International Flavors & Fragrances Inc.

Futoshi Fujioka

Richard M Boden

William L Schreiber

Marie R Hanna

Takao Yoshida

Kenneth K Light

Joseph A McGhie

Lambert Dekker

Patrick Whelan

Patrick Chant

Manfred H Vock

Mark A Sprecker

William J Fylak

William D Gillaspey

Anubhav P Narula

Charles E Beck

Myrna L Hagedorn

Kathleen E Boardwick

Anthony G Branco

Described are 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures defined according to the structure: ##STR1## wherein structure represents mixtures wherein in the mixture in each of the compounds, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond, processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers). Also described is a process for preparing such 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures using as a starting material 2,7-octadienol having the structure: ##STR2## as well as the process intermediates having the structures: ##STR3## wherein R represents C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.2 are the same or different and each represents 2,7-octadienyl or R.

3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures,

Described in the use of dihydromethyl jasmonic acid having the structure: ##STR1## in augmenting, enhancing or imparting fragrances in or to perfume compositions, perfumed articles and colognes.

Fragrance use of dihydromethyl jasmonic acid

Described are adamantane derivatives defined according to the generic structure: ##STR1## wherein R.sub.1 ' is hydrogen or acetyl; R.sub.2 ' is hydrogen or lower alkyl and the dashed line is a carbon-carbon single bond or a carbon-carbon double bond as well as uses thereof for augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, perfumed articles, colognes, smoking tobacco compositions, smoking tobacco articles, deodorizing articles, doedorizing compositions and malodor maskants.

Adamantane derivatives, compositions of matter containing same,

Described are hydroxy adamantane compounds and derivatives thereof and a process for preparing same.

Described for use in augmenting or enhancing the aroma or taste of smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor in a cigarette or cigar, or the whole cigarette or cigar itself are compounds defined according to the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent the same or different hydrogen, methyl or ethyl.

Process for augmenting or enhancing the aroma or taste of smoking

Described are organoleptic compounds having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent the same or different hydrogen, methyl or ethyl.

Tricyclic alcohols, ethers and esters, process for preparing same and

Described are the uses of mixtures of hydroxybornyloxybutanes defined according to the generic structure: ##STR1## wherein in the mixture in each of the compounds one or R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen in augmenting or enhancing the aroma or taste of smoking tobacco articles and smoking tobacco compositions.

Use of hydroxybornyloxybutanes in augmenting or enhancing the aroma or

Described are mixtures of hydroxybornyloxybutanes defined according to the generic structure: ##STR1## wherein in the mixture in each of the compounds one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of said mixture of hydroxybornyloxybutanes. The mixture of hydroxybornyloxybutanes of our invention defined according to the structure: ##STR2## is prepared according to the process of reacting camphene having the structure: ##STR3## with 1,3-dihydroxybutane having the structure: ##STR4## in the presence of an acid catalyst such as a Lewis acid or a protonic acid.

Process for augmenting or enhancing the aroma of detergents using

Hydroxybornyloxybutanes and organoleptic uses thereof

Described is a mixture of polyhydroindan carboxaldehydes defined according to the structure: ##STR1## wherein R.sub.7 represents a moiety selected from the group consisting of methyl and isopropyl prepared by means of reacting bicyclopentadiene with a lower alkanol in the presence of a Lewis acid in order to form a mixture of compounds defined according to the structure: ##STR2## and then reacting the resulting ether with carbon monoxide and hydrogen in the presence of an 'oxo' reaction catalyst.

Alkoxy-substituted polyhydroindan carboxaldehydes

Described are alkyl-substituted spiroundecenone derivatives defined according to the structure: ##STR1## wherein R.sub.1 represents isopropyl or hydrogen; R.sub.2, R.sub.3 and R.sub.4 are the same and each represents methyl or hydrogen; with the provisos that:

Alkyl-substituted spiroundecenone derivatives, organoleptic utility

Described is the genus of polyhydroindan carboxaldehydes defined according to the structure: ##STR1## wherein each of the dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds with the proviso that at least one of the dashed lines represents a carbon-carbon single bond; wherein one of R.sub.1, R.sub.2 and R.sub.3 is hydrogen or methyl and each of the other of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; wherein one of R.sub.4, R.sub.5 and R.sub.6 represents hydrogen or methyl and each of the other of R.sub.4, R.sub.5 and R.sub.6 represents hydrogen; wherein m is 0 or 1 and n is 0 or 1 and the sum of m+n=1; wherein X' represents one of the moieties: ##STR2## wherein R.sub.7 represents C.sub.1 -C.sub.3 alkyl or acetyl; and wherein R.sub.8 represents C.sub.1 -C.sub.3 alkyl, with the proviso that when X' is methylene having the structure: ##STR3## then m is 0 and n is 1 and with the further proviso that when n is 0, one of the dashed lines is a carbon-carbon double bond; and one of R.sub.1, R.sub.2 and R.sub.3 represents methyl and one of R.sub.4, R.sub.5, and R.sub.6 represents methyl, and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, perfumed polymers and cosmetic powders). Also described is a process for preparing such polyhydroindan carboxaldehydes by reacting a tricyclic compound or mixture of compounds defined according to the structure: ##STR4## with carbon monoxide and hydrogen via an 'oxo' reaction; wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are defined, supra; wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein X' represents one of the moieties:  with the proviso that when X' is methylene having the structure: ##STR5## then the line:

Polyhydroindan carboxaldehydes and uses thereof in augmenting or

Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene; C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture or carbon monoxide and hydrogen by means of an oxo reaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols. Also described are two ether carboxaldehydes having one of the structures: ##STR3## processes for preparing such ether carboxaldehydes by means of reacting out an appropriate allyl ether with a mixture of carbon monoxide and hydrogen by means of an oxo-reaction as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colgnes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carboxaldehydes.

Growing community of inventors

Wanamassa, NJ, United States of America

Futoshi Fujioka