Abstract: A lactone compound is represented by general formula (A), and an ether compound is represented by general formula (B). In formula (A), R is a hydrogen atom or R1. When R is a hydrogen atom, R? is R1, the carbon bond (1) is a single bond or a double bond, and the carbon bond (2) is a single bond. When R is R1, R? is a hydrogen atom or R1, both the carbon bonds (1) and (2) are a single bond, or one of them is a double bond and the other is a single bond. In formula (B), R? is R1. R1 represents a specific alkyl group, a specific alkenyl group, a specific alkynyl group, or an aryl group. In formulas (A) and (B), n is 0 or 1.

Abstract: A cooling agent composition contains a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1). The symbol * represents an asymmetric carbon atom. X represents NH, N(ZAr2), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Ar2 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. Y each independently represents a methylene group which may have a substituent, and n represents an integer of 0 to 3. Ar1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent.

Abstract: A cooling agent composition includes a methyl menthol derivative represented by the following general formula (1). In the formula (1), a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.

Abstract: A lactone compound is represented by general formula (A), and an ether compound is represented by general formula (B). In formula (A), R is a hydrogen atom or R1. When R is a hydrogen atom, R? is R1, the carbon bond (1) is a single bond or a double bond, and the carbon bond (2) is a single bond. When R is R1, R? is a hydrogen atom or R1, both the carbon bonds (1) and (2) are a single bond, or one of them is a double bond and the other is a single bond. In formula (B), R? is R1. R1 represents a specific alkyl group, a specific alkenyl group, a specific alkynyl group, or an aryl group. In formulas (A) and (B), n is 0 or 1.

Abstract: A cooling agent composition contains a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1). The symbol * represents an asymmetric carbon atom. X represents NH, N(ZAr2), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Ar2 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. Y each independently represents a methylene group which may have a substituent, and n represents an integer of 0 to 3. Ar1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent.

Abstract: A cooling agent composition includes a methyl menthol derivative represented by the following general formula (1). In the formula (1), a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.

Abstract: The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

Abstract: The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

Abstract: An aluminum catalyst is obtained by reacting at least one compound of a specific alkylaluminum compound and a specific hydridoaluminum compound with a specific hydroxy compound. The specific hydroxyl compound is a specific 2-cycloalkyl-6-arylphenol or a specific di(2-cycloalkyl-6-arylphenol). A method for producing isopulegol or optically active isopulegol includes selectively cyclizing citronellal using the aluminum catalyst.

Abstract: A method for producing an optically active isopulegol includes asymmetrically isomerizing a specific compound in the presence of a ruthenium catalyst and a base, thereby giving an optically active citronellal, and selectively cyclizing the optically active citronellal in the presence of an aluminum catalyst. The aluminum catalyst is obtained by reacting a specific hydroxy compound and at least one aluminum compound selected from a specific alkylaluminum compound, a specific hydride aluminum compound, a specific linear aluminoxane and a specific cyclic aluminoxane.

Abstract: An aluminum catalyst is obtained by reacting at least one compound of a specific alkylaluminum compound and a specific hydridoaluminum compound with a specific hydroxy compound. The specific hydroxyl compound is a specific 2-cycloalkyl-6-arylphenol or a specific di(2-cycloalkyl-6-arylphenol). A method for producing isopulegol or optically active isopulegol includes selectively cyclizing citronellal using the aluminum catalyst.

Abstract: An object of the present invention is to provide a method for manufacturing an optically active menthol having fewer steps, which generates less environmentally polluting waste because a catalytic reaction is involved in all of the steps, and is capable of saving a production cost. The present invention relates to a method for manufacturing an optically active menthol, including the following steps: A-1) asymmetrically hydrogenating at least one of geranial and neral to thereby obtain an optically active citronellal, B-1) conducting a ring-closure reaction of the optically active citronellal in the presence of an acid catalyst to thereby obtain an optically active isopulegol, and C-1) hydrogenating the optically active isopulegol to thereby obtain an optically active menthol.

Abstract: To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al2(L1)n(L2)3-n]m.

Abstract: Provided is a process in which cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, increases the ratio of a particular optical isomer not only in a cyclized compound, but also in an unreacted compound. The process comprises performing, in the presence of a specified aluminum complex represented by the general formula: [Al2(L1)n(L2)3-n]m, cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, to increase the ratio of a particular optical isomer.

Abstract: A catalyst for obtaining isopulegol of high diastereoselectivity by highly selective cyclization reaction of citronellal is provided. The present invention relates to an organoaluminum compound obtained by reacting at least one organoaluminumoxy compound selected from the group consisting of chain aluminoxanes, cyclic aluminoxanes and bis(dialkylaluminumoxy)alkylboranes, with at least one hydroxy compound selected from the group consisting of diarylphenols, bis(diarylphenol) compounds, biaryldiols, dimethanols and silanols.

Abstract: To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al1(L1)1(L2)m(Lh)n]k.

Abstract: A catalyst for obtaining isopulegol of high diastereoselectivity by highly selective cyclization reaction of citronellal is provided. The present invention relates to an organoaluminum compound obtained by reacting at least one organoaluminumoxy compound selected from the group consisting of chain aluminoxanes, cyclic aluminoxanes and bis(dialkylaluminumoxy)alkylboranes, with at least one hydroxy compound selected from the group consisting of diarylphenols, bis(diarylphenol) compounds, biaryldiols, dimethanols and silanols.

Abstract: To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al2(L1)n(L2)3-n]m.

Abstract: Provided is a process in which cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, increases the ratio of a particular optical isomer not only in a cyclized compound, but also in an unreacted compound. The process comprises performing, in the presence of a specified aluminum complex represented by the general formula: [Al2(L1)n(L2)3-m]m, cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, to increase the ratio of a particular optical isomer.

Abstract: Provision of a novel platinum complex which is useful as a material for a light-emitting device of good light emission characteristic and light emission efficiency, and a novel light-emitting material that may be utilized in various fields. A platinum complex represented by the following general formula (1): (in which two rings of ring A, ring B, ring C, and ring D represent nitrogen-containing heterocyclic rings which may have a substituent and the remaining two rings of them represent aryl rings or hetero aryl rings which may have a substituent, the ring A and the ring B, the ring A and the ring C or/and the ring B and the rind D may form condensed rings. Two of X1, X2, X3, and X4 represent nitrogen atoms coordination bonded to a platinum atom and the remaining two of them represent carbon atoms or nitrogen atoms.