Compounds for the controlled release of active aldehydes

• US 20050026998A1
• Filed: 08/31/2004
• Published: 02/03/2005
• Est. Priority Date: 03/28/2002
• Status: Abandoned Application

• Current Assignee: Firmenich SA (DSM-Firmenich AG)
• Original Assignee: Firmenich SA (DSM-Firmenich AG)
• Inventors: Womack, Gary B., Vermeer, Robert C., Kalinoski, Henry T.
• Application Number:
  US10/930,634
• Publication Number:
  US 20050026998A1
• Time in Patent Office: Days
• US Class Current: 514/452
• CPC Class Codes: A23L 27/2052 having oxygen or sulfur as the only hetero atoms
• CPC Class Codes: A61K 8/498 having 6-membered rings or their condensed derivatives, e.g. coumarin
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: C07D 319/06 not condensed with other rings
• CPC Class Codes: C11B 9/008 the hetero rings containing six atoms

Abstract

The present invention relates to the field of perfumery. More particularly, it concerns aldoxane compounds of formula
which compounds are capable of protecting an active aldehyde R¹CHO, for example, a perfumery or flavor aldehyde, from a chemically aggressive medium into which they have to be added, and then of releasing the active aldehyde at the desired moment. The present invention concerns also the use of such compounds in perfumery or in the flavor industry as well as the compositions or articles associated with these aldoxane compounds.

Claims

1. A composition of matter comprising at least one compound of formula

2. The composition of matter according to claim 1, wherein the active ingredient of formula (I) includes

R¹, R² and Y as defined as in claim 1;

R³ representing a C₁ to C₁₆ linear, branched, cyclic or poly-cyclic saturated, unsaturated, aromatic or alkylaryl hydrocarbon radical, with the hydrocarbon radical optionally comprising up to three oxygen or nitrogen atoms and optionally being substituted; and

R⁴ represents a Y group or R⁴ and R³ are bonded together to form a saturated or unsaturated ring having 5 to 15 carbon atoms, the ring optionally being substituted.

3. The composition of matter according to claim 1, wherein the active ingredient of formula (I) includes

R¹ representing an organic residue derived from an active aldehyde of formula R¹CHO selected from the group consisting of hydroxycitronellal, citronellal, 3-(4-methoxyphenyl)-2-methylpropanal, the linear C₈ to C₁₂ alkyl aldehydes, 3-(4-isopropylphenyl)-2-methylpropanal, 3-(4-tert-butylphenyl)-2-methylpropanal, 4- and 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 3-(4-tert-butylphenyl)propanal, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 3- and 4-(3,3-dimethyl-5-indanyl)propanal, 8(9)-methoxy-tricyclo[5.2.1.0.(2,6)]decane-3(4)-carbaldehyde and 3-phenylbutanal;

R² representing a R¹ group, a hydrogen atom or a C₁ to C₁₆ linear, branched, cyclic or polycyclic alkyl, alkenyl or alkylaryl hydrocarbon radical, with the hydrocarbon radical optionally being substituted, or a C₅ to C₆ aromatic ring, optionally comprising up to three oxygen or nitrogen atoms and optionally being substituted;

R³ represents a C₁ to C₁₆ linear, branched, cyclic or poly-cyclic saturated, unsaturated, aromatic or alkylaryl hydrocarbon radical, with the hydrocarbon radical optionally comprising up to three oxygen or nitrogen atoms and optionally being substituted; and

R⁴ represents a hydrogen atom or a R³ group;

or R⁴ and R³ are bonded together to form a saturated or unsaturated ring having 5 to 10 carbon atoms, with the ring optionally being substituted.

4. The composition of matter according to claim 1, wherein the active ingredient of formula (I) includes

R¹ representing an organic residue derived from an active aldehyde of formula R¹CHO selected from the group consisting of hydroxycitronellal, citronellal, 3-(4-methoxyphenyl)-2-methylpropanal, the linear C₈ to C₁₂ alkyl aldehydes, 3-(4-isopropylphenyl)-2-methylpropanal, 3-(4-tert-butylphenyl)-2-methylpropanal, 4- and 3-(4-hydroxy-4-methylpentyl)-3 -cyclohexene-1 -carbaldehyde, 3-(4-tert-butylphenyl)propanal, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 3- and 4-(3,3-dimethyl-5-indanyl)propanal, 8(9)-methoxy-tricyclo[5.2.1.0.(2,6)]decane-3(4)-carbaldehyde and 3-phenylbutanal;

and

R² and R³ represent a C₃ to C₁₀ linear, branched, cyclic or polycyclic saturated, unsaturated, aromatic or alkylaryl hydrocarbon radical, and R⁴ represents a hydrogen atom or a methyl or ethyl group.

5. The composition of matter according to claim 1, wherein the active ingredient of formula (I) is susceptible of being obtained by a reaction comprising the following step:

a) mixing together, the three aldehydes of the formulae (II), (III) and (IV),

wherein R¹, R², R³ and R⁴ have the meaning as defined in formula (I), in the presence of a base, such as an alkaline hydroxide or C₁ to C₄ alkoxide, and a temperature comprised between −

10°

C. and +10°

C., preferably between 0°

C. and 5°

C., and aldehydes (III) and (IV) being in at least an equimolar amount in respect of aldehyde (II);

or

b) reacting, at a temperature comprised between −

10°

C. and 50°

C., preferably between 0°

C. and 30°

C., an active aldehyde (II), as defined hereinabove, with an aldol of formula

wherein R², R³ and R⁴ have the meaning as defined in formula (I), the latter being susceptible of being obtainable by an aldol reaction between an aldehyde of formula (III) and an aldehyde of formula (IV).

6. A compound of formula (I) as defined in claim 1, provided that 5-methyl-2,6-bis(1-methylethyl)-1,3-dioxan-4-ol, 2,6-diethyl-5-methyl-1,3-dioxan-4-ol, 2,6-dimethyl-1,3-dioxan-4-ol, 6-hexyl-2-(1-methylethyl)-1,3-dioxan-4-ol, 5,5,6-trimethyl-2-(1-methylethyl)-1,3-dioxan-4-ol, 5,5-dimethyl-2,6-bis(1-methylethyl)-1,3-dioxan-4-ol, 2,6-dibenzyl-5-phenyl-1,3-dioxan-4-ol, 2-ethyl-6-methyl-1,3-dioxan-4-ol, 2-(1-methylethenyl)-1,3-dioxan-4-ol, 6-hexyl-2-(2-octanol-1-yl)-1,3-dioxan-4-ol and 5-ethyl-2,6-dipropyl-1,3-dioxan-4-ol are excluded.

7. A composition of matter comprising at least one compound of formula (I), as defined in claim 1, and at least one perfumery or flavor carrier.

8. A perfumed article comprising:

i) at least one compound of formula (I), as defined in claim 1;

and

ii) a consumer product base.

9. The perfumed article according to claim 8, wherein the consumer product base is in the form of a solid or liquid detergent, a fabric softener, a perfume, a cologne, an after-shave lotion, a perfumed soap, a shower or bath salt, mousse, oil or gel, a hygiene product, a hair care product, a shampoo, a body-care product, a deodorant, a antiperspirant, an air freshener, a cosmetic preparation, a fabric refresher, an ironing water, a paper, a wipe or a bleach.

10. A perfumed article comprising:

i) the composition as defined in claim 7;

and

ii) a consumer product base.

11. The perfumed article according to claim 10, wherein the consumer product base is in the form of a solid or liquid detergent, a fabric softener, a perfume, a cologne, an after-shave lotion, a perfumed soap, a shower or bath salt, mousse, oil or gel, a hygiene product, a hair care product, a shampoo, a body-care product, a deodorant, a antiperspirant, an air freshener, a cosmetic preparation, a fabric refresher, an ironing water, a paper, a wipe or a bleach.

12. A flavored article comprising:

i) at least one compound of formula (I), as defined in claim 1;

and

ii) a foodstuff base.

13. The flavored article according to claim 12, wherein the foodstuff base is in the form of a dry powder or concentrated composition for instant beverage, a chewing gum or a baking application.

14. A flavored article comprising:

i) a composition as defined in claim 7;

and

ii) a foodstuff base.

15. The flavored article according to claim 14, wherein the foodstuff base is in the form of a dry powder or concentrated composition for instant beverage, a chewing gum or a baking application.

17. A method for perfuming a surface or object which comprises adding a composition according to claim 1, which includes a perfume base comprising an active aldehyde, to a chemically aggressive medium, and then releasing the active aldehyde at the desired moment, wherein the composition protects the aldehyde from degradation due to exposure to the chemically agressive medium.

18. A method for flavoring an edible substance which comprises adding a composition according to claim 1, which includes a flavor base comprising an active aldehyde, to a chemically aggressive medium, and then releasing the active aldehyde at the desired moment, wherein the composition protects the aldehyde from degradation due to exposure to the chemically agressive medium.

16. A process for the perfuming of a surface or a process for intensifying, prolonging or deferring the diffusion effect of the characteristic fragrance of a fragrant aldehyde on a surface, which comprises treating the surface with at least one compound of formula (I)