IP Library Granted Patent US 7,601,682
Granted Patent B2
US 7,601,682 · App. 11/967,652 · Granted Oct 13, 2009

Mixtures of 3-(4-methylcyclohex-3-enyl)butyraldehyde and Ambrocenide® and corresponding uses and methods

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Quick Facts
Patent No.
US 7,601,682
App. No.
11/967,652
Granted
Oct 13, 2009
Kind
B2
Abstract

Mixtures are described which comprise or consist of 3-(4-methylcyclohex-3-enyl)butyraldehyde (limonenal) and (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole (Ambrocenide®), the weight ratio of limonenal to Ambrocenide® being in the range from 150:1 to 2500:1.

Claims (13)

1. A mixture comprising 3-(4-methylcyclohex-3-enyl)butyraldehyde (limonenal) and (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole, wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 150:1 to 2500:1.

2. The mixture of claim 1 consisting essentially of 3-(4-methylcyclohex-3-enyl)-butyraldehyde (limonenal) and (4aR,5R7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,3-methanoazuleno(5,6-d)-1,3-dioxole, wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 150:1 to 2500:1.

3. The mixture of claim 1 consisting of 3-(4-methylcyclohex-3-enyl)butyraldehyde (limonenal) and (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole, wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 150:1 to 2500:1.

4. The mixture of claim 1 , wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 600:1 to 2500:1.

5. The mixture of claim 1 , wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 800:1 to 2500:1.

6. The mixture of claim 2 , wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 800:1 to 2500:1.

7. The mixture according to claim 1 , further comprising one or more diluents or solvents selected from the group consisting of ethanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate (BB) and benzyl acetate.

8. The mixture of claim 7 , wherein the weight ratio of (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole to the total amount of said diluent(s) or solvent(s) is in the range from 1:99 to 1:1.

9. A fragrance mixture comprising the mixture of claim 1 , and further comprising at least an equal proportion by weight of one or more other fragrances.

10. A method of masking the fatty olfactory note of limonenal comprising: mixing limonenal with an amount of (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole the partially or completely masks the fatty olfactory note of limonenal, wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole in the mixture is in the range from 150:1 to 2500:1.

11. The method of claim 10 , wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole in the mixture is in the range from 600:1 to 2500:1.

12. A method of preparing a fragrance composition comprising the steps of mixing together 3-(4-methylcyclohex-3-enyl)butyraldehyde (limonenal); (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole, and one or more other fragrances, wherein the weight ratio of limonenal to (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole is in the range from 150:1 to 2500:1.

13. The method of claim 12 , wherein the fragrance composition has a fresh, citrus-like note.

Assignments (3)
MERGER Recorded Apr 22, 2011
From: SYMRISE GMBH & CO. KG
To: SYMRISE AG
Reel/Frame 026171/0582 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF ASSIGNEE AND TITLE OF APPLICATION ON NOTICE OF RECORDATION PREVIOUSLY RECORDED ON REEL 020622 FRAME 0087. ASSIGNOR(S) HEREBY CONFIRMS THE FRED NARASCHKEWITZ (02/29/2008) AND MARCUS EH (03/03/2008). Recorded Sep 1, 2009
From: NARASCHKEWITZ, FRED; EH, MARCUS
To: SYMRISE GMBH & CO. KG
Reel/Frame 023178/0135 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 10, 2008
From: NARASCHKEWITZ, FRED; EH, MARCUS
To: SYMRISE GMBH & CO.
Reel/Frame 020622/0087 →