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US 2026/0285828 A1Published application
Photolabile cyclic acetals and ketals for the light-induced delivery of active aldehydes and ketones
AssigneeFirmenich SA
InventorsKimberly BRADY, Gary WOMACK, Andreas HERRMANN
Life of this patent
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Abstract
The present invention relates to compounds of formula (I), a delivery system based on photosensitive cyclic acetal or ketal compounds capable of liberating in a controlled manner active volatile carbonyl compounds into the surrounding upon exposure to light. Furthermore, the present invention relates to the use of said compounds in perfumery, as well as the perfuming compositions or perfumed consumer products comprising the invention's compounds.
Claims19
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein
- n is 0 or 1;
- R1 represents a C1-18 hydrocarbon group, optionally comprising one to three oxygen atoms and/or one to two nitrogen atoms and/or one sulfur atom;
- R2 represents a hydrogen atom or a R1 group;
- or R1 and R2, when taken together, form a C5-16 cycloalkyl, C5-16 cycloalkenyl, C4-14 heterocycloalkyl or C4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C1-15 alkyl, C2-15 alkenyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, carboxylic acid and/or C1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom;
- R3 and R4 represent, independent of each other, a hydrogen atom, a C1-6 alkoxy group or a C1-12 alkyl group, optionally substituted by a hydroxy, C1-6 alkoxy or oxo group, or, two adjacent R3 groups, when taken together, are a C3-8 linear alkanediyl group optionally substituted by one or more of a hydroxy, C1-3 alkyl and/or C1-3 alkoxy group;
- R5 represents a hydrogen atom or a C1-6 hydrocarbon group, or R4 and R5, when taken together, represent a C1-4 linear, branched or cyclic alkanediyl group, optionally comprising one oxygen atom;
- R6 represents a hydrogen atom or a methyl group;
- R7, R8 and R9 represent, independent of each other, a hydrogen atom or a C1-6 alkyl group;
- R10 represents a C1-6 alkyl group, a C2-6 alkenyl group, a C3-8 cycloalkyl group, a C5-8 cycloalkenyl group or a phenyl group;
- each optionally substituted by one or more hydroxy, C1-6 alkoxy or C1-6 alkyl groups;
- the groups R1 and R2 have in total at least 4 carbon atoms;
- and
- provided that 1,3-diphenyl-3-(1,4-dioxaspiro[4.5]decan-2-yl)propan-1-one and 1,3-bis(4-methoxyphenyl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)propan-1-one are excluded.
11 more elements
(canceled)
A method to release from a precursor compound, compounds selected from the group consisting of
- a) a carbonyl compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, wherein R1 represents a C1-18 hydrocarbon group, optionally comprising one to three oxygen atoms and/or one to two nitrogen atoms and/or one sulfur atom;
- R2 represents a hydrogen atom or a R1 group;
- or R1 and R2, when taken together, form a C5-16 cycloalkyl, C5-16 cycloalkenyl, C4-14 heterocycloalkyl or C4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C1-15 alkyl, C2-15 alkenyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, carboxylic acid and/or C1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom;
- b) a ketone of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein R3 and R4 represent, independent of each other, a hydrogen atom, a C1-6 alkoxy group or a C1-12 alkyl group, optionally substituted by a hydroxy, C1-6 alkoxy or oxo group, or, two adjacent R3 groups, when taken together, are a C3-8 linear alkanediyl group optionally substituted by one or more of a hydroxy, C1-3 alkyl and/or C1-3 alkoxy group;
- R5 represents a hydrogen atom or a C1-6 hydrocarbon group, or R4 and R5, when taken together, represent a C1-4 linear, branched or cyclic alkanediyl group, optionally comprising one oxygen atom;
- R6 represents a hydrogen atom or a methyl group;
- wherein the precursor compound is a compound of formula (I)
- in the form of any one of its stereoisomers or a mixture thereof, and wherein R1, R2, R3, R4, R5 and R6 have the same meaning as defined above;
- n is 0 or 1;
- R7, R8 and R9 represent, independent of each other, a hydrogen atom or a C1-6 alkyl group;
- and R10 represents a C1-6 alkyl group, a C2-6 alkenyl group, a C3-8 cycloalkyl group, a C5-8 cycloalkenyl group or a phenyl group;
- each optionally substituted by one or more hydroxy, C1-6 alkoxy or C1-6 alkyl groups;
- by exposing the precursor compound of formula (I) to light and to an environment wherein the compound is hydrolyzed.
12 more elements
Dependencies are inferred from the claim text.