AROMATIC MIXTURE FOR REDUCING THE ODOR OR TASTE OF BIOGENIC AMINES

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.

Claims

1. An aroma mixture comprising a first component comprising a molecule selected from the group comprising molecules of the following structure (I): ##STR00006## wherein represents a single or double bond, wherein, allenes are excluded, R.sup.1 is selected from hydrogen or methyl, R.sup.2 is O or OH, and R.sup.3 is selected from methyl, ethyl, propyl, isopropyl or propenyl, molecules of the following structure (II): ##STR00007## wherein represents a single or double bond, wherein allenes or cumulene structures are excluded, R.sup.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): ##STR00008## wherein represents a single or double bond, wherein, allenes are excluded, R.sup.1 is selected from hydrogen or methyl, R.sup.2 is O or OH, and R.sup.3 is selected from methyl, ethyl, propyl, isopropyl or propenyl, molecules of the following structure (II): ##STR00009## wherein represents a single or double bond, wherein allenes or cumulene structures are excluded, R.sup.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.

Description

EXAMPLE 1

Reduction of Unpleasant Notes in Soy Sauce Containing Biogenic Amines

[0190] For the experiments, a commercially available soy sauce is used which, after analysis, contains 6 ppm phenylethylamine, 1.6 ppm histamine, 1.8 ppm cadaverine and 11.9 ppm putrescine and is regularly rated by the panelists as being too intensively animalistic—fishy, smelly, metallically fermented.

[0191] The panelists (n=6-8) rate the attributes animalistic—fishy, metallic as well as woody, sweet, flowery and terpenic, herbal on an unstructured scale from 0 (no taste)—10 (strong taste). The panelists receive the product alone in one sample and the product mixed with a quantity of substances listed in the table in another sample. Thereby, the order is arbitrary and not known by the panelists beforehand. The following table summarizes the results of the examination.

TABLE-US-00001 Odor description (indication of relative change Soy sauce with biogenic in percent) amines and an added Dosage of the Animalistic- Woody, amount of the following compound in fishy, sweet, Terpenig, compounds mg/kg metallic flowery herbal Madranol 1 −13.9 6.6 −6.0 Beta ionone 2 2.4 51.9 −28.9 Timberol 1 −26.5 27.9 −3.8 Cycloionone 0.5 2.3 33.8 19.6 Alpha ionone 1 −20.5 −4.4 −7.6 Tabanon 1 −18.8 13.7 −8.2 Dihydroionone 0.5 8.9 9.5 −8.3 5-Methyl-6,7- 0.5 −7.4 −10.0 −5.2 dihydrocyclopentapyrazine Beta epoxyionone 0.5 −5.4 22.8 21.1

EXAMPLE 2

Reduction of Unpleasant Notes of Fish Sauce—Triangle Test

[0192] Commercially available fish sauces are used for the experiments and one is selected from these which, after analysis, contains 8 ppm phenylethylamine, 99 ppm histamine, 121 ppm cadaverine and 61 ppm putrescine and which, compared to the other fish sauces, is regarded as too intensely animalistic—fishy, smelly, metallically fermented by the panelists. The panelists received the following instruction: Please smell the three samples and mark the sensorially deviating samples with a cross. In any case, one of the samples must be ticked, even if no difference can be noted.

TABLE-US-00002 Fish sauce with biogenic amines and an added Dosage of the amount of the following compound in compounds mg/kg Odor description Alpha-Ionol 0.5 bready, earthy, rounded Isocyclocitral 1 bready, rounded, sweet, caramel note, hay-like 5-Methyl-6,7- 0.05 not fishy, less silage notes, dihydrocyclopentapyrazine slightly roasted, earthy 4,6,8- 0.5 bready, less Megastigmatrien-3-one silage notes, (Tabanon) sweeter, less fishy Alpha ionone 0.1 bready, earthy, rounded, light cocoa note 2,3-Diethyl-5-methyl- 0.1 metallic, dusty, pyrazine Alpha-damascone 0.2 cocoa note, sweet, mild, not bready Beta ionone 0.5 less silage notes, bready, mild

EXAMPLE 3

Use of an Aroma Mixture Containing Both Components

[0193] Two aroma mixtures A and B with the following composition were used for further experiments:

[0194] Aroma Mixture A:

TABLE-US-00003 α-Ionone 0.4 wt. % α-Damascone 0.6 wt. % Dimethylpyrazine 0.2 wt. % Triglyceride vegetable oil 98.8 wt. %

[0195] Aroma Mixture B:

TABLE-US-00004 β-Damascenone 0.2 wt. % 5-Methyl-6,7-dihydro-cyclopentapyrazine 0.6 wt. % 5-Methyl-6,7-dihydro-cyclohexen-1-one 0.8 wt. % Triglyceride vegetable oil 98.4 wt. %

[0196] These aroma mixtures were now added to foodstuffs and, analogous to example 3, evaluated for their odor (each with 5 panelists).

[0197] The results are shown in the following table:

TABLE-US-00005 Share in % (relative Sensory Aroma to the evaluation Sample mixture foodstuff) (n = 5) 1 Fish sauce fishy, sweaty, animalistic, (10% in water) pungent, salty, umami 2 Fish sauce A 0.005 less fishy, rounder, more (10% in water) pleasant compared to 1 3 Fish sauce B 0.001 less fishy, rounder, umami, (10% in water) roaster compared to 1 4 Dark top- malty, sweet, fermented bitter, burnt, beer greasy, spicy 5 Dark top- A 0.01 malty, less bitter, more fermented fullness, more pleasant beer compared to 4 6 Dark top- B 0.025 more pleasant, less bitter, fermented malty, sweeter beer compared to 4 7 Organic sour, fermented, fruity, sauerkraut carbonaceous, sulfurous, juice umami 8 Organic A 0.01 less fermented and sauerkraut sour than juice 7, carbonaceous 9 Organic B 0.1 carbonaceous, sweet, less sauerkraut fermented and sour compared juice to 7 10 milk with bitter, malty, fruity, cocoa chocolaty, sweet, creamy 11 milk with A 0.02 rounder, less bitter, cocoa chocolaty, sweeter compared to 10 12 milk with B 0.005 rounder, less bitter, cocoa chocolaty, roasted, sweeter compared to 10 13 Zweigelt astringent, fruity, red wine berry, bitter 14 Zweigelt A 0.001 more harmonious, less red wine astringent, fruity, berry compared to 13 15 Zweigelt B 0.005 more harmonious, less red wine astringent, fruity, berry compared to 13 16 Pork roasted, animalistic, greasy, Jerky sulfurous 17 Pork A 0.02 roasted, sulfurous, greasy, Jerky balanced 18 Pork B 0.04 roasted, greasy, sulfurous Jerky balanced 19 Liquid special ammoniacal, fishy, food metallic 20 Liquid special A 0.02 less pungent ammoniacal, food fatty-metallic, fishy 21 Liquid special B 0.04 less ammoniacal and fishy, food metallic

[0198] One can see very clearly how a combination of the two components has a positive effect on the taste of all samples tested.

[0199] The individual combinations of the components and characteristics of the above-mentioned embodiments are exemplary; the exchange and substitution of these teachings with other teachings contained in this publication with the cited publications are also explicitly considered. The skilled person recognizes that variations, modifications and other embodiments described here may also occur without deviating from the inventive idea and the scope of the invention. Accordingly, the above description is to be considered as exemplary and not restrictive. The word ‘comprising’ used in the claims does not exclude other components or steps. The indefinite article “an” does not exclude the meaning of a plural. The mere fact that certain measures are recited in mutually different claims does not emphasize that a combination of those measures cannot be used advantageously. The scope of the invention is defined in the following claims and the corresponding equivalents.