WO2008132127A1 - Method for obtaining fish oils stabilised by plants and having a satisfactory taste acceptability, and corresponding oily extracts - Google Patents

Abstract

The invention relates to a method for obtaining fish oils stabilised by plants and having a satisfactory taste acceptability, characterised in that it comprises the steps of macerating, away from air and light under an inert gas atmosphere or partial vacuum, a plant selected from the group comprising thyme, logwood, cumin, caraway seed, oregano, nutmeg, mace, cardamom, cinnamon or a vegetable composition constituting of curry powder in a food fish oil rich in polyunsaturated fatty acids, in particular unsaturated omega-3 fatty acids, for a duration of at least 20 days at a temperature of 20°C +/-5°C; after decanting the vegetable material, recovering, clarifying and conditioning the supernatant away from air, the method being implemented without volatile solvents and without heat supply.

Description

 Process for obtaining vegetable-stabilized fish oils with satisfactory taste acceptability and corresponding oily extracts STATE OF THE ART Animal oils and in particular fish oils have been the subject of intensive research and applications for decades because of their interest as food supplements that could bring a benefit to human and animal health. These properties have been summarized in particular by LMc MURRAY-International Food Ingredients-2007-2-23 / 26 The consumption of these products comes up against four main obstacles: - the need for a daily intake of around 1 g / day of an oil containing at least 18% EPA (eicosapentaenoic acid) and 12% DHA (docosahexaenoic acid) (Report of the AFS SA- "Fatty acids of the omega-3 family and cardiovascular system, nutritional interest and allegations "-June 2003 -). These unsaturated fatty acids, commonly known as "omega-3s", are found mainly in oils extracted from certain fish (notably sardines, herring, cod, skate, shark), in the form of glycerides and sometimes reinforced by the addition of esters of these same Fatty acids ;

- the adverse taste characteristics: taste and smell of rancid and persistent and perceptible fish during their digestion;

- the chemical instability (oxidability) of the unsaturated compounds present in these oils which produces aldehyde and acidic substances responsible for unpleasant olfactory and taste notes, perceptible in trace amounts, and moreover associated with a toxicological risk.

This instability increases by the use of esters of these fatty acids. LIE KEN JIE and AL-

NATURAL PRODUCTS REPORT- 1998- "Fatty Acids, fatty acids analogues and their derivatives pp. 607-615); - the need to avoid any cooking process which may produce toxic degradation products by pyrolysis and oxidation.

Oily bodies: glycerides (more or less complete esters of glycerol and saturated and unsaturated fatty acids); the fatty acids resulting from the cleavage of these glycerides by saponification or enzymatic lipolysis; their various esters obtained chemically or biochemically (esterases) are poor solvents, not very powerful in terms of capacity and extraction and solubilization, and moreover unstable.

Pharmacopoeias have in the past described oily solutes such as "camphor oil" for which the (vegetable) oil serves as an excipient, vehicle; which leads to the classification of oily products as pharmaceutical excipients (A. DENOEL - "Galenic Pharmacy Course - 1965 - Volume II - p263 - University Presses of Liège). An example is the so-called "balm tranquil" also called "Oil of compound henbane", pharmaceutical preparation, now obsolete; which uses a vegetable oil to convey an alcoholic extract of medicinal active ingredients; this is indeed an excipient.

There are currently on the market oily extracts of Garlic, Mistletoe, Hawthorn for therapeutic use, the last two components also from the Pharmaceutical Monopoly (The raw material is listed in the French Pharmacopoeia).

On the other hand, fish oils belong to the food field; more precisely that of nutritional supplements known as nutraceuticals.

In the culinary field vegetable oils are used to obtain pimento macerations for pizzas, or even basil for strictly aromatic purposes, but fish oils are not used because of their repellent taste.

Compared to the usual extraction solvents (which can be used under various conditions: maceration in the environment, reflux extraction, percolation, leaching and which are mainly alcohols, volatile solvents such as acetone, hexane; or else polyols (propylene glycol for example) and which appear on a European official positive list of solvents used for obtaining extracts for human or animal food use); fish oils are not listed and have the following defects: - high cost;

a reduced solvent power and difficult to manage;

the impossibility of being able to concentrate the extracts obtained and to recycle all or part of the oil used as a solvent;

an instability directly linked to the presence of unsaturated compounds. Fish oils, and more generally unsaturated oils, have not been used heretofore as extraction solvents by any industry; especially in the Food and Pharmaceutical industry for the reasons already mentioned and in particular:

- repulsive taste and smell;

- instability, accompanied by the risk of production of toxic substances. The flavoring materials and also the antioxidants are never extracted using fish oils and more generally unsaturated oils.

By fish oils is meant any oily extract product extracted from marine organisms composed mainly of saturated, unsaturated and polyunsaturated fatty acid glycerides and any composition comprising a marine oil associated with saturated fatty acid esters, unsaturated to polyunsaturates. There is indeed a whole range of marine oils: - the most classic, especially from sardine, herring, cod ideally include:

18% eicosapentaenoic acid (EPA) 12% docosahexaenoic acid (DHA) (% expressed, by convention, relative to the total fatty acids present in the oil).

- "reconstituted" oils derived from the assembly of various oils of various fish

oils reinforced by the addition of fatty acid esters derived from the extraction, saponification, extraction then semisynthesis by chemical or enzymatic means; this route makes it possible to obtain extremely high levels of unsaturated fatty acid esters of interest (in particular EPA and DHA).

Faced with the difficulties mentioned above, producers and formulators have hitherto resorted to the following palliatives: - the use of antioxidants, - the protection against oxygen - the addition of flavoring substances and, or masks (The US Patent

6,576,253 claims the association of malto-dextrins and natural flavors).

These palliatives are insufficient and do not allow long-term preservation and satisfactory taste acceptability, with an acceptable additional cost.

All of these unresolved issues so far have been exposed in AROMES INGREDIENTS ADDITIVES- 2007-68-45 / 51

It will be noted that:

the use of antioxidants is limited qualitatively and quantitatively by European and national regulations concerning the use of food additives;

these antioxidants have an extremely limited antioxidant capacity and can not by themselves stabilize a raw material and a fortiori a formulation;

- empirically, formulators have observed synergies with combinations of antioxidants, without an understanding and a theory of this effect being possible; even more antioxidants or their own oxidation products can be frequently pro-oxidants and accelerate the degradation process; the protection against oxygen is of relative effectiveness: by inerting, with nitrogen for example; or partial vacuum, for industrial storage; or by encapsulation (soft capsules or microcapsules), which is achievable with high costs and inevitable dilution of the oil which interferes with the ease of ingestion.

The encapsulation makes it possible to obtain storage durations of three years, by the "oxygen barrier" effect implemented and by the coating of the product whatever its sound. state; This is the reason why encapsulated products are not easily digested because of possible fishiness;

- the addition of flavoring or masking substances is generally a "plating", or a juxtaposition of taste and olfactory notes that adds more or less happily to oxidized notes and fish, and is unable to inhibit their formation. Generally the duration of perception of taste sensations of the aromatization is less than that of the fish and oxidized notes which are extremely persistent;

- considered individually or in synergy these processes and strategies bring considerable additional costs, without any significant benefit. The general strategy is systematically based on the use of additives: flavorings, masking agents, anti-oxidants, encapsulation agents; without exploiting the functionalities of the marine oils to be stabilized (their possible extractive capacity), nor knowledge of the compatibility of said additives with the natural components of these oils. The control of the taste acceptability of these assemblages remains problematic and constitutes a major obstacle for the user to observe the consumption of the recommended doses. (US Patent 4,853,247)

DESCRIPTION OF THE INVENTION

The object of the invention is to provide a method for obtaining stabilized fish oils, that is to say not oxidizing or very little in time and having a good taste acceptability, it is that is to say, having no smell or after-taste of oxidized fish.

Unexpectedly, we have observed that fish oils have a sufficient and specific solvent power towards antioxidants naturally present in certain spices, and certain condiments and flavorings used in culinary arts or in industry.

Aromatic in addition to their solvent power of flavoring substances.

These properties allow the simultaneous extraction, simultaneously, antioxidants and aromatic substances and flavors of various plants and plant parts commonly used as condiments, spices or herbs. In general, plants and their fractions (seeds, leaves, roots, fruits) have been widely studied for their olfactory and taste properties, based on the results of the most efficient methods of analysis (gas chromatography). (CPG);

GPC coupled to mass spectrometry or GPC-olfactometry); this allowed us to identify only the volatile components of the essential oils they contain. On the other hand, their composition of natural antioxidants: unsaturated compounds and polyphenols remains poorly known.

The skilled person also knows, empirically:

that the natural antioxidants in a complex mixture are generally more effective than the chemical substances obtained from their purified extracts (Rosemary, Oregano and their respective extracts are typical examples thereof);

- that the protective effect of any antioxidants is limited and requires conservation away from the air;

(Hamilton et al., J. Am. Chem. Soc. 1998-75-7-813 / 822) (M. OZCAN - Journal of Medicinal Food-2003-6-3-267 / 270).

As a result, we had to carry out a comparative study of the effectiveness of various spices, herbs and condiments.

The validation of the effect of this or that antioxidant is generally obtained from the measurement of global chemical tracers (peroxides index, thiobarbituric acid test, iodine number, fatty acid determination, search for compounds oxidation tracers, (for example limonene oxide in the case of limonene), another approach is to voluntarily oxidize the presumed stabilized preparation and to compare its relative stability, in fact its degradation profile, with an untreated control: Rancimat® test for example.

All these tests are either fragmentary (measurement of tracers more or less arbitrary) or excessively aggressive (when it comes to disassemble a global protective power against oxidation), and, therefore, hardly predictive of conservation of the sample considered.

In the case of fish oils, infrequent traces of oxidation compounds are sensory detectable with a sensitivity much higher than that of all conventional methods; this results in an extreme severity of the test due to the exploitation of sensory results in all or nothing: the appearance of an "off-note" or parasitic note, "fish" or "rancid" leads us to reject the formulation considered. (VENKATESHWARLU and Al-J.Agric.Food.Chem-2004-52 (2) -311/317)

These oxidation products are often accompanied by traces of aliphatic amines (triethylamine, in particular) resulting from the partial degradation of the fish or organs (livers) of the fish used.

These olfactory and taste tests allow very quickly (within a maximum of three weeks) to notice the onset of degradation: this is a considerable advantage over chemical methods. (HAMILTON RJ and Al- J.Am Oil.Chem Soc- 1998-75-N ° 7-pp813 / 822) The application of the extractive process of the present invention to various extracts has shown the following effects:

1 °) There is a great variability of the anti-oxidant stabilizing potential of the various oily extracts of the plants studied;

(2) For the same plant species, the effects obtained may vary significantly from one batch to another, particularly as a function of the duration and storage conditions of the plant material used; These two characteristics are known to those skilled in the art.

3 °) Compared with the antioxidants most commonly used or recognized as the most effective:

BHA (butylhydroxyanisole) BHT (butylhydroxyto luene)

Ascorbyl Palmitate Natural Tocopherols (extract)

Association of ascorbyl palmitate and tocopherols,

In the context of the present invention, it is found, for certain vegetable extracts, by fish oils, significantly higher protection against oxidation performances which can be qualified by:

-Improving the shelf life

the improved storage stability in opened flasks, that is to say having a head space, therefore a significant volume of oxygen. This constitutes a model for studying oxidative degradation, representative of conditions of use of the oil without particular precautions.

To date, these facts have not been reported and can not be reported to the current state of knowledge on the composition of the plants used nor to any comparable extractive preparation.

4 °) If one refers to the recognized natural antioxidants plant and listed below, it is noted that their liposolubility is often, theoretically, favorable to extraction by an oil. Under these conditions, a relatively uniform performance of protection against oxidation should be observed between the various plant extracts studied. This is absolutely not the case and this observation is opposed to any generalization.

This means that, unexpectedly; in certain plants or parts of plants (leaves, seeds, fruits, roots, bark):

or many strong antioxidant compounds, not yet described, naturally present, are extractable by fish oils. or the anti-oxidant compounds or part of these compounds exist in the plant in a physical state or in particular chemical combinations and not described to date, which allow their extraction by fish oils under the conditions of the present invention.

Table of main natural antioxidants (**)

Solubility in oils ... in organic solvents (***) Vitamin C Nulle Nulle

Vitamin E Good Good

Folates Nulle Nulle

Carotenes Moderate Good

Polyphenols (*) Good Polyphénols Salifieess Nulle Nulle

Flavonoids Medium Average

Lycopene Good Low

Coenzyme QlO Good Good

Documentary origins: (*) - P.Brat- CIRAD-Montpellier

(**) - ANTIOXIDANTS IN FOOD - K.Pelli-M.Lyly Flair Flow Europe 4- INRA (**) - V.NEDYALKA and AL-European J.of lipid science and Technology-2001-103-11 -752 / 767)

(***) Merck Index

Rosemary extracts are the reference in terms of natural phenolic antioxidants.

Given the weakly acidic properties of phenols, various strategies exist for the extraction: solvent extraction: methanol, acetone, generally hot, followed by evaporation and the dissolution of the extract in a vegetable oil (E STEF ANOVITS and AL- Acta Biologica SZEGEDIENSIS-2003-47 (1-4) 111/113)

(D.BANDONIENE and AL-NAHRUNG-2001-April-45 (2) - 105/108) the use of the solubility in water of salts obtained by the action of a base on phenols (US Pat. No. 4,012,531), or that of acidified extracts in organic solvents (US Pat. No. 4,354,035)

the use of fluorinated solvents (US Pat. No. 6,855,349); the use of gases in the supercritical state, which under these conditions behave substantially like organic solvents.

In no case is it possible to use a vegetable or animal oil as extractant.

5 °) The choice of spices and aromatics studied took into account the acceptability of the flavor and the smell of the extracts obtained.

Unexpectedly, some of these oily extracts are not only able to extract complex natural antioxidant substances, but also taste and olfactory flavoring materials, not only acceptable but also extremely rich, fine and aromatic complex and qualitatively distinct from the usual aromatic extracts (essential oils, oleoresins, various extracts).

This can be explained by the absence of use of volatile solvents, the absence of the use of concentration; the absence of use of heat at any stage of the process, which minimizes the risk of degradation, but also the fact that many flavoring substances exist in the plant in a physical state or in chemical combinations (glycosides for example) that escape the usual extraction techniques. (Research theme of CIRAD-Montpellier)

This means that the hypothetical substitution of extracts obtained with the aid of fish oils, a mixture of essential oils and or oleoresins, or even extracts obtained by other means, would neither make it possible to restore completely the flavor and smell, nor the antioxidant power of extracts obtained with fish oils.

It is important to emphasize that a conventional aromatisation-stabilization such as that mentioned in the preceding paragraph is in no way interchangeable or substantially equivalent, in comparison with the corresponding plant extract obtained under the conditions of the invention. with fish oils.

The process which is the subject of this document could be compared with the classical technique of "enfleurage" of extracts for perfumes; except that the extractive materials used by the latter process are significantly different, separated "infine" extracted materials and that the present process is not the perfumery and raw materials for this use. Moreover, the extraction agents used in enfleurage are obligatorily neutral on the sensory plane.

6 °) oily extracts animal, aromatic obtained, also have excellent preservation qualities; unexpectedly, stabilized unsaturated oils, compatible and stable aromatic extracts (not yet described) and taste-tolerant formulations having an undisputed foodstuff status are thus obtained.

This radically differentiates the extracts obtained, conventional assemblies obtained by addition of flavors and stabilizers.

7 °) Under the preceding reservations, it goes without saying that the transposition of the process to other unsaturated compounds, such as the terpene compounds which are part of the composition of many raw materials and aromatic extracts is practicable.

We thus arrive at a new concept of "building-block" or "premix" which can be of great use, under condition of gustative and olfactory compatibility in the final product between the extractive material (a terpene for example) and the flavoring and stabilizing agent extracted from a plant by this terpene.

By way of example, an extract using a vegetable oil can be designed as an extraction solvent for sage, rosemary or clove, etc .; associated with an essential oil of sage or rosemary, or clove ... having improved preservation without having to resort to the addition of a conventional antioxidant.

8 °) Unexpectedly, we observe for certain extracts the obtaining of unpublished aromatic notes which result either from the juxtaposition of the aromatic notes specific to the fish oil used with those of the condiment, flavoring or flavoring. spice used; or the extraction of original flavoring materials. There is here a source of potential aromatic innovations which further has the advantage of simultaneously containing antioxidant substances useful not only for the stabilization of the oil used, but also the stabilization of the extracted flavoring substances.

9 °) Although the oils are considered as poor solvents, and that the vegetal substrate to be extracted is whole or contused (seed-leaves), one finds unexpectedly, that the extraction of the aromatics and antioxidants substances performed in a relatively short time and comparable to the usual maceration times in solvents such as that alcohol, glycerol, propylene glycol or even liquid polyoxyethylene glycols; the latter being used for the cosmetic and pharmaceutical industry.

Those skilled in the art know that the extraction is limited by the diffusion rate of the chemical species of interest (aromas and antioxidants); it is therefore unnecessary to carry out prolonged and intense agitation of the mixture during maceration.

As a result, the diffusion of the chemical species of interest should be extremely slow. Unexpectedly, the extractive equilibrium is reached in a few weeks, which suggests that the substances of interest are in a physical form or an unknown chemical structure, but conducive to and favorable to the process described in the present application.

10 °) The extraction is carried out moreover at ambient temperature (20 ⁰ C +/- 5 ° C) which is the guarantor of a protection of the substances of interest: aromas and anti-oxidizing substances, and differentiates the claimed method of the usual techniques for extracting antioxidant compounds in particular.

11 °) Finally, the physical state of the plants (seeds, dried leaves) contamined or not does not influence significantly on the speed of the extractive process. These last two observations were a priori unpredictable given the state of knowledge on the properties of fish oils.

12 °) Compared to antioxidant extracts of natural origin, the "equivalent dose - plant" is of the same order of magnitude. Indeed, if we consider that a maximum content of 10% weight / weight in plant relative to the oil is sufficient to achieve the dual objective of aromatization and stabilization, it is virtually the same for plant extracts usual antioxidants obtained by drastic techniques (solvents, high extraction temperatures and concentration); thus, for the anti-oxidant extract of Rosemary which refers to: 1.000 g of rosemary makes it possible to obtain approximately 0.13 kg of crude antioxidant extract, the recommended use dose of which is at least 200 mg / kg. even 500 mg / kg of finished product, ie 5% of plant equivalent.

Insofar as the claimed process necessarily leads to a state of equilibrium, compared to a conventional extraction process which aims at the exhaustion of the substrate at extract, it can be considered that economically and technically the processes are comparable; the situation is quite different in terms of quality: because of the non-aggressive conditions of the claimed process and the nature of the active chemical species (antioxidants) extracted, extraction with fish oils constitutes an acceptable alternative.

The application examples implemented:

on the one hand fish oils (Shark or Ray liver oils) rich in omega-3 unsaturated fatty acids ("omega-3") and alkyl-glycerols, called "oil B" in the examples and showing the following characteristics:

Free fatty acids: less than 0.5% Iodine content: minimum 80g / p 100g Minimum saponification index 120mg KOH / Ig Unsaponifiable: minimum 20%

Minimum omega-3 content: 40% Oleic acid content: 20%

on the other hand fish oils (Sardine, Cod, Herring) salmon, rich in Omega-3 named "oil A" in the examples and having the following characteristics: Minimum content: EPA: 10% DHA: 20%

GENERAL DESCRIPTION OF THE PROCESS:

The fish oil resulting from the extraction and purification process is supplemented with plant material to be extracted beforehand if necessary. Experience shows that a maximum content of 10% by weight per weight of the plant relative to the oil, is generally sufficient. Indeed higher concentrations pose problems of dispersion of the plant to be extracted and may lead in some cases to a saturation of the extractant (the oil used) in substances of interest (aromas, antioxidants)

The vegetable mixture and fish oil are kept away from air and light, under inert gas (nitrogen) or under partial vacuum; at room temperature (20 ⁰ C +/- 5 ° C) for at least 20 days. A longer period does not present any risk or noticeable benefit. Every five days, by appropriate means, and without introducing air, the maceration is resuspended to facilitate the action of the extractant.

It is noted that the decantation of the plant material is relatively fast and that all the extracts are easily clarified, even in the case of pulverulent raw materials. At the end of extraction, after decantation of the supernatant, protected from the air; the solid residue can be pressed and its product, clarified, added to the supernatant.

The supernatant is clarified in the absence of air; and packaged in inert, watertight, opaque and completely filled or inert with nitrogen, if filling can not be complete.

This process also makes it easy to standardize the overall protective and flavoring power by assembling extracts of different potency in both antioxidants and aromatic materials.

Preferably, the extract, after control, can be directly divided into unit doses: opaque soft sachets, sealed, sealed or single-dose vials.

The final control makes it possible to ascertain the physico-chemical and microbiological characteristics of the extract obtained; it is accompanied by the determination of chemical oxidation tracers and taste comparison with reference sample extracts, the latter test is decisive.

This process has the advantage of being able to integrate easily with the normal production sequence of a fish oil; it requires, in addition to the control of the quality of the oils used, that of the plant materials used and in particular:

the shelf life between harvest and use, traceability, the residual moisture content of the plants or parts of plants used; microbiological quality (search for spores of anaerobic microorganisms in particular); -the taste quality.

These controls are familiar to those skilled in the art who use condiments, spices or aromatics.

As the oily medium is a priori favorable to the development of anaerobic microorganisms, we have also experimented with fresh, undried plants (Thyme, Savory, Sage, Shallot, Onion).

In these extreme conditions and favorable to the development of such contaminations; no revivification of spores was observed and in general no development of bacteria, yeasts or molds was found, but all the extracts made was less protective of oxidation and especially less powerful extracts obtained from dry plants or their dry fractions (equivalent dry weight). The use of dried raw materials minimizes the risk of contaminations, reduces the risk of uncontrollable enzymatic reactions (oxidases, peroxidases, esterases) and remains compatible with industrial management of the extractive process.

EXAMPLES ACCORDING TO THE INVENTION AND COMPARATIVE EXAMPLES

Two types of fish oils have been systematically used comparatively: An oil rich in omega-3 polyunsaturated fatty acids, especially EPA and DHA: called "A" oil.

An oil rich in polyunsaturated fatty acids of the Omega 3 type, in particular EPA and DHA, and rich in alkylglycerols: called "B" oil.

For each type of oil, two witnesses were kept:

one free of antioxidant (s) corresponding to the original raw material used: "control oil 1";

- the second supplemented with BHT, considered as the reference antioxidant and in the limited scope of modeling: "Control oil 2".

Indeed, BHA and BHT are chemically defined antioxidants, powerful, but suspect in terms of their use in food.

The comparative sensory analysis was carried out after 3 weeks, then 6 months of storage at room temperature (for the only tests deemed satisfactory after 3 weeks of storage), in the dark, in a sealed glass bottle having a headspace of 50%. This large, air-rich head space is a conservation study model, with no special precautions. After three weeks of storage, the two oils - Control 1 and 2 presented rancid taste and olfactory notes.

EXAMPLE 1- THYM EXTRACTS (Thymus vulgaris)

1-1-dried thyme, leaves, origin Morocco, initial storage 24 months before use After 3 weeks:

Extracts A and B, greenish, limpid, have a smell of linseed oil. Gustative a fish note in "attack" at the beginning remains perceptible then disappears in favor of the note "thyme" which persists durably, without aftertaste of fish. Under these conditions this test was not continued, although obtaining an "anchovy - thyme" note could be conceived and be considered acceptable in presentation on appetizer croutons.

1-2-Thyme dried, leaves, origin France, initial storage 12 months before use After 3 weeks: The oily extract "B" is green, limpid, it has a weak smell of thyme, the smell of rancid and fish is undetectable.

The "thyme" flavor is intense, without any taste or aftertaste of fish oil; it is reminiscent of the aromatic notes "pizza"

The oily extract A is substantially less powerful, but presents no taste defect.

After 6 months:

Extracts A and B retained their satisfactory initial characteristics, compared with the corresponding controls stored at + 4 ° C.

The application to grated carrots, at the dose of Ig of oil for about 50g of vegetables; which corresponds to the recommended daily intake, communicates to them a frank thyme note and exhausts the overall bitterness, the latter is corrected by the use of olive oil. These extracts combine easily with lettuce salad or celery rémoulade. The application on croutons of toast remains the most acceptable.

1-3 Fresh thyme, undried, harvested at the end of flowering.

After three weeks the oily extracts A and B have a faint odor reminiscent of flaxseed oil and a poor fishy taste.

Overall the aroma more evokes that of Basil than that of Thyme After six months of storage, the characteristics have not changed, no significant degradation.

Example 2 EXTRACTS FROM A MIXTURE OF SPICES Powder called "FOUR SPICES" defined as a mixture of: Cinnamon, Clove, Ginger and Nutmeg Origin India- Shelf life before use unknown. After three weeks the oily extracts A and B have a smell of fish and cinnamon; the taste, unexpected is not unpleasant. The preservation test was not continued for lack of sufficient antioxidant activity.

EXAMPLE 3- EXTRACT OF CLOVE (Eugenia caryophyllata) called "cloves" whole, shelf life before use unknown.

After three weeks the oily extracts A and B present a clean fish note, associated with a note "eugenoloxidized", unpleasant.

This illustrates that a powerful antioxidant such as eugenol is unsuitable for the protection of marine oils, which is in line with example 2.

EXAMPLE 4-EXTRACTS OF INDIA WOOD (Pimenta racemosa) whole seeds

After three weeks the oily extracts A and B show a pleasant odor free from pest notes and a slightly resinous taste with the exception of any other taste note.

After six months the characteristics are unchanged, without appearance of oxidized notes or fish.

EXAMPLE 5-CURRY POWDER EXTRACTS The curries correspond to mixtures that vary according to the user countries.

Composition: Turmeric, Coriander, Mustard, Fennel, Cumin, Shallot, Pepper, Celery,

Fenugreek.

After three weeks, the oily extracts A and B have a very pleasant smell of "curry" and an identical taste, without parasite notes. After six months of storage, the characteristics of the extracts have not changed.

EXAMPLE 6-CUMIN EXTRACTS Seeds- (Cuminum cyminum) and CARVI (Carum carvi)

Two samples of different origins were tested. The results were found strictly comparable. After three weeks:

the oily extract A is clear, of a yellowish-green color with a clear odor of cumin, with no detectable traces of fish odor or oxidation products;

The taste of cumin is powerful, persistent, without oxidized notes or fish and without after-taste.

the oily extract B has similar characteristics with a slightly lower power, the product is "softer", more "round" in aromatic terms. After 6 months: extracts A and B maintained their satisfactory initial performance.

The application of these extracts to salad of lamb's lettuce and celery rémoulade gives very pleasant and very acceptable seasonings. The tomato salad has the taste of cumin.

The extracts of Carvi behave in a quite comparable way.

Carvi is botanically close to Cumin, this does not make it possible to extrapolate the positive effects obtained with umbelliferous seeds for example because there is not necessarily a concordance between the botanical classification and the chemical composition of the various plants of a plant. same botanical family, this reality is known to those skilled in the art.

EXAMPLE 7-EXTRACTS OF ORIGAN dry leaves (Origanum vulgare) Origin France, shelf life before use unknown.

After three weeks, the oily extract A is clear, yellowish, practically odorless; the notes oregano, oxidized and fish are imperceptible. Gustative: we perceive warm notes overall of "Mediterranean cuisine" free from spurious notes, including fish and oxidized. The oily extract B: is very comparable, but substantially less powerful. Controls 1 and 2 are oxidized.

After 6 months: extracts A and B have retained their satisfactory characteristics. In application in tomato salad the fish notes reappear, there is incompatibility, and this is the only case listed here between this food and the oily extracts considered. The acceptability of croutons of toast is satisfactory: lack of notes and aftertaste of fish.

Oregano and thyme are botanically close, but their chemical components are not necessarily similar or functionally equivalent, for this reason the production of vegetable extracts by unsaturated oils can constitute a test of evaluation of the antioxidant potential of a plant or a plant extract.

EXAMPLE 8 MUSCADE EXTRACTS, coarsely grated fruit (Myristica fragrans) Origin India - Shelf life unknown.

After three weeks, the oily extract B is clear, not very colored, and has a clean smell similar to that of linseed oil. The taste is distinct from that of nutmeg; floral, it recalls the crudités (radish). No parasitic oxidation or fish note defects. In application on a crouton of toast the whole is extremely pleasant: notes of the type "cracker" for appetizer.

The oily extract A is very much less powerful, but without any taste defect.

After 6 months: the performances of extracts A and B are at least conserved, even improved: aromatic notes more balanced, very aperitive.

When applied in a tomato salad, the taste is unusual, not unpleasant. Associated with a smoked fish (herring) the extract softens the smoke notes and as the cumin extract brings frank salmon notes free of oxidation.

These extracts, apart from their stabilizing effect, offer the flavourist and the cook the potential to create or reinforce new flavors.

Associated with the tomato salad, the oily extract B communicates cooked notes, unexpected confit; this observation reinforces the preceding remark.

EXAMPLE 9-AMOME CARD dry fruit (Elettaria cardamomum) Origin and shelf life unknown

Two different samples were used:

9.1 one old, practically discolored,

9.2 the other, newer, green pistachio

After three weeks the oily extract A from recent cardamom (green) is limpid, yellow with strong cardamom odor, without fish and oxidized parasite notes. The taste is only that of cardamom, powerful and durable, with no aftertaste of fish; the oily extract B is comparable qualitatively, but its power would make it possible to use an initial extractive mixture with 7 or 8% of cardamom.

In application in the seasoning of grated carrots, in the presence of lemon juice or vinegar the acceptability is very satisfactory, without rancid notes.

The same goes for seasoning a tomato salad.

The app on croutons of toast is the most palatable; it's the same with a pizza.

The addition to smoked fish preparations gives unexpected results: the flesh of smoked herring is perceived as that of a salmon very delicately prepared.

In these various applications: no rancid or oxidized after-taste is perceptible and only the taste of cardamom persists.

Oily extract A from old cardamom (discolored) has a fleeting "fish" attack note, followed by disappointing "clove" notes. After 6 months, oily extract samples A and B, described in 9-1 and 9-2, retained satisfactory sensory characteristics.

EXAMPLE 10 - EXTRACTS OF SAGE, leaves (Salvia officinalis)

10-1-Dry leaves Origin Germany-Shelf life 18 months.

(A witness unspecified fresh sage leaves, was also used in comparison)

After three weeks the oily extract A is limpid, with a unique scent of sage. Gustatively we observe a sage note associated with a trace of fish note.The power of the sage note is such that the implementation of the plant could be reduced and reduced to 6 or 7% (w / w) in the initial extractive mixture .

In application, the addition of seasoning extracts of grated carrots, tomatoes is very satisfactory and the parasite fish note becomes unapparent, even in the presence of lemon juice or vinegar. The preservation test was not continued because of the average performance as an antioxidant and because of the presence of thujone which presents a risk in case of repetitive use, which is the rule with the diets. enriched in polyunsaturated fatty acids.

This type of extract can be considered simply as a representative model of the antioxidant functionality of oily extracts of sage.

10-2-Fresh leaves:

After three weeks, the clear green extracts A and B do not smell like fish. Tastefully the fish note is found, associated with an unpleasant soapy taste.

EXAMPLE 11- EXTRACTS OF Dried, Crushed ECHALOTE BULBS (Allium ascalonium)

After three weeks the extracts A and B are limpid, golden yellow and have a pleasant sulfur odor associated with a note "sardine". The acceptability is good, the degradation is not aggravated compared to the witnesses of the starting oils, but its typicity and the nature of the parasitic note motivated the stopping of the test.

EXAMPLE 12 - EXTRACTS OF "PILI-PILI" or chili pepper "bird tongue" whole fruit (Capsicum frutescens) After three weeks the extracts A and B are bright yellow and have a simple juxtaposition of the spiciness to fish notes that have not worsened compared to the original witness and cast doubt on the interest and acceptability.

We are here typically in the case of a classic flavoring that juxtaposes aromatic or tasty notes with undesirable aromatic and taste notes, without complementarity or synergy.

EXAMPLE 13-EXTRACTS OF CORIANDER seed (Coriandrum sativum)

After three weeks the oily extracts A and B have an odor and a taste of fish.

EXAMPLE 14-MACIS POWDER EXTRACTS, dried arils of Myristica fragrans.

After three weeks, oily extracts A and B are clear and have a golden yellow color with a pleasant "floral" smell, very rich and very fine. Tastefully there are no noticeable fish and oxidized notes, the overall sensation is slightly peppery with a very sweet, green floral bouquet. After 6 months, the characteristics are unchanged.

If these aromatic characteristics are known for Macis in non-oily extracts, its stabilizing power remains unpublished.

EXAMPLE 15 - PEPPER EXTRACTS

Black pepper and crushed green pepper (Piper nigrum)

After three weeks, the strongly colored extracts A and B present fish notes.

EXAMPLE 16-EXTRACTS OF SPRAYED CANNELLE (Cinnamomum zeylanicum)

After three weeks the extracts A and B are limpid, slightly greenish, with a floral odor and a taste unoxidized and cinnamon linseed oil, unexpected, pleasant.

The originality of the tasting notes obtained would require the study of the culinary applicability in aperitif crackers for example. After six months, the characteristics have not changed: very good conservation.

These extracts can be considered as models of stabilizing activity and obtaining original flavors for the Aromatician and the Cook.

EXAMPLE 17-EXTRACTS OF ANETH + Dry leaves (Anethum graveolens) After three weeks the extracts A and B are limpid, greenish in color, the smell of dill is modified and the taste of fish is present, although it is softened.

EXAMPLE 18-BASIL EXTRACTS Fresh leaves (Ocimum basilicum) After three weeks, extracts A and B are clear and have a parsley odor combined with that of the fish note, as well as a rancid taste. Although acceptability remains good, the trial was not continued.

EXAMPLE 19-EXTRACTS OF SARRIETTE, fresh leaves (Satureia hortensis) After three weeks, extracts A and B are clear and have a pleasant fruity odor. The taste remains that of a fresh fish, moderately intense.

There is no oxidized aftertaste or fish.

Dry savory very quickly loses its aromatic qualities and has therefore not been tested. The use of oily extracts of savory seems to be reserved for a short-term use, although the synergy with the fish notes is aromatically promising.

EXAMPLE 20: COCOA EXTRACTS, powder (Theobroma cacao)

These extracts were made at the concentration of 5% (w / w) because of the aromatic power of cocoa.

After three weeks, extracts A and B present fish notes of the tuna and sardine type, without parasitic notes or cocoa notes.

The only potential interest of the trial is the potentiation of fish notes by cocoa extracts; the stabilizing effect, real, remaining marginal because one of the objectives remains the masking of fish tastes.

EXAMPLE 21 Extracts of Persil, Fresh Leaves (Petroselinum sativum-Petroselinum crispum var neapolitanum)

After three weeks the extracts A and B are limpid, colored green and have fish notes.

EXAMPLE 22: CHICOLATE EXTRACT, fresh leaves (Allium schoenoprasum)

After three weeks the extracts A and B have an alliaceous odor, and a taste of mussel broth which has only an aromatic interest. EXAMPLE 23: EXTRACT OF ROSEMARY fresh leaves (Rosmarinus officinalis)

Rosemary extracts, as mentioned above, are referred to as antioxidants.

The dry leaves of Rosemary degrade very quickly, especially by oxidation and are quickly invaded by molds that accelerate their degradation.

After three weeks the extracts A and B are limpid, of green color; without notable oxidation, with a discreet fish note but with an unpleasant soapy and earthy flavor.

It appears in these conditions that the extraction of antioxidants from rosemary by marine oils is insufficient and that some of the flavoring materials of this plant are inconsistently incompatible and insufficient to cover the fish notes.

Claims

1. Process for obtaining fish oil stabilized by plants and having satisfactory taste acceptability characterized in that it comprises the steps of: macerating away from air and light, under gas inert or under partial vacuum, a plant selected from the group consisting of thyme, wood of india, caraway, caraway, oregano, nutmeg, mace, cardamom, cinnamon or a plant composition consisting of a curry powder in a dietary fish oil rich in polyunsaturated fatty acids, especially omega-3 unsaturated fatty acids, for a duration of at least 20 days at a temperature of 20 ⁰ C +/- 5 ° C; after decantation of said plant material, recovering, clarifying and conditioning the supernatant in the absence of air, said process being carried out without volatile solvents and without heat input. 2. Method according to claim 1 characterized in that said fish oil is a line oil, shark, sardine, cod, herring or salmon. 3. Method according to any one of claims 1 or 2 characterized in that said plant is selected from the group consisting of wood of india, nutmeg, mace. 4. Method according to any one of claims 1 or 2 characterized in that said curry powder is a mixture of turmeric, coriander, mustard, cumin fennel, shallot, chilli, celery and Fenugreek . 5. Method according to any one of claims 1 to 4 characterized in that said maceration step is carried out with a maximum content of 10% by weight of said plant or said plant composition with respect to the weight of said oil. 6. Method according to any one of claims 1 to 5 characterized in that said plant used is a dried plant. 7. Method according to any one of claims 1 to 6 characterized in that it comprises a preliminary step of contusion of said plant. 8. Method according to any one of claims 1 to 7 characterized in that it includes a resuspension during said maceration step. 9. Product obtained by the method according to any one of claims 1 to 7 characterized in that it consists of a fish oil in which a plant macerated from the group consisting of thyme, indian wood, macerated. , caraway, caraway, oregano, nutmeg, mace, cardamom, cinnamon or a vegetable composition of a curry powder.