Takasago International Corporation

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Takasago International Coporation

Takashi Aida

Kenya Ishida

Hiroyuki Matsuda

Tetsuro Yamasaki

Kazuma Hojo

Akira Amano

Andrew T Lupo

Makoto Harada

Hisao Iwai

Kazuki Sugiyama

Junko Nagano

Kunihide Hoshino

Takeshi Yamamoto

John Ryan Caldwell

Toshimitsu Hagiwara

Kenichi Yamamoto

Kenji Maruyama

Tetsuya Yamamoto

Michael E Lankin

Tetsuo Nakatsu

Carter B Green

Yuichiro Yamazaki

Kazuhiko Tokoro

Eiko Tamai

Yasuhiro Komatsuki

Fumihiro Yanaka

Kyoko Hirano

Tetsuya Nagasawa

Yasuko Matsumura

Tsunehide Yoneyama

Tomoko Yamamoto

The present invention provides a compound represented by general formula (1). (In the formula, Rrepresents an alkyl group having 2 to 9 carbon atoms, an alkenyl group having 2 to 9 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms which may have a substituent, or a phenyl group which may have a substituent; Rrepresents an alkyl group having 1 to 3 carbon atoms; Rto Rindependently represent a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms; Rrepresents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms which may have a substituent, or an alkoxy group having 1 to 5 carbon atoms; n represents 0 or 1; and the wavy line represents a cis form, a trans form or a mixture of a cis form and a trans form.)

Compound, and flavor and/or fragrance composition containing said compound

The present invention relates to a fragrance composition that has a vanilla odor property, that is chemically stable and that can be blended in a variety of products, which can be an alternative material for vanillin or ethyl vanillin. The fragrance composition of the present invention comprises: A) one or more selected from the group consisting of vanillyl alcohol, ethylvanillyl alcohol, isovanillyl alcohol and veratryl alcohol; and B) one or more selected from the group consisting of 2-ethoxy-4-methylphenol, 2-methoxy-4-methylphenol, 2-ethoxy-5-methylphenol, 2-ethoxy-4-ethylphenol, 2-ethoxy-5-ethylphenol, 2-methoxy-p-cresol methyl carbonate and 2-ethoxy-5-(1-propenyl)-phenol, wherein the total content of component A and component B in the fragrance composition is 0.01-90% by mass, and the mixing ratio of component A and component B (on a mass basis) is in a range of 99:1-70:30.

Fragrance composition

Disclosed is 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. Also disclosed is a cooling agent comprising (3S)-1-menthyl 3-hydroxybutyrate represented by the following formula (I) 

Process for producing (3S)-1-menthyl 3-hydroxybutyrate and sensate composition

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.

Vanillin acetals and sensory stimulant composition containing the same

A cooling sensation agent composition with a prolonged cool sensation effect is provided comprising at least one compound selected from the group consisting of aceia or ketal derivatives of 3-(1-menthoxy)propan-1,2-diol represented by Formula (1), single or mixed carbonic esters ol one or two kinds ol alcohols represented by Formula (2), and carboxylic esters represented by Formula (4). A sensory stimulation agoni composition, a flavor or fragrance composition, a beverage or food product, a perfume or cosmetic product, a toiletry product, a daily utensil product or grocery, a fiber, a fiber product, a cloth or a medicine comprising the cooling sensation agent composition; a production method thereof; a cooling processing method of a fiber, fiber product or a cloth, comprising compounding the cooling sensation agent; and new compounds are also provided.

Cooling sensation agent composition and sensory stimulation agent composition

Disclosed is a method for producing (3S)-l-menthyl 3-hydroxybutyrate of the following formula (I) by subjecting l-menthyl acetoacetate to asymmetric hydrogenation. The compound may be used as 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. 

Process for producing (3S)-I-menthyl 3-hydroxybutyrate and sensate composition

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. The present invention relates to, as a cooling component or sensate component, (3R)-1-menthyl 3-hydroxybutyrate represented by the following formula (I): 

(3R)-L-menthyl 3-hydroxybutyrate, process for producing the same, and sensate composition comprising the same

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 CHor CH&#x2550;CH, n represents an integer of 0 to 4 when A is CH, or 1 when A is CH&#x2550;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. 

Cooling sensation agent composition, sensory stimulation agent composition and use of the same

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. The present invention relates to a cooling agent comprising (3S)-1-menthyl 3-hydroxybutyrate represented by the following formula (I) 

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. 

Vanillin acetals

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. 

Flavor and fragrance composition

Disclosed is a 2-methyl-2-pentenyl ester represented by the general formula (1) [wherein R represents a hydrogen atom or a hydrocarbon group having 1 to 9 carbon atoms which may have a substituent]. The compound has a new-type, unprecedented aroma and/or flavor, particularly a fruity, greenish or floral aroma and/or flavor. The compound can be added to a flavor or fragrance composition in an amount of 0.001 to 30 wt %. The flavor or fragrance composition can be added to a cosmetic product, a toiletry product, a bath agent, a food, a beverage or a pharmaceutical product in an amount of 0.0001 to 30 wt %. All of the compounds of the general formula (1) are novel, except for those compounds of the general formula (1) wherein R represents a methyl group, an isopropyl group, a phenyl group or a mesityl group.

Flavor composition or fragrance composition, product containing the flavor composition or fragrance composition, and novel ester compound

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&#x3c;1&#x3e; represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms; R&#x3c;2&#x3e; and R&#x3c;3&#x3e; 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.

Menthol derivative and cooling agent composition comprising the same

It is to provide a hair dye stabilizer capable of stably storing a readily oxidizable compound in a hair dye, especially an oxidizing dye intermediate or a coupler and effective for remarkably improving the offensive odor problem. Furthermore, it is to provide a hair dye stabilizer giving improvement in damage on the hair, hardly irritating the skin, and free from adverse effects on the dyeing ability of the hair dye. As the active component constituting the hair dye stabilizer, a compound which is a mercapto-hydrocarbon compound and/or a thiol alcohol compound and does not contain a functional group reactive with a dye intermediate or a coupler is used. A readily oxidizable compound and the like in a hair dye can be stably stored by the use of an extremely small amount of the stabilizer.

Hair dye stabilizer

The present invention relates to a stable composition for hair dye, which comprises at least one compound selected from dihydrocitronellyl nitrile, 2,2,6-trimethylcyclohexane carboxylic acid ethyl ester, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 2,2,6-trimethylcyclohexyl-3-hexanol, 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol, thioglycerin, dibutyl sulfide, thiogeraniol, thiocineol, 2-methyl-4-propyl-1,3-oxathian, 4-methoxy-2-methyl-2-butanethiol and the like. The stable composition for hair dye has a superior effect in masking a malodor originated from components such as ammonia formulated in hair dye composition such as composition for hair dye, and is also stable in an alkaline product and an acidic solution product.

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Kanagawa, Japan

Takashi Aida