Use of ambrocenide® for intensifying a lily of the valley scent

Abstract

The present invention primarily relates to the use of one or more stereoisomers of the compound of formula (I) as described herein for modifying and/or enhancing the olfactory impression of one or more fragrances with a lily of the valley scent. The invention further relates to a new mixture comprising or consisting of one or more stereoisomers of the compound of formula (I) as described herein and two or more stereoisomers of the compound of formula (II) as described herein with a weight ratio of the stereoisomers of the compounds of formula (II) as described herein, fragrance compositions comprising or consisting of a mixture as described herein, perfumed products containing mixtures or fragrance composition as described herein, and a process for modifying and/or enhancing the lily of the valley scent of a compound of formula (II) as described herein, respectively for preparing a perfumed product as described herein.

Claims

1. A mixture comprising: one or more stereoisomer(s) of a compound of formula (I) ##STR00026## and two or more stereoisomers of a compound of formula (II) ##STR00027## wherein a weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(−) ##STR00028## to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(−) ##STR00029## is between 65:35 and 95:5.

2. The mixture according to claim 1, wherein the weight ratio of the total amount of stereoisomer(s) of the compound of the formula (I) ##STR00030## to the total amount of stereoisomers of the compound of formula (II) ##STR00031## is between 1:12000 and 1:0.5.

3. The mixture of claim 2, wherein the total amount of stereoisomer(s) of the compound of formula (I) is sufficient to enhance the olfactory impression of the two or more stereoisomers of the compound of formula (II).

4. A mixture according to claim 1 obtained by a method comprising: i) providing one or more stereoisomers of a compound of formula (I) ##STR00032## ii) providing two or more stereoisomers of a compound of formula (II) ##STR00033## wherein a weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(−) ##STR00034## to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(−) ##STR00035## is between 65:35 and 95:5, and (iii) mixing the compounds provided in steps (i) and (ii).

5. The mixture of claim 1, wherein the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(−) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(−) is between 75:25 and 85:15.

6. A mixture according to claim 1, wherein the weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(−) to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(−) is between 65:35 and 90:10; and wherein the weight ratio of the total amount of the stereoisomer(s) of the compound of the formula (I) to the total amount of the stereoisomers of the compound of formula (II) is between 1:12000 and 1:0.5.

7. A method for modifying and/or enhancing the lily of the valley scent comprising: i) providing one or more stereoisomer(s) of a compound of formula (I) ##STR00036## ii) providing two or more stereoisomers of a compound of formula (II) ##STR00037## wherein a weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(−) ##STR00038## to the total amount of compounds of the formula trans-(II)(+) and trans-(II)(−) ##STR00039## is between 65:35 and 95:5, and iii) mixing the compounds provided in steps i) and ii).

8. A fragrance composition comprising: a mixture according to claim 1, and one or more additional fragrances 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]propannitrile, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexa-hydronaphthalen-2-yl)ethanone, spiro[1,3-dioxolane-2,5′-(4′,4′,8′,8′-tetramethyl-hexahydro-3′,9′-methanonaphthalene)], [3R-(3α,3a β,6β,7β,8aα)]-octa-hydro-6-methoxy-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen, [3R-(3α,3aβ,7β,8aα)]-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, 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-hydronaphthalen-2-yl)ethanone.

9. The fragrance composition according to claim 8, wherein the total amount of stereoisomer(s) of the compound of formula (I) ##STR00040## is sufficient to modify and/or enhance the olfactory impression of the two or more stereoisomers of the compound of formula (II) ##STR00041##

10. The fragrance composition according to claim 9, wherein the total amount of stereoisomer(s) of the compound of formula (I) ##STR00042## is 0.0001 to 10% by weight, based on the total weight of the fragrance composition.

11. The fragrance composition according to claim 10, wherein the total amount of stereoisomer(s) of the compound of formula (I) is 0.001 to 5% by weight, based on the total weight of the fragrance composition.

12. A product comprising a mixture according to claim 1 in a sensory effective amount, wherein the amount of the mixture, based on the total weight of the product, is in the range of 0.1 to 20% by weight.

13. The product of claim 12 being selected from perfume extraits, eau de parfums, eau de toilettes, shaving lotions, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, acidic, alkaline and neutral detergents, textile fresheners, ironing aids, liquid detergents, powdery detergents, laundry pre-treatments, fabric softeners, laundry 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.

14. A fragrance composition comprising from 0.001 to 1 wt. % of a mixture according to claim 1.

15. A method for providing and/or enhancing a lily of the valley scent to a product, the method comprising: (a) identifying a product to which a lily of the valley scent is to be provided and/or enhanced; and (b) incorporating the mixture according to claim 1 into the product in an amount sufficient to provide and/or enhance the lily of the valley scent.

16. The method according to claim 7, further comprising verifying that the lily of the valley scent of the compounds of formula (II) has been modified and/or enhanced by the compounds of formula (I).

17. The method according to claim 7, wherein a weight ratio of the total amount of stereoisomer(s) of the compound of formula (I) ##STR00043## to the total amount of stereoisomers of the compound of formula (II) ##STR00044## is between 1:12000 and 1:0.5.

18. The method of claim 7 further comprising: (iv) providing one or more other components of a product to be manufactured; and (v) contacting the other components provided in step (ii) with a sensory effective amount of the mixture of step (iii).

19. A mixture comprising: one or more stereoisomer(s) of a compound of formula (I) ##STR00045##  ; and two or more stereoisomers of a compound of formula (II) ##STR00046## wherein a weight ratio of the total amount of compounds of the formula cis-(II)(+) and cis-(II)(−) ##STR00047## to the total amount of compounds of the formula trans-(II)(+) and trans-(II) (−) ##STR00048## is between 65:35 and 95:5; and wherein the mixture is free of additional fragrances other than the one or more steroisomer(s) of the compound of formula (I) and the two or more stereoisomers of a compound of formula (II).

20. The mixture according to claim 19 consisting of the one or more stereoisomer(s) of a compound of formula (I) and the two or more stereoisomers of a compound of formula (II).

Description

EXAMPLES

Preferred Mixtures of Pyranol and Ambrocenide®

Mixture 1

(1) TABLE-US-00001 PYRANOL 1,000.00 AMBROCENIDE ® 0.1

(2) Effect: The lily of the valley scent of the pyranol is enhanced and more concise, which goes along with a higher value.

Mixture 2

(3) TABLE-US-00002 PYRANOL 1,000.00 AMBROCENIDE ® 1

(4) Effect: The lily of the valley scent of pyranol becomes more substantive and natural, making the mixture 2 appear more valuable.

Perfume Oils 1

(5) TABLE-US-00003 A B C D ALDEHYD C14 SOG 3.00 3 3 3 AMBROXIDE 15 15 15 15 BENZOE SIAM ABS. 30 30 30 30 BENZYLACETAT FG 2 2 2 2 BHT JONOL 2 2 2 2 CASHMERAN 20 20 20 20 CUMARIN 7 7 7 7 DECALACTON GAMMA 4 4 4 4 DIPROPYLENGLYCOL 69.5 69.5 69.5 69.5 EBANOL 15 15 15 15 ETHYLENBRASSYLATE 150 150 150 150 ETHYLMALTOL 10 10 10 10 FLOROSA 120 PYRANOL 120 HEXENOL CIS-3 10% DPG 8 8 8 8 HEXENYLACETATE CIS-3 1 1 1 1 INDOL FF 1% DPG 5 5 5 5 ISO E SUPER 320 320 320 320 ISOEUGENOL 10% DPG 1.5 1.5 1.5 1.5 JASMIN ABS. SAMBAC REF.A 50% BB 1.5 1.5 1.5 1.5 JASMON CIS 1 1 1 1 METHYLANTHRANILATE 10% DPG 0.5 0.5 0.5 0.5 MUSCENONE 7 7 7 7 MUSCONE 7 7 7 7 NORLIMBANOL 15 15 15 15 POLYSANTOL (MYSANTOL) 30 30 30 30 RED BERRIES EXTRACT 5 5 5 5 SANDRANOL ® 150 150 150 150 Mixture 1 120 Mixture 2 120 TOTAL 1000 1000 1000 1000

(6) Perfume oil A: Standard fragrance composition with Florosa® as lily of the valley fragrance

(7) Perfume oil B: Florosa® from perfume oil A is replaced by pyranol. The fragrance of perfume oil B is less floral, less radiant and loses complexity compared to perfume oil A. The fragrance of perfume oil A is less floral, less radiant and less complex.

(8) Perfume oil C: Florosa® from perfume oil A is replaced by mixture 1 (as described above). Perfume oil C's fragrance is more radiant than perfume oil B, has more body and better hedonics.

(9) Perfume oil D: Florosa® from perfume oil A is replaced by mixture 2 (as described above). The fragrance of perfume oil D is stronger and more substantive compared to perfume oil B. In addition, perfume oil D is also more radiant and complex, and overall more performant than perfume oil A.

Perfume Oils 2

(10) TABLE-US-00004 E F G AMAROCIT ® 10 10 10 AMBRETTOLIDE 1.5 1.5 1.5 AMBROXIDE 0.5 0.5 0.5 AMYRISOEL 2.5 2.5 2.5 AURELIONE ® 25 25 25 BENZYLSALICYLATE 9 9 9 BERGAMOT OIL BERGAPTEN FREE 40 40 40 CITRAL FF 1.5 1.5 1.5 CITRONELLOL L 1.5 1.5 1.5 CLARITONE ® 5 5 5 DIMETHYLBENZYLCARBINYLBUTYRATE 10% DPG 1 1 1 ETHYLENBRASSYLATE 50 50 50 FLOROPAL 10% DPG 3 3 3 FLOROSA 90 GLOBALIDE ® 50 50 50 HEDION HC/30 400 400 400 HELIOTROPIN/PIPERONAL 20 20 20 HEXYLCINNAMICALDEHYDE ALPHA 10% DPG 1 1 1 ISO E SUPER 200 200 200 ISOBORNYLCYCLOHEXANOL 10 10 10 ISORALDEIN 95 30 30 30 LINALOOL 12 12 12 MAGNOLAN 23 23 23 MANDARIN OIL 6 6 6 SANDALWOOD OIL AUSTRALIA PURE 7.5 7.5 7.5 Mixture 1 90 Mixture 2 90 TOTAL 1000 1000 1000

(11) Perfume oil E: Standard fragrance composition with Florosa® as lily of the valley fragrance

(12) Perfume oil F: Florosa® is replaced by mixture 1 (as described above); the olfactory improvement of the fragrance is low, but by replacing Florosa® with mixture 1, raw material costs can be saved.

(13) Perfume oil G: Florosa® is replaced by mixture 2 (as described above); the fragrance of fragrance composition G is stronger, more substantive and has more floral character than that of Compositions E and F.

Perfumed Products

Washing Powder

(14) TABLE-US-00005 AGRUMEX LC 150 AMBERWOOD ® F 12 BENZYLACETON 50 CITRONELLOL 950 2 CITRONITRIL 2 CYCLAMENALDEHYDE 1 DIHYDROMYRCENOL 200 DIPROPYLENGLYCOL 3 GERANIOL SUPRA 1 HERBYLPROPIONATE 80 HEXYLACETATE 45 IONON ALPHA 2 IONON BETA 6 ISO E SUPER 250 ISODAMASCON ® 1 LINALOOL 20 MACROLIDE ® SUPRA 10 MAGNOLAN 2 MANZANATE 1 NEROLIONE 10% DPG 2 ORANGE OIL 15 PHENIRAT ® 50 PHENYLACETALDEHYDE 1 DIMETHYLACETAL PYROPRUNATE 2 ROSE OXIDE 1 SANDRANOL ® 20 UNDECAVERTOL 5 VERTOCITRAL 1 YSAMBER ® K 5 Mixture 1 60

(15) The perfume oil gives the washing powder the typical smell that one expects from this product. It transmits the message of cleanliness and freshness. In this case, the fragrance starts with a combination of aldehydes and citrus that reflect the freshness. Followed by the floral heart, which is the caring character. The base note consists of long-lasting components that have a woody, amber and musky character to give the impression of fresh laundry even after days.

Shampoo

(16) TABLE-US-00006 AGRUMEX HC 80 ALDEHYDE C14 SOG 50 ALDEHYDE C16 SOG. 1 AMBROXIDE 4 ANISALDEHYDE CLEAN 16 APPLE GREEN AROMABASE 15 APRIFLOREN ® 1 BERGAMOT OIL AUTHENTIC 20 CITRONELLOL 950 40 CITRONELLYLACETATE EXTRA 10 DECALACTON GAMMA 5 DIHYDROMYRCENOL 100 DIPROPYLENGLYCOL 8 ETHYLVANILLIN 10% DPG 4 EUGENOL NAT. 3 FRAMBINON ® 10% DPG 6 GERANYLACETATE 60 20 GERANYLTIGLINATE 5 GLOBALIDE ® 25 HEDION 60 HEXENAL TRANS-2 10% DPG 6 HEXENYLACETATE CIS-3 10% 9 DPG HEXYLACETATE 50 HEXYLSALICYLATE 15 INDOFLOR ® KRIST. 10% DPG 2 ISO E SUPER 20 ISORALDEIN 70 15 JASMIN 61 TYPE BASE 20 LINALOOL 60 LINALYLACETATE 150 PHENIRAT ® 50 ROSE DE MAI-BASE 30 ROSE OXIDE L 5 SANDRANOL ® 15 VERTOCITRAL 10 Mixture 2 70

(17) The perfume oil as a fragrance conveys the expectations one has of the product. In this case of a shampoo, you expect cleansing and care. This is conveyed by the fragrance. A clean apple/citrus combination reflects the cleansing part, while the heart of the fragrance (floral with fruity notes) is the caring aspect. The fragrance experience is rounded off by warm, woody and musky components.