WO2001032020A2 - 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 Download PDFInfo
- Publication number
- WO2001032020A2 WO2001032020A2 PCT/NL2000/000787 NL0000787W WO0132020A2 WO 2001032020 A2 WO2001032020 A2 WO 2001032020A2 NL 0000787 W NL0000787 W NL 0000787W WO 0132020 A2 WO0132020 A2 WO 0132020A2
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- nonanoic acid
- food
- cheese
- ppm
- acid
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- 239000000725 suspension Substances 0.000 description 1
- SITVSCPRJNYAGV-UHFFFAOYSA-L tellurite Chemical compound [O-][Te]([O-])=O SITVSCPRJNYAGV-UHFFFAOYSA-L 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
- 235000019375 tylosin Nutrition 0.000 description 1
- 229960004059 tylosin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier 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
- A61Q17/005—Antimicrobial preparations
-
- 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
- A01N37/00—Biocides, 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/10—Preserving with acids; Acid fermentation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C19/00—Cheese; Cheese preparations; Making thereof
- A23C19/097—Preservation
- A23C19/10—Addition of preservatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
- A23C9/1307—Milk 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
Definitions
- 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 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.
- 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.
- 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;
- Example 1 Use of nonanoic acid in Gouda cheese
- 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.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Animal Behavior & Ethology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Nutrition Science (AREA)
- Pest Control & Pesticides (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Dairy Products (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00980091A EP1227723A2 (en) | 1999-11-01 | 2000-11-01 | Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent |
SK737-2002A SK7372002A3 (en) | 1999-11-01 | 2000-11-01 | Use of nonanoic acid, a dairy product, a fruit juice, a cheese, and a cheese coating and an agent for the treatment of cheese surface |
AU17392/01A AU1739201A (en) | 1999-11-01 | 2000-11-01 | Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent |
HU0204151A HUP0204151A3 (en) | 1999-11-01 | 2000-11-01 | Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL1013448 | 1999-11-01 | ||
NL1013448A NL1013448C2 (en) | 1999-11-01 | 1999-11-01 | Use of nonanoic acid as an anti-fungal agent. |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001032020A2 true WO2001032020A2 (en) | 2001-05-10 |
WO2001032020A3 WO2001032020A3 (en) | 2001-12-27 |
Family
ID=19770174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/NL2000/000787 WO2001032020A2 (en) | 1999-11-01 | 2000-11-01 | Use of nonanoic acid as an antimicrobial agent, in particular an antifungal agent |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1227723A2 (en) |
AU (1) | AU1739201A (en) |
CZ (1) | CZ20021832A3 (en) |
HU (1) | HUP0204151A3 (en) |
NL (1) | NL1013448C2 (en) |
SK (1) | SK7372002A3 (en) |
WO (1) | WO2001032020A2 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001087096A1 (en) * | 2000-05-15 | 2001-11-22 | Unilever Plc | Ambient stable beverage |
US20120128843A1 (en) * | 2009-08-06 | 2012-05-24 | Kurt Richardson | Water and feed preservative |
EP2611310A2 (en) * | 2010-08-27 | 2013-07-10 | Anitox Corporation | Antimicrobial formulation |
JP2014534967A (en) * | 2011-10-20 | 2014-12-25 | アニトックス コーポレーション | Antimicrobial formulation containing pelargonic acid |
US9168329B2 (en) * | 2006-09-01 | 2015-10-27 | Wisconsin Alumni Research Foundation | Beta-peptides with antifungal activity |
US10021901B2 (en) | 2011-11-30 | 2018-07-17 | Anitox Corporation | Antimicrobial mixture of aldehydes, organic acids and fatty acid esters |
CN112353946A (en) * | 2020-11-19 | 2021-02-12 | 上海创宏生物科技有限公司 | Sterile treatment agent for attenuated live vaccine and preparation method and application thereof |
AU2021327950B2 (en) * | 2020-08-17 | 2023-06-01 | Hiteshkumar Anilkant Doshi | Pesticidal composition comprising elemental sulphur and choline salt of pelargonic acid |
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 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP0022289A1 (en) * | 1979-06-29 | 1981-01-14 | THE PROCTER & GAMBLE COMPANY | Antimicrobial polymer compositions and use thereof in medical devices |
US4406884A (en) * | 1981-06-23 | 1983-09-27 | The Procter & Gamble Company | Topical antimicrobial composition |
EP0244144A1 (en) * | 1986-04-21 | 1987-11-04 | Jon Joseph Kabara | Antimicrobial preservative compositions |
EP0465423A2 (en) * | 1990-06-25 | 1992-01-08 | Research Foundation for Mental Hygiene, Inc. | Antimicrobial fatty compositions |
WO1992019104A2 (en) * | 1991-05-01 | 1992-11-12 | Mycogen Corporation | Fatty acid based compositions for the control of established plant infections |
WO1996029895A1 (en) * | 1995-03-31 | 1996-10-03 | Schuer Joerg Peter | Process for improving the shelf life of and/or stabilising products which can spoil under the action of microbes |
-
1999
- 1999-11-01 NL NL1013448A patent/NL1013448C2/en not_active IP Right Cessation
-
2000
- 2000-11-01 EP EP00980091A patent/EP1227723A2/en not_active Withdrawn
- 2000-11-01 CZ CZ20021832A patent/CZ20021832A3/en unknown
- 2000-11-01 WO PCT/NL2000/000787 patent/WO2001032020A2/en not_active Application Discontinuation
- 2000-11-01 AU AU17392/01A patent/AU1739201A/en not_active Abandoned
- 2000-11-01 SK SK737-2002A patent/SK7372002A3/en unknown
- 2000-11-01 HU HU0204151A patent/HUP0204151A3/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP0022289A1 (en) * | 1979-06-29 | 1981-01-14 | THE PROCTER & GAMBLE COMPANY | Antimicrobial polymer compositions and use thereof in medical devices |
US4406884A (en) * | 1981-06-23 | 1983-09-27 | The Procter & Gamble Company | Topical antimicrobial composition |
EP0244144A1 (en) * | 1986-04-21 | 1987-11-04 | Jon Joseph Kabara | Antimicrobial preservative compositions |
EP0465423A2 (en) * | 1990-06-25 | 1992-01-08 | Research Foundation for Mental Hygiene, Inc. | Antimicrobial fatty compositions |
WO1992019104A2 (en) * | 1991-05-01 | 1992-11-12 | Mycogen Corporation | Fatty acid based compositions for the control of established plant infections |
WO1996029895A1 (en) * | 1995-03-31 | 1996-10-03 | Schuer Joerg Peter | Process for improving the shelf life of and/or stabilising products which can spoil under the action of microbes |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6562387B2 (en) | 2000-05-15 | 2003-05-13 | Lipton, Division Of Conopco, Inc. | Ambient stable beverage and process of making |
WO2001087096A1 (en) * | 2000-05-15 | 2001-11-22 | Unilever Plc | Ambient stable beverage |
US9168329B2 (en) * | 2006-09-01 | 2015-10-27 | Wisconsin Alumni Research Foundation | Beta-peptides with antifungal activity |
US10785975B2 (en) * | 2009-08-06 | 2020-09-29 | Anitox Corporation | Water and feed antimicrobial preservative |
EP3023009B1 (en) | 2009-08-06 | 2016-12-07 | Anitox Corporation | Water and feed preservative |
US20120128843A1 (en) * | 2009-08-06 | 2012-05-24 | Kurt Richardson | Water and feed preservative |
EP2611310A4 (en) * | 2010-08-27 | 2014-04-16 | Anitox Corp | Antimicrobial formulation |
EP2611310A2 (en) * | 2010-08-27 | 2013-07-10 | Anitox Corporation | Antimicrobial formulation |
JP2014534967A (en) * | 2011-10-20 | 2014-12-25 | アニトックス コーポレーション | Antimicrobial formulation containing pelargonic acid |
US20150031762A1 (en) * | 2011-10-20 | 2015-01-29 | Anitox Corporation | Antimicrobial Formulations with Pelargonic Acid |
EP2768539B1 (en) | 2011-10-20 | 2016-12-07 | Anitox Corporation | Antimicrobial formulations with pelargonic acid |
US10736343B2 (en) * | 2011-10-20 | 2020-08-11 | Anitox Corporation | Antimicrobial formulations with pelargonic acid |
US10021901B2 (en) | 2011-11-30 | 2018-07-17 | Anitox Corporation | Antimicrobial mixture of aldehydes, organic acids and fatty acid esters |
AU2021327950B2 (en) * | 2020-08-17 | 2023-06-01 | Hiteshkumar Anilkant Doshi | Pesticidal composition comprising elemental sulphur and choline salt of pelargonic acid |
CN112353946A (en) * | 2020-11-19 | 2021-02-12 | 上海创宏生物科技有限公司 | Sterile treatment agent for attenuated live vaccine and preparation method and application thereof |
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 |
Also Published As
Publication number | Publication date |
---|---|
CZ20021832A3 (en) | 2002-10-16 |
WO2001032020A3 (en) | 2001-12-27 |
EP1227723A2 (en) | 2002-08-07 |
NL1013448C2 (en) | 2001-05-09 |
SK7372002A3 (en) | 2002-11-06 |
HUP0204151A2 (en) | 2003-03-28 |
AU1739201A (en) | 2001-05-14 |
HUP0204151A3 (en) | 2003-05-28 |
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