Composition substituting mint oil-based products

Abstract

The present invention relates to a composition having a mint aroma that is usable as a substitute of mint oil of natural origin or dementholized mint oil (DMO) derived therefrom and in which contents of undesired components are widely omitted. The invention further refers to a method for preparing such composition. Moreover, the invention relates to a formulation and a product comprising such composition and uses thereof.

Description

[0001] Composition substituting mint oil-based products

[0002] The present invention relates to a composition having a mint aroma that is usable as a substitute of mint oil of natural origin or dementholized mint oil (DMO) derived therefrom and in which contents of undesired components are widely omitted. The invention further refers to a method for preparing such composition. Moreover, the invention relates to a formulation and a product comprising such composition and uses thereof.

[0003] Mint aromas have a multitude of uses, such as use as a fragrance in cosmetics, in personal care and in industrial products, or as a flavoring ingredient in food and beverages. Mint aroma is often desired to provide a fresh aroma sensation. Such mint aroma may comprise odor perceptions (also: scent) and / or flavor (also: taste) perceptions beside a cooling sensation. In addition to the use of mint aroma in mouth care products such as toothpastes and mouthwashes mint aroma is rather common in consumable products such as chewing gum, candy, and other food products as well as in beverages and drinks. Furthermore, a minty odor which may also bear cooling sensation is often desired in cosmetic products usable on the skin of body and face and on hair. Household products such as cleaners, dishwashing agents and laundry agents may bear a mint aroma. Some insect repellents also bear minty odor.

[0004] A mint aroma may be achieved by using an essential oil (EO) of mint plants (mint oil) or a fraction or component thereof. Traditionally, mint oils are prepared as excepts from mint plants such as from Mentha arvensis (also: corn mint, field mint, or wild mint) or Mentha x piperita (peppermint). In particular, Mentha arvensis is industrially used as source of mint oil. Often, mint oil is obtained by steam distillation of the respective mint plant material, in particular aerial plant material such as stems and leaves of mint plants.

[0005] In many products, menthol, in particular (-)-menthol (also: L-menthol), which is one of the main components of mint oils, can be very well used instead of mint oil. Menthol can be of natural or synthetic origin. For instance, it can be obtained from natural mint oils such as mint oil of Mentha arvensis (also: corn mint, field mint, or wild mint). For the purpose of isolating menthol from mint oil, such mint oil may be stored at a temperature below the solidification point of menthol in this oil until crystals of menthol have been formed in desired amounts. The vast majority of other aroma products in mint oil remain in liquid form. The crystals of menthol can be separated from the remaining liquid by any means such as by discarding the supernatant of the liquid, filtration, and / or centrifugation. This provides crystals of widely isolated menthol on the one hand and a remaining liquid considered as dementholized mint oil (DMO) on the other hand. As the global demand of menthol cannot be reasonable met by menthol obtained from mint oil, the majority of menthol is currently obtained from synthetic routes, which allow to obtain highly pure and reliable menthol.

[0006] While in some products, the plain fresh and mint aroma sensation of menthol is desired and sufficient, in other products a complex aroma of full mint oil is desired. The latter products require that, in addition to menthol, further aroma components of mint oil are present in the composition. Typically, either mint oil of natural origin or DMOderived therefrom is used for this purpose. Mint oil or DM0 derived therefrom may be used either alone or in combination with additionally admixed menthol. Using mint oil of natural origin or DM0 derived therefrom bears notable technical drawbacks.

[0007] Mint oil of natural origin as well as DM0 derived therefrom typically contains undesired components. Mint oil of Mentha arvensis as well as DM0 derived therefrom inherently typically contains significant contents of less desired components such as menthofuran and pulegone (Wang et al., "Comprehensive quality assessment of peppermint oils and commercial products: An integrated approach involving conventional and chiral GC / MS coupled with chemometrics "Journal of Chromatography B, 1232, 2024:123953). In particular, mint oil of Mentha x piperita is generally characterized by the presence of significant contents of oxygenated monoterpenes including menthofuran and pulegone (Wang et al., Journal of Chromatography B, 1232, 2024:123953). Though often accepted in natural products inherently containing significant contents of such ingredients, menthofuran and pulegone are rather less desired components due to their toxicity at higher concentrations (Khojasteh et al., "Metabolism and Toxicity of Menthofuran in Rat Liver Slices and in Rats”, Chem. Res. Toxicol. 2010, 23:1824-1832; European Medicines Agency (EMEA), "Public statement on the use of herbal medicinal products containing pulegone and menthofuran”, 2016, EMA / HMPC / 138386 / 2005 Rev. 1, Committee on Herbal Medicinal Products (HMPC)). Especially, in medical / pharmaceutical contexts such as in patients having potential issues in liver metabolism and pregnant and breastfeeding women, the contents of menthofuran and pulegone are desired to be rather low (European Medicines Agency (EMEA), "Public statement on the use of herbal medicinal products containing pulegone and menthofuran”, 2016, EMA / HMPC / 138386 / 2005 Rev. 1, Committee on Herbal Medicinal Products (HMPC)). Though certain amounts are often tolerated in essential oils of natural origin, it is desirable to have alternatives widely avoiding such components. Even in semi-synthetic mint oil compositions such as those described in WC2021222485 menthofuran and optionally pulegone are often present, originating from the natural oil.

[0008] Significant efforts have been taken to at least partly decrease the content of menthofuran such as by hydrogenation thereof (US3083105A), by generating a menthofuran-maleic anhydride adduct thereof (EP0113988B1) or by complex distillation processes (W 000 / 27217). Likewise, efforts have been taken to reduce the pulegone and menthofuran content in naturally derived peppermint oil such as by adding reducing agents such as sodium sulfite (US4861616A, US5047251A) or to decrease the content of menthofuran and pulegone in mint oil by adding a Lewis acid (US5204128A). This is however laborious and significant contents of menthofuran and pulegone often remain in the mint oil or DMO derived therefrom. It has also been considered to reduce the content of pulegone in DMO by hydrogenation involving a complex zeolite-based catalyst (IN434332B). All these methods are comparably laborious and complicated and require the use of the limited source of natural mint oil or DMO derived therefrom. The reduction of menthofuran or pulegone by hydrogen can further cause undesired side reactions of undesirably reduction of other products.Furthermore, generating mint oil as an essential oil (EO) from mint plants such as by steam distillation typically increases the content of a large variety of evaporable organic compounds with a rather low specificity. In case persistent xenobiotics such as agrochemicals such as insecticides, herbicides and / or other pesticides have been used when culturing the mint plants, or in case fungi such as molds or weeds producing evaporable hydrophobic metabolic products such as xenobiotics and toxins can likely contaminate the mint oil. Notably, such undesired evaporable hydrophobic compounds are often significantly accumulated in the obtained mint oil in comparison to the crude plant material.

[0009] Furthermore, the reliability of natural products such as mint oil is limited. The use of mint oil or DMO derived therefrom in several contexts may be hampered by significantly differing content range of its ingredients. In addition to differences between plant varieties and origins, the content ranges can even significantly differ between different harvesting times in the same region and comparable varieties (Soltanbeigi et al., "Planting-date and cutting-time affect the growth and essential oil composition of Mentha x piperita and Mentha arvensis", 2021, Industrial Crops & Products 170:113790). Content ranges of such naturally derived mint oils and fractions thereof are hardly adjustable to specific uses.

[0010] The content of essential oils in mint plant material is rather low. Thus, large amounts of plant material are required to obtain a minor volume of mint oil or DMO. Natural sources of mint oil or DMO are generally limited. The high global demand for mint aroma can hardly be covered by agricultural means. Agricultural land used for cultivating mint can compete with land usable for other purposes such as for food or energy production.

[0011] In view of the aforementioned, the use of naturally derived mint oil and products derived therefrom has a number of disadvantages. Accordingly, there is still an unmet need for a substitute of mint oil of plant origin and / or of dementholized mint oil (DMO) derived therefrom. A higher reliability as well as more flexibility and adjustability of content ranges to specific uses is particularly desired. Concomitantly, the composition should bear an essentially full mint aroma sensation, while the content ranges of undesired components is minimized or even essentially avoided.

[0012] Surprisingly, it has been found that a composition having a mint aroma can be obtained when comprising one or more stereoisomers of menthol, of menthone, of menthyl acetate, of isopulegol, and of linalool, and optionally germacrene, while less desirable components such as menthofuran and pulegone can be minimized or even omitted. It was surprisingly found that such composition having an essentially full spectrum of mint aroma can be even obtained from synthetic or isolated products without the need of mint oil. The obtained compositions bear virtually the same aroma sensation as DMO or mint oil obtained from mint oil of plant origin.

[0013] A first aspect of the present invention relates to a composition having a mint aroma, comprising (or consisting of): (A) one or more stereoisomers of menthol;

[0014] (B) one or more stereoisomers of menthone;(C) one or more stereoisomers of menthyl acetate;

[0015] (D) one or more stereoisomers of isopulegol; and

[0016] (E) one or both stereoisomers of linalool; and

[0017] (F) optionally one or both stereoisomers of germacrene and / or beta-caryophyllene,

[0018] wherein the composition does not comprise more than 100 ppm, related to the total mass of the composition as a whole, of menthofuran,

[0019] and wherein the composition does not comprise more than 0.25 wt.%, related to the total mass of the composition as a whole, of pulegone.

[0020] It was surprisingly found that a composition of the present invention provided a virtually nature-like full mint aroma sensation although the ingredients menthofuran and pulegone are virtually omitted. The content ranges can be highly reliably adjusted to the desired use. The content of plant-derived and synthetic material can be freely chosen. It was surprisingly found that menthofuran and pulegone do not necessarily have to be present to provide a full mint aroma spectrum. Furthermore, it was surprisingly found that menthofuran and pulegone can be replaced by components such as stereoisomers of menthol, in particular by neomenthol. It was further surprisingly found that a notable content of menthone, in particular when comprising (+)- and (-)-menthone, may add a desirable fresh note to the composition that may improve the impression of fresh mint oil.

[0021] In a preferred embodiment, the composition is a cosmetically and / or pharmaceutically acceptable composition and / or an otherwise consumable composition. Thus, it preferably has a reasonably low toxicity to be applied to humans and / or animals without substantial health risk when applied in reasonable amounts and optionally benefit for health.

[0022] As used herein, the term "aroma” may be understood in the broadest sense as bearing a gustatory and / or olfactory perception. An aroma may also be designated as flavor, scent, smell and / or odor. Aroma is typically perceived in the gustatory / olfactory system, either nasally and / or retro-nasally. As used herein, the aroma preferably focuses on perceptions different from the five basic taste perceptions, i.e., sweetness, sourness, saltiness, bitterness, and savoriness (also: umami).

[0023] As used herein, the term "mint aroma” may be understood in the broadest sense as having an aroma perception of mint, in particular Mentha arvensis and / or Mentha x piperita. The mint aroma is preferably the taste perception of full essential oil of such mint (mint oil), i.e., the extract of steam distillation product of a mint, in particular Mentha arvensis and / or Mentha x piperita, and / or dementholized mint oil (DMO) derived therefrom. In other words, a mint aroma is typically the olfactory perception of nature-like mint oil or DMO derived therefrom. Such aroma may be different from isolated (-)-menthol or stereoisomers thereof. In addition to the fresh and cooling aroma of (-)-menthol, mint aroma may also bear woody and optionally green and / or floral aroma perceptions. Mint aroma can be recognized by a person familiar therewith without undue burden, in particular by a professional flavorist and / or by a perfumer.As used herein, the content ranges of all components also include the compounds as such as well as the respective ions derived from the compounds in salts as far as formed, while the counterions preferably do not forming part of the mass content. As far as not otherwise defined, percentage ranges may be understood as percentage by weight (wt.%), which may also be designated as mass percentage or percentage per mass. As far as not otherwise defined, the percentage by weight refers to the total content of the respective composition or subcomponent.

[0024] As used herein, the term "stereoisomer” may be understood in the broadest sense as understood in the art. Typically, two or more stereoisomeric forms have the same constitutional formula when depicted two-dimensionally (i.e. in 2D) and not depicted in Fischer projection. In other words, stereoisomerism (also: spatial isomerism), may be understood as isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional (3D) orientations of two or more atoms of the molecular formula in space. Stereoisomers may comprise enantiomers and / or diastereomers and / or conformational isomers, preferably enantiomers and / or diastereomers. A stereoisomer may comprise one, two, three or more than three stereoisomeric centers. As used herein, the designation as (-)- and (+)-stereoisomers (which may also be designated as L- and D-stereoisomers, respectively) are used as commonly used in the art. It will be understood that stereoisomeric centers may also be designated as (R) or (S) according to the commonly known Cahn-lngold-Prelog (CIP) priority rules.

[0025] As used herein, the term "menthofuran” comprises both stereoisomers of menthofuran, i.e., (+)-menthofuran and (-)-menthofuran. In other words, the content ranges of menthofuran include the total content of the sum of (+)-menthofuran and (-)-menthofuran. Menthofuran may also be designated as 3,6-dimethyl-4,5,6,7-tetrahydro-1 -benzofuran or as tetrahydro-dimethylbenzofuran. Menthofuran may also include the compounds subsumable under the CAS No. 494-90-6). In a preferred embodiment, the composition does not comprise more than 10 ppm, preferably does not comprise more than 1 ppm, in particular does not comprise more than 0.1 ppm, related to the total mass of the composition as a whole, of menthofuran.

[0026] As used herein, the term "pulegone” comprises both stereoisomers of pulegone, i.e., (+)-pulegone and (-)-pulegone. In other words, the content ranges of pulegone include the total content of the sum of (+)-pulegone and (-)-pulegone. Pulegone may also be designated as 5-methyl-2-(propan-2-ylidene)cyclohexan-1-one, p-menth-4(8)-en-3-one, 5-4(8)-p-Menthen-3-one, 2-isopropylidene-5-methylcyclohexanone, or p-menth-4(8)-en-3-one. Pulegone may, for instance also include the compounds subsumable under the CAS Nos. 89-82-7 and / or 3391 -90-0. In a preferred embodiment, the composition does not comprise more than 0.2 wt.%, preferably does not comprise more than 0.1 wt.%, more preferably does not comprise more than 500 ppm, in particular does not comprise more than 100 ppm, of pulegone.In a preferred embodiment, the composition does not comprise more than 0.25 wt.%, preferably does not comprise more than 0.2 wt.%, more preferably does not comprise more than 0.1 wt.%, even more preferably does not comprise more than 500 ppm, in particular does not comprise more than 100 ppm, of menthofurolactone (also: 3,6-dimethyl-4,5,6,7-tetrahydrobenzofuran-2(3H)-one, 2(3H)-benzofuranone, 4,5,6,7-tetrahydro-3,6-dimethyl-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran-2(3H)-one).

[0027] In a preferred embodiment, the composition does not comprise more than 0.25 wt.%, preferably does not comprise more than 0.2 wt.%, more preferably does not comprise more than 0.1 wt.%, even more preferably does not comprise more than 500 ppm, in particular does not comprise more than 100 ppm of dehydromenthofurolactone.

[0028] Menthol is understood as generally understood. It can be also designated as 5-methyl-2-(propan-2-yl)-cyclohexan-1-ol or as 2-isopropyl-5-methylcyclohexanol. As used herein, the term "stereoisomers of menthol” may be understood in the broadest sense as any stereoisomer of menthol. Such any stereoisomer of menthol may include (-)-menthol (also: L-menthol, levomenthol, levomentholum; CAS No: 2216-51-5), (+)-menthol (also: D-menthol; CAS No. 15356-60-2), (+)-isomenthol, (also : D-isomenthol; CAS No. 23283-97-8), (-)-isomenthol (also: L-isomenthol; CAS No. 20752-33-4), (+)-neomenthol (also: D-neomenthol; CAS No. 2216-52-6), (-)-neomenthol (also: L-neomenthol; CAS No. 20747-49-3), (+)-neoisomenthol (also: D-neoisomenthol; CAS No. 20752-34-5), (-)-neoisomenthol (also: L-neoisomenthol; CAS No. 64282-88-8), or a combination of two or more thereof. The diastereomeric stereoisomers of menthol may include menthol, isomenthol, neomenthol, and neoisomenthol. There are two possible enantiomers of each of these diastereomeric stereoisomers.

[0029] The composition of the present invention may comprise any contents of the one or more stereoisomers of menthol. In a preferred embodiment, the composition comprises 10 to 80 wt.%, preferably 25 to 70 wt.%, in particular 30 to 60 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol.

[0030] The one or more stereoisomers of menthol may be composed by any stereoisomer composition of menthol. In a preferred embodiment, the one or more stereoisomers of menthol comprise at least 60 wt.%, preferably at least 70 wt.%, in particular at least 80 wt.%, related to the total content of stereoisomers of menthol, of (-)-menthol, (+)-menthol, (-)-neomenthol, and (+)-neomenthol. In a preferred embodiment, the one or more stereoisomers of menthol comprise at least 15 wt.%, preferably at least 30 wt.%, in particular at least 45 wt.%, related to the total content of stereoisomers of menthol, of (-)-menthol and (+)-menthol. In a preferred embodiment, the one or more stereoisomers of menthol comprise at least 10 wt.%, preferably at least 20 wt.%, in particular at least 30 wt.%, related to the total content of stereoisomers of menthol, of (-)-menthol.In a preferred embodiment, the composition of the present invention comprises at least 20 wt.%, preferably at least 30 wt.%, more preferably at least 40 wt.%, in particular at least 50 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol.

[0031] The one or more stereoisomers of menthol may comprise any stereoisomers of menthol. In a preferred embodiment, the one or more stereoisomers of menthol comprise (-)-menthol and / or (+)-menthol. In a preferred embodiment, the one or more stereoisomers of menthol comprise (-)-menthol. In a preferred embodiment, the one or more stereoisomers of menthol comprise:

[0032] (A1) (-)-menthol, and

[0033] (B2) (+)-menthol.

[0034] Such mixture of may also be designated as "rac-menthol” or racemic menthol, independent of its content ratio. In a preferred embodiment, the one or more stereoisomers of menthol comprise (-)-menthol and (+)-menthol in a mass ratio of (-)-menthol : (+)-menthol of from 1:9 to 9:1. In a preferred embodiment, the one or more stereoisomers of menthol comprise (-)-menthol and (+)-menthol in a mass ratio of (-)-menthol : (+)-menthol of from 1:8 to 8:1, of from 1:7 to 7:1, of from 1:6 to 6:1, of from 1:5 to 5:1, of from 1:4 to 4:1, of from 1:3 to 3:1, of from 1:2 to 2:1, 1:1 to 8:1, of from 1:1 to 7:1, of from 1:1 to 6:1, of from 1:1 to 5:1, of from 1:1 to 4:1, of from 1:1 to 3:1, of from 1:1 to 2:1, of from 1:1 to 1.5:1, of from 1.0: 1.5 to 1.5: 1.0, or of approximately 1:1.

[0035] In a preferred embodiment, the one or more stereoisomers of menthol comprise:

[0036] (A1) 10 to 75 wt.%, preferably 25 to 70 wt.%, related to the total mass of stereoisomers of menthol, of (-)- menthol;

[0037] (A2) 5 to 50 wt.%, preferably 10 to 40 wt.%, related to the total mass of stereoisomers of menthol, of (+)- menthol; and

[0038] (A3) 1 to 70 wt.%, preferably, 5 to 40 wt.%, related to the total mass of stereoisomers of menthol, of neomenthol.

[0039] In a preferred embodiment, the total mass of (-)-menthol, (+)-menthol and neomenthol sums up to at least 75 wt.%, preferably of at least 90 wt.%, in particular at least 95 wt.%, of the total mass of stereoisomers of menthol.

[0040] As used herein, the term "stereoisomers of menthone” may be understood in the broadest sense as any stereoisomer of menthone. Such any stereoisomer of menthol may include (-)-menthone (also: L-menthone), (+)-menthone (D-menthone), (+)-isomenthone, (-)-isomenthone, or a combination of two or more thereof. In a preferred embodiment, the composition comprises at least 10 wt.%, related to the total mass of the composition as a whole, of stereoisomers of menthone. In a preferred embodiment, the composition of the present invention comprises at least 15 wt.%, preferably at least 20 wt.%, more preferably at least 25 wt.%, in particular at least 30 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone.The composition of the present invention may comprise any contents of the one or more stereoisomers of menthone. In a preferred embodiment, the composition comprises 20 to 70 wt.%, preferably 15 to 50 wt.%, in particular 20 to 40 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone.

[0041] The one or more stereoisomers of menthone may comprise any stereoisomers of menthone. In a preferred embodiment, the one or more stereoisomers of menthone comprise (-)-menthone and / or (+)-menthone. In a preferred embodiment, the one or more stereoisomers of menthone comprise (-)-menthone. In a preferred embodiment, the one or more stereoisomers of menthone comprise:

[0042] (B1) (-)-menthone, and

[0043] (B2) (+)-menthone.

[0044] Such mixture of may also be designated as "rac-menthone” or racemic menthone, independent of its content ratio. In a preferred embodiment, the one or more stereoisomers of menthone comprise (-)-menthone and (+)-menthone in a mass ratio of (-)-menthone : (+)-menthone of from 1:9 to 9:1. In a preferred embodiment, the one or more stereoisomers of menthone comprise (-)-menthone and (+)-menthone in a mass ratio of

[0045] (-)-menthone : (+)-menthone of from 1:8 to 8:1, of from 1:7 to 7:1, of from 1:6 to 6:1, of from 1:5 to 5:1, of from 1:4 to 4:1, of from 1:3 to 3:1, of from 1:2 to 2:1, 1:1 to 8:1, of from 1:1 to 7:1, of from 1:1 to 6:1, of from 1:1 to 5:1, of from 1:1 to 4:1, of from 1:1 to 3:1, of from 1:1 to 2:1, of from 1:1 to 1.5:1, of from 1.0:1.5 to 1.5:1.0, or of approximately 1:1.

[0046] Neomenthol may bear a fresh mint aroma note. Neomenthol may or may not be comprised in the composition of the present invention. In a preferred embodiment, the composition comprises at least 0.1 wt.%, at least 1 wt.%, 3 more preferably at least 2 wt.%, related to the total mass of the composition as a whole, of neomenthol. In a preferred embodiment, the composition comprises at least 2 wt.%, preferably between 3 and 40 wt.%, preferably between 4 and 30 wt.%, in particular between 10 and 25 wt.%, related to the total mass of the composition as a whole, of neomenthol.

[0047] In a preferred embodiment, the one or more stereoisomers of menthone comprise:

[0048] (B1) (-)-menthone,

[0049] (B2) (+)-menthone, and

[0050] (B3) (-)-isomenthone and / or (+) isomenthone.

[0051] The aforementioned components may be comprised in the composition in any content ratio. In a preferred embodiment, the mass ratio of (B1+B2) : (B3) is in the range of from 100:1 to 1:100, of from 50:1 to 1:10, of from 25:1 to 1:5, of from 10:1 to 1:1, of from 9:1 to :2: 1, of approximately 9:1, of approximately 8:1, of approximately 7:1, of approximately 6:1, of approximately 5:1, of approximately 4:1, of approximately 3:1, or of approximately 2:1.As used herein, the term "stereoisomers of menthyl acetate” may be understood in the broadest sense as any stereoisomer of menthyl acetate. Such any stereoisomer of menthyl acetate may include (-)-menthyl acetate, (+)-menthyl acetate, (+)-isomenthyl acetate, (-)-isomenthyl acetate, (+)-neomenthyl acetate, (-)-neomenthyl acetate, (+)-neoisomenthyl acetate, (-)-neoisomenthyl acetate, or a combination of two or more thereof. In a preferred embodiment, the composition of the present invention comprises at least 0.5 wt.%, preferably at least 1 wt.%, more preferably at least 2 wt.%, in particular at least 3 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate. The composition of the present invention may comprise any contents of the one or more stereoisomers of menthyl acetate. In a preferred embodiment, the composition comprises 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate.

[0052] As used herein, the term "stereoisomers of isopulegol” may be understood in the broadest sense as any stereoisomer of isopulegol. Such any stereoisomer of isopulegol may include (-)-isopulegol, (+)-isopulegol, (+)-iso-isopulegol, (-)-iso-isopulegol, (+)-neo-isopulegol, (-)-neo-isopulegol, (+)-neoiso-isopulegol, (-)-neoiso-isopulegol, or a combination of two or more thereof. In a preferred embodiment, the composition of the present invention comprises at least 0.5 wt.%, preferably at least 1 wt.%, more preferably at least 1.5 wt.%, in particular at least 2 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol. The composition of the present invention may comprise any contents of the one or more stereoisomers of isopulegol. In a preferred embodiment, the composition comprises 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol.

[0053] As used herein, the term "stereoisomers of linalool” may be understood in the broadest sense as any stereoisomer of linalool, including (S)-(+)-linalool, (R)-(— )-linalool, or a combination of both. In a preferred embodiment, the composition of the present invention comprises at least 0.005 wt.%, preferably at least 0.01 wt.%, more preferably at least 0.02 wt.%, in particular at least 0.03 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of linalool. The composition of the present invention may comprise any contents of the one or more stereoisomers of linalool. In a preferred embodiment, the composition comprises 0.001 to 10 wt.%, preferably 0.005 to 2 wt.%, in particular 0.01 to 1 wt.%, related to the total mass of the composition as a whole, of one or both stereoisomers of linalool.

[0054] As noted above, the content ranges of menthofuran and pulegone are comparably low or these components are virtually absent or even completely absent.

[0055] In a preferred embodiment, the composition does not comprise more than 10 ppm, preferably does not comprise more than 1 ppm, in particular does not comprise more than 0.1 ppm, related to the total mass of the composition as a whole, of menthofuran.In a preferred embodiment, the composition does not comprise more than 0.2 wt.%, preferably does not comprise more than 0.1 wt.%, more preferably does not comprise more than 500 ppm, in particular does not comprise more than 100 ppm, of pulegone.

[0056] In a preferred embodiment, the composition is further characterized in that:

[0057] (a) it does not comprise more than 10 ppm, preferably does not comprise more than 1 ppm, in particular does not comprise more than 0.1 ppm, related to the total mass of the composition as a whole, of menthofuran; and

[0058] (b) it does not comprise more than 0.2 wt.%, preferably does not comprise more than 0.1 wt.%, more preferably does not comprise more than 500 ppm, in particular does not comprise more than 100 ppm, of pulegone.

[0059] The composition may comprise the above-mentioned components (A) to (E) in any content ranges, optionally in addition with one or more further components.

[0060] In a preferred embodiment, the total content of components (A) to (E) is at least 75 wt.%, preferably at least 80 wt.%, in particular at least 95 wt.%, related to the total mass of the composition as a whole.

[0061] In other words, at least 75 wt.%, preferably at least 80 wt.%, in particular at least 95 wt.% of the composition is composed of components (A) to (E):

[0062] (A) one or more stereoisomers of menthol;

[0063] (B) one or more stereoisomers of menthone;

[0064] (C) one or more stereoisomers of menthyl acetate;

[0065] (D) one or more stereoisomers of isopulegol; and

[0066] (E) one or both stereoisomers of linalool.

[0067] As indicated above, the composition may comprise the components (A) to (E) in different weight contents. In a preferred embodiments, the composition comprises:

[0068] (A) 10 to 80 wt.%, preferably 25 to 70 wt.%, in particular 30 to 60 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol;

[0069] (B) 20 to 70 wt.%, preferably 15 to 50 wt.%, in particular 20 to 40 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone;

[0070] (C) 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate;

[0071] (D) 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol; and(E) 0.001 to 10 wt.%, preferably 0.005 to 2 wt.%, in particular 0.01 to 1 wt.%, related to the total mass of the composition as a whole, of one or both stereoisomers of linalool,

[0072] preferably wherein the total content of components (A) to (E) is at least 75 wt.%, preferably at least 80 wt.%, in particular at least 95 wt.%, related to the total mass of the composition as a whole.

[0073] As indicated above, the composition of the present invention may optionally comprise one or more further compounds that may optionally have an impact on its scent and / or aroma. In a preferred embodiment, the composition further comprises one or more of the components selected from the group consisting of eucalyptol, piperitone, pinene, (-)-carvone, germacrene, alpha-pinene, beta-pinene, terpinen-4-ol, terpineol, octan-3-ol, sabinene, terpinolene, octyl acetate, cis-3-hexenol, linalool oxide, gamma-decalactone, heptalactone, carvacrol, jasmone, thymol, and phenylethyl alcohol, and a combination of two or more thereof.

[0074] In a preferred embodiment, the composition further comprises one or more of the components selected from the group consisting of eucalyptol, piperitone, pinene, (-)-carvone, germacrene, and a combination of two or more thereof.

[0075] Optionally, the composition of the present invention may comprise germacrene. Germacrene may also be designated as (1 E,5E,8S)-1 ,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1 ,5-diene, (E,E)-germacra-3,9, 11 -triene, (1 E,5E,8S)-1 ,5-dimethyl-8-(1-methylethenyl)-1 ,5-cyclodecadiene, or (S-(E,E))-1 ,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene

[0076] Identifiers. As used herein, germacrene may be of any stereoisomer or mixture of two or more thereof. For instance, germacrene may germacrene A and / or germacrene D. Germacrene is a sesquiterpene. If present, germacrene may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 20 wt.%, preferably 0.01 to 0.5 wt.%, in particular 0.02 to 0.1 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of germacrene.

[0077] Optionally, the composition of the present invention may comprise beta-caryophyllene. As used herein, betacaryophyllene may be any stereoisomer thereof. As used herein, the term "stereoisomers of beta-caryophyllene” may be understood in the broadest sense as in the broadest sense as any stereoisomer of beta-caryophyllene. In a preferred embodiment, the composition of the present invention comprises at least 0.05 wt.%, preferably at least 0.1 wt.%, more preferably at least 0.2 wt.%, in particular at least 0.25 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of beta-caryophyllene. The composition of the present invention may comprise any contents of the one or more stereoisomers of beta-caryophyllene. In a preferred embodiment, the composition comprises 0.01 to 5 wt.%, preferably 0.05 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of beta-caryophyllene.Optionally, the composition of the present invention may comprise eucalyptol. Eucalyptol may also be designated as cineol, 1 ,8-cineol, or 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane. If present, eucalyptol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 20 wt.%, preferably 0.1 to 10 wt.%, in particular 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of eucalyptol.

[0078] Optionally, the composition of the present invention may comprise piperitone. Piperitone may also be designated as 6-isopropyl-3-methyl-1-cyclohex-2-enone, 3-carvomenthenone, or p-menth-1-en-3-one. If present, piperitone may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.1 to 10 wt.%, in particular 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of piperitone.

[0079] Optionally, the composition of the present invention may comprise alpha-pinene. If present, alpha-pinene may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of alpha-pinene.

[0080] Optionally, the composition of the present invention may comprise beta-pinene. If present, beta-pinene may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of beta-pinene.

[0081] Optionally, the composition of the present invention may comprise terpinen-4-ol (also 4-Methyl-1-(propan-2-yl)cyclohex-3-en-1-ol). If present, terpinen-4-ol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of terpinen-4-ol.

[0082] Optionally, the composition of the present invention may comprise terpineol ((-)-alpha-terpineol and / or (+)-alpha-terpineol and / or beta-terpineol and / or gamma-terpineol and / or delta-terpineol). If present terpineol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of terpineol. Optionally, the composition of the present invention may comprise alpha-terpineol ((-)-alpha-terpineol and / or (+)-alpha-terpineol). If present alpha-terpineol ((-)-alpha-terpineol and / or (+)-alpha-terpineol) may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of alpha-terpineol ((-)-alpha-terpineol and / or (+)-alpha-terpineol).Optionally, the composition of the present invention may comprise (-)-carvone. If present, (-)-carvone may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of (-)-carvone.

[0083] Optionally, the composition of the present invention may comprise octan-3-ol. If present, octan-3-ol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 2 wt.%, preferably 0.01 to 1 wt.%, in particular 0.05 to 0.5 wt.%, related to the total mass of the composition as a whole, of octan-3-ol.

[0084] Optionally, the composition of the present invention may comprise sabinene (4-methylene-1-(1-methylethyl)bicyclo[3.1.0]hexane). If present, sabinene may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.001 to 0.5 wt.%, in particular 0.01 to 0.1 wt.%, related to the total mass of the composition as a whole, of sabinene.

[0085] Optionally, the composition of the present invention may comprise terpinolene (1-Methyl-4-propan-2-ylidencyclohexen). If present, terpinolene may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.001 to 0.5 wt.%, in particular 0.01 to 0.1 wt.%, related to the total mass of the composition as a whole, of terpinolene.

[0086] Optionally, the composition of the present invention may comprise octyl acetate. If present, octyl acetate may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.001 to 0.5 wt.%, in particular 0.01 to 0.1 wt.%, related to the total mass of the composition as a whole, of octyl acetate.

[0087] Optionally, the composition of the present invention may comprise cis-3-hexenol. If present, cis-3-hexenol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.001 to 0.5 wt.%, in particular 0.01 to 0.1 wt.%, related to the total mass of the composition as a whole, of cis-3-hexenol.

[0088] Optionally, the composition of the present invention may comprise linalool oxide. If present, linalool oxide may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.001 to 0.5 wt.%, in particular 0.01 to 0.1 wt.%, related to the total mass of the composition as a whole, of linalool oxide.

[0089] Optionally, the composition of the present invention may comprise gamma-decalactone. If present, gammadecalactone may be comprised in the composition in any content. In a preferred embodiment, the compositionmay comprise 0 to 2 wt.%, preferably 0.0001 to 1 wt.%, in particular 0.0005 to 0.5 wt.%, related to the total mass of the composition as a whole, of gamma-decalactone.

[0090] Optionally, the composition of the present invention may comprise heptalactone. If present, heptalactone may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.00001 to 0.5 wt.%, in particular 0.0001 to 0.1 wt.%, related to the total mass of the composition as a whole, of heptalactone.

[0091] Optionally, the composition of the present invention may comprise carvacrol. If present, carvacrol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.0001 to 0.5 wt.%, in particular 0.001 to 0.1 wt.%, related to the total mass of the composition as a whole, of carvacrol.

[0092] Optionally, the composition of the present invention may comprise jasmone (in particular cis-jasmone). If present, jasmone (in particular cis-jasmone) may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.0001 to 0.5 wt.%, in particular 0.0001 to 0.01 wt.%, related to the total mass of the composition as a whole, of jasmone (in particular cis-jasmone).

[0093] Optionally, the composition of the present invention may comprise thymol. If present thymol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.0001 to 0.5 wt.%, in particular 0.0001 to 0.01 wt.%, related to the total mass of the composition as a whole, of thymol.

[0094] Optionally, the composition of the present invention may comprise phenylethyl alcohol. If present phenylethyl alcohol may be comprised in the composition in any content. In a preferred embodiment, the composition may comprise 0 to 1 wt.%, preferably 0.0001 to 0.5 wt.%, in particular 0.0005 to 0.1 wt.%, related to the total mass of the composition as a whole, of phenylethyl alcohol.

[0095] In a preferred embodiments, the composition comprises or consists of:

[0096] (A) 10 to 80 wt.%, preferably 25 to 70 wt.%, in particular 30 to 60 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol;

[0097] (B) 20 to 70 wt.%, preferably 15 to 50 wt.%, in particular 20 to 40 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone;

[0098] (C) 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate;(D) 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol;

[0099] (E) 0.001 to 10 wt.%, preferably 0.005 to 2 wt.%, in particular 0.01 to 1 wt.%, related to the total mass of the composition as a whole, of one or both stereoisomers of linalool;

[0100] (F) 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of beta-caryophyllene;

[0101] (G) 0 to 20 wt.%, preferably 0.01 to 0.5 wt.%, in particular 0.02 to 0.1 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of germacrene;

[0102] (H) 0 to 20 wt.%, preferably 0.1 to 10 wt.%, in particular 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of eucalyptol;

[0103] (I) 0 to 5 wt.%, preferably 0.1 to 10 wt.%, in particular 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of piperitone; and

[0104] (J) 0 to 20 wt.%, preferably 0.05 to 10 wt.%, in particular 0.1 to 5 wt.%, related to the total mass of the composition as a whole, of one or more further aroma ingredients different from (A) to (I).

[0105] The composition of the present invention may comprise the components (A) to (J) in any total content. In a preferred embodiment, the total content of components (A) to (J) (i.e., the sum of all components (A), (b), (C), (D), (E); (F), G), (H), (I), and (J)) is at least 75 wt.%, preferably at least 80 wt.%, more preferably at least 95 wt.%, in particular at least 99 wt.%, related to the total mass of the composition as a whole.

[0106] In a preferred embodiment, the composition comprises or consists of:

[0107] (A) 30 to 60 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol, wherein the one or more stereoisomers of menthol consist of:

[0108] (A1) 10 to 75 wt.%, related to the total content of stereoisomers of menthol, of (-)-menthol, (A3) 5 to 50 wt.%, related to the total content of stereoisomers of menthol, of (+)-menthol,

[0109] (A3) 5 to 70 wt.%, related to the total content of stereoisomers of menthol, of neomenthol, and (A4) 0 to 10 wt.%, related to the total content of stereoisomers of menthol, of one or more stereoisomers different from (A1), (A2) and (A3);

[0110] (B) 20 to 40 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone;

[0111] (C) 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate;

[0112] (D) 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol;

[0113] (E) 0.01 to 1 wt.%, related to the total mass of the composition as a whole, of one or both stereoisomers of linalool;(F) 0.1 to 3 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of beta-caryophyllene;

[0114] (G) 0.01 to 0.5 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of germacrene;

[0115] (H) 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of eucalyptol;

[0116] (I) 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of piperitone; and

[0117] (J) 0 to 5 wt.%, related to the total mass of the composition as a whole, of one or more further aroma ingredients different from (A) to (I),

[0118] preferably wherein the total content of components (A) to (J) is at least 75 wt.%, preferably at least 80 wt.%, more preferably at least 95 wt.%, in particular at least 99 wt.%, related to the total mass of the composition as a whole.

[0119] The composition of the present invention may or may not comprise other scent or aroma components such as limonene (i.e., (-)-limonene and (+)-limonene), myrcene (7-methyl-3-methylen-1,6-octadien), p-cymol, beta-bourbonene, beta-elemene and / or lavandulol (5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol).

[0120] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of limonene (i.e., (-)-limonene and (+)-limonene) or may comprise (-)-limonene and / or (+)-limonene. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of limonene (i.e., (-)-limonene and (+)-limonene).

[0121] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of myrcene (7-methyl-3-methylen-1,6-octadien) or may comprise myrcene. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of myrcene.

[0122] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of p-cymol or may comprise p-cymol. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of p-cymol.

[0123] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of ocimene or may comprise ocimene. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise morethan 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of ocimene.

[0124] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of beta-bourbonene or may comprise beta-bourbonene. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of beta-bourbonene.

[0125] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of beta-elemene or may comprise beta-elemene. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of beta-elemene.

[0126] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of lavandulol (5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol) or may comprise lavandulol. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of lavandulol.

[0127] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of decanol or may comprise decanol. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of decanol.

[0128] Optionally, the composition of the present invention may be virtually free of or may merely contain minimized contents of camphene or may comprise camphene. In a preferred embodiment, the composition does not comprise more than 0.1 wt.%, preferably does not comprise more than 100 ppm, more preferably does not comprise more than 10 ppm, in particular does not comprise more than 1 ppm, related to the total mass of the composition as a whole, of camphene.

[0129] The compounds of the composition of the present invention may be obtained from any means such as from commercial sources. The person skilled in the art knows sources of the components. In principle, the compounds may be of synthetic origin, bacterial origin, fungal origin, animal origin, or plant origin. In a preferred embodiment,at least at least 75 wt.%, preferably at least 90 wt.%, in particular at least 95wt.%, of the organic compounds of the composition is not of plant origin, in particular is of synthetic and / or bacterial origin.

[0130] The person skilled in the art will understand that the composition of the present invention may be obtained by any means. In particular, it may be obtained by mixing two or more components with each other.

[0131] Accordingly, a further aspect of the present invention relates to a method for preparing a composition having a mint aroma of the present invention, comprising the steps of:

[0132] (i) providing:

[0133] (i-1) one or more compositions each comprising:

[0134] (A) one or more stereoisomers of menthol; and

[0135] (i-2) one or more compositions separate from the one or more compositions (i-1), comprising (or consistingof) in sum:

[0136] (B) one or more stereoisomers of menthone;

[0137] (C) one or more stereoisomers of menthyl acetate;

[0138] (D) one or more stereoisomers of isopulegol; and

[0139] (E) one or both stereoisomers of linalool; and

[0140] optionally one or more further ingredients, and

[0141] (ii) mixing the one or more compositions (A) comprising one or more stereoisomers of menthol and the one or more compositions (B) to (E) with each other and optionally with further components to obtain the composition having a mint aroma.

[0142] It will be understood that the definitions and preferred embodiments as laid out in the context of the composition of the present invention may mutatis mutandis apply to the method of the present invention.

[0143] Mixing may be performed by any means such as in a container such as vessel. Mixing may or may not involve heating. Mixing may be mixing of gaseous, liquid, viscous, pasty and / or solid components, in particular of liquid viscous, pasty and / or solid components.

[0144] The present invention also refers to a composition obtainable (or obtained) from a method of the present invention.

[0145] The person skilled in the art will understand that the composition of the present invention may be mixed with one or more other compounds, in particular those compounds which are not aroma ingredients. An obtained formulation may comprise any amounts of the composition of the present invention.

[0146] Accordingly, a further aspect of the present invention relates to a formulation comprising or consisting of:(1) 0.01 to 99.9 wt.%, preferably 0.1 to 99 wt.%, in particular 1 to 50 wt.%, related to the total mass of the formulation as a whole, of a composition of the present invention; and

[0147] (2) 0.01 to 99.9 wt.%, preferably 1 to 99.9 wt.%, in particular 50 to 99 wt.%, related to the total mass of the formulation as a whole, of one or more further ingredients different from that of the composition of (1), wherein the formulation does not comprise more than 100 ppm, related to the total mass of the formulation as a whole, of menthofuran, and

[0148] preferably wherein the formulation does not comprise more than 0.5 wt.%, related to the total mass of the formulation as a whole, of pulegone.

[0149] It will be understood that the definitions and preferred embodiments as laid out in the context of the composition of the present invention may mutatis mutandis apply to the formulation of the present invention.

[0150] The term "formulation” may be understood in the broadest sense as any mixture comprising the composition of the present invention. It may be a liquid, viscous, pasty and / or solid formulation. In a preferred embodiment, the formulation is liquid or viscous. In a preferred embodiment, the formulation is a cosmetically acceptable and / or pharmaceutically acceptable and / or consumable formulation.

[0151] The one or more further ingredients different from that of the composition of (1) may be any compound. In a preferred embodiment, the one or more further ingredients are pharmaceutically and / or cosmetically acceptable and / or consumable in the used content ranges. In a preferred embodiment, the one or more further one or more further ingredients different from that of the composition of (1) as comprised in the formulation of the present invention are selected from the group consisting of:

[0152] (2a) one or more organic solvents, preferably one or more cosmetically and / or pharmaceutically acceptable organic solvents, in particular one or more organic solvents selected from the group consisting of linear or branched C2-C10 alkanol, one or more tri- and / or diglycerides, one or more fatty acids, dimethyl sulfoxide, and a combination of two or more thereof;

[0153] (2b) water or an aqueous solution, preferably a cosmetically and / or pharmaceutically acceptable aqueous solution, optionally in combination with one or more emulsifying agents; and

[0154] (2c) one or more further ingredients dissolved in any of (2a) or (2b), preferably wherein the one or more further ingredients are cosmetically and / or pharmaceutically acceptable, in particular wherein the one or more further ingredients are selected from the group consisting of preserving agents, coloring agents, antioxidants, thickening agents, fillers, food additive (e.g., triacetin) and combinations of two or more thereof; and

[0155] (2d) a combination of two or more of (2a), (2b) and (2c).

[0156] The person skilled in the art will understand that the composition or the formulation of the present invention may form part of a product.Accordingly, a further aspect of the present invention relates to a product comprising a composition of the present invention or a formulation of the present invention.

[0157] It will be understood that the definitions and preferred embodiments as laid out in the context of the composition and the formulation of the present invention may mutatis mutandis apply to the product of the present invention.

[0158] The product may comprise any content of the composition of the present invention. In a preferred embodiment, the product comprises 0.001 to 99.9 wt.%, preferably 0.01 to 99.9 wt.%, in particular 0.1 to 99 wt.%, such as, e.g., 0.01 to 5 wt.%, 0.1 to 25 wt.%, or 1 to 75 wt.%, related to the total mass of the product as a whole, of a composition of the present invention.

[0159] The product may be any product. In a preferred embodiment, it is a product that typically contains mint oil of DMO. In a preferred embodiment, the product is selected from the group consisting of:

[0160] a personal care or cosmetic product, in particular toothpaste, mouthwash, dental floss, denture cleaner, toothpowder, a shower gel, a soap, a shampoo, a conditioner, a hair gel, a hair spray, a cream, a cosmetic oil, a lotion, a sun protectant, a make-up, a lipstick, a shaving gel / foam / cream, or hairspray;

[0161] a consumable product, in particular chewing gum, candy, flavored chocolate, a bakery good, a cream, a sauce, or a flavored beverage or drink, or an instant product for preparing one of the aforementioned;

[0162] a repellent, in particular an evaporated insect repellent;

[0163] a fragrance product, in particular a fine fragrance, perfume, Eau de Solide, Eau de Cologne, Eau de Toilette, Eau de Parfum, Extrait Parfum, an aftershave, or an antiperspirant; and

[0164] a flavoring additive of an inhalable vaporizable liquid or a smokable good;

[0165] a household product, in particular a general cleaner, toilet cleaner, an acid cleaner, a laundry agent, a dishwashing agent, another detergent, or a softener;

[0166] a pharmaceutical composition, in particular an inhalable composition or instant for preparing such, a capsule, a pill, a gel, a cream, an ointment, a lotion, a sirup, or a drinkable pharmaceutical composition;

[0167] and a combination of two or more thereof.

[0168] The composition of the present invention, the formulation of the present invention and the product of the present invention may be used for any purpose.

[0169] As indicated above, the composition of the present invention bears the advantage that undesired components such as menthofuran, pulegone, xenobiotics, and toxins can be widely avoided, and the content ranges of all components are well controllable and adjustable. This makes the composition of the present invention and formulations and product containing such particularly useful in therapeutic and cosmetic contexts.A further aspect of the present invention relates to the composition of the present invention, the formulation of the present invention or the product of the present invention for use as medicament.

[0170] A further aspect of the present invention relates to the composition of the present invention, the formulation of the present invention, or the present invention for use in a method of preventing or treating a pathologic condition and / or symptoms thereof selected from the group consisting of infect of the upper respiratory tract and / or the mucosa in the mouth, in particular of the respiratory mucosa of the nose, throat, sinuses, and / or larynx, tympany, meteorism, irritable bowel syndrome, catarrh, colic, in particular biliary colic, halitosis, and / or cephalalgia.

[0171] In other words, the present invention relates to a method of preventing or treating a pathologic condition and / or symptoms thereof selected from the group consisting of infect of the upper respiratory tract and / or the mucosa in the mouth, in particular of the respiratory mucosa of the nose, throat, sinuses, and / or larynx, tympany, meteorism, irritable bowel syndrome, catarrh, colic, in particular biliary colic, halitosis, and / or cephalalgia in a patient in need thereof, wherein a sufficient amount of the composition of the present invention, the formulation of the present invention, or the present invention is administered to the patient in need thereof.

[0172] It will be understood that the definitions and preferred embodiments as laid out in the context of the composition, the formulation and the product of the present invention may mutatis mutandis apply to the therapeutic uses and methods of the present invention.

[0173] As used herein, the term "patient” may be understood in the broadest sense as any living being that is treatable. In a preferred embodiment, a patient is a human or an animal, preferably a human or a mammal, more preferably a human or a domestic mammal such as a dog, a cat, a bovine, a horse, a donkey, or a camel, in particular a patient is a human.

[0174] The patient may be administered with the composition of the present invention, the formulation of the present invention or the product of the present invention by any means. For instance, administration may be nasal, oral, or topical administration. Administration may be achieved by inhalation (e.g., by an inhalator), as an aerosol (e.g., as a spray), as an ointment, as a cream, or as a liquid, as a sirup, as a capsule, or as a tablet.

[0175] As indicated above, the composition of the present invention is usable as a substitute of mint oil of natural origin or dementholized mint oil (DMO) derived therefrom.

[0176] Accordingly, a further aspect of the present invention relates to the use of the composition of the present invention or a formulation of the present invention for substituting mint oil of plant origin or of dementholized mint oil (DMO) derived from mint oil of plant origin, in particular of mint oil of Mentha arvensis or DMO derived therefrom.It will be understood that the definitions and preferred embodiments as laid out in the context of the composition and the formulation of the present invention may mutatis mutandis apply to the use as a substitute of the present invention.

[0177] Such substitute may replace the mint oil of plant origin or of DMO derived from mint oil of plant origin in a certain use such as a certain product partly or completely. In a preferred embodiment, at least 25 wt.%, preferably at least 50 wt.%, more preferably at least 75 wt.%, in particular (virtually) the whole content of mint oil of plant origin or of DMO derived from mint oil of plant origin is replaced by the composition of the present invention or a formulation of the present invention. Accordingly, a respective product that typically contains mint oil of plant origin or of DMO derived from mint oil of plant origin does (essentially) not comprise mint oil of plant origin or of DMO derived from mint oil of plant origin. This may save natural resources, may allow avoidance of toxic components such as menthofuran and pulegone and undesired xenobiotics, and may allow precise desired product characteristics.

[0178] The experimental examples are intended to illustrate and exemplify the invention further, but do not limit the scope thereof which is defined by the spirit of the claims.

[0179] Examples

[0180] Examples 1 to 5

[0181] Compositions substituting dementholized mint oil (DMO)

[0182] Several synthetic compositions of were prepared and their aroma perception was compared with the aroma perception of dementholized mint oil (DMO) obtained from the natural source corn mint {Mentha arvensis). The content rations of the respective synthetic DMO compositions are depicted in Table 1 below. Notable, all compositions of Examples 1 to 5 are free of significant contents of menthofuran and pulegone as typically occurring in higher contents in DMO of plant origin (natural DMO) obtained from the natural source Mentha arvensis obtained from natural sources.

[0183] Table 1. Compared compositions (in parts by weight)

[0184]

[0185]

[0186] The above compositions as well as DMO of plant origin were each mixed in a weight ration of 1:10 with ethanol (i.e., 0.5 g of the respective composition mixed with 4.5 g ethanol) to obtain an ethanolic solution. The obtained ethanolic solutions were each mixed with a fondant (Sprayable Fondant, composed of sucrose, glucose syrup and water, obtainable from Nordzucker AG, Germany) in a weight ratio of 1 :200 (0.1 g of ethanolic solution to 20 g fondant. In summary, each composition of Examples 1 to 5 as well as natural DMO were each present in the fondant samples in a concentration of 0.05 wt.%.The fondant samples were tested by blind testing with three experienced persons tasting the samples independently with respect to their aroma perception. In this context, the similarity to the DMO of plant origin was determined and evaluated. The results are depicted in Table 2 below.

[0187] Table 2. Similarity to the dementholized mint oil (DMO) obtained from the natural source Mentha arvensis

[0188]

[0189] Herein: "+++” means at least highly similar or (virtually) identical to natural DMO, "++” means similar to natural DMO, “+” means reminiscent to natural DMO, and means clearly different from natural DMO

[0190] The positive control (fondant sample comprising DMO of plant origin) was correctly identified as having a typical DMO-like aroma perception. The complex mixtures Examples Ex.1 and 2 were identified as at least highly similar. The mixture of menthol and menthone (Ex.4) was noted as having notable similarity to the DMO of plant origin (benchmark), but somewhat lower similarity than Ex.1 and 2. The use of menthol alone or in combination with menthyl acetate is still reminiscent of DMO, but more clearly distinguishable. Thus, to obtain a particularly desired taste perception, it does not seem sufficient to mix menthol with menthone or menthyl acetate alone. It has been found that a composition comprising one or more stereoisomers of menthol, of menthone, of menthyl acetate, of isopulegol, and of linalool leads to particularly beneficial results. Germacrene was found as an optionally further improving component.

[0191] In summary, it was surprisingly found that substitutes of DMO of plant origin that bear an aroma perception that is at least highly similar to or even not distinguishable from DMO of plant origin can be obtained. Surprisingly, the aroma components menthofuran and pulegone did not have to be added to obtain such desirable taste perception.

[0192] Example 6

[0193] Compositions substituting (non or only partly dementholized) mint oilThe above compositions, in particular compositions of Examples 1 and 2, can comprise additional menthol, in particular (-)-menthol. For instance, 10 to 80 wt.%, referred to the total mass of the terpenes, of additional (-)-menthol may be added. Such composition may bear a full mint aroma perception of (non-dementholized) mint oil. The exact content range f (-)-menthol can be adjusted to the desired purpose and strength of freshness. This is a further technical advantage over the prior art.

[0194] Example 7

[0195] Exemplified uses

[0196] The synthetic DMO of the present invention, for instance of Example 1 or 2, or a (non-dementholized) mint oil of the present invention, for instance of Example 6, may be used for any purpose such as in consumer goods such as, e.g., toothpaste, chewing gum, etc.. For instance, it may be used to partly or completely substitute DMO of plant origin, mint oil or a fraction thereof of plant origin in the respective consumer goods. The content ranges may be optionally the same as the substituted DMO of plant origin, mint oil or a fraction thereof of plant origin. The content ranges of components such as, e.g., (-)-menthol can be adapted to the desired aroma perception and strength.

Claims

CLAIMS1. A composition having a mint aroma, comprising:(A) one or more stereoisomers of menthol;(B) one or more stereoisomers of menthone;(C) one or more stereoisomers of menthyl acetate;(D) one or more stereoisomers of isopulegol; and(E) one or both stereoisomers of linalool; andwherein the composition does not comprise more than 100 ppm, related to the total mass of the composition as a whole, of menthofuran,and wherein the composition does not comprise more than 0.25 wt.%, related to the total mass of the composition as a whole, of pulegone.

2. The composition of claim 1 , wherein the composition is further characterized in that:(a) it does not comprise more than 10 ppm, preferably does not comprise more than 1 ppm, in particular does not comprise more than 0.1 ppm, related to the total mass of the composition as a whole, of menthofuran; and / or(b) it does not comprise more than 0.2 wt.%, preferably does not comprise more than 0.1 wt.%, more preferably does not comprise more than 500 ppm, in particular does not comprise more than 100 ppm, of pulegone.

3. The composition of any one of claims 1 or 2, wherein the total content of components (A) to (E) is at least 75 wt.%, preferably at least 80 wt.%, in particular at least 95 wt.%, related to the total mass of the composition as a whole.

4. The composition of any one of claims 1 to 3, wherein the one or more stereoisomers of menthone comprise (-)-menthone and (+)-menthone in a mass ratio of (-)-menthone : (+)-menthone of from 1:9 to 9:1, preferably wherein the composition comprises at least 10 wt.%, related to the total mass of the composition as a whole, of stereoisomers of menthone.

5. The composition of any one of claims 1 to 4, wherein the one or more stereoisomers of menthol comprise:(A1) 10 to 75 wt.%, preferably 25 to 70 wt.%, related to the total mass of stereoisomers of menthol, of (-)-menthol;(A2) 5 to 50 wt.%, preferably 10 to 40 wt.%, related to the total mass of stereoisomers of menthol, of (+)-menthol; and(A3) 1 to 70 wt.%, preferably, 5 to 40 wt.%, related to the total mass of stereoisomers of menthol, of neomenthol,and wherein the total mass of (-)-menthol, (+)-menthol and neomenthol sums up to at least 75 wt.%, preferably of at least 90 wt.%, in particular at least 95 wt.%, of the total mass of stereoisomers of menthol.

6. The composition of any one of claims 1 to 5, wherein at least at least 75 wt.%, preferably at least 90 wt.%, in particular at least 95wt.%, of the organic compounds of the composition is not of plant origin, in particular is of synthetic and / or bacterial origin.

7. The composition of any one of claims 1 to 6, wherein the composition comprises at least 2 wt.%, preferably between 3 and 40 wt.%, more preferably between 4 and 30 wt.%, in particular between 10 and 25 wt.%, related to the total mass of the composition as a whole, of neomenthol.

8. The composition of any one of claims 1 to 7, wherein the composition further comprises one or more of the components selected from the group consisting of eucalyptol, piperitone, pinene, (-)-carvone, germacrene, and a combination of two or more thereof.

9. The composition of any one of claims 1 to 8, wherein the composition comprises or consists of:(A) 10 to 80 wt.%, preferably 25 to 70 wt.%, in particular 30 to 60 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol;(B) 20 to 70 wt.%, preferably 15 to 50 wt.%, in particular 20 to 40 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone;(C) 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate;(D) 0.5 to 20 wt.%, preferably 1 to 20 wt.%, in particular 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol;(E) 0.001 to 10 wt.%, preferably 0.005 to 2 wt.%, in particular 0.01 to 1 wt.%, related to the total mass of the composition as a whole, of one or both stereoisomers of linalool;(F) 0 to 5 wt.%, preferably 0.01 to 2 wt.%, in particular 0.1 to 1 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of beta-caryophyllene;(G) 0 to 20 wt.%, preferably 0.01 to 0.5 wt.%, in particular 0.02 to 0.1 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of germacrene;(H) 0 to 20 wt.%, preferably 0.1 to 10 wt.%, in particular 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of eucalyptol;(I) 0 to 5 wt.%, preferably 0.1 to 10 wt.%, in particular 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of piperitone; and(J) 0 to 20 wt.%, preferably 0.05 to 10 wt.%, in particular 0.1 to 5 wt.%, related to the total mass of the composition as a whole, of one or more further aroma ingredients different from (A) to (I), preferably wherein the total content of components (A) to (J) is at least 75 wt.%, preferably at least 80 wt.%, more preferably at least 95 wt.%, in particular at least 99 wt.%, related to the total mass of the composition as a whole.

10. The composition of any one of claims 1 to 9, wherein the composition comprises or consists of:(A) 30 to 60 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthol, wherein the one or more stereoisomers of menthol consist of:(A1) 10 to 75 wt.%, related to the total content of stereoisomers of menthol, of (-)-menthol, (A3) 5 to 50 wt.%, related to the total content of stereoisomers of menthol, of (+)-menthol, (A3) 5 to 70 wt.%, related to the total content of stereoisomers of menthol, of neomenthol, and (A4) 0 to 10 wt.%, related to the total content of stereoisomers of menthol, of one or more stereoisomers different from (A1), (A2) and (A3);(B) 20 to 40 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthone;(C) 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of menthyl acetate;(D) 2 to 10 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of isopulegol;(E) 0.01 to 1 wt.%, related to the total mass of the composition as a whole, of one or both stereoisomers of linalool;(F) 0.1 to 3 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of beta-caryophyllene;(G) 0.01 to 0.5 wt.%, related to the total mass of the composition as a whole, of one or more stereoisomers of germacrene;(H) 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of eucalyptol;(I) 0.5 to 5 wt.%, related to the total mass of the composition as a whole, of piperitone; and(J) 0 to 5 wt.%, related to the total mass of the composition as a whole, of one or more further aroma ingredients different from (A) to (I),preferably wherein the total content of components (A) to (J) is at least 75 wt.%, preferably at least 80 wt.%, more preferably at least 95 wt.%, in particular at least 99 wt.%, related to the total mass of the composition as a whole.

11. A formulation comprising or consisting of:(1) 0.01 to 99.9 wt.%, preferably 0.1 to 99 wt.%, in particular 1 to 50 wt.%, related to the total mass of the formulation as a whole, of a composition of any one or claims 1 to 10; and(2) 0.01 to 99.9 wt.%, preferably 1 to 99.9 wt.%, in particular 50 to 99 wt.%, related to the total mass of the formulation as a whole, of one or more further ingredients different from that of the composition of (1),wherein the formulation does not comprise more than 100 ppm, related to the total mass of the formulation as a whole, of menthofuran, andpreferably wherein the formulation does not comprise more than 0.5 wt.%, related to the total mass of the formulation as a whole, of pulegone,preferably wherein the formulation is a cosmetically acceptable and / or pharmaceutically acceptable and / or consumable formulation.

12. A product comprising a composition of any one or claims 1 to 10 or a formulation of claim 11, preferably wherein the product is selected from the group consisting of:a personal care or cosmetic product, in particular toothpaste, mouthwash, dental floss, denture cleaner, toothpowder, a shower gel, a soap, a shampoo, a conditioner, a hair gel, a hair spray, a cream, a cosmetic oil, a lotion, a sun protectant, a make-up, a lipstick, a shaving gel / foam / cream, or hairspray;a consumable product, in particular chewing gum, candy, flavored chocolate, a bakery good, a cream, a sauce, or a flavored beverage or drink, or an instant product for preparing one of the aforementioned;a repellent, in particular an evaporated insect repellent;a fragrance product, in particular a fine fragrance, perfume, Eau de Solide, Eau de Cologne, Eau de Toilette, Eau de Parfum, Extrait Parfum, an aftershave, or an antiperspirant; anda flavoring additive of an inhalable vaporizable liquid or a smokable good;a household product, in particular a general cleaner, toilet cleaner, an acid cleaner, a laundry agent, a dishwashing agent, another detergent, or a softener;a pharmaceutical composition, in particular an inhalable composition or instant for preparing such, a capsule, a pill, a gel, a cream, an ointment, a lotion, a sirup, or a drinkable pharmaceutical composition;and a combination of two or more thereof.

13. The composition of any one of claims 1 to 10, the formulation of claim 11, or the product of claim 12 for use in a method of preventing or treating a pathologic condition and / or symptoms thereof selected from the group consisting of infect of the upper respiratory tract and / or the mucosa in the mouth, in particular of the respiratory mucosa of the nose, throat, sinuses, and / or larynx, tympany, meteorism, irritable bowel syndrome, catarrh, colic, in particular biliary colic, halitosis, and / or cephalalgia.

14. A method for preparing a composition having a mint aroma of any of claims 1 to 10, comprising the steps of:(I) providing:(i-1) one or more compositions each comprising:(A) one or more stereoisomers of menthol; and(i-2) one or more compositions separate from the one or more compositions (i-1), comprising in sum:(B) one or more stereoisomers of menthone;(C) one or more stereoisomers of menthyl acetate;(D) one or more stereoisomers of isopulegol;(E) one or both stereoisomers of linalool; andoptionally one or more further ingredients, and(ii) mixing the one or more compositions (A) comprising one or more stereoisomers of menthol and the one or more compositions (B) to (E) with each other and optionally with further components to obtain the composition having a mint aroma.

15. Use of the composition of any one of claims 1 to 10 or a formulation of claim 11 for substituting mint oil of plant origin or of dementholized mint oil (DMO) derived from mint oil of plant origin, in particular of mint oil of Mentha arvensis or DMO derived therefrom.

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