EP2027101A1 - Trisubstituted furan derivatives as fragrances and aroma substances - Google Patents

Abstract

The invention concerns a use of a compound having formula (I) wherein: a first of the radicals R1, R2, R3 , R4 denotes hydrogen, a second of the radicals R1, R2, R3 , R4 denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R1, R2, R3, R4 mutually independently denote an alkyl or alkenyl radical having 1 to 6 C atoms, as a fragrance and/or aroma substance and/or as a means of rounding out and/or of imparting vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend.

Description

Symrise GmbH & Co. KG Mϋhlenfeldstraβe 1 , 37603 Holzminden

Trisubstituted furan derivatives as fragrances and aroma substances

The present invention concerns the use of certain trisubstituted furan derivatives having formula (I) (see below) as fragrances and aroma substances and/or as means of rounding out and/or imparting vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend. The invention also concerns certain perfumed or aromatised items which contain a sensorially effective amount of said trisubstituted furan derivatives and certain processes for imparting, modifying and/or strengthening certain scent or flavour impressions. Finally the invention also concerns novel trisubstituted furan derivatives which impart particular scent or flavour impressions.

Despite a multiplicity of fragrances and aroma substances already existing in the perfume and aroma industry, there is still a general need for novel fragrances and aroma substances which over and above their primary, in other words inherent, olfactory or gustatory characteristics have additional positive secondary characteristics, in blends with other fragrances or aroma substances, for example.

For the creation of novel modern compositions there is an ongoing need for fragrances and aroma substances with special olfactory/gustatory characteristics which are suitable for use as part of a composition of novel perfumes or aromas having a complex scent or flavour character. Thus fragrances and aroma substances are sought in particular which in addition to a herbal, spicy and/or hay-like scent or flavour note exhibit further notes and aspects which olfactory or gustatory.

Thus the object underlying this invention was substantially to find novel fragrances and aroma substances having a herbal, spicy and/or hay-like scent or flavour note, which are paired with further interesting and original olfactory or gustatory characteristics, as a consequence of which the sought-after fragrances and aroma substances make it possible to obtain novel and original fragrance and aroma compositions having specific notes and aspects. A fragrance or aroma substance to be provided should preferably have a hay-like note and thus be suitable as a substitute for coumarin.

According to the invention this object is achieved according to a first aspect by the use of a compound having formula (I)

(I)

wherein: a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R¹, R², R³, R⁴ mutually independently denote an alkyl or alkenyl radical having 1 to 6 C atoms,

as a fragrance and/or aroma substance

and/or as a means of rounding out and/or of imparting vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend.

Alkyl radicals in a compound having formula (I) can be straight-chain or branched. Alkenyl radicals in a compound having formula (I) can likewise be straight-chain or branched, and in addition they can have one or two C-C double bonds.

Taking into consideration any limitations on the number of C atoms, the following groups can be used as alkyl radicals in compounds for use according to the invention having formula (I): methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2- dimethylpropyl, 1 ,1 -dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2-trimethylpropyl.

The compound having formula (I) is a trisubstituted furan derivative.

Further aspects of the invention follow from the appended claims and the description below and relate in particular to perfumed or aromatised items (in particular fragrance or aroma compositions and food, oral care or consumable preparations) and processes.

The invention is based among other things on the surprising finding that the compounds having formula (I) as fragrances and aroma substances are suitable in particular for use in food, oral care or consumable preparations. It was also surprising that said compounds having formula (I) can be used to round out and/or to impart vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend. Although the total carbon number of a compound having formula (I) for use according to the invention can be varied within broad ranges, it is preferably not greater than 20, with particularly preferred compounds of formula (I) having a total carbon number of no more than 15. Compounds having formula (I) with a larger total carbon number are increasingly less volatile and therefore increasingly less suitable for use as a fragrance and/or aroma substance.

It follows from the above definition of the compounds having formula (I) for use according to the invention that their total carbon number is at least 9; compounds having formula (I) with a total carbon number of at least 10 are often preferred, however, with regard to olfactory perceptibility.

The use according to the invention of compounds having formula (I) is preferred in which: a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, a third of the radicals R¹, R², R³ , R⁴ denotes methyl or ethyl, and a fourth of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 1 to 4 C atoms.

The aforementioned comments regarding the preferred total carbon number still apply.

It has been found that compounds having formula (I) for use according to the invention which contain at least one methyl or ethyl group (but preferably at least one methyl group) have an advantage over such compounds having formula (I) which contain no methyl or ethyl group.

The use of a compound according to the invention having formula (I) is particularly preferred in which: a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R¹, R², R³, R⁴ mutually independently each denote methyl or ethyl, but preferably methyl.

These compounds having formula (I) are preferred because it has been found that compounds having formula (I) which contain at least two methyl or ethyl groups (preferably at least one methyl group, particularly preferably at least two methyl groups) have advantageous and generally more original gustatory and olfactory notes in comparison to compounds having formula (I) which do not satisfy this additional condition.

Compounds having formula (I) for use according to the invention which contain at least one methyl or ethyl group, but in particular those containing at least two methyl and/or ethyl groups, are particularly suitable for use in food, oral care or consumable preparations because of their outstanding olfactory and gustatory perceptibilities. In addition, as a fragrance and/or aroma substance they commonly induce one or more scent or flavour impressions from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage. Said compounds having formula (I) are especially suitable in particular for imparting, modifying and/or strengthening one or more of these sensorial impressions.

Depending on the individual scent or flavour characteristics, specific areas of application arise for the trisubstituted furan derivatives for use according to the invention. Thus, for example, compounds having formula (I) which in addition to a herbal note also have a hay-like note are particularly suitable as coumarin substitutes, for use for example in peppermint and/or spearmint aromas or peppermint and/or spearmint oils (see below). The use of compounds having formula (I) in which the radical R¹ is hydrogen is particularly preferred. Such compounds having formula (I) correspond to those having formula (II) below:

(H)

For a compound having formula (II) the following preferably applies: R² denotes methyl or ethyl, preferably methyl a first of the radicals R³ , R⁴ denotes methyl or ethyl, preferably methyl, a second of the radicals R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms.

Such a compound having formula (II) thus has a maximum total carbon number of 14 but preferably a maximum total carbon number of 12.

The use of compounds having formula (I) in which R¹ denotes hydrogen and R² denotes methyl is particularly preferred. Such compounds having formula (I) correspond to formula (III) below:

For the compound having formula (II) the following preferably applies: a first of the radicals R³ or R⁴ (preferably R³) denotes methyl and a second of the radicals R³ or R⁴ (preferably R⁴) denotes an alkyl radical having 3 to 6 C atoms, preferably n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl or 1 ,2,2-trimethylpropyl.

Although in the compounds having formula (III) as defined above the position of the (second) methyl can vary between R³ and R⁴, there is also a preferred arrangement, namely that in which R³ denotes methyl. R⁴ then denotes an alkyl radical having 3 to 6 C atoms (see above).

The use of a compound having formula (III) is most particularly preferred in which:

R³ denotes methyl and R⁴ denotes n-butyl or n-pentyl.

The fact that the trisubstituted furan derivatives having formula (I) for use according to the invention have a herbal, hay-like, coumarin-like and/or spicy (including celery, lovage, fennel, fenugreek notes) scent and/or flavour with further interesting aspects is particularly surprising because the structurally closest known sensorially active substances have completely different scent and flavour profiles (cf. in this respect the results of our own sensorial experiments below). In addition, the trisubstituted furan derivatives having formula (I) impart a very complex and multifaceted scent and flavour impression which can usually otherwise only be achieved with blends of several components (such as essential oils or mixtures of herbs, for example). In particular, the trisubstituted furan derivatives having formula (I) are suitable for imparting, modifying and/or strengthening a herbal, hay-like, coumarin-like and/or spicy scent or flavour note.

Our own experiments resulted in the sensorial characteristics specified below. The sensorial evaluation was made using the stated descriptors on the basis of a scale from 1 (very weak) to 9 (very strong).

By way of example, the sensorial characteristics of the trialkyl-substituted furans having formula (I) are described using the example of 3,4-dimethyl-2-n-C₃-C₆- alkylfurans, which are particularly preferred according to the invention (compound having formula (III) wherein R³ = CH₃). The tasting involved the sensorial evaluation of a mixture consisting of 5 wt.% of aqueous sugar solution and 1 ppm (based on the total weight of the aqueous sugar solution) of the particular 3,4- dimethyl-2-n-C₃-C₆-alkylfuran.

Table 1 : Sensorial characteristics of a number of 3,4-dimethyl-2-n-C₃-C₆- alkylfurans

The scent and flavour characteristics of 3,4-dimethyl-2-ethylfuran, which is not for use according to the invention, can be described by comparison as generally roasted/pyrazine-like [pyrazine, roasted (5), hazelnut (3), musty (3), cocoa (3), rancid (2)]. 3,4-Dimethyl-2-ethylfuran is a very strong (5) tasting substance which imparts moderate fullness (3) and has moderate staying power (3).

The scent and flavour characteristics of 3,4-dimethyl-2-n-heptylfuran, which is not for use according to the invention, can be described as generally oily/fatty [fatty, oily (3), milk (2), rancid (2), candy (2)]. 3,4-Dimethyl-2-n-heptylfuran is a very weak (3) tasting substance which imparts moderate fullness (3) and has low staying power (2).

In particular, the compounds having formula (III) for use according to the invention, in which R³ denotes methyl and R⁴ denotes an alkyl radical with 3 to 6 C atoms, i.e. 3,4-dimethyl-2-alkylfurans, have an extremely low sensorial threshold value, so they are perceptible even in very small amounts and can have a significant influence when incorporated into a fragrance or aroma composition. Cf. in this regard Table 2 below (in particular column 3).

Table 2: Odour thresholds of a number of dimethyl-2-pentylfurans from air (in ng/l air)

In mixtures with other fragrances and aroma substances, even in small amounts, the compounds having formula (I) according to the invention or for use according to the invention are capable of strengthening the intensity of a blend of fragrances or aroma substances and of rounding off the overall olfactory profile of the fragrance or aroma substance blend and of imparting greater vibrancy, roundness, naturalness (authenticity), fullness, complexity and/or staying power to the blend.

The invention also concerns a perfumed or aromatised item containing or consisting of:

(a) a sensorially effective amount of one or more compounds having formula (I) as described above (preferably in one of the embodiments identified above as being preferred), wherein at least one but preferably all compounds having formula (I) that are used are not yet known from the prior art (see below with regard to novel compounds having formula (I).

A perfumed or aromatised item according to the invention preferably includes or preferably consists of:

(a) a sensorially effective amount of one or more compounds having formula (I), as just stated,

(b) one, several or all compounds selected from the group consisting of

(i) menthol,

(ii) (-)-carvone

(iii) menthone and

(iv) isomenthone,

and preferably

(c) menthyl acetate.

The present invention also concerns perfumed or aromatised items containing or consisting of a sensorially effective amount of one or more compounds having formula (I), wherein the above statements regarding the meaning of the substituents R¹, R², R³ and R⁴ still apply. Such perfumed or aromatised items preferably contain a sensorially effective amount of one or more compounds having formula (I) not yet known from the prior art. In this respect reference is made at this point to the comments further on regarding novel compounds having formula (I).

Regardless of whether the compounds having formula (I) as defined above are novel or not, these compounds are particularly suitable for combining with one, several or all compounds selected from the group consisting of

(i) menthol,

(ii) (-)-carvone (iii) menthone and

(iv) isomenthone,

and preferably

menthyl acetate.

Particularly preferred for combining with substances (i), (ii), (iii) and (iv) are compounds having formula (I) which can impart one or more scent and flavour impressions from the group consisting of herbal, hay (like dried grass and slightly sweet) and coumarin. See in this respect the sensorial characteristics of 3,4- dimethyl-2-n-C₃-C₆-alkylfurans summarised in Table 1 above, which demonstrate the particular suitability of 3,4-dimethyl-2-n-butylfuran for being combined with compounds (i), (ii), (iii) and (iv).

Owing to the scent and flavour impressions which they impart, the compounds having formula (I) for use according to the invention can be used in particular in the production of aromas and oils which in terms of their sensorial (olfactory and/or gustatory) characteristics and preferably in terms of their consistency are extremely similar to natural peppermint and/or spearmint aromas or peppermint and/or spearmint oils. The terms sensorial reconstitution, recomposition or recreation of the natural aromas or oils are used in this connection. The (sensorial) reconstitution (recomposition, recreation) of a natural peppermint and/or spearmint oil is of interest, for example, because in contrast to the natural substances upon which they are modelled, which are essential oils obtained by steam distillation, such (sensorially) reconstituted, recomposed or recreated oils are not subject to (sensorial) quality variations and their (sensorial) characteristics are not dependent upon the harvest, area of cultivation and/or extraction process.

According to a preferred embodiment of the invention according to the invention, compounds having formula (I) are used to impart, modify and/or strengthen one or more scent or flavour impressions from the group of hay and coumarin, wherein the resulting product (item) containing one or more compounds having formula (I) does not contain the coumarin compound itself and preferably contains no fraction of a natural oil or aroma which itself has a hay-like, coumarin-like note.

Natural peppermint oils which can be (sensorially) reconstituted using one or more compounds having formula (I) are understood to be specifically the essential oils (i.e. obtained by steam distillation) of certain Mentha species, in particular Mentha arvensis (corn mint) and Mentha piperita (peppermint); these include Mentha piperita oils with regional origin denominations of specific areas of cultivation such as Willamette, Yakima and Madras.

Said natural peppermint oils have a hay-like, coumarin-like note which is lacking from the (sensorially) reconstituted, recomposed or recreated peppermint oils known to date. However, the hay-like, coumarin-like note of natural peppermint oils does not come from coumarin, since they contain no coumarin, but presumably from other compounds, some of them not identified, which are present only in traces in peppermint oils.

Natural spearmint oils which can be (sensorially) reconstituted using compounds having formula (I) are understood to be specifically the essential oils of Mentha cardiaca or Mentha spicata. A preferred perfumed or aromatised item according to the invention includes at least one compound having formula (I) which is a compound having formula (III)

(III)

wherein: a first of the radicals R³ or R⁴ denotes methyl and a second of the radicals R³ or R⁴ denotes an alkyl radical having 3 to 6 C atoms, i.e. n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl or 1 ,2,2- trimethylpropyl.

A perfumed or aromatised item according to the invention is preferably selected from the group consisting of: fragrance or aroma composition, preferably peppermint or spearmint aroma composition, food preparation, preferably ready-to-consume or not ready-to-consume foodstuff, oral care preparation and consumable preparation.

The perfumed or aromatised items according to the invention, in particular the preferred items according to the invention from the above group, preferably contain a total amount of the one or more compounds having formula (I) which is sufficient to impart, to modify and/or to strengthen one or more scent or flavour impressions from the group consisting of herbal, hay (like dry grass and slightly sweet), coumarin and fennel, by itself and/or by interaction with the other constituents of the item. The items according to the invention preferably contain no coumarin and no fraction of a natural oil or aroma which itself has a hay-like, coumarin-like note.

L-Menthol has a unique refreshing flavour, a minty scent and a very cooling effect on the skin and mucosa. It is used for example in oral care, in cosmetic and pharmaceutical preparations, in tobacco and in confectionery, as described for example in Perfumer & Flavorist, Vol. 13, October-November 1988, p. 37. L- Menthol is the principal constituent of the peppermint oils obtained from Mentha arvensis (content: around 70 to 80 wt.%) and Mentha piperita (content: around 50 to 60 wt.%).

Within the meaning of the invention, the menthol that is preferably used in items according to the invention can be d-menthol, l-menthol or any mixture thereof, I- menthol, d-menthol and racemic menthol being preferred and l-menthol being particularly preferred, since l-menthol has the aforementioned sensorial characteristics which are very advantageous for the (sensorial) reconstitution of peppermint oils.

Any mixtures of synthetic and natural menthol and of racemic and enantiomer- pure menthol can also be used.

The menthol that is preferably used according to the invention can be of synthetic or natural origin, but the use of synthetic menthol is preferred.

(-)-Carvone is the principal constituent of spearmint oil (content: around 70 to 80 wt.%) and has a herbal, spearmint-like scent and flavour. The (-)-carvone that is preferably used according to the invention can be of synthetic or natural origin.

Menthone and isomenthone (both can be present mutually independently as (+) and/or (-) enantiomers) occur in many essential oils, and in peppermint oils obtained from Mentha species they can even be included in a proportion of over 50 wt. %. Menthone has a characteristic, powerful minty scent and flavour and has a cooling effect; isomenthone is minty, camphor-like and cooling, but slightly duller than menthone.

Within the meaning of the invention, the menthone that is preferably used can be (+)-menthone, (-)-menthone or any mixture thereof, (+)-menthone, (-)-menthone and racemic menthone being preferred and (-)-menthone being particularly preferred, since it is very advantageous for the production of non-natural or synthetic peppermint oils or aromas and for the (sensorial) reconstitution of natural peppermint oils.

Within the meaning of the invention, the isomenthone that is used can be (+)- isomenthone, (-)-isomenthone or any mixture thereof, (+)-isomenthone, (-)- isomenthone and racemic isomenthone being preferred and (+)-isomenthone being particularly preferred, since it is very advantageous for the production of non-natural or synthetic peppermint oils or aromas and for the (sensorial) reconstitution of natural peppermint oils.

It follows from the above that the compounds having formula (I) according to the invention or for use according to the invention are particularly capable of imparting, modifying and/or strengthening the cited scent or flavour impressions if they are present in mixtures with one, several or all compounds selected from the group consisting of (i) menthol, (ii) (-)-carvone, (iii) menthone and (iv) isomenthone. The compounds having formula (I) are thus particularly suitable for being incorporated into fragrance or aroma compositions, preferably peppermint and/or spearmint aroma compositions, and into food, oral care or consumable preparations having peppermint or spearmint scent or flavour notes.

Examples 6 and 7 below illustrate the observed sensorial effects with regard to a herbal/spicy or hay-like or coumarin-like note in mixtures of one or more substances of the group consisting of (i) menthol, (ii) (-)-carvone, (iii) menthone and (iv) isomenthone and compounds having formula (I). The overall olfactory profile of such a blend of fragrances or aroma substances is also rounded out and the fragrance or aroma substance blend is given more vibrancy, roundness, naturalness (authenticity), fullness, complexity and/or staying power.

The total amount of the compounds having formula (I) for use according to the invention in fragrance or aroma compositions according to the invention is preferably 0.001 to 20 wt.%, preferably 0.01 to 20 wt.%, and most particularly preferably 0.1 to 2 wt.%, based on the total amount of fragrance or aroma composition.

Fragrance or aroma compositions according to the invention or food, oral care or consumable preparations (in particular in accordance with one of the embodiments described above as being preferred) are preferred which contain an amount of one or more compounds selected from the group consisting of (i) menthol, (ii) (-)-carvone, (iii) menthone and (iv) isomenthone which is sufficient to produce a dominant peppermint and/or spearmint scent or flavour note in the fragrance or aroma composition or preparation. Such fragrance or aroma compositions or preparations - as stated - preferably contain an amount of compounds having formula (I) which is sufficient to impart, modify and/or strengthen one or more scent or flavour impressions from the group consisting of herbal, hay (like dry grass and slightly sweet), coumarin and fennel. The substance coumarin is preferably not present in such an item according to the invention and such an item preferably likewise contains no natural peppermint or spearmint oil and no natural peppermint or spearmint aroma. In particular, however, at least no fraction of a natural oil or aroma is present which is responsible for the hay-like, coumarin-like note in said natural oils or aromas.

In preferred fragrance or aroma compositions according to the invention the concentrations of the relevant aforementioned constituents are preferably within certain ranges. Particularly preferred are fragrance or aroma compositions according to the invention (preferably according to one of the preferred embodiments given above) containing: (a) one or more compounds having formula (I) as defined above

(preferably in a preferred embodiment), in a total amount in the range from 0.01 to 20 wt.%, preferably 0.1 to 2 wt.%, and (b) (i) menthol, preferably l-menthol, in an amount from 1 to 80 wt.%, preferably 5 to 70 wt.%, and/or

(ii) (-)-carvone in an amount from 1 to 80 wt.%, preferably 5 to 80 wt.%, and/or (iii) menthone, preferably (-)-menthone, and/or

(iv) isomenthone, preferably (+)-isomenthone, in a total amount from 0.5 to 60 wt.%, preferably 1 to 50 wt.%, and preferably (c) menthyl acetate, preferably (-)-menthyl acetate in an amount from 1 to 20 wt.%, preferably 2 to 12 wt.%, particularly preferably 3 to 10 wt.%, wherein the stated quantities are based in each case on the total amount of fragrance or aroma composition.

The proportion of (i) menthol in reconstituted (recombined, recreated) peppermint aromas and peppermint oils is preferably in the range from 30 to 60 wt.%.

The content of (-)-carvone in reconstituted (recombined, recreated) spearmint aromas and spearmint oils is preferably in the range from 30 to 70 wt.%.

The total proportion of menthone and isomenthone is preferably in the range from 0.5 to 60 wt.%, preferably 1 to 50 wt.%, and in reconstituted (recombined, recreated) peppermint aromas and peppermint oils preferably in the range from 5 to 40 wt.%.

The structural formulae of the particularly preferred compounds from group (b) are illustrated below:

(i) l-menthol (ii) (-)-carvone (iii) (-)-menthone (iv) (+)-isomenthone

The structural formula of the (-)-menthyl acetate (l-menthyl acetate) which is particularly preferably used according to the invention as component (c) is reproduced in formula C below.

The preferred component (c) (-)-menthyl acetate (having formula C) has a fresh/fruity, peppermint scent and particularly in reconstituted (recombined, recreated) peppermint aromas and peppermint oils it complements the fragrance and aroma profile.

In food, oral care or consumable preparations according to the invention (as set out above) too, certain concentrations of compounds having formula (I) or of the fragrance or aroma compositions according to the invention are preferred. Particularly preferred are preparations according to the invention consisting of a fragrance or aroma composition according to the invention (preferably with a proportion specified above as being preferred of the compound(s) having formula (I)) in an amount from 0.05 to 50 wt.%, preferably in the range from 0.05 to 6 wt. %, by preference in the range from 0.1 to 3 wt.%, based on the total weight of the preparation.

The aforementioned concentrations for preparations according to the invention relate in particular to ready-to-use preparations, i.e. preparations which can be used directly by the end consumer. Ready-to-use applies in particular to ready-to- consume foodstuffs, such as e.g. ready-to-consume confectionery products or ready-to-consume drinks. Ready-to-use also applies however to oral care products (oral hygiene products), which can be used directly by the consumer.

In ready-to-use preparations, in particular in confectionery products (such as chewing gums and boiled sweets) or in oral hygiene products (such as toothpastes, tooth creams and gels), the proportion of a fragrance or aroma composition according to the invention containing one or more compounds having formula (I) is preferably in the range from 0.05 to 6 wt.%, by preference in the range from 0.1 to 3 wt.%, based on the total weight of the ready-to-use preparation.

In ready-to-consume alcoholic or non-alcoholic drinks within the meaning of the invention, the proportion of a fragrance or aroma composition according to the invention containing one or more compounds having formula (I) is preferably in the range from 3 to 100 ppm, by preference in the range from 5 to 50 ppm, based on the total weight of the ready-to-consume preparation.

If, however, the ready-to-use preparation is a capsule suitable for direct consumption (see example F10 below), the proportion of the fragrance or aroma composition for use within the meaning of the invention containing compounds having formula (I) can be significantly higher and can be up to 50 wt.%. The food, oral care or consumable preparations according to the invention are generally products which are designed to be introduced into the human oral cavity, to remain there for a certain time and then either to be swallowed (i.e. ready-to-consume foodstuffs) or to be removed from the oral cavity again (e.g. chewing gums or toothpaste). It goes without saying that the use of compounds having formula (I) or of fragrance or aroma compositions according to the invention is intended for any type of such products. These products include all substances or products which are designed to be consumed by a person in the processed, semi-processed or unprocessed state. This also includes all substances which are added to foodstuffs during their production, processing or finishing and which are intended to be introduced into the human oral cavity.

It goes without saying that the compounds having formula (I) and the fragrance or aroma compositions according to the invention can be used in particular in foodstuffs. Within the meaning of the present text, a "foodstuff' is understood to refer in particular to substances which are intended to be swallowed and then digested by a person in an unchanged, prepared or processed state; the term foodstuff thus also covers shells, coatings or other enclosures which are intended to be swallowed at the same time or for which swallowing is anticipated. Certain products which are conventionally removed again from the oral cavity (e.g. chewing gums) are also understood to be foodstuffs within the context of the present text, since the possibility of at least a part of them being swallowed cannot be excluded.

In particular, one or more compounds having formula (I) or a fragrance or aroma composition according to the invention are used in ready-to-consume foodstuffs. A ready-to-consume foodstuff is understood to be a foodstuff which is already fully constituted in terms of the substances that are critical to its flavour. The term "ready-to-consume foodstuff" also includes drinks and solid or semi-solid ready- to-consume foodstuffs. Examples include frozen products which have to be thawed and heated to eating temperature before being consumed. Products such as yoghurt or ice cream as well as chewing gums and hard-boiled sweets are also classed as ready-to-consume foods. The compounds having formula (I) and fragrance or aroma compositions according to the invention can also be used semi-finished foodstuffs. The term semi-finished foodstuffs relates here to foodstuffs which are designed to be consumed only after further processing, after addition of aromas or flavourings which determine or help to determine the sensorial impression.

An oral care product (also known as oral hygiene product or oral hygiene preparation) within the meaning of the invention is understood to be one of the formulations familiar to the person skilled in the art for cleansing and care of the oral cavity and pharynx and for freshening the breath. This expressly includes care of the teeth and gums. Pharmaceutical forms of common oral hygiene formulations are creams, gels, pastes, foams, emulsions, suspensions, aerosols, sprays and also capsules, granules, pastilles, tablets, sweets or chewing gums, although this list should not be understood as being limiting for the purposes of this invention.

Preferred ready-to-consume alcoholic or non-alcoholic drinks within the meaning of the invention are (preferably carbonic acid-free) non-alcoholic soft drinks or alcoholic liqueurs.

In a ready-to-consume non-alcoholic drink within the meaning of the invention, the proportion of a fragrance or aroma composition according to the invention containing one or more compounds having formula (I) is preferably in the range from 3 to 30 ppm (corresponding to around 0.3 to 3 g per 100 litres of drink), preferably in the range from 5 to 15 ppm (corresponding to around 0.5 to 1.5 g per 100 litres of drink), based on the total weight of the ready-to-consume preparation. Ready-to-consume non-alcoholic drinks within the meaning of the invention preferably have a sugar content (sucrose content) or a glucose syrup content in the range from 8 to 15 wt.%, preferably in the range from 9 to 13 wt.%, based on the ready-to-consume non-alcoholic drink.

In a ready-to-consume alcoholic drink within the meaning of the invention, the proportion of a fragrance or aroma composition according to the invention containing one or more compounds having formula (I) is preferably in the range from 10 to 100 ppm (corresponding to around 1 to 10 g per 100 litres of drink), preferably in the range from 25 to 80 ppm (corresponding to around 2.5 to 8 g per 100 litres of drink), based on the total weight of the ready-to-consume preparation. Ready-to-consume drinks within the meaning of the invention are preferably liqueurs and preferably have a sugar content (sucrose content) or a glucose syrup content in the range from 10 to 25 wt.%, preferably in the range from 15 to 20 wt.%, based on the ready-to-consume alcoholic drink. The alcohol content is preferably in the range from 12 to 25 vol.%, preferably in the range from 15 to 20 vol.%, based on the ready-to-consume alcoholic drink.

A preferred ready-to-use preparation according to the invention is (A) a ready-to- consume sugar-free, reduced-sugar or sugar-containing confectionery product, in particular in the form of chocolate, filled chocolate (filled for example with an aromatised fondant mass, e.g. of the After Eight type), chocolate bar product, fruit gum, hard-boiled or soft sweet, chewy sweet, sugar pearl, lollipop, capsule (preferably seamless capsule, preferably for direct consumption, preferably with a shell based on gelatine or alginate), chewing gum (e.g. in the form of strips, tablets, pellets, dragees, balls, hollow balls), (B) an oral care product (oral hygiene product), in particular in the form of toothpaste, tooth cream, tooth gel, tooth powder, liquid tooth cleaner, foam tooth cleaner, mouthwash, tooth cream and mouthwash as a 2-in-1 product, lozenge, mouth spray, dental floss or dental chewing gum, or (C) an alcoholic or non-alcoholic drink.

The terms "food preparation" or "consumable preparation" also cover the ready- to-use products and foodstuffs (ready-to-consume or semi-finished foodstuff) defined above. It goes without saying that the terms used in the present text for certain groups of items and preparations include some products which can come under several categories. Thus, for example, food preparations can also be consumable preparations, in particular foodstuffs. Common to all the terms, however, is the fact that they relate to items (products) which are designed to be introduced into the human oral cavity and there to induce a scent or flavour impression. In fragrance and/or aroma compositions according to the invention which contain (a) one or more compounds having formula (I) and (b) one, several or all compounds selected from the group consisting of (i) menthol, (ii) (-)-carvone, (iii) menthone, (iv) isomenthone, the compounds having formula (I) for use according to the invention are capable even in small amounts of rounding out the overall olfactory or gustatory profile of the fragrance or aroma composition and in particular of imparting more vibrancy, roundness, naturalness (authenticity), fullness, complexity and/or staying power to the composition.

In the case of a reconstituted (recombined, recreated) i.e. non-natural peppermint oil (which contains significant amounts of menthol) or spearmint oil (which contains significant amounts of (-)-carvone), the addition of one or more compounds having formula (I), in particular in the aforementioned amounts, significantly increases the vibrancy, roundness, naturalness (authenticity), fullness, complexity and/or staying power, in particular because of the olfactory and gustatory notes imparted by the compounds having formula (I) which notes are likewise present at least in part in natural peppermint oil and spearmint oil.

To summarise, the following fragrance or aroma compositions (blends) according to the invention thus have a surprising olfactory and/or gustatory quality:

- Fragrance or aroma blends (= compositions) containing one or more compounds having formula (I) and one or more further fragrances or aroma substances, (in such compositions one, several or all scent or flavour impressions from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage are imparted, modified and/or strengthened by the compound(s) having formula (I))

Fragrance or aroma blends (= compositions) containing one or more compounds having formula (I) and one, several or all compounds from group (b)

(i) menthol and/or (ii) (-)-carvone and/or (iii) menthone and/or (iv) isomenthone and one or more further fragrances or aroma substances; (the use is preferred here, however, of compounds having formula (I) which impart a scent or flavour impression from the group consisting of herbal, hay (like dry grass and slightly sweet) and coumarin and preferably no sensorial impression from the group consisting of spicy, celery and lovage).

It should also be noted that in particular fragrance or aroma compositions and corresponding items containing

(a) one or more compounds having formula (I),

(b) (i) l-menthol and/or (ii) (-)-carvone

and optionally

(c) menthyl acetate

are most particularly preferred, because such combinations represent an excellent basis for the production of reconstituted, i.e. non-natural, peppermint and spearmint aromas along with peppermint oils and spearmint oils.

If the compounds having formula (I) for use according to the invention are used in combination with one (i.e. a single one of the compounds (i), (ii), (iii) or (iv) listed below), several or all compounds selected from the group consisting of (i) menthol, (ii) (-)-carvone, (iii) menthone and (iv) isomenthone, the compounds for use according to the invention, depending on the concentration in which they are used, induce a multi-faceted scent and flavour impression. It has already been mentioned that the use of compounds having formula (I) is preferred for combination with one or more of the compounds (i), (ii), (iii) and (iv) which impart one or more scent or flavour impressions from the group consisting of herbal, hay and coumarin.

Perfumed or aromatised items according to the invention include one or more compounds having formula (I), preferably in the form of a fragrance or aroma composition according to the invention. The sensorial characteristics, material characteristics, such as solubility in common solvents, and the compatibility with other common constituents of such products underline the particular suitability of compounds having formula (I) for the cited applications.

The present invention also concerns a process for imparting, modifying and/or strengthening one or more scent and flavour impressions consisting of the group comprising herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage, wherein one or more compounds having formula (I) as defined above, preferably a compound having formula (I) described above as preferred and/or not yet known from the prior art, or - a fragrance or aroma composition (preferably a fragrance or aroma composition according to the invention) containing one or more compounds having formula (I) as defined above (particularly preferably a compound having formula (I) described above as preferred and/or one that is novel) is brought into contact with or mixed with a product.

The present invention also concerns a process for producing a fragrance or aroma composition (preferably according to the invention) with the following step:

Mixing one or more compounds having formula (I) as defined above, preferably one or more compounds having formula (I) which are not yet known from the prior art (cf. in this respect the comments below regarding novel compounds having formula (I)) with conventional constituents of a fragrance or aroma composition, wherein the one or more compounds having formula (I) are used in an amount which is sufficient to impart, modify and/or strengthen in the fragrance or aroma composition one or more scent or flavour impressions from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage. Compounds having formula (I) are particularly preferably used which impart one or more scent or flavour impressions from the group consisting of herbal, hay and coumarin if the fragrance or aroma composition is to be a peppermint and/or spearmint composition. Herbal/spicy scent notes are used by contrast in a wide range of perfume compositions, for example in woody/spicy men's fragrances (= masculine scents).

The process according to the invention is preferably one for producing a fragrance or aroma composition as defined above (and/or in the appended claims). In preferred processes according to the invention (a) one or more compounds having formula (I) as defined above and/or in the claims is mixed with (b) one, several or all compounds selected from the group consisting of

(i) menthol,

(ii) (-)-carvone

(iii) menthone and (iv) isomenthone, and preferably (c) menthyl acetate.

Owing to their olfactory characteristics, the compounds having formula (I) for use according to the invention are ideally suited for use in fragrance and aroma compositions. The compounds can be used (i) as an individual substance or (ii) combined with a multiplicity of other fragrances or aroma substances in a large number of products. The compounds can be particularly advantageously combined with other fragrances or aroma substances in varying, different proportions to form novel fragrance or aroma compositions.

The compounds having formula (I) for use according to the invention can be produced in various ways, those that are preferred being illustrated by way of example by the skeletal formulae below:

R⁴-Li

R³-Li

Production takes place for example in accordance with the top skeletal formula by orf/7o-metallisation of a disubstituted furan (a first radical R¹, R², R³ denotes hydrogen, a second and third radical R¹, R², R³ mutually independently preferably denote an alkyl or alkenyl radical) with a lithium organyl R-Li (in R-Li R preferably denotes alkyl, aryl) and subsequent alkylation with an alkyl halide R⁴-X (in R⁴-X R⁴ preferably denotes alkyl, alkenyl, X = Cl, Br, I; but also O-tosylate, O-mesylate or similar leaving groups). In example 11 (below), for example, 2-pentyl-3,5- dimethylfuran is obtained in this way from 2-pentyl-3-methylfuran by alkylation with methyl iodide, while in examples 1 i - 1 k (below), 2,3-dimethyl-5-alkylfurans are obtained from 2,3-dimethylfuran by alkylation with the corresponding alkyl bromides. n-Butyl lithium is used in all examples (below) for orffro-metallisation.

Alternatively, production can take place in accordance with the middle skeletal formula, for example, by adding Grignard reagents R⁴-MgX (in R⁴-MgX R⁴ preferably denotes alkyl or alkenyl and X = Cl, Br or I) or lithium organyls R⁴-Li (in R⁴-Li R⁴ denotes alkyl, alkenyl) to disubstituted 5H-furan-2-ones (a first radical R¹, R², R³ denotes hydrogen, a second and third radical R¹, R², R³ mutually independently denote an alkyl or alkenyl radical) and elimination of water with formation of the aromatic furan skeleton. In examples 1 b-1 h (below) 3,4-dimethyl- 2-alkylfurans are produced in this way by adding the corresponding alkyl magnesium bromides to 3,4-dimethyl-2(5H)-furanone.

As a further alternative, production can take place in accordance with the bottom skeletal formula, for example, by adding Grignard reagents R³-MgX (in R³-MgX R³ preferably denotes alkyl or alkenyl and X = Cl, Br or I) or lithium organyls R³-Li (in R³-Li R³ preferably denotes alkyl, alkenyl) to disubstituted 2H-furan-3-ones (a first radical R¹, R², R⁴ denotes hydrogen, a second and third radical R¹, R², R⁴ preferably mutually independently denote an alkyl or alkenyl radical) and elimination of water with formation of the aromatic furan skeleton. In example 1 m (below), 2,5-dimethyl-3-pentylfuran is produced in this way by adding pentyl magnesium bromide to 2,5-dimethyl-3(2H)-furanone.

Ingredients with which the compounds having formula (I) (in one of the cited forms) can be combined are, for example: preservatives, abrasives, anti-acne agents, anti-skin-ageing agents, antibacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, irritation-preventing agents, irritation-inhibiting agents, antimicrobial agents, antioxidants, astringents, perspiration-inhibiting agents, antiseptic agents, antistatics, binders, buffers, carriers, chelating agents, cell stimulants, cleansing agents, conditioning agents, depilatory agents, surface-active substances, deodorising agents, antiperspirants, softeners, emulsifiers, enzymes, essential oils, fibres, film formers, fixatives, foaming agents, foam stabilisers, substances to prevent foaming, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair sculpting agents, hair smoothing agents, moisture-releasing agents, moisturising substances, moisture-retaining substances, bleaching agents, strengthening agents, stain removal agents, optical brightening agents, impregnating agents, dirt repellent agents, friction-reducing agents, lubricants, moisture creams, ointments, opacifiers, plasticising agents, concealing agents, polishes, glossing agents, polymers, powders, proteins, nourishing agents, abrading agents, silicones, skin calming agents, skin cleansing agents, skin conditioning agents, skin healing agents, skin lightening agents, skin protecting agents, skin softening agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilisers, UV-absorbing agents, UV filters, detergents, fabric softeners, suspending agents, skin tanning agents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, colour-protecting agents, pigments, anti-corrosives, aromas, flavourings, fragrances, polyols, surfactants, electrolytes, organic solvents or silicone derivatives.

Individual cooling agents preferred for use in the context of the present invention for incorporation into fragrance and aroma compositions or items according to the invention are listed below. The person skilled in the art can extend the following list by a multiplicity of further cooling agents; the listed cooling agents can also be used in combination with one another: menthone glycerol acetal (trade name: Frescolat^®MGA), menthyl lactate (trade name: Frescolat^®ML, the menthyl lactate is preferably l-menthyl lactate, in particular l-menthyl-l-lactate), substituted menthyl-3-carboxylic acid amides (e.g. menthyl-3-carboxylic acid-N-ethylamide, also known as WS-3), 2-isopropyl-N-2,3-trimethyl butanamide (also known as WS-23), substituted cyclohexane carboxylic acid amides, 3-menthoxypropane- 1 ,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, N-acetyl glycine menthyl ester, isopulegol, menthyl hydroxycarboxylic acid esters (e.g. menthyl-3-hydroxybutyrate), monomenthyl succinate, 2-mercapto- cyclodecanone, menthyl-2-pyrrolidin-5-one carboxylate, 2,3-dihydroxy-p- menthane, 3,3,5-trimethyl cyclohexanone glycerol ketal, 3-menthyl-3,6-di- and -trioxaalkanoates, 3-menthyl methoxyacetate, icilin.

Particularly preferred cooling agents are: menthone glycerol acetal (trade name: Frescolat^®MGA), menthyl lactate (preferably l-menthyl lactate, in particular I- menthyl-l-lactate, trade name: Frescolat^®ML), substituted menthyl-3-carboxylic acid amides (e.g. menthyl-3-carboxylic acid-N-ethylamide), 2-isopropyl-N-2,3- trimethyl butanamide, 3-menthoxypropane-1 ,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, isopulegol and monomenthyl succinate.

It is advantageous to combine the compounds having formula (I) according to the invention or for use according to the invention with at least one further fragrance or aroma substance and thus to form a novel fragrance or aroma composition. Particularly interesting and natural, novel and original fragrance notes can be created in this way. Fragrances which are advantageously suitable for combining can be found for example in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N. J. 1969, self-published, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001. The following specific examples can be cited:

Extracts of natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, such as, for example,

ambergris tincture; amyris oil; angelica seed oil; angelica root oil; aniseed oil; valerian oil; basil oil; treemoss absolute; bay oil; mugwort oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil; calamus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil; cassia oil; cassie absolute; castoreum absolute; cedar leaf oil; cedarwood oil; cistus oil; citronella oil; lemon oil; copaiba balsam; copaiba balsam oil; coriander oil; costus root oil; cumin oil; cypress oil; davana oil; dill weed oil; dill seed oil; eau de brouts absolute; oakmoss absolute; elemi oil; tarragon oil; eucalyptus citriodora oil; eucalyptus oil; fennel oil; spruce needle oil; galbanum oil; galbanum resin; geranium oil; grapefruit oil; guaiac wood oil; gurjun balsam; gurjun balsam oil; helichrysum absolute; helichrysum oil; ginger oil; iris root absolute; iris root oil; jasmine absolute; calamus oil; camomile blue oil; camomile Roman oil; carrot seed oil; cascarilla oil; pine needle oil; spearmint oil; caraway oil; labdanum oil; labdanum absolute; labdanum resin; lavandin absolute; lavandin oil; lavender absolute; lavender oil; lemongrass oil; lovage oil; distilled lime oil; pressed lime oil; linaloe oil; litsea cubeba oil; bayleaf oil; mace oil; marjoram oil; mandarin oil; massoi bark oil; mimosa absolute; musk seed oil; musk tincture; clary sage oil; nutmeg oil; myrrh absolute; myrrh oil; myrtle oil; clove leaf oil; clove flower oil; neroli oil; olibanum absolute; olibanum oil; opopanax oil; orange flower absolute; orange oil; origanum oil; palmarosa oil; patchouli oil; perilla oil; Peru balsam oil; parsley leaf oil; parsley seed oil; petitgrain oil; peppermint oil; pepper oil; pimento oil; pine oil; pennyroyal oil; rose absolute; rosewood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; spike lavender oil; star anise oil; styrax oil; tagetes oil; fir needle oil; tea-tree oil; turpentine oil; thyme oil; tolu balsam; tonka absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; cognac oil; wormwood oil; wintergreen oil; ylang-ylang oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;

individual fragrances from the group of hydrocarbons, such as, for example, 3- carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E₁Z)-1 , 3, 5-undecatriene; styrene; diphenyl methane;

aliphatic alcohols, such as, for example, hexanol; octanol; 3-octanol; 2,6- dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenol; 1 -octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methylene heptan-2-ol; (E,Z)-2,6-nonadienol; 3,7- dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

aliphatic aldehydes and acetals thereof, such as, for example, hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2- methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5-heptenal; 10- undecenal; (E)-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10- trimethyl-5,9-undecadienal; heptanal diethyl acetal; 1 ,1-dimethoxy-2,2,5- trimethyl-4-hexene; citronellyl oxyacetaldehyde; 1-(1 -methoxypropoxy)-(E/Z)-3- hexene; aliphatic ketones and oximes thereof, such as, for example, 2-heptanone; 2- octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3- heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

aliphatic sulfur-containing compounds, such as, for example, 3- methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3- mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1 - menthene-8-thiol;

aliphatic nitriles, such as, for example, 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6- octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile;

esters of aliphatic carboxylic acids, such as, for example, (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3- hexenyl acetate; octyl acetate; 3-octyl acetate; 1 -octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E)- and (Z)-3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl-2-methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl-(E,Z)-2,4-decadienoate; methyl-2-octynoate; methyl-2-nonynoate; allyl-2- isoamyloxyacetate; methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

acyclic terpene alcohols, such as, for example, citronellol; geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl- 7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6- dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6- octadien-3-ol; 3,7-dimethyl-1 ,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien-1 -ol; and formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoat.es thereof; acyclic terpene aldehydes and ketones, such as, for example, geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10- trimethyl-9-undecenal; geranylacetone; and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;

cyclic terpene alcohols, such as, for example, menthol; isopulegol; alpha- terpineol; terpinenol-4; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guaiol; and formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoat.es thereof;

cyclic terpene aldehydes and ketones, such as, for example, menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; alpha- ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha- isomethylionone; beta-isomethylionone; alpha-irone; alpha-damascone; beta- damascone; beta-damascenone; delta-damascone; gamma-damascone; 1 - (2,4,4-trimethyl-2-cyclohexen-1 -yl)-2-buten-1 -one; 1 ,3,4,6,7,8a-hexahydro-

1 ,1 ,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one; 2-methyl-4-(2,6,6- trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8- megastigmatrien-3-one; alpha-sinensal; beta-sinensal; acetylated cedarwood oil (methyl cedryl ketone);

cyclic alcohols, such as, for example, 4-tert-butylcyclohexanol; 3,3,5- trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9- cyclododecatrien-1 -ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

cycloaliphatic alcohols, such as, for example, alpha-3,3-trimethyl cyclohexylmethanol; 1 -(4-isopropylcyclohexyl)ethanol; 2-methyl-4-(2,2,3- trimethyl-3-cyclopent-1-yl)butanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2- buten-1-ol; 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-methyl-5-(2,2,3-trimethyl-3- cyclopent-1 -yl)-4-penten-2-ol; 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1 -yl)-4- penten-2-ol; 1 -(2,2,6-trimethylcyclohexyl)pentan-3-ol; 1 -(2,2,6- trimethylcyclohexyl)hexan-3-ol;

cyclic and cycloaliphatic ethers, such as, for example, cineol; cedryl methyl ether; cyclododecyl methyl ether; 1 ,1-dimethoxycyclododecane;

(ethoxymethoxy)cyclododecane; alpha-cedrene epoxide; 3a, 6, 6,9a- tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a- trimethyldodecahydronaphtho[2,1-b]furan; 1 ,5,9-trimethyl-13- oxabicyclo[10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1- yl)-5-methyl-5-(1 -methyl propyl)-1 ,3-dioxane;

cyclic and macrocyclic ketones, such as, for example, 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2- pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1 -one; 3-methyl-cis-2- penten-i-yl-2-cyclopenten-i-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3- methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3- methylcyclopentadecanone; 4-(1 -ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1 ,1 ,2,3,3- pentamethyl-4(5H)-indanone; 8-cyclohexadecen-1 -one; 9-cycloheptadecen-1 - one; cyclopentadecanone; cyclohexadecanone;

cycloaliphatic aldehydes, such as, for example, 2,4-dimethyl-3- cyclohexenecarbaldehyde; 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten- 1 -ylJ-S-cyclohexenecarbaldehyde;

cycloaliphatic ketones, such as, for example, 1-(3,3-dimethylcyclohexyl)-4- penten-1 -one; 2,2-dimethyl-1 -(2,4-dimethyl-3-cyclohexen-1 -yl)-1 -propanone; 1 - (5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one; 2,3,8,8-tetramethyl- 1 ,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; methyl-2,6,10-trimethyl- 2,5,9-cyclododecatrienyl ketone; tert-butyl-(2,4-dimethyl-3-cyclohexen-1 -yl) ketone; esters of cyclic alcohols such as, for example, 2-tert-butylcyclohexyl acetate; 4- tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert- pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2- naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H- pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7- methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate; 4,7-methano- 3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate; 4,7-methano-3a,4,5,6,7,7a- hexahydro-5 or 6-indenyl isobutyrate; 4,7-methanooctahydro-5 or 6-indenyl acetate;

esters of cycloaliphatic alcohols such as, for example, 1-cyclohexylethyl crotonate;

esters of cycloaliphatic carboxylic acids, such as, for example, allyl-3-cyclohexyl propionate; allyl cyclohexyloxyacetate; cis- and trans-methyl dihydrojasmonate; cis- and trans-methyl jasmonate; methyl^-hexyl-S-oxocyclopentanecarboxylate; ethyl^-ethyl-θ.θ-dimethyl^-cyclohexenecarboxylate; ethyl-2,3,6,6-tetramethyl-2- cyclohexenecarboxylate; ethyl-2-methyl-1 ,3-dioxolane-2-acetate;

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

esters of araliphatic alcohols and aliphatic carboxylic acids, such as, for example, benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2- phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2- phenylethyl isovalerate; 1 -phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha- dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4- methoxybenzyl acetate; araliphatic ethers, such as, for example, 2-phenylethyl methyl ether; 2- phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1 ,3-dioxane; 4,4a,5,9b-tetrahydroindeno[1 ,2-d]-m-dioxin; 4,4a,5,9b-tetrahydro-2,4- dimethylindeno[1 ,2-d]-m-dioxin;

aromatic and araliphatic aldehydes, such as, for example, benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydratropaldehyde; 4- methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2- dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-tert- butylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert- butylphenyl)propanal; cinnamaldehyde; alpha-butylcinnamaldehyde; alpha- amylcinnamaldehyde; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3- ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4- dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4- methylenedioxyphenyl)propanal;

aromatic and araliphatic ketones, such as, for example, acetophenone; 4- methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6- dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)ethanone; 2-benzofuranyl ethanone; (3-methyl-2- benzofuranyl)ethanone; benzophenone; 1 ,1 ,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1 ,1 -dimethyl-4-indanyl methyl ketone; 1 -[2,3-dihydro-1 ,1 ,2,6- tetramethyl-3-(1 -methylethyl)-1 H-5-indenyl]ethanone; 5',6',7',8'-tetrahydro-

3',5',5',6',8',8'-hexamethyl-2-acetonaphthone;

aromatic and araliphatic carboxylic acids and esters thereof, such as, for example, benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl-2,4-dihydroxy-3,6-dimethylbenzoate; ethyl-3-phenylglycidate; ethyl-3- methyl-3-phenylglycidate;

nitrogen-containing aromatic compounds, such as, for example, 2,4,6-trinitro-1 ,3- dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamonitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenyl pentanoic acid nitrile; methyl anthranilate; methyl-N-methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal; 2-methyl-3-(4- tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6- isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2-(3- phenylpropyl)pyridine; indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl- 3-methoxypyrazine;

phenols, phenyl ethers and phenyl esters, such as, for example, estragole; anethole; eugenol; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1 ,4-dimethoxybenzene; eugenyl acetate; 2- methoxy-4-methylphenol; 2-ethoxy-5-(1 -propenyl)phenol; p-cresyl phenylacetate;

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

lactones, such as, for example, 1 ,4 -octanolide; 3-methyl-1 ,4-octanolide; 1 ,4- nonanolide; 1 ,4-decanolide; 8-decen-1 ,4-olide; 1 ,4-undecanolide; 1 ,4- dodecanolide; 1 ,5-decanolide; 1 ,5-dodecanolide; 4-methyl-1 ,4-decanolide; 1 ,15- pentadecanolide; cis- and trans-11-pentadecen-1 ,15-olide; cis- and trans-12- pentadecen-1 ,15-olide; 1 ,16-hexadecanolide; 9-hexadecen-1 ,16-olide; 10-oxa- 1 ,16-hexadecanolide; 11 -oxa-1 ,16-hexadecanolide; 12-oxa-1 ,16-hexadecanolide; ethylene-1 ,12-dodecanedioate; ethylene-1 ,13-tridecanedioate; coumarin; 2,3- dihydrocoumarin; octahydrocoumarin. Fragrance or aroma compositions containing the compounds having formula (I) for use according to the invention can be used in liquid form, undiluted or diluted with a solvent, for perfuming or aromatising. Suitable solvents for this purpose are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, etc.

Fragrance or aroma compositions according to the invention containing one or more compounds having formula (I) can also be adsorbed on a carrier, which ensures both a fine distribution of the fragrances or aroma substances in the product and a controlled release during use. Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsums, clays, clay granules, gas concrete, etc., or organic materials such as woods, cellulose-based substances, sugars, dextrins (e.g. maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes. The combination of composition according to the invention and carrier makes an exemplary item according to the invention.

Fragrance or aroma compositions containing one or more compounds having formula (I) can also be used in microencapsulated or spray-dried form, in the form of inclusion complexes or extrusion products (i.e. items according to the invention) and added in this form to a product to be perfumed or aromatised, for example.

The properties of the compositions modified in such a way can optionally be further optimised by coating with suitable materials with a view to a more selective fragrance release, waxy plastics such as e.g. polyvinyl alcohol being preferably used. The resulting products likewise represent items according to the invention.

Microencapsulation of the fragrance or aroma compositions according to the invention to form items according to the invention can take place by means of the so-called coacervation process, for example, using capsule materials made from polyurethane-like substances or soft gelatine, for example. The spray-dried fragrance or aroma compositions can be prepared by spray drying an emulsion or dispersion containing the fragrance or aroma composition, for example, wherein modified starches, proteins, dextrin and vegetable gums can be used as carriers. Inclusion complexes can be prepared by, for example, introducing dispersions of the fragrance or aroma composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. water. Extrusion products can be obtained by melting the fragrance or aroma compositions with a suitable waxy substance and by extrusion with subsequent solidification, optionally in a suitable solvent, e.g. isopropanol.

The compounds having formula (I) and fragrance compositions containing one or more compounds having formula (I) can be used in concentrated form, in solutions or in the aforementioned modified form for the production of perfumed items according to the invention such as e.g. perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, preshave products, splash colognes and perfumed refreshing wipes, and for the perfuming of acid, alkaline and neutral cleaning agents, such as e.g. floor cleaners, window cleaners, washing-up liquids, bath and sanitary cleaners, scouring agent, solid and liquid WC cleaners, powdered and foaming carpet cleaners, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents such as bleaches, soaking agents and stain removers, fabric softeners, laundry soaps, detergent tablets, disinfectants, surface disinfectants and air fresheners in liquid or gel form or applied to a solid support, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe creams and personal care products such as e.g. solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water, water-in-oil and water-in- oil-in-water type, such as e.g. skin creams and lotions, face creams and lotions, sun creams and lotions, aftersun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, haircare products such as e.g. hair sprays, hair gels, hair setting lotions, hair rinses, permanent and semi-permanent hair colorants, hair sculpting agents such as cold waves and hair smoothing agents, hair waters, hair creams and lotions, deodorants and antiperspirants such as e.g. underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetic products such as e.g. eyeshadows, nail polishes, foundations, lipsticks, mascara, and of candles, lamp oils, incense sticks, insecticides, repellents and fuels.

The compounds having formula (I) can be incorporated into aromatised items or items to be aromatised, in particular food, oral care or consumable preparations.

Food or consumable preparations are, for example, baked goods (e.g. bread, dry biscuits, cakes, other pastries), confectionery (e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard-boiled and soft sweets, chewing gum), alcoholic or non-alcoholic drinks (e.g. coffee, tea, wine, wine-based drinks, beer, beer-based drinks, liqueurs, spirits, brandies, fruit-based soft drinks, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (e.g. instant chocolate drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, cured or uncured sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, muesli bars, pre-fermented prepared rice products), dairy products (e.g. milk drinks, ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed milk protein-containing products), products made from soya protein or other soya bean fractions (e.g. soya milk and products made therefrom, preparations containing soya lecithin, fermented products such as tofu or tempe or products made therefrom, soy sauces), fruit preparations (e.g. jams, fruit sorbets, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-fermented vegetables, pickled vegetables, preserved vegetables), snacks (e.g. baked or fried potato crisps or potato dough products, bread dough products, extruded products based on maize or peanuts), products based on fats and oils or emulsions thereof (e.g. mayonnaise, remoulade, dressings, spice preparations), other ready meals and soups (e.g. dried soups, instant soups, pre-fermented soups), spices, spice mixes and in particular seasonings, which are used in the snacks sector for example. After incorporation of the compound according to the invention these preparations are preparations according to the invention (as an example of items according to the invention).

Preferred products suitable for consumption are for example baked goods (biscuits, cakes, muffins, waffles, cake mixes), confectionery (hard-boiled sweets, soft sweets, chewy sweets, tablets, pastilles, sugar pearls, sugar fillings), dairy products (yoghurts, custards, ice cream), chocolate products (white, milk or dark chocolate, chocolate bars), fat masses (fillings for baked goods such as e.g. biscuit fillings, fatty chocolate fillings, fatty chocolate bar fillings), chewing gums (sugar-free, sugar-containing, sticks, tablets, dragees), snacks and snack mixes, water-soluble powder products, toppings, cf. also the comments above on preferred (ready-to-use) preparations according to the invention.

Preparations according to the invention can also take the form of a semi-finished product or a spice mix.

Preparations according to the invention can be used in particular as semi-finished products for the production of other food or consumable preparations, in particular in spray-dried form. Preparations according to the invention can also take the form of capsules, tablets (uncoated and coated tablets, e.g. stomach acid-resistant coatings), pastilles, granules, pellets, solids mixtures, dispersions in liquid phases, emulsions, powders, solutions, pastes or other swallowable or chewable preparations as food supplements.

Oral care preparations according to the invention are in particular oral and/or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral care products.

Other conventional active ingredients, basic substances, auxiliary substances and additives for food, oral care or consumable preparations according to the invention can be included in quantities of 5 to 99.99 wt.%, preferably 10 to 80 wt. %, based on the total weight of the preparation. The preparations can also contain water in a quantity of up to 99.5 wt.%, preferably 5 to 80 wt.%, based on the total weight of the preparation.

The preparations according to the invention (as examples of items according to the invention) containing one or more compounds having formula (I) are produced according to a preferred embodiment by incorporating one or more compounds having formula (I) without solvent, as a solution (e.g. in ethanol, water or 1 ,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (e.g. maltodextrin, starch, silica gel), other aromas or aroma substances and optionally other auxiliary substances and/or stabilisers (e.g. natural or synthetic polysaccharides and/or vegetable gums such as modified starches or gum arabic) into a basic food, oral care or consumable preparation. Preparations according to the invention in the form of a solution and/or suspension or emulsion can advantageously also be converted to a solid preparation according to the invention (semi-finished product) by spray drying.

As semi-finished products, the spray-dried solid preparations according to the invention (as an example of items according to the invention) are particularly suitable for the production of further preparations according to the invention. The spray-dried solid preparations according to the invention preferably contain 50 to 95 wt.% of carriers, in particular maltodextrin and/or starch, 5 to 40% of auxiliary substances, preferably natural or synthetic polysaccharides and/or vegetable gums such as modified starches or gum arabic.

According to a further preferred embodiment, one or more compounds having formula (I) and optionally other constituents of the preparation according to the invention are first incorporated into emulsions, liposomes, e.g. starting from phosphatidyl cholin, microspheres, nanospheres or into capsules, granules or extruded products from a suitable matrix for foodstuffs and consumable products, e.g. from starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g. dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan), natural fats, natural waxes (e.g. beeswax, carnauba wax) from proteins, e.g. gelatine, or other natural products (e.g. shellac) to produce preparations according to the invention. Depending on the matrix, the products can be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally a suitable combination of the above processes. In a further preferred production process for a preparation according to the invention, one or more compounds having formula (I) are first complexed with one or more suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably α- or β-cyclodextrin, and used in this complexed form.

A preparation according to the invention is particularly preferred wherein the matrix is chosen such that the compounds having formula (I) undergo a delayed release from the matrix, such that a lasting effect is achieved. A fat, wax, polysaccharide or protein matrix is particularly preferred in this respect.

As other constituents for food or consumable preparations according to the invention, conventional basic substances, auxiliary substances and additives for foodstuffs or consumables can be used, e.g. water, mixtures of fresh or processed, plant-based or animal-based basic substances or raw materials (e.g. raw, roast, dried, fermented, smoked and/or boiled meat, bone, gristle, fish, vegetables, fruit, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrin, amylose, amylopectin, inulin, xylan, cellulose, tagatose), sugar alcohols (e.g. sorbitol, erythritol), natural or hydrogenated fats (e.g. tallow, lard, palm oil, coconut butter, hydrogenated vegetable fat), oils (e.g. sunflower oil, groundnut oil, maize oil, olive oil, fish oil, soya oil, sesame oil), fatty acids or salts thereof (e.g. potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (e.g. gamma-aminobutyric acid, taurin), peptides (e.g. glutathione), native or processed proteins (e.g. gelatine), enzymes (e.g. peptidases), nucleic acids, nucleotides, flavour correctors for unpleasant flavour impressions, other flavour modulators for other, generally not unpleasant flavour impressions, other flavour-modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (e.g. lecithins, diacyl glycerols, gum arabic), stabilisers (e.g. carageenan, alginate), preservatives (e.g. benzoic acid, sorbic acid), antioxidants (e.g. tocopherol, ascorbic acid), chelating agents (e.g. citric acid), organic or inorganic acidulators (e.g. malic acid, acetic acid, citric acid, tannic acid, phosphoric acid), bitter principles (e.g. quinine, caffeine, limonin, amarogentin, humolones, lupolones, catechins, tannins), mineral salts (e.g. sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), substances preventing enzymatic browning (e.g. sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or coloured pigments (e.g. carotenoids, flavonoids, anthocyans, chlorophyll and derivatives thereof), herbs, trigeminally active substances or plant extracts containing such trigeminally active substances, synthetic, natural or nature-identical aroma substances or fragrances and odour correctors.

Dental care products (as an example of oral care preparations according to the invention), which contain one or more compounds having formula (I) according to the invention or for use according to the invention or a fragrance or aroma composition according to the invention containing one or more compounds having formula (I) generally contain an abrasive system (grinding or polishing agent), such as e.g. silicas, calcium carbonates, calcium phosphates, aluminium oxides and/or hydroxyl apatites, surface-active substances, such as e.g. sodium lauryl sulfate, sodium lauryl sarcosinate and/or cocamidopropyl betaine, humectants, such as e.g. glycerol and/or sorbitol, thickeners, such as e.g. carboxymethyl cellulose, polyethylene glycols, carrageenans and/or Laponite^®, sweeteners, such as e.g. saccharine, flavour correctors for unpleasant flavour impressions, flavour correctors for other, generally not unpleasant flavour impressions, flavour-modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), cooling agents, such as e.g. menthol derivatives (e.g. L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-trialkyl acetic acid amides (e.g. 2,2-diisopropyl propionic acid methylamide), icilin and icilin derivatives, stabilisers and active ingredients, such as e.g. sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetyl pyridinium chloride, aluminium lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, aromas and/or sodium bicarbonate or odour correctors.

Chewing gums (as a further example of oral care preparations according to the invention) which contain one or more compounds having formula (I) for use according to the invention or a fragrance or aroma composition according to the invention containing one or more compounds having formula (I) generally comprise a chewing gum base, in other words a chewing compound that becomes plastic when chewed, sugars of various types, sugar substitutes, other sweet-tasting substances, sugar alcohols (in particular sorbitol, xylitol, mannitol), cooling agents, flavour correctors for unpleasant flavour impressions, other flavour modulators for other, generally not unpleasant flavour impressions, flavour-modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, aromas and stabilisers or odour correctors.

Many different chewing gum bases are known in the prior art, a distinction being made between chewing gum and bubble gum bases, the latter being softer to allow chewing gum bubbles to be formed. Common chewing gum bases now mainly comprise, in addition to traditionally used natural resins or the natural latex chicle, elastomers such as polyvinyl acetates (PVA), polyethylenes, (low- or medium-molecular-weight) polyisobutenes (PIB), polybutadienes, isobutene- isoprene copolymers (butyl rubber), polyvinyl ethyl ethers (PVE), polyvinyl butyl ethers, copolymers of vinyl esters and vinyl ethers, styrene-butadiene copolymers (styrene-butadiene rubber, SBR) or vinyl elastomers, e.g. based on vinyl acetate/vinyl laurate, vinyl acetate/vinyl stearate or ethylene/vinyl acetate, and mixtures of the cited elastomers, as are described for example in EP 0 242 325, US 4,518,615, US 5,093,136, US 5,266,336 US 5,601 ,858 or US 6,986,709. Chewing gum bases also include other constituents such as, for example, (mineral) fillers, plasticisers, emulsifiers, antioxidants, waxes, fats or fatty oils, such as e.g. hydrogenated vegetable or animal fats, mono-, di- or triglycerides. Suitable (mineral) fillers are for example calcium carbonate, titanium dioxide, silicon dioxide, talc, aluminium oxide, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide and mixtures thereof. Suitable plasticisers or agents to prevent agglutination (detackifiers) are for example lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate), triethyl citrate. Suitable waxes are for example paraffin waxes, candelila wax, carnauba wax, microcrystalline waxes and polyethylene waxes. Suitable emulsifiers are for example phosphatides such as lecithin, mono- and diglycerides of fatty acids, e.g. glycerol monostearate.

The present invention also concerns novel trial kyl-su bstituted furan derivatives having formula (I).

Preferred compounds having formula (I) are specified and discussed in detail below.

It has already been mentioned in connection with the use according to the invention of compounds having formula (I) that compounds having formula (III) are preferred in which:

R³ denotes methyl and R⁴ denotes an alkyl radical having 3 to 6 C atoms. These compounds are 3,4-dimethyl-2-alkylfurans, which are particularly preferred because of their low odour threshold value and because of the pronounced scent notes that are commonly present from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage (in particular frequently hay/coumarin). A minty/lactone-like note commonly appears in combination with (i) menthol, (ii) (-)-carvone, (iii) menthone and (iv) isomenthone. In this respect the present invention concerns in particular the following novel compounds: ,4-Dιmethyl-2-propyl-furan 2-lsopropyl-3,4-dιmethyl-furan

-Butyl-3,4-dιmethyl-furan 2-sec-Butyl-3,4-dιmethyl-furan 2-lsobutyl-3,4-dιmethyl-furan

-tert-Butyl-3,4-dιmethyl-furan 3,4-Dιmethyl-2-(1-methyl- 3,4-Dιmethyl-2-(2-methyl- butyl)-furan butyl)-furan

3,4-Dιmethyl-2-(3-methyl-butyl)- 2-(1 ,1-Dιmethyl-propyl)- 2-(1 ,2-Dιmethyl-propyl)- furan 3,4-dιmethyl-furan 3,4-dιmethyl-furan

2-(2,2-Dιmethyl-propyl)- 3,4-dιmethyl-furan

3,4-Dιmethyl-2-(1-methyl- 3,4-Dιmethyl-2-(2-methyl- 3,4-Dιmethyl-2-(3-methyl- pentyl)-furan pentyl)-furan pentyl)-furan

3,4-Dιmethyl-2-(4-methyl- 2-(1 -Ethyl-butyl)- 2-(2-Ethyl-butyl)- pentyl)-furan 3,4-dιmethyl-furan 3,4-dιmethyl-furan

2-(1 ,2-Dιmethyl-butyl)- 2-(1 ,3-Dιmethyl-butyl)-

2-(1 ,1-Dιmethyl-butyl)- 3,4-dιmethyl-furan 3,4-dιmethyl 3,4-dιmethyl-furan

-furan

2-(2,3-Dιmethyl-butyl)-

2-(2,2-Dιmethyl-butyl)- 2-(3,3-Dιmethyl-butyl)- 3,4-dιmethyl-furan 3,4-dιmethyl-furan 3,4-dιmethyl-furan

2-(1 -Ethyl-1 -methyl-propyl)- 2-(1 -Ethyl-2-methyl-propyl)- 3,4-dιmethyl-furan 3,4-dιmethyl-furan The use of novel 3-ethyl-4-methyl-2-alkylfurans, i.e. of compounds having formula (I) in which R¹ = H, R² = methyl, R³ = ethyl and R⁴ = alkyl with 3 to 6 C atoms is also particularly preferred. These 3-ethyl-4-methyl-2-alkylfurans commonly have a minty and/or lactone-like note in addition to a hay note. The use of the following 3-ethyl-4-methyl-2-alkylfurans is particularly preferred:

-Ethyl-4-methyl-2-propyl-fu ran 3-Ethyl-2-ιsopropyl-4-methyl-furan

-Butyl-3-ethyM-methyl-furan 2-sec-Butyl-3-ethyl-4-methyl-furan 3-Ethyl-2-ιsobutyl-4-methyl-furan

2-tert-Butyl-3-ethyl-4-methyl-furan 3-Ethyl-4-methyl- 3-Ethyl-4-methyl-

2-(1 -methyl-butyl )-fu ran 2-(2-methyl-butyl)-furan

3-Ethyl-4-methyl- 2-(1 ,1-Dιmethyl-propyl)- 2-(1 ,2-Dιmethyl-propyl)- 2-(3-methyl-butyl)-furan 3-ethyl-4-methyl-fu ran 3-ethyl-4-methyl-fu ran

2-(2,2-Dιmethyl-propyl)-3-ethyl-4-m ethyl-furan -Ethyl-4-methyl- 3-Ethyl-4-methyl- 3-Ethyl-4-methyl- -(1 -methyl-pentyl)-furan 2-(2-methyl-pentyl)-furan 2-(3-m8thyl-pentyl)-furan

-Ethyl-4-methyl- -(4-m8thyl-pentyl)-furan 3-Ethyl-2-(2-ethyl-butyl)-4-methyl-

3-Ethyl-2-(1 -ethyl-butyl)- furan

4-methyl-furan

-(1 ,1-Dιmethyl-butyl)- 2-(1 ,2-Dιmethyl-butyl)- 2-(1 ,3-Dιmethyl-butyl)- -ethyl-4-methyl-furan 3-ethyl-4-methyl-furan 3-ethyl-4-methyl-furan

2-(2,2-Dιmethyl-butyl)- 2-(2,3-Dιmethyl-butyl)- 2-(3,3-Dιmethyl-butyl)- 3-ethyl-4-methyl-furan 3-ethyl-4-methyl-furan 3-ethyl-4-methyl-furan

3-Ethyl-2-(1 -ethyl-1 -methyl-propyl) 3-Ethyl-2-(1-ethyl-2-methyl-propyl) -4-methyl-furan -4-methyl-furan Due to their commonly low odour threshold values and interesting sensorial characteristics, the novel 2-alkyl-4-methyl-3-propylfurans having formula (III) wherein R³ = n-propyl and R⁴ = alkyl with 3 to 6 C atoms are also preferred.

Here R⁴ denotes in particular

n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also preferred and novel is the compound 2-ethyl-4-methyl-3-propylfuran according to the formula below:

2-Ethyl-4-methyl-3-propyl-furaπ Also preferred is the use of novel 2-alkyl-3-isopropyl-4-methylfurans, i.e. of compounds having formula (III) wherein R³ = isopropyl and R⁴ = alkyl. The corresponding graphical formula is illustrated below:

R⁴ is particularly preferably n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert- butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1 -dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also preferred is the use of the following novel compounds having formula (II) wherein R² = methyl, R³ = isopropyl and R⁴ = methyl or ethyl:

3-lsopropyl-2,4-dimethyl-furaπ 2-Ethyl-3-isopropyl-4-methyl-furaπ

Also preferred is the use of certain novel 2-alkyl-4-methyl-3-n-butylfurans having the formula below:

wherein R⁴ = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2 - dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also preferred is the use of 3-butyl-2,4-dimethylfuran and 3-butyl-2-ethyl-4- methylfuran

3-Butyl-2,4-dimethyl-furaπ 3-Butyl-2-ethyl-4-methyl-furaπ

Also preferred is the use of the novel 2-alkyl-3-isobutyl-4-methylfurans having the formula below:

wherein R⁴ = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl. Also preferred is the use of

2-Ethyl-3-isobutyl-4-methyl-furan

Also preferred is the use of the following novel 2-alkyl-4-methyl-3-sec-butylfurans

wherein R⁴ = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also preferred is the use of the following novel 2-alkyl-4-methyl-3-tert-butylfurans:

wherein R⁴ = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also preferred are the following 3-alkyl-2,4-dimethylfurans:

wherein R³ = 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also particularly preferred are the following novel dimethyl pentylfurans:

2,3-Dimethyl-5-peπtyl-furaπ 3,5-Dimethyl-2-peπtyl-furaπ

Also particularly preferred are the following 4-alkyl-2,3-dimethylfurans:

wherein R² = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also particularly preferred are the following 5-alkyl-2,3-dimethylfurans:

wherein R¹ = isopropyl, sec-butyl, isobutyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, 1 - methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2- ethylbutyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1-methylpropyl, 1- ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl.

The following 2-alkyl-3,5-dimethylfurans are particularly preferred:

wherein R¹ = n-propyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl. Also particularly preferred are the following 3-alkyl-2,5-dimethylfurans:

wherein R² = sec-butyl, isobutyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2- dimethylpropyl, 1 ,1 -dimethylpropyl, 2,2-dimethylpropyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl.

Also particularly preferred are the following 3,4-diethyl-2-alkylfurans:

wherein R⁴ = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 , 1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl.

Some compounds having formula (I) with an unrestricted meaning of R¹, R², R³, R⁴ are already known. Various documents describe trisubstituted furans having formula (I) as synthesis building blocks, but none of these documents mentions the sensorial properties:

- JP 04-103778 describes the synthesis of 3-alkenyl-2-hexyl-5-methylfurans, - JP 55-162733 describes the synthesis of 2,4-dimethyl-3-n-pentylfuran,

- JP 56-016483 describes 2,4-dimethyl-3-n-propylfuran and similar compounds as reactants in the production of cyclopentenones,

- EP 0 010 761 describes 2,4-dimethyl-3-alkyl- or alkenylfurans as intermediates for the synthesis of cyclopentenones for prostaglandins and agro-chemicals (3- alkyl or alkenyl: ethyl, propenyl, propynyl),

- SU 157977 describes the synthesis of 2,3-dimethyl-5-propylfuran, 2-ethyl-3- methylpropylfuran,

- FR 2870740 describes alkylfurans in general for the cosmetic treatment of cellulite, wherein chain lengths of C10 to C22 are preferred.

A (not exhaustive) overview is provided below of sensorial characteristics and of foodstuffs containing trisubstituted furans not for use according to the invention.

J. Agric. Food Chem. 2003, 51 (17), 5067-5072 describes the sensorial characteristics of 2,3,5-trimethylfuran as a constituent of hazelnuts as "burnt, coffee- or chocolate-like, roasted, sweet".

According to J. Science Food Agric. (2002), 82(8), 840-847 and J. Agric. Food Chem. (2001 ), 49(3), 1364-1369 and Zeitschrift fur Lebensmittel-Untersuchung und -Forschung 1976, 160(3), 277-91 , 2,3,5-trimethylfuran was found in roasted coffee.

2,3,4-Trimethylfuran was found in roasted coffee, see for example Zeitschrift fur Lebensmittel-Untersuchung und -Forschung 1987, 184(3), 179-86 or J. Agric. Food Chem. 1987, 35(3), 340-6.

3,5-Dimethyl-2- ethenylfuran is mentioned in the following documents: Zeitschrift fuer Lebensmittel-Untersuchung und -Forschung 1992, 195(2), 1 12-19 (aroma components of a reaction of cysteine and rhamnose), J. Essential Oil Research 1991 , 3(2), 107-10 (gum resin, mastic), Progress in Food and Nutrition Science 1981 , 5 (1 -6, Maillard reaction in food), 71-9 and Zeitschrift fuer Lebensmittel-Untersuchung und -Forschung 1976, 160(3), 277-91 (malted or roasted coffee).

2,5-Dimethyl-3-ethylfuran was mentioned in Developments in Food Science 1986, 13 (amino-carbonyl reaction in food biology systems), 145-54 (model system for the Maillard reaction).

According to Acta Alimentaria Polonica 1977, 3(3), 203-7, 4,5-dimethyl-2- ethenylfuran was found in a low-boiling fraction of a commercially available smoke aromatising product.

The invention is illustrated in greater detail below by means of examples. Unless otherwise specified, all figures stated relate to the weight.

Example 1 : Production examples

Example 1 a: Synthesis of 3,4-dimethyl-2(5H)-furanone (not according to the invention)

37.8 g (1.0 mol) of sodium borohydride in 215 ml of 1 % sodium hydroxide solution (54 mmol) are slowly added to a suspension of 126 g (1.0 mol) of dimethyl maleic acid anhydride in 200 ml of water in such a way that the internal temperature of 30°C is not exceeded during cooling. The mixture is stirred for a further 2.5 h at 20°C. 1 18 g of 50% sulfuric acid (0.6 mol) are added to the reaction mixture and it is heated for 1 h at 90°C. 250 ml of diethyl ether are added, the aqueous phase is saturated with ammonium chloride, and the organic phase is separated off and dried with sodium sulfate. After distilling off the solvent, 87.3 g of crude product are obtained which still contain around 17% of dimethyl maleic acid anhydride. The 3,4-dimethyl-2(5H)-furanone can be obtained in pure form by repeated recrystallisation from diethyl ether.

MS (El): 83 (100), 112 (100), 55 (95), 39 (68), 53 (42), 54 (33), 41 (25), 51 (18), 84 (17), 56 (17), 50 (16), 113 (12), 52 (11 ), 40 (9), 38 (7), 67 (8), 69 (6).

¹H-NMR (CDCI₃, 400 MHz): 1.82 (s, 3 H), 2.0 (s, 3 H), 4.6 (s, 2 H). ¹³C-NMR (CDCI₃, 90 MHz): 8.3 (CH3), 12.3 (CH3), 72.5 (CH2), 123.0 (C), 156.3 (C), 175.4 (C).

Examples 1 b - 1g: Synthesis of 3,4-dimethyl-2-alkylfurans, general instructions:

0.1 1 mol (1 eq) of 3,4-dimethyl-2(5H)-furanone (see Example 1a) are placed in 250 ml of diethyl ether under protective gas and 0.12 mol (1.1 eq) of alkyl magnesium bromide solution are added under reflux within 1 hour. The mixture is refluxed for a further 3 h. It is cooled to 10°C, 50 ml of 10% hydrochloric acid are added and the mixture is stirred for 30 min at room temperature. The organic phase is separated off, washed with 50 ml of 10% sodium hydroxide solution and 50 ml of saturated sodium chloride solution, dried over sodium sulfate and the solvent is distilled off under vacuum. The crude product is distilled under vacuum and optionally purified by chromatography on silica gel (pentane/diethyl ether).

Example 1 c: 3,4-Dimethyl-2-n-heptylfuran (not according to the invention):

MS (El): 109 (100), 123 (24), 194 (18), 1 10 (12), 79 (9), 41 (7), 81 (4), 29 (3), 55

(3), 43 (3).

¹H-NMR (CDCI₃, 400 MHz): 0.87 (t, 3 H₁ J = 7.0 Hz), 1.24 - 1.32 (m, 8 H), 1.57 (m, 2 H), 1.86 (s, 3 H, 1.91 (d, 3 H, J = 1.1 Hz), 2.51 (t, 2 H, J = 7.5 Hz), 7.03 (s, 1 H). ¹³C-NMR (CDCI₃, 100 MHz): 8.0 (CH3), 8.4 (CH3), 14.0 (CH3), 22.7 (CH2), 26.3 (CH2), 28.5 (CH2), 29.1 (CH2), 29.2 (CH2), 31.8 (CH2), 1 14.4 (C), 120.9 (C), 136.2 (CH), 151.5 (C).

Example 1 d: 3,4-Dimethyl-2-n-hexylfuran

MS (El): 109 (100), 180 (30), 123 (20), 110 (17), 79 (15), 41 (14), 81 (7), 39 (6),

43 (5), 29 (5).

¹H-NMR (CDCI₃, 400 MHz): 0.88 (t, 3 H, J = 7.0 Hz), 1.24 - 1.33 (m, 6 H), 1.56 (m, 2 H), 1.86 (s, 3 H, 1.91 (d, 3 H, J = 1.1 Hz), 2.51 (t, 2 H, J = 7.5 Hz), 7.03 (s, 1 H). ¹³C-NMR (CDCI₃, 100 MHz): 8.0 (CH3), 8.4 (CH3), 14.0 (CH3), 22.6 (CH2), 26.2 (CH2), 28.5 (CH2), 28.9 (CH2), 31.6 (CH2), 1 14.4 (C), 120.9 (C), 136.2 (CH), 151.5 (C).

Example 1e: 3,4-Dimethyl-2-n-butylfuran, MS (El): 109 (100), 152 (25), 79 (12), 1 10 (10), 41 (6), 53 (6), 81 (6), 39 (4), 153 (3), 77 (3).

¹H-NMR (CDCI₃, 400 MHz): 0.91 (t, 3 H, J = 7.4 Hz), 1.32 (m, 2 H), 1.56 (m, 2 H), 1.86 (m, 3 H), 1.91 (d, 3 H, J = 1.3 Hz), 2.52 (t, 2 H, J = 7.6 Hz), 7.03 (m, 1 H). ¹³C-NMR (CDCI₃, 100 MHz): 7.9 (CH3), 8.4 (CH3), 13.9 (CH3), 22.3 (CH2), 26.0 (CH2), 30.7 (CH2), 1 14.4 (C), 121.0 (C), 136.2 (CH), 151.5 (C).

Example 1f: 3,4-Dimethyl-2-n-propylfuran, MS (El): 109 (100), 138 (30), 79 (17), 110 (9), 53 (8), 41 (8), 81 (7), 27 (4), 77 (4), 65 (3).

¹H-NMR (CDCI₃, 400 MHz): 0.91 (t, 3 H₁ J = 7.4 Hz), 1.61 (tq, J = 7.4 Hz, 2 H), 1.86 (m, 3 H), 1.91 (d, 3 H, J = 1.2 Hz), 2.50 (t, 2 H, J = 7.4 Hz), 7.03 (m, 1 H). ¹³C-NMR (CDCI₃, 100 MHz): 8.0 (CH3), 8.4 (CH3), 13.8 (CH3), 21.9 (CH2), 28.3 (CH2), 114.6 (C), 120.9 (C), 136.3 (CH), 151.3 (C).

Example 1g: 3,4-Dimethyl-2-ethylfuran (not according to the invention) MS (EI): 109 (100), 124 (45), 79 (22), 53 (1 1 ), 39 (10), 81 (10), 41 (9), 1 10 (9), 27 (5), 65 (4).

¹H-NMR (CDCI₃, 400 MHz): 1.17 (t, 3 H, J = 7.6 Hz), 1.87 (m, 3 H), 1.91 (d, 3 H, J = 1.2 Hz), 2.55 (dq, 2 H₁ J = 0.4, 7.6 Hz), 7.03 (d, 1 H, J = 1.2 Hz). ¹³C-NMR (CDCI₃, 100 MHz): 7.9 (CH3), 8.4 (CH3), 12.9 (CH3), 19.7 (CH2), 1 13.7 (C), 121.1 (C), 136.2 (CH), 152.4 (C).

Example 1 h: Synthesis of 3,4-dimethyl-2-n-pentylfuran

16.8 g (0.15 mol) of 3,4-dimethyl-2(5H)-furanone (from Example 1 a) are placed in 250 ml of diethyl ether under protective gas and 82.5 ml of pentyl magnesium bromide solution (2.0 M in diethyl ether, 0.165 mol) are added under reflux within 1 hour. The mixture is refluxed for a further 3 h. It is cooled to 10°C, 62 ml of 10% hydrochloric acid (-0.17 mol) are added and the mixture is stirred for 30 min at 20°C. The organic phase is separated off, washed with 70 ml of 10% sodium hydroxide solution and 50 ml of saturated sodium chloride solution, dried over sodium sulfate and the solvent is distilled off under vacuum. The crude product is distilled under vacuum and purified by chromatography on silica gel (pentane/diethyl ether).

MS (El): 109 (100), 166 (32), 1 10 (13), 41 (8), 53 (7), 81 (5), 123 (4), 77 (4), 39 (3), 167 (3), 95 (3), 55 (3), 65 (2), 67 (2), 96 (2), 91 (2), 43 (2).

¹H-NMR (CDCI₃, 400 MHz): 0.88 (t, 3 H, J = 7.0 Hz), 1.30 (m, 4 H), 1.59 (m, 2 H), 1.86 (s, 3 H, 1.91 (d, 3 H, J = 1.1 Hz), 2.51 (t, 2 H₁ J = 7.5 Hz), 7.03 (s, 1 H). ¹³C-NMR (CDCI₃, 90 MHz): 7.9 (CH3), 8.4 (CH3), 14.0 (CH3), 22.4 (CH2), 26.2 (CH2), 28.2 (CH2), 31.4 (CH2), 1 14.3 (C), 120.9 (C), 136.2 (CH), 151.5 (C).

Example 1 i: Synthesis of 2,3-dimethyl-5-alkylfurans, general instructions:

2.5 g (26 mmol, 1.0 eq) of 2,3-dimethylfuran are placed in 20 ml of tetrahydrofuran under protective gas and 0.12 ml (30 mmol, 1.15 eq) of n-butyl lithium solution (2.5 M in hexane) are added at 0°C. The mixture is stirred for 2 h at 20°C. 3.74 g of 1 -butyl bromide (27.3 mmol, 1.05 eq) are slowly added dropwise at 20°C and the mixture is stirred for 18 h at 20°C. 20 ml of water and 100 ml of diethyl ether are added, the organic phase is separated off, washed twice with 20 ml of saturated sodium chloride solution, dried over sodium sulfate and the solvent is distilled off under vacuum. The crude product is purified by chromatography on silica gel (pentane/diethyl ether).

Example 1 j: 2,3-Dimethyl-5-n-butylfuran

MS (El): 109 (100), 152 (22), 43 (14), 1 10 (9), 41 (3), 39 (3), 153 (3), 95 (8), 65

(2), 27 (2).

¹H-NMR (CDCI₃, 400 MHz): 0.92 (t, 3 H, J = 7.3 Hz), 1.36 (m, 2 H), 1.58 (m, 2 H), 1.89 (d, 3 H, J = 0.9 Hz), 2.15 (m, 3 H), 2.52 (t, 2 H, J = 7.6 Hz), 5.7 (m, 1 H). ¹³C-NMR (CDCI₃, 100 MHz): 9.9 (CH3), 1 1.2 (CH3), 13.9 (CH3), 22.4 (CH2), 27.7 (CH2), 30.4 (CH2), 107.8 (CH), 1 14.1 (C), 145.1 (C), 153.5 (C). Example 1 k: 2,3-Dimethyl-5-n-pentylfuran

MS (El): 109 (100), 166 (25), 43 (12), 110 (10), 95 (3), 39 (3), 29 (2), 65 (2), 53

(2), 27 (2).

¹H-NMR (CDCI₃, 400 MHz): 0.90 (t, 3 H, J = 7.0 Hz), 1.32 (m, 4 H), 1.59 (m, 2 H), 1.89 (d, 3 H, J = 0.9 Hz), 2.15 (m, 3 H), 2.51 (t, 2 H, J = 7.6 Hz), 5.7 (m, 1 H). ¹³C-NMR (CDCI₃, 100 MHz): 9.9 (CH3), 1 1.2 (CH3), 14.0 (CH3), 22.5 (CH2), 27.9 (CH2), 28.0 (CH2), 31.5 (CH2), 107.8 (CH), 114.1 (C), 145.1 (C), 153.6 (C).

Example 11: Synthesis of 2-pentyl-3,5-dimethylfuran

n-Butyl lithium (4 ml of a 2.5 M solution, 10 mmol) is placed in dry tetrahydrofuran (10 ml) under protective gas at -20 °C. 822 mg of 3-methylfuran (10 mmol) are dissolved in 6 ml of dry tetrahydrofuran and slowly added dropwise. After stirring for 2 h at -20°C, 1 -iodine pentane (2.18 g, 11 mol) in 6 ml of tetrahydrofuran is added dropwise at -15°C and stirred for 1 h at -15°C and for 18 h at 20°C. Ice is added. The mixture is extracted with diethyl ether, the organic phase is dried over sodium sulfate and the solvent is distilled off under vacuum. The mixture is chromatographed over silica gel (pentane/diethyl ether).

2.8 ml of n-butyl lithium (2.5 M solution, 7 mmol) are placed under protective gas at -20 °C and the crude product of 2-pentyl-3-methylfuran and 2-pentyl-4- methylfuran is slowly added dropwise. After 2 h 1 g of methyl iodide (7 mmol) is added and the mixture is stirred for 1 h at -15°C and for 12 h at 20°C. Ice is added. The mixture is extracted with diethyl ether, the organic phase is dried over sodium sulfate and the solvent is distilled off under vacuum. A crude material is obtained by flash chromatography (length 30 cm, diameter 1.5 cm, diol, Merck 30 g, pentane/diethyl ether 100/0). 2-Pentyl-3,5-dimethylfuran eluted together with 2- pentyl-4,5-dimethylfuran. This is purified by HPLC: Phenomenex 5u ODS (C18) HyperClone, 250 x 10.0 mm. Starting condition 0.1 % formic acid (aq)/methanol (20/80; v/v), increased in 20 min to (6/94; v/v) and held for 5 min. 2-Pentyl-3,5-dimethylfuran (17.5 min) eluted before 2-pentyl-4,5-dimethylfuran (18.6 min).

MS (El): 109 (100), 166 (13), 43 (8), 1 10 (5), 41 (3), 39 (2), 79 (1 ), 67 (1 ), 65 (1 ), 108 (1 ), 77 (1 ), 53 (1 ), 96 (1 ), 66 (1 ).

¹H-NMR (CDCI₃, 400 MHz): 0.89 (t, 3 H, J = 7.0 Hz), 1.31 (m, 2 H), 1.31 (m, 2 H), 1.59 (m, 2 H), 1.89 (s, 3 H), 2.20 (s, 3 H), 2.50 (t, 2 H, J = 7.5 Hz), 5.73 (s, 1 H). ¹³C-NMR (CDCI₃, 90 MHz): 9.9 (CH3), 1 1.5 (CH3), 14.1 (CH3), 22.7 (CH2), 29.0 (CH2), 29.8 (CH2), 31.6 (CH2), 108.5 (CH), 114.2 (C), 148.9 (C), 149.7 (C).

Example 1 m: Synthesis of 2,5-dimethyl-3-pentylfuran

449 mg of 2,5-dimethyl-3(2H)-furanone are placed in 3 ml of diethyl ether and 2.5 ml of pentyl magnesium bromide solution (2 M in diethyl ether, 5 mmol) are added at 0°C. The mixture is refluxed for 2 h, dilute sulfuric acid is added and the organic phase is separated off. The aqueous phase is extracted twice with diethyl ether, the combined organic phases are dried over sodium sulfate and the solvent is distilled off under vacuum. The crude product is purified by chromatography on silica gel (pentane/diethyl ether).

MS (El): 109 (100), 1 10 (51 ), 43 (48), 166 (8), 95 (22), 123 (21 ), 167 (4), 108 (4), 11 1 (4), 41 (3).

¹H-NMR (CDCI₃, 400 MHz): 0.88 (t, 3 H, J = 7.0 Hz), 1.30 (m, 2 H), 1.30 (m, 2 H), 1.47 (m, 2 H), 2.15 (s, 3 H), 2.21 (s, 3 H), 2.24 (t, 2 H, J = 7.2 Hz), 5.75 (s, 1 H). ¹³C-NMR (CDCI₃, 90 MHz): 1 1.3 (CH3), 13.4 (CH3), 14.0 (CH3), 22.5 (CH2), 24.8 (CH2), 30.1 (CH2), 31.5 (CH2), 107.4 (CH), 119.8 (C), 145.0 (C), 148.9 (C). Example 2: Perfume composition (fragrance composition)

Ag rum ex LC 10.00

Amarocit® 10% in DPG 10.00

Ambroxide cryst. 10.00

Basil oil 10.00

Calone 1951 10% in DPG 10.00

Cedarwood oil 10.00

Cedrol cryst. 50.00

Citral 10% in DPG 10.00

Citronellol 5.00

Cyclogalbanat® 10% in DPG 15.00

Dihydromyrcenol 80.00

Farenal® 10% in DPG 5.00

Galbex 10% in DPG 25.00

Globalide® 80.00

Globanone® 40.00

Hedione 90.00

Helional 20.00

Heliotropin 5.00

Hexenol cis-3 10% in DPG 15.00

Hexenyl salicylate cis-3 10.00 beta-lonone 5.00 lso E Super 190.00

Isodamascon® 10% in DPG 10.00 lsomuscone (cyclohexadecanone) 20.00 lsoraldeine 70 20.00

Ketamber 10% in TEC 25.00

Lavandin oil grosso nat. 15.00

Lilial 20.00

Linalool 20.00

Linalyl acetate 40.00

Mandarin oil Brazil, green 50.00

Timberol® 40.00

Vanillin 5.00

Veloutone 10% in DPG 20.00

Ysamber K® 10.00

Total 1000.00

DPG: dipropylene glycol, TEC = triethyl citrate Description of the scent of the perfume composition without addition of 3,4- dimethyl-2-n-butylfuran: fresh, woody.

According to perfumers, the addition of 1 wt.% of 3,4-dimethyl-2-n-butylfuran makes this perfume composition more complex, more vibrant, more natural and more harmonious, with the addition of a herbal/spicy and hay-like/coumarin-like note and the strengthening of fresh, woody and floral aspects, making the perfume composition more masculine overall. 3,4-Dimethyl-2-n-butylfuran blends into the composition well, it imparts an individual character to the composition through its intrinsic odour and unites the different olfactory elements. 3,4-

Dimethyl-2-n-butylfuran also added greater fullness and staying power.

Example 3: Shampoo

The perfume oil composition from Example 2 (after addition of 3,4-dimethyl-2- n-butylfuran) was incorporated in a proportion of 0.5 wt.% into a basic shampoo matrix with the following composition:

Sodium lauryl ether sulfate 12% (e.g. Texapon NSO, Cognis Deutschland GmbH)

Cocamidopropylbetaine 2% (e.g. Dehyton K, Cognis Deutschland GmbH)

Sodium chloride 1.4%

Citric acid 1.3%

Phenoxyethanol, methyl, ethyl, butyl and propyl paraben 0.5%

Water 82.8%

The pH of the basic shampoo matrix was around 6. It was used to make 100 ml of a 20 wt.% aqueous shampoo solution. 2 strands of hair were washed together in this shampoo solution for 2 minutes and then rinsed under running hand-hot water for 20 seconds. One hair strand was then packed wet into aluminium foil and the second was dried with a hair dryer. The olfactory quality of both hair strands was assessed by a panel. Both hair strands had a generally masculine woody, spicy scent with herbal and hay-like/coumarin-like echoes and floral aspects, the overall impression being found to be complex, vibrant, rounded and harmonious.

Example 4: Fabric conditioner

The perfume oil composition from Example 2 (after addition of 3,4-dimethyl-2- n-butylfuran) was incorporated in a proportion of 0.5 wt.% into a basic fabric conditioner matrix with the following composition:

Quaternary ammonium methosulfate (esterquat), approx. 90% 5.5% (e.g. Rewoquat WE 18, Witco Surfactants GmbH) Alkyl dimethyl benzyl ammonium chloride, approx. 50% 0.2%

(e.g. Preventol R50, Bayer AG) Dye solution, approx. 1 % 0.3%

Water 94.0%

The pH of the basic fabric conditioner matrix was in the range from 2 to 3. Two fabric cloths were washed with 370 g of a 1 % aqueous fabric conditioner solution in a line test machine using the conditioning program for 30 minutes at 20°C. The cloths were wrung out and then spun for 20 seconds. One cloth was shrink-wrapped wet and one hung up to dry. The olfactory quality of both cloths was then assessed by a panel. Both cloths had a generally masculine woody, spicy scent with herbal and hay-like/coumarin-like echoes and floral aspects, the overall impression being found to be complex, vibrant, rounded and harmonious. Example 5: Washing powder

The perfume oil composition from Example 2 (after addition of 3,4-dimethyl-2- n-butylfuran) was incorporated in a proportion of 0.4 wt.% into a basic washing powder matrix with the following formulation:

Linear Na alkyl benzene sulfonate 8.8 %

Ethoxylated fatty alcohol C12-18 (7 EO) 4.7 %

Na soap 3.2 %

Defoaming agent

DOW CORNING® 2-4248S

POWDERED ANTIFOAM,

silicone oil on zeolite as carrier 3.9 %

Zeolite 4A 28.3 %

Na carbonate 1 1.6 %

Na salt of a copolymer of acrylic

and maleic acid (Sokalan CP5) 2.4 %

Na silicate 3.0 %

Carboxymethylcellulose 1.2 %

Dequest 2066 2.8 %

([[(Phosphonomethyl)imino]bis[(ethylene nitrilo)bis

(methylene)]]tetrakis-phosphonic acid, sodium salt)

Optical brightener 0.2 % Na sulfate 6.5 %

Protease 0.4 %

Sodium perborate tetrahydrate 22.0 %

TAED 1.0 %

Two fabric cloths were washed with 370 g of a 1 % aqueous washing powder solution (the pH of the washing powder solution is well within the basic range) in a line test machine using the main wash cycle for 45 minutes at 60°C. The cloths were first rinsed with cold water for 5 minutes, wrung out and then spun for 20 seconds. One cloth was shrink-wrapped wet and one hung up to dry. The olfactory quality of both cloths was then assessed by a panel. Both cloths had a generally masculine woody, spicy scent with herbal and hay- like/coumarin-like echoes and floral aspects, the overall impression being found to be complex, vibrant, rounded and harmonious.

Example 6: Aroma compositions (peppermint aromas)

The table below shows the substantial constituents of a non-natural recreation of a peppermint oil (aroma Y1 ) and those of a natural peppermint oil (aroma Z1 ).

Aroma Y1 Aroma Z1

Wt. % Wt. %

4-Terpineol, natural _ 1.0

Piperitone, natural, from eucalyptus 1.0 0.7

D-Limonene 1.0 1.7 trans-Sabinene hydrate - 1.2 alpha-Pinene 1.0 0.8 beta-Pinene, natural 1.0 1.0

Neomenthol, racemic 3.0 3.2

Eucalyptol (1 ,8-cineol) 3.0 5.0

Caryophyllene 2.0 2.2

Germacrene D - 2.2

L-Menthyl acetate having formula C 4.6 4.0 L-Menthone 20.0 24.0

D-lsomenthone 6.7 3.2

L-Menthol 52.0 39.0

Total: 95.3 89.2

Tasting:

The tasting was carried out by a panel of experts. Two differently aromatised fondant masses were compared in each case.

Mixture FN 1 consisted of fondant mass and the non-natural recreation of a peppermint oil (aroma Y1 , proportion: 50 ppm),

Mixture FN2 consisted of fondant mass, the non-natural recreation of a peppermint oil (aroma Y1 , proportion: 50 ppm) and 3,4-dimethyl-2-n-butylfuran

(proportion: 0.3 ppm, corresponding to 0.6 wt.% based on the mass of aroma Y1 used).

The following gustatory characteristics were found:

As the tasting table shows, the addition of 3,4-dimethyl-2-n-butylfuran to aroma Y1 (not according to the invention) strengthens the herbal and hay-like/coumarin- like notes and also intensifies the peppermint tea impression. The addition of 3,4- dimethyl-2-n-butylfuran to aroma Y1 brings about a significantly greater complexity, fullness and staying power, as a result of which it also seemed more natural and more rounded.

Mixture FQ1 consisted of fondant mass and natural peppermint oil (aroma Z1 , proportion: 50 ppm), Mixture FQ2 consisted of fondant mass, natural peppermint oil (aroma Z1 , proportion: 50 ppm) and 3,4-dimethyl-2-n-butylfuran (proportion: 0.3 ppm, corresponding to 0.6 wt.% based on the mass of aroma Z1 used).

The following gustatory characteristics were found:

As the tasting table shows, the addition of 3,4-dimethyl-2-n-butylfuran to aroma Z1 (not according to the invention) strengthens the herbal and hay-like notes and also intensifies the peppermint tea impression. The addition of 3,4-dimethyl-2-n- butylfuran to aroma Z1 brings about a significantly greater complexity, fullness and staying power, as a result of which it also seemed more natural and more rounded.

Example 7: Aroma compositions (synthetic peppermint oils)

Aroma P Aroma A1

Parts by wt. Parts by wt.

lsobutyraldehyde 0.5 0.5

3-Octanol 0.5 0.5

Dimethyl sulfide 0.5 0.5 trans-2-Hexenal 1.0 1.0 cis-3-Hexenol 1.0 1.0

4-Terpineol, natural 1.0 1.0 lsopulegol 1.0 1.0

Piperitone, natural, from eucalyptus 2.0 2.0

Linalool 3.0 3.0

8-Ocimenyl acetate, 10% in triacetin 5.0 5.0 lsoamyl alcohol 10.0 10.0

Isovaleraldehyde 10.0 10.0 alpha-Pinene 25.0 25.0 beta-Pinene, natural 25.0 25.0

Neomenthol, racemic 40.0 40.0

Eucalyptol (1 ,8-cineol), natural 50.0 50.0

L-Menthyl acetate having formula C 70.0 70.0

L-Menthone 220.0 215.0

D-lsomenthone 50.0 50.0

L-Menthol 484.5 479.5

3,4-Dimethyl-2-n-butylfuran - 10

Total: 1000.0 1000.0

According to the flavourists, the addition of 1 wt.% of 3,4-dimethyl-2-n-butylfuran having the formula (aroma A1 ) gives aroma P (not according to the invention), a non-natural recreation of a peppermint oil, herbal/spicy and hay-like/coumarin-like notes. 3,4-Dimethyl-2-n-butylfuran blends into the composition well, it gives the composition greater naturalness, complexity, fullness and staying power and rounds it off. Other formulation examples

Example F1 : Gel tooth cream effective against bad breath

Example F2: Anti-plaque tooth cream

Example F3: Anti-plaque tooth cream

Example F4: Tooth cream for sensitive teeth

Example F5: Tooth cream for sensitive teeth

Example F6: Ready-to-use mouthwash with fluoride

Example F7: Mouthwash concentrate

Example F8: Sugar-containing chewing gums

Examples F9a - 9d: Sugar-free chewing gums

Example F9a: Non-stick chewing gum

The chewing gum base K1 consisted of 2.0% butyl rubber (isobutene-isoprene copolymer, MW 400,000), 6.0% polyisobutene (MW = 43,800), 43.5% polyvinyl acetate (MW = 12,000), 31.5% polyvinyl acetate (MW = 47,000, 6.75% triacetin and 10.25% calcium carbonate. The chewing gum base K1 and the chewing gums can be produced in the same way as in US 5,601 ,858.

Example F9b: Bubble gum

The bubble gums can be produced in the same way as in US 5,093,136.

The chewing gums with formulation (I) were shaped as compact balls, those with formulation (II) as hollow balls.

Example F9c:

The chewing gum base K2 consisted of 28.5% terpene resin, 33.9% polyvinyl acetate (MW = 14,000), 16.25% hydrogenated vegetable oil, 5.5% mono- and diglycerides, 0.5% polyisobutene (MW 75,000), 2.0% butyl rubber (isobutene- isoprene copolymer), 4.6% amorphous silicon dioxide (water content approx. 2.5%), 0.05% antioxidant tert-butyl hydroxytoluene (BHT), 0.2% lecithin, and 8.5% calcium carbonate. The chewing gum base K2 and the chewing gums can be produced in the same way as in US 6,986,907.

The chewing gums with formulations (I) and (II) were shaped as sticks, those with formulation (III) as pellets. Example F9d:

Example F10: Gelatine capsule for direct consumption

The gelatine capsule suitable for direct consumption was produced in accordance with WO 2004/050069 and had a diameter of 5 mm and the weight ratio of core material to shell material was 90 : 10. The capsule opened in the mouth in less than 10 seconds and dissolved completely in less than 50 seconds.

Example F1 1 : Chewy sweet with aroma according to the invention

Preparation instructions: a) Soak the gelatine with water (1.8 times the amount of gelatine) at 70°C for 2 hours; b) Boil sugar, syrup, water, fat and lecithin at 123°C; c) Slowly mix the gelatine solution with the boiling batch; d) Stir in the aroma from Example 7 and optionally dye; e) Temper the resulting mass on a cooling table at approx. 70°C, then add the fondant and aerate for approx. 3 minutes in a drawing machine; f) Then cut and package the chewy sweet mass.

On eating the chewy sweets a powerful peppermint taste is perceived during chewing.

Example F12: Tablets with aroma according to the invention

Preparation instructions: Mix all constituents and compress into tablets in a suitable machine.

Example F13: Jelly with aroma according to the invention

Preparation instructions: Stir 41 g of this mixture into 250 ml of boiling water and leave to cool.

Example F14: Extrudate with aroma according to the invention

Preparation instructions (see also WO 03/092412):

All constituents were mixed together and transferred to a twin-screw extruder by means of single-point metering. The extrusion temperatures were between 100 and 120°C, the specific energy input was 0.2 kWh/kg. The strands emerging from the extruder's perforated die plate with 1 mm holes were cut into particles approx. 1 mm in diameter by rotating blades immediately on leaving the dies. Example F15: Fluidised bed granules with aroma according to the invention

A solution consisting of 44 wt.% water, 11 wt.% aroma A1 according to the invention from Example 7, 13 wt.% gum arabic and 32 wt.% hydrolysed starch (Maltodextrin DE 15-19) and a little green dye is granulated in a granulating apparatus of the type described in EP 163 836 (with the following features: diameter of feed base: 225 mm, spray nozzle: two-fluid nozzle; air classifying outlet: zigzag air classifier; filter: internal bag filter). The solution is sprayed into the fluidising bed granulator at a temperature of 32°C. Nitrogen is blown in at a rate of 140 kg/h to fluidise the bed content. The intake temperature of the fluidising gas is 140°C. The exhaust gas temperature is 76°C. Nitrogen is also introduced as the air classifying gas at a rate of 15 kg/h and a temperature of 50°C. The content of the fluidised bed is approx. 500 g. The granulating output is approx. 2.5 kg per hour. Free-flowing granules with an average particle diameter of 360 micrometres are obtained. The granules are round with a smooth surface. Owing to the constant pressure drop in the filter and the likewise constant bed content, it can be assumed that the granulating process is in a steady-state condition.

Example F16: Teabag with black tea or rooibos tea and granules containing aroma according to the invention

Example F16a:

800 g of rooibos tea and 33 g of the aroma particles from Example F14 with aroma A1 according to the invention from Example 7 were mixed, divided into portions and then filled into teabags. Example F16b:

850 g of black tea tannings were placed in a 5-litre Lodige ploughshare mixer and premixed and fluidised for 10 seconds. Without interrupting the mixing process, 6 g of a fine neutral oil mist (medium-chain triglyceride oil aerosol) was sprayed onto the fluidised tea leaves using a one- or two-fluid nozzle. This takes around 60 seconds. Without interrupting the mixing process, 40 g of the aforementioned coloured aroma particles from Example F15 with aroma A1 according to the invention from Example 7 were poured onto the fluidised mixture and the entire mixture was mixed for a further 60 seconds. The mixture obtained in this way was then divided into portions and filled into teabags.

Example F17: Chewing gum dragees, sugar-free

Q1 : Constituents of the crude chewing gum mass

Q2: Coating constituents

(The specified percentages by weight relate to the total mass of the coating (Q2) applied to the chewing gum dragees (Q1 ); the total mass of Q2 was around 35% based on the mass Q1 )

All constituents of the crude chewing gum mass (Q1 ) were mixed, formed into chewing gum strands and then shaped into individual chewing gum dragees. The chewing gum dragees were then wetted (gummed) in a rotating sugar-coating drum with a 40 wt.% gum arabic solution. The gummed chewing gum dragees were then coated in a rotating sugar-coating drum with the powdered mixture A which substantially consisted of spray-dried l-menthol and at least one sugar substitute (mostly chosen from isomalt, sorbitol, xylitol, maltitol and/or mannitol, powdered gum arabic can optionally be used in addition). After adequate drying with cold air the chewing gum dragees coated in this way were dried overnight. For the further application of the coating to the dried, coated chewing gum dragees with coating solution B, 15 layers were first applied by sugar coating, and in the 16^th layer a mixture of component C and mixture B was applied. Further layers were then applied using mixture B until the total weight of the coating (Q2) was around 35 wt.% of the weight of the original chewing gum dragees (Q1 ). To add gloss to the chewing gum dragees they were subsequently treated with a glossing agent consisting of a mixture of equal parts by weight of carnauba wax and beeswax. On chewing, the ready-to-use chewing gum dragees give rise to a very clear, vibrant, fresh menthol-like and natural peppermint flavour in the mouth.

Example F18: Spray-dried aroma according to the invention A green/yellow coloured spray-dried aroma according to the invention (containing maltodextrin (DE: 18-20), dextrose, gum arabic, aroma A1 from Example 7, (-)- carvone, dye and the antioxidant ascorbyl palmitate) with the following particle size distribution was produced using a pressure nozzle:

D (v 0.1 ): 26.8 micrometres, D (v 0.5): 68.02 micrometres, D (v 0.9): 126.4 micrometres

Example F19: Instant drink powder with spray-dried aroma according to the invention

45 g of this instant drink powder was dissolved in 1000 ml while stirring. The drink obtained had a refreshing, cooling lemon and peppermint flavour.

Example F20: Hard-boiled sweet with aroma according to the invention

Sugar, corn syrup and maltose were dissolved in water, boiled and vacuum- treated. The remaining ingredients were then poured into the boiled sugar mass and homogenised at boiling temperature. After cooling, hard-boiled sweets were shaped out of the resulting mass. The hard-boiled sweets had a residual water content of around 2.5 wt.%.

Example F21 : Throat sweets with a liquid-viscous core filling (centre-filled hard- boiled sweets) with aroma according to the invention

By reference to the processes described in US 6,432,441 (Example 1 ) and in US 5,458,894 and US 5,002,791 , sweets with a liquid-viscous core were produced. The two mixtures A and B were processed separately to form bases for the shell (mixture A) and core (mixture B). When consumed, the filled throat sweets obtained by co-extrusion eased coughs, sore throats and hoarseness in sufferers. Example F22: Liqueur with aroma according to the invention

A ready-to-consume alcoholic drink in the form of a peppermint-flavoured liqueur was produced by mixing 5 g of aroma A1 according to the invention from Example 7 and 100 litres of a green-coloured alcoholic/aqueous sugar solution containing 18 wt.% of sugar (sucrose) and 17.5 vol. % of alcohol (ethanol).

Example F23: Soft drink with aroma according to the invention

A ready-to-consume non-alcoholic drink in the form of a peppermint-flavoured soft drink was produced by mixing 1 g of aroma A1 according to the invention from Example 7 and 100 litres of a yellow/green-coloured 10.8 wt.% aqueous sugar solution.

Claims

Claims

1. Use of a compound having formula (I)

(I)

wherein: a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R¹, R², R³, R⁴ mutually independently denote an alkyl or alkenyl radical having 1 to 6 C atoms,

as a fragrance and/or aroma substance

and/or

as a means of rounding out and/or of imparting vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend.

2. Use according to claim 1 , wherein the total carbon number of a compound having formula (I) is not greater than 20, preferably not greater than 15.

3. Use according to one of the preceding claims, wherein for the compound having formula (I): a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, a third of the radicals R¹, R², R³ , R⁴ denotes methyl or ethyl, and a fourth of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 1 to 4 C atoms.

4. Use according to one of the preceding claims, wherein for the compound having formula (I): a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R¹, R², R³, R⁴ mutually independently each denote methyl or ethyl, but preferably methyl.

5. Use according to claim 3 or 4 as a fragrance and/or aroma substance for imparting, modifying and/or strengthening one or more scent or flavour impressions from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage.

6. Use according to one of claims 1 to 4, wherein the compound having formula (I) is a compound having formula (II),

(H)

wherein:

R² denotes methyl or ethyl, preferably methyl a first of the radicals R³, R⁴ denotes methyl or ethyl, a second of the radicals R³, R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms.

7. Use according to claim 6, wherein the compound having formula (II) is a compound having formula (III)

wherein: a first of the radicals R³ or R⁴ denotes methyl and a second of the radicals R³ or R⁴ denotes an alkyl radical having 3 to 6 C atoms, preferably n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl or 1 ,2,2- trimethylpropyl.

8. Use according to claim 7, wherein: R³ denotes methyl and

R⁴ denotes an alkyl radical having 3 to 6 C atoms, preferably n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2- ethylbutyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1-methylpropyl, 1- ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl.

9. Use according to claim 8, wherein: R³ denotes methyl and

R⁴ denotes n-butyl or n-pentyl.

10. Perfumed or aromatised item containing or consisting of:

(a) a sensorially effective amount of one or more compounds having formula (I), as defined in one of the preceding claims,

(b) one, several or all compounds selected from the group consisting of

(v) menthol,

(vi) (-)-carvone (vii) menthone and

(viii) isomenthone,

and preferably

(c) menthyl acetate.

1 1. Perfumed or aromatised item according to claim 10, wherein at least one of the compounds having formula (I) is a compound having formula (III)

(III)

wherein: a first of the radicals R³ or R⁴ denotes methyl and a second of the radicals R³ or R⁴ denotes an alkyl radical having 3 to 6 C atoms.

12. Perfumed or aromatised item according to one of claims 10 to 1 1 , wherein the item is selected from the group consisting of:

fragrance or aroma composition, preferably peppermint or spearmint aroma composition, - food preparation, preferably ready-to-consume or not ready-to-consume foodstuff, oral care preparation and consumable preparation.

13. Perfumed or aromatised item according to one of claims 10 to 12, containing a total amount of the one or more compounds having formula (I) which is sufficient to impart, modify and/or strengthen one or more scent or flavour impressions from the group consisting of herbal, hay (like dry grass and slightly sweet), coumarin and fennel.

14. Fragrance or aroma composition according to one of claims 12 to 13, characterised in that the fragrance or aroma composition has a total amount of one or more compounds having formula (I) in the range from 0.001 to 20 wt.%, preferably 0.01 to 20 wt.%, and most particularly preferably 0.1 to 2 wt.%, based on the total amount of fragrance or aroma composition.

15. Fragrance or aroma composition according to one of claims 12 to 14, containing:

(a) one or more compounds having formula (I), as defined in one of claims

1 to 9, in a total amount in the range from 0.01 to 20 wt.%, preferably 0.1 to 2 wt.%, and (b) (i) menthol, preferably l-menthol, in an amount from 1 to 80 wt.%, preferably 5 to 70 wt.%, and/or

(ii) (-)-carvone in an amount from 1 to 80 wt.%, preferably 5 to 80 wt.%, and/or

(iii) menthone, preferably (-)-menthone, and/or

(iv) isomenthone, preferably (+)-isomenthone, in a total amount from 0.5 to 60 wt.%, preferably 1 to 50 wt.%, and preferably

(c) menthyl acetate, preferably (-)-menthyl acetate in an amount from 1 to 20 wt.%, preferably 2 to 12 wt.%, particularly preferably 3 to 10 wt.%, wherein the stated quantities are based in each case on the total amount of the fragrance or aroma composition.

16. Food, oral care or consumable preparation according to one of claims 10 to 12, containing a fragrance or aroma composition according to one of claims 14 to 16 in an amount from 0.05 to 50 wt.%, preferably in the range from 0.05 to 6 wt.%, by preference in the range from 0.1 to 3 wt.%, based on the total weight of the preparation.

17. Preparation according to claim 16, wherein the preparation is ready for use and is preferably

(A) a ready-to-consume sugar-free, reduced-sugar or sugar-containing confectionery product, in particular in the form of: chocolate, filled chocolate (filled for example with an aromatised fondant mass, e.g. of the

After Eight type), chocolate bar product, fruit gum, hard-boiled or soft sweet, chewy sweet, sugar pearl, lollipop, capsule (preferably seamless capsule, preferably for direct consumption, preferably with a shell based on gelatine or alginate), chewing gum (e.g. in the form of strips, tablets, pellets, dragees, balls, hollow balls)

or (B) an oral care product (oral hygiene product), in particular in the form of: toothpaste, tooth cream, tooth gel, tooth powder, liquid tooth cleaner, foam tooth cleaner, mouthwash, tooth cream and mouthwash as a 2-in-1 product, lozenge, mouth spray, dental floss or dental chewing gum

or

(C) an alcoholic or non-alcoholic drink.

18. Process for imparting, modifying and/or strengthening one or more scent or flavour impressions from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage, wherein - one or more compounds having formula (I) as defined in one of claims 1 to

9, or a fragrance or aroma composition, preferably according to one of claims 12 to 15, which contains one or more compounds having formula (I) as defined in one of claims 1 to 9, is brought into contact with or mixed with a product.

19. Process for producing a fragrance or aroma composition with the following step:

Mixing one or more compounds having formula (I) as defined in one of claims 1 to 9 with conventional constituents of a fragrance or aroma composition,

wherein the one or more compounds having formula (I) are used in an amount which is sufficient to impart, modify and/or strengthen in the fragrance or aroma composition one or more scent or flavour impressions from the group consisting of herbal, spicy, hay (like dry grass and slightly sweet), coumarin, celery, fennel and lovage.

20. Process according to claim 19, wherein the fragrance or aroma composition is a fragrance or aroma composition according to one of claims 12 to 15 and

(a) one or more compounds having formula (I) as defined in one of claims 1 to 9, is mixed with

(b) one, several or all compounds selected from the group consisting of

(i) menthol, (ii) (-)-carvone (iii) menthone and (iv) isomenthone, and preferably

(c) menthyl acetate.

21. Compound having formula (I)

(I)

selected from the group consisting of:

,4-Dιmethyl-2-propyl-furan 2-lsopropyl-3,4-dιmethyl-furan

-Butyl-3,4-dιmethyl-furan 2-sec-Butyl-3,4-dιmethyl-furan 2-lsobutyl-3,4-dιmethyl-furan

-tert-Butyl-3,4-dιmethyl-furan 3,4-Dιmethyl-2-(1-methyl- 3,4-Dιmethyl-2-(2-methyl- butyl)-furan butyl)-furan

3,4-Dιmethyl-2-(3-methyl-butyl)- 2-(1 ,1-Dιmethyl-propyl)- 2-(1 ,2-Dιmethyl-propyl)- furan 3,4-dιmethyl-furan 3,4-dιmethyl-furan

2-(2,2-Dιmethyl-propyl)- 3,4-dιmethyl-furan

3,4-Dιmethyl-2-(1-methyl- 3,4-Dιmethyl-2-(2-methyl- 3,4-Dιmethyl-2-(3-methyl- pentyl)-furan pentyl)-furan pentyl)-furan

3,4-Dιmethyl-2-(4-methyl- 2-(1 -Ethyl-butyl)- 2-(2-Ethyl-butyl)- pentyl)-furan 3,4-dιmethyl-furan 3,4-dιmethyl-furan

2-(1 ,2-Dιmethyl-butyl)- 2-(1 ,3-Dιmethyl-butyl)-

2-(1 ,1-Dιmethyl-butyl)- 3,4-dιmethyl-furan 3,4-dιmethyl 3,4-dιmethyl-furan

-furan

2-(2,3-Dιmethyl-butyl)-

2-(2,2-Dιmethyl-butyl)- 2-(3,3-Dιmethyl-butyl)- 3,4-dιmethyl-furan 3,4-dιmethyl-furan 3,4-dιmethyl-furan

2-(1 -Ethyl-1 -methyl-propyl)- 2-(1 -Ethyl-2-methyl-propyl)- 3,4-dιmethyl-furan 3,4-dιmethyl-furan -Ethyl-4-methyl-2-propyl-fu ran 3-Ethyl-2-ιsopropyl-4-methyl-furan

-Butyl-3-ethyM-methyl-furan 2-sec-Butyl-3-ethyl-4-methyl-furan 3-Ethyl-2-ιsobutyl-4-methyl-furan

2-tert-Butyl-3-ethyl-4-methyl-furan 3-Ethyl-4-methyl- 3-Ethyl-4-methyl-

2-(1 -methyl-butyl )-fu ran 2-(2-methyl-butyl)-furan

3-Ethyl-4-methyl- 2-(1 ,1-Dιmethyl-propyl)- 2-(1 ,2-Dιmethyl-propyl)- 2-(3-methyl-butyl)-furan 3-ethyl-4-methyl-fu ran 3-ethyl-4-methyl-fu ran

2-(2,2-Dιmethyl-propyl)-3-ethyl-4-m ethyl-furan -Ethyl-4-methyl- 3-Ethyl-4-methyl- 3-Ethyl-4-methyl- -(1 -methyl-pentyl)-furan 2-(2-m8thyl-pentyl)-furan 2-(3-m8thyl-pentyl)-furan

-Ethyl-4-methyl- -(4-m8thyl-pentyl)-furan 3-Ethyl-2-(2-ethyl-butyl)-4-methyl-

3-Ethyl-2-(1 -ethyl-butyl)- furan

4-methyl-furan

-(1 ,1-Dιmethyl-butyl)- 2-(1 ,2-Dιmethyl-butyl)- 2-(1 ,3-Dιmethyl-butyl)- -ethyl-4-methyl-furan 3-ethyl-4-methyl-furan 3-ethyl-4-methyl-furan

2-(2,2-Dιmethyl-butyl)- 2-(2,3-Dιmethyl-butyl)- 2-(3,3-Dιmethyl-butyl)- 3-ethyl-4-methyl-furan 3-ethyl-4-methyl-furan 3-ethyl-4-methyl-furan

3-Ethyl-2-(1 -ethyl-1 -methyl-propyl) 3-Ethyl-2-(1-ethyl-2-methyl-propyl) -4-methyl-furan -4-methyl-furan 2-alkyl-4-methyl-3-n-propylfurans, wherein the alkyl radical is selected from the group consisting of:

n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2- trimethylpropyl,

2-ethyl-4-methyl-3-propylfuran,

2-alkyl-3-isopropyl-4-methylfurans, wherein the alkyl radical is selected from the group consisting of:

n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2- trimethylpropyl,

3-lsopropyl-2,4-dimethyl-furaπ 2-Ethyl-3-isopropyl-4-methyl-furaπ

2-alkyl-4-methyl-3-n-butylfurans, wherein the alkyl radical is selected from the group consisting of: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methyl propyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2- trimethylpropyl,

3-Butyl-2,4-dimethyl-furaπ 3-Butyl-2-ethyl-4-methyl-furaπ

2-alkyl-3-isobutyl-4-methylfurans, wherein the alkyl radical is selected from the group consisting of:

n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2- trimethylpropyl,

2-Ethyl-3-isobutyl-4-methyl-furaπ

2-alkyl-4-methyl-3-sec-butylfurans, wherein the alkyl radical is selected from the group consisting of: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1- methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl and 1,2,2- trimethylpropyl,

2-alkyl-4-methyl-3-tert-butylfurans, wherein the alkyl radical is selected from the group consisting of:

where R⁴ = n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1- methylpropyl, 1-ethyl-2-methylpropyl and 1,1,2-trimethylpropyl, 1,2,2- trimethylpropyl,

3-alkyl-2,4-dimethylfurans, wherein the alkyl radical is selected from the group consisting of:

1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1- dimethylpropyl, 2,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 -ethyl-1 -methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2- trimethylpropyl and 1,2,2-trimethylpropyl,

2,3-Dimethyl-5-peπtyl-furaπ 3,5-Dimethyl-2-peπtyl-furaπ

4-alkyl-2,3-dimethylfurans, wherein the alkyl radical is selected from the group consisting of:

= n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl,

2,2-dimethylpropyl, n-hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1- methylpropyl, 1 -ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2- trimethylpropyl,

5-alkyl-2,3-dimethylfurans, wherein the alkyl radical is selected from the group consisting of:

isopropyl, sec-butyl, isobutyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 ,2- dimethylpropyl, 1 ,1 -dimethylpropyl, 2,2-dimethylpropyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 - dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2-trimethylpropyl and 1 ,2,2-trimethylpropyl,

2-alkyl-3,5-dimethylfurans, wherein the alkyl radical is selected from the group consisting of:

n-propyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 1 ,2-dimethylpropyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2- ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1-methylpropyl, 1- ethyl-2-methylpropyl, 1,1,2-trimethylpropyl and 1,2,2-trimethylpropyl,

3-alkyl-2,5-dimethylfurans, wherein the alkyl radical is selected from the group consisting of:

sec-butyl, isobutyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2- dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1,1- dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl and 1,2,2-trimethylpropyl,

3,4-diethyl-2-alkylfurans, wherein the alkyl radical is selected from the group consisting of:

n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2- dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 -ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1- methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl and 1,2,2- trimethylpropyl.