5,5-Disubstituted tetrahydrofuran-2-ones as fragrance compounds.

Abstract

At least one formula 1 [Formula 1] The use of compound TIFF2025517558000025.tif52165 as a fragrance is proposed.

Description

[Technical field]

[0001] The present invention relates to the use of compounds according to formula 1 as fragrances or fragrance compounds. Furthermore, the present invention relates to so-called fragrance compositions comprising compounds according to formula 1, their uses and methods for imparting, modifying and / or enhancing specific fragrance notes. Furthermore, the present invention relates to perfumed products comprising compounds according to formula 1. [Background technology]

[0002] In the perfume industry, the creation of new fragrances is constantly sought. However, the creation of new fragrances or fragrance compositions entails numerous challenges. For example, in order to meet a specific demand in the market and to provide a product that matches a specific profile required by the customer, it is necessary to select a specific fragrance composition from the almost infinite possible structures known from the prior art. Although suitable fragrances exhibit very advantageous effects, they may produce unpleasant and therefore harmful odor profiles when combined with other fragrances, making them difficult or even impossible to use for certain applications.

[0003] Moreover, the current trend in the perfume industry is renewable products. However, it is a difficult task to identify renewable compounds that can be part of renewable products and have beneficial odor properties. Moreover, a perfume or perfume composition should not only have a unique odor profile, but also have so-called secondary beneficial properties. In fact, many perfume compositions known from the market not only have serious defects in use, such as low solubility and stability for storage, but also fail in subjective issues such as richness and elegance. In addition, many known perfume compositions require high dosages to achieve the desired odor result. Another requirement for modern perfumes is high biodegradability as well as dermatological and toxicological safety. As a result, there is a particularly high demand for perfumes that have a significant effect on other perfumes even at low dosages and that change a rather unpleasant odor impression into a beneficial one and / or enhance a pleasant odor impression. Summary of the Invention [Problem to be solved by the invention]

[0004] Thus, the underlying problem in the present invention was to provide a new fragrance capable of enhancing the beneficial and advantageous odor aspects of other fragrances and / or (at the same time) reducing, suppressing and / or masking the undesirable and unpleasant odor aspects.Furthermore, the new fragrance should be renewable and stable.Finally, the fragrance composition itself should have good biodegradability and be harmless to humans and the environment. [Means for solving the problem]

[0005] At least one formula 1 [ka] [In the formula, R 1 represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R 2represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] This problem is solved by the use of the compound as a fragrance.

[0006] The compounds according to formula 1 used in the present invention may exist in any stereoisomeric form or may exist as any mixture of stereoisomers.

[0007] The compounds of formula 1 described thus far, and in particular the advantages described therein, also apply to mixtures of stereoisomers of compounds of formula 1, or mixtures of different compounds of formula 1, used or employed in the present invention. Effect of the Invention

[0008] The compounds of formula 1 have olfactory properties that are quite unique and clearly different from and superior to known odorants. The suitability of the compounds of formula 1 as perfumes was previously unknown. It is therefore particularly surprising to find a perfume with valuable, interesting and complex olfactory properties in an already well-researched field. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] As mentioned above, the suitability of the compound of formula 1 as a fragrance is unclear. Similarly, a precise odor description cannot be obtained, but according to the inventors, the compound of formula 1 has a characteristic fruity, apricot, cumarin, creamy, coconut, green, mint, sweet, almond, fresh, soft, natural, tonka, tobacco and / or hay odor.

[0010] As a result, the inventors have made the surprising discovery that compounds of formula 1 are suitable as perfumes and, in low dosages and in combination with other perfumes, produce special effects that are not necessarily related to their own odor, but which impart a completely different note when combined with other perfumes, especially floral perfumes.

[0011] For clarity, by the phrase "the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond" or similar phrases, it is meant the ordinary meaning understood by a person skilled in the art, i.e., that the entire bond (solid and dotted) between the carbon atoms connected by said dotted line is a single bond or a double bond.

[0012] In a preferred embodiment of the invention, R1 represents methyl, ethyl, butyl, vinyl, allyl, 2-methylprop-1-enyl, 2-methylallyl, octyl or nonyl; and R2 represents methyl or ethyl.

[0013] In a further preferred embodiment of the present invention, the compound of formula 1 is selected from the group consisting of 5,5-dimethyltetrahydrofuran-2-one, 5-ethyl-5-methyl-tetrahydrofuran-2-one, 5,5-diethyltetrahydrofuran-2-one, 5-methyl-5-vinyl-tetrahydrofuran-2-one, 5-allyl-5-methyl-tetrahydrofuran-2-one, 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one, 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one, 5-methyl-5-octyl-tetrahydrofuran-2-one, 5-methyl-5-nonyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-furan-2-one.

[0014] Preferred compounds of the present invention have the following structural formula and odor characteristics: [Table 1] [Table 2]

[0015] In the most preferred embodiment of the present invention, the compound of formula 1 is 5,5-dimethyltetrahydrofuran-2-one. Preferably, 5,5-dimethyltetrahydrofuran-2-one has the following odor notes: fruity, apricot, cherry leaf, creamy.

[0016] In a preferred embodiment of the present invention, at least one compound of formula 1 is used in a fragrance composition to obtain at least one of the following odor notes: fruity, apricot, cherry leaf, creamy, coconut, green, mint, sweet, almond, fresh, soft, natural, tonka bean, tobacco and / or hay. Further preferred is the use of at least one compound of formula 1 to perfuming, modifying and / or enhancing a fragrance composition to be more rounded, more natural, more full-bodied, more honeyed, more intense and / or more fruity, and / or less oily and / or less mushroomy. This is however particularly surprising in light of the above odor descriptions, since some compounds of formula 1, such as 5-methyl-5-octyl-tetrahydrofuran-2-one, 5-methyl-5-nonyl-tetrahydrofuran-2-one or 5-butyl-5-ethyl-furan-2-one, do not possess any fruity, juicy or floral notes and / or even less pleasant odor notes.

[0017] Particularly surprising is the fact that the compounds of formula 1 used in the present invention are capable of imparting a highly complex and diverse overall sensory impression, which can otherwise usually only be achieved by mixtures of several components (e.g. mixtures of essential oils or spices).

[0018] Beyond their primary so-called olfactory properties, the compounds of formula 1 additionally possess beneficial secondary properties such as high substantivity, especially compared to fragrances with similar olfactory properties, as well as high stability in certain media and preparation methods, high scalability, and also biodegradability.

[0019] In connection with the preferred use for perfuming, modifying and / or enhancing an odor note, it is also recognized that the compounds of formula 1 can perform an excellent function as so-called boosters. Therefore, in one aspect, the present invention relates to the use of at least one compound of formula 1 for enhancing one or more odor notes. As explained above, the odor notes to be enhanced are preferably selected from mellow, natural, rich, honey, intense and / or fruity. Preferably, the at least one compound of formula 1 is 5,5-dimethyltetrahydrofuran-2-one.

[0020] Moreover, the compounds of formula 1 used in the present invention can enhance the strength of the perfume mixture (perfume composition) and round out the overall odor of the mixture. Therefore, the compounds described herein can be used to impart more richness, freshness, (bright) strength, brightness, mellowness, harmony, naturalness and / or less oiliness to the perfume composition, and in particular, the compounds can be used to impart more naturalness, mellowness and / or more freshness to the perfume composition.

[0021] Furthermore, the compounds of formula 1 are suitable as agents for improving the substantivity and / or retention of perfume compositions.

[0022] The compounds of formula 1 can be used in a variety of products; they can be used as the sole perfume, but can also be combined particularly advantageously with other perfumes in different amounts to form perfume mixtures and to create new and unique scent compositions. Thus, one aspect of the present invention also relates to perfume mixtures comprising at least one compound of formula 1, preferably 5,5-dimethyltetrahydrofuran-2-one, and possible additional components (such as solvents).

[0023] The fragrance composition according to the present invention comprises at least one compound represented by formula 1 [ka] [In the formula, R 1 represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R 2 represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] Compounds of; and It comprises or consists of at least one additional flavouring.

[0024] In a preferred embodiment of the invention, R1 represents methyl, ethyl, butyl, vinyl, allyl, 2-methylprop-1-enyl, 2-methylallyl, octyl or nonyl; and R2 represents methyl or ethyl. In a further preferred embodiment of the present invention, the compound of formula 1 is selected from the group consisting of 5,5-dimethyltetrahydrofuran-2-one, 5-ethyl-5-methyl-tetrahydrofuran-2-one, 5,5-diethyltetrahydrofuran-2-one, 5-methyl-5-vinyl-tetrahydrofuran-2-one, 5-allyl-5-methyl-tetrahydrofuran-2-one, 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one, 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one, 5-methyl-5-octyl-tetrahydrofuran-2-one, 5-methyl-5-nonyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-tetrahydrofuran-2-one, and 5-butyl-5-ethyl-furan-2-one. Most preferably, the compound of formula 1 is 5,5-dimethyltetrahydrofuran-2-one.

[0025] Preferably, the fragrance composition according to the invention comprises or consists of at least one compound of formula 1 and two or more additional fragrances. More preferably, the fragrance composition according to the invention comprises or consists of at least one compound of formula 1 and three or more additional fragrances. Most preferably, the fragrance composition according to the invention comprises or consists of at least one compound of formula 1 and four or more additional fragrances.

[0026] Preferably, the fragrance composition according to the invention comprises or consists of 5,5-dimethyltetrahydrofuran-2-one and two or more additional fragrances. More preferably, the fragrance composition according to the invention comprises or consists of 5,5-dimethyltetrahydrofuran-2-one and three or more additional fragrances. Most preferably, the fragrance composition according to the invention comprises or consists of 5,5-dimethyltetrahydrofuran-2-one and four or more additional fragrances.

[0027] The compounds of formula 1 in the present invention are typically used in sensory effective amounts, that is, the total amount in which they exert a sensory effect.

[0028] Preferably, the weight ratio of the at least one compound of Formula 1 to the total amount of other flavorings ranges from 1:10 to 1:100. More preferably, the weight ratio of the at least one compound of Formula 1 to the total amount of other flavorings ranges from 1:600 ​​to 1:400.

[0029] In this context, it is preferred that the total amount of the at least one compound of formula 1 is in the range from 0.0001 to 99.9% by weight, preferably from 0.001 to 99.5% by weight, particularly preferably from 0.01 to 99% by weight, 0.01 to 90% by weight, 0.01 to 50% by weight, 0.01 to 20% by weight, 0.01 to 10% by weight and particularly preferably from 0.01 to 5% by weight, in particular 0.05 to 2% by weight, in each case based on the total weight of the composition.

[0030] In a preferred embodiment of the present invention, the compound of formula 1 is included in the fragrance composition in a sensory effective amount sufficient to modify an existing odor to be rounder, more natural, fuller, honeyed, stronger and / or more fruity, and / or to perfume, modify and / or enhance the fragrance composition to be less oily and / or less mushroomy.

[0031] Examples of fragrances which may be advantageously combined with the compounds of formula 1 in the context of the present invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. 1 and 2, Montclair, NJ 1969, self-published, or K. Bauer ei a / ., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.

[0032] Specific examples include: extracts from natural sources, such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, and the following specific examples: Ambergris tincture;Amyris oil;Angelica seed oil;Angelica root oil;Anise oil;Valerian oil;Basil oil;Tree moss absolute;Bay oil;Artemisia oil;Benzoin resin;Bergamot oil;Beeswax absolute;Birch tar oil;Bitter almond oil;Savory oil;Bucco leaf oil;Cabreuva oil;Cade oil;Calmus oil oil);Camphor oil;Cananga oil;Cardamom oil;Cascarilla oil;Cassia oil;Acacia absolute (Cassie-absolue);Castoreum absolute (Castoreum-absolue);Cedar leaf oil;Cedarwood oil;Cistus oil;Citronella oil;Citron oil;Copaiba balsam;Copaiba balsam oil;Coriander oil;Costus root oil;Cumin oil;Cypress oil;Davana oil;Dill herb oil;Dill seed oil;Bitter orange branch leaf absolute (Eau de brouts-Absolue);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;Garjan Balsam;Garjan Balsam Oil;Helichrysum Absolute;Helichrysum Oil;Ginger Oil;Iris Root Absolute;Iris Root Oil;Jasmine Absolute;Iris Oil;Blue Chamomile oil;Roman chamomile oil;Carrot seed oil;Cascarilla oil;Pine needle oil;Spearmint oil;Caraway oil;Labdanum oil;Labdanum absolute;Labdanum resin;Lavandine absolute;Lavandine oil;Lavender absolute;Lavender oil;Lemon grass oil;Lovage oil;Distilled lime oil;Pressed lime oil;Linaro oil;Limonium cubeba oil;Bay leaf oil;Mace oil;Marjoram oil;Mandarin oil;Massoir bark bark oil;Mimosa absolute;Musk grain 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 blossom absolute;Orange oil;Oregano oil;Palmarosa oil;Patchouli oil;Perilla oil;Balsam of Peru oil;Parsley leaf oil;Parsley seed oil;Petitgrain oil;Peppermint oil;Pepper oil;Allspice oil;Pine oil;Poley oil;Rose absolute;Rosewood oil;Rose oil;Rosemary oil;Dalmatian sage oil;Spanish sage oil;Sandalwood oil;Celery seed oil;Spicy lavender oil;Star anise oil;Styrax oil;Taget oil;Fern oil;Tea tree oil;Turpentine;Thyme oil;Tru balsam;Tonka absolute;Tuberose absolute;Vanilla extract;Violet leaf absolute;Verbena oil;Vetiver oil;Juniper berry oil;Wine yeast oil;Wormwood oil;Wintergreen oil;Ylang oil oil); hyssop oil; civet-absolue; cinnamon leaf oil; cinnamon bark oil and fractions thereof or constituents isolated therefrom;

[0033] Individual odorant molecules from the following groups: For example, 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane and other hydrocarbons; Aliphatic alcohols such as hexanol, octanol, 3-octanol, 2,6-dimethylheptanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, (E)-2-hexenol, 1-octen-3-ol, a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decen-5-ol, etc. Aliphatic aldehydes and their acetals, such as hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, 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, citronellyloxyacetaldehyde, 1-(1-methoxy-propoxy)-(E / Z)-3-hexene, etc. Aliphatic ketones and their oximes, such as 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 (οη), 6-methyl-5-hepten-2-one, etc. Aliphatic sulfur-containing compounds such as 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetylthiohexyl acetate, and 1-menthene-8-thiol; Aliphatic nitriles such as 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, and 3,7-dimethyl-6-octenoic acid nitrile; For example, (E)- and (Z)-3-hexenyl formate;Ethyl acetoacetate;Isoamyl 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;(E,Z)-Ethyl 2,4-decadienoate;Methyl 2-octinate;Methyl 2-nonynate 2-noninate); 2-isoamyloxyallyl acetate; 1-3,7-dimethyl-2,6-octadiene-oate; 4-methyl-2-pentyl crotonate and other aliphatic carboxylic acid esters; For example, geraniol; nerol; lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol; 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-dimethyloct-6-en-1-ol; (2E)-3,7-dimethylocta-2,6-dien-1-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol 2,6-dimethyl-2,5J-octatrien-1-ol; and acyclic terpene alcohols such as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglates and 3-methyl-2-butenoates; Acyclic terpene aldehydes and ketones such as citronellal, 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of geranial and neral. 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; guaiaol; and cyclic terpene alcohols such as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglates and 3-methyl-2-butenoates; For example, menthone; isomenthone; 8-mercaptomenthan-3-one (οη); carvone; camphor; fenchone; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethyl-ionone; alpha-irone; beta-damascenone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hex Sahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-one;2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal;Nootkatone;Dihydronootkatone;4,6,8-Megastigmatrien-3-one (οη);Alpha-sinensal;Beta-sinensal;Cyclic terpene aldehydes and ketones such as acetylated cedarwood oil (methyl cedryl ketone); Cyclic alcohols such as 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; 4-cyclohexylbutan-2-ol; For example, alpha,3,3-trimethylcyclohexylmethanol; 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; 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentane alicyclic alcohols such as 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 alicyclic ethers such as cineole; cedryl methyl ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclo-dodecane; alpha-cedrene epoxide; 3a,6,6,9a-tetramethyldodecahydro-naphtho[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-methylpropyl)-1,3-dioxane; For example, 4-tert.-butylcyclohexanone;2,2,5-trimethyl-5-pentylcyclopentanone;2-heptylcyclopentanone;2-pentylcyclopentanone;2-hydroxy-3-methyl-2-cyclopenten-1-one;3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one;3-methyl-2-pentyl-2-cyclopenten-1-one;3-methyl-4-cyclopentadecenone;3-methyl-5-cyclopentadecanone Cenone;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(οη);Cyclopentadecanone;Cyclohexadecanone and other cyclic and macrocyclic ketones; Alicyclic aldehydes such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde; Alicyclic ketones such as 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; 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-tetrahydroacetate esters of cyclic alcohols such as tetramethyl-2-naphthyl; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5,6-indenyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5,6-indenyl propionate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5,6-indenyl isobutyrate; 4,7-methanooctahydro-5,6-indenyl acetate; Esters of alicyclic alcohols, for example 1-cyclohexylethyl crotonate; Esters of alicyclic carboxylic acids such as, for example, allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, methyl ice- and trans-dihydrojasmonate, methyl ice- and trans-jasmonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate, and ethyl 2-methyl-1,3-dioxolane-2-acetate; Aromatic aliphatic alcohols such as benzyl alcohol, 2-phenylethanol, 1-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, etc. Esters of aromatic aliphatic 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, and 4-methoxybenzyl acetate; Aromatic aliphatic ethers such as 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl 1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine, 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine, etc.; e.g. benzaldehyde, phenylacetaldehyde, 3-phenylpropanal, hydratropaaldehyde, 4-methylbenzaldehyde aldehyde;4-Methylphenylacetaldehyde;3-(4-ethylphenyl)-2,2-dimethylpropanal;2-Methyl-3-(4-isopropylphenyl)propanal;2-Methyl-3-(4-isobutylphenyl)propanal;3-(4-tert.butyl-phenyl)propanal;Cinnamaldehyde;alpha-butylcinnamaldehyde;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 and other aromatic and araliphatic aldehydes; 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-benzofuranylethanone;(3-methyl-2-benzofuranyl)ethanone;Benzophenone;1,1,2,3,6-hexa Methyl-5-indanyl methyl ketone; 6-tert.butyl-1,1-di-methyl-4-indanyl methyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-aceto-naphthone and other aromatic and araliphatic ketones; Aromatic and aromatic aliphatic carboxylic acids and their esters, such as 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, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenylethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl 3-phenylglycidate, and ethyl 3-methyl-3-phenylglycidate; 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 (οη); 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one; 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; 1,16-hexadecanolide -nolide;9-Hexadecen-1,16-olide;10-Oxa-1,16-hexadecanolide;11-Oxa-1,16-hexa-decanolide;12-Oxa-1,16-hexadecanolide;1,12-Dodecanedioic acid ethylene;1,13-Tridecanedioic acid ethylene;2,3-Dihydrocoumarin;Octahydrocoumarin and other lactones;

[0034] In a further preferred embodiment of the present invention, the compound of formula 1 is preferably combined with one or more other fragrances having floral odor notes, particularly preferably 2, 3, 4, 5 or more.

[0035] Accordingly, the present invention also relates to perfume compositions comprising other perfumes that impart one, two, three, four, five or more floral odor notes.

[0036] The compounds used in the present invention advantageously achieve (at least in part) enhanced floral notes.

[0037] In a preferred embodiment of the present invention, the at least one additional fragrance is 4-cyclohexylbutan-2-ol (cyclohexylmagnol), 2-methyl-5-phenylpentan-1-ol (rosafen), 2-phenylethanol (phenylethylalkohol), 3-oxo-2-pentyl-1-cyclopentylacetat (Hedion), 1-( 4-isopropylcyclohexyl)-ethanol) (mugetanol), 3,7-dimethyloct-6-en-1-ol (citronellol), (2E)-3,7-dimethylocta-2,6-dien-1-ol (geraniol), 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol) and / or 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol (majantol) and / or benzyl 2-hydroxybenzoate (benzyl salicylate).

[0038] Preferably, 5,5-dimethyltetrahydrofuran-2-one is combined with one or more, particularly preferably 2, 3, 4, 5 or more, other preferred fragrances.

[0039] Perfume compositions (=perfume mixtures) containing at least one compound of formula 1 are advantageously used for perfuming in liquid form, undiluted or diluted with a solvent, suitable solvents for this are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropymyristate, etc.

[0040] Furthermore, the perfume composition according to the invention can be adsorbed on a carrier that ensures both a fine distribution of the perfume in the product and a controlled release during use. Such carriers can be porous inorganic materials such as light sulfates, silica gel, zeolites, gypsum, clay, clay granules, aerated concrete, or organic materials such as wood, cellulose-based materials, sugars, dextrins (e.g. maltodextrin), or plastics such as polyvinyl chloride, polyvinyl acetate or polyurethane. The combination of the composition according to the invention and the result obtained by the carrier material is also understood as the perfume composition according to the invention.

[0041] The perfume compositions according to the invention can also be microencapsulated, spray dried, for example as entrapped complexes or as moulded products, and added in this form to the product to be perfumed.

[0042] If necessary, the properties of the composition thus modified can be additionally optimized by so-called "coating" with suitable materials with a view to a more targeted release of the perfume, for which purpose waxy plastics such as polyvinyl alcohol are preferably used. The following resulting products represent the articles according to the invention.

[0043] A further aspect of the present invention relates to the use of the fragrance composition to modify an existing odor to be more rounded, more natural, more full-bodied, more honeyed, more intense and / or more fruity, and / or to perfume, modify and / or enhance a fragrance composition to be less oily and / or less mushroomy. The preferred embodiments already listed also apply to the use of the fragrance composition.

[0044] The perfume composition according to the invention can be advantageously used in concentrated form, liquid or modified form as described above for the manufacture of the perfumed articles according to the invention, For example (B.) Fragrance extracts, eau de parfum, eau de toilette, aftershaves, eau de colognes, pre-shave products, splash colognes and perfumed refreshing towels and acidic, alkaline and neutral cleaning agents such as floor cleaners, window cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, textile fresheners, ironing aids, liquid detergents, washing powders, laundry pre-treatment agents such as bleaches, soaking agents and stain removers, fabric softeners, laundry soaps, laundry tablets. air fresheners in the form of liquids, gels or applied to solid carriers, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe creams etc. and personal care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foam(s), bath oils etc., oil-in-water, water-in-oil and water-in-oil-in-water cosmetic emulsions such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions etc., hair care products such as hair sprays, hair gels, hair styling lotions, hair conditioners, permanent and semi-permanent hair dyes such as cold waves and hair straighteners. They can be used in hair styling products such as hair straighteners, hair lotions, hair creams and lotions, etc., deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, etc., in decorative cosmetics products such as eye shadows, nail polish, lipsticks, mascaras, etc., and in scenting candles, lamp oils, incense sticks, insecticides, repellents and fuels.

[0045] Of course, the fragrance compositions according to the invention can also be included in cosmetic or household compositions.

[0046] Another aspect of the present invention relates to a method for modifying an existing odor to make it fruitier, juicier, softer, clearer, fresher, sweeter and / or more floral, comprising the steps of: (a) at least one of formula 1 [ka] [In the formula, R 1 represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R 2 represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] The compound (b) comprising at least one additional flavoring; and (c) adding at least one compound of formula 1 to at least one additional fragrance in a sensory effective amount sufficient to modify the existing odor to be rounder, more natural, fuller, honeyed, stronger and / or more fruity, and / or to perfume, modify and / or enhance the fragrance composition to be less oily and / or less mushroomy,

[0047] Preferably, the weight ratio of the at least one compound of Formula 1 to the total amount of other flavorings ranges from 1:10 to 1:100. More preferably, the weight ratio of the at least one compound of Formula 1 to the total amount of other flavorings ranges from 1:600 ​​to 1:400.

[0048] In this context, it is preferred that the total amount of the at least one compound of formula 1 is in the range from 0.0001 to 99.9% by weight, preferably from 0.001 to 99.5% by weight, particularly preferably from 0.01 to 99% by weight, 0.01 to 90% by weight, 0.01 to 50% by weight, 0.01 to 20% by weight, 0.01 to 10% by weight and particularly preferably from 0.01 to 5% by weight, in particular 0.05 to 2% by weight, in each case based on the total weight of the composition.

[0049] In a preferred embodiment of the present invention, the at least one additional fragrance is 4-cyclohexylbutan-2-ol (cyclohexylmagnol), 2-methyl-5-phenylpentan-1-ol (rosafen), 2-phenylethanol (phenylethylalkohol), 3-oxo-2-pentyl-1-cyclopentylacetat (Hedion), 1-( 4-isopropylcyclohexyl)-ethanol) (mugetanol), 3,7-dimethyloct-6-en-1-ol (citronellol), (2E)-3,7-dimethylocta-2,6-dien-1-ol (geraniol), 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol) and / or 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol (majantol) and / or benzyl 2-hydroxybenzoate (benzyl salicylate).

[0050] Preferably, the compound of formula 1 is combined with one or more, particularly preferably 2, 3, 4, 5 or more, other preferred fragrance agents.

[0051] Preferably, 5,5-dimethyltetrahydrofuran-2-one is combined with one or more, particularly preferably 2, 3, 4, 5 or more, other preferred fragrances.

[0052] The further preferred embodiments already listed also apply to the method of the invention.

[0053] Another aspect of the present invention is a compound having at least one formula 1 [ka] [In the formula, R 1 represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R 2 represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] Compounds of; and The present invention relates to a perfumed product comprising two or more other fragrances and optionally other ingredients, characterized in that said product comprises at least one compound of formula 1 in an amount to modify the olfactory properties of said two or more other fragrances to be rounder, more natural, fuller, more honeyed, more intense and / or more fruity, and / or to perfume, modify and / or enhance the fragrance composition to be less oily and / or less mushroomy.

[0054] In a preferred embodiment the perfumed product is selected from cosmetics, hygiene and / or household products. The further preferred embodiments already listed also apply to the perfumed products of the invention.

[0055] Preferably, the perfumed household product is selected from the group consisting of detergents and cleaners, hygiene or care products, preferably in the field of body and hair care, cosmetics and household use, preferably selected from the group consisting of fragrance extracts, eau de parfum, eau de toilette, aftershave lotions, eau de cologne, preshave products, splash cologne, scented paper towels, acidic, alkaline or neutral cleaning agents, fabric deodorizing fresheners, iron care, liquid detergents, powder detergents, laundry pretreatment agents, fabric softeners, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, hair care products, makeup cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels. Most preferably, the perfumed product is selected from the group consisting of alcoholic fragrances, personal hygiene products or cleaning or care products for household use.

[0056] In addition, the perfumed products of the present invention preferably comprise at least one compound of formula 1 in a sensory-effective amount sufficient to provide the consumer with one or more olfactory characteristics selected from the group consisting of olfactory characteristics for perfuming, modifying, and / or enhancing the fragrance composition to be more rounded, more natural, more full-bodied, more honeyed, more intense and / or more fruity and / or less oily and / or less mushroomy.

[0057] It is also preferred that the total amount of compounds of formula 1, based on the total weight of the perfumed product, is in the range of 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight, particularly preferably 0.001 to 2% by weight, and even more preferably 0.1 to 2% by weight.

[0058] The abovementioned additives, auxiliaries and / or active substances are preferably not odorous substances. They can be, for example, preservatives, antimicrobials, chelating agents, detergents, emulsifiers, fats, etc. and in principle all substances which are used as additives, auxiliaries and / or active substances in cosmetic products, in particular in fragrance compositions as well as in household compositions.

[0059] The further preferred embodiments already listed also apply to the perfumed products according to the invention.

[0060] Hereinafter, the present invention will be further characterized on the basis of examples.

[0061] Example 1: Synthesis of 5,5-dimethyltetrahydrofuran-2-one

[0062] First manufacturing example

[0063] Under N2 atmosphere, methylmagnesium bromide (1.4 M in THF, 26.7 mL, 82.8 mmol) was slowly added to a solution of methyl 4-oxopentanoate (10.0 g, 76.8 mmol) in 50 ml of dry tetrahydrofuran (THF) at (m)-10 to 0 °C. After addition, the reaction temperature was raised to room temperature and maintained until the reaction was completed (~2 h). Saturated ammonium chloride solution was added to the reaction mixture, and the compound was extracted with methyl tert-butyl ether (MTBE) (50 mL x 3) and evaporated in a rotary evaporator (60 °C / 450-10 mbar) to obtain the crude product (7.2 g). Purification by Kugelrohr distillation (145 °C, 10.0 mbar) gave 6.6 g of the title compound. [ka]

[0064] Second manufacturing example a) Synthesis of 4-hydroxy-4-methyl-butyl pentanoate [ka] Radical reaction - A mixture of isopropanol (1950.5 g, 32.5 mol), butyl acrylate (208.0 g, 1.63 eq) and 2-tert-butylperoxy-2-methyl-propane (22.0 g, 0.2 mol) (DTBP) was heated under nitrogen at 10-20 bar between 155-160°C for 1 h in a 5 L autoclave. The crude product (2212 g) was distilled (Destbrücke) between 130-168°C to give the title compound (23.5 g). GC-MS:188,173,115,99,74,59,43,28 b) Synthesis of 5,5-dimethyltetrahydrofuran-2-one [ka] A mixture of 4-hydroxy-4-methyl-butyl pentanoate (23.0 g, ~100 mmol), methanol (50 mL) and 19 g of sodium hydroxide (32%, ~150 mmol) was refluxed for 2 h. The maximum amount of methanol was evaporated in a rotary evaporator (60 °C / 350-90 mbar) to give the crude product, which was added with 10% aqueous sulfuric acid (100 ml) and heated at 40 °C for 1 h. Sodium chloride was added at room temperature and the compound was extracted with MTBE (100 ml). The organic layer was dried over sodium sulfate and evaporated (50 °C, 400-70 mbar), followed by Kugelrohr distillation (100 °C, 15-5 mbar) to give 4.1 g of the title compound. 1H NMR (400MHz, CDCl3) δ2.62(t,J=8.2Hz,2H),2.06(t,J=8.2Hz,2H),1.43(s,6H). 13C NMR (101MHz, CDCl3) δ176.70,84.62,34.70,29.39,27.75,27.75. MS: 114, 99, 81, 70, 55, 43, 39, 28. Scent: Fruity, apricot, tonka bean, cherry leaf, creamy

[0065] Example 2: Synthesis of 5-ethyl-5-methyl-tetrahydrofuran-2-one

[0066] Synthesis of 4-methylhex-3-enenitrile (Step 1): [ka] A mixture of ammonium acetate (2.9g, 0.04mol), acetic acid (8.9g, 0.15mol), toluene (250mL), methyl-2-butanal (32.0g, 0.37mol) and 2-cyanoacetic acid 98%ig (42.0g, 0.49mol) was refluxed until the aldehyde was completely consumed (~8h). The reaction mixture was further maintained at 105-115°C for 1h to remove water and 5h to decarboxylate. The reaction mixture was then neutralized by washing with 5% sulfuric acid (50mL x 2) and evaporated to give the roh product (17,2g). Kugelrohr distillation (60°C, 0.5mbar) gave 4.6g of 4-methylhex-3-enenitrile E:Z nitrile mixture (7:3). 1H NMR(400MHz,C6D6)δ4.75(tdt,J=6.9,2.5,1.4Hz,1H),2.27-2.21(m,2H),1.67(qd,J=7.5,3.9Hz,2H),1.19-1.14(m,3H),0.74(mc,3H). 13C NMR(101MHz,C6D6)δ143.15,118.32,111.31,31.99,15.79,15.75,12.16. MS: 109, 94, 82, 67, 56, 41, 27 Scent: Herbal, lovage, almond, cinnamon, vegetable

[0067] ii) Synthesis of 5-ethyl-5-methyl-tetrahydrofuran-2-one A solution of 4-methylhex-3-enenitrile (2.0 g, 18.3 mmol) in toluene (10 mL) was added very slowly (30 min) to a mixture of concentrated sulfuric acid (2.7 mL) and water (2.7 mL) at 140°C and the reaction was maintained between 117-120°C until completion (~5 h). At room temperature, cold water (10 mL) was added, and the organic layer was washed with water until the pH of the aqueous layer was neutral and evaporated to give the crude product (0.9 g). Kugelrohr distillation (70°C, 0.76 mbar) gave 0.6 g of the title compound 5-ethyl-5-methyl-tetrahydrofuran-2-one. 1H NMR(400MHz,CDCl3)δ2.70-2.52(m,2H),2.15-2.03(m,1H),1.97(ddd,J=12.8,9.5,6.6Hz,1H),1.80-1.62(m,2H),1.38(s,3H),0.97(t,J=7.5Hz,3H). 13C NMR (101MHz, CDCl3) δ176.90,87.23,33.61,32.42,29.22,25.17,8.19. MS: 128, 113, 99, 84, 73, 86, 43, 27. Scent: Lactone, coconut, green

[0068] Example 3: Synthesis of 5,5-diethyltetrahydrofuran-2-one

[0069] Synthesis of 4-ethylhex-3-enenitrile – Step 1 [ka] A mixture of ammonium acetate (1.16 g, 15 mmol), acetic acid (2.17 mL, 38 mmol), toluene (100 mL), 2-ethylbutanal (10.2 g, 100 mmol) and 2-cyanoacetic acid 98% ig (9.36, 110 mmol) was refluxed and azeotropically distilled until the reaction was completely consumed. The reaction mixture was then neutralized by washing several timey with water and evaporated to give the roh product (7, 2 g). Kugelrohr distillation (65 °C, 0.5 mbar) gave 4.5 g of 4-ethylhex-3-enenitrile E:Z nitrile mixture (7:3). MS: 123, 108, 96, 81, 67, 55, 41, 27 1H NMR (400MHz, CDCl3) δ5.11(t,J=7.1Hz,1H),3.06(d,2H),2.12-2.00(m,4H),1.05-0.96(m,6H). 13C NMR(101MHz,CDCl3)δ149.62,118.89,109.86,28.90,23.54,15.86,12.58,12.25 Smell: mushroomy, almond, watery

[0070] ii) Synthesis of 5,5-diethyltetrahydrofuran-2-one - Step 2 A solution of 4-ethylhex-3-enenitrile (4.0 g, 32.5 mmol) in toluene (20 mL) was added very slowly (30 min) to a mixture of concentrated sulfuric acid (5.0 mL) and water (2.7 mL) at 140° C. The reaction was maintained between 128-135° C. until completion (~5 h). At room temperature, cold water (10 mL) was added, and the organic layer was washed with water until the pH of the aqueous layer was neutral and evaporated to give the crude product (2.7 g). Kugelrohr distillation (80° C., 0.9 mbar) gave 1.8 g of the title compound 5,5-diethyltetrahydrofuran-2-one. 1H NMR (400MHz, CDCl3) δ2.65-2.52(m,2H),2.01(dd,J=9.1,8.0Hz,2H),1.81-1.57(m,4H),0.94(t,J=7.5Hz,6H). 13C NMR (101MHz, CDCl3) δ177.12,89.63,30.87,30.87,29.82,29.23,7.80,7.80. MS:142,127,109,99,87,71,56,43,27 Smell: Lactonic, green, greasy, weak coconut

[0071] Example 4: Synthesis of 5-methyl-5-vinyl-tetrahydrofuran-2-one [ka] To a solution of methyl 4-oxopentanoate (44.5 g, 617.1 mmol) in 50 ml of dry THF, allylmagnesium bromide (1.0 M in diethyl ether (DEE), 100.0 mL, 99.8 mmol) was added slowly between -10 and 0°C. After the addition, the reaction temperature was raised to room temperature and maintained at room temperature until the reaction was complete (~3.5 h). Saturated ammonium chloride solution was added to the reaction mixture, and the compound was extracted with MTBE (60 mL x 3) and evaporated in a rotary evaporator (40°C / 450-10 mbar) to give the crude product (11.89 g). Purification by Kugelrohr distillation (90-115°C, 0.1 mbar) gave 6.9 g of the title compound. 1H NMR(400MHz,CDCl3)δ5.96-5.86(m,1H),5.34-5.26(m,1H),5.19-5.13(m,1H) ,2.63-2.52(m,2H),2.26-2.17(m,1H),2.14-2.04(m,1H),1.54-1.49(m,3H). 13C NMR(101MHz,CDCl3)δ176.68,140.01,113.73,85.41,33.82,28.74,26.29 MS: 126, 111, 99, 83, 67, 55, 43, 27. Scent: Mint, sweet, almond

[0072] Example 5: Synthesis of 5-allyl-5-methyl-tetrahydrofuran-2-one [ka] To a solution of methyl 4-oxopentanoate (12.0 g, 92.3 mmol) in 50 mL of dry THF, vinylmagnesium chloride (1.0 M in THF, 100.0 g, 99.0 mmol) was added slowly between -10 and 0 °C. After the addition, the reaction temperature was raised to room temperature and maintained at room temperature until the end of the reaction (~2 h). Saturated ammonium chloride solution was added to the reaction mixture, and the compound was extracted with MTBE (60 mL x 3) and evaporated in a rotary evaporator (40 °C / 450-10 mbar) to give the crude product (10.0 g). After purification by Kugelrohr distillation (70-130 °C, 0.1 mbar), 11.7 g of the title compound was obtained by column chromatography (cyclohexane / ethyl acetate, 20:1). 1H NMR(600MHz,CDCl3)δ5.79(ddt,J=16.9,10.3,7.3Hz,1H),5.18(ddt,J=10.3,2.0,1.0Hz ,1H),5.17(dq,J=17.0,1.9,1.4Hz,1H),2.62(ddd,J=18.0,9.5,7.6Hz,1H),2.57(ddd,J= 18.1,9.5,6.7Hz,1H),2.44(ddt,J=14.0,7.5,1.0Hz,1H),2.41(ddt,J=14.0,7.4,1.0Hz, 1H),2.16(ddd,J=12.9,9.5,7.6Hz,1H),1.96(ddd,J=13.0,9.6,6.8Hz,1H),1.40(s,3H). 13C NMR (151MHz, CDCl3) δ176.69,132.05,119.78,85.96,45.25,32.15,29.15,26.12. MS.140,125,107,99,71,55,43,39,27 Scent: Fresh, coconut, soft, natural

[0073] Example 6: Synthesis of 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one and 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one [ka]

[0074] Synthesis of 5-(2-hydroxy-2-methyl-propyl)-5-methyl-tetrahydrofuran-2-one: A mixture of 2-methyl-2,4-pentanediol (472.7 g, 4.0 mol) and a catalytic amount of aluminum isopropylate (250 g) was heated to 155° C. To this was added a previously prepared mixture of methyl acrylate (43.04 g, 0.50 mol), 2-methyl-2,4-pentanediol (118.18 g, 1.0 mol) and DTBP (7.32 g, 0.05 mol) very slowly over about 3 hours between 150-155° C. After addition, the product (23.4 g) (R at 0.1 mbar) which was carried on to the further step after first distilling off the alcohol, was obtained. T =110-150℃,H T =46-96℃).

[0075] Synthesis of 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one, 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one: A mixture of 5-(2-hydroxy-2-methyl-propyl)-5-methyl-tetrahydrofuran-2-one (23.4 g) and a catalytic amount of K-10 (2.3 g) was added to a Vigreux column (R T =152℃,H T = 148-150 ° C.) to obtain 17.6 g of the product 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one, 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one (1:3). 1 H NMR (600MHz, CDCl 3 ) δ5.39(m c ,1H),4.95(dd.J=1.5,2.2Hz,1H),4.79(dd.J=0.9,2.2Hz,1H),2.58(m c,4H),2.42(dd.J=13.9,0.9Hz,1H),2.37(dd.J=0.9,13.9Hz,1H),2.19(m c ,3H),1.94(ddd.J=6.3,9.4,12.9Hz,1H),1.81(dd.J=1.5,0.9Hz,3H),1.77(d,J=1.7Hz,3H),1.73(d,J=1.7Hz,3H),1.56(s,3H),1.39(s,3H). 13 C NMR (151 MHz, CDCl 3 )δ176.84,176.72,140.95,136.21,127.61,116.09,86.42,86.06,48.67,36.11,32.97,29.18,29.14,27.29,26.82,26.09,24.06,19.11. Scent: Tonka bean, coconut, tobacco

[0076] Example 7: Synthesis of 5-methyl-5-octyl-tetrahydrofuran-2-one [ka]

[0077] Synthesis of 4-methyldodec-3-enenitrile: A mixture of ammonium acetate (2.3 g, 0.03 mol), acetic acid (6.9 g, 6.6 mL, 0.11 mol), toluene (150 mL), 2-methyldecanal (75.0 g, 0.38 mol) and 2-cyanoacetic acid 98% ig (32.50 g, 0.38 mol) was refluxed until the aldehyde was completely consumed (~8 h). The reaction mixture was further maintained at 113-118 °C, water was removed over 1 h and decarboxylation was performed over 5 h. The reaction mixture was then neutralized by washing with 5% sulfuric acid (100 mL x 2) and evaporated to give the roh product (71.6 g). Kugelrohr distillation (121 °C, 0.7 mbar) gave 51 g of 4-methyldodec-3-enenitrile E:Z nitrile mixture (7:3). 1 H NMR (400 MHz, CDCl3 )δ5.15(tp,J=6.9,1.4Hz,2H),3.04(dq,J=7.0,1.0Hz,4H),2.06-1.98(m,4H),1.74(q,J=1.3 Hz,3H),1.66(d,J=1.4Hz,3H),1.45-1.31(m,4H),1.31-1.20(m,20H),0.88(t,J=6.8Hz,6H). 13 C NMR (101 MHz, CDCl 3 )δ142.84,142.74,118.71,118.67,111.91,111.28,39.23,31.93,31.88,31.89,31.87,29.53,29 .48,29.44,29.25,29.21,27.51,27.51,23.16,22.67,22.66,16.27,16.20,16.09,14.10,14.10. MS:193,178,164,150,136,122,109,96,81,70,56,41,29 Scent: Coriander

[0078] Synthesis of 5-methyl-5-octyl-tetrahydrofuran-2-one A solution of 4-methyldodec-3-enenitrile (20.0 g, 0.1 mol) in toluene (20 mL) was added very slowly (30 min) to a mixture of concentrated sulfuric acid (8.2 mL) and water (4.1 mL) at 140°C. The reaction was maintained between 130-135°C until completion (~5 h). At room temperature, cold water (10 mL) was added, and the organic layer was washed with water until the pH of the aqueous layer was neutral and evaporated to give the crude product (19.8 g). Kugelrohr distillation (130°C, 0.9 mbar) gave 17.2 g of the title compound 5-methyl-5-octyl-tetrahydrofuran-2-one. 1 H NMR (400 MHz, CDCl 3 )δ2.68-2.51(m,2H),2.13-2.04(m,1H),2.02-1.92(m,1H),1.73-1.58(m,2H),1.38(s,3H),1.38-1.17(m,12H),0.88(t,3H). 13C NMR (101 MHz, CDCl 3 )δ176.89,86.99,41.02,32.95,31.84,29.85,29.46,29.21,29.21,25.66,23.86,22.65,14.10. GC / MS(EI):212,197,179,114,99,83,71,55,43 Odor: Weak lactone and greasy

[0079] Example 8: Synthesis of 5-methyl-5-nonyl-tetrahydrofuran-2-one [ka]

[0080] Synthesis of (E / Z) 4-Methyltridec-3-enenitrile A mixture of ammonium acetate (2.3 g, 0.03 mol), acetic acid (6.9 g, 6.6 mL, 0.11 mol), toluene (150 mL), 2-methylundecanal (70.0 g, 0.38 mol) and 2-cyanoacetic acid 98% ig (32.50 g, 0.38 mol) was refluxed until the aldehyde was completely consumed (~8 h). The reaction mixture was further maintained at 113-118 °C, water was removed over 1 h and decarboxylation was performed over 5 h. The reaction mixture was then neutralized by washing with 5% sulfuric acid (100 mL x 2) and evaporated to give the roh product (61.9 g). Kugelrohr distillation (128 °C, 0.7 mbar) gave 42.6 g of E:Z nitrile mixture (2:1) of 4-methyltridec-3-enenitrile. 1 H NMR (400 MHz, CDCl 3 )δ5.15(ddq,J=6.9,5.6,1.4Hz,2H),3.04(dq,J=7.0,0.9Hz,4H),2.02(dd,J=8.8,6.7Hz,4H),1.74 (q,J=1.3Hz,3H),1.66(q,J=1.0Hz,3H),1.48-1.35(m,4H),1.34-1.20(m,24H),0.94-0.83(m,6H). 13 C NMR (101 MHz, CDCl 3 )δ142.84,142.75,118.71,118.61,111.91,111.28,39.24,31.94,31.90,31.88,29.55,29.53,29 .48,29.36,29.32,29.31,29.21,27.52,23.16,22.68,22.68,16.27,16.20,16.09,14.11,14.11. MS:207,192,178,164,150,136,112,96,83,70,55,43,29. Smell: Orange, nitrile, greasy

[0081] Synthesis of 5-methyl-5-nonyl-tetrahydrofuran-2-one A solution of 4-methyltridec-3-enenitrile (20.0 g, 0.1 mol) in toluene (20 mL) was added very slowly (30 min) to a mixture of concentrated sulfuric acid (8.2 mL) and water (4.1 mL) at 140°C. The reaction was maintained between 130-135°C until completion (~5 h). At room temperature, cold water (10 mL) was added, and the organic layer was washed with water until the pH of the aqueous layer was neutral and evaporated to give the crude product (19.3 g). Kugelrohr distillation (130°C, 0.9 mbar) gave 17.6 g of the title compound 5-methyl-5-nonyl-tetrahydrofuran-2-one. 1 H NMR(400MHz,CDCl3)δ2.69-2.50(m,2H),2.09(ddd,J=12.9,9.3,8.0Hz,1H),1.97(ddd,J=12 .8,9.4,6.6Hz,1H),1.70-1.57(m,2H),1.38(s,3H),1.36-1.19(m,14H),0.94-0.82(m,3H). 13 C NMR(101MHz,CDCl3)δ176.88,86.98,41.02,32.95,31.87,29.85,29.53,29.51,29.29,29.21,25.66,23.86,22.68,14.11. MS:226,211,193,171,151,127,114,99,83,71,55,43,29. Scent: Weak lactone type

[0082] Example 9: Synthesis of 5-butyl-5-ethyl-tetrahydrofuran-2-one [ka]

[0083] (E / Z) Synthesis of 4-ethyloct-3-enenitrile: Prepared according to WO2018192665 1 H NMR (400 MHz, CDCl 3 )δ5.17-5.08(m,2H),3.07(s,4H),2.13-1.97(m,8H),1.35(s,8H),1.01(t,J= 7.4Hz,3H),1.00(t,J=7.6Hz,3H),0.92(t,J=7.1Hz,3H),0.91(t,J=7.2Hz,3H) 13 C NMR (101 MHz, CDCl 3 )δ148.29,148.21,118.87,118.85,110.81,110.41,35.87,30.27,30.13,29 .89,29.31,23.35,22.77,22.41,16.05,15.88,13.94,13.94,12.56,12.30. Scent: Rose, green, nitrile, iris, carrot, dry

[0084] Synthesis of 5-butyl-5-ethyl-tetrahydrofuran-2-one A solution of concentrated sulfuric acid (75.0 g) in water (25.5 g) was heated to 140°C. To this, 4-ethyl-oct-3-enenitrile (reference: Symrise AG; WO2018192665) (100.0 g, 0.66 mol) was added very slowly over about 1 hour (very strong exotherm) and the reaction was maintained between 130-135°C for 2 hours. At room temperature, the reaction mixture was poured into cold water, neutralized and evaporated to give a crude product (99.8 g). After purification with spaltrohr, 77.6 g of product was obtained by kugelrohr distillation. MS: 141, 113, 95, 81, 69, 57, 41 1 H NMR (400 MHz, CDCl 3 )δ2.58(dd,J=9.1,8.0Hz,2H),2.02(dd,J=9.1,8.0Hz,2H),1.77-1.66(m,2H ),1.68-1.60(m,2H),1.41-1.24(m,4H),0.94(t,J=7.4Hz,3H),0.91(t,3H). 13 C NMR (101 MHz, CDCl 3 )δ171,10,89.41,38.00,31.34,30.33,29.22,25.57,22.99,13.97,7.86. Scent: coconut, lactone, fruity

[0085] Example 10: Synthesis of 5-butyl-5-ethyl-furan-2-one [ka]

[0086] Synthesis of 4-ethylocta-3,5-dienenitrile A mixture of ammonium acetate (4.7g, 0.06mol), acetic acid (13.8g, 0.23mol), toluene (300g), 2-ethylhexyl-2-enal (100g, 0.75mol) and 2-cyanoacetic acid 98%ig (64.50g, 0.76mol) was refluxed until the aldehyde was completely consumed (~8h). The reaction mixture was further maintained at 113-118°C, water was removed for 1h and decarboxylation was carried out for 5h. The reaction mixture was then neutralized by washing with 5% sulfuric acid (100mL x 2) and evaporated to give the roh product (113.8g). Kugelrohr distillation (60-90°C, 0.5mbar) gave 59g of the title compound as an E:Z nitrile mixture (7:3). 1 H NMR (400 MHz, CDCl 3 )δ5.92(d,J=15.9Hz,1H),5.85-5.79(m,1H),5.26(t,J=7.2Hz,1H),3.15( d,J=7.2Hz,2H),2.31-2.17(m,2H),2.17-2.07(m,2H),1.13-0.98(m,6H). 13 C NMR (101 MHz, CDCl 3 )δ145.40,132.73,130.07,118.29,114.53,25.87,20.21,16.11,13.61,13.28. MS: 149, 134, 120, 10 Scent: Green, cucumber, soapy, nitrile

[0087] Synthesis of 5-butyl-5-ethyl-furan-2-one A solution of concentrated sulfuric acid (7.5 g) in water (2.6 g) was heated to 140° C. To this was added 4-ethyl-octa-3,5-dienenitrile (7.5 g, 0.07 mol) very slowly over about 30 minutes (very strong exotherm) and the reaction was maintained between 130-135° C. for 2 hours. The reaction mixture was poured into cold water at room temperature, neutralized and evaporated to give the crude product (1.7 g). Purification by Kugelrohr distillation (105° C., 0.8 mbar) gave 0.6 g of product. MS: 168, 139, 113, 95, 67, 57, 41, 29 GC-Sniff: Pungent odor, peculiar odor, dusty

[0088] Example 11: Expression of preferred perfume odor after addition of 4-cyclohexylbutan-2-one The odor evaluation and description was performed by an expert panel. [Table 3] [Table 4]

Claims

1. At least one of formula 1 【Chemistry 1】 [In the formula, R １ represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R ２ represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] Use of the compound as a fragrance.

2. The R １ represents methyl, ethyl, butyl, vinyl, allyl, 2-methylprop-1-enyl, 2-methylallyl, octyl or nonyl; and R ２ 2. The use according to claim 1, wherein represents methyl or ethyl.

3. 3. The use according to claim 1 and / or 2, wherein the compound of formula 1 is selected from the group consisting of 5,5-dimethyltetrahydrofuran-2-one, 5-ethyl-5-methyl-tetrahydrofuran-2-one, 5,5-diethyltetrahydrofuran-2-one, 5-methyl-5-vinyl-tetrahydrofuran-2-one, 5-allyl-5-methyl-tetrahydrofuran-2-one, 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one, 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one, 5-methyl-5-octyl-tetrahydrofuran-2-one, 5-methyl-5-nonyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-furan-2-one.

4. The use according to claim 1 and / or 2, wherein the compound of formula 1 is 5,5-dimethyltetrahydrofuran-2-one.

5. Use according to claims 1 to 4 in a fragrance composition to obtain at least one of the following aroma notes: fruity, apricot, cherry leaf, creamy, coconut, green, mint, sweet, almond, fresh, soft, natural, tonka bean, tobacco, hay.

6. Use according to claims 1 to 5 for perfuming, modifying and / or enhancing a fragrance composition to be rounder, more natural, fuller, honey-like, stronger and / or more fruity and / or for perfuming, modifying and / or enhancing a fragrance composition to be less oily and / or less mushroomy.

7. At least one of formula 1 【Chemistry 2】 [In the formula, R １ represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R ２ represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] and A fragrance composition comprising or consisting of at least one additional fragrance.

8. 9. The fragrance composition according to claim 8, wherein the compound of formula 1 is selected from the group consisting of 5,5-dimethyltetrahydrofuran-2-one, 5-ethyl-5-methyl-tetrahydrofuran-2-one, 5,5-diethyltetrahydrofuran-2-one, 5-methyl-5-vinyl-tetrahydrofuran-2-one, 5-allyl-5-methyl-tetrahydrofuran-2-one, 5-methyl-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one, 5-methyl-5-(2-methylallyl)tetrahydrofuran-2-one, 5-methyl-5-octyl-tetrahydrofuran-2-one, 5-methyl-5-nonyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-tetrahydrofuran-2-one, 5-butyl-5-ethyl-furan-2-one.

9. 9. The fragrance composition according to claim 7, wherein the weight ratio of said at least one compound of formula 1 to the total amount of other fragrances ranges from 1:10 to 1:

100.

10. 10. The fragrance composition according to claim 9, wherein the weight ratio of said at least one compound of Formula 1 to the total amount of other fragrances ranges from 1:600 ​​to 1:

400.

11. A fragrance composition according to claims 7 to 10, wherein the amount of said at least one compound of formula 1 ranges from 0.01 to 5% by weight, based on the total weight of the fragrance composition.

12. 12. The fragrance composition according to at least one of claims 7 to 11, wherein the at least one compound of formula 1 is present in the fragrance composition in a sensory effective amount sufficient to modify an existing odor to be rounder, more natural, fuller, honey-like, stronger and / or more fruity, and / or to perfume, modify and / or enhance the fragrance composition to be less oily and / or less mushroomy.

13. 13. The fragrance composition according to claim 7, wherein the at least one additional fragrance is selected from the group consisting of 4-cyclohexylbutan-2-ol (cyclohexylmagnol), 2-methyl-5-phenylpentan-1-ol (rosaphen), 2-phenylethanol (phenylethyl alcohol), 3-oxo-2-pentyl-1-cyclopentyl methyl acetate (hedion), 1-(4-isopropylcyclohexyl)-ethanol) (mugetanol), 3,7-dimethyloct-6-en-1-ol (citronellol), (2E)-3,7-dimethylocta-2,6-dien-1-ol (geraniol), 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol) and / or 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol (majantol), benzyl 2-hydroxybenzoate (benzyl salicylate).

14. Use of a fragrance composition according to any one of claims 7 to 13 for modifying an existing aroma to be more mellow, more natural, more full-bodied, more honey-like, more intense and / or more fruity, and / or for perfumery, modifying and / or enhancing a fragrance composition to be less oily and / or less mushroomy.

15. At least one of formula 1 【Chemistry 3】 [In the formula, R １ represents H, methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, vinyl, allyl, 2-methylprop-1-enyl or 2-methylallyl; R ２ represents H, methyl or ethyl; and The dotted lines represent carbon-carbon single or double bonds.] and 1. A perfumed product comprising two or more other fragrances and optionally other ingredients, characterized in that the product comprises at least one compound of formula 1 in an amount that modifies the olfactory properties of the two or more other fragrances to be more rounded, more natural, more full-bodied, more honeyed, more intense and / or more fruity, and / or that perfumes, modifies and / or enhances the fragrance composition to be less oily and / or less mushroomy.

Images