# US 4,391,284 A · Use in modifying smoking tobacco aroma and flavor or mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives

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- Number: US 4,391,284 A
- Document ID: US4391284A
- Status: Granted
- Kind: A
- Application number: 06/354,387
- Filed: 1982-03-02
- Granted: 1983-07-05
- Earliest claimed: 1982-03-02
- Assignees: International Flavors & Fragrances Inc.
- Inventors: Mark A. Sprecker; Marie R. Hanna; Richard J. Tokarzewski; Robert P. Belko; Hugh Watkins; Manfred H. Vock
- Web page: https://patentgrep.com/patent/US4391284A

## CPC

- A24B 15/345: {containing condensed rings}
- C07C 47/347: having a —CHO group on a condensed ring system
- C07C 47/445: containing a condensed ring system
- A24B: MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Described is the use in modifying, augmenting or enhancing the aroma or taste of smoking tobacco products of 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.

## Claims

### Claim 1

A process for augmenting or enhancing the aroma or taste of a consumable material selected from the group consisting of smoking tobacco compositions and smoking tobacco articles comprising the step of adding to said consumable material an aroma or taste augmenting or enhancing quantity of at least one compound defined according to the structure: ##STR153## wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single 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 "" represents hydrogen; and
(ii) at least four of R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 '", R.sub.5 "" represent hydrogen;
with Z being a moiety selected from the group consisting of: ##STR154## with the line:
[++++]
representing a carbon-carbon single bond or no bond at all; and R.sub.7 and R.sub.8 being separately C.sub.1 -C.sub.4 lower alkyl or, taken together, being C.sub.2 -C.sub.4 alkylene.

### Claim 2 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR155##

### Claim 3 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR156##

### Claim 4 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR157##

### Claim 5 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR158##

### Claim 6 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR159##

### Claim 7 (depends on 1)

The process of claim 1 wherein the substance added to the consumable material which substance is defined according to the structure: ##STR160##
is a mixture having the structures: ##STR161##

### Claim 8 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR162##

### Claim 9 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR163##

### Claim 10 (depends on 1)

The process of claim 1 wherein the compound added to the consumable material has the structure: ##STR164##