International Flavors & Fragrances Inc.

Myrna L Hagedorn

Mark A Sprecker

Mohamad I Farbood

Braja D Mookherjee

Joaquin F Vinals

William L Schreiber

Edward J Shuster

James M Sanders

Philip T Klemarczyk

Hugh Watkins

Thomas J O'Rourke

Alan O Pittet

Robert W Trenkle

Ranya Muralidhara

Manfred H Vock

Kevin P Miller

Nicholas Calderone

James A Morris

Keith P Sands

Lynda J Bienkowski

Richard M Boden

Lynda B McLean

Nicolas Kossiakoff

Robert W Blocker

Augustine Yonghwi Kim

Michael P McLean

Marie R Hanna

Futoshi Fujioka

Anubhav P Narula

Charles E Beck

Kathleen E Boardwick

William D Gillaspey

Anthony G Branco

Richard A Wilson

Michael G Monteleone

Joseph A McGhie

Michael J Zampino

Anton Van Ouwerkerk

Described is a bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, as well as a novel jasmonic acid isomer produced thereby and organoleptic uses thereof. The process yields at least 5% of the 'cis' isomer defined according the structure: (wherein R is hydrogen or methyl) or at least 5% of the 'cis' isomer defined according to the structure: (wherein R is hydrogen or methyl). Compositions containing at least 98% of the isomer having the structure: with an optical rotation (&#x3b1;) of +58&#xb0; are novel. Compositions containing at least 98% of the isomer having the structure: with an optical rotation (&#x3b1;) of +58&#xb0; are also novel. The process of our invention comprises the cultivation under aerobic condition of one or more specific strain ofin a nutrient medium followed either by (1) isolation of the jasmonic acid product or (2) esterification of the jasmonic acid to form methyl jasmonate followed by the isolation of the methyl jasmonate and novel products produced by such process.

Jasmonic acid and jasmonic acid ester stereoisomers and compositions

Bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, novel jasmonic acid isomer produced thereby and uses thereof

Described is a bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate, as well as a novel jasmonic acid isomer produced thereby and organoleptic uses thereof. The process yields at least 5% of the &ldquo;cis&rdquo; isomer defined according the structure:

Bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate

Described are oxypentamethylindane carboxaldehydes defined according to the generic structure: ##STR1## wherein R' represents a hydrogen or methyl, methods for preparing same, organoleptic uses thereof and cosmetic and pharmaceutical compositions containing them. The oxypentamethylindane carboxaldehydes particularly are useful in perfumery and as U.V. absorbers in sun screen compositions.

Oxypentamethylindane carboxaldehydes, methods for preparing same,

Described is a process for the preparation of compositions of matter containing unsaturated lactones defined according to the generic structure: ##STR1## wherein R represents C.sub.6 alkyl or alkenyl; and X represents C.sub.2, C.sub.4 or C.sub.6 alkylene or alkenylene; with the provisos that R is C.sub.6 alkyl when X is alkenylene and R is C.sub.6 alkenyl when X is alkylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of:

Process for preparing compositions containing unsaturated lactones,

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 3,7-dimethyl-6,7-dioxo-1,3-octadienes or mixtures of same defined according to the structure: ##STR1## wherein R is hydrogen or ethyl and X is one of the moieties: ##STR2## and wherein the wavy lines represent a 'E' or 'Z' configuration of the methyl and vinyl moiety about the 3,4-pi-bond of the molecule, as well as methods for 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 at least one of said 3,7-dimethyl-6,7-dioxo-1,3-octadienes.

3,7-dimethyl-6,7-dioxo-1,3-octadiene derivatives and organoleptic uses

Flavoring with mixtures of lactones

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

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

Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers. Also defined and claimed is the pure crystalline form of the compound defined according to the structure:

Process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone,

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Edison, NJ, United States of America

Myrna L Hagedorn