International Flavors & Fragrances Inc.

Denis E Hruza

John B Hall

Manfred H Vock

Joaquin F Vinals

Edward J Shuster

Jacob Kiwala

Takao Yoshida

A process is described for the preparation of allyl acetone (5-hexen-2-one) according to the reaction: ##STR1## wherein R is methyl or ethyl; X is chloro or bromo; M is sodium or potassium; and Q is sodium or potassium, the reaction being carried out (i) using a phase transfer agent and (ii) in a two phase system.

Process for the production of allyl acetone

Described are spiropyran derivatives useful in preparing smoking tobacco compositions and flavoring compositions for tobacco having the structure: ##STR1## wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; wherein when one of R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 or R.sub.7 is any of C.sub.2 -C.sub.5 lower alkyl, each of the other of the R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 moieties is hydrogen; wherein each of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond, with at least one of the dashed lines being a carbon-carbon single bond. In tobacco flavoring such compounds give rise to aromatic, sweet, minty and cooling notes.

Use for preparing smoking tobacco compositions of spiropyran derivatives

Described are spiropyran materials useful in augmenting enhancing or modifying the aroma of perfume compositions and colognes which spiropyran materials have the structure: ##STR1## wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and.sub.7 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; wherein when one of R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 or R.sub.7 is any of C.sub.2 -C.sub.5 lower alkyl, each of the other of the R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 moieties is hydrogen; wherein each of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond, with at least one of the dashed lines being a carbon-carbon single bond. Green, floral, herbal, eucalyptol-like, sweet, minty and terpineol-like notes are produced in such perfume compositions and colognes.

Use of certain spiropyran derivatives for augmenting, enhancing or

Described are spiropyran derivatives for use in augmenting, enhancing or modifying the aroma of perfumed articles including detergents, said spiropyran derivatives having the structure: ##STR1## wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; wherein when one of R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 or R.sub.7 is any of C.sub.2 -C.sub.5 lower alkyl, each of the other of the R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 moieties is hydrogen; wherein each of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond, with at least one of the dashed lines being a carbon-carbon single bond. These detergents have green, floral, herbal, eucalyptol-like, sweet, minth and/or terpineol-like notes.

Use of spiropyran derivatives in augmenting, enhancing or modifying the

Described is the novel compound group, 2-alkyl-4-phenyl-dihydropyrans having the generic structure: ##STR1## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond, R.sup.1 is one of C.sub.1 -C.sub.3 alkyl, and R is one of C.sub.2 -C.sub.4 alkyl, a process for producing same; a process comprising adding to tobacco an amount sufficient to augment the flavor or aroma of such tobacco of one or more of said pyran compounds; flavor formulations for use in conjunction with tobacco products containing one or more of such pyrans; a process comprising adding to foodstuffs, foodstuff flavorings, chewing gums, chewing gum flavorings, toothpaste and toothpaste flavorings one or more of said pyran compounds in a quantity sufficient to augment or enhance neroli-like and grape-like flavors, and flavoring compositions containing said pyran compounds.

2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the

Described are methods for preparing foodstuffs, flavoring compositions for foodstuffs, tobacco compositions, flavoring compositions for tobacco, perfume compositions, ingredients for perfume compositions, perfumed articles and ingredients for perfumed articles by including therein one or more C.sub.1 -C.sub.6 alkyl-2-methyl-3,4-pentadienoates in order to produce:

Ethyl-2-methyl-3,4-pentadienoate perfume compositions

Described is the novel compound group, 2-alkyl-4-phenyl-dihydropyrans in combination with smoking tobacco having the generic structure: ##STR1## where one of the dashed lines is a carbon-carbon double bond, R.sup.1 is one of C.sub.1 -C.sub.3 alkyl, and R is one of C.sub.2 -C.sub.4 alkyl, a process for producing same; a process comprising adding to tobacco an amount sufficient to augment the flavor or aroma of such tobacco of one or more of said pyran compounds; flavor formulations for use in conjunction with tobacco products containing one or more of such pyrans; a process comprising adding to foodstuffs, foodstuff flavorings, chewing gums, chewing gum flavorings, toothpaste and toothpaste flavorings one or more of said pyran compounds in a quantity sufficient to augment or enhance neroli-like and grape-like flavors, and flavoring compositions containing said pyran compounds.

Described is the novel compound group, 2-alkyl-4-phenyl-dihydropyrans having the generic structure: ##STR1## where one of the dashed lines is a carbon-carbon double bond, R.sup.1 is one of C.sub.1 -C.sub.3 alkyl, and R is one of C.sub.2 -C.sub.4 alkyl, a process for producing same; a process comprising adding to tobacco an amount sufficient to augment the flavor or aroma of such tobacco of one or more of said pyran compounds; flavor formulations for use in conjunction with tobacco products containing one or more of such pyrans; a process comprising adding to foodstuffs, foodstuff flavorings, chewing gums, chewing gum flavorings, toothpaste and toothpaste flavorings one or more of said pyran compounds in a quantity sufficient to augment or enhance neroli-like and grape-like flavors, and flavoring compositions containing said pyran compounds.

A tobacco article comprising tobacco Tobacco and C.sub.1 -C.sub.6 alkyl-2-methyl-3,4-pentadienoates as a flavor adjuvant.

Flavored tobacco article

Alkyl-2-methyl-3,4-pentadienoates

Methods for preparing foodstuffs, flavoring compositions for foodstuffs, chewing gum and flavoring compositions for chewing gums by including therein 4-methyl-1-oxaspiro[5.5]undecane.

Flavoring with 4-methyl-1-oxaspiro[5.5]undecane

A process for producing one or more alkyl-2-methyl pentenoates having the generic structure: ##STR1## comprising the steps of: I. Contacting with hydrogen gas one or more alkyl-2-methyl-3,4-pentadienoates having the structure: ##STR2## in the presence of a hydrogenation catalyst which may be either of: A. Raney Nickel;

Growing community of inventors

Brick Town, NJ, United States of America

Denis E Hruza