum"). Preferably, an elastomer mixture comprising jelutong, chicle, sorva and massanduraba is used.

[0048] In most cases, elastomers are too hard or lack plasticity for satisfactory processing, so it has been found to be advantageous to use special plasticizers, which of course must also meet all requirements related to acceptability as food additives. In this respect, suitable plasticizers are firstly esters of resin acids, for example esters of lower aliphatic alcohols or polyols with fully or partially hydrogenated monomeric or oligomeric resin acids. In particular, methyl esters, glycerides or pentaerythritol esters or mixtures thereof are used for this purpose. Alternatively, terpene resins that can be derived from α-pinene, β-pinene, δ-limonene or mixtures thereof can also be used.

[0049] Suitable fillers or texturizing agents are magnesium or calcium carbonate, ground pumice, silicates, especially magnesium or aluminum silicates, clays, alumina, talc, titanium dioxide, mono-, dicalcium and tricalcium phosphates and cellulosic polymers.

[0050] Suitable softeners or emulsifiers are tallow, hydrogenated tallow, hydrogenated or partially hydrogenated vegetable oils, cocoa butter, partial glycerides, lecithin, triacetin and saturated or unsaturated fatty acids containing 6 to 22, preferably 12 to 18, carbon atoms, and mixtures thereof.

[0051] Suitable dyes and whiteners are, for example, FD&C types, plant and fruit extracts approved for coloring foods, and titanium dioxide.The gum base may also contain waxes or may be wax-free.

[0052] Except water-insoluble gum base, chewing gum formulation contains water-soluble components usually, and it is for example made up of softener, sweetener, filler, spices, flavor enhancer, emulsifier, dyestuff, acidulant, antioxidant etc., and condition is that these compositions have enough solubility in water at least.Therefore, depending on the water solubility of specific representative, each composition can belong to water-insoluble phase and water-soluble phase.But, also can use combination, for example the combination of water-soluble emulsifier and water-insoluble emulsifier, in this case each representative is present in different phases.Water-insoluble components account for 5 to 95 weight % of preparation usually, preferably 20 to 80 weight %.

[0053] Water-soluble softeners or plasticizers are added to chewing gum compositions to improve chewiness and chewiness, and are generally present in the mixture in an amount of 0.5 to 15% by weight. Typical examples are aqueous solutions of glycerol, lecithin and sorbitol, hydrogenated starch hydrolysates or corn syrup.

[0054] Fillers are particularly suitable for the production of low-calorie chewing gums and may be selected from, for example, polydextrose, raftilose, raftilin, fructooligosaccharides (NutraFlora), palatinose oligosaccharides, guar gum hydrolysates (Sun Fiber) and dextrins.

[0055] Chewing gums may additionally contain adjuvants and additives suitable, for example, for dental care, more particularly for controlling dental plaque and gingivitis, such as chlorhexidine, CPC or triclosan. They may also contain pH regulators (such as buffers or urea), anti-caries agents (such as phosphates or fluorides), biological agents (antibodies, enzymes, caffeine, plant extracts), provided that these substances are permitted for use in foods and do not interact undesirably. candy

[0056] Preferred candies according to the present invention are so-called hard candies. Their matrix is ​​usually made of a mixture of sugar and other carbohydrates, and keeps an amorphous or glassy state. This form can be considered as a solid syrup of sugar, usually with up to about 4.5% by weight of moisture, based on the weight of the candy matrix, preferably about 0.5 to about 2.5% by weight, and most preferably about 1.0 to about 1.5% by weight. Such materials usually contain up to 65% by weight of corn syrup, up to 80% by weight of sugar and 0.1 to 5.0% by weight of water. Generally speaking, the ratio of sugar (or other sweeteners suitable for candy recipes) to corn syrup is in the range of about 70:25 to about 45:55, preferably about 60:40. The syrup component is usually prepared by corn syrup with a high fructose content, but other materials may also be included. Other ingredients may also be added, such as flavorings, sweeteners, acidulants, coloring agents, etc.

[0057] Hard boiled candy bases can also be prepared from non-fermentable sugars such as sorbitol, mannitol, xylitol, maltitol, hydrogenated starch hydrolysates, hydrogenated corn syrups, and mixtures thereof. The candy base can contain up to about 95% sorbitol, a mixture of sorbitol and mannitol in a ratio of about 9.5 to 0.5 to up to about 7.5 to 2.5, and up to about 55% hydrogenated corn syrup of the syrup component. Compressed tablets

[0058] According to the present invention, the oral composition may be a compressed tablet containing generally about 0.1 to about 0.6 wt %, preferably about 0.5 wt %, of a liquid flavoring agent. additive

[0059] The oral composition of the present invention may contain additional additives, such as aromatic compounds, sweeteners or vitamins, in an amount of about 0.1 to about 10% by weight. These additives may also represent components of the corresponding medicaments. Flavor compounds

[0060] The aromatic compound is selected from anise alcohol, p-acetylanisole, acetaldehyde, acetylmethylcarbinol, 2-acetylpyrazine, 2-acetylpyridine, 2-acetylthiazoline, 2-acetylthiazole, allyl caproate, α-amylcinnamaldehyde, p-anisaldehyde, anise alcohol, dimethylisopropyldithiazine, benzaldehyde, benzyl acetate, l-borneol, butyric acid, butyl acetate, 3-butenylphthalide, decanoic acid, l-carvone, d-carvone, carvone, cis-carvyl acetate, caryophyllene, 1,8-cineole, 1,4-cineole, cinnamyl acetate, citral, citronellal, citronellol, citronellyl acetate, cuminaldehyde, cyclopentadecalactone, α-damascenone, β-damascenone, α-damascenone, β-damascenone, δ-decalactone, γ-decalactone, de Hydromenthol furanolide, dihydromenthol furanolide, 2,3-diethylpyrazine, dihydroanethole, dihydrocarvone, dihydrocoumarin, β-dihydroionone, methyl o-aminobenzoate, dimethyl sulfide, dimethylpyrazine, fenugreek lactone (sotolone), diphenyl ether, divanillin, 2,4-decadienal, δ-dodecalactone, γ-dodecalactone, acetic acid, ethyl acetate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl hexanoate, ethyl octanoate, ethyl cinnamate, ethyl isobutyrate, ethyl vanillin, ethyl lactate, ethyl maltol, ethyl methylthiopropionate, 4-ethylphenol, ethyl isovalerate, eugenol, fench alcohol, furanone, hazelnut ketone, raspberry ketone, Frambinonmet hylether, furfurylthiol, undecatriene, geraniol, geranyl acetate, geranyl isobutyrate, guaiacol, piperonal, 2-heptanone, 4-Z-heptenal, γ-caprolactone, γ-heptyl lactone, 3-Z-hexenol, 2-E-hexenol, hexanol, hexyl acetate, 3-Z-hexenyl acetate, 2-E-hexenyl acetate, α-hexylcinnamaldehyde, 3-Z-hexenyl hexanoate, dehydrolinalool, indole, α-irone, α-ionone, β-ionone, isoamyl acetate, isoamyl butyrate, isoamyl isovalerate, isobutyl acetate, isobutylthiazole, isobutyraldehyde, isovaleraldehyde, isoeugenol, isomenthone, isopropylmethoxypyrazine, isobutylmethoxypyrazine, 2,4-isopropylmethylpyrazine, iso Pulegol, Jasmine lactone, cis-jasmone, Camphor, Tea ketone, Cresol, D-limonene, l-linalool, d-linalool, linalyl acetate, linalool oxide, maltol, methylcyclopentenolone, L-menthone, D-menthone, L-menthol, D-menthol, neomenthol, L-menthyl acetate, D-menthyl acetate, Masoia lactone, melonal, 1,8-menthyl mercaptan, 1,8-Epithiomenthane, 8,3-thiomenthone, menthyl furan lactone, menthyl acetate, 2,3-methoxymethylpyrazine, methyl anthranilate, methyl salicylate, thymol, methyl butyrate, 2-methylbutyl acetate, methyl cinnamate, 2,3-methyl furanthiol, 2,3-Methyltetrahydrofuranthiol, methyl jasmonate, methyl dihydrojasmonate, methyl thiobutyrate, 1,3-methylthiohexanol acetate, 1,3-methylthiohexanol, methylthiopropionaldehyde, myrtenal, naringin, neral, nerol, neryl acetate, γ-nonalactone, δ-nonalactone, 2-E-nonenal, 6-Z-nonenal, 6-Z-nonenol, nootkatone, dihydronootkatone, 1,3-octenol, γ-octenolactone, δ-octenolactone, pellitol, 1,3-pentenone, amyl acetate, phenylacetaldehyde, phenylethanol, phenylethyl acetate, Piperitanat, isopentenylthiol, isopentenylthiol acetate, rose oxide, Rubenamine, rubescenamine, sabinene hydrate, skatole, phenylethyl acetate, terpineol, 4-terpineol, 1,3-thiohexanol, 1,3-thiohexyl acetate, 2,4,4-thiopentanone, trimethylpyrazine, δ-undecalactone, γ-undecalactone, 2,4-decadienal, 2,4-nonadienal, 2,6-nonadienal, 2,4-undecadienal, vanillin, vinylguaiacol, whiskey lactone, cinnamaldehyde, cinnamyl alcohol, diallyl disulfide, allyl isothiocyanate, hexanal, E-2-hexenal, octanal, decanal, tridecanal, 12-methyltridecanal, α-pinene, β-pinene, piperitone, and mixtures thereof. Sweeteners

[0061] Suitable sweetening substances include natural sources of these substances (component e5), such as sweet carbohydrates or sugars (e.g. sucrose (synonymous with Saccharose), trehalose, lactose, maltose, melezitose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceraldehyde, maltodextrin) or plant preparations containing mainly these carbohydrates (e.g. from sugar beets (Beta vulgaris ssp., sugar fractions, syrups, molasses), from sugar cane (Saccharum officinarum ssp., such as molasses, syrups), from sugar maple (Acer truncatum ssp., such as molasses, syrups), ssp.), from agave (agave concentrate), synthetic / enzymatic hydrolysates of starch or sucrose (e.g., invert syrup, highly concentrated fructose syrup made from corn starch), fruit concentrates (e.g., from apples or pears, apple syrup, pear syrup), sugar alcohols (e.g., erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulcitol, lactitol), proteins (e.g., miraculin, monellin, thaumatin, curculin, brazzein), sweeteners (magap, cyclamate, acesulfame potassium, neohesperidin dihydrochalcone, saccharin sodium salt, Super aspartame, neotame, alitame, sucralose, stevioside, rebaudioside, lugduname, guanidine sweetener (carrelame), sucrononate, sucrooctate, monatin, praeruptolide), certain sweet amino acids (glycine, D-leucine, D-threonine, D-asparagine, D-phenylalanine, D-tryptophan, L-proline), other sweet low molecular substances (such as hernanduxin, dihydrochalcone glycosides, glycyrrhizin, glycyrrhetinic acid monoammonium salt or other glycyrrhetinic acid derivatives), licorice extract (Glycyrrizza glabra ssp.), sweet tongue grass (Lippia dulcis) extract, Momordica ssp. extract or individual substances (especially monk fruit and mogroside obtained therefrom), hydrangea or stevia subspecies (such as Stevia rebaudiana) extract or individual substances. Vitamins

[0062] In another embodiment of the present invention, the composition may include vitamins. Vitamins have a variety of biochemical functions. Some have hormone-like functions, acting as regulators of mineral metabolism (e.g., vitamin D), or regulators of cell and tissue growth and differentiation (e.g., certain forms of vitamin A). Others act as antioxidants (e.g., vitamin E and sometimes vitamin C). Most vitamins (e.g., B vitamins) act as precursors of enzyme cofactors, helping enzymes to function as metabolic catalysts. In this role, vitamins may be tightly bound to enzymes as part of a prosthetic group: for example, biotin is part of an enzyme involved in making fatty acids. Vitamins may also be less tightly bound to enzyme catalysts as coenzymes, which are separable molecules whose function is to carry chemical groups or electrons between molecules. For example, folic acid carries various forms of carbon groups in cells—methyl, formyl, and methylene. Although these roles of assisting enzyme-substrate reactions are the most well-known functions of vitamins, other functions of vitamins are equally important. In the process of the present invention, suitable vitamins are selected from the following group: Vitamin A (retinol, retinal, beta-carotene) Vitamin B1 (thiamine), Vitamin B2 (riboflavin), Vitamin B3 (niacin, niacinamide), Vitamin B5 (pantothenic acid), Vitamin B6 (pyridoxine, pyridoxamine, paridoxal), Vitamin B7 (biotin), Vitamin B9 (folic acid, folinic acid), Vitamin B12 (cyanocobalamin, hydroxocobalamin, methylcobalamin), Vitamin C (ascorbic acid), Vitamin D (cholecalciferol), Vitamin E (tocopherol, tocotrienols), Vitamin K (phylloquinone, menaquinone).

[0063] Preferred vitamins are ascorbic acid and tocopherol.The vitamins may be present in the food composition in an amount of about 0.1 to about 5 wt%, preferably about 0.5 to about 1 wt%. Industrial Applicability

[0064] Another object of the present invention relates to a method for combating microorganisms causing biofilm and / or dental plaque in the oral cavity, the method comprising or consisting of the following steps: (a) providing a mixture as described above; (b) incorporating the mixture into an oral composition; and (c) contacting the oral composition with the oral cavity of a human.

[0065] The invention also encompasses the use of a mixture as described above for oral care applications, i.e. against microorganisms causing biofilm and / or plaque in the oral cavity.In the context of the present invention, oral care applications refer to products such as toothpaste, mouthwash, (dental) chewing gum and confectionery.

[0066] In a preferred embodiment, the mixture comprises carvacrol and menthyl lactate, menthol propylene glycol carbonate, 3-(-) menthoxypropane-1,2-diol or mixtures thereof as flavoring agents or consists of these substances.

[0067] For the sake of good order, it should be emphasized that all the preferred embodiments, scopes, combinations, etc. mentioned above also refer to the claimed methods and uses. Therefore, there is no need to repeat them. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 The results of the relative biofilm activity after treatment with various flavoring agents are shown to be effective in reducing oral biofilm. 100% represents the activity of the untreated control biofilm. Figure 2 Shown is the concentration-dependent reduction of oral biofilm after treatment with carvacrol and oregano oil, respectively. The graph shows the relative biofilm activity remaining after treatment compared to the control. DETAILED DESCRIPTION Examples 1 to 23 (Tables 1-3) Determination of in vitro minimum inhibitory concentration (MIC) data

[0068] MIC data were evaluated based on the DIN 58940-8 microdilution method. In the experiment, three relevant bacteria present in oral biofilms were selected: Streptococcus mutans (DSM 20523, ATCC 25175), Porphyromonas gingivalis (DSM 20709, ATCC33277) and Prevotella intermedia (DSM 20706, ATCC25611).

[0069] All test organisms were cultured in appropriate complex media and under anaerobic and / or microaerobic conditions. Each test substance was applied in technical triplicate to 96 microtiter plates in a total volume of 300 μL per well. The inoculum was transferred directly from a glycerol stock solution or a freshly prepared preculture. Thus, 15 mL reagent tubes were filled with the specific complex growth medium and inoculated with a skim milk stock of a single strain. Incubations were performed at 37 °C for up to 48 h until the OD 620 >0.1-1.0. The suspension was monitored by microscopy. In both cases, the bacteria were transferred and diluted into fresh complex medium in a 96-well plate.

[0070] The test substance is a pure material or a mixture. The mixture contains the cooling compound according to the claim and an aromatic component. In addition, these effective structural units can be included in the aromatic composition. Therefore, a natural equivalent (synthetic) substrate (substrate natural equivalent A / B) and / or a natural substrate preparation (substrate natural A / B) can be added.

[0071] The mixture contains either carvacrol (synthetic material) or natural oregano oil, with typical carvacrol contents ranging from 50-80%.

[0072] The test substances were dissolved 100-fold in dimethyl sulfoxide (DMSO) and diluted directly on a 96-well plate. Appropriate concentrations of farnesol and / or triclosan were used as negative controls at 1 to 100 ppm. Untreated medium controls were used as growth controls. The test plates were incubated at 37°C for 16-24 hours. At the end of the experiment, the OD values ​​were measured optically using a Sunrise photometer (TECAN, Austria). 620 The growth was determined by quantifying the value of the test substance. The mean of the triplicates was calculated and normalized with the blank value (growth medium with or without the test substance). The growth of the treated wells was evaluated relative to the growth control. The minimum inhibitory concentration (MIC) was defined as the lowest concentration (in ppm) that completely inhibited bacterial growth.

[0073] The synergistic effect is calculated using the following formula. This formula can be modified based on the number of components in each mixture. MIC stands for minimum inhibitory concentration and is expressed in parts per million [ppm]. MICmix = MIC value of the mixture [ppm] PA = percentage of component A [%] MIC A = MIC value of component A [ppm] PB = percentage of component B [%] MIC B = MIC value of component B [ppm] If the resulting value is below 1, synergy is given. In vitro biofilm model

[0074] The experiment was performed according to the methods described in WO2018 / 033211 and Kistler et al. (Kistler et al., 2015).

[0075] Up to 50 subjects were recruited for saliva donation. Participants were aged between 18 and 65 years and in good health. Subjects who had taken antibiotics, consumed antimicrobial foods such as garlic in the past 24 hours, and / or had any systemic illness that could affect their immune or inflammatory status were excluded from the study. Fresh morning saliva from all donors was selected and pooled. All volunteers were asked not to drink, eat, or brush their teeth before spitting saliva into a sterile universal tube.

[0076] The Calgary Biofilm Device (CBD) was originally developed for medical use. It is commercially available as an MBEC (minimum biofilm eradication concentration) biofilm inoculum, suitable as a basis for biofilm studies (Kistler et al., 2015; Ceri et al., 1999). The 96 pegs of the device cover are coated with hydroxyapatite and imitation teeth. This is mounted into a second 96-well plate so that the pegs are in contact with saliva. The CBD is incubated at 37°C under anaerobic conditions for 18 h. Afterwards, the cover is transferred to a new bottom plate containing oral care medium (brain heart infusion broth (Merck) supplemented with porcine gastric mucin (1 g / L), heme (10 mg / L) and menadione (0.5 mg / L). The growth medium is changed every day.

[0077] Stock solutions of all test substances were prepared in dimethyl sulfoxide (DMSO). For working concentrations, the stock solutions were diluted in sodium chloride solution or other solvents. If necessary, the treatment can be carried out in an ultrasonic bath or a heating block. Pure sodium chloride solution was used as a positive biofilm growth control. The treatment was performed 4 times over 2 days for 2 min each time at 37 °C and 300 rpm. After the treatment, the pegs were washed with pure sodium chloride solution under the same conditions and then transferred to the growth medium again. Six replicates were performed on each plate for each test substance and concentration. Finally, the pegs were washed again and the microbial activity was quantified photometrically by hydrolysis of fluorescein diacetate (FDA). FDA is converted to fluorescein by protease, lipase and esterase activities in the biofilm, so the quantification of fluorescein represents the activity of the biofilm.

[0078] Tables 1 to 3 provide the results of the minimum inhibitory concentrations of various mixtures of carvacrol or oregano oil with physiological cooling agents and the associated synergy index. Figure 1 The relative biofilm activity results of several single component treatments are shown.

[0079] refer to Kistler, James O.; Pesaro, Manuel; Wade, William G. (2015): Development and pyrosequencing analysis of an in-vitro oral biofilm model. BMC microbiology15, p.24. Ceri, H.; Olson, ME; Stremick, C.; Read, RR; Morck, D.; Buret, A. (1999): The Calgary Biofilm Device: new technology for rapid determination of antibioticsusceptibilities of bacte-rial biofilms. Journal of clinical microbiology 37(6), p.1771–1776. Table 1 The antimicrobial efficacy and synergy of various combinations were calculated for different strains using the measured MIC value of the mixture [ppm] (MIC mix, [ppm]), the measured MIC value of component A (MIC A, [ppm]), the percentage of component A in the mixture (PA), the measured MIC value of component B (MIC B, [ppm]), the percentage of component B in the mixture (PB), and the calculated synergy index (SI) Table 2 Antimicrobial efficacy and synergistic effect of a specific synthetic mixture (product example), calculated using the measured MIC value of the mixture [ppm] (MIC mix, [ppm]), the measured MIC value of component A (MIC A, [ppm]), the percentage of component A in the mixture (PA), the measured MIC value of component B (MIC B, [ppm]), the percentage of component B in the mixture (PB), the measured MIC value of component C (MIC C, [ppm]), the percentage of component C in the mixture (PC), and the calculated synergistic index (SI) Table 3 Antimicrobial efficacy and synergy of a specific natural mixture (product example), calculated using the measured MIC value of the mixture [ppm] (MIC mix), the measured MIC value of component A (MIC A), the percentage of component A in the mixture (PA), the measured MIC value of component B (MIC B), the percentage of component B in the mixture (PB), the measured MIC value of component C (MIC C), the percentage of component C in the mixture (PC), and the calculated synergy index (SI) Formulation Examples

[0080] Tables 4 to 17 below provide various examples of oral compositions

[0081] Table 4 Chewing gum, sugar-free; all contents are expressed as percentages by weight

[0082] Table 5 Toothpaste; all amounts are in percent by weight

[0083] Table 6 Dentifrice containing therapeutic doses of fluoride; all amounts are in percent by weight Element <![CDATA[SnF2 toothpaste]]> NaF toothpaste NaMFP Toothpaste Sorbitol (70%) 46.00 65.51 - USP water 26.66 13.78 60.01 Sodium fluoride - 0.24 - Stannous fluoride 0.45 - - Sodium monofluorophosphate - - 0.76 Stannous chloride 0.56 - - Sodium Citrate 1.55 - - Sodium Gluconate 1.3 - - Trisodium phosphate - 1.10 0.42 Monosodium phosphate - 0.42 0.08 Tetrasodium pyrophosphate - - 0.60 Hydrated Silica 17.50 15.00 2.62 Calcium carbonate - - 32.00 Carbomer - 0.30 - Cellulose gum - 0.75 0.92 Carrageenan 1.05 - 1.20 Xanthan gum,NF 0.61 - - Saccharin Sodium 0.25 0.25 0.25 Sodium lauryl sulfate 1.29 1.29 1.29 Sodium hydroxide (50%) 0.75 - - Titanium Dioxide - 0.55 - Flavoring 1.17 0.76 0.80 Mixture Example 15 0.03 Mixture Example 15 0.04

[0084] Table 7 Dentifrice containing therapeutic doses of fluoride; all amounts are in percent by weight Element <![CDATA[SnF2 toothpaste]]> NaF toothpaste NaMFP Toothpaste Sorbitol (70%) 46.00 65.51 - USP water 26.66 13.78 60.01 Sodium fluoride - 0.24 - Stannous fluoride 0.45 - - Sodium monofluorophosphate - - 0.76 Stannous chloride 0.56 - - Sodium Citrate 1.55 - - Sodium Gluconate 1.3 - - Trisodium phosphate - 1.10 0.42 Monosodium phosphate - 0.42 0.08 Tetrasodium pyrophosphate - - 0.60 Hydrated Silica 17.50 15.00 2.62 Calcium carbonate - - 32.00 Carbomer - 0.30 - Cellulose gum - 0.75 0.92 Carrageenan 1.05 - 1.20 Xanthan gum,NF 0.61 - - Saccharin Sodium 0.25 0.25 0.25 Sodium lauryl sulfate 1.29 1.29 1.29 Sodium hydroxide (50%) 0.75 - - Titanium Dioxide - 0.55 - Flavoring 1.17 0.76 0.80 Mixture Example 17 0.03 Mixture Example 17 0.04 Mixture Example 17 0.05

[0085] Table 8 Dentifrice containing therapeutic doses of fluoride; all amounts are in percent by weight Element <![CDATA[SnF2 toothpaste]]> NaF toothpaste NaMFP Toothpaste Sorbitol (70%) 46.00 65.51 - USP water 26.66 13.78 60.01 Sodium fluoride - 0.24 - Stannous fluoride 0.45 - - Sodium monofluorophosphate - - 0.76 Stannous chloride 0.56 - - Sodium Citrate 1.55 - - Sodium Gluconate 1.3 - - Trisodium phosphate - 1.10 0.42 Monosodium phosphate - 0.42 0.08 Tetrasodium pyrophosphate - - 0.60 Hydrated Silica 17.50 15.00 2.62 Calcium carbonate - - 32.00 Carbomer - 0.30 - Cellulose gum - 0.75 0.92 Carrageenan 1.05 - 1.20 Xanthan gum,NF 0.61 - - Saccharin Sodium 0.25 0.25 0.25 Sodium lauryl sulfate 1.29 1.29 1.29 Sodium hydroxide (50%) 0.75 - - Titanium Dioxide - 0.55 - Flavoring 1.17 0.76 0.80 Mixture Example 19 0.03 Mixture Example 19 0.04 Mixture Example 19 0.05

[0086] Table 9 Toothpaste containing a mixture of a subtherapeutic dose of fluoride and a subtherapeutic dose of a second antiplaque agent, all amounts being expressed in weight percent

[0087] Table 10 Exemplary formulation of toothpaste; all amounts are in weight percent

[0088] Table 11 Exemplary formulation of toothpaste; all amounts are in weight percent

[0089] Table 12 Exemplary formulation of toothpaste; all amounts are in weight percent

[0090] Table 13 Exemplary formulation of toothpaste; all amounts are in weight percent

[0091] Table 14 Mouthwash concentrate; all amounts are in weight percent

[0092] Table 15 Mouthwash containing therapeutic amounts of fluoride; all amounts are in percent by weight Element Mouthwash containing NaF Mouthwash containing NaF USP water 99.105 99.105 Propylene glycol 0.500 0.500 Sodium fluoride 0.020 0.020 Trisodium phosphate dodecahydrate - - Monosodium phosphate monohydrate - - Sodium hydrogen phosphate heptahydrate 0.000 0.000 Polysorbate 80 0.100 0.100 Saccharin Sodium - - Sodium hydroxide (50%) - - Flavoring 0.100 0.100 benzoic acid 0.090 0.090 Sodium Benzoate 0.020 0.020 Phosphoric acid 0.020 0.020 Sucralose 0.040 0.040 Mixture Example 19 0.005 Mixture Example 21 0.005

[0093] Table 16 Hard candies, sugar-free; all amounts are by weight

[0094] Table 17 Hard candy; all amounts are in percent by weight

Claims

1. An antimicrobial mixture comprising or (essentially) consisting of the following ingredients: (a) at least one flavoring agent, and (b) at least one physiological cooling agent, The flavoring agent group includes unsaturated 6-membered ring structures of the following formulas (I) to (IX): wherein R, R1, R2 and R3 independently of one another represent hydrogen, C1-C3 alkyl or C3 alkenyl, C1-C3 alkoxy or acetate, and n represents 0 or 1.

2. The mixture according to claim 1, wherein the unsaturated six-membered ring structure is selected from the group consisting of carvacrol, thymol, eugenyl acetate, dianthramide B, eugenol, myrtenol, cumene alcohol and mixtures thereof, and essential oils containing at least one of the structures.

3. The mixture according to claim 1, wherein the physiological cooling agent is selected from the group consisting of:

4. The mixture according to claim 1, wherein the flavoring agent (a) is carvacrol and the physiological cooling agent (b) is menthyl lactate, menthol propylene glycol carbonate, 3-(-) menthoxypropane-1,2-diol and mixtures thereof.

5. The mixture according to claim 1, further comprising at least one aromatic compound, wherein the aromatic compound is preferably selected from the group consisting of anethole, acetylanisole, acetaldehyde, acetylmethyl alcohol, 2-acetylpyrazine, 2-acetylpyridine, 2-acetylthiazoline, 2-acetylthiazole, allyl caproate, α-amylcinnamaldehyde, p-anisaldehyde, anisol, dimethylisopropyldithiazine, benzaldehyde, benzyl acetate, l-borneol, butyric acid, butyl acetate, 3-butenylphthalide, decanoic acid, l-carvone, d-carvone, carvone, cis-carvyl acetate, caryophyllene, 1,8-cineole, 1,4-cineole, cinnamyl acetate, citral, citronellal, citronellol, acetate Citronellal, Cumaldehyde, Cyclopentadecalactone, α-damascenone, β-damascenone, α-damascenone, β-damascenone, δ-decalactone, γ-decalactone, Dehydromenthafuranolactone, Dihydromenthafuranolactone, 2,3-diethylpyrazine, Dihydroanethole, Dihydrocarvone, Dihydrocoumarin, β-dihydroionone, Dimethyl anthranilate, Dimethyl sulfide, Dimethylpyrazine, Sotolon, Diphenyl ether, Divanillin, 2,4-decadienal, δ-dodecalactone, γ-dodecalactone, Acetic acid, Ethyl acetate, Ethyl butyrate, 2-ethylmethyl butyrate, Ethyl hexanoate, Ethyl octanoate, Ethyl cinnamate, Ethyl isobutyrate, Ethyl vanillin, Ethyl lactate, Ethyl maltol , ethyl methylthiopropionate, 4-ethylphenol, ethyl isovalerate, eugenol, fenchol, furanone, filbertone, raspberry ketone, methyl raspberry ether, furfuryl mercaptan, undecantriene, geraniol, geranyl acetate, geranyl isobutyrate, guaiacol, jasmonate, 2-heptanone, 4-Z-heptenal, γ-caprolactone, γ-heptyl lactone, 3-Z-hexenol, 2-E-hexenol, hexanol, hexyl acetate, 3-Z-hexenyl acetate, 2-E-hexenyl acetate, α-hexyl cinnamaldehyde, 3-Z-hexenyl acetate, dehydrolinalool, indole, α-irone, α-ionone, β-ionone, isoamyl acetate, isobutyrate amyl ester, isopentyl isovalerate, isobutyl acetate, isobutylthiazole, isobutylaldehyde, isovaleraldehyde, isoeugenol, isomenthone, isopropyl-methoxypyrazine, isobutylmethoxypyrazine, 2,4-isopropylmethylpyrazine, isopulegol, jasminolactone, cis-jasmone, camphor, oxoisophorone, cresol, d-limonene, l-linalool, d-linalool, linalyl acetate, linalool oxide, maltol, methylcyclopentenolone, L-menthone, D-menthone, L-menthol, D-menthol, neomenthol, L-menthyl acetate, D-menthyl acetate, massoia lactone, melonal, 1,8-menthyl mercaptan, 4,7,7-trimethyl-6-thiobicyclo[3.2.1] Octane (1,8-Epithiomenthane), 8,3-thiomenthanone, menthofuranolide, menthadienylacetate, 2,3-methoxymethylpyrazine, methyl anthranilate, methyl salicylate, thymol, methyl butyrate, 2-methylbutyl acetate, methyl cinnamate, 2,3-methyl furanthiol, 2,3-methyltetrahydrofuranthiol, jasmine Methyl lycoside, methyl dihydrojasmonate, methyl thiobutyrate, 1,3-methylthiohexyl acetate, 1,3-methylthiohexanol, methylthiopropionaldehyde, myrtenal, naringin, neral, nerol, neryl acetate, γ-nonalactone, δ-nonalactone, 2-E-nonenal, 6-Z-nonenal, 6-Z-nonenol, nootkatone, dihydronootkatone, 1,3-octenol, γ-octalactone, δ-octalactone, Pelitorine, 1,3-pentenone, amyl acetate, phenylacetaldehyde, phenylethanol, phenylethyl acetate, piperitanat, isopentenyl mercaptan, isopentenyl thioacetate, rose oxide, rubenamine, rubescenamine, sabinene hydrate, skatole, phenyl glycol acetate, terpineol, 4-terpene alcohol, 1,3-thiohexanol, 1,3-thiohexyl acetate, 2,4,4-thiopentanone, Trimethylpyrazine, δ-undecalactone, γ-undecalactone, 2,4-decadienal, 2,4-nonadienal, 2,6-nonadienal, 2,4-undecadienal, vanillin, vinylguaiacol, whiskey lactone, cinnamaldehyde, cinnamyl alcohol, diallyl disulfide, allyl isothiocyanate, hexanal, E-2-hexenal, octanal, decanal, tridecanal, 12-methyltridecanal, α-pinene, β-pinene, piperitone, and mixtures thereof.

6. The mixture according to claim 1, further comprising at least one solvent and / or at least one aromatic compound.

7. The mixture according to claim 5, wherein the solvent is selected from the group consisting of water, ethanol, glycerol, 1,2-propylene glycol, 1,3-propylene glycol, triacetin, vegetable oils, triglycerides and triethyl citrate and mixtures thereof, preferably in an amount of 5 to about 95 weight %.

8. The mixture of claim 1, wherein components (a) and (b) are present in a weight ratio of about 10:90 to about 90:

10.

9. The mixture according to claim 1 is active against strains selected from Porphyromonas gingivalis, Prevotella intermedia and / or Streptococcus mutans.

10. The mixture according to claim 1 is active against oral biofilm and / or dental plaque.

11. An oral composition comprising an effective amount of the antimicrobial mixture according to claim 1.

12. The composition of claim 11, comprising from about 0.001 to about 1.5 weight percent of the antimicrobial mixture of claim 1, based on the composition.

13. The composition according to claim 11 is a toothpaste, a mouthwash, a chewing gum or a compressed tablet.

14. A method for combating microorganisms causing biofilm and / or dental plaque in the oral cavity, the method comprising or consisting of the following steps: (a) providing a mixture according to claim 1; (b) incorporating the mixture into an oral composition; and (c) contacting the oral composition with the oral cavity of a human.

15. Use of the mixture according to claim 1 for oral care.

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