Abstract: The invention relates to a sensory stimulant composition containing one or more of vanillin acetals represented by the general formula (1), and a flavor and fragrance composition, a beverage or food product, a fragrance or cosmetic product, a daily utensil product, an oral composition, or a pharmaceutical product containing the sensory stimulant composition with a warming sensation agent or cooling sensation substance, if necessary. Vanillin acetals represented by the general formula (1) show an excellent pungent and/or warming sensation effect and a cooling sensation-emphasizing effect.

Abstract: The invention relates to a sensory stimulant composition containing one or more of vanillin acetals represented by the general formula (1), and a flavor and fragrance composition, a beverage or food product, a fragrance or cosmetic product, a daily utensil product, an oral composition, or a pharmaceutical product containing the sensory stimulant composition with a warming sensation agent or cooling sensation substance, if necessary. Vanillin acetals represented by the general formula (1) show an excellent pungent and/or warming sensation effect and a cooling sensation-emphasizing effect.

Abstract: A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.

Abstract: Provided is an amide ester that is useful as an intermediate manufacturing product for an aroma compound such as spilanthol or the like. Also provided is a spilanthol manufacturing method using said amide ester. High-purity spilanthol can be manufactured by reacting an amide ester represented by general formula (1) with a basic compound. (In the formula, R1 represents a phenyl group that may be substituted with a C1-6 alkyl group and either a C1-4 alkyl group, a C1-4 alkoxy group, or a halogen atom; R2 represents a C1-8 hydrocarbon group; and the wavy lines represent cis configurations, trans configurations, or a mixture of the two configurations.

Abstract: A flavor and fragrance composition with a cooling sensation effect comprising 1-(2-hydroxy-4-methylcyclohexyl)ethanone represented by the formula (1). The flavor and fragrance composition is added to a beverage or food product, a fragrance or cosmetic product, a daily utensil product, an oral composition, or a pharmaceutical product in the range of 0.0001 to 20% by weight to the total weight of the flavor and fragrance composition added.

Abstract: The present invention provides a method for producing sulfur-containing carboxylic acid esters that are useful for aromatizing and flavoring purpose and can cater to the needs for diversified aromatized and/or flavored products, and to further provide a fragrance and/or flavor composition comprising the ester producible by the method and an aromatized and/or flavored product comprising the same. The sulfur-containing carboxylic acid ester is represented by the following formula (3): wherein R1 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group (wherein the substituent thereof is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms), R2 and R3 independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, or R2 and R3 together form an alkylene group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

Abstract: To provide a drug, quasi-drug, food or drink that can act as a gastric acid secretion suppressant or a potassium channel inhibitor by including a composition that can be safely used and can be inexpensively produced. Each of these products contains one or more cooling sensation compositions that are compounds providing cooling sensation in an amount sufficient for exhibiting the efficacy thereof in a living body to which the product is administered.

Abstract: Provided that a method for inexpensively producing optically active ?-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active ?-ionone obtained by the aforementioned method. A method for producing optically active ?-ionone, comprising allowing ?-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained ?-ionone enol ester; a method for producing optically active ?-ionone comprising subjecting ?-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active ?-ionol to react with an esterification agent to give an optically active ?-ionol ester, hydrolyzing the obtained optically active ?-ionol ester after purification as necessary, and then oxidizing the obtained optically active ?-ionol; and a perfume composition comprising thus obtained optically active ?-ionone.

Abstract: A simplified production method of stereoisomer of theaspiran having high optical purity has been desired. An alcohol compound having a specific skeleton is enantioselectively esterified with an enzyme, or an ester compound having a specific skeleton is enantioselectively hydrolyzed with an enzyme. The resultant optically active ester or optically active alcohol is used. Thus, optically active theaspiran having a desired configuration and having a high optical purity is obtained in a satisfactory yield.

Abstract: The invention relates to a cooling sensation agent composition with a prolonged cool sensation effect comprising at least one compound selected from Formula (1) wherein each of A and B is a hydrogen atom or a hydrocarbon group which may have one or more substituents, in which A and B are not hydrogen atoms simultaneously, and the total number of carbon atoms in A and B is in the range of 6 to 18; and Formulae (2) to (4) wherein R1, R2, and R3 each represent a residue of an alcohol selected from 1-menthol, 1-isopulegol, 3-(1-menthoxy)propan-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 2-methyl-3-(1-menthoxy)propan-1,2-diol and para-menthan-3,8-diol), and R4 represents a residue of a branched or straight-chain, cyclic or linear, or saturated or unsaturated alcohol having 6 to 18 carbon atoms that may have one or more aromatic rings that may have a condensed ring and substituent groups such as hydroxyl and ether groups; and R6 represents a hydrocarbon group having 11 to 19 carbon atoms that may

Abstract: Provided that a method for inexpensively producing optically active ?-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active ?-ionone obtained by the aforementioned method. A method for producing optically active ?-ionone, comprising allowing ?-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained ?-ionone enol ester; a method for producing optically active ?-ionone comprising subjecting ?-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active ?-ionol to react with an esterification agent to give an optically active ?-ionol ester, hydrolyzing the obtained optically active ?-ionol ester after purification as necessary, and then oxidizing the obtained optically active ?-ionol; and a perfume composition comprising thus obtained optically active ?-ionone.

Abstract: A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.

Abstract: The invention relates to a method for producing an azoline compound represented by the general formula (3): wherein R1 represents an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; R3, R4, R5 and R6 may be the same or different and each represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; two arbitrary groups selected from R3, R4, R5 and R6 may bond to each other to form a ring; and Z1 represents an oxygen atom, a sulfur atom or a selenium atom; comprising reacting a carboxylic acid or a carboxylic acid derivative represented by the general formula (1): R1CO2R2 ??(1) wherein R

Abstract: The invention relates to innovative menthol derivatives which are represented by the general formula (I) below and are excellent in a cooling effect and cool retaining effect, cooling agent compositions comprising the menthol derivatives, and sensory stimulation agent compositions containing the cooling agent compositions, as well as fragrance compositions, beverage or food products, cosmetic products, toiletry products, bathing agents, and pharmaceutical products containing the cooling agent compositions or sensory stimulation agent compositions. (general formula (I)) wherein R<1> represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms; R<2> and R<3> independently represent an alkylene group having 2 to 5 carbon atoms and optionally having a substituent; double dotted line represents a single bond or a double bond; and n is an integer of 1 to 3.

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 humectant composition containing, as component (A), at least one member selected from a menthol derivative represented by the following formula (1) and p-menthane-3,8-diol: in which R is an alkylene group having 2 to 5 carbon atoms which may be substituted with at least one member selected from the group consisting of a methyl group and a hydroxyl group, and n is an integer of 1 to 3. The humectant composition of the present invention provides an excellent moisture-retention effect.

Abstract: Provided that a method for inexpensively producing optically active ?-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active ?-ionone obtained by the aforementioned method. A method for producing optically active ?-ionone, comprising allowing ?-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained ?-ionone enol ester; a method for producing optically active ?-ionone comprising subjecting ?-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active ?-ionol to react with an esterification agent to give an optically active ?-ionol ester, hydrolyzing the obtained optically active ?-ionol ester after purification as necessary, and then oxidizing the obtained optically active ?-ionol; and a perfume composition comprising thus obtained optically active ?-ionone.

Abstract: The invention relates to a method for producing an azoline compound represented by the general formula (3): wherein R1 represents an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; R3, R4, R5 and R6 may be the same or different and each represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; two arbitrary groups selected from R3, R4, R5 and R6 may bond to each other to form a ring; and Z1 represents an oxygen atom, a sulfur atom or a selenium atom; comprising reacting a carboxylic acid or a carboxylic acid derivative represented by the general formula (1): R1CO2R2??(1) wherein R1

Abstract: The present invention provides a cooling component or sensate component which does not have undesirable stimulus feeling, bitterness and the like and is excellent in the persistence of refresh-feeling and cool-feeling, a sensate composition which comprises the same, and various products that comprise said sensate composition.

Abstract: The present invention provides a cooling component or sensate component which has further strong cooling intensity and is excellent in the persistency or refresh-feeling and cool-feeling, a sensate composition comprising the same, and various products comprising the sensate composition.