(3R)-L-menthyl 3-hydroxybutyrate, process for producing the same, and sensate composition comprising the same
AssigneeTakasago International Corporation
InventorsKazuma Hojo, Takashi Aida, Kenya Ishida
Life of this patent
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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. The present invention relates to, as a cooling component or sensate component, (3R)-1-menthyl 3-hydroxybutyrate represented by the following formula (I):
Claims16
A cooling agent comprising (3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I):
- wherein an optical purity at the 3-position hydroxyl group of the (3R)-1-menthyl 3-hydroxybutyrate is 50% e.e. or more.
A sensate composition comprising:
- (3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I):
- and
- at least one component selected from the group consisting of a cooling component other than the (3R)-1-menthyl 3-hydroxybutyrate and a warming component,
- wherein an optical purity at the 3-position hydroxyl group of the (3R)-1-menthyl 3-hydroxybutyrate is 50% e.e. or more.
A flavor or fragrance composition comprising (3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I) in an amount of 0.001 to 90 weight % based on the total amount of the flavor or fragrance composition:
- wherein an optical purity at the 3-position hydroxyl group of the (3R)-1-menthyl 3-hydroxybutyrate is 50% e.e. or more.
A product comprising (3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I) in an amount of 0.0001 to 30 weight % based on the total amount of the product:
- wherein an optical purity at the 3-position hydroxyl group of the (3R)-1-menthyl 3-hydroxybutyrate is 50% e.e. or more, and
- wherein the product is selected from the group consisting of a food or drink, a fragrance or cosmetic, a daily necessities and household goods, an oral composition and a pharmaceutical.
A method for producing (3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I), wherein an optical purity at the 3-position hydroxyl group of the (3R)-1-menthyl 3-hydroxybutyrate is 50% e.e. or more:
- which comprises subjecting 1-menthyl acetoacetate represented by the formula (II) to asymmetric hydrogenation:
A method for imparting a cooling sensation to a flavor or fragrance composition, a food or drink, a fragrance or cosmetic, a daily necessities and household goods, an oral composition or a pharmaceutical, which comprises adding (3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I) to the flavor or fragrance composition, food or drink, fragrance or cosmetic, daily necessities and household goods, oral composition or pharmaceutical:
- wherein an optical purity at the 3-position hydroxyl group of the (3R)-1-menthyl 3-hydroxybutyrate is 50% e.e. or more.
(3R)-1-menthyl 3-hydroxybutyrate represented by the formula (I) having an optical purity of 50% e.e. or more at the 3-position hydroxyl group:
Dependencies are inferred from the claim text.