International Flavors & Fragrances Inc.

Robin K Wolff

Braja D Mookherjee

Robert W Trenkle

Richard M Boden

Takao Yoshida

Ira D Hill

Seymour J Spitz, Jr

Lloyd F Keleher

Described is a process for preparing at least one secondary alcohol of the class of methyl substituted pinyl hydroxy pentenes comprising the step of:

Methyl substituted pinyl oxopentenes, organoleptic uses thereof and

Described are methyl substituted pinyl oxopentenes and mixtures of same defined according to the structure: ##STR1## wherein Z represents methylidene pinyl oxopentenes and mixtures of same defined according to the structure: ##STR2## ethylidene defined according to the structure: ##STR3## or ethylenyl defined according to the structure: ##STR4## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents no bond; wherein n is 0 or 1 and m is 0 or 1 with the sum of n+m being equal to 1; wherein X represents carbinol having the structure: ##STR5## or ketone having the structure: ##STR6## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or methyl.

Methyl substituted pinyl oxopentenes and organoleptic uses thereof

Described are methyl substituted pinyl oxopentenes and mixtures of same and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, perfumed articles (including perfumed polymers, solid or liquid cationic, anionic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, optical brightener compositions, and cosmetic powders), colognes, smoking tobacco compositions and smoking tobacco articles including cigars, cigarettes and integrated and separate filters therefor. Also described are processes for preparing such compounds including the steps of reacting alpha and/or beta pinene with carbon monoxide and hydrogen via an oxo reaction in the presence of a catalyst to produce a mixture of aldehydes and then reacting the resulting mixture of aldehydes with methyl ethyl ketone in the presence of a basic catalyst to produce the compounds of our invention.

Described are methyl substituted pinyl oxopentenes and mixtures of same defined according to the structure: ##STR1## having utility in augmenting or enhancing the aroma or taste of consumable material.

Organoleptic use of methyl substituted pinyl oxopentenes

Described is a mixture of vinyl alkanols produced by carrying out an oxo reaction on pinene and then carrying out an oldol condensation with the reaction product. The resulting products are useful as favoring and perfumery.

Described are hydroxy alkenyl bicyclic terpene derivatives useful in perfumery.

Described is a process for imparting an 'air dried cloth' aroma to cloth, synthetic or natural, previously dried using a clothes drier, comprising the step of contacting the cloth prior to drying with an aroma augmenting or enhancing quantity of either (i) a mixture consisting essentially of:

Process for augmenting or enhancing the fresh air aroma of consumable

Described is a method for augmenting or enhancing the aroma or taste of a mango, guava or papaya flavored foodstuff or chewing gum comprising the step of intimately admixing with said foodstuff or chewing gum from 0.02 parts per million up to about 300 parts per million based on total composition of a mixture of compounds prepared according to the process consisting essentially of the steps of:

Process for augmenting or enhancing the tropical fruit aroma or taste of

Described is a method of chemically increasing the amount of extractable cedarwood oil from Juniperus Mexicana (commonly known as 'Texas cedarwood') by treating standing living Juniperus Mexicana with a solution comprising a bipyridylium salt and permitting said trees to continue to grow in their natural environment for a period of time of at least two months. Portions of the trees are then cut and the cedarwood oil is extracted therefrom using unit operations including, but not limited to, steam distillation, in relatively large yields.

Method of increasing extractable cedarwood oil from Juniperus Mexicana

Process for augmenting or enhancing the fresh air aroma of clothing

Described is the use for augmenting or enhancing the aroma or taste of smoking tobaccos and smoking tobacco articles of methyl substituted pinyl oxopentenes and mixtures of same defined according to the structure: ##STR1## wherein Z represents methylidene defined according to the structure: ##STR2## ethylidene defined according to the structure: ##STR3## or ethylenyl defined according to the structure: ##STR4## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents no bond; wherein n is 0 or 1, and m is 0 or 1 with the sum of n+ m being equal to 1; wherein X represents carbinol having the structure: ##STR5## or ketone having the structure: ##STR6## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or methyl; wherein one of the lines:

Use of methyl substituted pinyl oxopentenes, for augmenting, enhancing

Described is a method for augmenting or enhancing the aroma or taste of a raspberry flavored foodstuff or chewing gum comprising the step of intimately admixing with said foodstuff or chewing gum from 0.02 parts per million up to about 300 parts per million based on total composition of a mixture of compounds prepared according to the process consisting essentially of the steps of:

Process for augmenting or enhancing the raspberry aroma or taste of a

Described are methyl substituted pinyl oxopentenes and mixtures of same and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, perfumed articles (including perfumed polymers, solid or liquid cationic, anionic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, optical brightener compositions, and cosmetic powders), colognes, smoking tobacco compositions and smoking tobacco articles including cigars, cigarettes and integrated and separated filters therefor. Also described are processes for preparing such compounds including the steps of reacting alpha and/or beta pinene with carbon monoxide and hydrogen via an oxo reaction in the presence of a catalyst to produce a mixture of aldehydes and then reacting the resulting mixture of aldehydes with methyl ethyl ketone in the presence of a basic catalyst to produce the compounds of our invention.

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Point Pleasant, NJ, United States of America

Robin K Wolff