Abstract: Physiological cooling compounds of the structure: where R1 is p-menthyl or 2,3,4-trimethylpent-3-yl group and R2-R8 are hydrogen or alkyl groups. The combination of R2-R8 is such that the N-alkyl group is a branched C5 alkyl or branched or linear C6-C8 alkyl group. The new carboxamides are valuable sensory ingredients which provide long-lasting cooling sensation and freshness in personal care, oral care, cosmetic products, pharmaceutical preparations, confectionary, food and beverages.

Abstract: Spearmint flavor enhancers and methods for the production thereof. The spearmint flavor enhancers may include l-carvone, l-carveol isomers, and d-dihydrocarveol isomers. The spearmint flavor enhancers may further include l-isocarveol isomers, l-carvyl acetate isomers, d-dihydrocarvyl acetate isomers, and l-isocarvyl acetate isomers.

Abstract: Spearmint flavor enhancers and methods for the production thereof. The spearmint flavor enhancers may include l-carvone, l-carveol isomers, and d-dihydrocarveol isomers. The spearmint flavor enhancers may further include l-isocarveol isomers, l-carvyl acetate isomers, d-dihydrocarvyl acetate isomers, and l-isocarvyl acetate isomers.

Abstract: Physiological cooling compounds of the structure: where R1 is p-menthyl or 2,3,4-trimethylpent-3-yl group and R2-R8 are hydrogen or alkyl groups. The combination of R2-R8 is such that the N-alkyl group is a branched C5 alkyl or branched or linear C6-C8 alkyl group. The new carboxamides are valuable sensory ingredients which provide long-lasting cooling sensation and freshness in personal care, oral care, cosmetic products, pharmaceutical preparations, confectionary, food and beverages.

Abstract: A process for interconversion between WS-1 and neo-WS-1 by heating to a temperature in a range of from 60 degrees Celsius to 250 degrees Celsius. The heating can be done in the presence of an acid catalyst. Starting from practically pure (=98%) WS-1, or mixtures of WS-1 and neo-WS-1, practically pure (=98%) neo-WS-1 can be obtained. Starting from practically pure (=98%) neo-WS-1, or mixtures of WS-1 and neo-WS-1, practically pure (=98%) WS-1 can be obtained.

Abstract: A process for making trans-isocarveol, an intermediate useful in the manufacture of perillyl alcohol, is disclosed. The process comprises isomerizing a mixture comprising cis-limonene oxide (cis-LMO) and trans-limonene oxide (trans-LMO) in the presence of a phenolic modifier and a chromium catalyst. The process is performed at a temperature less than 220° C. to convert more than 50% of the cis-LMO to trans-isocarveol and less than 50% of the trans-LMO to cis-isocarveol. We surprisingly found that a mixture of cis- and trans-LMO can be selectively isomerized to produce mostly trans-isocarveol, which we discovered is the preferred isomer for making perillyl alcohol by direct isomerization.

Abstract: A process for making perillyl alcohol is disclosed. The process comprises isomerizing a starting material comprising trans-isocarveol at a temperature within the range of 100° C. to 220° C. in the presence of a Group 5 metal catalyst to produce perillyl alcohol. We surprisingly found that trans-isocarveol, which can be selectively produced from a commercially available mixture of cis- and trans-LMO, can be isomerized directly to perillyl alcohol. Yields of perillyl alcohol are improved when the isomerization is performed under an inert atmosphere and/or in the presence of a phenolic antioxidant. Performing the isomerization in the presence of a high-boiling alcohol and/or distilling the perillyl alcohol product from the reaction mixture in the presence of a high-boiling alcohol, enhances yields and maximizes catalyst use. The resulting distillation residue, which contains recovered Group 5 metal catalyst, is valuable for catalyzing additional trans-isocarveol isomerizations.

Abstract: A two-step aldol condensation process is disclosed. ?-Campholenic aldehyde (ACA) and methyl ethyl ketone (MEK) react in the presence of a base under conditions effective to produce a mixture comprising a high yield of ketol condensation products. Dehydration of the ketols in the presence of an organic sulfonic acid provides unsaturated ketones that are valuable intermediates for fragrance components for synthetic sandalwood products. Compared with the usual one-step, base-catalyzed approach, the two-step process increases the yield of all condensation products and maximizes production of the most valuable ketone isomers.

Abstract: A process for the manufacture of an alpha, beta-unsaturated cyclic ketone, such as carvone, comprises the dehydrogenation of a secondary allylic cyclic alcohol, such as carveol, in the presence of at least one metal carboxylate. The process can be performed in a batchwise or continuous mode. Examples of suitable metal carboxylates include magnesium stearate, calcium 2-ethylhexanoate, and zinc 2-ethylhexanoate.

Abstract: A catalyst system comprising a primary catalyst chosen from one or more homogeneous or heterogeneous, inorganic, organic or complex metal-containing compound; and one or more phenolic activator/modifier(s). The catalyst system can be used for the preparation of allylic alcohols by rearrangement of corresponding epoxides, the subsequent Oppenauer type oxidation of allylic alcohols to alpha, beta-unsaturated carbonyl compounds, and/or the preparation of alpha, beta-unsaturated carbonyl compounds by rearrangement of epoxides to corresponding allylic alcohols followed by the subsequent Oppenauer type oxidation of allylic alcohols in a one pot process.

Abstract: A process for the manufacture of an alpha, beta-unsaturated cyclic ketone, such as carvone, comprises the dehydrogenation of a secondary allylic cyclic alcohol, such as carveol, in the presence of at least one metal carboxylate. The process can be performed in a batchwise or continuous mode. Examples of suitable metal carboxylates include magnesium stearate, calcium 2-ethylhexanoate, and zinc 2-ethylhexanoate.

Abstract: A catalyst system that can be used to achieve (a) preparation of allylic alcohols by rearrangement of the corresponding epoxide, when the allylic alcohol is a desired product; (b) subsequent reaction, e.g., selective oxidation, of the allylic alcohols obtained in step (a) to afford a desired product, e.g., alpha, beta-unsaturated carbonyl compounds; and/or (c) the ability to perform steps a) and b) in a one-pot process. In one embodiment, the catalyst system includes (i) at least one primary catalyst includes one or more homogeneous or heterogeneous, inorganic, organic or complex metal-containing compound, and (ii) at least one activator/modifier comprising at least one phenolic compound.