Compounds having protected hydroxy groups

Details Compounds having protected hydroxy groups Compounds having protected hydroxy groups

2002-06-12

2003-09-30

Hardee, John (Department: 1751)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S273000

Reexamination Certificate

active

06627763

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a new group of compounds having protected hydroxy groups which are precursors for organoleptic compounds, such as fragrances and masking agents and antimicrobial compounds.
BACKGROUND OF THE INVENTION
A principal strategy currently employed in imparting odors to consumer products is admixing a fragrance directly into the product. There are, however, several drawbacks to this strategy. The fragrance material can be too volatile, resulting in undesired fragrance loss during manufacturing, storage, and use. Many fragrance materials also are unstable over time. This, again, results in undesired fragrance loss during storage.
In many consumer products, it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes with cyclodextrins have been used to help decrease volatility, improve stability and provide slow-release properties. However, these methods are, for a number of reasons, often not successful. In addition, cyclodextrins are too expensive to use commercially.
Fragrance precursors for scenting fabrics which are washed in the presence of lipase-containing detergents are described in WO 95/04809. The fragrance precursors contained in the detergent and/or in the softener are cleaved by the lipase and a single odoriferous compound, either an odoriferous alcohol or aldehyde or ketone, is yielded. Thereby, a prolonged scenting effect on the fabric is reportedly obtained.
In summary, the methods and compositions set forth above suffer from various drawbacks which make them less desirable for use as long lasting, e.g., organoleptic and/or antimicrobial compounds.
Accordingly, one object of the present invention is to provide new compounds which are precursors having different activities.
It is another object of the present invention to provide compounds that are cleaved under different activating conditions.
A further object of the invention is to provide new compounds which are stable under transport and storage conditions.
A further object of the present invention is to provide a precursor molecule that supplies different active compounds simultaneously or successively.
These and other objects of the present invention will become apparent from the present disclosure and claims.
SUMMARY OF THE INVENTION
The present invention relates to compounds of formula (I):
wherein Y is
m is an integer of 1 or greater;
n is 1, 2 or 3;
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
represent independently hydrogen, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic radicals which can additionally contain one or more
 whereby one or two rings can be built by the combination of the respective R
1
to R
6
groups and these ring(s) can be substituted with one or more alkyl group;
X is —OR
7
and R
7
is the residue of an alcohol R
7
OH, or the residue of the enol form of an aldehyde or ketone, or X is a primary or secondary amino group forming an amide;
 q is the same or greater than m;
R
8
is hydrogen, a straight or branched, unsubstituted or substituted alkyl-, alkenyl-, cycloalkyl-, cycloalkenyl- or aromatic radical which optionally includes and/or is substituted with one or more heteroatoms, and/or group(s) including a heteroatom, preferably by —CO—, OCOR
7
, COOR
7
, COY, Si and/or N;
R
9
is the residue —OR
12
of an alcohol of formula R
12
OH or the residue of the enol form of an aldehyde or ketone or has the definition given for Y and R
9
where Y can be the same or different and optionally includes and/or is substituted with a heteroatom, and/or group(s) including a heteroatom;
R
10
and R
11
represent independently hydrogen, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or an aromatic residue which optionally includes and/or is substituted with one or more heteroatoms, and/or group(s) containing a heteroatom.
Another embodiment is a composition including a compound of formula (I) as a precursor for at least one organoleptic compound.
Another embodiment is a laundry composition including a compound of formula (I) which forms an organoleptic compound and/or a fluorescent coumarin when activated.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of formula (I) are not limited to any particular stereoisomers. Thus, all possible stereoisomers (E/Z isomers, enantiomers, diastereomers) and all mixtures thereof are included within the scope of the present invention.
The compounds of formula (I) are virtually odorless under room temperature, atmospheric conditions and about 20 to 100% relative humidity. However, under activating conditions, they are cleaved and one or more active compounds with organoleptic and/or antimicrobial properties are generated.
As used herein, the phrases “activating conditions” or “activated” are used interchangeably and are intended to mean those conditions which lead to cleavage of the compounds of formula (I) and the formation of “active,” i.e., organoleptic and/or antimicrobial agents. For example, the following activating conditions lead to cleavage of compounds of formula (I) and to formation of the desired active compounds: skin bacteria, especially axilla bacteria; enzymes such as protease or lipase; elevated temperature; acidic or alkaline pH-values; and/or light.
The compounds of formula (I), upon cleavage, form lactones and optionally aldehydes, ketones, and/or alcohols having organoleptic and/or antimicrobial activity. Thus, the compounds of formula (I) permit the development of useful consumer products with enhanced organoleptic and/or microbiological properties. Further, the compounds of formula (I), upon cleavage can generate fluorescent coumarins useful as optical brighteners.
The compounds of formula (I) of the present invention are cleaved under activating conditions in two successive steps. First the “protective group” Z is removed resulting in a hydroxyester according to the following reaction:
The hydroxyester (II) decomposes into one or more organoleptic lactone(s), and one or more alcohol(s), amine(s), aldehyde(s) and/or ketone(s).
In the present invention, Z is a protective group which prevents the hydroxy ester Y—H(II) from premature cyclisation to an organoleptic lactone (III). At the same time, Z can generate one or more additional organoleptic compound(s).
In the following reaction, cleavage of a &bgr;-ketoester of formula (I) is shown.
wherein,
1 is Z—Y, a protected hydroxy ester (&bgr;-ketoester);
2 is ZH, a hydroxyester;
3 is an organoleptic lactone;
4 is an organoleptic alcohol;
5 is an &bgr;-ketoacid; and
6 is an organoleptic ketone.
Thus, one compound of formula (I) can be cleaved to form, under activating conditions, three different organoleptic compounds.
When Z is
it is the residue of an odorless or antimicrobial acid optionally substituted by groups yielding, upon cleavage, one or more organoleptic compounds. Examples of esters in which R
8
is an odorless acid are:
tetradecanoic acid 1-(2-hex-3-enyloxycarbonyl-ethyl)-heptyl ester;
tetradecanoic acid 1-[2-(3,7-dimethyl-octa-2,6-dienyloxycarbonyl)-ethyl]-octyl ester;
benzoic acid 1-[2-(3,7-dimethyl-octa-2,6-dienyloxycarbonyl)-ethyl]-octyl ester;
dodecanoic acid 1-[2-(3,7-dimethyl-oct-6-enyloxycarbonyl)-ethyl]-heptyl ester;
succinic acid 1-[2-(1,5-dimethyl-1-vinyl-hex-4-enyloxycarbonyl)-ethyl]-heptyl ester hex-3-enyl ester is a compound wherein R
8
is COR
7
;
succinic acid bis-{1-[2-(3,7-dimethyl-octa-2,6-dienyloxycarbonyl)-ethyl]-octyl} ester with R
8
being COY.
When Z is
R
9
is preferably the residue of an organoleptic compound or Y as defined previously. Examples of carbonates in which R
9
is an organoleptic compound are:
4-phenethyloxycarbonyloxy-decanoic acid 3,7-dimethyl-oct-6-enyl-ester;
4-phenethyloxycarbonyloxy-decanoic acid hex-3-enyl ester;
4-hex-3-enyloxycarbonyloxy-undecanoic acid 3,7-dimethyl-octa-2,6-dienyl ester;
4-phenethyloxycarbonyloxy-undecanoic acid 3,7-dimethyl-octa-2,6-dienyl ester;
4-{1-[2-(1,1,5-trimethyl

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