Abstract: A method for manufacturing isopulegol includes the step of diastereoselective ring-closing a citronellal using an aluminum compound of formula (1) below. In formula (1), X represents a halogen atom, Y represents a halogen atom or a hydrogen atom, and R1 represents a phenyl group or a cycloalkyl group of 5 to 12 carbons.

Abstract: A method for manufacturing isopulegol includes the step of diastereoselective ring-closing a citronellal using an aluminum compound of formula (1) below. In formula (1), X represents a halogen atom, Y represents a halogen atom or a hydrogen atom, and R1 represents a phenyl group or a cycloalkyl group of 5 to 12 carbons.

Abstract: An object of the present invention is to provide a method for producing an ether compound easily in a small number of steps at lower costs in high yields. The present invention relates to a method in which the ether compound represented by the general formula (1) is produced by reacting the specific carbonyl compound specified in the general formula (2) and the specific dialkoxy compound specified in the general formula (3) with hydrogen in the presence of a hydrogenation catalyst and an acidic substance to perform hydrogenation.

Abstract: An object of the present invention is to provide a method for producing an ether compound easily in a small number of steps at lower costs in high yields. The present invention relates to a method in which the ether compound represented by the general formula (1) is produced by reacting the specific carbonyl compound specified in the general formula (2) and the specific dialkoxy compound specified in the general formula (3) with hydrogen in the presence of a hydrogenation catalyst and an acidic substance to perform hydrogenation.

Abstract: The present invention relates to a p-menthane-3,8-diol isomer mixture 50% by mass or more of which is constituted of (1S)-isomers and a cooling sensation composition containing this mixture. The present invention also relates to a flavor and/or fragrance composition, food, beverage, cosmetic, daily use product, oral cavity composition, or pharmaceutical containing the p-menthane-3,8-diol isomer mixture in an amount of 0.0001 to 90% by mass.

Abstract: The present invention relates to a method comprising (A) reacting a ?-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an ?-methyl-?-keto acid; and (C) reducing the resulting ?-methyl-?-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

Abstract: The present invention relates to a method comprising (A) reacting a ?-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an ?-methyl-?-keto acid; and (C) reducing the resulting ?-methyl-?-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

Abstract: The present invention relates to a method comprising (A) reacting a ?-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an ?-methyl-?-keto acid; and (C) reducing the resulting ?-methyl-?-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

Abstract: Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH2 or CH?CH, n represents an integer of 0 to 4 when A is CH2, or 1 when A is CH?CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.

Abstract: The present invention relates to a method comprising (A) reacting a ?-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an ?-methyl-?-keto acid; and (C) reducing the resulting ?-methyl-?-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

Abstract: Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH2 or CH?CH, n represents an integer of 0 to 4 when A is CH2, or 1 when A is CH?CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.