EP1227723A2 - Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent - Google Patents

Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent

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Publication number
EP1227723A2
EP1227723A2 EP00980091A EP00980091A EP1227723A2 EP 1227723 A2 EP1227723 A2 EP 1227723A2 EP 00980091 A EP00980091 A EP 00980091A EP 00980091 A EP00980091 A EP 00980091A EP 1227723 A2 EP1227723 A2 EP 1227723A2
Authority
EP
European Patent Office
Prior art keywords
nonanoic acid
food
cheese
ppm
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00980091A
Other languages
German (de)
English (en)
French (fr)
Inventor
P.M.F.J. Koenraad
Annemarie Frederike Braber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stichting Nederlands Instituut Voor Zuivelonderzoek
Stichting Nederlands Instituut Voor Zuivelonderzoek (Nizo)
Original Assignee
Stichting Nederlands Instituut Voor Zuivelonderzoek
Stichting Nederlands Instituut Voor Zuivelonderzoek (Nizo)
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Filing date
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Application filed by Stichting Nederlands Instituut Voor Zuivelonderzoek, Stichting Nederlands Instituut Voor Zuivelonderzoek (Nizo) filed Critical Stichting Nederlands Instituut Voor Zuivelonderzoek
Publication of EP1227723A2 publication Critical patent/EP1227723A2/en
Withdrawn legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B11/00Preservation of milk or dairy products
    • A23B11/60Preservation of cheese or cheese preparations
    • A23B11/65Preservation of cheese or cheese preparations by addition of preservatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00Preservation of foods or foodstuffs, in general
    • A23B2/70Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729Organic compounds; Microorganisms; Enzymes
    • A23B2/742Organic compounds containing oxygen
    • A23B2/754Organic compounds containing oxygen containing carboxyl groups
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B7/00Preservation of fruit or vegetables; Chemical ripening of fruit or vegetables
    • A23B7/10Preserving with acids; Acid fermentation
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/12Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof

Definitions

  • nonanoic acid as an antimicrobial agent, in particular an antifungal agent
  • the present invention relates to the use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent. More particularly, the invention relates to the use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent, in foods and in particular in dairy products such as cheese and products based on fruit, such as fruit juices.
  • the invention furthermore relates to foods which contain nonanoic acid as an antimicrobial agent.
  • Particular aspects of the invention lie in the use of nonanoic acid in (solutions or suspensions for) cheese coatings, in the nonanoic acid-containing cheese coatings thus obtained and in the cheeses coated with these nonanoic acid-containing coatings.
  • nonanoic acid in food products is known.
  • it is used as a synthetic flavouring in, for example, non-alcoholic drinks, ice cream, confectionery, gelatine, milk puddings and bakery products.
  • US Patent 2 154 449 describes the antifungal properties of C 3 - C I2 carboxylic acids and salts thereof, in particular the incorporation of calcium propionate in bread dough in order to prevent the formation of mould on bread.
  • European Patent Application EP 0 244 144 A 1 teaches the addition of glyceryl fatty acid esters in combination with one or more C 6 .C, 8 carboxylic acids as preservatives to, inter alia, food compositions.
  • WO 96/29895 describes a method for improving the shelf/storage life of perishable products by treating surfaces, equipment and materials, which come into contact with the products during the processing thereof, with an antimicrobial aromatic compound.
  • WO 96/29895 states that fatty acids, including nonanoic acid, can also be used in combination with the aromatic compound.
  • European Patent Application EP 0 465 423 describes antimicrobial pharmaceutical preparations containing C 4 - C, 4 carboxylic acids.
  • US Patent 4 406 884 describes antimicrobial pharmaceutical preparations for topical use which contain C 5 - C, 2 carboxylic acids.
  • US Patent 3 931 413 teaches the treatment of plants with C 6 - C, 8 carboxylic acids to combat infections by moulds which overwinter in the buds of the plants.
  • Nonanoic acid is also used in some meat products to adjust the acidity. For instance,
  • US Patent 4 495 208 describes a dog or cat food with good storage/shelf life which has a high moisture content (A w > 0.9 and a water content of 50 - 80 %) that contains 4 -15 % (m/m) fructose, 0.3 - 3.0 % (m/m) of an edible organic acid, sufficient inorganic acid to obtain a pH in the range of 3.5 - 5.8 and an antifungal agent.
  • the organic acid is preferably chosen from heptanoic acid, octanoic acid, nonanoic acid or a combination thereof.
  • US Patent 3 985 904 describes a food based on meat which has a high moisture content and is suitable for human consumption or as an animal feed.
  • This food has a moisture content of at least approximately 50 % (m m) and a water activity A,,, of at least approximately 0.90 and contains more than 50 % (m/m) of a ground, boiled, protein-like chicken, fish or meat material.
  • the edible organic acid is incorporated in this food in an amount which is sufficient to bring the pH of the food to a value in the range from 3.9 to 5.5.
  • US-A 3 985 904 mentions various suitable edible acids in column 6, nonanoic acid is not explicitly mentioned here.
  • the antifungal agent is chosen from benzoates, propionates and sorbate salts.
  • EP-A 0 876 768 describes the use of fatty acid monoesters of polyglycerol to improve the storage/shelf life of foods.
  • the fatty acid radicals can be chosen from caproic acid, caprylic acid, lauric acid or myristic acid.
  • nonanoic acid in herbicidal compositions for agricultural use is described, inter alia, in US Patents 5 098 467, 5 035 741, 5 106 410 and 5 975 4110.
  • US Patents 4 820 438, 5 330 769 and 5 391 379 describe the use of nonanoic acid in soap and cleaning agents.
  • natamycin is used as antifungal agent in cheese making.
  • This compound which is also designated pimaricin or "antibiotic A5283" and is marketed under the trade names Delvocid® and Natamax® (inter alia), is a metabolic product of Streptomyces natalensis and S. chattanoogensis.
  • natamycin has a number of disadvantages. For instance it is fairly expensive. Moreover, it has been found that the mould Penicillium discolor is able to grow on (the surfaces of) cheeses treated with natamycin. This is particularly disadvantageous in the cheese industry, since P. discolor is widespread in cheese warehouses.
  • nonanoic acid displays an antimicrobial action, in particular an antifungal action, especially when it is used in amounts which can suitably be incorporated in food products. More particularly, it has been found that nonanoic acid can advantageously be used as an antimicrobial agent, in particular antifungal (fungicidal) agent, in dairy products such as cheese and products based on fruit, such as fruit juices.
  • nonanoic acid found according to the invention is partly surprising because it is known that some types of mould (such as Aspergillus niger, Synchephalastrum racemosus, Geotrichum candidum, Penicillium expansum, Rhizopus stolonifer and Mucor plombus) naturally produce nonanoic acid.
  • nonanoic acid is also able to inhibit the development of yeasts, which can likewise arise in cheese warehouses.
  • the invention therefore relates to the use of nonanoic acid (n-octane- 1 -carboxylic acid, pelargonic acid, n-nonylic acid) as an antimicrobial agent, in particular antifungal agent (additive) in or for foods and/or other products which have to be protected against perishing caused by microorganisms.
  • nonanoic acid n-octane- 1 -carboxylic acid, pelargonic acid, n-nonylic acid
  • antifungal agent additive
  • the invention also relates to the use of salts of nonanoic acid as an antimicrobial agent.
  • the invention further relates to foods which contain nonanoic acid as an antimicrobial agent, in particular antifungal agent.
  • the food can be any substance that is suitable for consumption by humans or animals, in particular for human consumption, and can be either a ready-to-eat food product or a constituent that can be incorporated in or processed to give a food product.
  • the food or food product is in particular a product or substance that is susceptible to perishing caused by microorganisms, including bacteria, yeasts and in particular moulds (that is to say when no antimicrobial agent is added), such as, for example, a substance or product which will keep for between a few days and a few weeks (for example from 3 days to 3 weeks) under the customary conditions for storage of the product, such as a temperature in the range from room temperature (20 - 25 °C) down to refrigerator temperature (approximately 4 °C).
  • the invention is not restricted to these.
  • the nonanoic acid is used to inhibit microbial growth, in particular the formation of mould, and thus to extend the storage/shelf life.
  • microbial growth can be retarded by the use of nonanoic acid.
  • the degree of retardation will be dependent on, inter alia, the food, the nonanoic acid concentration, the conditions under which the food is stored (temperature, atmospheric humidity), the types of microorganisms to which the food is exposed and the degree of loading.
  • the mould formation i.e.
  • the point in time at which the first growth of mould is discernible to the naked eye will in general be delayed by at least one day, preferably at least 5 - 7 days, that is to say at the temperature at which foods are usually stored - usually room temperature (20 °C) or in the refrigerator (4 °C) - compared with the untreated food.
  • the first discernible formation of mould was postponed from 60 to 67 days.
  • “inhibiting mould formation” and/or “antifungal” is preferably also understood to mean that the development of yeasts is (also) inhibited.
  • nonanoic acid also has an antibacterial action, for example against bacteria which cause food to perish or otherwise reduce the quality thereof, and or against pathogens such as Listeria, Legionella, Salmonella and E.coli O157, Staphylococcus.
  • the food can be a solid, semi-solid or fluid food and can be a fermented or non- fermented food.
  • nonanoic acid can be used according to the invention as an antimicrobial agent, in particular antifungal agent, are: - ready-to-eat food products, including dough products such as pre-baked bread, noodles, pasta, soups and the like; fish and meat products such as sausage, and products based on vegetables or fruit, such as fruit juices and canned fruit or combinations of fruit (juices) with dairy products; flour; nuts and (dried) southern fruits; and also products such as pre-prepared meals, diet foods, complete foods and baby food; foods and constituents for further processing, such as mayonnaise, ketchup and similar sauces; jam, marmalade and similar fruit preparations; and the like.
  • nonanoic acid can also be used outside the food sector as an antimicrobial agent, in particular antifungal and/or antibacterial agent, and examples of this will be given below.
  • nonanoic acid or a nonanoic acid-containing coating to improve the storage/shelf life of fruit such as oranges, lemons, grapefruit, apples, pears and also nuts and (dried) southern fruits, coffee, tea, tobacco and the like, in particular before or during transport and/or during long-term storage, for example in a warehouse or a fruit store (which may or may not be air- conditioned).
  • the nonanoic acid When used as an antifungal agent according to the invention, the nonanoic acid will be used in an amount effective for the inhibition of moulds, yeasts and bacteria, which as a rule will be between 1 and 10,000 mg nonanoic acid per kg food, in particular 10-1,000 mg nonanoic acid per kg food and more particularly 100-500 mg nonanoic acid per kg food.
  • nonanoic acid can be used in yoghurt in an amount of approximately 200 milligram (mg) nonanoic acid per kilogram (kg) yoghurt.
  • the lower limit for the effective amount of nonanoic acid will preferably be chosen from the series 10, 25, 50 or 100 mg nonanoic acid per kg food, whilst the upper limit is preferably chosen from the series 10,000, 5,000, 2,500, or 1,000 mg nonanoic acid per kg food.
  • these amounts are based on the water content of the food.
  • 80 % of the abovementioned amounts of nonanoic acid can also be added per kg food.
  • the precise amount of nonanoic acid will, however, be dependent on the intended food and the way in which the nonanoic acid is used in the food.
  • the nonanoic acid can be uniformly distributed throughout the entire food but, for example - especially in the case of solid or semi-solid foods - can also be present essentially only on or near the surface of the food, for example in the form of a nonanoic acid-containing antimicrobial, in particular antifungal, coating or surface layer, or as a result of treatment of the surface of the food with nonanoic acid.
  • concentration of nonanoic acid, based on the complete food can be low (that is to say lower than the amounts indicated above), provided that sufficient nonanoic acid is present at or close to the surface in order to achieve the desired antimicrobial, in particular antifungal, action.
  • nonanoic acid in amounts of 10 - 10,000 ppm, in particular 100 - 2,000 ppm - i.e. locally or uniformly throughout the entire food - will be adequate to obtain the desired antimicrobial, in particular antifungal, action.
  • concentrations of nonanoic acid - i.e. locally or uniformly throughout the entire food - will as a rule be sufficient to inhibit and/or to prevent the growth of yeast and/or of bacteria.
  • the food product is a dairy product, which in general is defined as a food based on milk or constituents of milk, in particular based on cows milk or constituents thereof.
  • the dairy product is in particular a fermented dairy product that can be solid, semi- solid or fluid.
  • a few non-limiting examples are cheese, butter, cream, yoghurt or yoghurt products (for example yoghurt drinks, such as, for example, milk/fruit juice drinks), cottage cheese, kefir, milk puddings and the like.
  • the invention can also be employed in food products in which such dairy products have been incorporated/processed, such as sauces, pastries, desserts, foods (including complete food and baby food), snacks (for example containing cheese), meat products (such as ham in which proteins have been incorporated), powdered milk and coffee whiteners, and the like.
  • dairy products such as sauces, pastries, desserts, foods (including complete food and baby food), snacks (for example containing cheese), meat products (such as ham in which proteins have been incorporated), powdered milk and coffee whiteners, and the like.
  • the fermented dairy product preferably has a pH of 3.5 to 5.5, for example in the range of 5.1 - 5.5 for cheese and of 3.9 - 4.4 for yoghurt.
  • a pH of 3.5 to 5.5 for example in the range of 5.1 - 5.5 for cheese and of 3.9 - 4.4 for yoghurt.
  • the final pH will as a rule be the result of the fermentation process and the buffer action possibly associated with this.
  • the food product is a fruit juice or similar drink, such as, for example, products in which dairy products such as milk or yoghurt and fruit juices have been processed, which have a limited shelf-life.
  • the nonanoic acid can be used in a manner known per se for antimicrobial agents, in particular antifungal agents, that is to say by adding the nonanoic acid or a nonanoic acid- containing additive to the food or food product, or incorporating the nonanoic acid or a nonanoic acid-containing additive in the food or food product, during and/or after the preparation thereof.
  • the nonanoic acid can be uniformly mixed or distributed through the food and/or used on the surface of the food, for example by spraying or brushing with nonanoic acid (for example in the form of an aqueous solution), by immersing (in particular cheese) in a solution of nonanoic acid or by applying a nonanoic acid-containing coating.
  • an aqueous solution or suspension of nonanoic acid or another nonanoic acid-containing, preferably liquid, mixture which contains 100 - 5,000 ppm, in particular 200 to 3,000 ppm nonanoic acid and which furthermore can contain all constituents known per se for solutions for applying a cheese coating, such as (the constituents of) synthetic coatings known per se (for example based on copolymers) and/or coatings based on foodstuffs.
  • the nonanoic acid concentration in the coating can be 5,000 ppm (which corresponds to 49.2 mg nonanoic acid per kg cheese), 1,000 ppm (which corresponds to 9.8 mg/kg cheese) or 100 ppm (which corresponds to 0.98 mg/kg cheese).
  • nonanoic acid-containing cheese coating thus obtained, the cheeses which have been provided with such nonanoic acid-containing cheese coatings and the nonanoic acid- containing solutions which are used in this operation form further aspects of the invention.
  • a further advantage of nonanoic acid is that it is also able to counteract and/or prevent too extensive development of the surface flora on the cheese (coating) - which can lead to the cheese rind being adversely affected - (this is in contrast to natamycin, that essentially is not able to exert any influence on bacterial growth).
  • nonanoic acid will be used to replace the one or more antimicrobial, in particular antifungal, additives already used in a food known per se.
  • the nonanoic acid can advantageously be used in those foods for which the known antimicrobial agents are unsuitable or less suitable.
  • the use of nonanoic acid can form an alternative to the sterilisation treatments and/or similar antimicrobial treatment (that is to say other than the use of an antimicrobial additive) which are otherwise required.
  • nonanoic acid is used in particular to replace natamycin, in particular in applications in the dairy and cheese industries.
  • nonanoic acid is highly preferentially compatible with the food, that is to say the use of nonanoic acid according to the invention has no adverse effect on the flavour, odour, consistency, pH or other desired characteristics of the food, at least not during the time that the food has to be or can be kept or stored prior to end use or consumption.
  • this means that the food must be acid-resistant to a certain extent, that is to say at least must be able to withstand the pH that is obtained by the use of the nonanoic acid in the abovementioned amounts.
  • the use of a separate nonanoic acid-containing coating can offer a solution.
  • the food can furthermore contain all other additives known per se for the food, provided that these are compatible with nonanoic acid and do not adversely affect the antimicrobial action thereof.
  • nonanoic acid is used as antimicrobial agent according to the invention, as a rule no further antimicrobial agent will be required and according to one embodiment of the invention the food essentially contains exclusively nonanoic acid as antimicrobial agent, that is to say in the amounts specified above (in per cent by mass or ppm).
  • nonanoic acid in addition to the nonanoic acid minor amounts of one or more further antimicrobial agents known per se are present, such as the agents which are mentioned below.
  • nonanoic acid makes up at least 80 % (m m), preferably at least 90 % (m/m) and more preferentially at least 95 - 99 % (m/m) of all antimicrobial constituents present (that is to say added to the food in order to achieve an antimicrobial action).
  • nonanoic acid in a mixture with one or more antimicrobial agents which are known per se and are compatible with nonanoic acid, a synergistic effect possibly being able to be obtained.
  • the nonanoic acid will as a rule replace some of the quantity of the known antimicrobial agent usually used.
  • Nonanoic acid will as a rule make up at least 30 % (m/m), preferably at least 50 % (m/m) and more preferentially at least 70 % (m m) of the total antimicrobial constituents in such mixtures.
  • antimicrobial agents that can be used according to the invention in combination with nonanoic acid are: sorbic acid and salts thereof, benzoic acid and salts thereof, para-hydroxybenzoic acid or esters thereof, propionic acid and salts thereof, pimaricin, polyethylene glycol, ethylene/propylene oxides, sodium diacetate, caprylic acid (octanoic acid), ethyl formate, tylosin, polyphosphate, metabisulphite, nisin, subtilin and diethyl pyrocarbonate.
  • the nonanoic acid can furthermore be used in combination with agents for adjusting the acidity, including the acids acceptable for foods, such as citric acid, acetic acid and the like.
  • the nonanoic acid can, in particular, protect the food (which in this case can have a pH in the range from 2 to 6) against acid-resistant moulds.
  • acid-resistant moulds are, but are not restricted to, Penicillium roqueforti, P. carneum, P. italicum, Monascus ruber and/or Paecilomyces variotii (which occur, for example, in rye bread); and Penicillium glandicola, Penicillium roqueforti, Aspergillus flavus, Aspergillus candidus and or Aspergillus terreus (which, for example, occur in products which have been preserved by acid, such as sour and/or sweet-sour preserves).
  • the nonanoic acid is present in the undissociated form in the food.
  • the general rule in this context is that the amount of undissociated nonanoic acid increases at lower pH: for instance, approximately 90 % of the nonanoic acid is present in undissociated form at a pH of approximately 3.8.
  • nonanoic acid is therefore also used in foods which have a low pH, such as a pH in the range 2 to 6, preferably 3 to 5.8, or 4 to 5.6.
  • a pH in the range 2 to 6, preferably 3 to 5.8, or 4 to 5.6 for instance, for example, the pH of cheese rind is around 4.8 - 5.3.
  • nonanoic acid is a stable molecule in both the dissociated and undissociated form.
  • nonanoic acid is a natural substance which occurs in plants, inter alia; - nonanoic acid has been approved for use in foods (inter alia by the FDA); nonanoic acid remains stable under the majority of processing steps/processes for food products; nonanoic acid is less susceptible to UV light than is, for example, natamycin; nonanoic acid is stable in the presence of metals in metallic form; - nonanoic acid is stable under heating.
  • nonanoic acid can also find use outside the food sector as an antifungal, yeast-inhibiting and/or antibacterial agent.
  • nonanoic acid has been approved for use in foods, so that it can be used in applications where it can come into contact with foods or the human body, such as with the skin.
  • a number of possible, non-limiting applications are: use as or in disinfectant(s), cleaning agent(s) and the like, for both domestic and industrial applications; disinfection and/or cleaning (including preventive treatment) of conveyor belts, pallets and the like; disinfection and/or cleaning (including preventive treatment) of apparatus, products and/or surfaces which come into contact with foods, such as cutting machines, mixers, stirrers, sorting equipment, filling machines and other equipment from the food processing industry; vats, dishes, tanks, plates, containers and other holders; and also worktops, sink units and the like; both domestic and industrial; disinfection and/or cleaning (including preventive treatment) of areas which may or may not be enclosed, in particular areas in which food products are processed and/or stored, such as cupboards, refrigerators, kitchens, factory areas, freight areas, warehouses and the like (both domestic and industrial); and in particular cheese warehouses and other commercial premises where P.
  • discolor can occur; coating and/or (preventive) treatment of packaging for, for example, foods (such as fruit, vegetables, cheese and the like), for example made of materials such as plastic, paper, cardboard or shaped cardboard; protection of fruit, such as oranges, lemons, grapefruit, apples, pears; nuts and
  • These aspects of the invention in general comprise the treatment of a surface or substrate that is susceptible to mould formation, or that can be contaminated or infected by a mould and/or the spores thereof, with an amount of nonanoic acid which has an effective antifungal and/or antibacterial action.
  • nonanoic acid can be used on the surface or substrate in any suitable way, such as, once again, spraying or brushing with nonanoic acid (for example in the form of an aqueous solution), by applying a nonanoic acid-containing coating or by use of an atomised spray containing nonanoic acid. This treatment can optionally be repeated.
  • nonanoic acid can once again be used instead of, or together with, disinfectants which may be known for the envisaged application, as well as in combination with other agents or constituents customary for the envisaged application.
  • the nonanoic acid and any other constituents can optionally be marketed in a suitable container, for example in a bottle or in the form of a spray.
  • nonanoic acid according to the invention furthermore relates to the control - in particular the inhibition - of bacterial growth during fermentation processes, such as the preparation of fermented food products such as yoghurt.
  • use is made in particular of the antibacterial action of nonanoic acid.
  • nonanoic acid can be used to control the pH during or after such fermentation processes and in particular to prevent and/or reduce post-acidification of, for example, yoghurt, as explained in more detail in the examples. The taste of the yoghurt is retained for longer as a result.
  • the antimicrobial, in particular antifungal, action according to the invention will also be obtained.
  • Figure 1 is a graph (time against visible intensity of mould formation) in which the effect of nonanoic acid on mould formation on Gouda cheese is shown;
  • Figure 2 is a graph (time against number of bacteria) which shows the effect of nonanoic acid (pelargonic acid) on the development of yoghurt bacteria at 7 °C;
  • - Figure 3 is a graph (time against pH) which shows the effect of nonanoic acid (pelargonic acid) on the post-acidification of yoghurt at 7 °C;
  • Figure 4 is a graph (time against number of bacteria) which shows the effect of nonanoic acid (pelargonic acid) on the development of yoghurt bacteria at 32 °C;
  • Figure 5 is a graph (time against pH) which shows the effect of nonanoic acid (pelargonic acid) on the post-acidification of yoghurt at 32 °C;
  • Figure 6 is a plot (time against number of bacteria) that shows the influence of nonanoic acid (pelargonic acid) on the development of surface flora on cheese rind
  • Figure 7 is a plot (time against number) that shows the effect of nonanoic acid (pelargonic acid) on the development of D. hansenii, S. cereviseae, C. lipolytica and R. rubra;
  • Figures 8 A and 8B are photographs which show the effect of natamycin (Figure 8 A) and nonanoic acid ( Figure 8B), respectively, on the inhibition of the growth of P. discolor on blocks of cheese rind;
  • Figure 9 is a graph (time against number of bacteria) which shows the effect of nonanoic acid on the growth of Bacillus cereus in soup;
  • Figure 10 is a graph (time against number of bacteria) which shows the effect of nonanoic acid on the growth of Staphylococcus aureus in soup;
  • Figure 11 is a graph (time against number of cells) which shows the effect of nonanoic acid on the growth of Debaromyces hansenii in a milk/fruit juice drink
  • Figure 2 is a graph (time against number of cells) which shows the effect of nonanoic acid on the growth of Penicillium italicum in a milk/fruit juice drink.
  • Example 1 Use of nonanoic acid in Gouda cheese
  • Example 2 Use of nonanoic acid in yoghurt to prevent post-acidification
  • various concentrations of nonanoic acid were added to freshly prepared yoghurt.
  • One series was monitored for 8 hours at the culture temperature (filling, 32 °C) and another series was incubated for 14 days at 7 °C (refrigerator temperature). This was carried out to investigate the extent to which nonanoic acid has an effect during yoghurt fermentation and/or during storage of the filled packs of yoghurt.
  • the pH was determined and the number of yoghurt bacteria.
  • Example 3 Effect of nonanoic acid on the surface flora of cheese rind
  • Example 4 Use on blocks of cheese rind
  • blocks of cheese rind were inoculated with P. discolor.
  • the blocks were incubated at 20 °C and high relative humidity (95 %). These conditions were employed to provide the mould with the optimum opportunity to grow and are therefore more severe than the usual conditions for maturing cheese.
  • Figure 8 shows photographs of the blocks of cheese rind taken two weeks after inoculating with P. discolor.
  • One series was treated with natamycin (Figure 8A) and the other series with nonanoic acid (Figure 8B). It can clearly be seen that after 2 weeks mould formation was inhibited in the blocks treated with nonanoic acid.

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EP00980091A 1999-11-01 2000-11-01 Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent Withdrawn EP1227723A2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NL1013448A NL1013448C2 (nl) 1999-11-01 1999-11-01 Gebruik van nonaanzuur als schimmelwerend middel.
NL1013448 1999-11-01
PCT/NL2000/000787 WO2001032020A2 (en) 1999-11-01 2000-11-01 Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent

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EP1227723A2 true EP1227723A2 (en) 2002-08-07

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EP (1) EP1227723A2 (cs)
AU (1) AU1739201A (cs)
CZ (1) CZ20021832A3 (cs)
HU (1) HUP0204151A3 (cs)
NL (1) NL1013448C2 (cs)
SK (1) SK7372002A3 (cs)
WO (1) WO2001032020A2 (cs)

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GB0011674D0 (en) * 2000-05-15 2000-07-05 Unilever Plc Ambient stable beverage
US9168329B2 (en) * 2006-09-01 2015-10-27 Wisconsin Alumni Research Foundation Beta-peptides with antifungal activity
UA104899C2 (uk) 2009-08-06 2014-03-25 Анітокс Корпорейшн Консервант для води та корму
US12075777B2 (en) * 2010-08-27 2024-09-03 Anitox Corporation Antimicrobial formulation
PT2768539T (pt) * 2011-10-20 2017-03-13 Anitox Corp Formulações antimicrobianas com ácido pelargónico
KR20140097253A (ko) 2011-11-30 2014-08-06 아니톡스 코포레이션 알데히드, 유기산 및 유기산 에스테르의 항미생물성 혼합물
MX2023001766A (es) * 2020-08-17 2023-02-23 Hiteshkumar Anilkant Doshi Composicion pesticida que comprende azufre elemental y sal de colina de acido pelargonico.
CN112353946B (zh) * 2020-11-19 2022-11-11 上海创宏生物科技有限公司 一种弱毒活疫苗用无菌处理剂及其制备方法和应用
WO2023095138A1 (en) * 2021-11-24 2023-06-01 The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization (Aro) (Volcani Institute) Compositions of 4-cumylphenol, 8-nonenoic acid, or analogs thereof, and methods of using same

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US2154449A (en) * 1938-06-15 1939-04-18 Ward Baking Co Process for inhibition of mold
US3931413A (en) * 1972-06-15 1976-01-06 National Research Development Corporation Control of fungi
US4343788A (en) * 1979-06-29 1982-08-10 The Procter & Gamble Company Antimicrobial polymer compositions
US4406884A (en) * 1981-06-23 1983-09-27 The Procter & Gamble Company Topical antimicrobial composition
CA1331559C (en) * 1986-04-21 1994-08-23 Jon Joseph Kabara Antimicrobial preservative compositions and methods
FI912955L (fi) * 1990-06-25 1991-12-26 Res Found Mental Hygiene Antimikroba fettsyrasammansaettningar.
US5366995A (en) * 1991-05-01 1994-11-22 Mycogen Corporation Fatty acid based compositions for the control of established plant infections
PT762837E (pt) * 1995-03-31 2002-07-31 Schur Jorg Peter Processo para melhorar a durabilidade e/ou estabilizacao de produtos degradaveis microbiologicamente

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HUP0204151A3 (en) 2003-05-28
HUP0204151A2 (hu) 2003-03-28
WO2001032020A3 (en) 2001-12-27
NL1013448C2 (nl) 2001-05-09
CZ20021832A3 (cs) 2002-10-16
SK7372002A3 (en) 2002-11-06
WO2001032020A2 (en) 2001-05-10

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