WO2020126605A1

WO2020126605A1 - Food containing a 4-(3-ethoxy-4-hydroxyphenyl) alkyl ketone compound and method for preserving same

Info

Publication number: WO2020126605A1
Application number: PCT/EP2019/084191
Authority: WO
Inventors: Sylvie Cupferman; Florence MENARD-SZCZEBARA
Original assignee: L'oreal
Priority date: 2018-12-20
Filing date: 2019-12-09
Publication date: 2020-06-25
Also published as: FR3090281A1; FR3090281B1

Abstract

The invention relates to a food comprising aketone compound of formula (I): wherein R2 represents a hydrogen atom or a methyl or ethyl radical and R3 represents a linear C1-C3 alkyl radical; and also a method for preserving food with said compound (I).

Description

Title: Food containing a 4-(3-ethoxy-4-hydroxyphenyl) alkyl ketone compound and method for preserving same

[0001 ] The subject of the present invention is a food containing a 4-(3-ethoxy-4- hydroxyphenyl) alkyl ketone compound and also a method for preserving a food.

Technical field

[0002] Food products have a short shelf life and are usually perishable after one to several weeks. It is therefore necessary to use preservatives to be able to preserve foodstuffs for a satisfactory period of time before consuming them.

[0003] The object of the present invention is to provide a novel food preservative having good efficacy on bacteria that are found specifically in foodstuffs.

[0004] The inventors have discovered, unexpectedly, that 4-(3-ethoxy-4- hydroxyphenyl)butan-2-one (ketone compound) has good antimicrobial activity on bacteria of interest in nutrition, in particular Salmonella enterica and Listeria monocytogenes bacteria. The results of example 1 described below show the antimicrobial activity obtained with the minimum inhibitory concentration (MIC) measurements. The ketone compound is effective for preserving food products with a short shelf life. As other bacteria of interest in nutrition, mention may be made of bacteria of the genus Campylobacter { for example Campylobacter jejuni), Vibrio (for example Vibrio parahaemolyticus), Yersinia (for example Yersinia enterolitica), Clostridium (for example Clostridium perfringens), Bacillus (for example Bacillus cereus). 4-(3-Ethoxy-4-hydroxyphenyl)butan-2-one also has antimicrobial activity on the molds (fungi) Aspergillus flavus, Aspergillus parasiticus, Aspergillus fumigatus, Aspergillus ochraceus, or those of the genus Penicillium sp. (for example Penicillium expansum, Penicillium verrucosum, Penicillium citrinum) or those of the genus Fusarium sp. (for example Fusarium verticillioides, Fusarium proliferatum, Fusarium graminearum, Fusarium culmorum, Fusarium sporotrichioides). [0005] 4-(3-Ethoxy-4-hydroxyphenyl)butan-2-one (ketone compound) is described in WO 2011/039445 as a preservative of cosmetic compositions for protecting the compositions against microbial contamination. Cosmetic products, unlike food products, need effective antimicrobial protection over a long period of several months.

[0006] The article "Odeur et constitution sur des homologues et analogues de la p-hydroxyphenyl-1-butanone-3” [Odor and constitution on homologs and analogs of p-hydroxyphenyl-1 -butanone-3"] M. Winter; Helvetica Chimica Acta, volume XLIV, fasciculus VII (1961 ) No. 262 p 2110-2121 describes the organoleptic properties of 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (compound XVIII) which are evaluated by tasting in a syrup of acidulous sugar. This document does not describe the antimicrobial activity of said ketone compound on the bacteria mentioned above.

[0007] More specifically, a subject of the invention is a food comprising at least one 4-(3-ethoxy-4-hydroxyphenyl) alkyl ketone compound (I) as described below.

[0008] Another subject of the invention is a method of preserving a food, characterized in that it consists in incorporating into said food at least one ketone compound (I) described above. In particular, the method allows preservation of food against Salmonella enterica and/or Listeria monocytogenes, and also against the bacteria and fungi mentioned above.

[0009] For the purposes of the present invention, and unless otherwise indicated:

an " organic or inorganic acid salt' is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(0)₂0H such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(0)₂0H such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-0-S(0)0H such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH₃C(0)OH; xiv) triflic acid CF3SO3H; and xv) tetrafluoroboric acid HBF4;

an“organic or inorganic base salts " means salts of bases or alkaline agents as defined below, such as alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, or alkaline earth metal calcium hydroxide, ammonia, amines or alkanolamines.

an "alkyl radical' is a linear or branched hydrocarbonyl chain saturated;

moreover, the addition salts that may be used in the context of the invention with The 4-(3-ethoxy-4-hydroxyphenyl) alkyl ketone are especially chosen from addition salts with a cosmetically acceptable base such as basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines; preferably 4-(3-ethoxy-4- hydroxyphenyl) alkyl ketone can be in a salt form such as formula (G):

Formula (G) in which M⁺ represents a cationic counter ion especially an alkali metal such as sodium or potassium, or alkaline earth metal such as calcium or ammonium. the term " at least one " is equivalent to the term "one or more".

[0010] The 4-(3-ethoxy-4-hydroxyphenyl) alkyl ketone compound of formula (I) is:

(I) and salts thereof with an organic or inorganic acid or base, and solvates thereof such as the hydrates ;

Formula (I) wherein:

R2 represents a hydrogen atom or a methyl or ethyl radical and R3 represents a linear C1-C3 alkyl radical.

[001 1 ] Mention may particularly be made of the following compounds of formula

(I):

[0012] Use is preferably made of 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one, which is a compound of formula:

and salts thereof with an organic or inorganic acid or base, and solvates thereof such as the hydrates.

[0013] The food may comprise at least one foodstuff chosen from meats, fish, shellfish, vegetables, fruit, cereals, eggs, butter, milk, vinegar.

[0014] The food may also comprise at least one food additive chosen from water, vegetable oils, sugars, salt, spices, emulsifiers, alcohols, thickeners, honey.

[0015] The 4-(3-ethoxy-4-hydroxyphenyl) alkyl ketone compound (I) may be present in the food according to the invention in a content ranging from 0.5% to 5% by weight, relative to the total weight of the food, preferably ranging from 0.55% to 3% by weight, preferentially ranging from 0.6 to 2% by weight, more preferentially ranging from 0.6 to 1.5% by weight, and better still ranging from 0.6 to 1 % by weight.

[0016] Preferably the ketone compound (I) is predissolved in a food-grade solvent before being added to the food. As solvent, use may be made of ethanol, propylene glycol, isopropyl alcohol and mixtures thereof, optionally combined with water.

[0017] The food according to the invention may for example be in the form of bread, cake, sauce, candy, a cooked dish, confectionery, jelly, dessert, nougat, drinks, juice, syrup, wine, beer, ravioli, mousse, compote, mayonnaise, mustard, vinaigrette, chips, sausage, gnocchi, polenta, pancakes, pates, cheeses, flour, deli meats, soup.

[0018] The invention is illustrated in more detail in the following examples. The amounts of the ingredients are expressed as weight percentages.

[0019] Examples

[0020] Example 1 : Measurement of antimicrobial activity in MIC

4-(3-Ethoxy-4-hydroxyphenyl)butan-2-one (termed substance A) was tested on the following strains: Salmonella enterica and Listeria monocytogenes.

[0021 ] Materials and Methods

[0022] Principle

[0023] The product at a concentration double the concentration to be tested is brought into contact with the nutrient broth at double concentration previously contaminated with the test strain so as to have a final titer of between 1 and 3.10⁵ cfu/ml. After incubation of the broth for 24 hours at 36°C, a microorganism count is carried out according to a surface method and compared to the starting inoculum to define the concentration from which the inhibitory effect occurs.

[0024] The minimum inhibitory concentration is defined as the first concentration which makes it possible to return to the starting inoculum.

[0025] Compound tested:

[0026] 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (termed compound A) [0027] Operating conditions

Counting method: surface counting

Preparation of the stock solution: a stock solution of compound A at 10% (w/v) was prepared in 1 %o agar from a solid fraction of the compound previously maintained at 55°C for 1 hour in order to liquefy it.

Concentrations of the compound tested: 0.01 %; 0.05%; 0, 1 %; 0.5% and 1 % (w/v). Diluent for preparation of the dilutions: 1 %o agar.

Difco nutritive broth

Appearance of the product in the broth: clear.

Test strains: Salmonella enterica CIP 58 58 and Listeria monocytogenes CIP 103573

Nutritive broth incubation time and temperature: 24 h at 36°C ± 1 °C.

Count agar: Tryptic Soja Agar (TSA)

TSA incubation time and temperature: 3 days / 36°C ± 1 °C.

Positive control (presence of the test strain and absence of the compound)

[0028] Results

The results obtained are shown in table 1.

Salmonella enterica

[Table 1 ]

Compound A has an inhibitory activity with respect to Salmonella enterica for a concentration greater than 0.5% by weight. Listeria monocytogenes

[Table 2]

Compound A has an inhibitory activity with respect to Listeria monocytogenes for a concentration greater than 1 % by weight.

[0029] Example 2:

A vinaigrette having the following composition (% by weight) is prepared:

Sunflower oil 45%

Oxyethylenated sorbitan monostearate (20 OE)

(Tween 60 from Croda) 0.3%

Potato starch 1 %

Wine vinegar 10%

4-(3-Ethoxy-4-hydroxyphenyl)butan-2-one 1 %

Propylene glycol 2%

Water qs 100%

[0030] Example 3:

A mayonnaise having the following composition (% by weight) is prepared: Sunflower oil 17%

Vinegar 7%

Egg 7%

Salt 3% Agar-agar 2%

Propylene glycol 2%

4-(3-Ethoxy-4-hydroxyphenyl)butan-2-one 1 %

Water qs 100%

Claims

[Claim 1 ] A food comprising one or more ketone compounds of formula (I):

(I) and salts thereof with an organic or inorganic acid or base, and solvates thereof such as the hydrates;

wherein R2 represents a hydrogen atom or a methyl or ethyl radical and R3 represents a linear C1-C3 alkyl radical ; and

one or more foodstuffs selected from meats, fish, shellfish, vegetables, fruit, cereals, eggs, butter, milk, and vinegar.

[Claim 2] The food as claimed in the preceding claim, characterized in that the compound (I) is chosen from:

[Claim 3] The food as claimed in either of the preceding claims, characterized in that the compound (I) is 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one.

[Claim 4] The food as claimed in one of the preceding claims, characterized in that the compound (I) is present in a content ranging from 0.5% to 5% by weight, relative to the total weight of the food, preferably ranging from 0.55% to 3% by weight, preferentially ranging from 0.6 to 2% by weight, more preferentially from 0.6 to 1.5% by weight, and better still ranging from 0.6 to 1 % by weight .

[Claim 5] The food as claimed in one of the preceding claims, characterized in that it comprises one or more food additives selected from water, vegetable oils, sugars, salt, spices, emulsifiers, thickeners, alcohols, and honey.

[Claim 6] A method for preserving a food, characterized in that it consists in incorporating into said food one or more compounds of formula (I):

wherein R2 represents a hydrogen atom or a methyl or ethyl radical and R3 represents a linear C1-C3 alkyl radical, the food comprising one or more foodstuffs chosen from meats, fish, shellfish, vegetables, fruit, cereals, eggs, butter, milk, vinegar.

[Claim 7] The method as claimed in the preceding claim, characterized in that the compound (I) is chosen from:

[Claim 8] The method as claimed in either of claims 6 and 7, characterized in that the compound (I) is 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and salts thereof with an organic or inorganic acid or base, and solvates thereof such as the hydrates.

[Claim 9] The method as claimed in one of claims 6 to 9, characterized in that the compound (I) is present in the food in a content ranging from 0.5% to 5% by weight, relative to the total weight of the food, preferably ranging from 0.55% to 3% by weight, preferentially ranging from 0.6 to 2% by weight, more preferentially from 0.6 to 1.5% by weight, and better still ranging from 0.6 to 1 % by weight.

[Claim 10] The method as claimed in one of claims 6 to 9, characterized in that the food comprises one or more food additives selected from water, vegetable oils, sugars, salt, spices, emulsifiers, thickeners, alcohols, and honey.

[Claim 11 ] The method as claimed in one of claims 6 to 10, for preservation of food against Salmonella enterica and/or Listeria monocytogenes .

[Claim 12] Use of one or more compounds of formula (I) and salts thereof with an organic or inorganic acid or base, and solvates thereof such as the hydrates as defined in any one of the claims 1 to 5, for preservation of food especially against Salmonella enterica and/or Listeria monocytogenes .

[Claim 13] Use as claimed in the preceding claim, characterized in that the compound (I) is present in the food in a content ranging from 0.5% to 5% by weight, relative to the total weight of the food, preferably ranging from 0.55% to 3% by weight, preferentially ranging from 0.6 to 2% by weight, more preferentially from 0.6 to 1.5% by weight, and better still ranging from 0.6 to 1 % by weight.

[Claim 14] Use as claimed in one of claims 12 or 13, characterized in that the food comprises one or more food additives selected from water, vegetable oils, sugars, salt, spices, emulsifiers, thickeners, alcohols, and honey.