WO2021234067A1 - Procede de preparation d'un totum ou d'un filtrat permettant la stabilisation de matiere vegetale fraiche - Google Patents
Procede de preparation d'un totum ou d'un filtrat permettant la stabilisation de matiere vegetale fraiche Download PDFInfo
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- WO2021234067A1 WO2021234067A1 PCT/EP2021/063412 EP2021063412W WO2021234067A1 WO 2021234067 A1 WO2021234067 A1 WO 2021234067A1 EP 2021063412 W EP2021063412 W EP 2021063412W WO 2021234067 A1 WO2021234067 A1 WO 2021234067A1
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- oil
- fat
- totum
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Definitions
- the present invention relates to a process for preparing a totum or a solid or liquid filtrate at room temperature, from a fresh vegetable matter and a fatty matter, as well as the totum depleted in water or the liquid or solid filtrate which may be obtained according to said process, and their uses.
- a totum can be defined as a mixture of at least one plant material with at least one fatty material which is solid or liquid at room temperature.
- the totum thus comprises active compounds or metabolites in particular extracted from plant material and which can be transferred in part to the fat and in part to the plant residue.
- Active compounds or natural metabolites are molecules originating from plant material or part of plant material, the biological and technological activities of which have been demonstrated and described in the literature.
- These natural active compounds may be in pure form or contained in extracts in which the residue and solvent are separated.
- the benefit of these active compounds can be established in the context of food and / or human or animal welfare and / or health.
- Their use as additives can encompass various objectives, such as in particular: - improving health (antioxidant, anti-inflammatory, anti-microbial compounds in particular, alkaloids and polyphenols); - improvement of palatability (compounds increasing palatability such as aromatic compounds, terpenes or pigments such as carotenoids or chlorophylls); and - contribution to nutrition (nutrients such as proteins, amino acids, vitamins, trace elements, etc.).
- the natural metabolites of plant origin to which it is possible to attribute biological activities of interest in food and human or animal health can belong to different families of molecules. They are mainly secondary metabolites, which, unlike primary metabolites, are directly non-essential for nutrition, growth and development of the plant (Verpoorte, 2000, Secondary metabolism, In Metabolic engineering of plant secondary metabolism (p.1-29), Springer, Dordrecht). These are compounds whose biosynthetic pathways are quite specific to a taxonomic group and which generally participate in the interaction mechanisms between the plant and its environment (defense, resistance and responses to abiotic and biotic stresses, symbiosis, allelopathy. ..). There are different families of secondary metabolites of interest in food and animal health.
- alkaloids generally alkaline compounds which contain at least one nitrogen atom. These are compounds which generally have significant biological activity, in particular an action on the central and / or peripheral nervous system (stimulant or depressant), in particular as anesthetics, as hypertensives or anti-hypertensives, as antimalarials or even as anticancer drugs.
- Alkaloids are generally grouped together according to their nucleus (non-heterocyclic, derived from indole, pyrrole, pyridine, tropane, etc.). Among the alkaloids, we find well-known molecules such as caffeine, morphine, piperine, nicotine, atropine, scopolamine or even quinine.
- Capsaicinoids including capsaicin and dihydrocapsaicin can represent up to 90% of total capsaicinoids. These are the active components from chili peppers that are part of the benzylamine alkaloid group. The consumption of capsaicin activates the TRPV1 receptors which activate a burning sensation. It also stimulates the production of two hormones, adrenaline and norepinephrine and therefore has a therapeutic interest given its anti-inflammatory, antioxidant and analgesic properties (Zimmer et al., 2012, Antioxidant and anti-inflammatory properties of Capsicum baccatum : from traditional use to scientific approach. Journal of Ethnopharmacology, 139 (1), 228-233).
- Chlorophylls (a, b, c1, c2 and d) are pigments present in all green plants (terrestrial and aquatic). Chlorophyll a (C55H72O5MgN4) remains the form mainly found in the leaves of plants.
- Anthocyanins are water soluble pigments (oxygenated heterosides) that range from red to blue.
- Curcuminoids range pigments from the rhizome of Curcuma longa
- Flavonoids can range from a red to ultra-violet color depending on the pH and correspond to two aromatic rings linked by three carbons.
- Biochimica and Biophysica Acta (BBA) -Molecular Basis of Disease, 1740 (2), 101-107).
- the advantage of their use in animal feed is in particular that they combine their antioxidant activities with their participation in improving the visual quality (coloring and appearance) of the product formulation, as well as in the coloring and preservation of the products. animal products (meat, eggs).
- Terpenes are also interesting secondary metabolites. They are volatile compounds whose structure corresponds to an aromatic ring and which have hydroxyl and terpenoids groups. They are at the origin of the aromatic properties of certain plants according to their taxonomy. According to the literature, there are approximately 25,000 different structures of terpenes. To this are added the properties of another family which are essential components of essential oils: phenols.
- Phenols are the metabolites that give essential oils their very characteristic odor and biological activities.
- the essential oil of oregano is mainly composed of thymol (phenol monoterpenoids) and its isomer, carvacrol and ⁇ - terpinene, the presence of which gives the essential oil its antioxidant and antimicrobial properties.
- Natural compounds of plant origin have very wide applications in the fields of cosmetics and perfumery, but also in human and animal health and food. PRIOR ART Obtaining them generally involves first of all the harvesting, drying, storage and packaging of the raw plant material.
- Document FR2943684 describes, for example, a process for extracting non-volatile natural compounds, contained in a solid raw material of natural origin, in particular a plant, in a dispersible form, using a natural fatty substance or a mixture.
- natural fatty substances in particular a vegetable oil or a mixture of vegetable oils, characterized in that it comprises: a) a step of mixing and impregnating the solid raw material in dispersible form with the natural fatty substance at a temperature above the melting point of the fatty substance and in an atmosphere devoid of or essentially devoid of oxygen, b) a step of micro-dispersion of the solid material and optionally of rupture of the cells of the raw material, in the natural fatty substance at a temperature above the melting point of the fatty substance, and c) a step of heating the mixture to high temperature.
- Document FR3013979 describes a process for preparing a totum comprising the following steps: a) Preparation of dehydrated grape seeds in a form which is dispersible in an oil at a temperature above the melting point of the oil; b) Mixing the solid material obtained following step a) with the oil, or a mixture of oils; c) Thermal and physical treatment of the mixture by implementing: - at least one step of micro-dispersion of the solid material and breaking of the cells of the raw material, in oil at a temperature above the melting point oil ; - at least one high temperature heating step, advantageously between 80 ° -200 ° C, of the mixture over a very short period of time, and d) recovery of the oily composition following step c).
- Document EP3290499 describes a process for producing a totum, containing 3% by weight or less of water, comprising: a step which consists in bringing a fat into contact with powder of dried rosemary leaves; - a filtration step after the step of contact with the rosemary; - A deodorization step by heating to a temperature of 170 ° C. is carried out after filtration.
- Such documents therefore do not describe an “all-in-one” process for drying, grinding, eco-extraction, formulation, and stabilization of a fresh plant material in a fatty material that is solid at room temperature in order to obtain a solid totum at room temperature.
- ambient comprising active compounds or metabolites in particular extracted from plant material and which can be partly transferred into the fat and partly into the plant residue.
- the drying phase is a critical phase for any plant metabolite (Mediani et al., 2014, Effects of different drying methods and storage time on free radical scavenging activity and total phenolic content of Cosmos caudatus, Antioxidants, 3 (2), 358 -370).
- the degradation of certain molecules can also create degradation products that are toxic to cells (O'Brien et al., 2008, Aldehyde sources, metabolism, molecular toxicity mechanisms, and possible effects on human health, Critical reviews in toxicology, 35 ( 7), 609-662).
- the interaction of these with certain amino acids can also be feared during heating (pH-, water content-dependent) and produce the synthesis of new molecules modifying the aroma. and biological potential.
- Certain drying techniques have been developed in order to avoid the degradation and loss of thermolabile molecules, or whose hydrolysis or oxidation can be very rapid.
- Removing water from the plant therefore remains essential for its conservation, the stabilization of its chemical content and the preservation of its biological activities over the long term (Mediani et al., 2014, Effects of different drying methods and storage time on free radical scavenging activity and total phenolic content of Cosmos caudatus, Antioxidants, 3 (2), 358-370). It has also been shown that during storage and very dependent on storage conditions, the chemical profile of a fresh fruit or a fresh plant (carotenoids, polyphenols, vitamins, etc.) could be strongly affected and reduced in quantitative terms.
- Another common extraction process is to use volatile organic solvents such as petroleum ether, hexane, ethyl ether, acetone, carbon dioxide, benzene or toluene.
- volatile organic solvents such as petroleum ether, hexane, ethyl ether, acetone, carbon dioxide, benzene or toluene.
- the enfleurage is a process aimed at integrating the aromas of a fresh plant in an oil or fat by maceration.
- the fat can be heated upstream of the process and the plant is infused into the latter.
- the plant is separated from the swollen fat by filtration. This process mainly concerns flowers or aromatic herbs.
- a problem which the present invention proposes to solve consists in developing a new process for preparing a totum or a filtrate which is solid at room temperature from a fresh plant material and a fatty matter, easy and quick to use and allowing to preserve all the metabolic richness of the plant material and to avoid any degradation by oxidation of fragile molecules.
- the natural active compounds extracted are contained in a complex whole and act in synergy with each other, thus increasing the biological potential of the totum.
- Advantages provided The advantage of said process according to the invention is to use the fresh plant material, whole or in part, for example at the exit of the field, directly in the process according to the invention and to grind, dry and stabilize it in fat while retaining the maximum of its biological activities (little metabolic change). Integrating the fresh plant immediately after harvest presents a great advantage for those skilled in the art in terms of handling and transport, but also in terms of preserving the biological properties of the plant material, in particular a plant.
- the process makes it possible to stabilize by dehydration, block the access of oxygen to the active molecules (oxidation) by grinding the plant directly in the fat, the latter going to surround the fine particles of the plant and to provide fresh plant material.
- a fatty substance with antimicrobial properties in order to avoid the degradation of the active ingredients.
- stabilization via this process has an energy advantage because it is an “all-in-one” process.
- the fact of using a fatty substance that is solid (and not liquid) at room temperature in the process advantageously makes it possible to reduce the penetration of oxygen, light and water and makes it possible, unlike an oil which is liquid at room temperature, to stabilize the totum even more.
- Said process can likewise be used in order to stabilize manufacturing co / by-products from other sectors rapidly on leaving the factory. Said process is thus also part of the issue of valuation of co / by-products. Indeed, these by- or co-products are products evacuated by companies which are not or cannot necessarily be stored in optimal conditions, the companies not being compliant for this purpose. The financial burden due to the evacuation of the company's co / by-products (transport, destruction) is also greatly reduced or even eliminated. The idea is therefore to preferably set up the process directly on leaving the factory in order to stabilize the co / by-products as quickly as possible and keep them in good conditions, and thus be able to recover them subsequently.
- the totum or the filtrate resulting from the co / by-products obtained by the process constitute an optimized stable state in order to store them and enhance their chemical richness.
- the energy cost is lower than the successive use of several specific tools in that said process is a treatment of grinding, dehydration, mixing, extraction, formulation, all-in. -a.
- the fact of using a fatty substance which is solid at room temperature makes it possible to further simplify the transport of the finished product in that the totum obtained is solid and stable; in addition, the fact that it is substantially free of water generates a resulting less heavy weight and therefore a reduced transport cost.
- the first object of the solution to this problem is a process for preparing a totum which is a mixture of a plant material with a fatty material which is solid at room temperature, characterized in that it comprises the following steps according to which : (a) the plant material is fresh and comprises at least 10% water by mass of water relative to its total mass (mass / mass) before or after loss on drying, taken alone or as a mixture, whole or in part, is brought into contact, preferably with stirring, with the fat chosen from a fat and a hydrogenated oil, at a temperature between 50 ° C and 180 ° C; (b) the vegetable matter - fat mixture thus obtained is then ground at a temperature of between 50 ° C and 180 ° C; (c) the ground material obtained at the end of step (b) is heated,
- FIG. 1 represents the various steps (mixing, grinding, dehydration) of the process according to the invention for preparing a totum or a filtrate allowing the stabilization of fresh plant material.
- Figure 2 shows the different steps (mixing, grinding, dehydration) of a particular embodiment of the process according to the invention for the preparation of a totum or of a filtrate allowing the stabilization of fresh plant material, in which the intake of fresh plant material is done in two stages.
- Figure 3 shows a photo of a totum obtained by the process according to the invention using a fresh Habanero pepper and glycerol monolaurate.
- Figure 4 shows the quantification of the carotenoids identified in the samples of fresh Habanero pepper, dried in an oven at 100 ° C and dehydrated according to the method according to the invention implemented in the context of Example 5.
- Figure 5 more particularly represents the absolute quantification of different carotenoids of interest in nutrition / animal health (lutein; ⁇ -carotene and zeaxanthin) identified in the samples of fresh Habanero pepper, dried in an oven at 100 ° C and dehydrated according to the method according to the invention implemented in the context of Example 5.
- FIG. 6 represents the absolute quantification of the capsaicin identified in the samples of Habanero pepper and red pepper, respectively fresh, oven-dried at 100 ° C. and dehydrated according to the process according to the invention implemented in the context of example 5.
- Description of the embodiments The invention relates to a process for preparing a totum or a solid filtrate at ambient temperature. e from fresh plant material and fat.
- the invention relates to a process for preparing a totum or a filtrate that is liquid at room temperature, from a fresh plant material and a fat.
- solid at room temperature is meant a state of matter having a specific shape and a specific volume, and which can be handled and moved without this shape or volume changing, as opposed to a liquid state.
- liquid at room temperature is understood to mean another state of the deformable material, whatever its viscosity, including viscous fluids. As the ions, atoms and molecules are not closely connected, the liquid takes the form of the container in which it is placed and flows more or less well depending on its viscosity.
- the liquid has a viscosity of 0.1 cP and 100,000 cP.
- fresh plant material is meant a living organism forming part of the plant kingdom, including aquatic plants, whole or in part, comprising at least 10% water by mass of water relative to its total mass (mass / mass) before or after loss on drying, preferably at least 69% (mass / mass), more preferably at least 79% (mass / mass).
- a dry matter generally has a water content which is at most of the order of 5% (mass / mass).
- the fresh plant material, taken alone or as a mixture, in whole or in part, used in the process according to the invention is preferably chosen from fruits, whole plants, aerial parts of plants, roots, bulbs, tubers, seeds such as pips. of grapes or citrus fruits, skins such as pomegranate or citrus fruit peel, pulps, macerates, cake, or any other by-product / co-product of vegetable matter such as plant or pressed fruit residues.
- the fresh plant material, taken alone or as a mixture, in whole or in part, used in the process according to the invention is more preferably chosen from wormwood, yarrow, garlic, wild garlic, artemisia, artichoke, pink berry, berry goji, burdock, basil, coffee, chamomile, cinnamon, blackcurrant, lemon, lemongrass, hemp, coriander, turmeric, cypress, eucalyptus, fenugreek, ash, juniper, clove, ginseng, ginger, pomegranate, hibiscus, hops, bay leaf, lavender , lemon grass, alfalfa, flax, mint, peppermint, mallow, lemon balm, mustard, white mustard, walnut, hazelnut, orange, oregano, nettle, onion, paprika, pansy, pepper, chili, pine, dandelion, pepper, rosemary, grape, savory, sage, wild thyme, marigold, tansy, tea
- the fresh plant material can generally only be kept as it is for a short time, for example a maximum of a few hours, after harvesting or recovery for by-products / by-products, otherwise it will degrade and lose a large part and sometimes all of their active metabolites of interest and the associated biological activities.
- the plant material will be put into the fat directly after harvest or recovery, or at least as quickly as possible, for example 12 hours, and will preferably be used within 3 hours, in order to keep all the active metabolites. of interest.
- the fat used in the process according to the invention is chosen from a fat or an oil which may or may not be hydrogenated, preferably a fat or a hydrogenated or partially hydrogenated oil, solid at room temperature, taken alone or as a mixture.
- hydrogenated or partially hydrogenated fat or oil which is solid at room temperature
- the fat used insofar as obtaining a total solid at room temperature is desired, is preferably a hydrogenated or at least partially hydrogenated fat or oil, solid at room temperature, advantageously exhibiting a melting point greater than 27 ° C, preferably greater than 30 ° C.
- the fat used is preferably an oil which is liquid at room temperature, in particular a non-hydrogenated oil having a lower melting point. at 30 ° C, preferably less than 27 ° C.
- ambient temperature is meant a stable temperature but not necessarily controlled, which is generally 20 ° C but which can be between 15 ° C and 27 ° C.
- the fat preferably used in the process according to the invention is chosen not only by virtue of its efficiency and its advantage in terms of the process but also of its cost, its texturing properties and its advantage of use as a food component (energy supply or activities. biological antioxidant, antimicrobial, anti-inflammatory for example).
- the fat preferably solid at room temperature, is more preferably chosen from glycerol monolaurate, glycerol monocaprate, glycerol monomyristate, glycerol monopalmitate, glycerol monostearate, almond oil, peanut oil, argan oil, avocado oil, calophyllum oil, safflower oil, rapeseed oil, coconut oil, wheat germ oil, jojoba oil, corn oil, hazelnut oil, apricot kernel oil , virgin olive oil, palm oil, grape seed oil, castor oil, sesame oil, soybean oil, or sunflower oil, the oils abovementioned being hydrogenated or at least partially hydrogenated so as to be solid at room temperature, even more preferably glycerol monolaurate, glycerol monocaprate, hydrogenated palm oil and hydrogenated sunflower oil, more preferably still glycerol monolaurate.
- certain fats used in the process according to the invention are effective solvents, that is to say they allow the transfer of molecules from the plant material into the solvent; this is the case in particular with glycerol monolaurate, glycerol monocaprate and olive oil for example, unlike, for example, sunflower oil or palm oil which have a lower solvent power.
- the intrinsic properties of the fats or oils used, in particular fats and more particularly glycerol monolaurate make it possible to optimize the process and the product resulting from said process.
- the fats or oils preferably hydrogenated or partially hydrogenated fats and oils which are solid at room temperature, create an anaerobic or at least micro-anaerobic environment during the process and inhibit the survival and development of strict aerobic microorganisms.
- This is intensified by the fact that the hydrogenated or partially hydrogenated fats and oils which can be used for the process are advantageously solid at room temperature and therefore impermeable to air and therefore restricting the colonization of microorganisms within the totum.
- the Applicant has been able to demonstrate that glycerol monolaurate, lauric acid monoglycerol (or 2,3-dihydroxypropyl decanoate), constitutes a particularly advantageous fat according to the invention, the interests of which are multiple.
- Glycerol monolaurate is a natural fatty acid mono-ester whose composition (more polar than certain vegetable oils) allows more particularly an extraction of amphiphilic compounds such as capsaicinoids. Its use does not pose any risk to humans or animals. In addition, it shows pronounced antibacterial, antifungal and anti-inflammatory activities. It can be used as an anti-microbial agent and in particular inhibits the growth, in vitro but also in vivo, of strains of Candida.
- glycerol monolaurate blocks the production of certain exo-enzymes and virulence factors such as protein A, ⁇ -hemolysin, ⁇ -lactamase and toxin 1 responsible for toxic shock syndrome (TSST-1 ).
- Glycerol monolaurate can moreover act in synergy with other products, such as aminoglycosides, in particular in the destruction of biofilm of antibiotic-resistant strains of Staphylococcus aureus. Indeed, prior treatment with glycerol monolaurate would improve the response of biofilms to antibiotics.
- Glycerol monolaurate by virtue of its emulsifying, solvent, physicochemical and antibacterial properties is the fatty substance more preferably chosen for the implementation of the process for preparing a totum or a filtrate according to the invention.
- glycerol monolaurate has never been disclosed to replace any extraction solvent in an associated process. Indeed, although its physicochemical properties make it an extraction solvent of choice, it is mainly for its antimicrobial (WO2016169129, WO9531966) and anti-inflammatory properties that it has been put forward so far. Glycerol monolaurate has also been described as a constituent of a combination of essential oil molecules used as a preservative for cosmetic products (inhibition of Aspergillus niger, Candida albicans, Staphylococcus aureus, and Pseudomonas aeruginosa) (WO2019047004) .
- glycerol monolaurate As the fat of the process (versus hydrogenated palm oil) made it possible to slow down or even inhibit the proliferation of microorganisms in the product obtained.
- the method according to the invention comprises a first step (a) in which the fresh plant material comprising at least 10% water by mass of water relative to its total mass (mass / mass) before or after loss on drying, taken alone or as a mixture, whole or in part, is brought into contact, preferably with stirring, with the fat chosen from a fat and a hydrogenated or non-hydrogenated oil, preferably a fat and a hydrogenated or partially hydrogenated oil which are solid at room temperature, at a temperature between 50 ° C and 180 ° C, preferably between 60 ° C and 130 ° C, more preferably of the order of 100 ° C.
- the fat chosen from a fat and a hydrogenated or non-hydrogenated oil, preferably a fat and a hydrogenated or partially hydrogenated oil which are solid at room temperature, at a temperature between 50 ° C and 180 ° C, preferably between 60 ° C and 130 ° C, more preferably of the order of 100 ° C.
- the step of bringing the fresh plant material into contact with the fat is preferably carried out with constant stirring of between 300 and 2,500 revolutions per min (rev / min), preferably with constant stirring of the order of 500 rev / min.
- a scraper or mixer ensures constant contact of the fresh plant material, whole or in part, with the fat and also makes it possible to evacuate the water during the process.
- This first step of the process makes it possible to melt the fat, insofar as it is solid at room temperature, for example glycerol monolaurate or hydrogenated sunflower oil, to cook the fresh vegetable matter in contact with the fat and consequently improve the grinding which is the next step.
- This mixing / heating step is essential because it allows the evaporation, at least in part, of the water from the fresh plant material.
- the fat used is a fat or a hydrogenated or partially hydrogenated oil that is solid at room temperature, it will, because of the temperature, become liquid and surround, protect the fresh vegetable matter which is subjected to an increase temperature.
- the duration of this mixing / heating step depends on the fresh plant material used and its water content.
- This step should advantageously be carried out in a time necessary and sufficient for the fat which may be solid at room temperature to be liquefied to allow effective subsequent grinding, unlike dry grinding in flakes of fat. It cannot therefore be only a few seconds, in particular for a fat that is solid at room temperature.
- the fat used has a solvent power, preferably glycerol monolaurate taken alone or in combination, it also makes it possible to extract, at least in part, that is to say to transfer the metabolites of the material.
- fresh vegetable in the fat is preferably brought into contact with the fat for a period of between 5 min and 40 min, for example 10 min, 15 min, 20 min, 25 min, 30 min or 35 min, preferably between 5 min and 20 min.
- the vegetable matter - fat mixture obtained in (a) is then ground at a temperature of at least 50 ° C, preferably between 50 ° C and 180 ° C, more preferably between 60 ° C. and 130 ° C, more preferably still of the order of 100 ° C.
- the step of grinding the vegetable matter - fat mixture can be of a few seconds, and is preferably carried out for a period of more than 2 minutes, preferably between 3 min and 15 min depending on the plant material, more preferably between 3 min and 5 min.
- the grinding is advantageously carried out so that the totum obtained in fine forms a smooth paste, and that the particles of crushed vegetable matter remain in suspension in the fat so that, during cooling, the residue of vegetable matter does not settle. not below.
- the totum thus obtained in fine is homogeneous and comprises particles invisible to the naked eye.
- the grinding is advantageously carried out by toothed knives.
- the grinding of the fresh plant material in the fat is carried out all at once, or in several stages, depending on the type of plant material and its richness, in particular in cellulose, lignin, the presence of seeds, nuts or bark.
- the step of grinding the mixture of vegetable matter - fat is preferably carried out with stirring between 500 rpm and 3500 rpm, more preferably between 1000 rpm and 2500 rpm, depending on the plant material, even more preferably with constant stirring of the order of 2500 rpm, for example by means of said scraper ensuring constant contact of the fresh crushed plant material with the fat.
- the fresh vegetable matter and / or the fat advantageously the fresh matter, can be introduced all at once from the start of the process or alternatively in several installments, for example in 2 to 4 times during the process, steps mixing / heating (step a), grinding (step b) (and dehydration (step c)) being advantageously carried out after each addition of fresh plant material as illustrated in FIG. 2.
- 1 / 3 (mass / mass of the total intake) of fat, preferably glycerol monolaurate, and 1/3 (mass / mass of the total intake) of fresh vegetable matter, preferably peppers, are added from the start of the process . They are brought into contact with stirring at 100 ° C. for 10 min then the mixture is ground with knives at 2500 rev / min, 100 ° C, for 5 min; again 1/3 (mass / mass of the total intake) of fresh plant material is added, the mixture being heated for 10 min at 100 ° C, and consequently the mixture is ground for 5 min at 2500 rpm. This makes it possible to incorporate a larger proportion of fresh vegetable matter into the fat.
- 1/3 (mass / mass of the total intake) of fat, preferably glycerol monolaurate, and 1/3 (mass / mass of the total intake of fresh vegetable matter, preferably peppers) are introduced from the start of the process They are brought into contact with stirring at 100 ° C for 10 min, then the mixture is ground with knives at 2500 rpm, 100 ° C, for 5 min; again 1/3 (mass / mass of the total intake) of another fresh plant material, advantageously an aromatic plant (for example thyme) is added, the mixture being heated for 10 min at 70 ° C, lower temperature so as not to alter the volatile secondary metabolites of aromatic plants (active), then the mixture is ground for 5 min at 2500 rpm.
- an aromatic plant for example thyme
- the fresh vegetable matter and the fat are advantageously used according to a final ratio in mass / mass of fresh vegetable matter / fat of 1 : 1 to 5: 1, preferably from 1: 1 to 2: 1, more preferably Also from 1: 1 to 1.5: 1, the optimum being dependent on the initial water content of the fresh plant material.
- step (c) the ground material obtained at the end of step (b) is heated, preferably with stirring, to a temperature of at least 50 ° C, preferably between 50 ° C and 180 ° C, more preferably between 60 ° C and 130 ° C, more preferably still of the order of 100 ° C, to dehydrate the mixture, by evaporation of the water; in the case where the fat used has solvent capacities, this step promotes the transfer of molecules from the plant to the fat: we speak of eco-extraction.
- the duration of this heating step is dependent on the initial water content of the plant material used in the process. The higher the water content, the longer the heating / mixing time (step c) and the evaporation of the water must be.
- This additional heating step is preferably carried out with constant stirring.
- the ground material is preferably heated with constant stirring with a scraper at 500 rpm for 5 to 40 min, for example 10 min, 15 min, 20 min, 25 min, 30 min, 35 min, preferably 5 min to 20 min , more preferably 10 min, at a temperature of 100 ° C in order to continue and optimize the eco-extraction of plant matter metabolites in fat.
- This step is particularly advantageous because it makes it possible to make the active plant metabolites more bioavailable by removing them from the plant cells, which are nevertheless protected from potential degradation by their immediate contact with the fat.
- the steps of mixing / heating (step a), of grinding (step b), and of heating / mixing of the ground material (step c), are preferably carried out in the darkness.
- darkness is meant the total absence of light, visible or invisible, natural or artificial.
- Carrying out the process according to the invention in the dark advantageously makes it possible to protect the molecules from degradation due to light (UV) and thus to avoid any loss of molecules of interest by oxidation.
- carrying out the steps of heating / mixing and grinding the fresh plant material directly in the fat, and in the dark makes it possible to reduce the risk of oxidation and loss of active compounds.
- a device allowing the implementation of the method according to the invention, mention may be made of the ROBOQBO 8L® or the HYDROGRIND® equipped with knives with teeth with a rotation speed of between 500 and 3000 rpm, d '' an integrated heating system allowing products to be brought up to 180 ° C, and also a 900 mbar vacuum system and a cleaning system.
- the water evacuated in the form of steam throughout the process is eliminated through an outlet placed on the upper part of the machine.
- Such a device therefore makes it possible in particular to control the conditions relating to the atmosphere (O2 / CO2, ventilation), humidity, temperature and agitation of the fresh plant material used in the process according to the invention. These are important conditions to control when working with fresh plants.
- the process according to the invention thus makes it possible to dry the fresh vegetable matter and to preserve all the metabolic richness thereof in the hot fat at a temperature of between 50 ° C and 180 ° C, in order to avoid any degradation by oxidation of the fragile molecules.
- the grinding of the plants is also carried out in the hot fat, preferably at a temperature between 50 ° C and 180 ° C, which facilitates the grinding and limits the contact of the cellular content of the plant material with the oxygen of the plant. 'air.
- the mixture of fat / fresh plant is stirred throughout the process by a scraper rotating at a speed of between 300 rpm and 600 rpm, advantageously constantly at 500 rpm,
- the process according to The invention is carried out for a total period of between 13 min and 60 min to minimize energy costs, for example 15 min, 18 min, 20 min, 23 min or even 25 minutes.
- the water is evacuated in the form of steam. Water vapor is released throughout the process.
- Heating / mixing at a temperature preferably between 60 ° C and 130 ° C, more preferably of the order of 100 ° C, grinding the plant material in the fat, then again heating / mixing preferably between 60 ° C and 130 ° C, more preferably of the order of 100 ° C and constant agitation during the process will allow the water to be evacuated from the plant cells, and ultimately obtain a total or a depleted filtrate in water.
- the phenomena of hydrolysis of plant molecules, entrainment in steam and oxidation are limited by the fact that the plant material is introduced and cooked in the fat and that the release of metabolites takes place, during grinding and processing. mix with preferred temperatures of 100 ° C, in liquid fat.
- the plant cells are completely surrounded by the liquid fat during the process.
- the water content of a sample of the dehydrated ground material obtained at the end of step (c) is measured for example by infrared balance.
- a solid or liquid totum, preferably solid, at room temperature with a content less than or equal to 4% water by mass of the total mass of the totum, preferably less than 2.5 % (mass / mass), more preferably less than or equal to 1% (mass / mass) is finally recovered in a last step (d).
- the plants are dehydrated (or dried) after 13 minutes of heating and grinding in fat or oil, advantageously at 100 ° C., and this at a level of 99%.
- the method can integrate, at the same time or in an additional step, the application of microwaves and / or ultrasound so as to accelerate the rate of evaporation of the water from plant matter and the extraction of plant metabolites in the fat having a solvent power.
- an additional step of filtering the mixture of vegetable matter - fat thus obtained is carried out at the end of step (b) or (c). This filtration makes it possible to eliminate the residues of plant material having a particle size greater than 200 ⁇ m or preferably than 100 ⁇ m, before being recovered to obtain a solid or liquid filtrate, preferably solid, at room temperature.
- the additional filtration step is carried out hot, at a temperature between 50 ° C and 180 ° C, to obtain a solid filtrate at room temperature.
- the separation of the filtrate and the residue of plant material is carried out by hot filtration (for example 90 ° C) under vacuum or by centrifugation (for example 3000g) in hot (for example 90 ° C) .
- another object of the invention relates to a process for preparing a solid or liquid filtrate, preferably solid, with ambient temperature, characterized in that it comprises the following steps according to which: - a fresh plant material comprising at least 10% water by mass of its total mass before or after loss on drying, taken alone or as a mixture, whole or in part, is brought into contact, preferably with stirring, with a fatty material chosen from a fat or a hydrogenated or non-hydrogenated oil, at a temperature between 50 ° C and 180 ° C; - the mixture of vegetable matter - fat thus obtained is then ground at a temperature between 50 ° C and 180 ° C; - The ground material thus obtained is heated, preferably with stirring, to a temperature between 50 ° C and 180 ° C, preferably between 60 ° C and 130 ° C, more preferably of the order of 100 ° C, to dehydrate the mixture ; - an additional step of mixing the ground material obtained at the end of step (b) at a temperature between 50 ° C
- the water content of the totum or of the solid or liquid filtrate, preferably solid, at ambient temperature thus recovered is advantageously measured at the end of the process as is the activity of the water and will be correlated with the life of the product ( microbial contamination-degradation of assets). If the fat has antimicrobial properties, such as, for example, advantageously glycerol monolaurate, and the water in the fresh plant material is eliminated in its entirety, the totum or final filtrate will be optimally stabilized for storage and preservation. If the fat becomes solid again at room temperature, the totum is a product advantageously formulated as it is. To this end, another object relates to a solid or liquid totum or filtrate, preferably solid, at room temperature which can be obtained by the process according to the invention.
- the totum or filtrate thus obtained is a smooth paste stabilized by its low moisture content and / or by its antimicrobial properties, which can be poured immediately into a suitable container.
- the totum thus obtained is liquid with substantially fine dried vegetable particles resulting from the grinding in suspension in the oil or the fat.
- the liquid totum can be filtered to remove residues of plant material having a particle size greater than 200 or preferably 100 ⁇ m and the filtrate used as it is or as a mixture with other compounds.
- This totum or filtrate is preferably stored in solid form if the fat used is a hydrogenated or partially hydrogenated fat or oil, the melting point of which is greater than room temperature. .
- the totum or filtrate which is solid at room temperature can then be remelted in order to be incorporated into a mixture or ground in order to be used in an additional process of encapsulation or of adding another material, vegetable or not.
- the totum produced during said process is defined as the mixture of the dried-dehydrated, crushed, optionally eco-extracted, formulated and stabilized plant material in the fat.
- the totum is a mixture of finely ground plant particles, surrounded by the fat.
- the filtrate obtained by the process according to the invention is devoid of particles and essentially comprises the metabolites extracted from the starting fresh plant material.
- the fact that the fats used can be solid at room temperature reinforces the protection of the plant molecules in the totum or filtrate, and therefore the conservation of the totum or filtrate over time.
- the totum or filtrate which is solid at room temperature is therefore a stabilized state of the fresh plant material used in the process.
- the totum or filtrate obtained according to the invention is depleted in water, with a content less than or equal to 4% water by mass of the total mass of the filtrate, preferably less than 2.5% (mass / mass), more preferably less or equal to 1% (mass / mass), the water from the plant material having been removed during said process.
- the totum, or filtrate in the case where the fat has the capacity, even limited, to extract, produced by the process according to the invention comprises active compounds extracted from fresh plant material.
- active compounds of interest and targeted that is to say preferred, during the application of said method, there may be mentioned a family of alkaloids: capsaicinoids (capsaicin, dihydrocapsaicin, nordihydrocap-saicin).
- capsaicinoids capsaicin, dihydrocapsaicin, nordihydrocap-saicin
- pigments of the carotenoid type capsanthin, lutein, capsorubin, zeaxanthin, ⁇ -carotene, ⁇ -cryptoxanthin, ⁇ -cryptoxanthin, antheraxanthin
- the temperature of the process can be adapted in order to extract and not to deteriorate molecules of aromatic and volatile types such as p-cymene, ⁇ -terpinene, ⁇ -pinene, 1,8-cineole, cis-sabinene hydrate, linalool , camphor, borneol, terpinen-4-ol, trans-p-mentha-1 (7), 8-dien-2-ol, verbenone, bornylacetate, ⁇ -terpineol, car-vone, thymol, carvacrol, piperitenone, eugenol, ⁇ -y GmbHe, car-vacrol acetate, methyl-eugenol, caryophyllene, ⁇ -humulene, cis-calamenene, ⁇ -calacorene, caryophyllene oxide, 14-hydroxy- (Z) ca-ryophyllene, abetatriene, 14-hydroxy -9-epi-
- the temperature of the process must be adapted and not exceed 80 ° C.
- the temperature should be between 50 ° C and 80 ° C, more advantageously between 50 ° C and 60 ° C, preferably with an application of vacuum.
- a lower temperature may be applied throughout the process (60 ° C instead of 100 ° C) with a vacuum application. Switching on the mixture makes it possible to reduce the melting and evaporation temperature of the water.
- the water boils at 100 ° C. under an atmospheric pressure of 1013.25 hPa. Under a pressure of 700 hPa, water boils between 90 ° C and 91 ° C. Under a pressure of 300 hPa, water boils between 73 ° C and 75 ° C.
- all of the extracted compounds can act in synergy with each other and with the solvent (intelligent solvent, ie with solvent properties that can achieve eco-extraction of the active ingredients but also possessing biological properties of interest (antimicrobial) and of formulation matrix) which is preferably glycerol monolaurate, depending on their properties (antioxidant, antimicrobial, anti-inflammatory, etc.).
- the solvent inlligent solvent, ie with solvent properties that can achieve eco-extraction of the active ingredients but also possessing biological properties of interest (antimicrobial) and of formulation matrix
- the solvent preferably glycerol monolaurate, depending on their properties (antioxidant, antimicrobial, anti-inflammatory, etc.
- the totum or the filtrate preferably obtained has, due to the presence of glycerol monolaurate, but also various pigments extracted during the process, a smooth, colored and shiny appearance. In the event that the extracted plant material comes from an aromatic plant (rosemary or oregano to name just two), the totum has the characteristic odor of these plants.
- a subject of the invention is also the use of a totum or of a filtrate according to the invention, for the preparation of a food composition, preferably for animal nutrition, or cosmetic.
- the totum or the filtrate loaded with compounds of interest can then be formulated according to the needs and the target animals and proposed for example for their different properties as feed additives for production animals.
- the filtrate or the totum are preferably formulated in the form of powder, granule, pebble, ointment, paste, capsule, microcapsule or tablet.
- the last subject of the invention is a composition comprising a totum or a filtrate according to the invention, for its pharmaceutical, nutraceutical or animal health use.
- nutraceutical product is meant a totum or filtrate obtained by the process from food, is formulated for example in the form of powder, granule, pebble, ointment, paste, capsule, microcapsule or tablet, having a physiological effect beneficial or providing protection, in particular against chronic diseases. Examples The present invention will now be illustrated by means of the following examples: Example 1: Process according to the invention for the preparation of a totum or of a filtrate FIG. 1 illustrates the sequence of the various steps inherent in the process of the invention.
- a first step of bringing into contact the fresh plant raw material (s) which can be whole plants, parts of plants (fruits, leaves, etc.), industrial co-products, fresh ( with a water content greater than 10%), preferably fruits of the genus Capsicum and of the fatty material (s), preferably monolaurate glycerol, and to mix them at a temperature of 100 ° C, advantageously (or between 50 and 180 ° C).
- a step of grinding the plant material in the fat always at high temperature (100 ° C).
- a step of mixing and dehydration of the ground material by evaporation of the water contained in the latter ideally at 100 ° C. or more).
- Example 2 Particular embodiment of the process according to the invention for preparing a totum or a filtrate, in which the supply of the fresh plant material is carried out in two stages.
- FIG. 2 illustrates an example of a supply in two successive batches of fresh vegetable matter.
- each intake follows the stages of mixing, grinding, dehydration, or a cycle. This specific case is applied when it is desired to load the totum significantly with plant matter.
- the plant supply must nevertheless preferably be treated in at least twice, given that the proportion of plant, before evaporation of the water, must be close to that of the fat so that there is contact from the start. start of the process and that the fat can surround all the plant cells during the initial mixing.
- the water from the fresh plant material introduced at the start of the process will have been eliminated, at least in part, and the volume of plant thus reduced in order to make room for a new supply.
- Example 3 Dehydration of different fresh vegetable materials via said method and comparison with the method on dry vegetable powder
- the fresh vegetable matter comprising a water content of 69% to 94% (Table 1) followed the drying / grinding process in 2 distinct fats in proportions of vegetable matter varying from 70 to 50% (Table 2).
- the process was carried out in a ROBOQBO® mixer / grinder, equipped with knives with teeth rotation speed 500 to 3000 rpm, an integrated heating system allowing the products to be raised up to 120 ° C and a 900 mbar vacuum system.
- the vegetable materials and the fats / oils were respectively brought into contact according to the proportions defined (Table 2) and heated to a temperature of 100 ° C. for 10 minutes with stirring of between 500 rev / min to 3000 rev / min. Grinding was then carried out for 5 or 10 min (depending on the plants) minutes still at 100 ° C.
- the ground vegetable matter / melted fat was stirred with a mixer for 20 or 25 min at 2500 rpm, thus making it possible to prolong the heating of the ground material, the evaporation of water, and in the case where fat has solvent properties, the transfer of metabolites from the plant to fat.
- the water vapor was evacuated throughout the process by an air outlet on the upper face of the machine.
- the smooth paste thus obtained is poured immediately, before freezing at room temperature, into aluminum trays.
- the humidity was measured with an infra-red balance (and validated by oven drying of plant materials and products).
- the process was also carried out with a dry chili powder having a water content of 5.11% and glycerol monolaurate (50:50) as a control.
- Table 1 Measurement of the water content of the plant materials used
- the product resulting from the process with the dry plant powder has a water content of 0.23% (Table 2).
- Table 2 the products obtained by the process according to the invention derived from fresh plant materials and from glycerol monolaurate have water contents of 0.6% to 2.4%.
- the products obtained by the process according to the invention obtained from fresh plants and hydrogenated palm oil have water contents of 0.63% to 0.79%.
- the totum obtained from a fresh material or from a dry material is stable because it has a water content of less than 4%.
- the process according to the invention therefore makes it possible to replace the drying and grinding upstream of the plant material, a step which is costly in terms of energy and chemical loss, by grinding and dehydration all in one, ultimately obtaining a stabilized totum.
- Example 4 Example of parameters of the process according to the invention using a fresh Habanero pepper (water content 91%) and glycerol monolaurate (GML or MGL) The various steps of the method according to the invention are implemented according to the conditions defined in Table 3 below.
- Table 3 The totum thus obtained comprises a water content of the order of 2% and has the appearance of a smooth and homogeneous paste as illustrated in FIG. 3 and having a strong sensation of spiciness.
- Example 5 Measurement of the impact of the process on the metabolites of interest extracted from peppers The process described below was implemented using Habanero peppers, the water content of which is indicated in Table 1 above. .
- the process therefore has a total duration of 35 min.
- the totum obtained was cast while hot in a mold, and observed in section and then ground in order to observe its physical behavior on grinding (viscosity, particle size, color, odor and pungent).
- glycerol monolaurate makes it possible to obtain a much more colored totum because the metabolites of fresh pepper, here more specifically the carotenoids, have been eco-extracted and transferred from the fresh plant material to the fat. (GML).
- Totum with glycerol monolaurate therefore has a more attractive character for humans or animals.
- the dosage of carotenoids (comparison of fresh fruit, fruit dried at 100 ° C., and product resulting from said process) was thus carried out.
- Methanolic extractions were thus carried out from: 1) fresh fruits of Habanero pepper; 2) whole fruits dried in an oven at 100 ° C of Habanero pepper; and 3) totum resulting from the process, from Habanero pepper, as described above. Following these extractions, the extracts were analyzed by UHPLC-DAD-MS / MS. Carotenoids were identified by their representative DAD spectrum. Some carotenoids could be quantified by parallel analysis of a reference range of the analytical standard. Each dosage was standardized in order to be placed in equivalent of the dry mass of the pepper and to be able to establish a comparison as for the potential loss of metabolites following drying.
- the sum of the identified carotenoids is much higher, as expected, in the fresh fruit (Habanero pepper).
- the sum of the identified carotenoids is in greater quantity in the totum resulting from the process according to the invention (54% of the fresh fruit) than in the chilli pepper dried in an oven at 100 ° C. (47% of the fresh fruit).
- dehydration by the process according to the invention globally protects this class of molecules from degradation by heat or at least does not cause more degradation than during dehydration in an oven, for a lower energy cost provided by the all-in-one of the process.
- the absolute quantification ( ⁇ g / g dry matter of chilli) of different carotenoids of interest in nutrition / animal health, classified in order of interest (A) lutein; B) ⁇ -carotene; C) zeaxanthin) identified in the samples of fresh Habanero peppers, dried in an oven at 100 ° C and dehydrated according to the process according to the invention, is illustrated in Figure 5.
- lutein and ⁇ -carotene like most of the carotenoids studied in products based on green, red and Habanero peppers, are in greater concentration in fresh fruit.
- the quantity of these carotenoids of interest is greater in the totum resulting from the process according to the invention than in the pepper dried in an oven.
- certain metabolites zeaxanthine are present in greater quantity (in the fresh fruit and) the dried fruit in comparison with the totum resulting from the process.
- the dosage of capsaicin was also carried out (comparison of fresh fruit, fruit dried at 100 ° C, and product resulting from said process).
- Methanolic extractions were thus carried out from: 1) fresh fruits of Habanero pepper on the one hand and red pepper on the other; 2) whole fruits dried in an oven at 100 ° C, Habanero pepper on the one hand and red pepper on the other; and 3) totum resulting from the process, from Habanero pepper on the one hand and red pepper on the other hand, as described above.
- the extracts were likewise analyzed by UHPLC-DAD-MS / MS as described in the section on analyzes of the carotenoids. Each dosage was standardized in order to be placed in equivalent of the dry mass of the pepper and to be able to establish a comparison as for the potential loss of metabolites following drying.
- the absolute quantification of capsaicin in samples of Habanero peppers and fresh red peppers, dried in an oven at 100 ° C and dehydrated according to the method according to the invention, is illustrated in Figure 6 (A- case of Habanero pepper and B- case of red pepper) representing the quantity of capsaicin in mg / g (UHPLC-MSMS, MRM identification mode).
- Habanero pepper contains a high content of capsaicin (10.9 mg / g DM) compared to red pepper (0.67 mg / g DM).
- the capsaicin concentration of the pepper dried in an oven at 100 ° C. is markedly lower than that of the fresh pepper (43% and 81%, in dry mass equivalent of the fresh pepper, respectively for the Habanero pepper and the red pepper).
- the capsaicin content of the totum resulting from said process in dry mass equivalent of pepper contained in the totum
- the capsaicin content of the totum resulting from said process is almost equivalent to the content of the fresh pepper, i.e. 95% for the Habanero pepper and 99% for the red pepper. .
- Example 6 Microbiological study on the conservation of totum The method described in Example 1 was implemented.
- Example 7 Process implemented from fresh Habanero pepper in glycerol monolaurate with addition of plant material in two stages
- the different stages of the process (with addition of plant material in two times, or the realization of two cycles as illustrated by Figure 2) according to the invention are implemented according to the conditions more particularly defined in Table 5 below.
- the totum thus obtained comprises a water content of the order of 2% and has the appearance of a smooth and homogeneous paste, of dark red color, with a more pronounced color and odor than for the totum obtained according to the example 4 (with addition of chilli pepper at once and carrying out a single cycle).
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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BR112022023492A BR112022023492A2 (pt) | 2020-05-21 | 2021-05-20 | Processo de preparação de um extrato total, extrato total ou filtrado sólido, uso de um extrato total ou filtrado e composição |
US17/999,267 US20230190847A1 (en) | 2020-05-21 | 2021-05-20 | Process for preparing a total extract or a filtrate enabling the stabilization of fresh plant matter |
EP21726315.1A EP4152955A1 (fr) | 2020-05-21 | 2021-05-20 | Procede de preparation d'un totum ou d'un filtrat permettant la stabilisation de matiere vegetale fraiche |
CN202180061307.0A CN116193995A (zh) | 2020-05-21 | 2021-05-20 | 用于制备能够稳定新鲜植物物质的总提取物或滤液的方法 |
Applications Claiming Priority (2)
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FRFR2005403 | 2020-05-21 | ||
FR2005403A FR3110342A1 (fr) | 2020-05-21 | 2020-05-21 | Procédé de préparation d’un totum ou d’un filtrat permettant la stabilisation de matière végétale fraîche |
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WO2021234067A1 true WO2021234067A1 (fr) | 2021-11-25 |
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PCT/EP2021/063412 WO2021234067A1 (fr) | 2020-05-21 | 2021-05-20 | Procede de preparation d'un totum ou d'un filtrat permettant la stabilisation de matiere vegetale fraiche |
Country Status (6)
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US (1) | US20230190847A1 (fr) |
EP (1) | EP4152955A1 (fr) |
CN (1) | CN116193995A (fr) |
BR (1) | BR112022023492A2 (fr) |
FR (1) | FR3110342A1 (fr) |
WO (1) | WO2021234067A1 (fr) |
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EP0639336A1 (fr) * | 1993-08-17 | 1995-02-22 | Societe Des Produits Nestle S.A. | Procédé d'extraction d'antioxydant d'origine végétale sous forme liquide |
US5447735A (en) * | 1994-06-14 | 1995-09-05 | Miller; Van | Sweet cinnamon or other flavored, fat-based, anhydrous flakes for bakery purposes |
WO1995031966A1 (fr) | 1994-05-20 | 1995-11-30 | Novavax, Inc. | Emulsions huile-dans-eau antimicrobiennes |
FR2943684A1 (fr) | 2009-03-30 | 2010-10-01 | Castera Anne Rossignol | Procede d'extraction de composes non volatils. |
FR2986534A1 (fr) * | 2012-02-07 | 2013-08-09 | Univ D Avignon Et Des Pays De Vaucluse | Procede d'enrichissement d'un corps gras en carotenoides |
FR3013979A1 (fr) | 2013-12-02 | 2015-06-05 | Maximaliste Ltd | Composition comprenant des extraits de raisin tannat ou cannoneau, procede d'extraction et utilisations |
WO2016169129A1 (fr) | 2015-04-24 | 2016-10-27 | 浙江大学 | Gel antibactérien à base d'huile comestible contenant de l'huile végétale et son procédé de préparation |
EP3290499A1 (fr) | 2015-04-27 | 2018-03-07 | Fuji Oil Holdings Inc. | Procédé permettant de fabriquer une matière grasse contenant des acides gras polyinsaturés à longue chaîne |
WO2019047004A1 (fr) | 2017-09-05 | 2019-03-14 | 拉芳家化股份有限公司 | Conservateur alternatif naturel d'huile essentielle de plante et application cosmétique de celui-ci |
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Family Cites Families (3)
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AU2002233171A1 (en) * | 2001-02-23 | 2002-09-04 | Aarhus Oliefabrik A/S | A method for treating a solvent-extracted plant residue with a fat |
US8784904B2 (en) * | 2008-04-10 | 2014-07-22 | U.S. Nutraceuticals, LLC | Plant derived seed extract rich in essential fatty acids derived from perilla seed: composition of matter, manufacturing process and use |
FR2966700B1 (fr) * | 2010-10-29 | 2013-01-11 | Bernard Mompon | Procede de fabrication d?articles d?origine vegetale impregnes de substance liquide vegetale |
-
2020
- 2020-05-21 FR FR2005403A patent/FR3110342A1/fr active Pending
-
2021
- 2021-05-20 US US17/999,267 patent/US20230190847A1/en active Pending
- 2021-05-20 WO PCT/EP2021/063412 patent/WO2021234067A1/fr unknown
- 2021-05-20 CN CN202180061307.0A patent/CN116193995A/zh active Pending
- 2021-05-20 BR BR112022023492A patent/BR112022023492A2/pt unknown
- 2021-05-20 EP EP21726315.1A patent/EP4152955A1/fr active Pending
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EP0639336A1 (fr) * | 1993-08-17 | 1995-02-22 | Societe Des Produits Nestle S.A. | Procédé d'extraction d'antioxydant d'origine végétale sous forme liquide |
WO1995031966A1 (fr) | 1994-05-20 | 1995-11-30 | Novavax, Inc. | Emulsions huile-dans-eau antimicrobiennes |
US5447735A (en) * | 1994-06-14 | 1995-09-05 | Miller; Van | Sweet cinnamon or other flavored, fat-based, anhydrous flakes for bakery purposes |
FR2943684A1 (fr) | 2009-03-30 | 2010-10-01 | Castera Anne Rossignol | Procede d'extraction de composes non volatils. |
FR2986534A1 (fr) * | 2012-02-07 | 2013-08-09 | Univ D Avignon Et Des Pays De Vaucluse | Procede d'enrichissement d'un corps gras en carotenoides |
FR3013979A1 (fr) | 2013-12-02 | 2015-06-05 | Maximaliste Ltd | Composition comprenant des extraits de raisin tannat ou cannoneau, procede d'extraction et utilisations |
WO2016169129A1 (fr) | 2015-04-24 | 2016-10-27 | 浙江大学 | Gel antibactérien à base d'huile comestible contenant de l'huile végétale et son procédé de préparation |
EP3290499A1 (fr) | 2015-04-27 | 2018-03-07 | Fuji Oil Holdings Inc. | Procédé permettant de fabriquer une matière grasse contenant des acides gras polyinsaturés à longue chaîne |
WO2019047004A1 (fr) | 2017-09-05 | 2019-03-14 | 拉芳家化股份有限公司 | Conservateur alternatif naturel d'huile essentielle de plante et application cosmétique de celui-ci |
EP3649867A1 (fr) * | 2018-02-22 | 2020-05-13 | Mizkan Holdings Co., Ltd. | Mélange d'un aliment et d'une huile/graisse et son procédé de production |
WO2020008151A1 (fr) * | 2018-07-04 | 2020-01-09 | Laboratoire Mawena | Composition huileuse contenant un extrait de mimosa tenuiflora et utilisations |
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Also Published As
Publication number | Publication date |
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BR112022023492A2 (pt) | 2023-01-17 |
EP4152955A1 (fr) | 2023-03-29 |
US20230190847A1 (en) | 2023-06-22 |
FR3110342A1 (fr) | 2021-11-26 |
CN116193995A (zh) | 2023-05-30 |
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