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Perfume uses of reactive product containing mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives
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Inventors: Sprecker, Mark A.; Hanna, Marie R.; Tokarzewski, Richard J.; Belko, Robert P.; Watkins, Hugh; Vock, Manfred H.;
Assignee: International Flavors & Fragrances Inc. (New York, NY)
Primary Examiner:
Assistant Examiner:
Attorney, Agent or Firm:
Described are mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 '", R.sub.1 "", R.sub.3, R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 '", R.sub.5 "" and R.sub.6 represent hydrogen or methyl with the provisos: (i) at least four of R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 '" and R.sub.1 "" are hydrogen; and (ii) at least four of R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 '" and R.sub.5 "" represent hydrogen; and wherein Z represents one of the moieties; (i) carboxaldehyde having the structure: ##STR2## (ii) alkylene dioxy or dialkoxy methyl having the structure: ##STR3## (iii) hydroxy methyl having the structure: ##STR4## (iv) acetoxymethyl having the structure: ##STR5## and wherein R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl or R.sub.7 and R.sub.8 taken together represent C.sub.2 -C.sub.4 alkylene; wherein the line represented by: [++++] is either (i) a carbon-carbon single bond when R.sub.7 and R.sub.8 taken together are C.sub.2 -C.sub.4 alkylene or (ii) no bond at all when R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl. Also described are processes for preparing such mono-oxomethyl substituted polyhydrodimethanonaphthalene derivative, and processes for using the above defined mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives, for their organoleptic properties and compositions containing said mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives including perfumes, perfumed articles (such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softeners and cosmetic powders), foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles. |
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DETAILED DESCRIPTION OF THE DRAWINGS FIG.
1 is the GLC profile for the reaction product of Example I containing the compound having the structure: ##STR43## The peak indicated by the reference numeral 1 is the peak for the compound having the structure: ##STR44## FIG.
7 is the GLC profile for reaction product of Example III.
The peak indicated by the reference numeral 11 is for the compound defined according to the structure: ##STR45## The peak indicated by the reference numeral 12 is for the compound defined according to the structure: ##STR46## The peak indicated by the reference numeral 13 is for the reaction product defined according to the structure: ##STR47## FIG.
9 is the GLC profile for the reaction product of Example IV, bulked distillation fractions 3-11.
The peak indicated by the reference numeral 21 is for the reaction product having the structure: ##STR48## FIG.
12 is the GLC profile for the reaction product of Example V.
The peak indicated by the reference numeral 31 is for the reaction product having the structure: ##STR49## FIG.
15 is the GLC profile for the reaction product of Example VI.
The peak indicated by the reference numeral 41 is for the reaction product having the structure: ##STR50## FIG.
21 is the GLC profile for the reaction product of Example VIII.
The peak indicated by the reference numeral 51 is for the reaction product which is a mixture of compounds defined according to the structures: ##STR51## THE INVENTION It has now been determined that certain mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives are capable of imparting a variety of flavors and fragrances to various consumable materials.
Briefly, our invention contemplates augmenting or enhancing the flavors and/or fragrances of such consumable materials by adding thereto a small but effective amount of at least one such mono-oxomethyl substituted polyhydrodimethanonaphthalene derivative defined according to the generic structure: ##STR52## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein R
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