International Flavors & Fragrances Inc.

Nicholas Calderone

Braja D Mookherjee

Robert W Trenkle

Keith P Sands

Takao Yoshida

Hugh Watkins

Myrna L Hagedorn

Lisa T Schreck

Ronald S Fenn

Described is the schiff base reaction product of methyl anthranilate having the structure: ##STR1## with ethyl vanillin having the structure: ##STR2## a compound having the structure: ##STR3## and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles including perfumed polymers and colognes. The schiff base having the structure: ##STR4## also has unexpected, unobvious and advantageous utilities for its deodorancy properties in addition to having valuable properties as a fragrance material.

Schiff base reaction product of ethyl vanillin and methyl anthranilate

Described are the schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R' represents ethyl or methyl with ketones and aldehydes defined according to the structure: ##STR2## wherein R' represents methyl or hydrogen and R represents one of the moieties: ##STR3## including compounds defined according to the generic structure: ##STR4## wherein R, R' and R' are defined, supra. Also described are uses of such schiff base reaction products in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, perfurmed articles (including perfumed polymers, detergents and fabric softeners), colognes, foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos. The schiff base reaction products of our invention also have unexpected, unobvious and advantageous utilities for their deodorancy properties in addition to having valuable properties as fragrance materials and as flavor materials.

Uses for augmenting or enhancing the aroma or taste of foodstuffs and

Described are schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R.sub.3 represents methyl or ethyl; helional having the structure: ##STR2## and aldehydes having the generic structure: ##STR3## wherein R represents a hydrocarbyl or hydroxy hydrocarbyl moiety including the aldehydes:

Schiff base reaction products of mixtures of aldehydes including

Described are the schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R' represents ethyl or methyl with ketones and aldehydes defined according to the structure: ##STR2## wherein R' represents methyl or hydrogen and R represents one of the moieties: ##STR3## including compounds defined according to the generic structure: ##STR4## wherein R, R' and R' are defined, supra. Also described are uses of such schiff base reaction products in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, perfumed articles (including perfumed polymers, detergents and fabric softeners), colognes, foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos. The schiff base reaction products of our invention also have unexpected, unobvious and advantageous utilities for their deodorancy properties in addition to having valuable properties as fragrance materials and as flavor materials.

Flavoring with schiff base reaction products of alkyl anthranilates

Schiff base reaction products of alkyl anthranilates and organoleptic

Described are schiff base reaction products of alkyl anthanilates having the structure: ##STR1## wherein R.sub.3 represents methyl or ethyl and aldehydes of the generic structure: ##STR2## wherein R represents unsaturated hydrocarbyl and alkoxy hydrocarbyl moieties or mixtures of aldehydes having the structures: ##STR3## wherein R.sub.1 and R.sub.2 are different alkoxy hydrocarbyl moieties and hydrocarbyl moieties including the aldehydes:

Flavoring with schiff base reaction products of aldehydes and alkyl

Described is a process for augmenting or enhancing the aroma or taste of a foodstuff or chewing comprising the step of intimately admixing with a foodstuff or chewing gum base an aroma or taste augmenting or enhancing quantity of a composition of matter prepared by reacting canthoxal having the structure: ##STR1## with methyl anthranilate to produce a composition of matter containing a compound having the structure:

Use of Schiff base reaction product of methyl anthranilate and canthoxal

Described are schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R.sub.3 represents methyl or ethyl and aldehydes of the generic structure: ##STR2## wherein R represents unsaturated hydrocarbyl and alkoxy hydrocarbyl moieties or mixtures of aldehydes having the structures: ##STR3## wherein R.sub.1 and R.sub.2 are different alkoxy hydrocarbyl moieties and hydrocarbyl moieties including the aldehydes:

Schiff base reaction products of aldehydes and alkyl anthranilates and

Flavoring with schif base reaction products of alkyl anthranilates

Described is the compound, 4-methyl-3-cyclohexene-1-carboxylic acid having the structure: ##STR1## and the use thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles as well as bath preparations and hair preparations). The said 4-methyl-3-cyclohexene-1-carboxylic acid is particularly useful as a replacement for cumin oil and/or cumin aldehyde in perfume compositions, colognes and perfumed articles.

Use of 4-methyl-3-cyclohexene-1-carboxylic acid for augmenting or

Described in the compound, 4-methyl-3-cyclohexene-1-carboxylic acid having the structure: ##STR1## and the use thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles as well as bath preparations and hair preparations). The said 4-methyl-3-cyclohexene-1-carboxylic acid is particularly useful as a replacement for cumin oil and/or cumin aldehyde in perfume compositions, colognes and perfumed articles.

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Laurel Hollow, NY, United States of America

Nicholas Calderone