Flavor-enhancing compounds

Patent metadata

Field	Value
Publication number	US-9668497-B2
Application number	US-201514865203-A
Country	US
Kind code	B2
Filing date	Sep 25, 2015
Priority date	Sep 25, 2015
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

The present invention has discovered that 7,8-dihydroxy-2-phenyl-4H-chromen-4-one and a salt thereof have unexpected and advantageous cooling enhancement and modification properties. Thus, a composition comprising a cooling compound and an effective amount of 7,8-dihydroxy-2-phenyl-4H-chromen-4-one can be used to enhance or modify the cooling sensation in the mouth, in the nasal cavity and/or on the skin, and can also augment, enhance or impart a cooling sensation to products such as foodstuff, chewing gums, dental or oral hygiene products, topical products, nasal care products and toilet articles.

First claim

What is claimed is:

1. A cooling composition consisting of a cooling compound selected from the group consisting of menthol; menthyl methyl ether, menthyl lactate, menthyl formate, monomenthyl succinate, monomenthyl glutarate, menthyl acetoacetate; an acyclic amide; a cyclic amide; a cyclic amide with aromatic substitution; and a mixture thereof and an effective amount of 7,8-dihydroxy-2-phenyl-4H-chromen-4-one, wherein the effective amount is from about 10 to about 50 ppm by weight of the composition.

2. The cooling composition of claim 1 , wherein the cooling compound is selected from the group consisting of menthol, 2-isopropyl-N,2,3-trimethylbutyramide, N-ethyl-2,2-diisopropylbutanamide, N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropyl butanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethyl butanamide, ethyl menthane carboxamide, N-[(ethoxycarbonyl)methyl)-p-menthane-3-carboxamide, N-cyclopropyl-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide, menthyl pyrrolidone carboxylate, 4-[[[(2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]amino]-benzeneacetamide, N-p-benzeneacetonitrile-menthanecarboxamide, N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide and a mixture thereof.

3. The cooling composition of claim 2 , wherein the cooling compound is menthol.

4. A process of augmenting, enhancing or imparting a cooling sensation to a product selected from the group consisting of a foodstuff, a chewing gum, a dental or oral hygiene product, a topical product, a nasal care product and a toilet article comprising the step of incorporating the cooling composition according to claim 1 .

5. The process of claim 4 , wherein the cooling compound is selected from the group consisting of menthol, 2-isopropyl-N,2,3-trimethylbutyramide, N-ethyl-2,2-diisopropylbutanamide, N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropyl butanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethyl butanamide, ethyl menthane carboxamide, N-[(ethoxycarbonyl)methyl)-p-menthane-3-carboxamide, N-cyclopropyl-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide, menthyl pyrrolidone carboxylate, 4-[[[(2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]amino]-benzeneacetamide, N-p-benzeneacetonitrile-menthanecarboxamide, N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide and a mixture thereof.

6. The process of claim 5 , wherein the cooling compound is menthol.

7. A product selected from the group consisting of a foodstuff, a chewing gum, a dental or oral hygiene product, a topical product, a nasal care product and a toilet article comprising a cooling composition, wherein the cooling composition consisting of a cooling compound selected from the group consisting of menthol; menthyl methyl ether, menthyl lactate, menthyl formate, monomenthyl succinate, monomenthyl glutarate, menthyl acetoacetate; an acyclic amide; a cyclic amide; a cyclic amide with aromatic substitution; and a mixture thereof and an effective amount of 7,8-dihydroxy-2-phenyl-4H-chromen-4-one, and wherein the effective amount is from about 10 to about 50 ppm by weight of the composition.

8. The product of claim 7 , wherein the cooling compound is selected from the group consisting of menthol, 2-isopropyl-N,2,3-trimethylbutyramide, N-ethyl-2,2-diisopropylbutanamide, N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropyl butanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethyl butanamide, ethyl menthane carboxamide, N-[(ethoxycarbonyl)methyl)-p-menthane-3-carboxamide, N-cyclopropyl-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide, menthyl pyrrolidone carboxylate, 4-[[[(2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]amino]-benzeneacetamide, N-p-benzeneacetonitrile-menthanecarboxamide, N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide and a mixture thereof.

9. The product of claim 8 , wherein the cooling compound is menthol.

10. A cooling composition consisting of a cooling compound selected from the group consisting of menthol; menthyl methyl ether, menthyl lactate, menthyl formate, monomenthyl succinate, monomenthyl glutarate, menthyl acetoacetate; an acyclic amide; a cyclic amide; a cyclic amide with aromatic substitution; and a mixture thereof; an effective amount of 7,8-dihydroxy-2-phenyl-4H-chromen-4-one; and a material selected from the group consisting of a polymer and a non-polymer, wherein the effective amount is from about 10 to about 50 ppm by weight of the composition.

11. The cooling composition of claim 10 , wherein the non-polymer is selected from the group consisting of an oligomer, a surfactant, an emulsifier, a fat, a wax, a phospholipid, an organic oil, a mineral oil, a petrolatum, a natural oil, a perfume fixative, a fiber, a starch, a sugar and a solid surface material.

Assignees

• Int Flavors & Fragrances Inc

Inventors

• Wu Hou
• John Thumpalasseril V
• Tang Xiaoqing
• Kim Jung-A

Classifications

• A61Q11/00

  Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses · CPC title

• A61K8/498

  having 6-membered rings or their condensed derivatives, e.g. coumarin · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23G4/06 Primary

  characterised by the composition {containing organic or inorganic compounds} · CPC title

• A61K8/34

  Alcohols · CPC title