Aromatic mixture for reducing the odor or taste of biogenic amines

Patent metadata

Field	Value
Publication number	US-2021127719-A1
Application number	US-201616471409-A
Country	US
Kind code	A1
Filing date	Dec 20, 2016
Priority date	Dec 20, 2016
Publication date	May 6, 2021
Grant date	—

Abstract

The present invention relates to an aroma mixture or a foodstuff comprising an ionone or a related compound as well as an alkylated 1,4-pyrazine. Hereby, the unpleasant taste and odor of biogenic amines can be reduced.

First claim

1 . An aroma mixture comprising a first component comprising a molecule selected from the group comprising molecules of the following structure (I):

wherein represents a single or double bond, wherein, allenes are excluded,
R 1 is selected from hydrogen or methyl,
R 2 is O or OH, and
R 3 is selected from methyl, ethyl, propyl, isopropyl or propenyl,
molecules of the following structure (II):

wherein represents a single or double bond, wherein allenes or cumulene structures are excluded,
R 4 is selected from hydrogen and propenyl,
2,5,5,8a-tetramethyl-7,8-dihydro-6H-chromene (cyclo-ionone), 4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one (dihydroactinidiolide), (E)-4-(1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl)but-3-en-2-one (5,6-epoxy ionone),
2-(2,6,6-trimethylcyclohex-1-en-1-yl) acetaldehyde (β-homocyclocitral), (4E)-4-[(E)-but-2-enylidene]-3,5,5-trimethyl-cyclohex-2-en-1-one (Tabanon), (E)-1-(2,4,4-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (α-isodamascone), and 4,4,7-trimethyl-3,6,7,8-tetrahydronaphthalen-2-one,
or mixtures thereof,
as well as a second component comprising an alkylated 1,4-pyrazine having one to four alkyl carbons.

2 . A foodstuff or foodstuff preparation comprising a biogenic amine and the first and second components of claim 1 , wherein the first and second components are independently present in the foodstuff or foodstuff preparation in at least a concentration of ≥1 μg/kg.

3 . A method of reducing and/or masking the taste and/or odor of biogenic amines comprising,
adding a first component comprising a molecule selected from the group comprising molecules of the following structure (I):

wherein represents a single or double bond, wherein, allenes are excluded,
R 1 is selected from hydrogen or methyl,
R 2 is O or OH, and
R 3 is selected from methyl, ethyl, propyl, isopropyl or propenyl,
molecules of the following structure (II):

wherein represents a single or double bond, wherein allenes or cumulene structures are excluded,
R 4 is selected from hydrogen and propenyl,
2,5,5,8a-tetramethyl-7,8-dihydro-6H-chromene (cyclo-ionone), 4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one (dihydroactinidiolide), (E)-4-(1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl)but-3-en-2-one (5,6-epoxy ionone),
2-(2,6,6-trimethylcyclohex-1-en-1-yl) acetaldehyde (β-homocyclocitral), (4E)-4-[(E)-but-2-enylidene]-3,5,5-trimethyl-cyclohex-2-en-1-one (Tabanon), (E)-1-(2,4,4-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (α-isodamascone), and 4,4,7-trimethyl-3,6,7,8-tetrahydronaphthalen-2-one,
or mixtures thereof,
or a second component comprising an alkylated 1,4-pyrazine having one to four alkyl carbons to an aroma mixture.

4 . The aroma mixture according to claim 1 , wherein the first component comprises at least one molecule selected from the group comprising:
(E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one (β-ionone), (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (α-ionone), (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol (α-lonol), (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ol (β-lonol), 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol (Madranol), 1-(2,2,6-trimethylcyclohexyl) hexan-3-ol (Timberol), 2,5,5,8a-tetramethyl-7,8-dihydro-6H-chromene (cyclo ionone), 4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one (dihydroactinidiolide), (E)-4-(1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl)but-3-en-2-one (5,6-epoxy-ionone), (E)-1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one (δ-damascone), (E)-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one (β-damascone), (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (α-damascone), (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one (β-damascenone), 2-(2,6,6-trimethylcyclohex-1-en-1-yl) acetaldehyde (β-homocyclocitral), 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde (β-cyclocitral), (E)-1-(2,4,4-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (α-isodamascone), (4E)-4-[(E)-but-2-enylidene]-3,5,5-trimethyl-cyclohex-2-en-1-one (Tabanon), and 4,4,7-trimethyl-3,6,7,8-tetrahydronaphthalen-2-one, or mixtures thereof.

5 . An aroma mixture according to claim 1 , wherein the first component comprises at least one molecule selected from the group comprising of 5-methyl-6,7-dihydro-5H-cyclopenta[b]pyrazine, 2,3-diethyl-5-methyl-pyrazine, 2-ethyl-3,5-dimethyl-pyrazine, and 3-ethyl-2,5-dimethyl-pyrazine, or mixtures thereof.

6 . A ready-made product containing an aroma mixture according to claim 1 .

7 . A cosmetic agent containing an aroma mixture according to claim 1 .

8 . A pharmaceutical preparation for the protection of the human or animal body containing an aroma mixture according to claim 1 .

9 . The method of claim 3 , comprising adding both the first component and the second component to the aroma mixture.

10 . The aroma mixture according to claim 4 , wherein the first component comprises at least one molecule selected from the group comprising of 5-methyl-6,7-dihydro-5H-cyclopenta[b]pyrazine, 2,3-diethyl-5-methyl-pyrazine, 2-ethyl-3,5-dimethyl-pyrazine, and 3-ethyl-2,5-dimethyl-pyrazine, or mixtures thereof.

11 . A ready-made product containing an aroma mixture according to claim 4 .

12 . A ready-made product containing an aroma mixture according to claim 5 .

13 . A ready-made product containing a foodstuff according to claim 3 .

14 . A cosmetic agent containing an aroma mixture according claim 4 .

15 . A cosmetic agent containing an aroma mixture according to claim 5 .

16 . A pharmaceutical preparation for the protection of the human or animal body containing an aroma mixture according to claim 4 .

17 . A pharmaceutical preparation for the protection of the human or animal body containing an aroma mixture according to claim 5 .

Assignees

• Symrise Ag

Inventors

• Kiefl Johannes
• Schaefer Uwe
• Kohlenberg Birgit
• Henze Thomas
• Korte Stephanie

Classifications

• A23L27/84 Primary

  Flavour masking or reducing agents · CPC title

• C11B9/0076

  the hetero rings containing less than six atoms · CPC title

• A23L5/27 Primary

  by chemical treatment, by adsorption or by absorption · CPC title

• A61K8/35

  Ketones, e.g. benzophenone · CPC title

• A23L27/50

  Soya sauce · CPC title