Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
1999-12-28
2001-10-30
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S008000, C512S011000, C512S020000, C512S025000, C512S006000, C510S101000
Reexamination Certificate
active
06310033
ABSTRACT:
This invention relates to the use of substituted phenylpentane derivatives as perfumery materials, and includes novel perfumery compounds.
BACKGROUND OF THE INVENTION
Many compounds have been described in the literature as-fragrance materials. As is the case with many classes of compounds having varied utilities, of the many compounds that are known to possess pleasing fragrance notes, only a very small portion are utilized commercially. There are several reasons for this, notably toxicological constraints, environmental considerations, biodegradability, performance, and cost effectiveness. While all of these factors must be carefully weighed in consideration of whether to introduce a new fragrance material, perhaps the most important factors are performance and cost. Performance properties include odor activity, notes, and aesthetics; substantivity; and solubility. The cost effectiveness involves manufacture costs and the amount of the compound required to impart fragrance to a consumable product. Of course, the lower the amount of fragrance material required, the higher its cost effectiveness. Many materials have met some of the above-mentioned criteria, yet have not been successful because of disappointing ratios of cost versus performance.
It must further be borne in mind that, because fragrance materials are by nature utilized in comparatively small quantities, only a very few benefit from the cost efficiency of large-scale production. All of these factors, combined with the tendency in many countries to take a more rigid regulatory position concerning ingredients in consumable products, have acted to hamper the introduction of new fragrance materials in recent years.
There is an on-going need for new fragrance materials that can be readily synthesized from relatively inexpensive raw materials, meet the criteria set forth above, possess unique fragrance notes and, perhaps most importantly, are cost-effective in use. Such materials are provided in accordance with the present invention.
SUMMARY OF THE INVENTION
The invention relates to the use of substituted 5-phenylpentan-1-ols, 5 -phenylpentanals, 5-phenylpentanitriles, 5-phenylpentanoic acid and lower alkyl esters thereof and 5-phenylpentan-1-yl esters of C
1-C
6
aliphatic acids as fragrance materials. The disclosed fragrance materials are, in large measure, novel compounds.
DETAILED DESCRIPTION OF THE INVENTION
The compounds found to possess attractive fragrance properties in accordance with the present invention are represented by the formula
wherein each of R
1
, R
2
and R
3
is independently selected from the group consisting of hydrogen, methyl and ethyl; R
4
is selected from the group consisting of hydrogen, C
1−4
lower alkyl and C
1−4
lower alkoxy; and Z is selected from the group consisting of —CHO, —CN, —CH
2
OH, —COOH, —COOR, and —CH
2
OC(O)R wherein R is lower alkyl, with the proviso that, when Z is—CHO, at least R
3
is other than hydrogen.
Certain compounds within the scope of the present invention are novel, i.e. those represented by the above formula wherein each of R
1
, R
2
and R
3
is independently selected from the group consisting of hydrogen, methyl and ethyl; R
4
is selected from the group consisting of hydrogen, C
1−4
lower alkyl and C
1−4
lower alkoxy; and Z is selected from the group consisting of —CHO, —CH
2
OH, —COOH, —COOR, and —CH
2
OC(O)R wherein R is lower alkyl with the proviso that, when Z is —CHO, at least R
1
and R
3
are other then hydrogen, when Z is —CH
2
OH, R
1
is hydrogen and at least one of R
2
, R
3
and R
4
is other than hydrogen, and when Z is —COOCH
3
, at least R
1
is other than hydrogen.
Preferred fragrance materials in accordance with the present invention are compounds represented by the above formula wherein Z is selected from —CHO, —CN, —CH
2
OH, —COOH and —COOR wherein R is lower alkyl. Preferably, at least one of R
1
, R
2
and R
3
is methyl or ethyl, in the order R
3
, R
1
and R
2
. The R
4
substituent on the phenyl ring can be ortho, meta or para to the bond to the pentane chain, preferably para.
The term “lower alkyl ”as utilized herein shall mean both straight- or branched- chain alkyl radicals having from one to six carbon atoms, unless designated otherwise. This definition applies as well to the alkyl portion of lower alkoxy radicals as a meaning for R
4
.
Preferred fragrance materials in accordance with the present invention include the following:
2-Methyl-5-phenylpentanenitrile
2-Methyl-5-phenylpentyl acetate
4-Methyl-5-phenylpentanenitrile
4-Methyl-5-phenylpentan-1-ol
4-Methyl-5-phenylpentanal
2,4-Dimethyl-5-phenylpentanitrile
2,4-Dimethyl-5-phenylpentan-1-ol
2,4-Dimethyl-5-phenylpentanal
Methyl 4-methyl-5-phenylpentanate
3-Ethyl-5-phenylpentanenitrile.
Compounds of the above formula wherein Z is —CN can be prepared from the corresponding substituted 3-phenylpropanal, known compounds, by reaction with cyanoacetic acid under alkaline conditions in the presence of an organic solvent. For example, 4-methyl-5-phenylpentanitrile can be prepared by the reaction of 2-methyl-3phenylpropanal. The substituted 5-phenylpentanitriles can conveniently be converted to the corresponding 5-phenylpentanals by known techniques, for example, by reaction with diisobutylaluminum hydride in a suitable organic solvent such as, for example, toluene. The substituted 5-phenylpentanals may then be converted to the corresponding substituted 5-phenyl-pentan-1-ols by reduction with hydrogen over a suitable catalyst, such as nickel on silica or palladium on carbon. The subject substituted 5phenylpentanals are also readily converted to the corresponding substituted 5-phenylpentanoic acids by oxidation with oxygen over a suitable catalyst.
The 2-methyl-5-phenyl aldehyde derivatives are conveniently prepared by a number of methods known in the art. For example, by an Aldol condensation between 3-phenylpropanal and proprionaldehyde, followed by hydrogenation of the resulting &agr;,&bgr;-unsaturated aldehyde to form the saturated aldehyde, 2-methyl-5-phenylpentanal. This aldehyde is the direct precursor for the alcohol, 2-methyl-5-phenylpentan-1-ol via reduction with, e.g. sodium borohydride, as well as the nitrile, 2,4-dimethyl-5-phenyl-pentanitrile via oxidation dehydration chemistry by reaction of hydroxylamine/formic acid as described above. Alternatively, aldehyde derivatives may be prepared by oxidation of the corresponding primary alcohol, i.e. 2-methyl-5-phenylpentan-1-ol, a known compound. The corresponding nitrile, 2-methyl-5-phenylpentanenitrile, is prepared by converting the aldehyde via reaction with hydroxylamine to form the aldoxime intermediate and subsequent formic acid catalyzed dehydration. The primary alcohol may also be converted to the corresponding acid as described above.
The 2,4-dimethyl-5-phenylpentan-1-yl derivatives in accordance with the present invention can be prepared by a variety of ways. For example, by an Aldol condensation between 2-methyl-3-phenylpropanal and proprionaldehyde, followed by hydrogenation of the resulting &agr;,&bgr;-unsaturated aldehyde to form the saturated aldehyde, 2,4-dimethyl-5-phenylpentanal as described above. This aldehyde is the direct precursor for the alcohol, 2,4-dimethyl-5 -phenylpentan-1-ol via reduction with, e.g. sodium borohydride, as well as the nitrile, 2,4-dimethyl-5-phenyl-pentanitrile via oxidation dehydration chemistry by reaction of hydroxylamine/formic acid as described above.
The substituted 5-phenylpentanols may readily be converted to the reverse ester form, i.e. where Z in the above formula is —CH
2
OC(O)CH
3
by reaction with acetic anhydride or acetic acid. Such reactions may be conducted with or without the aid of a catalyst, and an inert solvent, such as toluene, may be used with the application of heat to drive the reaction if necessary. in a like manner, the substituted 5-phenylpentanoic acids may be converted to the corresponding ester by reaction with an appropriate alcohol. Such esterification reactions are well known and widely referred to in the chemical literatur
Frank Walter C.
Jubian Vrej
Pagano Alex R.
Bush Boake Allen Inc.
Cole Monique T.
Gibbons Del Deo Dolan Griffinger & Vecchione
Warden Jill
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