Flavor formulation containing menthol

Abstract

It is proposed that the fragrance preparation contains (a) a compound of the formula (I) which represents a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing 1 to 4 carbon atoms, R2represents hydrogen or hydroxyl, and R3represents hydrogen, methyl or methoxyl, or an essential oil containing one or more compounds of the formula (I), and (b) at least one menthol compound.

Description

Invention Field

[0001] This invention belongs to the field of fragrance substances and relates to novel formulations containing selected fragrances and cooling substances, as well as oral formulations containing these mixtures. Existing technology

[0002] 4-Allyl-2-methoxyphenol, known as an aromatic and flavoring substance with a hot and spicy aroma, is a component of various essential oils such as clove oil (70 to 95% by weight), allspice and allspice leaf oil (60 to 90% by weight), bay leaf oil (50 to 60% by weight), or cinnamon oil (5 to 95% by weight). It is also found in laurel, basil, banana, cherry, and nutmeg. Eugenol, and especially clove oil, is commonly used in oral preparations, particularly in oral care products, due to its antiviral, antibacterial, and antioxidant properties. For example, small amounts of eugenol can enhance the antibacterial properties of thymol and terpineol (EP2480090 B1, UNILEVER).

[0003] However, a drawback is that many people dislike the taste of eugenol or clove oil because they associate it with unpleasant experiences at the dentist. In fact, eugenol is also an essential component of so-called zinc oxide-eugenol binder—which is frequently used in dentistry. Structurally similar substances, such as anethole, thymol, or carvacrol, have the same problem.

[0004] Another drawback of these substances is that they not only produce the desired hot and spicy taste impression, but are also perceived by many consumers as burning or even pain.

[0005] The subject of this invention is therefore to alter the flavor impression of the substance or the essential oil containing the substance, thereby enhancing the hot and spicy impression and suppressing the burning-pain impression. Summary of the Invention

[0006] Therefore, the first subject of this invention relates to flavoring preparations containing...

[0007] (a) Compound of formula (I)

[0008]

[0009] R1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 4 carbon atoms, R2 represents hydrogen or hydroxyl, and R3 represents hydrogen, methyl, or methoxy.

[0010] Essential oils or containing one or more compounds of formula (I), and

[0011] (b) At least one menthol compound.

[0012] Surprisingly, it has been found that the addition of menthol compounds, particularly menthol, menthyl acetate, and especially a mixture of menthol and menthyl acetate, fully satisfies the aforementioned objectives. This mixture also provides a hot sensation, but without the burning or pain, and is only vaguely associated with unpleasant experiences at the dentist.

[0013] Compounds of formula (I) and essential oils

[0014] Within this invention, compounds of formula (I) with R1 being -C(CH3)2, -CH2-CH=CH2, or -CH=CH-CH groups are preferred. Structurally, it is also preferred that R2 and R3 are not both hydrogen atoms.

[0015] The specific form of the compound of formula (I):

[0016]

[0017] In addition to the basic structure of eugenol, the essential oils mentioned at the beginning of the text are also considered as components (a), namely allspice oil, allspice leaf oil, laurel leaf oil, cinnamon oil, laurel oil, nutmeg oil, and especially clove oil.

[0018] Anethole is a component of, for example, fennel oil. Thymol and its isomer carvacrol are components of thyme, oregano, and savory essential oils.

[0019] For clarity, it should be noted that in addition to single compounds of formula (I), mixtures, particularly mixtures of eugenol, anethole, thymol, and / or carvacrol, may also be used. The same applies to essential oils—such as those mentioned above—which contain one or more compounds of formula (I), particularly eugenol, anethole, thymol, and / or carvacrol, in any desired proportion.

[0020] Menthol and Menthol Compounds

[0021] The cooling substance that can be used in this invention and constitutes group (b) is—in addition to menthol itself—selected from, for example, group including menthol methyl ether, menthone glycerol acetal (FEMA GRAS) 1Menthone glycerol ketal (FEMA GRAS 3807), menthyl lactate (FEMA GRAS 3748), menthyl glycol carbonate (FEMA GRAS 3805), menthyl propylene glycol carbonate (FEMA GRAS 3806), N-ethyloxane menthyl ester, menthyl succinate monomenthyl ester (FEMA GRAS 3810), menthyl glutamate monomenthyl ester (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849), and menthyl alkyl carbonates and amides WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30 and mixtures thereof.

[0022] The first important representative of this type of substance constituting component (b) is menthyl succinate (FEMA GRAS 3810), which was patented by Brown & Williamson Tobacco Corp. in 1963 (US 3,111,127) and is the subject of patents US 5,725,865 and 5,843,466 (V. Mane Fils) as a cooling agent. Not only succinates, but also the analogue menthyl glutamate (FEMA GRAS 4006) is an important representative of menthyl esters based on di- or polycarboxylic acids.

[0023]

[0024] Examples of the use of such substances can be found in documents such as WO 2003 043431 (Unilever) or EP 1332772 A1 (IFF).

[0025] The next preferred group of important menthol compounds of the present invention includes menthol and polyols, such as ethylene glycol, glycerol, or carbonates of carbohydrates, such as menthol glycol carbonate. Menthol Propylene Glycol Carbonate 2-Methyl-1,2-propanediol menthol carbonate (FEMA GRAS 3849) or the corresponding sugar derivative:

[0026]

[0027]

[0028] The use of the substance as a cooling agent for cigarettes is the subject of, for example, US3,419,543 (Mold et al.) in 1968; and its use as a physiological cooling agent is claimed in DE4226043A1 (H&R).

[0029] In this invention, the preferred menthol compound is menthyl lactate. Especially menthone glycerol acetal (FEMA GRAS 3807) or menthone glycerol ketal (FEMA GRAS 3808), which are... The name MAG is sold on the market.

[0030]

[0031] The former structure is obtained via esterification of lactic acid and menthol, while the latter structure is obtained via acetalization of menthone and glycerol (see DE 2608226A1, H&R). This class of compounds also includes 3-(l-menthoxy)-1,2-propanediol, also known as Cooling Agent 10 (FEMA GRAS 3784, see US6,328,982, TIC), and 3-(l-menthoxy)-2-methyl-1,2-propanediol (FEMA GRAS 3849), which has an additional methyl group.

[0032]

[0033] The preparation of 3-(l-menthoxy)-1,2-propanediol was carried out, for example, according to the following scheme starting with menthol (see US 4,459,425, Takagaso):

[0034]

[0035] Alternative routes, in which menthol reacts with epichlorohydrin in the first step, are described in US 6,407,293 and US 6,515,188 (Takagaso). An overview of preferred menthol compounds characterized by CO bonds is given below.

[0036]

[0037] Among these substances, menthone glycerol acetal / ketal, menthyl lactate, and menthyl ethylene glycol carbonate or menthyl propylene glycol carbonate have proven to be particularly preferred, as indicated by the applicant. MGA, ML MGC and The name MPC is sold on the market.

[0038] Also suitable are two cooling substances: EC-180 (FEMA GRAS 4496) and EC-190 (FEMA GRAS 4549).

[0039]

[0040] Menthol compounds with a C-C bond at position 3 were first developed in the 1970s, and numerous representative examples of these menthol compounds can be used according to the present invention. These substances are commonly referred to as WS types. The basic substance is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1). All other WS types, such as the preferred WS-3, WS-4, WS-5, WS-12, WS-14, and WS-30 of the present invention, are derived from this structure. The following two figures show the synthetic routes:

[0041]

[0042] For example, US 4,157,384 describes esters derived from WS-1, and J.Soc.Cosmet.Chem.S.185-200 (1978) describes the corresponding N-substituted amides.

[0043] Fragrance preparations

[0044] In a preferred embodiment, the formulation may contain components (a) and (b) in a weight ratio of about 80:20 to about 99:1, and more preferably about 85:15 to about 95:5. If a mixture of menthol and menthyl acetate is used as a component, the weight ratio of the two substances may advantageously be from 99:1 to 1:99, preferably from about 80:20 to 20:80, and particularly from about 60:40 to about 40:60.

[0045] Specially selected flavoring preparations contain

[0046] (a) 80 to 99% by weight of a compound of formula (I) or an essential oil containing one or more compounds of formula (I),

[0047] (b1) 1 to 20% by weight of menthol, and

[0048] (b2) 1 to 20% by weight of menthyl acetate,

[0049] The premise is that the dosage given in each case is added to 100% by weight. This limitation clearly excludes all mixing ratios where the sum does not reach 100% by weight, and a person skilled in the art can choose any mixing ratio that satisfies the above teachings without any inventive steps. See also the embodiments.

[0050] Industrial application

[0051] Another subject of the invention relates to oral formulations containing the aforementioned flavoring mixture. These formulations can be food, pharmaceutical, or oral and dental care preparations, with a dynamic transition between the components. Chewables can be used, for example, as candy or as a cold medicine, and chewing gum can also be used as a refreshing snack or for medical dental care.

[0052] oral preparations

[0053] Typical examples of food products containing the formulations according to the present invention are hard caramel, chewing candy, or gum.

[0054] Typical examples of pharmaceutical preparations containing the formulations according to the present invention are cold syrups, cold sprays, or cold candies.

[0055] Typical examples of pharmaceutical preparations containing the formulations according to the present invention are toothpaste, mouthwash, or medicated chewing gum.

[0056] The oral formulations described above may contain about 0.5 to about 5% by weight, and particularly about 1 to about 2.5% by weight, of a mixture of cooling substances—based on the final formulation. Adjuvants and additives that may also be present in the oral formulations are described below.

[0057] Food preparations

[0058] Foods containing the flavoring mixture according to the invention are typically hard caramel, chewable candy, or lollipops. The most important additives in these products are sweeteners, especially those without sugar. Furthermore, flavorings and food colorings should be mentioned first.

[0059] sweeteners

[0060] Carbohydrates, especially sugars, are the first considerations for sweeteners or sweeteners, such as sucrose, trehalose, lactose, maltose, melitriose, maltotriose, paraginose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceraldehyde, or maltodextrin. Plant compounds containing these substances are also suitable, such as those based on beets (Beta vulgaris ssp., sugar fractions, syrups, molasses), cane sugar (Saccharum officinarum ssp., molasses, cane syrup), maple syrup (Acer ssp.), or agave plants (agave syrup).

[0061] It is also worth considering

[0062] Synthetic, namely, the usual enzymatic starch or sugar hydrolysate (invert sugar, fructose syrup);

[0063] • Concentrated fruit juice (e.g., apple or pear-based);

[0064] Sugar alcohols (e.g., erythritol, threitol, arabinitol, ribitol, xylitol, sorbitol, mannitol, galactitol, lactitol);

[0065] • Proteins (e.g., Miraculin, Monellin, Thaumatin, Curculin, Brazzein);

[0066] Sweeteners (e.g., Magap, sodium cyclohexylsulfamate, acesulfame potassium, neohesperidin dihydrochalcone, sodium saccharin, aspartame, super aspartame, neotam, alitam, sucralose, steviol glycoside, rebaudioside, lugduname, carrelame, sucrononate, sucrooctate, mononitin, phenylodulcin));

[0067] • Sweet-tasting amino acids (such as glycine, D-leucine, D-threonine, D-aspartic acid, D-phenylalanine, D-tryptophan, L-proline);

[0068] Other small molecules with a sweet taste, such as hernandulcin, dihydrochalconglykoside, glycyrrhizin, glycyrrhetic acid, their derivatives and salts, licorice extract (Glycyrrhizza glabra ssp.), Lippiadulcis extract, Momordica ssp. extract, or

[0069] • Individual substances such as monk fruit and its derivatives, such as mogroside, hydrangeadulcis, or phytosalicylate extracts.

[0070] Other flavoring substances

[0071] This invention also particularly permits the use of other flavoring substances having ester, aldehyde, or lactone structures in oral formulations, which degrade particularly rapidly in the presence of titanium dioxide and under the influence of light. Therefore, this invention also provides improved stability, especially the storage stability of flavoring substances.

[0072] The oral formulations according to the present invention may contain one or more other flavoring substances. Typical examples include: acetophenone, allyl hexanoate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, β-ionone, butyl butyrate, butyl hexanoate, butylphenoxylate, carvone, camphene, eugenol, cinnamyl acetate, citral, citronellol, citronellol, citronellol acetate, cyclohexyl acetate, cymene, damascone, and decanol. Dihydrocoumarin, dimethyl aminobenzoate, dodecyl lactone, ethoxyethyl acetate, ethyl butyric acid, ethyl butyrate, ethyl decanoate, ethyl hexanoate, ethyl crotonate, ethyl furanone, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptaate, 4-(p-hydroxyphenyl)-2-butanone, γ-decyl lactone, geraniol, geraniyl acetate, grapefruit aldehyde, methyl dihydrojasmone (e.g.) Piperaldehyde, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-hexenoic acid, trans-3-hexenoic acid, cis-2-hexenyl acetate, cis-3-hexenyl acetate, cis-3-hexanoate, trans-2-hexanoate, cis-3-carboxylate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexyl acetate, cis-3-carboxylate, p-hydroxybenzylacetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool oxide Linaloyl acetate, menthol, mentholatum, methyl aminobenzoate, methylbutanol, methylbutyric acid, 2-methylbutyl acetate, methyl hexanoate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenol, 6,5,2-methylheptenone, methyl dihydrojasmone, methyl jasmone, 2-methyl methylbutyrate, 2-methyl-2-pentenic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexanol acetate, nerol, nerol acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, cedarone, δ-octanolide, γ-octanolide, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, acetic acid 3-Octyl ester, palmitic acid, paraldehyde, non-brownene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperaldehyde, propionaldehyde, propyl butyrate, pulehleone, pulehleol, sweet orange aldehyde, thiols, terpinene, terpineol, isoterpinene, 8,3-thiomenthone, 4,4,2-thiomethylpentanone, thymol, δ-undecyl lactone, γ-undecyl lactone, valencene, valeric acid, vanillin, 3-hydroxybutanone, ethyl vanillin, ethyl vanillyl isobutyrate (=3-ethoxy-4-isobutoxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives (preferably cyclohofuranone (=2-ethyl-4-hydroxy-5-methyl-3-) (2H)-furanone), high-furanone (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and maltol derivatives (preferably ethyl maltol), coumarin and its derivatives, γ-lactones (preferably γ-undecyllactone, γ-nonyllactone, γ-decyllactone), δ-lactones (preferably 4-methyl-δ-decyllactone, masoyllactone, δ-decyllactone, tuberolactone), methyl sorbate, bisvanillin, 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-Dimethyl-2(5H)-furanone, isoamyl acetate, ethyl butyrate, n-butyl butyrate, isoamyl butyrate, 3-methyl-ethyl butyrate, ethyl hexanoate, allyl hexanoate, n-butyl hexanoate, ethyl octanoate, ethyl 3-methyl-3-phenyldehydroglyceroate, ethyl 2-trans-4-cis-decadienyl ester, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptene -1-aldehydes and phenylhexenal, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furanyl)disulfide, furfuryl mercaptan, methyl thiopropionaldehyde, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2-acetyl-1-pyrrolidone, 2-methyl-3- Ethylpyrazine, 2-Ethyl-3,5-dimethylpyrazine, 2-Ethyl-3,6-dimethylpyrazine, 2,3-Diethyl-5-methylpyrazine, 3-Isopropyl-2-methoxypyrazine, 3-Isobutyl-2-methoxypyrazine, 2-Acetylpyrazine, 2-Pentylpyridine, (EE)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-Undecenal, 12-Methyltridecaldehyde, 1-Penten-3-one, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2(5H)-furanone, cinnamaldehyde, cinnamyl alcohol, methyl salicylate, isoprene alcohol, and (not specifically listed) stereoisomers, enantiomers, structural isomers, diastereomers, cis / trans-isomers, or epimers of these substances.

[0073] Flavor enhancer

[0074] Oral formulations—such as flavoring mixtures—may contain other flavoring substances to enhance the taste impression of saltiness, optionally mild sourness, and / or umami. Therefore, the compositions or flavoring mixtures according to the invention can be used in combination with at least one other suitable substance for enhancing the pleasant taste impression (saltiness, saltiness, optionally mild sourness). Preferred compounds are salty compounds and compounds that enhance saltiness. Preferred compounds are disclosed in WO 2007 / 045566. Umami compounds, such as those described in WO 2008 / 046895 and EP 1 989 944, are also preferred.

[0075] Preferred products according to the invention may also contain flavoring substances (flavor modifiers) for masking bitter and / or spicy taste impressions. (Other) Flavor modifiers are selected from, for example, the following table: nucleotides (e.g., adenosine 5'-monophosphate, cytidine 5'-monophosphate) or pharmaceutically acceptable salts thereof, lactisole, sodium salts (e.g., sodium chloride, sodium lactate, sodium citrate, sodium acetate, sodium gluconate), other hydroxyflavonoids (e.g., eriodictyol, homoeriodictyol, and their sodium salts), particularly those described in US 2002 / 0188019, and hydroxybenzoic acid amides (e.g., according to DE 10 2004041 496) under DE 10 2004041 496. 2,4-Dihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2,4,6-trihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2-hydroxybenzoic acid-N-4-(hydroxy-3-methoxybenzyl)amide, 4-hydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2,4-dihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide monosodium salt, 2,4-dihydroxybenzoic acid-N-2- (4-hydroxy-3-methoxyphenyl)acetamide, 2,4-dihydroxybenzoic acid-N-(4-hydroxy-3-ethoxybenzyl)amide, 2,4-dihydroxybenzoic acid-N-(3,4-dihydroxybenzyl)amide and 2-hydroxy-5-methoxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]amide (Aduncamid), 4-hydroxybenzoic acid vanillylamine), and bitter-masking hydroxydeoxybenzoine, for example according to WO 2006 / 106023 (e.g., 2-(4-hydroxy-3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl) ethyl ketone, 1-(2,4-dihydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-ethyl ketone, 1-(2-hydroxy-4-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl) ethyl ketone), amino acids (e.g., γ-aminobutyric acid, which reduces or masks unpleasant taste sensations such as bitterness, as specified in WO 2005 / 096841), glyceryl malate, as specified in WO 2006 / 003107, salty mixtures, as specified in PCT / EP 2006 / 067120, diacetyl trimer, as specified in WO 2006 / 058893, and mixtures of whey protein with lecithin and / or bitter-masking substances such as gingerone, as specified in WO 2007 / 003527.

[0076] Preferred flavoring substances are those that produce a sweet taste impression, and other flavoring substances that produce a sweet taste impression preferably include:

[0077] Vanillin, ethyl vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxy-benzaldehyde), furanone (2,5-dimethyl-4-hydroxy-3(2H)-furanone) and their derivatives (e.g., cyclohomofuranone, 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuranone (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy- 3-(2H)-furanone), maltol and its derivatives (preferably ethyl maltol), coumarin and its derivatives, γ-lactones (e.g., γ-undecyl lactone, γ-nonyl lactone), δ-lactones (e.g., 4-methyl-δ-decyl lactone, masoyl lactone, δ-decyl lactone, tuberolactone), methyl sorbate, bisvanillin, 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone, 2- Hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, fruit esters and fruit lactones (e.g., n-butyl acetate, isoamyl acetate, ethyl propionate, ethyl butyrate, n-butyl butyrate, isoamyl butyrate, 3-methyl-ethyl butyrate, ethyl hexanoate, allyl hexanoate, n-butyl hexanoate, ethyl octanoate, ethyl 3-methyl-3-phenyldehydroglyceroate, 2-trans-4-cis-decadienyl ethyl ester) 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-aldehyde, 4-hydroxycinnamic acid, 4-methoxy-3-hydroxycinnamic acid, 3-methoxy-4-hydroxycinnamic acid, 2-hydroxycinnamic acid, 2,4-dihydroxybenzoic acid, 3-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, vanillic acid, homovanillic acid, vanillylmandelic acid, and phenylacetaldehyde.

[0078] Flavoring substances used to mask unpleasant taste impressions

[0079] Oral formulations may also contain flavoring substances to mask bitter and / or spicy taste impressions. These (other) flavor modifiers are selected from, for example, the following table: nucleotides (e.g., adenosine 5'-monophosphate, cytidine 5'-monophosphate) or pharmaceutically acceptable salts thereof, lactisole, sodium salts (e.g., sodium chloride, sodium lactate, sodium citrate, sodium acetate, sodium gluconate), hydroxyflavonoids, preferably eriodictyol, sterubin (eriodictyol-7-methyl ether), homoeriodictyol, and their sodium, potassium, calcium, magnesium, or zinc salts (especially those described in EP). Those disclosed in 1258200A2, wherein the relevant compounds are incorporated herein by reference, hydroxybenzoic acid amides, preferably 2,4-dihydroxybenzoic acid vanillamide, 2,4-dihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2,4,6-trihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2-hydroxybenzoic acid-N-4-(hydroxy-3-methoxybenzyl)amide, 4-hydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2,4- Dihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide monosodium salt, 2,4-dihydroxybenzoic acid-N-2-(4-hydroxy-3-methoxyphenyl)acetamide, 2,4-dihydroxybenzoic acid-N-(4-hydroxy-3-ethoxybenzyl)amide, 2,4-dihydroxybenzoic acid-N-(3,4-dihydroxybenzyl)amide and 2-hydroxy-5-methoxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]amide (Aduncamid), 4-hydroxybenzoic acid vanillylamine (especially such as WO As described in 2006 / 024587, the relevant compounds disclosed therein are incorporated herein by reference), Hydroxydeoxybenzoine, preferably 2-(4-hydroxy-3-methoxyphenyl)-1-(2,4,6-tris(hydroxyphenyl) ethyl ketone, 1-(2,4-dihydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-ethyl ketone and 1-(2-hydroxy-4-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl) ethyl ketone (especially as described in WO The compounds disclosed in WO2006 / 106023, which are incorporated herein by reference, are hydroxyphenyl alkyl diones, such as gingerdion-[2], gingerdion-[3], gingerdion-[4], dehydrogingergion-[2], dehydrogingergion-[3], dehydrogingergion-[4], (especially those substances described in WO2007 / 003527, which are incorporated herein by reference);Diacetyl trimers (especially those described in WO2006 / 058893, the relevant compounds disclosed herein are incorporated herein by reference), γ-aminobutyric acids (especially those described in WO2005 / 096841, the relevant compounds disclosed herein are incorporated herein by reference), bisvanillin (especially those described in WO2004 / 078302, the relevant compounds disclosed herein are incorporated herein by reference), and 4-hydroxydihydrochalcones (preferably as described in US2008 / 227867A1, the relevant compounds disclosed herein are incorporated herein by reference), particularly phloretin and davidigenin, mixtures of amino acids or whey protein with lecithin, hesperidin such as disclosed in WO2007 / 014879, these compounds are incorporated herein by reference, 4-hydroxydihydrochalcones, such as WO The compounds disclosed in 2007 / 107596 are incorporated herein by reference, as are the propenylphenyl glycosides (piperoyl glycosides) described in EP1955601A1, which are incorporated herein by reference; Rubussuavissimus extract; Hydroxya macrophylla extract as described in EP 2298084 A1; senna alkaloids and their derived flavor compositions as described in EP2008530A1; umami compounds as described in WO 2008 / 046895A1 and EP 1989944A1; umami compounds as described in EP2064959A1 and EP2135516A1; Vanilylllignanen; enterodiol; and N-decadienoic acid and mixtures thereof.

[0080] food coloring

[0081] Food coloring, or simply coloring, is a food additive used to color food. Colorings can be divided into natural and synthetic colorings. Like natural colorings, synthetic colorings are derived from synthetic sources. Natural colorings are synthetic imitations of naturally occurring colored substances. Suitable pigments used in the compositions of the present invention are selected from: curcumin, E100; riboflavin; lactoflavin; vitamin B2, E101; tartrazine, E102; quinoline ethyl, E104; orange-yellow S; orange-yellow RGL, E110; cochineal; carmine acid; carmine, E120; azorubin; carmoisin, E122; Amaranth, E123; cochineal (Cochenillerot A, Ponceau 4R); Victoriascharlach 4R, E124; erythrosin, E127; and allurarot. AC), E129, Patent Blue, E131, Indigo (Indigotin, Indigo-Karmin), E132, Brilliant Blue FCF (Brillantblau FCF), Patent Blue AE, Amidoblau AE, E133, Chlorophyll, Chlorophylline, E140, Chlorophyll Copper Complex, Chlorophylline Copper Complex, E141, Brilliant Green, Green S, E142, Caramel ( Zuckercouleur), E150a, caustic sulfite caramel E150b, Ammonia Caramel E150c, Ammonium Sulfite-Caramel; E150d, Brilliant Black FCF, Brilliant Black PN, Black PN; E151, Vegetable Carbon; E153, Brown FK; E154, Brown Serotonin (Braun HT); E155, Carotene (Carotin, Karotin); E160a, Annatto, Bixin, Norbixin; E160b, Capsanthin, Capsorubin; E160c, Lycopin; E160d, Apocarotinal, β-Apocarotinal; E160e, β-Apocarotinal Ethyl Acetate (C30), Ap ocarotinester, β-carotene, E160f, lutein, xanthophyll, E161b, canthaxanthin, E161g, betanin, betenrot, E162, anthocyane, E163, calcium carbonate, E170, titanium dioxide, E171, iron oxide, iron hydroxide, E172, aluminum, E173, silver, E174, gold, E175, litholrubin BK, Rubinpigment BK, E180.

[0082] chewing gum

[0083] Preferred oral formulations may include, in particular, chewing gum. These products typically contain both water-insoluble and water-soluble components.

[0084] Water-insoluble substrates, also known as "colloidal substrates," typically contain natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, dyes, and optionally waxes. The substrate typically constitutes 5 to 95% by weight of the total formulation, preferably 10 to 50% by weight, and particularly 20 to 35% by weight. In a typical embodiment of the invention, the substrate consists 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, and small amounts of additives such as dyes, antioxidants, etc., provided that these small amounts are water-soluble in all cases.

[0085] Suitable synthetic elastomers are, for example, polyisobutylene, isobutylene-isoprene copolymer (“butyl elastomer”), styrene-butadiene copolymer (styrene:butadiene ratio, for example, 1:3 to 3:1), polyvinyl acetate, polyisoprene, polyethylene, vinyl acetate-vinyl laurate copolymer and mixtures thereof with an average molecular weight (according to GPC) of 10,000 to 100,000, preferably 50,000 to 80,000, having an average molecular weight (according to GPC) of 2,000 to 90,000, and preferably 10,000 to 65,000, having an average molecular weight (according to GPC) of 10,000 to 65,000. Suitable examples of natural elastomers are rubbers, such as smoked latex or liquid latex or guar gum, and natural rubbers such as keratomileus, lechi caspi, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, roseindinha, gum sylvestre, gutta-percha, and mixtures thereof. The selection of synthetic and natural elastomers and their mixing ratios are primarily based on whether the chewing gum will produce bubbles (“bubblegum”). Preferably, an elastomer mixture containing keratomileus, lechi caspi, sorva, and sorva is used.

[0086] In most cases, elastomers are difficult to process or fully control, thus the use of specific plasticizers has proven advantageous, which must, of course, specifically meet all the requirements permitted for use as food additives. Esters of resin acids, such as low-fatty alcohols or polyols with fully or partially cured monomers or oligomeric resin acids, are primarily considered in this regard. Methyl, glycerol, or pentaerythritol esters and mixtures thereof are particularly used for this purpose. Alternatively, terpene resins derived from α-pinene, β-pinene, δ-limonene, or mixtures thereof may also be considered.

[0087] Magnesium carbonate or calcium carbonate, ground foam rock, silicates, especially magnesium silicate or aluminum silicate, clay, bauxite, talc, titanium dioxide, monocalcium phosphate, dicalcium or tricalcium phosphate, and cellulose polymers are used as fillers or thickeners.

[0088] Suitable emulsifiers are tallow, hardened tallow, hardened or partially hardened vegetable oil, cocoa butter, metaglycerides, lecithin, triacetin, and saturated or unsaturated fatty acids containing 6 to 22, preferably 12 to 18, carbon atoms, and mixtures thereof.

[0089] Examples of dyes and bleaching agents that could be considered for use include FD and C type plant and fruit extracts permitted for food coloring, as well as titanium dioxide.

[0090] The substrate composition may contain wax or not; examples of wax-free compositions can be found in patent document US 5,286,500, the contents of which are expressly incorporated herein by reference.

[0091] Besides the water-insoluble gum base, chewing gum formulations typically contain water-soluble components, such as softeners, sweeteners, fillers, flavoring substances, taste enhancers, emulsifiers, dyes, acidifiers, and antioxidants, provided that these components are sufficiently water-soluble. Depending on the water solubility of a specific representative substance, a single component can belong to either the water-insoluble or water-soluble phase. However, a combination of, for example, water-soluble and water-insoluble emulsifiers can be used, where the single representative substance is located in a different phase. Typically, the water-insoluble component constitutes 5 to 95% by weight of the formulation, and preferably about 20 to 80% by weight.

[0092] Water-soluble softeners or plasticizers are added to chewing gum compositions to improve chewability and chewing sensation, and are typically used in the mixture at a rate of 0.5 to 15% by weight. Typical examples are glycerin, lecithin, and aqueous solutions of sorbitol, hardened starch hydrolysate, or corn syrup.

[0093] Sugary or sugar-free compounds can be considered as sweeteners, used in amounts of 5 to 95% by weight, preferably 20 to 80% by weight, and particularly 30 to 60% by weight, based on the chewing gum composition. Typical sugar sweeteners are sucrose, glucose, maltose, dextrin, invert sugar powder, fructose, galactose, corn syrup, and mixtures thereof. Sorbitol, mannitol, xylitol, hardened starch hydrolysate, maltitol, and mixtures thereof can be considered as sugar substitutes. In addition, substances defined as high-intensity artificial sweeteners (HIAS) can be used alone or in mixtures as additives, such as, for example, sucralose, aspartame, acesulfame potassium salts, alitane, saccharin and saccharin salts, cyclohexanesulfonic acid and its salts, glycyrrhizin, dihydrochalcone, thomaline, monosodium glutamate, etc. Particularly effective are hydrophobic HIAS, the subject of patent application WO 2002 091849 A1 (Wrigleys), as well as stevia extract and its active ingredients, particularly redycidine A. The dosage of these substances depends primarily on performance and is typically 0.02 to 8% by weight.

[0094] In particular, suitable fillers for producing low-calorie chewing gum include, for example, polydextrose, raftilose, inulin, NutraFlora, palatinoseoligosaaccharides, guar gum hydrolysate, and dextrin.

[0095] The selection of additional flavoring substances is virtually limitless and not essential to the invention in nature. Typically, the total content of all flavoring substances is 0.1 to 15% by weight, preferably 0.2 to 5% by weight, based on the chewing gum composition. Other suitable flavoring substances are, for example, essential oils, synthetic flavorings, such as anise seed oil, star anise oil, cumin oil, eucalyptus oil, fennel oil, citrus oil, wintergreen oil, clove oil, etc., which can also be used in oral and dental care products.

[0096] In addition, chewing gum may contain other aids and additives suitable for dental care, especially for combating plaque and gingivitis, such as chlorhexidine, CPC, or triclosan. Furthermore, it may contain pH adjusters (such as buffers or urea), anti-caries active substances (such as phosphates or fluoride), and bioactive ingredients (antibodies, enzymes, caffeine, plant extracts), provided that these substances are permitted for use in food and do not react with each other in an undesirable manner.

[0097] Oral and dental care compositions

[0098] The oral sweetened products according to the present invention are particularly suitable for oral and dental care. Examples include toothpaste, tooth gel, tooth powder, mouthwash, etc. Toothpaste or tooth cream generally refers to a water-based gel or paste formulation, thickener, humectant, abrasive or cleaning agent, surfactant, sweetener, flavoring agent, deodorizing active ingredient, and active ingredient for combating oral and dental diseases. All conventional cleaning agents, such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicate, calcium pyrophosphate, finely dispersed synthetic resin, silica, alumina, and alumina trihydrate, can be used in the toothpaste according to the present invention.

[0099] Preferably, the cleansing agent suitable for the toothpaste of the present invention is finely dispersed dry gel silica, hydrogel silica, precipitated silica, alumina trihydrate, and finely dispersed α-alumina, or a mixture thereof, in an amount of 15 to 40% by weight of the toothpaste. As a humectant, low molecular weight polyethylene glycol, glycerin, sorbitol, or a mixture thereof are primarily considered in amounts up to 50% by weight. Among known thickeners, suitable thickeners are finely dispersed dry gel silica and hydrocolloids, such as, for example, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl guar gum, hydroxyethyl starch, polyvinylpyrrolidone, high molecular weight polyethylene glycol, plant gums such as astragalus gum, agar, carrageenan, gum arabic, xanthan gum, and carboxyvinyl polymers (e.g., (Class). In addition to mixtures of menthol and furan compounds, oral and dental care compositions may particularly contain surfactants, preferably anionic and nonionic high-foaming surfactants, such as those described above, but especially alkyl ether sulfates, alkyl polyglycosides and mixtures thereof.

[0100] Other common toothpaste additives are:

[0101] • Preservatives and antimicrobial substances, such as methylparaben, ethylparaben or propylparaben, sodium sorbate, sodium benzoate, bromochlorophenol, phenyl salicylate, thymol, etc.

[0102] • Antiscaling active ingredients, such as organophosphates like 1-hydroxyethane-1,1-diphosphonic acid, 1-phosphonopropane-1,2,3-tricarboxylic acid, and those known, for example, US 3,488,419, DE 2224430 A1 and DE 2343196 A1;

[0103] Other anti-caries substances include, for example, sodium fluoride, sodium monofluorophosphate, and tin fluoride;

[0104] Sweeteners, such as sodium saccharin, sodium cyclohexanesulfonate, sucrose, lactose, maltose, fructose, or... (L-aspartic-L-phenylalanine methyl ester), stevia extract or its sweet components, especially rebaudioside;

[0105] Other flavorings, such as eucalyptus oil, anise seed oil, fennel oil, cumin oil, methyl acetate, cinnamaldehyde, anethole, vanillin, thymol, and mixtures of these substances with other natural and synthetic flavorings;

[0106] Pigments such as titanium dioxide;

[0107] ·dye;

[0108] • Buffering substances such as primary, secondary or tertiary alkali metal phosphates, citric acid / sodium citrate;

[0109] • Healing and anti-inflammatory substances, such as allantoin, urea, azurite, chamomile active ingredients, and acetylsalicylic acid derivatives.

[0110] A preferred embodiment of the oral formulation is a toothpaste in the form of an aqueous, paste dispersion, containing polishing agents, humectants, viscosity modifiers and optionally other conventional ingredients, as well as a mixture of menthol and menthol compounds in an amount of 0.5 to 2% by weight.

[0111] In mouthwashes, aqueous solutions of essential oils, emulsifiers, and astringents at various concentration gradients may be combined with toner extracts, plaque inhibitors, antibacterial additives, and flavor correctors. Other preferred embodiments of the invention are aqueous or aqueous solutions of mouthwash containing a mixture of menthol and furanyl menthol compounds at a concentration of 0.5 to 2% by weight. Mouthwashes diluted before use can achieve sufficient effect by using a higher concentration relative to the intended dilution ratio.

[0112] In addition, to improve flow properties, co-solvents such as ethanol, isopropanol, or polyols can be used; these substances mainly correspond to the aforementioned carriers. Considerable polyols preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Polyols may contain other functional groups, particularly amino groups or be modified with nitrogen. A typical example is...

[0113] ·glycerin;

[0114] Alkanediols, such as ethylene glycol, diethylene glycol, propylene glycol, butanediol, hexanediol, and polyethylene glycol with an average molecular weight of 100 to 1000 Daltons;

[0115] • Technical oligoglyceride blends with a degree of self-condensation of 1.5 to 10, such as technical diglyceride blends with a diglyceride content of 40 to 50% by weight;

[0116] • Hydroxymethyl compounds, such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol, and dipentaerythritol;

[0117] • Low alkyl glycosides, especially those with 1 to 8 carbon atoms in the alkyl group, such as methyl and butyl glycosides;

[0118] • Sugar alcohols containing 5 to 12 carbon atoms, such as sorbitol or mannitol;

[0119] • Sugars containing 5 to 12 carbon atoms, such as glucose or sucrose;

[0120] Amino sugars, such as glucosamine;

[0121] Diolamines, such as diethanolamine or 2-amino-1,3-propanediol.

[0122] Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, benzoates, pentylene glycol or sorbic acid, and their names are as follows: Silver complexes, and other substances listed in Annex 6, Parts A and B of the Cosmetic Regulations.

[0123] The aromatic oils that can be mentioned are mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers (lily, lavender, rose, jasmine, orange blossom, ylang-ylang), stems and leaves (geranium, patchouli, bitter orange), fruits (fennel, coriander, cilantro, juniper), peels (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, costus root, iris, calamus), woods (pine, sandalwood, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), pine needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galangal, elemi, benzoin, myrrh, frankincense, red myrrh). Animal ingredients, such as civet and castoreum, can also be considered. Typical synthetic fragrance compounds are esters, ethers, aldehydes, ketones, alcohols, and hydrocarbon products. Ester aromatic compounds include, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinylacetate, ethyl phenacetate, linalyl benzoate, benzyl formate, ethyl phenylglycine, allyl cyclohexylpropionate, styraxyl propionate, and benzyl salicylate. Ethers include, for example, benzyl ethyl ether; aldehydes include, for example, straight-chain alkanes containing 8 to 18 carbon atoms, citral, citronellol, citronelloloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellol, lily of the valley aldehyde, and bournezaldehyde; ketones include, for example, ionone, α-isomethylionone, and methyl cedrol; alcohols include, for example, anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenethyl alcohol, and terpineol; hydrocarbons mainly include terpenes and balsams. However, it is preferable to use a mixture of various aromatic compounds that together produce the desired fragrance. Other suitable aromatic oils are essential oils with low volatility that are commonly used as aromatic components, such as sage oil, chamomile oil, clove oil, bee pollen oil, peppermint oil, cinnamon leaf oil, lime flower oil, juniper berry oil, vetiver oil, frankincense oil, galbanum oil, rockrose oil, and lavender oil. The following substances are preferred for use alone or in combination: bergamot oil, dihydromyrcenol, lily aldehyde, neolily aldehyde, citronellol, phenethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzylacetone, cyclamen aldehyde, linalool, ethoxymethoxycycloundecane, ambroxan, indole, hedione, sandelice, citrus essential oils, citrus oil, orange oil, allyl pentyl glycolate, cyclovertal, bright lavender oil, sage oil, damascone, bourbon geranium oil, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geraniol acetate, benzyl acetate, rose ether, romilllate, ethyl 2-ethylhexanoate (irotyl), and 2-tert-butylcyclohexyl ethyl carbonate (floramat).

[0124] For example, peppermint oil, spearmint oil, anise seed oil, star anise oil, cumin oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, and menthol can be used as spices.

[0125] Methods and uses

[0126] Another subject of the invention relates to a method for enhancing the pungent flavor of a compound of formula (I) or an essential oil containing one or more compounds of formula (I) and reducing its burning sensation, characterized in that at least one menthol compound is added to the formulation containing these substances, preferably in an amount of about 0.5 to about 5% by weight.

[0127] The final subject of this invention relates to the use of menthol compounds to correct the flavor of formula (I) compounds or essential oils containing one or more formula (I) compounds.

[0128] The methods and uses described above also apply to the dosages and preferred embodiments detailed above, so there is no need to repeat them.

[0129] Example

[0130] Application Trial

[0131] Examples 1 to 4, and comparative examples C1 to C2

[0132] The flavor characteristics of various flavoring mixtures were evaluated by a test group consisting of 5 trained test subjects. For this purpose, 0.5% by weight of the mixture was added to a standard chewable sweetener preparation without added sweeteners or flavorings. The results are shown in Table 1. Evaluations were based on scores from (5) = compliant to (0) = non-compliant. Average values ​​are given. Examples 1 to 4 are according to the invention, and Examples V1 to V2 are used for comparison.

[0133] Table 1

[0134] Sensory evaluation of spice blends

[0135]

[0136] The examples and comparative examples demonstrate that the mixtures according to the invention are significantly better in terms of sensory properties than the single substances.

[0137] Many formulation examples are given below.

[0138] Formulation Examples

[0139] Example 1

[0140] Toothpaste (amount used in weight %)

[0141] Element Dosage Deionized water Add to 100 Sorbitol 70% 45.00 Trisodium phosphate 0.10 saccharin 0.20 Sodium monofluorophosphate 1.14 PEG 1500 5.00 Sident 9 (Silica Abrasive) 10.00 Sident 22S (Thickened Silica) 8.00 Sodium carboxymethyl cellulose 1.10 Oxidized peptide (IV) 0.50 Deionized water 4.50 Sodium lauryl sulfate (SLS) 1.50 spice mixture 1.00 Solbrol M (sodium salt) (methylparaben) 0.15 Spice Mixture 3 0.40

[0142] Example 2

[0143] Toothpaste containing zinc citrate (amount by weight%)

[0144]

[0145]

[0146] Example 3

[0147] Mouthwash (dosage by weight%)

[0148]

[0149] Example 4

[0150] Guttate teething gel (in weight percent)

[0151]

[0152]

[0153] Example 5

[0154] Anti-plaque toothpaste (dosage by weight%)

[0155] Element Dosage Carrageenan 0.90 glycerin 15.00 Sorbitol 70% in water 25.00 PEG 1000 3.00 Sodium fluoride 0.24 Tetrapotassium diphosphate 4.50 Tetrasodium diphosphate 1.50 Sodium saccharin 0.40 Precipitated silica 20.00 Titanium dioxide 1.00 Triclosan 0.30 Peppermint flavoring (containing 60% by weight L-carvone and 25% by weight L-menthol) 1.00 Sodium dodecyl sulfate 1.30 distilled water Add to 100 benzyl alcohol 0.50 Spice Mixture 3 0.25

[0156] Example 6

[0157] Toothpaste for sensitive teeth (dosage by weight%)

[0158] Element Dosage Sodium carboxymethyl cellulose 0.70 Xanthan Gum 0.50 glycerin 15.00 Sorbitol 70% in water 12.00 potassium nitrate 5.00 Sodium monofluorophosphate 0.80 Sodium saccharin 0.20 spice mixture 1.00 Calcium carbonate 35.00 silicon dioxide 1.00 Sodium dodecyl sulfate (SDS) 1.50 distilled water Ad 100 PHB methyl ester and PHB propyl ester 0.20 Spice Mixture 4 0.50

[0159] Example 7

[0160] Toothpaste and mouthwash in a 2:1 ratio (dosage by weight%)

[0161]

[0162]

[0163] Example 8: Fluoride mouthwash (dosage by weight%)

[0164]

[0165] Example 9: Sugar-free chewing gum (amount by weight%)

[0166]

[0167]

Claims

1. Fragrance preparations, which contain (a) Compound of formula (I) Where R1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 4 carbon atoms, R2 represents hydrogen or hydroxyl, and R3 represents hydrogen, methyl, or methoxy. Or, essential oils containing one or more compounds of formula (I), and (b) at least one menthol compound; Its features are, Component (b) is a mixture of menthol and menthyl acetate. The weight ratio of component (a) to component (b) is from 80:20 to 99:1, and The weight ratio of menthol to menthyl acetate in component (b) is 60:40 to 40:

60.

2. The formulation according to claim 1, characterized in that, The compounds of formula (I) are selected from eugenol, anethole, thymol and carvacrol and mixtures thereof.

3. The formulation according to claim 1 or 2, characterized in that, It contains (a) 80 to 99% by weight of at least one compound of formula (I) or an essential oil containing one or more compounds of formula (I), (b1) 1 to 20% by weight of menthol, and (b2) 1 to 20% by weight of menthyl acetate, The premise is that the dosage given in each case is increased to 100 by weight.

4. An oral formulation comprising the mixture according to claim 1.

5. The formulation according to claim 4, characterized in that, It includes food, pharmaceutical preparations and / or oral and dental care preparations.

6. The formulation according to claim 5, characterized in that, It is a hard caramel, a chewing candy, or gum.

7. The formulation according to claim 5, characterized in that, It is a cold syrup, cold spray, or cold candy.

8. The formulation according to claim 5, characterized in that, It can be toothpaste, mouthwash, or medicated chewing gum.

9. The formulation according to any one of claims 4 to 8, characterized in that, Based on the final formulation, it contains 0.5 to 5% by weight of the formulation according to claim 1.

10. A method for enhancing the pungent flavor of essential oils containing compounds of formula (I) and reducing their burning sensation. Where R1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 4 carbon atoms, R2 represents hydrogen or hydroxyl, and R3 represents hydrogen, methyl, or methoxy. Its features are, Add at least one menthol compound to a formulation containing these substances, wherein the weight ratio of the compound of formula (I) to the at least one menthol compound is 85:15 to 95:5, and The at least one menthol compound is a mixture of menthol and menthyl acetate, wherein the weight ratio of menthol to menthyl acetate is 60:40 to 40:

60.

11. A method for enhancing the pungent flavor of essential oils containing compounds of formula (I) and reducing their burning sensation. Where R1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 4 carbon atoms, R2 represents hydrogen or hydroxyl, and R3 represents hydrogen, methyl, or methoxy. Its features are, A mixture of menthol and menthyl acetate is added to a formulation containing these substances and a compound of formula (I), wherein the weight ratio of the compound of formula (I) or the essential oil containing the compound of formula (I) to the mixture is 80:20 to 99:1, and the weight ratio of menthol to menthyl acetate is 60:40 to 40:

60.

12. The use of a mixture of menthol and menthyl acetate for correcting the flavor of essential oils containing compounds of formula (I), Where R1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 4 carbon atoms, R2 represents hydrogen or hydroxyl, and R3 represents hydrogen, methyl, or methoxy. Its features are, The weight ratio of the compound of formula (I) to the mixture is 80:20 to 95:5, and the weight ratio of menthol to menthyl acetate is 60:40 to 40:60.

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