WO2007051813A2 - Composition de natamycine liquide, procede de preparation, utilisation et produits proteges - Google Patents

Composition de natamycine liquide, procede de preparation, utilisation et produits proteges Download PDF

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Publication number
WO2007051813A2
WO2007051813A2 PCT/EP2006/068027 EP2006068027W WO2007051813A2 WO 2007051813 A2 WO2007051813 A2 WO 2007051813A2 EP 2006068027 W EP2006068027 W EP 2006068027W WO 2007051813 A2 WO2007051813 A2 WO 2007051813A2
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Prior art keywords
natamycin
composition
solvent
water
alcohol
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PCT/EP2006/068027
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English (en)
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WO2007051813A3 (fr
Inventor
Peter Wisler
Jonathon Mallinson
Tania Schellaars
Kersti Haugan
Stephane Constant
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Danisco A/S
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Publication of WO2007051813A2 publication Critical patent/WO2007051813A2/fr
Publication of WO2007051813A3 publication Critical patent/WO2007051813A3/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D15/00—Improving finished, partly finished or par-baked bakery products
    • A21D15/08—Improving finished, partly finished or par-baked bakery products by coating

Definitions

  • Liquid natamycin composition Liquid natamycin composition, process for preparing same, use thereof and protected products
  • the present invention relates to a liquid natamycin composition for protecting perishable goods such as food and feed products, including pet foods and beverages, against the growth of fungi.
  • the composition may be used also on agricultural products such as vegetables, fruits and flower bulbs.
  • the composition of the present invention is physically stable over prolonged periods and it is preferably also microbially stable.
  • the present invention also relates to a process for preparing the physically stable liquid natamycin composition according to the invention and to methods of using the composition for controlling the growth of fungi on perishable goods, such as food and feed products.
  • the invention also relates to products treated with the liquid composition.
  • a preferred treated product comprises a bakery product.
  • Natamycin is a polyene macrolide natural anti-fungal agent produced by fermentation of the bacterium Streptomyces natalensis. Natamycin (previously known as pimaricin) has an extremely effective and selective mode of action against a very broad spectrum of common food spoilage yeasts and moulds with most strains being inhibited by concentrations of 1-15 ppm of natamycin.
  • Natamycin has been used for many years in many countries throughout the world as an authorized preservation treatment, principally for surface treatment of cheeses and certain meat products such as dried sausages. Despite this long-term use, the development of resistant strains has not been reported to date unlike the chemical organic acid sorbate and propionate preservatives for which a number of resistant yeasts and moulds have been detected and reported. Some species of Penicittium mould are even able to degrade and metabolise sorbate.
  • Natamycin has not been reported to have any adverse quality or flavour impact on food products. Natamycin is most soluble at high or low pH but is most stable at neutral pH (Stark, J., and Tan, H. S. 2003. 'Natamycin'. In: Food Preservatives, Second Edition. Eds: N. J. Russell and G. W. Gould. Kluwer Academic/Plenum Publishers.)
  • natamycin A general description of natamycin and its current uses may be found in the above review and in Thomas, L. V. and Delves-Broughton, J. 2003. Natamycin. in: Encyclopedia of Food Sciences and Nutrition. Eds. B. Caballero, L. Trugo and P. Finglas, pp 4109-4115. Elsevier Science Ltd.
  • natamycin In the food industry natamycin is generally used as a suspension in an aqueous solution for the surface treatment of food (i.e. in spraying, dipping or brushing) or dosed as a powder directly into food.
  • the natamycin powder although mixed with excipients such as lactose, is difficult to handle due to its stickiness. Furthermore it causes problems by the dust it generates and it can also adhere to weighing equipment used in the preparation of the treatment liquid.
  • Natamycin is a very attractive antifungal agent for many purposes in the food and feed industry as well as for agricultural products.
  • the physical handling and dosing of natamycin powder is not altogether uncomplicated particularly because of the potency of natamycin at very low concentrations.
  • natamycin is sparingly soluble in aqueous liquids, the undissolved crystals tend to settle at the bottom of treatment or storage vessels. This physical instability of the suspensions requires a frequent mixing of the suspension and/or recirculation of the treatment liquid. Natamycin is highly effective against fungi but its suspensions are vulnerable to the attack of bacteria. In order to prevent bacterial growth, salt is typically added to the liquids. However, the salt is prone to crystallize, thus clogging the nozzles of spraying equipment. The problems relating to the physical instability and bacterial vulnerability of aqueous natamycin liquids has made it difficult to provide ready-to-use liquid suspensions and concentrates of natamycin for the industry to use.
  • EP-Bl-O 678 241 discloses a concentrated aqueous suspension of natamycin, which exhibits chemical, physical and microbial stability.
  • the physical stability relates to a stability calculated in hours. It is provided by a gum based or cellulosic thickening agent which increases the viscosity of the suspension to at least 500 mPa.
  • the aqueous suspension may also include a deflocculating or suspending agent. Although the document mentions the possibility of additionally using glycol or glycerol as suspending agents, there are no examples of such use.
  • the aqueous suspension has a pH lower than 6 to provide microbial stability of at least 14 days.
  • WO-A1-03/101213 discloses an aqueous natamycin composition for treating shredded cheese by spraying.
  • the composition contains a thickener such as xanthan gum for preventing the clogging of the nozzles of the spraying equipment.
  • WO-Al -2004/082407 discloses an aqueous solution of natamycin which is chemically stable despite an increased solubility in the aqueous liquid.
  • the liquid comprises a solubilizer which is preferably a surfactant and which increases the amount of dissolved natamycin to at least 100 ppm.
  • the liquid may contain conventional chelating agents and/or antioxidants.
  • WO-Al -2004/105491 discloses a chemically stable ready-to-use aqueous solution of natamycin which contains a water-miscible solvent and natamycin dissolved in the water and solvent
  • the preferred water-miscible solvent is ethanol, but also other lower alcohols such as methanol, propanol, ethylene glycol propylene glycol and glycerol are mentioned.
  • the natamycin is initially dissolved in a water/solvent mixture containing 10 to 90% solvent and having a high or low pH.
  • the resulting concentrate is then quickly diluted with an aqueous buffer solution to adjust the pH to 5-8 for avoiding chemical degradation of the natamycin.
  • the amount of the solvent is 0.1% to 10% in the final aqueous solution.
  • the examples show an amount of 0.2 or 0.4% ethanol in the ready-to-use aqueous solution.
  • GB-A-I 470 005 discloses a non-aqueous alcohol/acid mixture for treating agricultural products, especially citrus fruits.
  • the natamycin is preferably dissolved in a mixture of ethanol and acetic acid.
  • some other lower alcohols and acids are also shown to be useful.
  • alkanols with 2 or 3 carbon atoms and up to one hydroxy per carbon atom can be used, but there are no examples of any solutions with alkanols having more than one hydroxy group.
  • the combination of alcohol and acid provides the benefit of increasing the solubility of the natamycin so that it can penetrate the peel of the citrus fruit to such an extent that mould growth is effectively prevented.
  • the solution may also contain water and it is applied on the agricultural products by submersion, brushing or spraying.
  • WO-Al -2005/074690 discloses a fine bakery product with increased shelf life.
  • the baked product has natamycin sprayed on its outer surface to prevent mould growth in a package stored for 2 weeks or more.
  • the natamycin is preferably sprayed in the form of an aqueous suspension with or without a thickener.
  • the present invention seeks to overcome the problems of the prior art, as described above, by providing a liquid composition of natamycin in an organic solvent. Contrary to the prior art, the composition is not an aqueous liquid.
  • the present inventors have found that lower polyhydric alcohols and especially glycerol have unique properties, which make them eminently suitable for providing a stable natamycin composition.
  • the organic solvent and the absence of large amounts of water help to make the natamycin composition stable against bacterial degradation.
  • the invention also relates to a process for preparing the physically stable liquid natamycin composition.
  • the process comprises combining an antifungally effective mount of natamycin with a physically stabilizing amount of polyhydric alcohol(s) in an alcoholic solvent selected from polyhydric alcohols, mixtures of polyhydric alcohols and mixtures of polyhydric and monohydric alcohols, and mixing the resulting natamycin-solvent mixture to provide a physically stable solution, sol or suspension of natamycin in said solvent.
  • the invention further relates to the use of the liquid natamycin composition for controlling the growth of fungi.
  • the use comprises applying an antifungally effective amount of natamycin to perishable product(s) said natamycin being provided by way of a liquid composition comprising natamycin in said alcoholic solvent, wherein said solvent contains a physically stabilizing amount of polyhydric alcohol(s) and is selected from polyhydric alcohols, mixtures of polyhydric alcohols and mixtures of polyhydric and monohydric alcohols.
  • the composition is a physically stable solution, sol or suspension of natamycin in said solvent.
  • the invention also relates to products treated with the composition according to the invention.
  • Said products comprise antifungally preserved products, which are food or feed products or agricultural products having natamycin and polyhydric alcohol spread over the surface thereof, said natamycin being provided in an antifungally effective amount for preserving said product against the growth of fungi.
  • the polyhydric alcohol used as physically stabilizing solvent in the composition according to the invention contains 2 or 3 carbon atoms and is selected from glycerol, propylene glycol and glycol. Glycerol is the preferred polyhydric alcohol.
  • the monohydric alcohol in the alcoholic solvent also contains 2 or 3 carbon atoms and is selected from ethanol and propanol. Ethanol is the preferred monohydric alcohol.
  • the alcoholic solvent of the liquid composition preferably consists essentially only of said alcohol(s) and the innate water included in said alcohol(s).
  • alcohol means an organic compound having at least one hydroxy group.
  • a "monohydric alcohol” has only one hydroxy group, while a “polyhydric alcohol” has at least two hydroxy groups.
  • the preferred alcohols of the present invention are lower alcohols having 2 or 3 carbon atoms. It is noted that the monohydric alcohol methanol would be technically suitable for use in the invention but it is usually excluded because of its poisonous character.
  • the term "physical stability” or “physically stable” refers to a liquid natamycin composition wherein the natamycin is included in such a form that any tendency to settle out is so small that the liquid retains a uniform distribution of the natamycin during the practical daily use of the liquid.
  • a physical stability of four days means, for instance, that even though the liquid is not agitated, shaken or mixed for four days it remains uniform enough for practical purposes.
  • a “physically stabilizing amount” of polyhydric alcohol is an amount which is sufficient to keep the solution, suspension or sol uniform for the practical use of the liquid without the conventional mixing, agitation or recycling. The amount differs from one polyhydric alcohol to another and is also different depending on the other alcohols included and on the content of water and other components in the composition.
  • the stabilizing amount of polyhydric alcohol is preferably one which keeps the composition physically stable for at least 2 weeks.
  • food and feed products means products, which are meant to be ingested by man or beast.
  • the term food specifically includes also pet foods and beverages.
  • the food and feed products of the invention are solid, semi-solid or liquid products, although the preferred products are solid.
  • the term "agricultural products” means fruits, vegetables, crops, flower bulbs and other agricultural products, which are susceptible to attack by fungi.
  • the food and feed products as well as the agricultural products are also referred to as “perishable products”.
  • the preferred polyhydric alcohol according to the invention is glycerol.
  • Propylene glycol has also proven very useful.
  • the solvent preferably contains at least 50%, preferably at least 70% polyhydric alcohol. Most preferably, the solvent contains at least 80% polyhydric alcohol. The solvent may contain 90% or even 100% polyhydric alcohol. It is preferred to use glycerol in an amount of at least 30% and preferably at least 45 % of the solvent. It should be noted that very good results have been obtained with the use of glycerol as the only alcohol of the solvent.
  • the preferred monohydric alcohol in the solvent is ethanol. If propanol is used, the propanol may be n-propanol or i-propanol. The preferred propanol is i-propanol.
  • the preferred solvent of the invention is a mixture of glycerol and a second alcohol selected from propylene glycol and ethanol. Mixtures of glycerol, propylene glycol and ethanol are also very good solvents.
  • the alcoholic solvent may contain minor amounts of other solvent components in addition to the alcoholic solvents. However, it is preferred that the solvent consists essentially of said alcohols. It should be noted that ethanol, for instance, usually contains minor amounts of water (about 5% to 0.5%) and also glycerol contains some innate water (about 0.2%). This small amount of water need not be removed before use in the composition and the low water content is not considered to make the liquid composition an aqueous one.
  • the natamycin is dissolved or suspended in the solvent. Even when the natamycin is not completely dissolved, the solvent is capable of keeping the natamycin uniformly distributed in the liquid. Natamycin can also form a sol in the polyhydric alcohol or mixture of alcohols. In the sol the natamycin particles are so small that no sedimentation takes place even during weeks of storage.
  • the invention provides a physically stable liquid form of natamycin with no precipitation or settling of the natamycin for a prolonged period of time. This gives the advantage of ease of handling with no need for stirring, agitating, shaking or recirculation of the liquid before or during use.
  • composition of the invention is useful as such for application to perishable goods.
  • the composition may be incorporated into the goods or applied by dipping, spraying or brushing onto the goods.
  • the solvent comprises a mixture of glycerol and ethanol, wherein the ratio of glycerol to ethanol is from 95:5 to 70:30, preferably from 90:10 to 80:20 calculated by weight.
  • Addition of ethanol to the glycerol improves the solubility of natamycin in the solvent and reduces the viscosity of the composition. It is preferred that at least 30%, preferably at least 45% by weight of the solvent comprises glycerol.
  • the amount of ethanol should not exceed 30% by weight of the liquid composition. Preferably, the ethanol amount is between 10 and 20% by weight.
  • the composition of the present invention differs from the traditional aqueous liquids used on food and feed products in that it is non-aqueous.
  • the preferred non-aqueous composition comprises less than 10% water, preferably less than 5% water, most preferably less than 2% water. When water- free solvents are used, the liquid composition is essentially free of water.
  • the water content of the liquid composition of the invention is preferably very low.
  • Natamycin is sparingly soluble in water and adding e.g. 20% water to a concentrate of natamycin in glycerol makes the natamycin drop out.
  • the water destroys the physical stability provided by the polyhydric alcohol. Smaller amounts of water are acceptable and the composition remains stable even though 10% water is added to it.
  • the innate water provided e.g. by the use of ethanol having 5% water is not harmful to the stability.
  • the low water content provides a low water activity to the composition and hence most bacteria are unable to grow in the liquid. This makes the composition microbially stable even when stored at ambient temperature.
  • the alcohols of the solvent do not support the growth of bacteria on their own, which adds to the microbial stability.
  • the long shelf life of the composition provides great advantages over the traditional physically and microbially unstable aqueous natamycin preparations. Because of the microbial stability, the composition can be made without salt, which reduces corrosion and clogging of spray nozzles.
  • natamycin When natamycin is added to food and feed products without water or with only minor amounts of water, this removes concerns connected with additional moisture in the production environment and on the food or feed surface.
  • the liquid composition contains an antifungally effective amount of natamycin.
  • the amount of natamycin included depends on the intended use of the liquid composition. However, the composition typically includes 100 to 50,000 ppm natamycin. If less than 100 ppm natamycin is included, the amount of liquid applied to the goods will have to be larger than normally desired. It is preferred that when the composition is to be used as a ready-to-use non-aqueous microbially stable natamycin liquid, the natamycin is present in an amount of 100 to 10,000 ppm.
  • the alcoholic solvent of the present invention is capable of forming a homogeneous liquid with water and with many other solvents. The composition is therefore suitable as a concentrate to be diluted before use. Thus, if the composition is a non-aqueous liquid concentrate, the natamycin should be present in an amount of 400 to 50,000 ppm to allow for a dilution with 4 to 5 times the amount of water or solvent.
  • natamycin typically needed for providing an antifungally effective ready-to-use composition is soluble in a mixture of glycerol and ethanol and it forms a true solution in the solvent. Hence the natamycin will not separate out on standing. Natamycin is also soluble in a mixture of glycerol and propylene glycol. In glycerol natamycin forms a suspension or sol, which is also physically stable.
  • the liquid composition of the invention is adapted for being applied to perishable products as such or after dilution with water or another physiologically acceptable (food grade) liquid.
  • the composition is preferably applied onto the surface of an edible food or feed product.
  • the application of the composition on the products may be performed by dipping, brushing or spraying.
  • the liquid is adapted for being added directly into a liquid or semi-liquid food product such as various beverages or drinks.
  • the liquid natamycin composition according to the invention may comprise other active agents besides natamycin.
  • Such additive ingredients may have an effect on the liquid composition as such or on a diluted form thereof.
  • the additive may also be desirable in and/or on the product to be treated with the composition.
  • the additive may also be an active agent for the natamycin itself or for another additive ingredient. Since the composition of the present invention is nonaqueous it is advantageous to include in the liquid such additives, which are not soluble in water but are soluble in the alcoholic solvent. Other additives are soluble in both the alcoholic solvent and in water. Some are soluble only in water and play their role after dilution with water has been completed.
  • the additive may be included in the ready-to-use liquid composition or in the concentrate or it may be added via a diluent for the concentrate.
  • Such additives include, but are not limited to preservatives, stabilizers, thickeners, antioxidants, chelating agents, buffers, acids, salts, carriers, excipients, diluents, surfactants, emulsifiers, flavonoids, vitamins, essential oils, flavours, pigments and mixtures thereof.
  • the additives should not be used in amounts, which impair the physical stability of the composition.
  • An organic acid should not either be included in the composition in such a manner that the organic acid in combination with the alcohol in the solvent makes the natamycin penetrate the peel or wall of agricultural products such as citrus fruit (as described in GB -A-I 470 005).
  • the composition of the invention When the composition of the invention is applied to the outer surface of food products, the composition should rather maintain the natamycin on the surface or as close to the surface as possible, because that is where the attacking moulds and yeasts will be. Food products, which have undergone a heating process will be substantially free of moulds and yeast underneath their outer crust or wall and any natamycin migrating into the product will be lost for its protective purpose. This is especially true for products with a fairly easily penetrable wall or crust, such as a bakery product.
  • Polyhydric alcohols, and especially glycerol have a viscosity, which is eminently suitable for keeping the composition on the surface of the product.
  • organic acids should be excluded and, if preservation is needed, preservatives other than organic acids should be selected.
  • the active agent(s) is/are selected from phenolic and alkyl compounds, flavonoids and mixtures thereof.
  • the active agent may also be selected from plant extracts or essential oils, such as obtainable from cinnamon, vanilla, citrus, geranium species, mint, cloves, thyme, garlic, onion, horseradish, mustard, cole, cabbage, spinach, radish, oreganum, sage, grapes and other red fruits, coffee, tea, rosemary, and mixtures thereof.
  • Other alcohol soluble additives are selected from vegetables oils containing vitamin A, vitamin E, vitamin B3 (nicotinamide) and/or tocopherol. Many of these compounds have an antibiotic, antibacterial or antimycotic activity and have a preservative effect on the natamycin composition as well as on the treated product itself.
  • anti-oxidants such as butyl hydroxy anisole, butyl hydroxy toluene, tert butyl hydroxy quinine, propyl gallate and mixtures thereof.
  • composition or its diluent may also contain chelating agents such as EDTA, citric acid, tartaric acid, etc.
  • composition or its diluent may contain active agents selected from fatty acids esters such as mono-and diglycerides, non-ionic surfactants such as polysorbates, phospholipids, etc.
  • Emulsifiers may enhance the stability of the composition, especially after dilution.
  • the composition comprises a concentrate and the concentrate or the diluent therefor contains active agent(s), which have the function of stabilizer, thickener and/or solubilizer after dilution of the concentrate.
  • active agent(s) which have the function of stabilizer, thickener and/or solubilizer after dilution of the concentrate.
  • stabilizers, thickeners and solubilizers are known in the art and they include but are not limited to gums and other hydrocolloids, such as xanthan gum, guar gum, etc.
  • the natamycin dissolved or suspended in the alcoholic solvent of the present invention has a surprisingly good physical stability. It retains its physical stability for 2 weeks or more without the addition of further stabilizers. Test samples have shown no drop out of natamycin even after a storage of 10 weeks at ambient temperature.
  • the liquid natamycin composition of the present invention is easy to prepare.
  • the desired amount of natamycin is weighed and added to the alcoholic solvent. If the alcoholic solvent is a mixture of alcohols, the mixed solvent is typically prepared beforehand by simply mixing the alcohols together. In case the composition is to be applied to edible products, the ingredients need all be food grade ingredients.
  • the natamycin is typically used in one of its commercial forms, such as Natamax® (from Danisco), Delvocid® (from DSM), etc.
  • the natamycin may contain additives and excipients such as salt and lactose, in which case these will be included in the composition.
  • the only water which is added into the composition is the innate water of the components of the composition.
  • active agents besides natamycin may be added to the composition before or after the natamycin or with the natamycin.
  • they may be added to the solvent, to the natamycin, to the composition or to a diluent therefor. They may be first dissolved in a solvent alcohol such as in ethanol or, if water soluble, they may be dissolved in a small amount of water. They may also be suspended as fine particles in the composition.
  • the viscosity of the liquid composition can be adjusted by selecting the alcohol and/or by adding thickeners.
  • the viscosity can be adjusted to a value between 0.0001 Pas and 10 Pas.
  • the viscosity when glycerol alone is used as the solvent is 5 to 10 Pas. Adding ethanol reduces the viscosity, which thus can be lowered down to 0.0001 Pas if desired.
  • the liquid composition as such is thus suitable for spraying on products.
  • natamycin liquid with such a low viscosity and good physical and microbial stability.
  • This combination provides an advantage especially for spraying applications.
  • an antifungally effective amount of natamycin is applied to perishable product(s) together with the alcoholic solvent.
  • the liquid composition may be used as such or it may comprise a concentrate to be diluted with a diluent selected from water and an alcoholic diluent comprising glycerol, propylene glycol, glycol, ethanol, propanol or mixtures thereof prior to being applied to said product(s).
  • a diluent selected from water and an alcoholic diluent comprising glycerol, propylene glycol, glycol, ethanol, propanol or mixtures thereof prior to being applied to said product(s).
  • a diluent selected from water and an alcoholic diluent comprising glycerol, propylene glycol, glycol, ethanol, propanol or mixtures
  • the composition of the invention When the composition of the invention is prepared in the form of a concentrate, it is typically diluted with water prior to use. This reduces the need for storing and shipping of huge amounts of water. Diluting with water is also easy at the point of end use.
  • the concentrate is diluted with no more than 4 times the amount of water. If another diluent is used, especially if an alcoholic solvent is used for dilution, the concentrate is typically diluted with no more than 5 times the amount of said alcoholic diluent.
  • the physical stability of the composition is reduced when it is diluted with water.
  • a dilution with about 20% water makes the natamycin drop out too quickly for most practical use, while a dilution with water in ratios of water to concentrate between 2:1 and 4:1 maintains the liquid physically stable for 0.5 to 2 hours even without a stabilizer.
  • the diluted composition when the composition is diluted with water, the diluted composition preferably contains a compound selected from a stabilizer, an emulsifier, an antioxidant, a chelating agent, a thickener, a surfactant, a preservative and combinations thereof.
  • the compound(s) should preferably be selected from compounds capable of maintaining the diluted composition physically and/or microbially stable for at least 4 days.
  • the concentrate is preferably made of natamycin in a mixture of glycerol and ethanol.
  • the above mentioned additives may be included in the concentrate or in the diluent.
  • the concentrate is diluted with water immediately before application, e.g. by injecting water into the concentrate flowing to or in the spray equipment. In such a case no stabilizers or preservatives are needed.
  • the liquid natamycin composition is applied to the products to be treated in a manner well known in the art. Such application procedures include spraying, dipping or brushing. Spraying is the preferred way of application since the viscosity of the liquid is especially suited for such use.
  • the spraying may be performed with the concentrated liquid as such or the composition may be sprayed after dilution with water or another diluent.
  • the preferred products to be sprayed are baked or unbaked bakery product. Special benefits are obtained in the spraying of baked bread, hot plate goods or fine bakery.
  • Bread products include different kinds of bread which are typically packaged in moisture proof casings and are expected to have a shelf life of 5 days or more.
  • a preferred kind of bread is sliced loaves packed in plastic bags.
  • Hot plate goods include crumpets and pancakes and fine bakery includes all kinds of cakes and pastry, including buns, waffles, tortillas, pizzas, etc.
  • the viscosity of the liquid enables the production of a very fine spray and the natamycin is evenly distributed over the whole product surface.
  • the monohydric alcohol such as ethanol will evaporate during spraying and after having landed on the product.
  • the product contains only the natamycin (and other active agents) and the polyhydric alcohol component.
  • a ready-to-use natamycin composition was prepared as follows:
  • Ethanol (95%, 10 g) was mixed with glycerol (89.6 g) to provide an alcoholic solvent mixture.
  • glycerol 89.6 g
  • Natamax® natamycin provided from Danisco A/S and containing 50 % lactose as a diluent
  • the natamycin was readily soluble in the solvent after a few minutes mixing.
  • the natamycin seemed to form a true solution in the glycerol/ethanol solvent.
  • the liquid composition was completely stable and natamycin did not separate out on standing. After 10 weeks of storage, no separation of the natamycin from the solution could be seen. There was no microbial growth in the composition during the storage.
  • Ethanol was also added in higher concentration (up to 30%) to the solvent mixture to reduce the viscosity.
  • concentration up to 30%
  • the solution with 30% ethanol was very easy to spray.
  • a clear smell of ethanol was noted during spraying.
  • Increasing the ethanol content further would reduce the viscosity still further, but the handling of liquids with more than 30% ethanol poses certain hazards, wherefore higher ethanol amounts should be avoided.
  • a ready-to-use natamycin composition was prepared as follows:
  • alcoholic solvent was made by combining propylene glycol and glycerol. Natamycin in the form of Natamax® (from Danisco A/S) was added to the solvent to provide a 200 ppm natamycin liquid composition having the following components (by weight)
  • the Natamax® dissolved in the solvent mixture with a couple of hours of mixing.
  • the propylene glycol lowered the viscosity of the glycerol solvent and the composition was suitable for spraying.
  • the absence of ethanol reduced the volatility of the solvent and eliminated any potential hazards.
  • the solution was stored for 10 weeks without any settling and without microbial growth.
  • a liquid non-aqueous natamycin concentrate was made as follows:
  • Natamycin in the form of Natamax SF (from Danisco A/S, no lactose diluent included) was added to glycerol to make a mixture having 1200 ppm of natamycin and the following components (by weight):
  • the concentrate was diluted with water.
  • the dilution water contained 0.1 % of a stabilizer (50% xanthan gum and 50% guar gum) and 0.5% salt (NaCl). 1 part of the concentrate was diluted with 2 parts of water. The diluted concentrate remained physically stable for more than 10 weeks.
  • Bread loaves were baked by normal procedures.
  • the main ingredients were flour, sugar, salt, shortening, dry yeast and water.
  • Directly after baking the loaves were detinned and then sprayed with the natamycin compositions of examples 1 and 2, respectively.
  • the amount of natamycin on the surface of the loaves was analysed and was found to be about 1.5 ⁇ g/cm 2 . No natamycin was detected in any sample below the 3 mm depth that was analysed, which indicates that the natamycin composition did not migrate past the crust.
  • the loaves were sliced and packed in plastic bags after cooling.
  • the bags were stored at ambient conditions (22-24 0 C, relative humidity 66%) for 12 days. Bags with untreated loaves were stored in the same manner as controls.
  • control loaves After 4 days, the control loaves showed clear growth of mould and were wholly covered by mould mycelium on day 12.
  • the loaves treated with the natamycin compositions kept mould-free for 11 days. On day 12 small colonies of mould were seen on the crust of some of the loaves.

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  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Food Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)

Abstract

L'invention concerne une composition de natamycine liquide permettant de protéger des aliments périssables, tels que des produits alimentaires, des produits pour l'alimentation des animaux et des produits agricoles. Ladite composition comprend une quantité antifongiquement efficace de natamycine dans un solvant alcoolique. Ledit solvant contient une quantité de stabilisation physique d'alcool(s) polyhydrique(s) et est sélectionné dans le groupe constitué par les alcools polyhydriques, des mélanges d'alcools polyhydriques et des mélanges d'alcools polyhydrique et monohydrique. La composition comprend une solution physiquement stable, un sel ou une suspension de natamycine dans le solvant alcoolique. La quantité d'eau est de préférence limitée à l'eau présente dans le ou les alcool(s). L'invention concerne également un procédé permettant de préparer la composition par mélange de composants et d'utiliser ladite composition sous forme diluée, notamment, en pulvérisation sur un produit de boulangerie. L'invention concerne enfin les produits traités par la natamycine.
PCT/EP2006/068027 2005-11-02 2006-11-02 Composition de natamycine liquide, procede de preparation, utilisation et produits proteges WO2007051813A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI20055588A FI20055588L (fi) 2005-11-02 2005-11-02 Nestemäinen natamysiinikoostumus, menetelmä sen valmistamiseksi, sen käyttö ja suojatut tuotteet
FI20055588 2005-11-02

Publications (2)

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WO2007051813A2 true WO2007051813A2 (fr) 2007-05-10
WO2007051813A3 WO2007051813A3 (fr) 2007-10-25

Family

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Country Status (2)

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FI (1) FI20055588L (fr)
WO (1) WO2007051813A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9907811B2 (en) * 2015-03-19 2018-03-06 Valent Biosciences Corporation Concentrated natamycin suspension formulations
WO2019154888A1 (fr) 2018-02-08 2019-08-15 Dsm Ip Assets B.V. Natamycine pour la conservation d'un produit cuit
WO2019154887A1 (fr) 2018-02-08 2019-08-15 Dsm Ip Assets B.V. Solution comprenant de la natamycine
CN114208874A (zh) * 2021-11-12 2022-03-22 山东福瑞达生物科技有限公司 一种油溶型纳他霉素制剂及其制备方法和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2150453A1 (fr) * 1993-09-29 1995-04-06 Ferdinand Theodorus Joseph Van Rijn Nouvelle composition antifongique
WO2004105491A1 (fr) * 2003-06-02 2004-12-09 Dsm Ip Assets B.V. Solution aqueuse stable d'un fongicide a base de natamycine
US20050163895A1 (en) * 2004-01-28 2005-07-28 Graham Williams Baked product with increased shelf life and process for increasing the shelf life of baked products

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9907811B2 (en) * 2015-03-19 2018-03-06 Valent Biosciences Corporation Concentrated natamycin suspension formulations
WO2019154888A1 (fr) 2018-02-08 2019-08-15 Dsm Ip Assets B.V. Natamycine pour la conservation d'un produit cuit
WO2019154887A1 (fr) 2018-02-08 2019-08-15 Dsm Ip Assets B.V. Solution comprenant de la natamycine
CN114208874A (zh) * 2021-11-12 2022-03-22 山东福瑞达生物科技有限公司 一种油溶型纳他霉素制剂及其制备方法和应用

Also Published As

Publication number Publication date
WO2007051813A3 (fr) 2007-10-25
FI20055588A7 (fi) 2007-05-03
FI20055588L (fi) 2007-05-03
FI20055588A0 (fi) 2005-11-02

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