International Flavors & Fragrances Inc.

Kenneth K Light

Manfred H Vock

Joaquin F Vinals

Edward J Shuster

William L Schreiber

John B Hall

Mark A Sprecker

Braja D Mookherjee

James M Sanders

Venkatesh Kamath

Ching Y Tseng

Denis E Hruza, Sr

Jacob Kiwala

Takao Yoshida

Joseph A McGhie

Bette M Spencer

Ronald P Schreck

Frederick L Schmitt

Futoshi Fujioka

Ranya Muralidhara

Loren B Schreiber

Robert W Trenkle

Braja Dulal Mookherjee

Edward J Schuster

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 is a process for preparing solanone and norsolanadione wherein in preparing solanone, the compound having the structure: ##STR1## or a mixture of compounds defined according to the structure: ##STR2## is reacted with methyl lithium and the resulting intermediate is hydrolyzed and the resulting compound is dehydrated and wherein in preparing norsolanadione this compound or mixture of compounds is reacted with ethylene glycol or propylene glycol thereby forming a ketal and the resulting ketal is reacted with methyl lithium and the resulting intermediate is then hydrolyzed in the presence of acid in which one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond.

Process for producing solanone, norsolanadione and intermediates therefor

Described is a process for preparing solanone and norsolanadione, both useful as tobacco flavorants.

Described is a process for preparing solanone and norsolanadione using chemical intermediates: which provide an organoleptically improved smoking tobacco product and additives therefor.

The invention provides an organoleptically improved smoking tobacco product and additives therefor as well as methods of making the same.

Described are 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; a process for preparing same using compounds designed according to the generic structure: ##STR2## and organoleptic uses thereof in perfumes, colognes and perfumed articles.

Described are the compounds covered by the generic structure: ##STR1## wherein 'R' represents hydrogen or lithium. The compound having the structure: ##STR2## is useful in augmenting or enhancing the patchouli aroma of a perfume, cologne or perfumed article, such as a solid or liquid anionic, cationic, nonionic or zwitterionic detergent. The compound having the structure: ##STR3## is an intermediate for preparing the compound having the structure: ##STR4## according to the process defined by the reaction: ##STR5## .

Bridged tricyclic alcohol, process for preparing same and perfumery use

Described is a process for preparing solanone and norsolanadione using chemical intermediates defined according to the generic structure: ##STR1## wherein X is one of the moieties: ##STR2## wherein R represents hydrogen or methyl; wherein Y represents one of the structures: ##STR3## 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; with the provisos that:

Described is a process for augmenting or enhancing the aroma or taste of foodstuffs and chewing gums comprising the step of adding to a foodstuff composition or chewing gum composition, an aroma or taste augmenting or enhancing quantity of at least one of the two compounds having the structures: ##STR1##

Use of esters of 1-acetyl cyclohexanol in augmenting or enhancing the

Described is a process for preparing several substituted or unsubstituted cycloalkyl acyl alkanoates defined according to the generic structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together complete a cycloalkyl moiety or methyl, dimethyl or trimethyl substituted cycloalkyl moiety containing five or six carbon atoms in the ring and wherein R.sub.3 is C.sub.1 -C.sub.3 lower alkyl and R.sub.4 is methyl or hydrogen by reacting a compound having the generic structure: ##STR2## in an aqueous silver-ion containing solution having a weakly acidic pH at elevated temperatures. The compounds so produced are useful for their organoleptic properties in consumable materials, such as foodstuffs, foodstuff flavorants, chewing gums, chewing gum flavorants, toothpastes, toothpaste flavorants, medicinal products, medicinal product flavorants, chewing tobaccos, chewing tobacco flavorants, smoking tobaccos, smoking tobacco flavorants, perfume compositions, perfumed articles, such as cationic, anionic, nonionic and zwitterionic detergents, fabric softener compositions, drier-added fabric softener articles, textile sizing agents and optical brighteners for textiles as well as colognes.

Alkyl esters of 1-alkanoyl cycloalkanols and organoleptic uses thereof

Described are the compounds covered by the generic structure: ##STR1## wherein 'R' represents hydrogen or lithium. The compound having the structure: ##STR2## is useful in augmenting or enhancing the patchouli aroma of a perfume, cologne or perfumed article, such as a solid or liquid anionic, cationic, nonionic or zwitterionic detergent. The compound having the structure: ##STR3## is an intermediate for preparing the compund having the structure: ##STR4## according to the process defined by the reaction: ##STR5##

Described are 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; a process for preparing same using compounds designed according to the generic structure: ##STR2## and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic, nonionic or zwitterionic solid or liquid detergents, cosmetic powders, fabric softener compositions and dryer-added fabric softener articles, as well as in foodstuffs, chewing tobaccos, smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor. Thus, the tricyclic alcohol, ether or ester compounds of our invention having the generic structure: ##STR3## impart, augment or enhance dry woody (cedary, vetiver), thymol-like, camphoraceous, amber, sandalwood-like, fresh, sweaty, fruity, castoreum, cedrus atlantica, patchouli-like, labdanum, green, fruity, woody, cigar box-like, oriental, cedarwood-like, minty, spicy, floral (rose), vetiver-like, grapefruit oil-like, fruity and sweet aromas in or to perfume compositions, colognes and perfumed articles as well as oriental/incense, herbaceous, minty, earthy, woody, tobacco-like and cedarwood-like aromas and tastes to foodstuffs, chewing tobaccos, smoking tobaccos and smoking tobacco articles; wherein in the smoking tobaccos and smoking tobacco articles, these aromas and tastes are both prior to and on smoking in both the main stream and the side stream.

Described is a process for preparing several substituted or unsubstituted cycloalkyl acyl alkanolates defined according to the generic structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together complete a cycloalkyl moiety or methyl, dimethyl or trimethyl substituted cycloalkyl moiety containing five or six carbon atoms in the ring and wherein R.sub.3 is C.sub.1 -C.sub.3 lower alkyl and R.sub.4 is methyl or hydrogen by reacting a compound having the generic structure: ##STR2## in an aqueous silver-ion containing solution having a weakly acidic pH at elevated temperatures. The compounds so produced are useful for their organoleptic properties in consumable materials, such as foodstuffs, foodstuff flavorants, chewing gums, chewing gum flavorants, toothpastes, toothpaste flavorants, medicinal products, medicinal product flavorants, chewing tobaccos, chewing tobacco flavorants, smoking tobaccos, smoking tobacco flavorants, perfume compositions, perfumed articles, such as cationic, anionic, nonionic and zwitterionic detergents, fabric softener compositions, drier-added fabric softener articles, textile sizing agents and optical brighteners for textiles as well as colognes.

Process for enhancing the organoleptic properties of perfumed articles

Described in the use for augmenting or enhancing the aroma or taste of foodstuffs of 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 are the same or different and each represents hydrogen, methyl or ethyl.

Growing community of inventors

Long Branch, NJ, United States of America

Kenneth K Light