BLENDS CONTAINING ENANTIOMERICALLY PURE AMBROCENIDE®

Abstract

The present invention relates in particular to a mixture comprising the compound of formula (Ia) as described herein, wherein the mixture is free or essentially free of the compound of formula (Ib) as described herein, preferably of the compounds of formulae (Ib) and furthermore (Ic) and/or (Id) as described herein. The invention further relates to a method for manufacturing said mixture, fragrance substance compositions containing or consisting of said mixture, perfumed products containing said mixtures or fragrance substance compositions, and various methods and uses for imparting, modifying and/or enhancing certain odour notes.

Claims

1. A mixture comprising: a compound of formula (Ia), ##STR00022## wherein the mixture is free of a compound of formula (Ib), ##STR00023##

2. The mixture according to claim 1, further comprising: one or more compound(s) of formula (II) ##STR00024## formula (III) ##STR00025## formula (IV) ##STR00026## formula (V) ##STR00027## and/or or formula (VI) ##STR00028##

3. A mixture according to claim 1, further comprising one or more compound(s) of formula (II), ##STR00029## wherein a weight ratio of a total amount of compound of formula (Ia) to a total amount of compound(s) of formula (II) is 500:1 to 3:1; one or several compound(s) of formula (III), ##STR00030## wherein a weight ratio of a total amount of compound of formula (Ia) to a total amount of compound(s) of formula (III) is at least 5:1; one or more compound(s) of formula (IV), ##STR00031## wherein a weight ratio of a total amount of compound of formula (Ia) to a total amount of compound(s) of formula (IV) is at least 40:1; one or more compound(s) of formula (V), ##STR00032## wherein a weight ratio of a total amount of compound of formula (Ia) to a total amount of compound(s) of formula (V) is at least 30:1; or and/or one or more compound(s) of formula (VI), ##STR00033## wherein a weight ratio of the total amount of compound of formula (Ia) to the total amount of compound(s) of formula (VI) is at least 4:1.

4. A method for manufacturing a mixture according to claim 1, comprising: a) providing a feed mixture comprising alpha,alpha-cedranediol of formula (IIIa), ##STR00034## wherein the feed mixture is free of beta,beta-cedranediol of formula (IIIb), ##STR00035## b) reacting the alpha,alpha-cedranediol of formula (IIIa) with dimethoxypropane.

5. (canceled)

6. A fragrance substance composition comprising: a mixture comprising a compound of (Ia) ##STR00036## and one or more compounds selected from 3-(4-methyl-1-cyclohex-3-enyl)-butanal, 4-(4-hydroxyphenyl) butan-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-1-(2,6,6-trimethyl-cyclohexen-1-yl)pent-1-en-3-one, (E)-4-[(1S)-1,2,6,6-tetramethylcyclohex-2-en-1-yl]-but-3-en-2-one, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, [(Z)-hex-3-enyl]methyl carbonate, 3-[(Z)-hex-3-enoxy]propanenitrile, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalene-2-yl)ethanone, spiro[1,3-dioxolan-2,5-(4,4,8,8-tetramethyl-hexahydro-3,9-methanonaphthalene)], [3R-(3,3a,6,7,8a)]-octa-hydro-6-methoxy-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene, [3R-(3,3a,7,8a)]-1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methano-azulen-5-yl)ethan-1-one, 1-(2,2,6-trimethyl-cyclohexyl) hexan-3-ol, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethylocta-1,6-dien-3-ol, (3,7-dimethylocta-1,6-dien-3-yl)acetate, (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl)acetate, (8E)-cyclohexadec-8-en-1-one, 16-oxacyclohexa-decan-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, ethoxymethoxycyclo-dodecane, 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one, and 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalene-2-yl)ethanone.

7. The fragrance substance composition according to claim 6, wherein an amount of the compound of formula (Ia) is sufficient, ##STR00037## (c) to mask or to reduce unpleasant odour impressions of another substance in the fragrance substance composition, and/or (d) to enhance pleasant odour impressions of another substance in the fragrance substance composition.

8. The fragrance substance composition according to claim 6, wherein the total amount of compound of formula (Ia) ##STR00038## is 0.01 to 10% by weight, based on the total weight of the fragrance substance composition.

9. The fragrance substance composition according to claim 6, wherein an amount of the mixture comprising the compound of (Ia), based on the total weight of the product, is in the range of from 0.01 to 10% by weight.

10. The fragrance substance composition according to claim 9, being a product selected from the group consisting of perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline and neutral detergents, textile fresheners, ironing aids, liquid detergents, powdery detergents, laundry pre-treatment agents, fabric softeners, washing soaps, washing 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, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.

11. A method for manufacturing a perfumed product, comprising: i) providing a mixture comprising a compound of formula (Ia) ##STR00039## ii) providing one or more components selected from more compounds selected from 3-(4-methyl-1-cyclohex-3-enyl)-butanal, 4-(4-hydroxyphenyl) butan-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-1-(2,6,6-trimethyl-cyclohexan-1-yl)pent-1-en-3-one, (E)-4-[(1S)-1,2,6,6-tetramethylcyclohex-2-en-1-yl]-but-3-en-2-one, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, [(Z)-hex-3-enyl]methyl carbonate, 3-[(Z)-hex-3-enoxy]propanenitrile, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalene-2-yl)ethanone, spiro[1,3-dioxolan-2,5-(4,4, 8,8-tetramethyl-hexahydro-3,9-methanonaphthalene)], [3R-(3, 3a,6, 7, 8a)]-octa-hydro-6-methoxy-3,9-tetramethyl-1H-3a,7-methanoazulene, [3R-(3, 3a,7, 8a)]-1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methano-azulen-5- yl)ethan-1-one, 1-(2,2,6-trimethyl-cyclohexyl)hexan-3-ol, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethylocta-1,6-dien-3-ol, (3,7-dimethylocta-1,6-dien-3-yl)acetate, (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl)acetate, (8E)-cyclohexadec-8-en-1-one, 16-oxacyclohexa-decan-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, ethoxymethoxycyclo-dodecane, 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthanlene-2-yl)ethanone, and iii) contacting or mixing the components provided in step ii) with a sensorially effective amount of the mixture provided in step i).

12. (canceled)

13. (canceled)

14. (canceled)

15. The method according to claim 11, wherein the amount of mixture of i) is sufficient to (a) enhance a pleasant odour impression(s) of a pleasantly smelling substance(s) and/or (b) to reduce an unpleasant odour impression(s) of an unpleasantly smelling substance(s).

16. The mixture according to claim 1 being free of compounds of (Ic) ##STR00040##

17. The mixture according to claim 16 being free of compounds of (Id) ##STR00041##

18. The method for manufacturing a mixture according to claim 4 further comprising: c) crystallizing the reaction product from step b) from aqueous alcoholic solution.

19. The fragrance substance composition according to claim 8, wherein the total amount of compound of formula (Ia) is 0.03 to 5% by weight, by weight, based on the total weight of the fragrance substance composition.

20. A method for reducing an unpleasant odor and/or for enhancing a pleasant odor comprising: adding the mixture of claim 1.

21. The method for reducing an unpleasant odor and/or for enhancing a pleasant odor of claim 20 further comprising: one or more compounds selected from 3-(4-methyl-1-cyclohex-3-enyl)-butanal, 4-(4-hydroxyphenyl) butan-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one, (E)-1-(2,6,6-trimethyl-cyclohexen-1-yl)pent-1-en-3-one, (E)-4-[(1S)-1,2,6,6-tetramethylcyclohex-2-en-1-yl]-but-3-en-2-one, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, [(Z)-hex-3-enyl]methyl carbonate, 3-[(Z)-hex-3-enoxy]propanenitrile, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalene-2-yl)ethanone, spiro[1,3-dioxolan-2,5-(4,4, 8,8-tetramethyl-hexahydro-3,9-methanonaphthalene)], [3R-(3, 3a,6, 7, 8a)]-octa-hydro-6-methoxy-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene, [3R-(3, 3a,7, 8a)]-1-(2,3,4,7,8,8a-hexa-hydro-3,6,8,8-tetramethyl-1H-3a,7-methano-azulen-5-yl)ethan-1-one, 1-(2,2,6-trimethyl-cyclohexyl)hexan-3-ol, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethylocta-1,6-dien-3-ol, (3,7-dimethylocta-1,6-dien-3-yl)acetate, (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl) acetate, (8E)-cyclohexadec-8-en-1-one, 16-oxacyclohexa-decan-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta(g)-2-benzopyran, ethoxymethoxy-cyclododecane, 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalene-2-yl)ethanone, and a mixture thereof.

22. The fragrance substance composition according to claim 6 being free of compounds of (Ic) or (Id) ##STR00042##

23. The method of claim 4, wherein the feed mixture is free of beta,alpha-cedranediol of formula (IIIc) and/or alpha,beta-cedranediol of formula (IIId), ##STR00043##

24. The method of claim 4 further comprising: providing the compound alpha,alpha-cedranediol of formula (IIIa), ##STR00044##

Description

EXAMPLE 1: PREPARATION OF A MIXTURE ACCORDING TO INVENTION

[0057] 70 kg of dimethoxypropane (95%) in 62 kg of acetone are placed in a stirring vessel and 50 kg of a starting mixture are added consisting of 99% by weight of alpha,alpha-cedranediol of formula (IIIa) as described herein, the starting mixture being free of beta,beta-cedranediol of formula (IIIb), beta,alpha-cedranediol of formula (IIIc) and alpha,beta-cedranediol of formula (IIId) as described herein. A solution consisting of 53 kg of acetone and 0.167 kg of technical sulphuric acid is then added at a temperature of not more than 30 C. for a period of 2 hours. After a further stirring time of 4 hours, the reaction mixture is adjusted to a pH of at least 8 with a slurry consisting of 1.6 kg of calcined soda in 5 kg of water.

[0058] During subsequent distillation, the low boilers are removed from the reaction mixture to such an extent that a sump temperature of 95 C. is not exceeded. When the distillation is complete, 38 kg of methyl-tert.-butyl ether are added to the distillation residue and stirred at a temperature of about 35 C. for about 30 minutes. The reaction mixture is then left to rest until a clear two-phase mixture is obtained. The aqueous phase is separated off and 12 kg of water are added to the remaining organic phase. The mixture obtained is stirred at a temperature of about 35 C. for about 30 minutes. The reaction mixture is then left to rest until a clear two-phase mixture is obtained. The aqueous phase is separated off and methyl-tert.-butyl ether is removed during subsequent distillation of the organic phase to such an extent that a sump temperature of 95 C. is not exceeded at 40 mbar. The distillation residue is taken up in 100 kg of heptane and recrystallized with an aqueous ethanolic solution.

[0059] The reaction product obtained is a mixture according to the invention, consisting of 95% by weight of the compound of formula (Ia) as described herein, the mixture being free of compounds of formula (Ib), (Ic) and (Id) as described herein.

COMPARATIVE EXAMPLE 1: MANUFACTURE OF A MIXTURE CONSISTING ESSENTIALLY OF A COMPOUND OF FORMULA (IA) AND A COMPOUND OF FORMULA (IB)

[0060] 60 kg of dimethoxypropane (95%) in 62 kg of acetone are placed in a stirring vessel and 50 kg of a mixture of isomers, 85% by weight of which consists of compounds of formula (III) as described herein (essentially alpha,alpha-cedranediol of formula (IIIa) and beta,beta-cedranediol of formula (IIIb), wherein the weight ratio of the compound of formula (IIIa) to the compound of formula (IIIb) is in the range of from 95:5 to 99.9:0.1, and further beta,alpha-cedranediol (formula (IIIc)) and alpha,beta-cedranediol (formula (IIId)), are added. The isomer mixture may also contain up to 15% by weight, based on the total weight of the isomer mixture used, of compounds of the formula (II) and (IV) to (VI). A solution consisting of 53 kg acetone and 0.167 kg technical sulphuric acid is then added at a temperature of not more than 30 C. for a period of 2 hours. After a further stirring period of 4 hours, the reaction mixture is adjusted to a pH of at least 8 using a slurry consisting of 1.6 kg of calcined soda in 5 kg of water.

[0061] During subsequent distillation, the low boilers are removed from the reaction mixture to such an extent that a sump temperature of 95 C. is not exceeded. When the distillation is complete, 38 kg of methyl-tert.-butyl ether are added to the distillation residue and stirred at a temperature of about 35 C. for about 30 minutes. The reaction mixture is then left to rest until a clear two-phase mixture is obtained. The aqueous phase is separated off and 12 kg of water are added to the remaining organic phase. The mixture obtained is stirred at a temperature of about 35 C. for about 30 minutes. The reaction mixture is then left to rest until a clear two-phase mixture is obtained. The aqueous phase is separated off and methyl-tert.-butyl ether is removed during subsequent distillation of the organic phase to such an extent that a sump temperature of 95 C. is not exceeded at 40 mbar. The distillation residue is taken up in 100 kg of heptane and recrystallized with an aqueous ethanolic solution.

[0062] The reaction product obtained is a mixture not according to the invention consisting of a total of 83% by weight of compound of formula (Ia) and compound of formula (Ib) as described herein, the weight ratio of the compound of formula (Ia) to the compound of formula (Ib) in the mixture being 95:5.

EXAMPLE 2: PARFUME OILS

[0063]

TABLE-US-00001 TABLE 1 Reaction product from comparative example 1 (VB) in the aldehyde environment using the example of the following accord: Components A (VB) B (VB) C (VB) D (VB) E (VB) F (VB) Aldehyde C11 MOA 10% 285.00 285.00 285.00 285.00 285.00 285.00 2-Methyldecanal Aldehyde C11 10% 95.00 95.00 95.00 95.00 95.00 95.00 Undecanal Aldehyde C12 MNA 10% 38.00 38.00 38.00 38.00 38.00 38.00 2-Methylundecanal Farenal 10% 76.00 76.00 76.00 76.00 76.00 76.00 2,6,10-Trimethyl-undec-9-enal Florazon 10% 209.00 209.00 209.00 209.00 209.00 209.00 3-(4-Ethylphenyl)-2,2-dimethylpropanal Limonenal 10% 95.00 95.00 95.00 95.00 95.00 95.00 3-(4-Methyl-1-cyclohex-3-enyl)-butanal Mandarin Aldehyde 10% TEC 114.00 114.00 114.00 114.00 114.00 114.00 (E)-Dodec-2-enal Ozonil 10% 38.00 38.00 38.00 38.00 38.00 38.00 Tridec-2-enenitrile Reaction product from 0.50 1.00 5.00 10.00 30.00 comparative example 1 DPG 50.00 49.50 49.00 45.00 40.00 20.00 Sum 1000.00 1000.00 1000.00 1000.00 1000.00 1000.00

TABLE-US-00002 TABLE 2 Reaction product from example 1 (B) in the aldehyde environment using the example of the following accord: Components A (B) B (B) C (B) D (B) E (B) F (B) Aldehyde C11 MOA 10% 285.00 285.00 285.00 285.00 285.00 285.00 2-Methyldecanal Aldehyde C11 10% 95.00 95.00 95.00 95.00 95.00 95.00 Undecanal Aldehyde C12 MNA 10% 38.00 38.00 38.00 38.00 38.00 38.00 2-Methylundecanal Farenal 10% 76.00 76.00 76.00 76.00 76.00 76.00 2,6,10-Trimethyl-undec-9-enal Florazon 10% 209.00 209.00 209.00 209.00 209.00 209.00 3-(4-Ethylphenyl)-2,2-dimethylpropanal Limonenal 10% 95.00 95.00 95.00 95.00 95.00 95.00 3-(4-Methyl-1-cyclohex-3-enyl)-butanal Mandarin Aldehyde 10% TEC 114.00 114.00 114.00 114.00 114.00 114.00 (E)-Dodec-2-enal Ozonil 10% 38.00 38.00 38.00 38.00 38.00 38.00 Tridec-2-enenitrile Reaction product from example 1 0.50 1.00 5.00 10.00 30.00 DPG 50.00 49.50 49.00 45.00 40.00 20.00 Sum 1000.00 1000.00 1000.00 1000.00 1000.00 1000.00

[0064] In small doses, such as in B (VB) and C (VB), a stronger and more radiant development of the scent than in A (VB) can be observed when the reaction product from comparative example 1 is added. In C (VB) and D (VB), the addition of the reaction product from comparative example 1 also highlights the typical aldehyde, greasy and metallic character of the accord. In E (VB) and F (VB), the influence of the reaction product from comparative example 1 dominates and gives the accord a strongly ambery odour (for the composition of A (VB) to F (VB) see Table 1).

[0065] In comparison, the addition of the same amount of reaction product from example 1 instead of the addition of the reaction product from comparative example 1 in B (B) to F (B) surprisingly leads to an unexpected enhancement of the corresponding effects described for B (VB) to F (VB). In particular, in D (B) the influence of the reaction product from example 1 already dominates and gives the accord a strongly ambery odour. Furthermore, the perfume oils mixed with the reaction product from example 1 appear more radiant and ambery, whereby these effects can already be perceived in the dosage C (B) (for the composition of A (B) to F (B) see Table 2).

[0066] When using the mixtures according to the invention, lower concentrations can therefore be used to achieve the same effects.

EXAMPLE 3: PERFUMED PRODUCTS

Washing Powder:

[0067]

TABLE-US-00003 weight proportions Component (1) (2) (3) Aldehyde C11 Undecylic 10% 16.00 16.00 16.00 Aldehyde C11 Undecylenic 10% 18.00 18.00 18.00 Aldehyde C12 Lauric 10% 14.00 14.00 14.00 Aldehyde C12 MNA 10% 12.00 12.00 12.00 Hexenal Trans-2 10% 4.00 4.00 4.00 Hexenyl Acetate Cis-3 4.00 4.00 4.00 Vertocitral 10.00 10.00 10.00 Magnolan 130.00 130.00 130.00 Mintonat 35.00 35.00 35.00 Dihydro Myrcenol 70.00 70.00 70.00 Orange Oil 35.00 35.00 35.00 Nerolione 10% 3.50 3.50 3.50 Cantryl 3.50 3.50 3.50 Hexyl Acetate 18.00 18.00 18.00 Jasmaprunat 18.00 18.00 18.00 Aldehyde C14 So-Called 50.00 50.00 50.00 Ethyl Methyl Butyrate-2 8.00 8.00 8.00 Manzanate 1.20 1.20 1.20 Allyl Cyclohexyl Propionate 8.00 8.00 8.00 Aprifloren 3.00 3.00 3.00 Fruitate 1.80 1.80 1.80 Ethyl Linalool 56.00 56.00 56.00 Dimethyl Benzyl Carbinyl 7.00 7.00 7.00 Butyrate Rose Abs. Type Base 30.00 30.00 30.00 Rosaphen 30.00 30.00 30.00 Damascenone Total 1.20 1.20 1.20 Damascone Alpha 1.80 1.80 1.80 Benzyl Acetate 28.00 28.00 28.00 Hedione 56.00 56.00 56.00 Hexyl Cinnamic Aldehyde 130.00 130.00 130.00 Alpha Parmanyl 3.50 3.50 3.50 Isoraldeine 70 28.00 28.00 28.00 Isoeugenyl Acetate 3.50 3.50 3.50 Agrumex HC 50.00 50.00 50.00 Ambroxide Cryst. 1.50 1.50 1.50 Reaction product from 0.80 comparative example 1 Reaction product from 0.40 0.80 example 1 Dipropylene Glycol 109.70 110.10 109.70 Sum 1000.00 1000.00 1000.00

[0068] The reaction product from comparative example 1 (column (1)) underlines the warm woody base note and supports adhesion on the laundry. In comparison, the same effect can be achieved with only half the concentration of the reaction product from example 1 compared to the reaction product from comparative example 1 (column (2)). If the same amount of reaction product from example 1 is used as the reaction product from comparative example 1 (column (3)), the odour note appears more radiant, ambery and of higher quality than that of the product described in column (1).

Shampoo:

[0069]

TABLE-US-00004 weight proportions Component (1) (2) (3) Hexenol Cis-3 2.50 2.50 2.50 Galbanum Oil 10% 5.00 5.00 5.00 Magnolan 25.00 25.00 25.00 Bergamot Oil RCO 80.00 80.00 80.00 Linalyl Acetate 120.00 120.00 120.00 Lemon Oil 80.00 80.00 80.00 Neroli Base 10.00 10.00 10.00 Lavender Oil 6.00 6.00 6.00 Thyme Oil 10% 6.00 6.00 6.00 Linalool 60.00 60.00 60.00 Phenylethyl Alcohol BA Free 20.00 20.00 20.00 Vitessence Rose De Mai 6.50 6.50 6.50 Narcisse Abs. 10% 1.30 1.30 1.30 Hedione 80.00 80.00 80.00 Jasmolactone Cis 10% 6.00 6.00 6.00 Parmanyl 10% 12.70 12.70 12.70 Ionone Beta 6.00 6.00 6.00 Methyl Ionone Gamma Pure 18.00 18.00 18.00 Irone Alpha 10% 12.00 12.00 12.00 Benzoin Siam Resin 50% 5.00 5.00 5.00 Coumarin 5.00 5.00 5.00 Iso E Super 180.00 180.00 180.00 Cashmeran 12.00 12.00 12.00 Isobutyl Quinoline 10% 6.00 6.00 6.00 Reaction product from 0.2 comparative example 1 Reaction product from 0.1 0.2 example 1 Globalide 45.00 45.00 45.00 Dipropylene Glycol 189.80 189.90 189.80 Sum 1000.00 1000.00 1000.00

[0070] The reaction product from comparative example 1 (column (1)) enhances both the top note and the adhesive woody elements in the base note. In comparison, the same effect can be achieved with only half the concentration of the reaction product from example 1 compared to the reaction product from comparative example 1 (column (2)). If the same amount of reaction product from example 1 is used as the reaction product from comparative example 1 (column (3)), the odour note appears more ambery, nourishing and cosmetic than that of the product described in column (1).