FRAGRANT MIXTURES CONTAINING ESTERS AND KETONES

Abstract

The invention relates to fragrant mixtures comprising at least one compound of general formula (I), a method for producing claimed fragrant mixtures, particularly perfume oils, perfumed products containing the claimed fragrant mixture, and the use of the compound of general formula (I) to strengthen the natural freshness and/or emanation and/or to mask or reduce greasy and/or metallic notes of one or more fragrant substances that differ from the compound of formula (B.

##STR00001##

Claims

1. An odorant mixture comprising at least one compound (a) of the general formula (I): ##STR00059## wherein, X is an oxygen atom or a methylene group, with the provisos that (i) none or one of the three wavy lines denotes a double bond and the other wavy lines each denote a single bond, and (ii) R is a linear or branched, cyclic, saturated or unsaturated hydrocarbyl radical having 1 to 5 carbon atoms.

2. The odorant mixture as claimed in claim 1, wherein the compound (a) of the general formula (I) is selected from the croup consisting of a compound of the following formula (Ia), a compound of the following formula (Ib) and mixtures thereof: ##STR00060##

3. The odorant mixture as claimed in claim 1 also comprising one or more further odorants (b), preferably with a green-herby and minty odor note, selected from the group consisting of ketones and nitriles having a molar mass of 120 g/mol to 210 g/mol, aldehydes and esters having a molar mass in the range from 110 g/mol to 250 g/mol and mixtures thereof.

4. The odorant mixture as claimed in claim 3, also comprising one or more further odorants (c) which function as a base note and selected from the group consisting of ketones and esters or lactones having a molar mass in the range from 220 g/mol to 320 g/mol and mixtures thereof.

5. The odorant mixture as claimed in claim 4, wherein the (i) mass ratio of the total amount of odorant (b) to the compound(s) (a) is not less than 99:1, and/or (ii) the mass ratio of the total amount of odorant (c) to the compound (a) is not less than 99:1, based in each case on the total amount of all odorants in the individual groups of compounds (a), (b) and (c), based on the overall odorant mixture.

6. The odorant mixture as claimed in claim 1, wherein the compound of the formula (I) selected from the group consisting of: methyl 2-cyclopent-2-en-1-ylacetate (compound II); ethyl 2-cyclopent-2-en-1-ylacetate (compound III); propyl 2-cyclopent-2-en-1-ylacetate (compound IV); isopropyl 2-cyclopent-2-en-1-ylacetate (compound V); allyl 2-cyclopent-2-en-1-ylacetate (compound VI); isopentyl 2-cyclopent-2-en-1-ylacetate (compound VII); cyclopentyl 2-cyclopent-2-en-1-ylacetate (compound VIII); [(E)-but-2-enyl] 2-cyclopent-2-en-1-ylacetate (compound IX); cyclopropylmethyl 2-cyclopent-2-en-1-ylacetate (compound X); 1,2-dimethylpropyl 2-cyclopent-2-en-1-ylacetate (compound XI); ethyl 2-(cyclopenten-1-yl) acetate (compound XII); methyl 2-cyclopentylideneacetate (compound XIII); methyl 2-cyclopentylacetate (compound XIV); propyl 2-cyclopentylacetate (compound XV); allyl 2-cyclopentylacetate (compound XVI); isopropyl 2-cyclopentylacetate (compound XVII); [(E)-but-2-enyl] 2-cyclopentylacetate (compound XVIII); 3-methylbut-2-enyl 2-cyclopent-2-en-1-ylacetate (compound XIX); ethyl 2-cyclopentylacetate (compound XX); 1-cyclopent-2-en-1-ylpropan-2-one (compound XXI); 1-cyclopent-2-en-1-ylhexan-2-one (compound XXII); 1-cyclopent-2-en-1-ylpent-4-en-2-one (compound XXIII); (E)-1-cyclopent-2-en-1-ylpent-3-en-2-one (compound XXIV); (Z)-1-cyclopent-2-en-1-ylpent-3-en-2-one (compound XXV) and mixtures thereof.

7. A perfume oil comprising the mixture as claimed in claim 1.

8. The odorant mixture as claimed in claim 1 in an amount effective for generation, imparting, modification or enhancement of a fruity odor in the apple, pear, pineapple, banana and strawberry direction.

9. A method of producing an odorant mixture as claimed claim 1, comprising the following steps: (a) providing a compound of the general formula (I), ##STR00061## (b) providing at least one further odorant, preferably having a green-herby and minty fragrance note and selected from the group consisting of ketones and nitriles having a molar mass of 120 g/mol to 210 g/mol, aldehydes and esters having a molar mass in the range from 110 g/mol to 250 g/mol and mixtures thereof, and/or (c) providing at least one or more further odorant selected from the group consisting of ketones and esters or lactones having a molar mass in the range from 220 g/mol to 320 g/mol and mixtures thereof, and (d) mixing the constituents (a), (b) and/or (c).

10. A method of enhancing the natural freshness and/or impression and/or for masking or reducing fatty and/or metallic notes of different odorants, comprising the following step: mixing the odorants with an amount of a compound of the formula (I) according to claim 1, sufficient to enhance the natural freshness and/or impression of the odorants, and/or mask or reduce fatty and/or metallic notes.

11. The method as claimed in claim 10, wherein the odorants other than the compound of the formula are selected from (b) at least one further odorant, preferably having a green-herby and minty fragrance note, and selected from the group consisting of ketones and nitriles having a molar mass of 120 g/mol to 210 g/mol, aldehydes and esters having a molar mass in the range from 110 g/mol to 250 g/mol and mixtures thereof, and/or (c) one or more further odorants selected from the group consisting of ketones and esters or lactones having a molar mass in the range from 220 g/mol to 320 g/mol and mixtures thereof.

12. The method as claimed in claim 10, wherein: the mass ratio of the total amount of odorants to the compound of the formula (I) is not less than 99:1.

13. A perfumed product comprising an odorant mixture, preferably a perfume oil, as claimed in claim 1, in a sensorily effective amount.

14. The perfumed product as claimed in claim 13, selected from: perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, acidic, alkaline and neutral cleaning products, textile fresheners, ironing aids, liquid laundry detergents, pulverulent laundry detergents, laundry pretreatment products, laundry softeners, laundry soaps, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, aftershave creams and lotions, tanning creams and lotions, haircare products, deodorants and antiperspirants, decorative cosmetics products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.

15. The perfumed product as claimed in claim 13, wherein the proportion of the odorant mixture in the perfumed product is 0.01% to 10% by weight, based on the total mass of the perfumed product.

16. The odorant mixture as claimed in claim 1, also comprising one or more further odorants (c) which function as a base note and selected from the group consisting of ketones and esters or lactones having a molar mass in the range from 220 g/mol to 320 g/mol and mixtures thereof.

Description

EXAMPLES

Example 1

General Preparation Method for a Compound of the Formula (I)

Preparation example: 1-cyclopent-2-en-1-ylpropan-2-one

[0323] ##STR00034##

[0324] A 100 ml three-neck flask with magnetic stirrer, contact thermometer, dropping funnel, 5 cm Vigreux column and distillation apparatus is initially charged with 69 mg (0.34 mmol) of aluminum triisopropoxide and 4.6 g (0.035 mol) of ethyl acetoacetate and heated up to 180 C. At this temperature, a solution of 12.6 g (0.15 mol) of 2-cyclopentanol and 21 g (0.16 mol) of ethyl acetoacetate is added dropwise within 2 h, with constant removal of distillate and evolution of carbon dioxide. The mixture is stirred at 180 C. for another 2 h. The residue (13 g) is distilled using a Kugelrohr (boiling range: 110 C./80-40 mbar). 8.1 g of distillate are obtained (GC: 84% product). 2.7 g of the distillate are subjected to preparative column treatment on 120 g of silica gel 60 with hexane/ethyl acetate (Bchi PrepChrom C-700, column: 120 g (SepaCore)). Yield: 1.5 g (GC: 99% product).

Example 2

[0325] List of Compounds of the General Formula (I) with Odor Descriptions and MS Data

Methyl 2-cyclopent-2-en-1-ylacelale (compound II)

[0326] ##STR00035##

[0327] GCMS: m/z (%)=140(11), 109(15), 108(20), 80(33), 79(31), 74(43), 67(100), 66(25), 43(16), 41(23), 39(20)

[0328] Odor profile: fruity in the strawberry direction

Ethyl 2-cyclopent-2-en-1-ylacetate (compound III)

[0329] ##STR00036##

[0330] GCMS: m/z (%)=154(31), 109(25), 108(27), 88(39), 83(36), 80(47), 79(64), 67(100), 66(28), 41(23)

[0331] Odor profile: sweet, fruity, green, in the direction of pear, pineapple, apricot and kiwi

Propyl 2-cyclopent-2-en-1-ylacetate (compound IV)

[0332] ##STR00037##

[0333] GCMS: m/z (%)=168(6), 109(30), 108(27), 107(20), 83(26), 80(32), 79(44), 67(100), 66(31), 61(22), 41(28)

[0334] Odor profile: sweet, fruity, green, fatty, in the pineapple direction

Isopropyl 2-cyclopent-2-en-1-yl acetate (compound V)

[0335] ##STR00038##

[0336] GCMS: m/z (%)=168(1), 126(16), 125(15), 109(21), 108(29), 80(15), 79(26), 67(100), 66(34), 43(17), 41(17)

[0337] Odor profile: sweet, fruity, bergamot and violet

Allyl 2-cyclopent-2-en-1-ylacetate (compound VI)

[0338] ##STR00039##

[0339] GCMS: m/z (%)=125(56), 107(42), 83(62), 80(18), 79(100), 77(12), 67(82), 66(14), 41(56), 39(29)

[0340] Odor: sweet, fruity, green, in the pineapple direction

Isopentyl 2-cyclopent-2-en-1-ylacetate (compound VII)

[0341] ##STR00040##

[0342] GCMS: m/z (%)=196(4), 80(23), 79(33), 71(51), 70(27), 67(81), 66(23), 43(100), 41(52), 39(25), 27(22)

[0343] Odor profile: sweet, fruity, green, in the apple and pear direction

Cyclopentyl 2-cyclopent-2-en-1-ylacetate (compound VIII)

[0344] ##STR00041##

[0345] GCMS: m/z (%)=126(18), 109(21), 108(37), 80(13), 79(13), 69(9), 68(9), 67(100), 66(25), 41(22)

[0346] Odor profile: sweet, fruity, in the pineapple direction

[(E)-But-2-enyl]2-cyclopent-2-en-1-ylacetate (compound IX)

[0347] ##STR00042##

[0348] GCMS: m/z (%)=125(65), 108(17), 107(41), 83(51), 79(76), 67(100), 66(26), 55(49), 41(22), 39(22)

[0349] Odor profile: sweet, mushroomy, fruity, in the pineapple direction

[0350] Cyclopropylmethyl 2-cyclopent-2-en-1-ylacetate (compound X)

##STR00043##

[0351] GCMS: m/z (%)=125(33), 107(38), 83(35), 80(19), 79(56), 67(80), 55(100), 41(17), 39(17), 29(21)

[0352] Odor profile: sweet, mushroomy, fruity, in the pineapple direction

[0353] 1,2-Dimethylpropyl 7-cyclopent-2-en-1-ylacetate (compound XI)

##STR00044##

[0354] GCMS: m/z (%)=126(14), 109(57), 108(25), 79(13), 71(43), 70(24), 67(100), 66(19), 43(42), 41(15)

[0355] Odor profile: sweet, green, fruity, in the pineapple direction

Ethyl 2-(cyclopenten-1-yl) acetate (compound XII)

[0356] ##STR00045##

[0357] GCMS: (%)=154(36), 125(6), 108(39), 88(9), 83(36), 81(100), 67(45), 53(21), 41(22)

[0358] Odor profile: sweet, fresh, fruity, in the apple direction

Methyl 2-cyclopentylideneacetate(compound XIII)

[0359] ##STR00046##

[0360] GCMS: m/z (%)=140(100), 125(7), 109(66), 81(42), 74(26), 67(31), 53(25), 41(28)

[0361] Odor profile: sweet, green, fruity, in the banana direction, floral like ylang and honey-like

Methyl 2-cyclopentylacetate (compound XIV)

[0362] ##STR00047##

[0363] GCMS: m/z (%)=142(1), 111(11), 99(10), 83(11), 75(28), 74(100), 67(11), 59(10), 55(22), 43(23), 41(20)

[0364] Odor profile: sweet, fruity, in the valerate direction

Propyl 2-cyclopentylacetate (compound XV)

[0365] ##STR00048##

[0366] GCMS: m/z (%)=129(43), 111(56), 102(17), 83(48), 67(21), 61(100), 60(48), 55(34), 43(24), 41(35)

[0367] Odor profile: sweet, fruity, in the banana direction

Allyl 2-cyclopentylacetate (compound XVI)

[0368] ##STR00049##

[0369] GCMS: m/z (%)=168(2), 111(50), 100(36), 83(100), 82(17), 67(45), 55(76), 54(19), 43(24), 41(87), 39(24)

[0370] Odnr arofile: sweet, green, fruity, in the pineapple direction

Isopropyl 2-cyclopentylacetate (compound XVII)

[0371] ##STR00050##

[0372] GCMS: m/z (%)=129(34), 111(63), 102(48), 83(67), 68(32), 61(62), 60(100), 55(43), 43(69), 41(48)

[0373] Odor: sweet, fruity, in the banana direction, floral, rosy

[(E)-But-2-enyl] 2-cyclopentylacetate (compound XVIII)

[0374] ##STR00051##

[0375] GCMS: m/z (%)=182(4), 111(50), 109(12), 83(77), 67(23), 55(100), 54(14), 41(19), 39(13), 29(16), 27(10)

[0376] Odor profile: sweet, fruity, in the pineapple direction, citrus-like

3-Methylbut-2-enyl 2-cyclopent-2-en-1-ylacetate (compound XIX)

[0377] ##STR00052##

[0378] GCMS: m/z (%)=126(23), 125(31), 108(29), 83(22), 79(32), 69(79), 68(39), 67(100), 66(22), 41(62)

[0379] Odor profile: sweet, fruity

Ethyl 2-cyclopentylacetate (compound XX)

[0380] ##STR00053##

[0381] GCMS: m/z (%)=156(1), 111(26), 89(23), 88(100), 83(30), 70(33), 61(27), 60(28), 55(29), 41(33), 29(22)

[0382] Odor profile: sweet, fruity, in the apple and strawberry direction

1-Cyclopent-2-en-1-ylpropan-2-one (compound XXII)

[0383] ##STR00054##

[0384] GCMS: m/z (%)=124(34), 109(27), 81(20), 79(21), 67(72), 66(100), 65(11), 43(68), 41(18), 39(18)

[0385] Odor profile: green, fruity, nutty

1-Cyclopent-2-en-1-ylhexan-2-one (compound XXII)

[0386] ##STR00055##

[0387] GCMS: m/z (%)=166(9), 109(100), 85(15), 81(17), 79(19), 67(93), 57(41), 41(53), 29(31), 27(20)

[0388] Odor profile: green, fruity

1-Cyclopent-2-en-1-ylpent-4-en-2-one (compound XXIII)

[0389] ##STR00056##

[0390] GCMS: m/z (%)=150(1), 109(42), 81(7), 79(8), 68(6), 67(100), 66(5), 65(6), 53(5), 41(19), 39(10)

[0391] Odor profile: green, fruity

(E)-1-Cyclopent-2-en-1-ylpent-3-en-2-one (compound XXIV)

[0392] ##STR00057##

[0393] GCMS: m/z (%)=150(5), 122(16), 107(16), 84(42), 80(26), 79(18), 69(100), 67(43), 66(16), 41(48), 39(22)

[0394] Odor profile: green, fruity, somewhat eugenol-like

(Z)-1-Cyclopent-2-en-1-ylpent-3-en-2-one (compound XXV)

[0395] ##STR00058##

[0396] GCMS: m/z (%)=150(5), 122(16), 107(16), 84(50), 80(27), 79(19), 69(100), 67(32), 66(15), 41(17), 39(23)

[0397] Odor profile: green, fruity, somewhat eugenol-like

Example 3

[0398] Odor Description of Preferred Odorants After Addition of Compounds of the Formula (I) or (Ia)

TABLE-US-00002 Mass ratio of the Compound odorant to the of the compound of the Odor description by formula (I) formula (I) or (Ia) comparison with the odor of Odorants Type or (Ia) (0.1% in DPG) the pure odorant Cantryl Nitrile VI 99:1.0 Softer, more natural, more (M = 149) lively, spicier in the direction of thyme Menthone Ketone XIX 99:1.0 The odorant loses its metallic (M = 154) note and seems more natural, sweeter with a sweet peppermint character Peonile Nitrile I 99:1.0 Less industrial, fresh, natural (M = 197) salicyl-like flower note Parmanyl Nitrile XIII 99:1.0 Less fatty, less metallic, more (M = 153) rounded, more natural, much more volume and impact Tolylacetalde- Aldehyde VI 100:1.0 Less metallic, fresher, more hyde natural, more rounded and (M = 134) sweeter in the almond direction Phenylacetalde- Aldehyde XIX 100:1.0 Less greasy, less metallic, more hyde rounded (M = 120) Cyclogalbanate Ester I 100:1.0 Less metallic, more rounded, (M = 198) more natural Frescomenthe Ketone XII 100:1.0 Less metallic, more rounded, (M = 154) more harmonic with natural effects Isooctanone Ketone XIV 100:1.0 Less metallic, more rounded, (M = 128) more harmonic, fresher with Cognac effect Ethyl cinnamate Ester XIV 100:1.0 Less metallic, more rounded, (M = 176) more harmonic, sweet, balsamic note

[0399] Conclusion: The compounds of the formula (I) or (Ia) promote the natural lively effect in herby, minty and green odorants.

Example 4

[0400] Perfume oils P1 P5

TABLE-US-00003 TABLE 1 Perfume oil P1 (amounts in g) Ingredient Formulation A Formulation B Aldehyde C11 MOA 4 4 Aldehyde C12 MNA 1 1 Limonenal 6 6 Magnolan 50 50 Mintonat 50 50 Dihydromyrcenol 50 50 Citral 95 5 5 Mandaril 1 1 Citronitrile 50 50 Agrunitrile 50 50 Citronella Oil 4 4 Citrylal 30 30 Orange Oil Terpenes 180 180 Oxanthia 50% 10% 6 6 Phellandrene alpha L Natural 140 140 Eucalyptol Nat. 17 17 Carvone L 17 17 Thymol Cryst. 4 4 Basil Oil GRD Vert Type Linalool 1 1 Borneol L 6 6 Ethyl butyrate 4 4 Passifloran 10% 1 1 Buccoxime 1 1 Geraniol super 40 40 Geranyl acetate 60 40 40 Hedione 90 90 Poivrol 25 25 Ambrocenide 10 1 1 Globalide 50 50 Triethyl citrate 25 20 Cantryl 51 51 Compounds of the formula (Ia) 5 or (Ib) 10% in TEC

[0401] Version B is much more lively in its freshness and finely rounds off the flowery note. The marked soapy note in version A is balanced out by the compounds of the formula (I) or (Ia). The effect is assessed as being particularly clear with compounds VII and XVI.

TABLE-US-00004 TABLE 2 Perfume oil P2 (amounts in g) Ingredient Formulation A Formulation B Farenal 1% 20 20 Mandarin Aldehyde 10% 5 5 Florazon 10 10 Leafovert 10% 20 20 Vertocitral 1 1 Bergamot Oil 100 100 Linalyl acetate 50 50 Dihydromyrcenol 60 60 Orange Oil 25 25 Lavandin Oil 20 20 Cassis Base 345BB 10 10 Calone 1951 10% 30 30 Majantol 45 45 Linalool 60 60 Terpineol pure 20 20 Damascone alpha 1% 20 20 Hexylcinnamicaldehyde alpha 100 100 Hedion HC/30 10 10 Hedione 200 200 Hexyl salicylate 20 20 Clove Bud Oil 5 5 Kephalis 5 5 Iso E Super 70 70 Terranol 30 30 Polysantol 5 5 Globalide 20 20 Ethylene brassylate 20 20 Farenal 1% 20 20 Mandarin Aldehyde 10% 5 5 Florazon 10 10 Leafovert 10% 20 20 Vertocitral 1 1 Bergamot Oil 100 100 Linalyl acetate 50 50 Dihydromyrcenol 60 60 Orange Oil 25 25 Triethyl citrate 9 8 Cyclogalbanate 10 10 Compounds of the formula (I) 1 or (Ia) 10% in TEC

[0402] Version B removes the aggressive green top note. The marine-like accord is integrated into the fragrance by addition of the compounds of the formula (I) or (Ia), giving rise to a gentle spruce effect. The effect is assessed as being particularly clear with the compounds II and XXII.

TABLE-US-00005 TABLE 3 Perfume oil P3 Ingredient Formulation A Formulation B Aldehyde C11 MOA 10% 20 20 Leafovert 10% 10 10 Cyclogalbanate 20 20 Styrallyl acetate 15 15 Floropal 10 10 Mintonat 40 40 Linalyl acetate 10 10 Dihydromyrcenol 340 340 Citral Melange 5 5 Geranylnitrile Replacement 5 5 Orange Oil 50 50 Mandarin Oil 10 10 Amarocite 10 10 Nerolione 10% DPG 15 15 Lavandin Oil 25 25 Eucalyptol Nat. 15 15 Menthol Laevo Dist. 100 100 Cyclamenaldeyhde 10 10 Linalool 65 65 Citronellol 950 20 20 Isodamascon 10% 10 10 Hedione 20 20 Isoraldeine 70 20 20 Anethol supra 10 10 Agrumex HC 5 5 Vertofix 10 10 Iso E Super 90 90 Sandranol 10 10 Aurelione 20 20 Triethyl citrate 9 8 Frescomenthe 10 10 Compounds of the formula 1 (Ia) or (Ib) 10% in DPG

[0403] The compounds of the formula (I) or (Ia) push the fresh and minty notes. A transparent, watery effect is the result and makes the composition seem cleaner. The effect is assessed as being particularly marked with the compounds XIV and XXIII.

TABLE-US-00006 TABLE 4 Perfume oil P4 Ingredient Formulation A Formulation B Octenol-1,3 5 5 Mintonat 195 195 Linalyl acetate 80 80 Dihydromyrcenol 35 35 Neononyl acetate 80 80 Terpinyl acetate 100 100 Eucalyptus Oil 80 80 Artemisia Oil 10% 10 10 Terpinenol-4 5 5 Thymol crist. 10% 10 10 Maceal 10% 10 10 Borneol crist. 60 60 Hexylacetate 5 5 Hexylbutyrate 5 5 Linalooloxide 5 5 Tetrahydrolinalool 90 90 Filbertone 10% 5 5 Linalool 80 80 Jessemal 20 20 Eugenol 10 10 Coumarone 20 20 Cyclabute 25 25 Vetival 10 10 Patchouly Oil 10 10 Evernyl 1 1 Isomuscone 10 10 Triethyl citrate 9 6.5 Isooctanone 25 25 Compounds of the formula 2.5 (I) or (Ia) 10% in DPG

[0404] Here, the compounds of the formula (I) or (Ia) turn the fragrance in a herby direction. A sweet impression is the result, the lavender/coumarin note of which seems much more marked. At the same time, the camphor-like note is covered a little. The effect is assessed as being particularly marked with the compounds XV and XXII.

TABLE-US-00007 TABLE 5 Perfume oil P5 Ingredient Formulation A Formulation B Citral 15 15 Pinen alpha laevo nat. 10 10 Linalool 100 100 Linalool oxide 3.5 3.5 Terpineol alpha 10 10 Geranium chin. 15 15 Rose oxide high cis 6.5 6.5 Citronellol 390 390 Geraniol 200 200 Citronellyl formate 80 80 Geranyl acetate 8.5 8.5 Geranyl butyrate 10 10 Geranyl formate 65 65 Geranyl isobutyrate 4.5 4.5 Geranyl propionate 20 20 Geranyl tiglinate 10 10 Caryophyllene nat. rect. 7 7 Triethyl citrate 10 6.5 Menthone 35 35 Compounds of the formula (I) 3.5 or (Ia) 10% in TEC

[0405] The compounds of the formula (I) or (Ia) push the freshness here too. The slightly metallic minty note is distinctly reduced and rounded off. The effect is assessed as being particularly clear with the compounds XX and XXI.

Example 5

[0406] Formulation Examples F1 to F11

[0407] Perfume oils P1, P2, P3, P4 and P5 made from the above perfume oil examples 1 to 5 were each incorporated separately into the formulations which follow. The odor effects described above for the respective perfume oil were each also observed in the formulations which follow.

TABLE-US-00008 TABLE 6 Washing powder (figures in % by weight) Material Chemical name Function A B Sodium Sodium metasilicate pentahydrate Ad 100 Ad 100 metasilicate pentahydrate Sodium hydrogen- Sodium hydrogen carbonate Alkali 15.0 15.0 carbonate Sodium Sodium carbonate peroxyhydrate Bleach 15.0 15.0 percarbonate Peractive AC Blue TAED/NaCarboxymethylcellulose Activator 5.00 5.00 Genapol OA-080 Oxo alcohol C14-15, 8EO Nonionic 3.00 3.00 surfactant Texapon K12 Sodium Lauryl Sulfate C12 Anionic 7.00 7.00 powder surfactant Tinopal CBS-X Brightener 0.50 0.50 Savinase 6.0 T, Type Protease Enzyme 0.40 0.40 W Termamyl 120 T Alpha-Amylase Enzyme 0.30 0.30 Sodium sulfate Sodium Sulfate Filler 5.50 5.50 Perfume oil P1, P2, Perfume 0.30 0.50 P3, P4 or P5 (fragrance)

TABLE-US-00009 TABLE 7 All-purpose cleaner (figures in % by weight) Material Chemical name Function A B Deionized water Water Solvent Ad 100 Ad 100 Mergal K9N 5-Chloro-2-methyl-3- Preservative 0.1 0.1 (2H)-isothiazolone and 2-methyl-3- (2H)-isothiazolone Trisodium citrate Tri Sodium Citrate Complexing 3.0 3.0 dihydrate Dihydrate agent Zetesol NL-2 Fatty alcohol C12- Anionic 30.0 30.0 14-sulfate, Sodium surfactant Imbentin Fatty alcohol C12- Nonionic 5.0 5.0 C/125/055 C15, 8EO surfactant Ethanol Ethanol Solvent 2.0 2.0 Perfume oil P1, Parfum 0.3 0.5 P2, P3, P4, or P5 (fragrance)

TABLE-US-00010 TABLE 7 Shampoo (figures in % by weight) Material INCI-Name A B Deionized water Water Ad 100 Ad 100 Plantacare PS 10 Sodium Laureth Sulfate, Lauryl Glucoside 20.0 20.0 Euperlan PK 771 Glycol Distearate, Sodium Lauryl Sulfate, Cocamide 6.0 6.0 MEA, Laureth-10 Dragocid Liquid Phenoxyethanol, Methylparaben, Ethylparaben, 0.5 0.5 Butylparaben, Propylparaben, Isobutylparaben Sodium chloride Sodium Chloride 1.4 1.4 Citric acid monohydrate Citric Acid 0.1 0.1 crystalline Perfume oil P1, P2, P3, Parfum (fragrance) 0.5 0.8 P4, or P5

TABLE-US-00011 TABLE 8 Shower gel (figures in % by weight) Material INCI-Name A B Deionized water Water Ad 100 Ad 100 Plantacare PS 10 Sodium Laureth Sulfate, Lauryl 20.0 20.0 Glucoside Dragocid Liquid Phenoxyethanol, Methyl- 0.5 0.5 paraben, Ethylparaben, Butylparaben, Propylparaben, Isobutylparaben Sodium chloride Sodium Chloride 1.4 1.4 Citric acid Citric Acid 1.3 1.3 monohydrate crystalline Perfume oil P1, Parfum (fragrance) 0.5 0.7 P2, P3, P4, or P5

TABLE-US-00012 TABLE 9 Fabric softener (figures in % by weight) Material Chemical name Function A B Deionized water Water Solvent Ad 100 Ad 100 Rewoquat WE 18 Dialkylesterammonium Cationic surfactant 16.6 16.6 ethosulfate Mergal K9N 5-Chloro-2-methyl-3-(2H)- isothiazolone and 2-methyl-3- Preservative 0.10 0.10 (2H)-isothiazolone Dow Corning Polydimethylsiloxane Defoamer 0.30 0.30 1520 antifoam Magnesium Magnesium Chloride solution Bodying agent 10.00 10.00 chloride 1% solution Perfume oil P1, Fragrance 0.55 0.75 P2, P3, P4, or P5

TABLE-US-00013 TABLE 10 Eau de Cologne/Eau de Toilette (figures in % by weight) Ingredients A B Perfume oil P1, P2, P3, P4, or P5 5 10 Ethanol Ad 100 Ad 100 Water 18 10

TABLE-US-00014 TABLE 11 Aerosol pump spray (figures in % by weight) Ingredients A B Perfume oil P1, P2, P3, P4, or P5 1.0 1.5 Ethanol Ad 100 Ad 100 Water 5.0 8.0 alpha-Tocopherol 0.20 0.20 Hydroxypropylcellulose 0.20 Rosemary extract, soluble in ethanol 0.22 Cetyl alcohol 1.00 0.50

TABLE-US-00015 TABLE 12 Shampoo (figures in % by weight) Ingredients A B C Sodium lauryl ether sulfate (e.g. Texapon NSO, from Cognis 12 12 12 Deutschland GmbH) Cocamidopropyl betaine (e.g. Dehyton K, from Cognis 2 2 2 Deutschland GmbH) Sodium chloride 1.4 1.4 1.4 Citric acid 1.3 1.3 1.3 Phenoxyethanol, methyl-, ethyl-, butyl- and propylparaben 0.5 0.5 0.5 Perfume oil P1, P2, P3, P4, or P5 0.3 0.5 0.7 Water Ad 100 Ad 100 Ad 100

TABLE-US-00016 TABLE 13 Washing powder (figures in % by weight) Ingredients A B C Linear Na alkylbenzenesulfonate 8.8 8.8 8.8 Ethoxylated fatty alcohol C12-18 (7 EO) 4.7 4.7 4.7 Na soap 3.2 3.2 3.2 DOW CORNING(R) 2-4248S 3.9 3.9 3.9 POWDERED ANTIFOAM, silicone oil on zeolite as carrier material Zeolite 4A Ad 100 Ad 100 Ad 100 Na carbonate 11.6 11.6 11.6 Na salt of a copolymer of acrylic acid 2.4 2.4 2.4 and maleic acid (Sokalan CP5) Na silicate 3.0 3.0 3.0 Carboxymethylcellulose 1.2 1.2 1.2 Dequest 2.8 2.8 2.8 2066([[(Phosphonomethyl)imino]bis [(ethylenenitrilo)bis(methylene)]] tetrakisphosphonic acid, sodium salt) Optical brightener 0.2 0.2 0.2 Na sulfate 6.5 6.5 6.5 Protease 0.4 0.4 0.4 Sodium perborate tetrahydrate 21.7 21.7 21.7 Perfume oil P1, P2, P3, P4, or P5 0.25 0.35 0.5 EDTA 1.0 1.0 1.0

TABLE-US-00017 TABLE 14 Liquid washing composition (figures in % by weight) Ingredients A Deionized water 39.9 Optical brightener 0.10 Coconut fatty acids (C12-C18) 7.5 Potassium hydroxide 50% solution 4.3 Propane-1,2-diol 5.00 Fatty alcohols C12-C15, 8 EO 12.0 Na salt of secondary alkylsulfonates (C13-C17) 17.0 Triethanolamine 2.0 Trisodium citrate dihydrate 5.0 Dequest 2066([[(Phosphonomethyl)imino]bis 3.0 [(ethylenenitrilo)bis(methylene)]]tetrakis- phosphonic acid, sodium salt) Ethanol 3.0 Enzymes 0.7 Perfume oil P1, P2, P3, P4, or P5 0.5

TABLE-US-00018 TABLE 15 Liquid washing composition concentrate (figures in % by weight) Ingredients A Deionized water 13.4 Coconut fatty acids (C12-C18) 10.0 Fatty alcohols C12-C15, 8 EO 26.0 Na salt of secondary alkylsulfonates (C13-C17) 26.5 Triethanolamine 8.5 Na salt of fatty alcohol sulfates C12-C14 3.0 Ethanol 5.5 Urea 4.5 Enzymes 0.9 Citric acid 1.0 Perfume oil P1, P2, P3, P4, or P5 0.7

Example 6

Stability Test

[0408] The fabric softener F5 and Eau de Cologne F6 from example 5 were stored in order to assess the stability of the formulation and the fragrance note after the storage time. The results are shown in table 16:

TABLE-US-00019 TABLE 16 Stabilities 4 weeks 8 weeks 23 C. 40 C. 23 C. 40 C. F5 without Formulation stable, Formulation stable, Formulation stable, Formulation stable, perfume Fragrance in a Fragrance in a Camphor-like note Camphor-like note oils of the herby direction herby direction becomes becomes invention prominent prominent F5 from Formulation stable, Formulation stable, Formulation stable, Formulation stable, example 5 Lavender/coumarin Lavender/coumarin Lavender/coumarin Lavender/coumarin note more marked, note marked, note present, note present, sweetish sweetish sweetish sweetish impression impression impression impression F6 without Formulation stable, Formulation stable, Formulation stable, Formulation stable, perfume Fresh, light- Fresh, metallic Fresh, light- light-colored, oils of the colored, slightly colnred, metallic metallic invention metallic F6 from Formulation stable, Formulation stable, Formulation stable, Formulation stable, example 5 Fresh, light- Fresh, light- Fresh, light- Fresh, light- colored, minty colored, minty note colored, minty note colored, minty note note, not metallic slightly reduced, slightly reduced, distinctly reduced, not metallic not metallic slightly metallic