Mixtures with stabilising properties

Abstract

The present invention primarily relates to novel mixtures with stabilizing properties, particularly for avoiding, reducing or delaying the formation of sensorially undesired flavours and/or tastes in oxidative degradation processes or autoxidative processes or reducing, avoiding or delaying oxidative processes in one or more oxidation-sensitive compounds, particularly autoxidative processes, their use in specific preparations as well as novel preparations and methods of producing such preparations. Additionally, herein described are methods for decreasing, avoiding or delaying the formation of sensorially undesired flavours and/or tastes in oxidative degradation processes or autoxidative processes or for decreasing, avoiding or delaying oxidative processes in one or more oxidation-sensitive compounds, particularly autoxidative processes.

Claims

1. A mixture comprising: a) one or more monocyclic monoterpenes selected from the group consisting of gamma-terpinene, alpha-terpinene, beta-terpinene, beta-phellandrene, limonene, thymol, pulegone, carvacrol and alpha-phellandrene, b) one or more benzoic acid derivatives of formula (II) ##STR00007## with R1, R2 and R3 independently of each other selected from the group consisting of hydrogen, hydroxy group and methoxy group, c) a first 3-phenylpropenoic acid derivative of formula (IV) ##STR00008## with R1=1-carboxy-2-(3,4-dihydroxyphenyl)ethyl, R2=hydrogen and R3=hydrogen, optionally a second 3-phenylpropenoic acid derivative of formula (IV) with R1=5-carboxy-2,3,5-trihydroxycyclohexyl, R2=hydrogen and R3=hydrogen, and optionally a third 3-phenylpropenoic acid derivative of formula (IV) with R1=hydrogen, R2=hydrogen and R3=hydrogen, d) tartaric acid (formula (V)) D-(−)-form, and/or L-(+)-form, and/or meso-form ##STR00009## e) citric acid (formula (VI)) and/or malic acid (formula (VII)) ##STR00010## f) glucose, fructose and/or sucrose, g) 1,2-propanediol and/or 1,3-propanediol and/or propane-1,2,3-triol, h) water, i) optionally gallocatechin (Formula (III)) (2R,3S)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol ##STR00011## j) optionally, one or more further flavouring substances, and k) optionally, one or more further solvents, wherein the mixture comprises, with regard to the total weight of the mixture, respectively, 0.0001 to 20 wt.-% of component a), 0.0001 to 1.5 wt.-% of component b), 0.0001 to 3 wt.-% of component c), 0.005 to 10 wt.-% of component d), 0.005 to 10 wt.-% of component e), 0.000005 to 25 wt.-% of component f), 0.0001 to 98 wt.-% of component g), 0.0005 to 95 wt.-% of component h), 0.0001 to 1 wt.-% of component i), if present, 0.005 to 95 wt.-% of component j) if present, and 0.01 to 95 wt.-% of component k), if present.

2. The mixture according to claim 1, wherein the mixture has an Oxygen Radical Absorption Capacity value of greater than 200 μmol Trolox Equivalents/g, with respect to the dry weight of the mixture.

3. The mixture according to claim 1, wherein the mixture has a polyphenol content according to Folin-Ciocalteu of greater than 5%, with respect to the dry weight of the mixture.

4. The mixture according to claim 1, comprising, with regard to the total weight of the mixture, respectively, 0.001 to 10 wt.-% of component a), 0.001 to 1 wt.-% of component b), 0.001 to 1.5 wt.-% of component c), 0.0075 to 5 wt.-% of component d), 0.0075 to 8 wt.-% of component e), 0.0000075 to 15 wt.-% of component f), 0.0005 to 65 wt.-% of component g), 0.005 to 65 wt.-% of component h), 0.001 to 0.7 wt.-% of component i), 0.0075 to 50 wt.-% of component j), 0.05 to 65 wt.-% of component k).

5. The mixture according to claim 1, wherein the mixture is a flavour composition.

6. A preparation comprising a mixture according to claim 1 as well as one or more further components.

7. The preparation according to claim 6, wherein the or one, several or all of the further components, respectively, is/are selected from the group consisting of oxidation-sensitive compounds.

8. The preparation according to claim 6, wherein the mixture is contained in the preparation in an effective amount to reduce, avoid or delay the formation of sensorially undesired flavours and/or tastes in oxidative degradation processes or autoxidative processes or to reduce, avoid or delay oxidative processes in one or more oxidation-sensitive compounds.

9. The preparation according to claim 6, wherein the total amount of mixture in the preparation, with regard to the total weight of the preparation, is less than 5 wt.-%.

10. The mixture according to claim 1 having an Oxygen Radical Absorption Capacity value of greater than 500 μmol Trolox Equivalents/g, with respect to the dry weight of the mixture.

11. The mixture according to claim 1 having an Oxygen Radical Absorption Capacity value of greater than 2000 μmol Trolox Equivalents/g, with respect to the dry weight of the mixture.

12. The mixture according to claim 1 comprising the one or more further solvents of k), wherein the one or more further solvents of k) are selected from the group consisting of triacetin (TRI), isopropanol (iPr), isopropyl myristate (IPM), ethanol, dipropylene glycol (DPG), and triethyl citrate (TEC).

13. The mixture according to claim 1, comprising, with regard to the total weight of the mixture, respectively, 0.01 to 5 wt.-% of component a), 0.005 to 0.25 wt.-% of component b), 0.005 to 1 wt.-% of component c), 0.01 to 3 wt.-% of component d), 0.01 to 5 wt.-% of component e), 0.00001 to 10 wt.-% of component f), 0.001 to 45 wt.-% of component g), 0.01 to 50 wt.-% of component h), 0.005 to 0.5 wt.-% of component i), 0.01 to 25 wt.-% of component j), 0.1 to 45 wt.-% of component k).

14. The mixture according to claim 1, comprising, with regard to the total weight of the mixture, respectively, 0.1 to 1 wt.-% of component a), 0.01 to 0.1 wt.-% of component b), 0.01 to 0.7 wt.-% of component c), 0.01 to 0.5 wt.-% of component d), 0.01 to 3 wt.-% of component e), 0.00005 to 5 wt.-% of component f), 0.1 to 35 wt.-% of component g), 0.05 to 35 wt.-% of component h), 0.01 to 0.15 wt.-% of component i), 0.05 to 15 wt.-% of component j), 1 to 35 wt.-% of component k).

15. The mixture according to claim 1, wherein the mixture has a polyphenol content according to Folin-Ciocalteu of greater than 10%, with respect to the dry weight of the mixture.

16. The mixture according to claim 1, wherein the mixture has a polyphenol content according to Folin-Ciocalteu of greater than 15%, with respect to the dry weight of the mixture.

17. The mixture according to claim 1 comprising the (2R,3S)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol.

18. A method of producing a preparation according to claim 6, comprising: (i) providing components a) to h) as well as optionally i), j) and k) of the mixture, (ii) providing one or more further components, and (iii) mixing of the components provided in (i) and (ii).

19. A method for reducing, avoiding or delaying the formation of sensorially undesired flavours and/or tastes in oxidative degradation processes or autoxidative processes or reducing, avoiding or delaying of oxidative processes in one or more oxidation-sensitive compounds: (A) providing a mixture according to claim 1 or providing the components a) to h) as well as optionally i), j) and k), (B) providing one or more further components, wherein the further components, respectively, is/are selected from the group consisting of oxidation-sensitive compounds, and (C) mixing the components provided in steps (A) and (B).

Description

EXAMPLES

Example 1: Mixtures (According to the Invention

(1) TABLE-US-00001 TABLE Mixture examples M1 to M6 M1 M2 M3 M4 M5 M6 Component wt.-% wt.-% wt.-% wt.-% wt.-% wt.-% Supplier Thymol — 0.1813 0.0001 0.0006 0.0002 0.0011 Symrise Limonene 56.5544 0.5081 0.0098 0.0003 0.1013 0.0007 MCI Miritz gamma-Terpinene 6.5319 0.1190 0.0012 0.0001 0.0909 0.0003 Destillerias Munoz Galvez S. A. Carvone — 0.4113 0.0032 — 0.0082 0.0001 Sigma-Aldrich Pulegone — 0.1496 0.0021 — 0.0023 — Berje Inc. Carvacrol — 0.1889 0.0012 0.0002 0.0005 0.0001 Frutarom Gallic acid 0.1221 0.6671 0.0076 0.0311 0.5110 0.0293 Sigma-Aldrich 4-Hydroxy-3,5- — 0.8211 0.0098 0.0047 0.8722 0.0046 Alfa Aesar dimethoxybenzoic acid Benzoic acid — 0.0097 0.0097 — 0.0083 — IMCD Deutschland Gallocatechin 0.1165 0.6161 0.4487 0.0054 0.3101 0.0053 Sigma-Aldrich 3-(3,4- — 0.0022 — 0.0057 0.0210 0.0061 Sigma-Aldrich dihydrogphenyl)prop-2- enoic acid 3-(3,4-dihydroxyphenyl)- 0.0112 1.3361 1.5030 0.5656 1.4211 0.5733 Sigma-Aldrich 2-[3-(3,4- dihydrogphenyl)prop-2- enoyl]oxy-propionic acid 3-[3-(3,4- — 0.0001 0.1922 — 0.0022 — Sigma-Aldrich dihydrogphenyl)prop-2- enoyl]oxy-1,4,5- trihydroxy-cyclohexane- 1-carboxylic acid Tartaric acid 0.0550 5.5000 0.0115 2.0000 7.7010 2.1510 UD Chemie Citric acid 1.8000 2.8500 0.0100 1.1000 3.8329 1.4377 Sigma-Aldrich Malic acid 2.5000 3.3500 0.0103 1.1000 3.9412 1.3670 UD Chemie Glucose 4.5112 7.5101 0.0029 5.0000 5.5000 4.9733 Sigma-Aldrich Fructose 5.3831 8.8133 0.0026 6.6000 5.7000 6.4913 Danisco Sucrose 0.0052 5.0220 0.0032 1.2000 1.1000 1.1798 Nordzucker Water 8.1126 25.0900 0.0550 15.0000 25.0000 50.6485 Propylene glycol 14.2968 36.8540 97.7159 67.3863 43.8756 31.1305 Dow Sum 100.0000 100.0000 100.0000 100.0000 100.0000 100.0000

(2) For production, the solid ingredients are solved in the premixed solvents water and PG. If necessary, this preparation is slightly heated to max. 40° C. until everything is solved. Then the other ingredients were added after cooling to room temperature.

Example 2: Dressing (A, B: Comparative Examples; C: According to the Invention

(3) TABLE-US-00002 TABLE Dressing A B C Component wt.-% wt.-% wt.-% Sunflower oil 42.00 42.00 42.00 Water 25.26 25.16 25.16 Egg yolk, pasteurised 18.90 18.90 18.90 Vinegar 5% 5.91 5.91 5.91 Mod. corn starch C*Tex06205 4.15 4.15 4.15 Sucrose 2.30 2.30 2.30 Salt 1.38 1.38 1.38 Guar gum 0.10 0.10 0.10 Calcium-Disodium EDTA — 0.10 — Mixture M5 according to example 1 — — 0.10 Sum 100.00 100.00 100.00

(4) For production, the dry components are added to the water first and heated to 90° C., whereby this temperature is then kept for 3 minutes. Subsequently, the temperature is cooled to 25° C. and for sample B the EDTA and for sample C the mixture according to example 1 are added, respectively until everything is fully dissolved. Then the oil, the vinegar and the egg yolk are added. Subsequently, the preparations are homogenized with a high pressure homogenizer at 180 bar.

(5) Stability Test:

(6) Samples of preparations A, B and C were stored at 50° C. for 7 days in the heating cabinet to stimulate, to force and to investigate the oxidative and autoxidative processes, respectively.

(7) Analytical Testing:

(8) Analytical testing was carried out by means of Symstixx and GC-MS. A detailed description of the Symstixx® method is described in document EP 2233206 A1. The GC-MS measurement was carried out with a VF-Wax mx separating column (30 m×0.25 mm×0.25 mm) and a temperature program of 40° C.-3° C./min-230° C. During the measurements carried out, the substances hexanal, tr-2-octenal, 1,3-octenone, tr-2-heptenal, 2E,4Z-heptadienal, tr,tr-2,4-heptadienal, 2E-decenal, 2E,4E-decadienal, 2E,4E,7Z-decatrienal and 2E,4Z,7Z-undecatrienal that are typical for oxidative processes were determined. The determination of the amounts of these substances took place by means of the internal standard 2-nonanol. The determined ppm-amounts of these substances were summed up and the total amount of degradation substances was determined. The measured total amounts of sample A, sample B and sample C were compared to each other and the percentage ratio with regard to sample B was calculated.

(9) TABLE-US-00003 TABLE Results of the analytical measurements A B C ppm ppm ppm Total amount degradation substances 16512 5791 3984 percentage ratio in comparison with sample B 31

(10) The results show that sample A exhibits a considerably higher total amount of degradation substances than the other samples, wherein sample C with the mixture according to the invention displayed the lowest total amount of degradation substances. The measured total amount of degradation substances of sample C was 31% lower than the total amount of degradation substances of sample B with EDTA.

Example 3: Mayonnaise

(11) TABLE-US-00004 TABLE Mayonnaise Component wt.-% Sunflower oil 79.20 Water 7.40 Egg yolk, pasteurised 6.00 Vinegar 5% 4.00 Sugar 1.50 Table salt 1.00 Mixture M2 according to example 1 0.80 flavour 0.10 Sum 100.00

(12) For production of the mayonnaise, the water, vinegar, sugar, salt, mixture M2 and flavour are mixed first. Then one third of this mixture is mixed with the egg yolk. To this mixture, the oil is added with a weak jet, slowly in the beginning and faster towards the end, with simultaneous strong emulsification work. In between and mainly towards the end, the remaining amount of the mixture of water, vinegar, sugar, salt, mixture M2 and flavor are added between two portions of oil.

Example 4: Seasoning

(13) TABLE-US-00005 TABLE Cheese seasoning Component wt.-% Cheddar type cheese flavour SD 2.00 Citric acid 0.30 Lactic acid powder (loading 60% lactic acid) 1.00 Fat powder (Loading 77% fat) 9.75 Cheese powder mild cheddar type 11.75 Mixture M5 according to example 1 1.00 Yeast extract powder 5.00 Salt for seasonings 21.50 Onion powder 3.00 Cream powder (43% fat) 1.50 Silicon dioxide 0.70 Curcuma extract in vegetable oil 0.50 Vegetable oil triglycerides/coconut oil 0.30 Lactose/milk sugar 100 mesh vegetarian 20.00 Glucose/Dextrose (Corn IP) 8.00 Wheat powder vegetarian 13.70 Sum 100.00

(14) First the crystalline substances are added to the liquid components and mixed until everything is uniform. Then the remaining dry components and the concentrates are added and mixed until everything is homogeneous.

Example 5: Milk Fat Filling

(15) TABLE-US-00006 Component wt.-% Dextrose 10.00 Icing sugar 32.70 Vegetable fat 39.50 Skim milk powder 8.00 Whole milk powder 8.70 Mixture M4 according to example 1 0.80 Lecithin 0.30 Sum 100.00

(16) All components apart from half of the fat are mixed with each other. The refiner with three rollers should be used with a pressure setting of 60-75 bar for the input roller and of 110-125 bar for the output roller. Then the preparation is homogenized in the refiner. Subsequently, the remaining fat is introduced and mixed, respectively, with the aid of a mixer until the preparation is homogeneous.

Example 6: Biscuits

(17) TABLE-US-00007 TABLE Biscuits Component wt.-% 1 Wheat flour type 550 48.45 2 Vegetable fat Bavetin 28090 LT 19.50 3 Sugar 19.50 4 Eggs 5.00 5 Water 5.00 6 Skim milk powder 1.00 7 Mixture M1 according to example 1 1.00 8 Iodised salt 0.30 9 Ammonium bicarbonate 0.25 Sum 100.00

(18) First, component No. 9 is dissolved in water and an elastic dough is formed from all of the components. Then the dough is cooled for 30 minutes and then rolled out to 2.75 mm. Subsequently, the dough is baked at 190° C. heat from above and at 200° C. heat from below for 8 minutes.

Example 7: Cracker

(19) TABLE-US-00008 TABLE Cracker Component wt.-% Phase A 1 Wheat flour type 550 57.18 2 Wheat starch 6.00 3 Glucose syrup C Sweet M 01415 6.00 4 Vegetable fat Biscuitine 200 10.00 5 Iodised salt 1.00 6 Ammonium bicarbonate 1.40 7 Baking powder 0.30 8 Eggs 5.00 9 Water 13.00 10 Lecithin 0.10 11 Enzyme Sternzym BK Quick 0.02 Phase B 1 Vegetable fat or vegetable oil 98.90 2 Mixture M2 according to example 1 1.00 3 Aroma 0.10 Sum 100.00

(20) Phase A: First the ammonium bicarbonate is dissolved in water. Then the remaining components are mixed and then the mixture of water and ammonium bicarbonate is added. After the dough was kneaded in a Z-kneader for 6-8 minutes, it is brought to a temperature of 40° C. After a resting time of 30-60 minutes, the dough is rolled out to 1.75 mm and cut into 5×5 cm sized pieces. Then the pieces are baked at a heat from above of 300° C. and a heat from below of 260° C. for 3 minutes under steaming. After baking, the pieces are baked for a second time at a heat from above of 170° C. and a heat from below of 170° C. for 3 minutes and dried at 120° C. for 5 minutes. For production of phase B, the fat is melted, then the aroma and mixture M2 are added and homogenized. 8-10% of phase B are sprayed onto the dry crackers.

Example 8: Make-Up Remover

(21) TABLE-US-00009 TABLE Make-up remover Component INCI wt.-% Phase A Glycerin Glycerin 9.30 Surfhope ® C-1216 Sucrose Laurate 3.00 Surfhope ® C-1616 Sucrose Palmitate 3.00 Water Water (Aqua) 4.70 Phase B Neutral oil Caprylic/Capric Triglyceride 47.71 Dragoxat ® 89 Ethylhexyl Isononanoate 30.00 Ionol CP BHT 0.05 Phase C Symdiol ® 68 1,2-Hexanediol, Caprylyl Glycol 0.80 Phase D Perfume Parfum 0.15 Mixture M3 according 1.00 to example 1 Colour system I Colour 0.15 Colour system II Colour 0.14 Sum 100.00

(22) The production takes place in a Becomix.

(23) For production of phase A, the glycerin and Surfhope® C1216 are put into the Becomix and are stirred at −0.5 bar with 0.3 m/s, then they are homogenized with the aid of a Turrax at 3 m/s for 4 minutes. When the Surfhope® C1216 is completely dissolved, the Surfhope® C1616 is added, whereby the stirring is continued at 0.3 m/s. The subsequent homogenization takes place at 3 m/s for 4 minutes with the aid of a Turrax. Then water is added and again homogenized with the aid of a Turrax at 3 m/s for 6 minutes. This mixture is heated to 80° C. under stirring at 0.3 m/s, then brought to 50° C. and again homogenized with the aid of a Turrax with 3 m/s for 2 minutes. Subsequently, the temperature is raised to 80° C. and a pressure of −0.6 bar is adjusted.

(24) The production of phase B takes place at 80° C. At a temperature of 80° C., the components of phase B are very slowly and consecutively mixed with each other and then stirred at 0.5 m/s as well as homogenized with the aid of a Turrax at 3 m/s for 2 minutes. When one quarter of the oil has been put into the boiler, a homogenization step takes place with the aid of a Turrax at 5 m/s for 4 minutes. After half of the oil has been added, it is homogenized again with the aid of a Turrax at 5 m/s for 4 minutes and the stirring speed is raised to 0.8 m/s. When three quarters of the oil have been added, a homogenization step with the aid of a Turrax at 5 m/s for 4 minutes and an increase of the stirring speed to 1 m/s follows. Then the remaining amount of the oil is added and stirred at 1.2 m/s.

(25) After addition of phase C, the pressure is raised to −0.8 bar and it is homogenized with the aid of a Turrax at 5 m/s for 4 minutes. The preparation is cooled under stirring at 0.5 m/s to 25° C., whereby the stirring speed is reduced. Then phase D is added at 40° C.

(26) Colour system I: 0.1% solution in isopropyl palmitate of D&C Red No 17 C.I. 26100

(27) Colour system II: 0.1% solution in isopropyl palmitate of Phat Brown DC 8206: C.I. 47000, C.I. 26100, C.I. 60725

(28) The final preparation has a viscosity of 69280 cP.

Example 9: Lip Care Stick

(29) TABLE-US-00010 TABLE Lip care stick Component INCI wt.-% Medium mineral oil Paraffinium Liquidum 26.00 Permulgin 3220 Ozokerite 20.00 Paraffin 52-54 Paraffin 12.00 Neutral oil Caprylic/Capric Triglyceride 9.95 Mixture M1 according 0.05 to example 1 Prisorine Sqs 3758 Hydrogenated Polyisobutene 5.00 Cetiol 868 Ethylhexyl Stearate 5.00 Softisan 100 Hydrogenated Cocoglycerides 5.00 Xiameter ® PMX-0245 Cyclopentasiloxane 4.00 Cyclosiloxane Elfacos E 200 Methoxy PEG-22 and Dodecyl 4.00 Glycol Copolymer Permulgin 3430 Copernicia Cerifera (Carnauba) 2.00 Wax Ivarlan 3360 Glyceryl Lanolate 3.00 Super Hartolan Lanolin Alcohol 1.40 Cutina ® FS 45 Stearic acid, Palmitic acid 1.50 Jojoba oil 1.00 Titanium dioxide Titanium Dioxide 0.10 Perfume Perfume 0.01 Sum 100.00

(30) For production, all of the components in the order of the list without the perfume are melted and homogenized during warming to 70° C. At a temperature of 50° C., the perfume is added and homogenized.

Example 10: Night Cream

(31) TABLE-US-00011 TABLE Night cream Component INCI wt.-% Phase A Dragosan W/O P Sorbitan Isostearate, 5.00 Hydrogenated Castor oil, Beeswax (Cera Alba) Medium Mineral Oil Paraffinium Liquidum 15.00 Vaseline Petrolatum 4.50 Tece Ozokerit N 325/II Ozokerite 2.30 Dragoxat ® 89 Ethylhexyl Isononanoate 5.00 Phase B Water Water (Aqua) 64.10 Glycerin, 99,5 P. Glycerin 3.00 Magnesiumsulfate Magnesium Sulfate 0.70 Heptahydrate Preservative Complex Triethylene Glycol, Imidazolidinyl 0.30 (ND Liquid) Urea, Methylparaben, Propylparaben, Dehydroacetic acid Phase C Perfume Perfum 0.10 Mixture M3 according 0.50 to example 1 Sum 100.00

(32) For production, phase A and phase B are separately warmed to 80° C., respectively. Then phase B is added to phase A while using an Ultra-Turrax and emulsified. While stirring with a paddle agitator, this mixture is cooled and then emulsified again at 60° C. When the mixture has reached a temperature of about 35° C., phase C is added.

Example 11: Mayonnaise

(33) TABLE-US-00012 TABLE Mayonnaise Component wt.-% Sunflower oil 79.20 Water 8.10 Egg yolk, pasteurised 6.00 Vinegar 5% 4.00 Sugar 1.50 Table salt 1.00 Mixture M5 according to example 1 0.10 flavour 0.10 Sum 100.00

Example 12: M5 and Comparative Examples (Single Compounds) in Mayonnaise

(34) Mayonnaises were prepared according to Example 11, wherein Mixture M5 was added or replaced in the same amount by one of the following single substances:

(35) TABLE-US-00013 Category Hexanal in Fresh Stored %- Claim 1 Substance [ppb] [ppb] increase b) Benzoic acid 32.7 350.6 1072 c) 3-(3,4-dihydroxyphenyl)prop-2- 24.9 234.2 939 enoic acid a) Carvone 31.0 201.4 649 c) 3-[3-(3,4- 27.0 277.0 1025 dihydroxyphenyl)prop-2- enoyl]oxy-1,4,5-trihydroxy- cyclohexane-1-carboxylic acid e) Citric acid 23.2 151.4 653 f) Fructose 32.9 334.1 1016 b) Gallic acid 24.2 216.2 893 j) Gallocatechin 22.4 213.0 950 a) gamma-Terpinene 27.9 272.2 975 f) Glucose 33.5 289.9 864 a) Limonene 39.5 242.5 614 e) Malic acid 23.9 215.1 902 — Mixture M5 24.7 148.1 600 g) Propylene glycol 31.1 292.6 940 a) Pulegone 37.7 218.4 579 c) 3-(3,4-dihydroxyphenyl)-2-[3- 21.9 117.8 538 (3,4-dihydroxyphenyl)prop-2- enoyl]oxy-propionic acid f) Sucrose 34.8 292.6 842 b) 4-Hydroxy-3,5- 20.7 286.4 1381 dimethoxybenzoic acid d) Tartaric acid 23.2 201.4 866 h) Water 33.5 288.1 861

(36) Stability test and analytical testing were performed as described above. The amount of Hexanal was analyzed in fresh mayonnaises and in stored mayonnaises as described above.

(37) The experiments revealed surprising results. Supplementing mixture M5 with e.g. pure known antioxidants was expected to strongly inhibit the formation of Hexanal. However in the majority of experiments the single substances performed much worse than mixture M5. Only limonene, pulegone, and 3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propionic acid show a similar effect as the mixture M5. However, the pure substances were added in very high concentration for this kind of compounds, which would further make them unsuitable for use e.g. in food products. The off-taste that they would provide would be too high for such food products. E.g. limonene provides a very strong citrus flavour, and 3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propionic acid in pure form provides a very strong dry herbal, medicinal flavour; and pulegone provides a strong minty and camphor flavour. That makes these pure compounds not suitable to be used in a high concentration. The mixture of the invention solves this by using a combination of compounds, all in relatively low concentrations, and with a good antioxidative potential. Therewith the oxidation of the triglycerides can be effectively retarded, while still having a good-tasting product that does not have the off-taste associated with the same compounds in high concentrations.

(38) Furthermore, it was surprising that e.g. sugars seem to have an impact on the production of Hexanal.

(39) Moreover, even though terpenes are known for their stabilizing effect and for some an antioxidative effect is known, the use of terpenes as single substances replacing mixture M5 resulted in increased Hexanal formation.

Example 13: M5 and Comparative Examples (Mixtures) Used in Mayonnaise

(40) Mayonnaises were prepared according to Example 11, wherein Mixture M5 was added or replaced in the same amount by one of the following mixtures:

(41) TABLE-US-00014 Category in claim 1 Component M5 A B C D E F a) Thymol 0.0002 0.0000 0.0002 0.0002 0.0002 0.0002 0.0002 a) Limonene 0.1013 20.0000 0.1155 0.1013 0.1013 0.1013 0.1013 a) gamma-Terpinene 0.0909 0.0000 0.1036 0.0909 0.0900 0.0909 0.0909 a) Carvone 0.0082 0.0000 0.0094 0.0082 0.0082 0.0082 0.0082 a) Pulegone 0.0023 0.0000 0.0026 0.0023 0.0023 0.0023 0.0023 a) Carvacrol 0.0005 0.0000 0.0006 0.0005 0.0005 0.0005 0.0005 b) Gallic acid 0.5110 1.9000 0.5827 0.5110 0.5110 0.5110 0.5110 b) 4-Hydroxy-3,5- 0.8722 0.0000 0.9945 0.8722 0.8722 0.8722 0.8722 dimethoxybenzoic acid b) Benzoic acid 0.0083 0.0000 0.0095 0.0083 0.0083 0.0083 0.0083 i) Gallocatechin 0.3101 0.0000 0.3536 2.0000 0.3101 0.3101 0.3101 c) 3-(3,4- 0.0210 0.0000 0.0239 0.0210 0.0210 0.0210 0.0210 dihydroxyphenyl)prop- 2-enoic acid c) 3-(3,4- 1.4211 3.5000 1.6204 1.4211 1.4211 1.4211 1.4211 dihydroxyphenyl)-2- [3-(3,4- dihydroxyphenyl)prop- 2-enoyl]oxy-propionic acid c) 3-[3-(3,4- 0.0022 0.0022 0.0025 0.0022 0.0022 0.0022 0.0022 dihydroxyphenyl)prop- 2-enoyl]oxy-1,4,5- trihydroxy- cyclohexane-1- carboxylic acid d) Tartaric acid 7.7010 7.7010 8.7811 7.7010 7.7010 0.0000 7.7010 e) Citric acid 3.8329 3.8329 4.3705 3.8329 3.8329 0.0000 3.8329 e) Malic acid 3.9412 3.9412 4.4940 3.9412 3.9412 0.0000 3.9412 f) Glucose 5.5000 5.5000 0.0000 5.5000 5.5000 5.5000 0.0000 f) Fructose 5.7000 5.7000 0.0000 5.7000 5.7000 5.7000 35.0000 f) Sucrose 1.1000 1.8189 0.0000 1.1000 1.1000 1.1000 0.0000 h) Water 25.0000 15.0000 28.5063 25.0000 68.8765 25.0000 25.0000 g) Propylene glycol 43.8756 31.1038 50.0292 42.1857 0.0000 59.3507 21.1756 Sum 100.0000 100.0000 100.0000 100.0000 100.0000 100.0000 100.0000

(42) Stability test and analytical testing were performed as described above. The amount of Hexanal was analyzed in fresh mayonnaises and stored mayonnaises as described above and is shown in the following table.

(43) TABLE-US-00015 Hexanal Sample fresh Stored name [ppb] [ppb] %-increase M5 31.6 98.5 311.3 A 29.7 98.6 331.7 B 23.9 107.0 448.4 C 27.5 81.8 297.1 D 26.6 83.4 313.7 E 31.2 106.3 341.0 F 27.7 104.8 378.2

(44) Mixture M5 was selected exemplarily. Likewise the other mixtures according to the invention, see e.g. Example 1, could have been used.

(45) Mixture A comprises high amounts of Limonene (component a)), Gallic acid (component b)) and 3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propionic acid (component c)). These substances are known as antioxidant agents. Even though the amounts of these substances are strongly reduced in mixture M5 and even the sums of components a), b) or c) are each lower in mixture M5 than in mixture A, the mixture according to the invention performs slightly better than mixture A, as a lower increase of the amount of Hexanal is observed. Such a result was not expected. Furthermore, high amounts of Gallic acid, 3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propionic acid and particularly Limonene increase the risk of generating undesired off-tastes as described above.

(46) Mixture C comprises a strongly increased (almost 6-fold) amount of gallocatechin (component i)), which is known as a very potent antioxidant. However, mixture C and mixture M5 provide a comparable effect on the increase of Hexanal.

(47) Mixture M5 performs comparable or even better than other mixtures with highly increased amounts of antioxidants but otherwise the same/similar composition. Such an effect was not expected, especially when the total amounts of known antioxidants were compared.

(48) Compared to mixture D, mixture M5 comprises a solvent, Propylene glycol (component g)). Even though solvents may lead to an anti-synergistic effect of the respective components in a mixture, both mixtures achieve a comparable increase of the amount of Hexanal. Selecting Propylene glycol as a solvent resulted in no anti-synergistic effect. Furthermore, the solvent stabilizes the compounds in the mixture as well as in the emulsion system and mixture M5 comprising the solvent has a better solubility and can thus be added to the mayonnaise more easily.

(49) Furthermore, mixture E comprises no tartaric acid (component d)), citric acid and malic acid (both component e)). When these substances are not included in the mixture, comparing mixture E and mixture M5, the increase of Hexanal is stronger. Thus, tartaric acid, citric acid and malic acid seem to improve the antioxidative/stabilizing properties, when they are added in a mixture.

(50) Mixture B and mixture F do not comprise glucose and sucrose (both component f)). Further, mixture B does not comprise fructose (component f)), whereas mixture F contains a strongly increased amount of fructose compared to mixture M5. Both, mixture B and mixture F reveal a stronger increase of Hexanal production than mixture M5. Glucose, Fructose and Sucrose were not known to show an antioxidative effect. However, in the absence of these, or when fructose is strongly increased, less antioxidative effect is achieved and more Hexanal is produced, which was not expected. Furthermore, high amounts of sugars, as in mixture F, will negatively influence the viscosity of a mixture.

(51) The results of these experiments demonstrate that the components need to be present in mixtures according to the invention and that these components are required in distinct concentrations. Substances with known antioxidative effect are not necessarily providing increased antioxidative effect when they are simply added to such mixtures in higher concentration.