International Flavors & Fragrances Inc.

Edward J Granda

Manfred H Vock

Frederick L Schmitt

Joaquin F Vinals

James M Sanders

Braja D Mookherjee

Philip T Klemarczyk

Cynthia J Mussinan

Jacob Kiwala

Edward J Shuster

Bette M Light

Robert W Trenkle

John B Hall

Richard A Wilson

Domenick Luccarelli, Jr

Robin L Kasper

Ronald Schreck

William L Schreiber

Joacquin Vinals

Described is a process for preparing .beta.-damascone starting with 2,6,6-trimethyl cyclohex-2-enone according to the reaction sequence: ##STR1## wherein Z is hydrogen, MgX', Li, Na or K; Y is MgX', Li, Na or K; X' is Cl, Br or I; R is C.sub.1 -C.sub.3 lower alkyl such as methyl, ethyl, n-propyl or i-propyl; X is Cl, Br or I. Also described are the organoleptic uses of the compound having the structure: ##STR2## in augmenting or enhancing the taste or aroma of a consumable material, e.g., foodstuff, chewing gum, medicinal product, chewing tobacco, smoking tobacco, perfume, perfumed article (e.g., drier-added fabric softener articles and solid or liquid anionic, cationic or nonionic detergents) and cologne.

Process for preparing acyl trimethyl cyclohexene derivatives and use of

Described are compounds defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; and one of R.sub.1 and R.sub.2 is methyl and the other of R.sub.1 and R.sub.2 is hydrogen. In addition, organoleptic uses of such compounds are disclosed for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, chewing tobaccos, medicinal products, toothpastes, perfumes, perfumed articles (such as liquid or solid, anionic, cationic, nonionic or zwitterionic detergents), fabric softeners and dryer-added fabric softener articles.

Carbomethoxy methyl norbornanes, organoleptic uses thereof and process

Described are methyl substituted norbornane derivatives having the generic structure: ##STR1## wherein R represents the nitrile moiety having the structure: ##STR2## or the dimethoxymethyl moiety having the structure: ##STR3## and wherein one of R.sub.1, or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen. Also described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, perfumes, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents or fabric softeners or fabric softener articles using as the essential ingredient at least one of methyl substituted norbornane derivatives of our invention.

Methyl substituted norbornane derivatives, organoleptic uses thereof and

Described are methyl substituted norbornane derivatives having the generic structure: ##STR1## wherein R represents the nitrile moiety having the structure:

Process of augmenting the aroma of detergents using methyl substituted

Flavoring with carbomethoxy methyl norbornanes

Use in perfumery are compounds both separately and in admixture having the generic structure: ##STR1## wherein the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond and each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7 represents hydrogen or methyl with the proviso that one of R.sub.1, R.sub.2, R.sub.6 and R.sub.7 is methyl and each of the other of R.sub.1, Rhd 2, R.sub.6 and R.sub.7 is hydrogen and R.sub.3 and R.sub.4 are not both methyl; wherein R.sub.5 represents C.sub.1 -C.sub.4 alkyl are disclosed.

Use in perfumery of carboalkoxy alkyl norbornanes

Described are compounds having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein R.sub.2 is methyl or hydrogen; R.sub.6 is methyl or hydrogen; R.sub.1, R.sub.3 or R.sub.7 represent methyl or hydrogen, with the proviso that one of R.sub.1, R.sub.3 and R.sub.7 represents methyl and the other two of R.sub.1, R.sub.3 and R.sub.7 represent hydrogen; wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or C.sub.1 -C.sub.3 lower alkyl. In addition, organoleptic uses of such compounds are disclosed for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, perfumed articles (such as liquid or solid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, dryer-added fabric softener articles, fabric brighteners and other perfumed articles and colognes). Also disclosed is a process for preparing such compounds according to the reaction scheme: ##STR2## wherein R' represents C.sub.1 C.sub.3 alkyl; m+n=3 with the further proviso that m is 1 or 2 and n is 1 or 2; and wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are as defined above.

Carboamidoalkyl norbornanes, organoleptic uses thereof and process for

Described is a process for augmenting or enhancing the aroma or taste of a foodstuff or chewing gum comprising the step of adding to a foodstuff or chewing gum an aroma augmenting or enhancing quantity of a product comprising a major proportion of compounds defined according to the structure: ##STR1##

Carboalkoxy alkyl norbornanes, organoleptic uses thereof and process for

Described are compounds both separately and in admixture having the generic structure: ##STR1## wherein the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond and each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7 represents hydrogen or methyl with the proviso that one of R.sub.1, R.sub.2, R.sub.6 and R.sub.7 is methyl and each of the other of R.sub.1, R.sub.2, R.sub.6 and R.sub.7 is hydrogen and R.sub.3 and R.sub.4 are not both methyl; wherein R.sub.5 represents C.sub.1 -C.sub.4 alkyl are disclosed. In addition organoleptic uses of such compounds are disclosed for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, chewing tobaccos, medicinal products, toothpastes, perfumes, perfumed articles (such as liquid or solid anionic, cationic, nonionic or zwitterionic detergents) fabric softeners, dryer-added fabric softener articles and smoking tobaccos. Also disclosed is a process for preparing such compounds according to one of the reaction schemes: ##STR2## wherein R' represents C.sub.1 -C.sub.3 alkyl; m+n equals 3 with the proviso that m is one or two and n is one or two; and wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are defined as above; or ##STR3## wherein R.sub.1 -R.sub.7 are defined as above.

Process of enhancing or augmenting the aroma of detergents using

Carbomethoxy methyl norbornanes

Described is a process for augmenting or enhancing the aroma or taste of a smoking tobacco composition or at least a portion of a smoking tobacco article comprising the step of intimately admixing with a smoking tobacco composition or at least a portion of a smoking tobacco article, an aroma or taste augmenting or enhancing quantity of at least one compound defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; R.sub.1 ', R.sub.2 ', R.sub.3 ', R.sub.4 ', R.sub.6 ' and R.sub.7 ' are each selected from the group consisting of hydrogen and methyl and R.sub.5 ' is C.sub.1 -C.sub.4 alkyl with the provisos that;

Use of carboalkoxy alkyl norbornanes for augmenting or enhancing the

Methyl substituted norbornane carboxaldehyde dimethyl acetals

Described are cis-3-hexenyl derivatives having the generic structure: ##STR1## wherein R is one of the moieties: ##STR2## which are useful in foodstuffs, flavorings, fragrances, perfumed articles (e.g. anionic, cationic or nonionic detergents, dryer-added fabric softener articles and cosmetic powders) and smoking tobacco flavorings; processes for producing such cis-3-hexenyl derivatives and products produced according to such processes which include chemical compounds in addition to said cis-3-hexenyl derivatives.

Compositions of matter containing cis-3-hexenal

Described are methyl-substituted norbornane carboxaldehyde having the generic structure: ##STR1## wherein the dashed line is a carbon-carbon single bond, or a carbon-carbon double bond, and R.sub.1 R.sub.2 and R.sub.3 each represent methyl or hydrogen with the proviso that (i) R.sub.1 is hydrogen when R.sub.3 is methyl and (ii) R.sub.1 is methyl when R.sub.3 is hydrogen. Also described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, perfumes, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents or fabric softeners or fabric softener articles using as the essential ingredient at least one of the methyl substituted norbornane carboxaldehydes of our invention.

Growing community of inventors

Englishtown, NJ, United States of America

Edward J Granda