Use of cyclic and linear pentyl- and hexyl-2-methylbenzoic acid esters as fragrances

Abstract

The invention relates to the use of a compound of formula (I) as a fragrance, in fragrance compositions and perfumed articles.

Description

Use of cyclic and linear pentyl and hexyl 2-methylbenzoic acid esters as fragrances AREA OF INVENTION

[0001] The present invention is in the field of fragrances and relates to the use of a small, selected group of known 2-methylbenzoic acid esters as novel fragrances to replace salicylates. Furthermore, the present invention relates to a method for conveying, modifying, and / or enhancing certain odor notes and / or odor effects. BACKGROUND OF THE INVENTION

[0002] To set trends in the perfume industry, new fragrances are constantly needed. Therefore, perfumers and fragrance chemists are continually searching for new compounds with signature effects. Furthermore, more and more traditional, long-established compounds that have proven to be toxicologically problematic over time must be replaced, especially those known or suspected to have carcinogenic, mutagenic, or reprotoxic properties.

[0003] This group now also includes the class of compounds known as salicylates, which are historically derived from drugs such as Aspirin®. Favored by the resulting inexpensive access to salicylic acid, a whole range of salicylic acid esters found their way into the perfumery and fragrance industry, especially the methyl, butyl, amyl, hexyl, benzyl, and 3-hexenyl esters (F. Elterlein, N. Bugdhan, P. Kraft, Sniffing Out the Sustainable Future: The Renewability Revolution in Fragrance Chemistry, Chem. Eur. J. 2024, e202400006). These cover a wide spectrum of different scent notes and / or olfactory effects, from balsamic to green-floral, through solar-floral to other flowers such as orchid, hyacinth, rose, mignonette, and lilac. All salicylates, however, share a certain white-floral, ylang-ylang character and a slightly medicinal quality. It has a characteristic winter gin note, most pronounced in methyl salicylate, one of the characteristic components of winter gin OI.

[0004] To replace the salicylates, which are suspected of being toxicologically harmful, attempts have so far been made, due to a lack of suitable substitutes, to replace only the common wintergreen-ylang-ylang character and to introduce the various floral characteristics into the composition via other fragrance components. For this purpose, the IFF introduced 'Ylanganate' (methyl o-toluate, CAS 89-71-4) last year (AT Levorse, RA Weiss, M. Pawlak, IFF, US Pat. Appl. US 2005 / 0170998 A1, January 29, 2004), which has a white floral scent reminiscent of orange blossoms, ylang-ylang, and gardenias.

[0005] Although ylang-anate, like methyl salicylate, is a methyl ester, the methyl salicylate note is surprisingly more pronounced in the corresponding ethyl benzoate (ethyl 2-methyl benzoate), the ethyl ester recently introduced into perfumery (B. Holscher, M. Mansfeld, L.-J. Kleine-Benne, T. Belmas, Symrise, PCT Int. Pat. Appl. WO 2023 / 232237 A1, May 31, 2022). The effects cannot therefore be transferred from salicylates to carba-analogous benzoates, presumably because the electronegative phenolic hydroxyl group is absent, and one quickly slips into benzoate notes. It is therefore not a recipe, but the compounds are still chemically benzoates, which is reflected not only in the toxicologically beneficial properties, but also in the odor profile.

[0006] While notes in the direction of wintergreen and ylang-ylang can be satisfactorily represented with 'ylanganate' and ethyl-2-methylbenzoate, this is not the case for the vast majority of salicylate notes, especially in the area of ​​green-balsamic scent notes and / or scent effects.

[0007] In particular, it has become apparent that the various salicylates, and especially those of the green-balsamic family, cannot simply be replaced by adding a methyl salicylate-like substitute such as 'ylanganate' and ethyl 2-methyl benzoate. to imitate a single fragrance ingredient or fragrance complex, because methyl and ethyl 2-methyl benzoate are too harsh and medicinal in character, standing out too clearly, which severely limits their use in alcoholic fine perfumery. DESCRIPTION BY INVENTION

[0008] Therefore, the object of the present invention is to overcome these disadvantages of the prior art.

[0009] Furthermore, it is an object of the present invention to provide new odorants capable of improving the positive and advantageous odor aspects of other odorants and / or (simultaneously) reducing, inhibiting, and / or masking undesirable, unpleasant odor aspects. In particular, the new odorant should also be characterized by improving the stability, solubility, and overall performance of other odorants and reducing the required dosage. Finally, the odorant mixtures themselves should exhibit excellent biodegradability and be harmless to humans and the environment.

[0010] According to the invention, this is achieved by the subject matter of the present patent claims. A first embodiment of the invention relates to a compound of formula (I) as a fragrance. Single binding corresponds to (Formula 1) Preferred compounds are pentyl-2-methyl benzoate (PMB), hexyl-2-methyl benzoate (HMB), cyclopentyl-2-methyl benzoate (CPMB), and cyclohexyl-2-methyl benzoate (CH-MB). PMB is particularly preferred.

[0011] The suitability of the compounds of formula (I) as odorants was previously unknown. Likewise, no descriptions of their odors are available. For example, cyclohexyl-2-methylbenzoate was described as a solubilizer for organic compounds in photoprotective compositions (ISP INVESTMENTS - US10328003 B2, 2019). This publication explicitly emphasizes the avoidance of odor from both the substance and the resulting compositions. The addition of other odorants is not described.

[0012] Cyclohexyl-2-methylbenzoate also appears as a residue but not as a single substance in isothiazole carboxamides claimed as plant protection products in US 6310005 B1 (Bayer AG, 2001), and applications for the cyclopentyl derivative in the field of optical storage media are also described only as a residue and not as a single substance (CIBA Specialities Chemistry, US 2005 / 0238840 A1, 2005), as well as in connection with the control of the rice weevil Sitophilus oryzae L. (AV Remesh, CSV Babu, Natural Product Research, 2023, 37, 2748-2752). As for the open-chain linear C5 and Ce esters, these have been described for the cosmetic treatment of keratin stability in the field of hair care products (Henkel KGaA - W02020 / 200545, 2020), as well as in the field of lithography (Shin Etsu Chemical US2022 / 127225 A1, 2022).

[0013] The inventors of the present application have therefore made the surprising discovery that the compounds of formula (I) are suitable as fragrances and possess a characteristic salicylate-like odor profile in the direction of green-balsamic. Furthermore, the compounds of formula (I), as substituted benzoates, are toxicologically harmless. Surprisingly, it has also been shown that the compounds of formula (I) differ significantly in their odor from other methyl benzoates, such as the perfumery-introduced ylanganate (methyl 2-methyl benzoate) and ethyl 2-methyl benzoate, by exhibiting much weaker or even completely absent medical and technical properties, according to Wintergruin. These compounds differ in that they are replaced by green-balsamic or floral notes, which even possess more or less pronounced cyclamen-like effects, whereby the compounds according to the invention surpass the two known salicylate substitutes in their applicability. These notes, perceived as medicinal and technical, severely restrict the use of ylang-anate (methyl 2-methyl benzoate) and ethyl 2-methyl benzoate in fine perfumery.

[0014] The fact that the compounds of formula (I) to be used according to the invention can convey a very complex and diverse overall sensory impression, which can otherwise usually only be achieved by mixtures of several components (e.g. essential oils or spice mixtures), is also particularly surprising.

[0015] Beyond their primary, namely olfactory, properties, the compounds of formula (I) also possess additional positive secondary properties, in particular they lead to higher transparency compared to fragrances with similar olfactory properties, as well as better stability than salicylates in more aggressive media and preparations.

[0016] As already mentioned, the compounds of formula (I) can be used in a variety of products; they can be used as individual fragrances, but can also be combined particularly advantageously with other fragrances in varying proportions to form fragrance mixtures, thereby creating novel and original perfume compositions. Accordingly, one aspect of the invention also relates to a fragrance mixture and optionally further components (solvents or the like) which contain one or more compounds of formula (I).

[0017] The fragrance mixture according to the invention comprises or consists of at least one compound of formula (I) single bond corresponds to and at least one fragrance ingredient that does not correspond to formula (I).

[0018] Compounds of formula (I') are preferred Formula (I')

[0019] Preferably, the odorant mixture according to the invention comprises or consists of at least one compound of formula (I) and two or more further odorants that do not correspond to formula (I). Particularly preferably, the odorant mixture according to the invention comprises or consists of at least one compound of formula (I) and three or more further odorants that do not correspond to formula (I). Most preferably, the odorant mixture according to the invention comprises or consists of at least one compound of formula (I) and four or more further odorants that do not correspond to formula (I).

[0020] Fragrance mixtures comprising two or more compounds of formula (I) as well as other fragrances not corresponding to formula (I) are also advantageous.

[0021] The compounds of formula (I) are usually used in a sensorily effective amount, i.e., in a total amount in which they exert a sensory effect. Preferably, the weight ratio of the total amount of compounds of formula (I) to the total amount of other odorants is in the range of 1:1000 to 1:10, more preferably in the range of 1:1000 to 1:100.

[0022] In this context, it is preferred if the total amount of compounds of formula (I) is in the range of 0.0001 to 99.9 wt.%, preferably 0.001 to 99.5 wt.%, particularly preferably 0.01 to 25 wt.%, or from 0.01 to 20 wt.%, from 0.01 to 10 wt.% and particularly preferably from 0.01 to 8 wt.%, in particular from 0.01 to 4 wt.% and also 0.01 to 1.5 wt.%, in each case based on the total weight of the composition.

[0023] Examples of fragrances that can be advantageously combined with the compounds of formula (I) within the scope of the present invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published, or Common Fragrance and Flavor Materials: Preparation, Properties and Uses, by H. Surburg and Johannes Panten (Ed.), 6th edition, Wiley-VCH, Weinheim, 2016.

[0024] Specifically mentioned are, for example, essential oils and extracts such as field mint, amyrisol, angelica root oil, apricot seed oil, basil oil, bayol, mugwort oil, benzoin resinoid, bergamot oil, beaver holly absolute, beeswax absolute, cabreuvabl, canangal, cassia absolute, cistus oil, citronellol, copaiba balsam oil, cypress oil, cypriol oil, davanabl, dill oil, oakmoss absolute, elemi oil / resinoid, tarragon oil, eucalyptus oil, fennel oil, spruce needle oil, fucus absolute, galbanum oil, geranium oil, grapefruit oil, guaiac wood oil, gurjun balsam oil, hay absolute, hydrocarboresin B, immortelle absolute, ginger extract / oil, jasmine absolute, jasmine absolute sambac. Chamomile leaf, Blue chamomile leaf, Cardamom leaf / abs., Carrot seed leaf, Pine needle leaf, Coriander seed leaf, Spearmint leaf, Pineapple leaf, Labdanum absolute / resinoid, Lavandin leaf, Lavender leaf, Lovage root leaf, Lime leaf Lime blossom terpenes, Litsea cubeba oil, Longoza bliite blossom, Bay leaf blossom, Magnolia leaf blossom, Magnolia blossom blossom, Mandarin blossom, Marjoram blossom, Mastic absolute Mimosa Absolute, Musk Seed Absolute, Nutmeg Flower Leaf, Clary Sage Oil, Nutmeg Leaf, Myrrh Leaf, Myrtle Leaf, Daffodil Absolute, Clove Leaf Leaf, Clove Flower Leaf, Neroli Leaf, Olibanum Leaf, Opoponax Leaf / Resinoid, Orange Flower Absolute, Orange Leaf, Origanum Leaf, Osmanthus Absolute, Palmarosa Leaf, Patchouli Leaf, Parsley Leaf Leaf, Parsley Seed Leaf, Perilla Leaf, Peruvian Balsam Leaf, Petitgrain Leaf, Petitgrain Absolute, Peppermint Leaf, Pepper Leaf (Black, Green, Pink), Allspice Leaf, Rose Absolute, Rose Leaf, Rosemary Leaf, Rum CO2 Extract, Dalmatian Sage Oil, Spanish Sage Oil, Sandalwood Leaf, Celery Seed Leaf, Spike Leaf, Star Anise Leaf, Styrax Leaf, Marigold Leaf, Tea Tree Leaf, Turpentine Leaf Thujabl, Thymebl, Tonka Bean Absolute, Tuberose Absolute, Vanilla Absolute, Violet Leaf Concrete / Absolute, Vetiverbl, Juniper Berry Bl, Wormwood Bl, Ylang-Ylang OI, Cedarwood Bl, Cedarwood Bl Atlas, Cinnamon Leaf Bl, Cinnamon Bark Bl, Lemongrass Bl, Lemon Bl, Lemon Bl terpenes, and isolated constituents and fractions thereof;

[0025] Alkohole, wie beispielsweise 1 -(2-tert-Butylcyclohexyl)oxybutan-2-ol (139504-68-0; Ambercore); 2,6-di-tert-Butyl-p-cresol (128-37-0; BHT Ionol); (Z)-3- Methyl-5-(2,2,3-trimethyl-1 -cyclopent-3-enyl)pent-4-en-2-ol (67801 -20-1; Ebanol); 4- Methyl-2-(2-methylpropyl)oxan-4-ol (63500-71 -0; Florosa / Pyranol); [(1 / ?*,2S*)-1 - Methyl-2-[[(1 R*,3S*,5S*)-1,2,2-trimethyl-3- bicyclo[3.1.0]hexanyl]methyl]cyclopropyl]methanol (198404-98-7; Javanol); (3 / ?*)-1 - [(1 / ?*,6S*)-2,2,6-Trimethylcyclohexyl]hexan-3-ol; (3S)-1 -[(1 / ?,6S)-2,2,6- trimethylcyclohexyl]hexan-3-ol (70788-30-6; Norlimbanol); 3-Methyl-5- phenylpentan-1 -ol (55066-48-3; Phenoxanol); (£)-3,3-Dimethyl-5-(2,2,3-trimethyl-3- cyclopenten-1 -yl)-4-penten-2-ol (107898-54-4; Polysantol); 5-(3- methylphenyl)pentan-1 -ol (25634-93-9; Rosaphen); 3-Methyl-5-(2,2,3- trimethylcyclopent-3-en-1 -yl)pentan-2-ol (1471313-03-7; 65113-99-7; Sandalore); (2£)-2-Ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1 -yl)-buten-1 -ol + 2- Ethyl -4-(2,2,3 - Trimethyl-3-cyclopenten-1 -yl)-2-buten-1 -ol (106185-75-5; 28219-61 -6; Sandranol); (£)-4-Methyldec-3-en-5-ol (81782-77-6; Undecavertol); 3-[5,5,6- Trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1 -ol (70955-71 -4; Sandela); Hexan-1 -ol; Octan-1 -ol; Decan-1 -ol; Dodecan-1 -ol; Borneol; Isoborneol; Citronellol; / .-Citronellol; Dihydroeugenol; Dihydromyrcenol; Dimethyl Benzyl Carbinol; Ethyllinalool; Eugenol; Geraniol; czs-3-Hexenol; Isobornylcyclohexanol; Linalool; Nerolidol; Phenylethylalkohol; Phenylethyl Dimethyl Carbinol; Phenylpropylalkohol; Propenyl Guaethol; Sulfurol; alpha-Terpineol; Tetrahydrolinalool; Thymol;

[0026] Aldehyde, wie beispielsweise 2,6,10-Trimethylundec-9-enal (141 -13-9; Adoxal; Farenal); alpha-,3,3-Trimethyl-cyclohexanemethanolformat (25225-08-5; Aphermat); 4-(1,1 -Dimethylethyl)phenylpropanal (18127-01 -0; Bourgeonal); 6- Methoxy-2,6-dimethyloctanal (929253-05-4; Calypson); 4-Methoxy-alpha- methylphenylpropanal (5462-06-6; Canthoxal); a, 2,2,6- tetramethylcyclohexenebutanal (65405-84-7; Cetonal); 8,8-Dimethyl-1,2,3,4,5,6,7,8- octahydro-2-naphthaldehyd + 1,2,3,4,5,6,7,8-Octahydro-5,5-dimethyl-2- naphthalenecarboxaldehyd (68991 -96-8; 68991 -97-9; Cyclomyral); 4-(octahydro-4,7- methano-5H-inden-5-ylidenbutanal (30168-23-1; Dupical); 4,8-Dimethyl-4,9- decadienal (71077-31 -1; Floral Super); 3-(4-Ethylphenyl)-2,2-dimethylpropanal + 3- (2-Ethylphenyl)-2,2-dimethylpropanal (67634-15-5; 67634-14-4; Florazon); beta- Methyl-3-(1 -methylethyl)benzenepropanal (12509-85-5; Florhydral); Methylenedioxyphenylmethylpropanal (1205-17-0; Helional); a, 4- Dimethylbenzenepropanal (41496-43-9; Jasmorange, Satinaldehyd); (Z,£)-2,4- Dimethylcyclohex-3-ene-1 -carbaldehyd (68039-49-6; 68737-61 -1; Ligustral, Tripalal, Cyclal C, Vertocitral) ; 3-(4'-tert-Butylphenyl)butanal (80-54-6; Lilial); (1 / ?)-p,4- Dimethyl-3-cyclohexene-1 -propanal (199445-85-7; Liminal); (4R)-4-(1 -Methylethyl)-1 - cyclohexene-1 -propanal (1378867-81 -2; Lilybelle); (4S)-4-(1 -Methylethyl)-1 - cyclohexene-1 -propanal (1378867-82-3; Lilybelle Isomer); 4-(4-Hydroxy-4-methyl- pentyl)-3-cyclohexen-1 -carboxyaldehyd (130066-44-3; Lyral); 6-Methyl-1 -8-yl- methylethyl-bicyclo[2.2.2]oct-5-ene-2-carboxaldehyd (67845-30-1; Maceal); (±)-2,6- Dimethyl-5-heptenal (106-72-9; Melonal); (E)-2,6,10-Trimethylundeca-5,9-dienal (54082-68-7; Oncidal); 6,6-Dimethyl-2-norpinene-2-propionaldehyd (33885-51 -7; Pinoacetaldehyd); 1 -Methyl-4-(4-methyl-3-pentenyl)cyclohex-3-ene-1 -carboxaldehyd + 6,6-Dimethyl-2-norpinene-2-propionaldehyd (119652-81 -2; 52475-86-2;. Precyclemon B); 3-Phenylbutanal (16251 -77-7; Trifernal); Octahydro-5-methoxy-4,7- methano-1 H-indene-2-carboxaldehyd (86803-90-9; Scentenal); rel- (3a / ?,4 / ?,5 / ?,7 / ?,7a / ?)-Octahydro-4,7-methano-1H-indene-5-carboxaldehyde (145374- 28-3; Vertral); 4-(4'-Methylpent-3-enyl) cyclohex-3-ene-1 -carbaldehyd (37677-14-8; Vertomugal); Hexanal; Heptanal; Octanal; 2-Nonen-1 -al; Nonanal; Decanal; Undecenal; 2-Methyldecanal; 10-Undecenal; Undecanal; Dodecanal; 2- Methylundecanal; Anisaldehyd; Benzaldehyd; Citral; Citronellal; Cinnamaldehyd; Cuminaldehyd; Cyclamenaldehyd; Dihydrocitronellal; trans-2-Dodecanal; Ethyl Vanillin; Geranial; Heliotropin / Piperonal; trans-2-Hexenal; alpha-Hexylzimtaldehyd; Hydratropaaldehyd; Hxdroxycitronellal; Isocyclocitral; Methoxycitronellal; Neral; Phenylacetaldehyd; Tangerinal; Vanillin;

[0027] Amine, Amide und Nitrile, wie beispielsweise 3,7-Dimethyloct-6-enenitril (51566-62-2; Argunitril); (E / Z)-3-Methyl-5-phenylpent-2-enenitril (53243-59-7; 53243-60-0; 93893-89-1; Citronitril); 3,7-Dimethylnona-2,6-dienenitril (61792-11 -8; Lemonil); 4-[(3£)-4,8-Dimethylnona-3,7-dienyl]pyridin (38462-23-6; Maritima); Tridec- 2-enenitril (22629-49-8; Ozonil); 2-Cyclohexylidene-2-phenylacetonitril (10461 -98-0; Peonile); Indol;

[0028] Ester, wie beispielsweise czs-2-tert-Butylcyclohexylacetat + (2-tert- Butylcyclohexyl)acetat (20298-69-5; 88-41 -5; Argumex HC / LC); Ethyl-3-methyl-3- phenyloxirane-2-carboxylat (77-83-8; Aldehyd C16 sogenannt); Prop-2-enyl-2- cyclohexyloxyacetat (68901 -15-5; Cyclogalbanat); Methyl-2,4-dihydroxy-3,6- dimethylbenzoat (4707-47-5; Evernyl); 4-Methylpentan-2-yl-(E)-but-2-enoat (35206- 51 -0; Frutinat); Ethyl-2-ethyl-6,6-dimethylcyclohex-2-ene-1 -carboxylat (57934-97-1; 77851 -07-1; Givescon); Methyl-3-oxo-2-pentylcyclopentaneacetat (24851 -98-7; Hedion); 2-(1 -(3',3'-Dimethyl-1 '-cyclohexyl)ethoxy)-2-methyl propyl propanoat (141773-73-1; Helvetolid); 3a,4,5,6,7,7a-Hexahydro-4,7-methanoinden-6-ylacetat (5413-60-5; Herbaflorat); 3a,4,5,6,7,7a-Hexahydro-4,7-methanoinden-6-ylacetat (5413-60-5; Herbaflorat); [(Z)-Hex-3-enyl]-methylcarbonate (67633-96-9; Leafovert); Ethyl-2-methylpentanoate (39255-32-8; Manzanat); 2-[1 -(3,3- Dimethylcyclohexyl)ethoxy]-2-oxoethylpropionat (236391 -76-7;Romandolid); Ethyl- 2-cyclopent-2-en-1 -ylacetat (15848-49-4; Sultanen); (1S,2 / ?,5S)-5-Methyl-2-(1 -; methylethyl)-cyclohexanolacetat + [(1 / ?,2S,5 / ?)-5-methyl-2-propan-2-ylcyclohexyl]- acetat (29066-34-0; 89-48-5; Symfresh RF I Menthylacetat); 3 -Hydroxy-2, 2, 4- trimethylpentyl 2-methylpropanoat (25265-77-4; Symfresh NX); (4-Methyl-4- phenylpentan-2-yl)-acetat (68083-58-9; Vetikolacetat); Allylamylglycolat; Allylcaproat; Allylcyclohexylpropionat; Allylheptoat; Benzylacetat; Benzylsalicylat; Citronellylacetat; Dimethylbenzylcarbinylacetat; Dimethylbenzylcarbinylbutyrat; Ethylbutyrat; Ethylcaproat; 2,4-Ethyldecadienoat; Ethyl-2-methylbutyrat; Ethylenbrassylat; Geranylacetat; Herbylpropionat; 3-Hexenylacetat; cis-3 Hexenylacetat; cis-3 Hexenylbutyrat; czs-3-Hexenylisobutyrat; czs-3-Hexenylsalicylat; Hexylacetat; Hexylbutyrat; Hexylisobutyrat; Hexylsalicylat; Isoamylacetat; Isobornylacetat; Isobutylacetat; Isoeugenolacetat; Linalylacetat; Methyloctincarbonat; Nerylacetat; Phenylethylbutyrat; Phenylethylcinnamat; Prenylacetat; Styralylacetat; Methylanthranilat;

[0029] Ether, wie beispielsweise Rosenoxid, (3a / ?,5aS,9aS,9b / ?)-3a,6,6,9a-Tetramethyl- 2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran (6790-58-5; Ambroxid); 5- Hexyl-4-methyloxolan-2-on (67663-01 -8; Aprifloren); Cyclohexadec-2-en-1 -on (2550- 59-6; 3100-36-5; 88642-03-9; Aurelion); 3,4-Diethyl-2,5-dimethylcyclohex-2-en-1 -on (68845-36-3; Azarbre); 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2- benzopyran (1222-05-5; Galaxolid); (2 / ?,4S)-2-Methyl-4-propyl-1,3-oxathian + 2- Methyl-4-propyl-1,3-oxathian (59323-76-1, 261 -699-8; Oxane / Oxanthia; 3,7'- Dimethyl-3,4,4a,5,8,8a-hexahydrospiro-(1,4-methanonaphthalen- 2[1 H],2'-oxirane) (41816-03-9; Rhubofix); Anethol; Limeoxid; Nerolin Yara Yara; Orange Flower Ether;

[0030] Ketone, wie beispielsweise 7-Methyl-3,4-dihydro-2H-[1,5]-benzodioxepin-3- on (249-320-4; Calone); 1,2,3,5,6,7-Hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-on (251 -649-3; Cashmeran); [3 / ?-(3a, 3a , 6a, 7p,8aa)]-Octahydro-6-methoxy-3, 6,8,8- tetramethyl-1H-3a,7-methanoazulen + (3 / ?,3aS,6 / ?,7 / ?,8aS)-octahydro-6-methoxy- 3,6,8,8-tetramethyl-1H-3a,7-methanoazulen (19870-74-7; 67874-81 -1; Cedramber); 3a,6,6,9a-Tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran (3738- 00-9; Cetalox); 1 -(5,5-Dimethyl-1 -cyclohexenyl)pent-4-en-1 -on (56973-85-4; Dynascon, Galbascon); 1 -[Bis(2-hydroxypropyl)amino]propan-2-ol; 5-Methylhept-2- en-4-on (102322-83-8; 81925-81 -7; Filberton); 4-(4-Hydroxyphenyl)butan-2-one (5471 -51 -2; frambinone); (8£)-Cyclohexadec-8-en-1 -one (3100-36-5; Globanone); 4-(2,5,6,6-Tetramethylcyclohex-2-enyl)but-3-en-2-one (201 -219-6; alpha-iron); 1 - (2,3,8,8-Tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone reaction mixture (54464-57-2; Iso E Super); Cyclohexadecanone (2550-52-9; Isomuscone), Iso E Super (reaction mixture from the acidic cyclization of 1-(1',6'-dimethyl-4'-(4"-methylpent-3"-en-1"-yl)cyclohex-3'-en-1'-yl)ethan-1-one), 5,5,9,13-Tetramethyl-14,16-dioxatetracyclo[11.2.1.0 1 / lo .O 4 ' 9]hexadecan (57345-19-4; Ketamber); 5-Hexyl-5- methyloxolan-2-on (7011 -83-8; Lactojasmon); (£)-3-Methyl-4-(2,6,6-trimethyl-1 - cyclohex-2-enyl)but-3-en-2-on (127-51 -5; Methyl Ionone Gamma Coeur); N-1 -(2,6,6- Trimethyl-1 -cyclohex-2-enyl)pent-1 -en-3-on (1335-46-2; Methyl Ionone Gamma Pure); (5£)-3-methylcyclopentadec-5-en-1 -on; (5£)-3-methylcyclopentadec-5-en-1 -on (63314-79-4; 82356-51 -2; Muscenon); 3-Methylcyclopentadecan-1 -on (541 -91 -3; Muscon); 2-[2-(4-Methyl-1 -cyclohex-3-enyl)propyl]cyclopentan-1 -on (95962-14-4; Nectaryl); 1 -(3-Methyl-1 -benzofuran-2-yl)ethan-1 -on (23911 -56-0; Nerolion); Octahydro-7-methyl-1,4-methanonaphthalen-6(2H)-on (41724-19-0; Plicaton); 1 - (3,5,5,6,8,8-Hexamethyl-6,7-dihydronaphthalen-2-yl)ethanon + 1 -(3, 5, 5, 6,8,8- Hexamethyl-6,7-dihydronaphthalen-2-yl)ethanone (1506-02-1; 21145-77-7; Tonalid); 2,2,5-Trimethyl-5-pentylcyclopentan-1 -one (65443-14-3; Velouton); damascene; a / p / ?a-Damascon; beta damascone; delta -Damascone; beta-dihydroionone; dihydrojasmone; ethyl maltol; a / p / ?a-lonone; beta-lonone; jasmine lactone; Jasmolactone CNC; czs-Jasmon; maltol; methyl ionone;

[0031] Lactones, such as 5-heptyloxolan-2-one (104-67-6; aldehyde C14 so-called); gamma-hexalactone; 5-Pentyloxolan-2-one (203-219-1; aldehyde C18 so-called); (9Z)-17-Oxacycloheptadec-9-en-1 -one (28645-51 -4; ambrettolide); (£12)- 1 -oxacyclohexadec-12-en-2-one + (£3)-oxacyclohexadec-3-en-2-one (111879-80-2; 34902-57-3; Globalid); 16-Oxacyclohexadecan-1 -one (106-02-5; Supra Macrolide); c / e / ta-decalactone; gamma-decalactone; gamma-octalactone.

[0032] Preferably, the compounds of formula (I) are combined with one or more, particularly preferably with two, three, four, five or more further The present invention relates to a mixture of odorants that do not conform to formula (I). In a preferred embodiment, these additional odorants have a fruity, floral-green, floral-rosy, floral-white, musky, or woody odor note. Accordingly, the present invention also relates to a mixture of odorants comprising one, two, three, four, five, or more additional odorants that do not conform to formula (I) and that impart a fruity, floral-green, floral-rosy, floral-white, musky, or woody odor note. Due to their green-balsamic fragrance, the use of the compounds of formula (I) according to the invention preferably results (at least partially) in an intensification or unexpected alteration of the fruity, floral-green, floral-rosy, floral-white, musky, or woody odor notes and / or odor effects.

[0033] In a preferred embodiment of the invention, at least one further fragrance ingredient, which does not correspond to formula (I), is selected from the group consisting of Agrumex LC (2-tert-butylcyclohexyl acetate), Ethylmethylbutyrate-2 (Ethyl-2-methylbutanoate), Isoamyl acetate (3-methylbutan-1-ol), Dimethylbenzylcarbinylbutyrat (1,1 -Dimethyl-2-Phenylethylbutyrat), Hexylacetat (Hexylacetat), Allylcyclohexylpropionat (Prop-2-en-1 -yl-3-cyclohexylpropionat), Dihydromyrcenol (2,6-Dimethyloct-7-en-2-ol), Ethyllinalool (3,7-Dimethylnona-1,6- dien-3-ol), Helional (3-(1,3-Benzodioxol-5-yl)-2-Methylpropanal), Cyclamenaldehyd (2-Methyl-3-[4-(propan-2-yl)phenyl]propanal), czs-Jasmon (czs-3-Methyl-2-pent-2- enylcyclopent-2-enon), Benzylacetat , Methyldihydrojasmonat (Methyl-3-oxo-2- Pentylcyclopentaneacetat), Methylanthranilat (Methyl -2-aminobenzoat), Methylionone 70 ((1 E)-1 -(2,6,6-Trimethylcyclohex-2-en-1 -yl)pent-1 -en-3-on;(3E)-3- Methyl-4-(2,6,6-Trimethylcyclohex-2-en-1 -yl)but-3-en-2-on), beta-lonon (4-(2,6,6- Trimethylcyclohex-1 -en-1 -yl)but-3-en-2-on), Geraniol (3,7-Dimethylocta-2,6-dien-1 - ol, Damascenon (1 -(2,6,6-Trimethylcyclohexa-1,3-dien-1 -yl)but-2-en-1 -on)), Phenylethylalkohol (2-Phenylethanol), Benzylsalicylat , Hexylsalicylat , Ambroxid ((3a / ?,5aS,9aS,9b / ?)-3a,6,6,9a-Tetramethyl-Dodecahydronaphtho[2,1 -b]furan), Iso E Super (Reaktionsmasse aus 1 -(1,2,3,4,5,6,7,8-Octahydro-2,3,8,8-Tetramethyl-2- Naphthyl)ethan-1 -on und 1 -(1,2,3,4,6,7,8,8a-Octahydro-2,3,8,8-Tetramethyl-2-; Naphthyl)ethan-1 -on und 1 -(1,2,3,5,6,7,8,8a-Octahydro-2,3,8,8-Tetramethyl-2- Naphthyl)ethan-1 -on), Cedrylacetat ([3 / ?-(3a, 3a , 6a, 7p,8aa)]-Octahydro-3, 6,8,8- tetramethyl-1H-3a,7-methanoazulen-5-yl-acetat), Sandranol (2-Ethyl-4-(2,2,3- Trimethylcyclopent-3-en-1 -yl)but-2-en-1 -ol), Polysantol ((4E)-3,3-Dimethyl-5-(2,2,3- Trimethylcyclopent-3-en-1 -yl)pent-4-en-2-ol), Vetiverylacetat (4,8-Dimethyl-2- (Propan-2-ylidene)-1,2,3,3a,4,5,6,8a-octahydroazulen-6-yl-acetat), Ambrettolid (Oxacycloheptadec- 10-en-2-on), Ethylenbrassylat (1,4-Dioxacycloheptadecan-5,17- dion), Globalid ((12£)-1 -Oxacyclohexadec-12-en-2-on; (12Z)-1 -Oxacyclohexadec-12- en-2-on; (13£)-1 -Oxacyclohexadec-13-en-2-on; (13Z)-1 -Oxacyclohexadec-13-en-2- on)), und Muscenon (3-Methyl-5-cyclopentadecen-1 -on) usw.

[0034] Preferably, at least one of the compounds of formula (I) is combined with one or more, particularly preferably with two, three, four, five or more of these preferred further fragrance substances.

[0035] Fragrance mixtures containing at least one of the compounds of formula (I) are advantageously used for perfumery in liquid form, undiluted or diluted with a solvent. Suitable solvents for this purpose are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, and isopropyl myristate.

[0036] Furthermore, fragrance mixtures according to the invention can be adsorbed onto a carrier, which ensures both a fine distribution of the fragrances in the product and a controlled release during application. Such carriers can be inorganic materials such as sulfate, silica gels, zeolites, plasters, clays, clay granules, aerated concrete, etc., or organic materials such as wood, cellulose-based materials, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates, or polyurethanes. The resulting combination of compositions according to the invention and the carrier material is also to be understood as a fragrance mixture according to the invention.

[0037] According to the invention, fragrance mixtures can also be microencapsulated, spray-dried or extruded and in this form added, for example, to a product to be perfumed.

[0038] If required, the properties of the modified compositions can be further optimized by so-called "coating" with suitable materials with regard to a more targeted release of fragrances, for which waxy plastics such as polyvinyl alcohol are suitable and preferred. The resulting products again constitute articles according to the invention.

[0039] Fragrance mixtures according to the invention can advantageously be used in concentrated form, in solutions or in the modified form described above for the production of perfumed articles according to the invention, such as... B. Perfume extracts, eau de parfums, eau de toilettes, aftershave, eau de cologne, pre-shave products, perfumed refreshing wipes and for the scenting of acidic, alkaline and neutral cleaning agents such as floor cleaners, window glass cleaners, dishwashing liquids, bathroom and sanitary cleaners, scouring creams, solid and liquid toilet cleaners, powder and foam carpet cleaners, fabric refreshers, ironing aids, liquid detergents, powder detergents, laundry pretreatment products such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets and disinfectants, air fresheners in liquid, gel or applied form on a solid carrier, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes,Shoe polishes and body care products in solid and liquid form; soaps, shower gels, shampoos, shaving soaps, shaving foams, bath products, cosmetic emulsions of the ol-in-water, water-in-oil and water-in-oil-in-water type, such as skin creams and lotions, face creams and lotions, sunscreens 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, hair care products such as hairsprays, hair gels, firming hair lotions, hair rinses, permanent and semi-permanent hair colorants, hair styling products such as cold waves and hair straighteners, hair lotions, hair creams and lotions, deodorants and, Antiperspirants such as underarm sprays, roll-ons, deodorant sticks, and deodorant creams; decorative cosmetics such as eyeshadow, nail polish, lipsticks, mascara, and candles; lamp shades; smoking sticks; insecticides; repellents; and propellants. The above list is only exemplary and not exhaustive; of course, other applications are also possible.

[0040] Fragrance mixtures according to the invention can also be included in cosmetic compositions or household compositions.

[0041] Another aspect of the invention is a perfumed article comprising or consisting of (i) a fragrance mixture as described above; as well as (ii) one or more further ingredients, preferably one or more excipients and / or active ingredients.

[0042] In a preferred embodiment, the perfumed article is selected from cosmetic, hygiene, and / or household articles. Other preferred embodiments listed above also apply to the perfumed article of the present invention.

[0043] Preferably, the perfumed article is selected from the group consisting of washing and cleaning agents, hygiene or care products, preferably from the area of ​​body and hair care, cosmetics and household products, preferably from the group consisting of perfume extracts, eau de parfum, eau de toilette, aftershave lotions, eau de cologne, pre-shave products, splash cologne, perfumed refreshing wipes, acidic, alkaline or neutral cleaning agents, fabric refreshers, ironing aids, liquid detergents, powder detergents, pre-wash products, fabric softeners, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body 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, decorative cosmetic products Cosmetics, candles, lamps, incense sticks, insecticides, repellents, and fuels. Perfumed items, especially those containing alcoholic perfume, personal care products, or cleaning and care products for household use, are particularly popular.

[0044] In a preferred embodiment of the invention, the perfumed article is selected from cosmetic, hygiene and / or household articles.

[0045] Furthermore, for the perfumed article according to the invention, it is preferred that at least one of the compounds of formula (I) is present in a sensorially effective amount sufficient for a consumer to perceive one or more olfactory properties selected from the group consisting of solar, floral (lily of the valley, ylang-ylang, orchid, hyacinth, mignonette, rose, orange blossom, jasmine, tuberose, mimosa), powdery, transparent, fruity, green, balsamic, and / or narcotic. It is also preferred that the total amount of compounds of formula (I), based on the total weight of the perfumed article, is in the range of 0.00001 to 10 wt.%, preferably 0.0001 to 5 wt.%, particularly preferably 0.001 to 2 wt.%, and particularly preferably 0.005 to 1 wt.%.

[0046] The additives, excipients, and / or active ingredients described above are preferably not fragrances. These may include, for example, preservatives, antibacterial agents, chelating agents, cleaning agents, emulsifiers, fats, etc., and basically any substances used as additives, excipients, and / or active ingredients in cosmetics, particularly in fragrance mixtures, as well as in household products.

[0047] In a preferred embodiment of the invention, at least one compound of formula (I) is used in fragrance compositions to achieve at least one of the following odor notes and / or odor effects: solar, floral (lily of the valley, ylang-ylang, orchid, hyacinth, mignonette, rose, orange blossom, jasmine, tuberose, mimosa), powdery, transparent, fruity, green, balsamic and / or narcotic.

[0048] Furthermore, the use of the compounds of formula (I), either a compound of formula (I) or a mixture of several compounds of formula (I), is preferred for mediating, modifying and / or enhancing one or more odor notes and / or odor effects of odorants that do not correspond to formula (I), wherein the one or more odor notes and / or odor effects are selected from the group consisting of fruity, floral-green, floral-rosy, floral-white, musky or woody odorants.

[0049] Consequently, the inventors made the surprising discovery that the compounds of formula (I) are suitable as fragrances and, in low doses, in combination with other fragrances, especially those with fruity, floral-green, floral-rosy, floral-white, musky, or woody notes, produce special effects. These effects are significantly better than those of the prior art methyl benzoates, which was not anticipated.

[0050] Furthermore, the compounds of formula (I) to be used according to the invention can enhance the intensity of an odorant mixture (fragrance composition or scent composition) and round off the overall odor of the mixture. The compounds described herein can therefore be used to give an odorant mixture more strength, purity, florality, naturalness, volume, fruitiness, freshness, spice, warmth, longevity, complexity, fineness, greenness, less perspiration odor, less animal odor, less mushroom odor and / or less terpene odor; in particular, the compounds according to the invention can be used to give an odorant mixture more transparency.

[0051] Furthermore, the compounds of formula (I) are suitable as means for increasing the substance vitality and / or retention of a fragrance mixture.

[0052] In a preferred embodiment of the invention, an inventive odorant mixture is used to convey, modify and / or enhance one or more odor notes and / or odor effects. The inventive odorant mixture comprises, as already described above, at least one compound of formula (I) and at least one odorant that does not conform to formula (I).

[0053] It goes without saying that all the above-mentioned preferred embodiments also apply to the use of the compound(s) of formula (I).

[0054] E. A further aspect of the invention relates to a method for imparting an odor note and / or modifying and / or intensifying an existing odor note, comprising or consisting of the following steps: a) providing at least one compound of formula (I); b) providing at least one odorant that does not correspond to formula (I); c) adding the at least one compound of formula (I) to the at least one odorant that does not correspond to formula (I) in a sensorially effective amount sufficient to impart an odor note and / or to modify and / or intensify an existing odor note.

[0055] In a preferred embodiment of the invention, the odor note is selected from the group consisting of: solar, floral (ylang-ylang, orchid, hyacinth, mignonette, rose, orange blossom, jasmine, tuberose, mimosa, lily of the valley), powdery, transparent, fruity, green, and / or narcotic. It is understood that all of the above-mentioned preferred embodiments also apply to the method according to the invention.

[0056] The invention will be further characterized based on the examples provided. Unless otherwise stated, all concentration values ​​are given in percent by weight. EXAMPLES Example 1 Production and odor properties of cyclopentyl-2-methylbenzoate (CPMB) by transesterification

[0057] In a 1000 ml three-necked flask stirred flask apparatus with a magnetic stirrer, contact thermometer, and a 30 cm column (Wilson coils) with a column head, 300 g (2.00 mol) of methyl 2-methylbenzoate, 172 g (2.00 mol) of cyclopentanol, and 28.0 g (203 mmol) of potassium carbonate were heated in reflux. The resulting methanol was distilled off (bottom temp.: 135–160 °C, top temp.: 65 °C, reflux ratio 25:1, reaction time: 70 h. During this time, the vacuum was steadily reduced to 100 mbar). After fractional destination, 306 g (75%) of the title compound cyclopenty-2-methylbenzoate were obtained (boiling point: 110-111 °C, 2-3 mbar, GC purity: 99.6%).

[0058] Scent: intense, floral, salicylate-like and solar.

[0059] DC: R f = 0.33 (SiO260, hexane / ethyl acetate = 20:1)

[0060] GC / MS: m / z (%): 41 (11), 51 (1), 65 (15), 77 (2), 85 (1), 91 (44), 119 (100), 136 (63), 186 (1), 204 (5).

[0061] GC-IR (Thermo Nicolet 6700): h = 3073 (w) / 3033 (w) / 2970 (w) / 2886 (w), 1737 (m), 1603 (w), 1462 (w), 1388 (w), 1290 (m) / 1254 (s), 1138 (w) / 1084 (m), 736 (f).

[0062] 1 H NMR (400 MHz, CDCI3): 8 = 7.86 (dd, J = 8.1, 1.5 Hz, 1 H), 7.38 (td, J = 7.5, 1.5 Hz, 1 H), 7.25 - 7.21 (m, 2H), 5.44 - 5.36 (m, 1 H), 2.59 (s, 3H), 2.02 - 1.89 (m, 2H), 1.89 - 1.82 (m, 2H), 1.84 - 1.76 (m, 2H), 1.72 - 1.60 (m, 2H).

[0063] 13 C NMR (101 MHz, CDCI3): S = 167.6, 139.7, 131.7, 131.6, 130.5, 130.4, 125.6, 77.5, 32.8, 23.8, 21.7. Example 2 Production and odor properties of hexyl-2-methylbenzoate (HMB) by Steglich esterification

[0064] In a 500 mL three-necked flask stirring apparatus equipped with a magnetic stirrer, internal thermometer, and reflux condenser, 10.0 g (73.4 mmol) of 2-methylbenzoic acid, 150 mL of dichloromethane, 1.80 g (14.7 mmol) of 4-dimethylaminopyridine, and nine times that amount (73.4 mmol) of hexan-1-ol were placed under a nitrogen atmosphere at room temperature. Subsequently, 13.8 g (58.8 mmol) of dicyclohexylcarbodiimide were added in four approximately equal portions, and the mixture was stirred for 24 h at room temperature. The precipitated solid was filtered off, and the resulting mother liquor was concentrated at 50 °C and 850 to 20 mbar using a rotary evaporator. The material thus obtained was dissolved in 150 ml of hexane at a warm temperature and then allowed to crystallize for 2 h at 5 °C. This residue was filtered off, and the mother liquor was concentrated at 60 °C and 400 to 20 mbar using a rotary evaporator, yielding 13.0 g of crude product (GC purity: 89.6%). After column chromatography of the second...From 00 g of crude product (Biichi PrepChrom C-700, 80 g silica gel 60, eluent: mobile phase hexane / acetic ester = 99:1, 20 ml / min at 20 ml per fraction) and subsequent bulb tube distillation (Biichi B-585) 1.40 g of the title compound were obtained (GC purity: 99%).

[0065] Scent: intense, floral, salicylate-like, creamy-white floral reminiscent of lily of the valley with hints of Florosa (Tetrahydro-2-isobutyl-4-methylpyran-4-ol).

[0066] DC: / ?f = 0.55 (Silica gel 60, Hexane / Acetic ester = 2:1)

[0067] GC / MS: m / z (%): 43 (32), 56 (8), 65 (18), 69 (5), 77 (3), 84 (5), 91 (50), 105 (1), 118 (100), 136 (86), 149 (1), 220 (18).

[0068] GC-IR (Thermo Nicolet 6700): h = 3073 (w), 3033.3 (w), 2966.9 (m), 2939.5 (m), 2871.2 (w) / 1736.2 (m) / 1603.3 (w), 1462.3 (w) / 1386.3 (w) / 1289.7 (m). 1253.6 (s) / 1138.9 (w), 1083.8 (m) / 735.8 (w).

[0069] 1H NMR (400 MHz, CDCI3): 8 = 7.90 (dd, J = 8.0, 1.5 Hz, 1 H), 7.39 (td, J = 7.5, 1.5 Hz, 1 H), 7.27 - 7.21 (m, 2H), 4.29 (t, J = 6.7 Hz, 2H), 2.60 (s, 3H), 1.83 - 1.68 (m, 2H), 1.52 - 1.40 (m, 2H), 1.40 - 1.28 (m, 4H), 0.94 - 0.87 (m, 3H).

[0070] 13 C NMR (101 MHz, CDCI3): 8 = 167.82, 140.00, 131.80, 131.65, 130.51, 130.03, 125.67, 64.94, 31.48, 28.71, 25.80, 22.57, 21.75, 14.02. Example 3 Production and odor properties of cyclohexyl-2-methylbenzoate (CHMB)

[0071] In a 500 mL three-necked flask stirring apparatus equipped with a magnetic stirrer, contact thermometer, and column head, 55.0 g (404 mmol) of 2-methylbenzoic acid, 1.56 g (8.08 mmol) of para-toluenesulfonic acid, 40.5 g (0.404 mol) of cyclohexanol, and 150 mL of cyclohexane were placed and stirred under reflux for 13 h. Once no further water had separated, the cyclohexane was distilled off, and the reaction mixture was stirred for a further 6 h at 100°C. It was cooled to room temperature and washed once with saturated sodium bicarbonate solution and twice with saturated sodium chloride solution, dried over sodium sulfate, and the remaining solvent was removed under vacuum. 63.3 g (64% yield) were obtained. Of the obtained quantity, 3 g were purified by columnar chromatography (silica gel, Cyclohexane / ethyl acetate 97:3), yielding 2.3 g (purity 99.7%) of cyclohexyl-2-methylbenzoate.

[0072] Scent: intense, floral, salicylate-like, creamy-white floral in the direction of lily of the valley with distinct hints of bourgeois, cyclamenaldehyde and green, ozone-like nuances.

[0073] 1 H NMR (600 MHz, CDCI3): 8 7.90 (dd, J = 7.6, 1.6 Hz, 1 H), 7.38 (td, J = 7.5, 1.5 Hz, 1 H), 7.26 - 7.21 (m, 2H), 5.02 (tt, J = 8.9, 3.9 Hz, 1 H), 2.60 (s, 3H), 2.00 - 1.92 (m, 2H), 1.83 - 1.74 (m, 2H), 1.62 - 1.54 (m, 3H), 1.45 (dtt, J = 13.6, 10.2, 3.6 Hz, 2H), 1.34 (dtt, J = 13.7, 10.1, 3.6 Hz, 1 H).

[0074] 13 C NMR (151 MHz, CDCI3): 8 167.3, 139.8, 131.7, 131.6, 130.6, 130.5, 125.7, 73.0, 31.7, 25.5, 23.8, 21.8.

[0075] GC / MS: m / z (%): 39 (9), 41 (14), 54 (6), 55 (19), 65 (18), 67 (16), 82 (7), 83 (7), 89 (7), 90 (8), 91 (48), 92 (5), 93 (6), 118 (52), 1 19 (89), 120 (8), 136 (100), 137 (33), 218 (9). Example 4 Production and odor properties of pentyl-2-methyl benzoate (PMB)

[0076] In a 500 mL three-necked flask stirred with a magnetic stirrer, contact thermometer, and water separator, 60.0 g (441 mmol) of 2-methylbenzoic acid, 1.70 g (8.81 mmol) of para-toluenesulfonic acid, 38.9 g (441 mmol) of n-pentanol, and 250 mL of cyclohexane were placed and stirred refluxed for 18 h. After cooling to room temperature, the mixture was washed once with saturated sodium bicarbonate solution and twice with saturated sodium chloride solution, dried over sodium sulfate, and the solvent was removed under vacuum. 76.4 g of a crude product were obtained, which was further purified by fractional destination (30 cm FKK, Raschigringe) yielding 59.3 g (65%, purity 99.9%) of pentyl-2-methylbenzoate.

[0077] Scent: subtly herbaceous, floral, salicylate-like in the direction of amyl salicylate with hints of clover and a distinct chocolate note as well as slightly metallic accents.

[0078] 1H NMR (400 MHz, CDCI3): 8 7.90 (dd, J = 8.1, 1.5 Hz, 1 H), 7.38 (td, J = 7.5, 1.5 Hz, 1 H), 7.25 - 7.21 (m, 2H), 4.29 (t, J = 6.7 Hz, 2H), 2.60 (s, 3H), 1.82 - 1.71 (m, 2H), 1.49 - 1.31 (m, 4H), 0.99 - 0.88 (m, 3H).

[0079] 13 C NMR (101 MHz, CDCI3): 8 167.8, 140.0, 131.8, 131.7, 130.5, 130.0, 125.7, 77.4, 77.0, 76.7, 64.9, 28.5, 28.3, 22.4, 21.8, 14.0.

[0080] GC / MS: m / z (%): 27 (5), 29 (8), 39 (8), 41 (11), 42 (5), 43 (25), 55 (7), 65 (23), 70 (6), 89 (7), 90 (13), 91 (58), 92 (6), 118 (100), 119 (72), 120 (6), 136 (66), 137 (26), 206 (14). Example 5: Combination experiments of pentyl-2-methylbenzoate (PMB) with fruity, floral-green, floral-rosy, floral-white, musky and woody fragrances Example 6 Combination experiments of cyclopentyl-2-methylbenzoate with fruity, floral-green, floral-rosy, floral-white, musky and woody fragrances Example 7 Demo Formula Cleanpow Hexyl-2-methyl benzoate (HMB) Evaluation with a 0.3% dosage in washing powder Evaluation results in pure washing powder

[0081] EMB: EMB greatly intensifies the technical-wintergrin and clean effect and is perceived as too strong.

[0082] PMB: PMB supports the floral ylang-ylang note, although rather weakly.

[0083] HMB: The floral body of the perfume oil is steered in a pleasant neroli direction by the HMB.

[0084] CPMB: The use of CPMB makes the floral effect more transparent and sensual.

[0085] CHMB: The floral character is enriched by the use of CHMB with a strong orchid facet, making it appear more present and voluminous. Evaluation results on wet wash

[0086] EMB: EMB provides a powdery, wintery green note that enhances the coconut top note.

[0087] PMB: The compound supports the white, transparent note and is perceived as pleasant, although not very strong.

[0088] HMB: The floral body of the parfum changes into a strong neroli-orange blossom note when HMB is used.

[0089] CPMB: The fragrance becomes greener and more metallic due to CPMB, and the compound gives the floral ylang-ylang note a rose oxide effect.

[0090] CHMB: The floral effect becomes more orchid-like and rosy through the use of the compound CHMB. Evaluation results on dry wash

[0091] EMB: EMB gives the perfume a strong white salicylate note and makes the fragrance appear more powdery.

[0092] PMB: The compound PMB gives the fruitiness of the perfume oil a long-lasting hold and substantivity.

[0093] HMB: Parfiimol appears greener and fresher on dry laundry due to the use of HMB.

[0094] CPMB: When using CPMB, a stronger floral and musky note may be perceived.

[0095] CHMB: The floral scent is perceived as more pronounced when applied to dry washes with CHMB. Example 8 Demo Formula Solarite Mystique Evaluation with a 10% dosage in Eau de Toilette MAJANTOL® ETHYLLINALOOL DIMETHYLBENZYLCARBINYL ACETATE PHENYLETHYLDIMETHYLCARBINOL TERPINEOL ALPHA ROSE OXIDE L 10% DPG PHENYLETHYL ALCOHOL ROSAPHEN ® BENZYL ACETATE HEDION ® JASMOLACTONE CNC JASMON CIS HEXYLSALICYLATE PHENYLETHYL SALICYLATE ISOEUGENOL ACETATE BELANIS® ANISALDEHYDE PURE HELIOTROPINE / PIPERONAL ETHYLVANILLIN 10% DPG CASS I AO EL 10% DPG BENZALDEHYDE DD 10% DPG CEDAR WOOD OIL VIRGINIA CASHMERAN CEDRAMBER ISO E SUPER JAVANOL AMBROXIDE AMBRETTOLIDE AURELIONE® GLOBALIDE ® INDOLE DIPROPYLENE GLYCOL EMB PMB Evaluation results

[0096] EMB: The EMB gives the fragrance an opulent tuberose character combined with a typical winter green note.

[0097] PMB: The solar, creamy and mineral character is enhanced by the PMB compound and reduces the greasy note of the fruity pineapple facet. Example 9 Demo formula Floral Yuzu Evaluation with a 0.5% dosage in body lotion Evaluation results

[0098] EMB: The floral-technical, winter-green note of EMB completely covers the transparent lily of the valley effect and the rosy note, and reinforces the woody-ambery character.

[0099] HMB: The HMB compound supports the transparent floral Notes, provides a stronger feminine character and emphasizes the green top note of the fragrance. Example 10 Demo Formula Lily Wash Evaluation with a 0.5% dosage in liquid detergent Evaluation results

[0100] EMB: The floral body transforms into a more opulent, white-flowered ylang-ylang and orange blossom direction. The fragrance ingredient EMB also intensifies the woody-ambery aspect of the fragrance.

[0101] CPMB: The floral lily of the valley character of the fragrance is supported and intensified by the CPMB blend, which also lends the perfume oil a more pronounced lily note. The fruitiness is also enhanced by CPMB. Example 11 Demo formula Easy Breezy with a 0.3% dosage in all-purpose cleaner, neutral Evaluation results

[0102] EMB: The fragrance EMB produces a strong, technical, winter green scent. An effect that masks the fruity apple part, but intensifies the aromatic apple character.

[0103] CHMB: The CHMB compound makes the fruity apple note appear more harmonious by enhancing the floral jasmine and rose body.

Claims

PATENT CLAIMS 1. Use of a compound of formula (I) as a fragrance. Single binding corresponds to 2. Use according to claim 1, wherein the compound corresponds to formula (I'). Formula (I') 3 Fragrance mixture comprising or consisting of at least one compound of formula (I) and / or formula (I') and at least one fragrance not conforming to formula (I) and / or formula (I').

4. Fragrance mixture according to claim 3, wherein the weight ratio of the at least one compound according to formula (I) and / or formula (I') to the total amount of the at least one fragrance not corresponding to formula (I) or (I') is in the range of 1:10 to 1:

100.

5. Fragrance mixture according to claim 3 and / or 4, wherein the amount of compounds of formula (I) is 0.01 to 50 wt.%, based on the total weight of the fragrance mixture.

6. Fragrance mixture according to at least one of requirements 3 to 5, wherein the amount of compounds of formula (I) is 0.01 to 1.5 wt.%, based on the total weight of the fragrance mixture.

7. Use according to claim 1 or 2 in fragrance compositions to achieve at least one of the following odor notes and / or odor effects: solar, floral (lily of the valley, ylang-ylang, orchid, hyacinth, mignonette, rose, orange blossom, jasmine, tuberose, mimosa), powdery, fruity, green, balsamic and / or narcotic.

8. Use according to claim 1 and / or 2 for conveying, modifying and / or enhancing one or more odor notes and / or odor effects selected from the group consisting of the notes fruity, floral-green, floral-rosy, floral-white, musky and woody.

9. Use of a fragrance mixture according to at least one of requirements 3 to 6 to convey, modify and / or enhance one or more odor notes and / or odor effects selected from the group consisting of the notes: fruity, floral-green, floral-rosy, floral-white-blossomed, musky and woody.

10. Method for imparting an odor note and / or modifying and / or enhancing an existing odor note, comprising or consisting of the following steps: a) providing at least one compound of formula (I) Single binding corresponds to Formula (I), and / or and preferably n = 1 Formula (I') b) Providing at least one odorant that does not conform to formula (I); c) Adding the at least one compound of formula (I) to the at least one odorant that does not conform to formula (I) in a sensorially effective quantity sufficient to impart an odor note and / or to modify and / or enhance an existing odor note.

11. The method according to claim 9, wherein the fragrance note is selected from the group consisting of: solar, floral (ylang-ylang, orchid, hyacinth, mignonette, Rose, orange blossom, jasmine, tuberose, mimosa, lily of the valley), powdery, fruity, green, and / or narcotic 12. Perfumed article, comprising or consisting of (i) a compound of formula (I) Single binding corresponds to sowie (ii) one or more further ingredients, preferably one or more excipients and / or active ingredients.

13. Perfumed article according to claim 12, comprising or consisting of (i) a compound of formula (I') and preferably n = 1 Formula (l'); as well as (ii) one or more further ingredients, preferably one or more excipients and / or active ingredients.

14. Perfumed article according to claim 12 or 13, wherein the article is selected from cosmetic, hygiene and / or household articles.

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