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WO1998033391A1 - Composition antimicrobienne et procede de production d'un effet antimicrobien sur des produits alimentaires - Google Patents

Composition antimicrobienne et procede de production d'un effet antimicrobien sur des produits alimentaires Download PDF

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Publication number
WO1998033391A1
WO1998033391A1 PCT/US1998/001784 US9801784W WO9833391A1 WO 1998033391 A1 WO1998033391 A1 WO 1998033391A1 US 9801784 W US9801784 W US 9801784W WO 9833391 A1 WO9833391 A1 WO 9833391A1
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WIPO (PCT)
Prior art keywords
composition
set forth
food
meat
product
Prior art date
Application number
PCT/US1998/001784
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English (en)
Inventor
Richard A. White
Original Assignee
Koch Enterprises, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Koch Enterprises, Inc. filed Critical Koch Enterprises, Inc.
Priority to AU61384/98A priority Critical patent/AU6138498A/en
Publication of WO1998033391A1 publication Critical patent/WO1998033391A1/fr

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Classifications

    • 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
    • A23B4/00—Preservation of meat, sausages, fish or fish products
    • A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
    • A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
    • A23B4/20—Organic compounds; Microorganisms; Enzymes
    • 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
    • A23B2/733—Compounds of undetermined constitution obtained from animals or plants
    • 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
    • A23B2/767—Organic compounds containing sulfur

Definitions

  • This invention relates in general to additives for meat, poultry and other food products, and, more particularly, to antimicrobial compositions and methods for adding antimicrobial compositions to meat and poultry products.
  • Bacterial contamination is an inherent consequence of producing and processing some food products, including among others, raw meat, poultry and fish products.
  • Two categories of bacteria commonly encountered in food products are pathogens and spoilage flora. It is essential that harmful amounts and/or harmful species of bacteria not be present in food, often requiring some type of antimicrobial action to be taken in order to kill the bacteria already present. It is also essential for food manufacturers, packers, distributors and retailers to reduce and control the levels of bacteria in food products, especially of the pathogens, in order to prevent illness or death in the ultimate consumer of that food product. Pathogens present a significant risk to human health and can result in food borne illness, and in some circumstances, death.
  • the term "food borne illness” generally refers to illnesses which are caused by microorganisms consumed by eating any type of food.
  • the Centers for Disease Control (CDC) estimates that food borne illnesses affect a growing number of people every year, with an increasing number of deaths resulting from these illnesses.
  • Food companies are constantly striving to implement antimicrobial techniques that will reduce the risk of harmful bacterial pathogens reaching the consuming public. When people complain of "food poisoning," they may actually have been exposed to the microorganisms that cause food borne illness.
  • Microbes, bacteria and pathogens are other terms used to describe the microorganisms that cause food borne illness.
  • bacteria which are harmless to human health, or are beneficial and are even used in food processing.
  • other forms or bacteria are utilized to combat disease.
  • bacteria account for more than two-thirds of all outbreaks of food borne illness in the United States.
  • an object of the present invention to provide a composition and method for producing an antimicrobial effect in food products in order to control and reduce harmful bacterial pathogens in the food products so that associated health risks are reduced.
  • an antimicrobial composition and method for producing an antimicrobial effect by inhibiting the growth of harmful pathogens and food spoilage bacteria, whereby the composition can be used with raw meat and poultry products.
  • an antimicrobial composition and method for reducing the harmful bacterial pathogens present in food products, the method comprising providing a composition having as an active component a mustard seed product or derivative thereof; applying the composition to a food product; blending the composition throughout the food product; allowing the composition to contact the surface area presented by the food product; and creating an antimicrobial effect on the bacteria present in the food product.
  • an antimicrobial composition and method for reducing the harmful bacterial pathogens present in food products comprising providing a composition having as an active component a mustard seed product or derivative thereof, a synthetically produced equivalent thereof, or a combination of a mustard seed product or derivative thereof and a synthetically produced equivalent thereof; applying the composition to a food product; blending the composition throughout the food product; allowing the composition to contact the surface area presented by the food product; and creating an antimicrobial effect on the bacteria present in the food product.
  • an antimicrobial composition and method for extending the shelf life of food products by reducing and controlling food spoilage bacteria present in food products and thereby maintaining the color and controlling the odor of the food products, which composition includes as an active component a mustard seed product or derivative thereof, a synthetically prepared equivalent thereof, or a combination of a mustard seed product or derivative thereof and a synthetically prepared equivalent thereof; applying the composition to a food product; blending the composition throughout the food product; allowing the composition to contact the surface area presented by the food product; and creating an antimicrobial effect on the bacteria present in the food product.
  • a composition for producing an antimicrobial effect on food products which comprises an active ingredient, the active ingredient including a mustard seed product or derivative thereof, a synthetically prepared equivalent thereof, or a combination of the two. Due to the antimicrobial tendencies of mustard seed products and derivatives, it has been discovered that its direct addition to raw food products can help to control and reduce the level of bacteria contained within such food product.
  • mustard seed product as used herein is defined to include, but is not limited to, a wide variety of mustard seed products and derivatives which are useful in the present invention. Additionally, it is understood that these products can be naturally derived, or can be the synthetic equivalents of such products. These products include whole mustard seeds, ground mustard seeds, ground mustard bran (the outside coating of the mustard seed), mustard flour (the ground interior of the seed), mustard oil (extracted from the seed), mustard meal (the residual after the mustard oil is extracted from the seed), and isothiocyanates (also extracted from the mustard seed) along with other enzymes and compounds which are derivatives of mustard seed. As stated above, these products can be the synthetic equivalents of above-listed derivatives, including synthetic or artificial isothiocyanates.
  • Mustard is a member of the Crucifer family, brassica genus.
  • Some of the more common types of mustard seed include Brassica Nigra (black), Brassica Hirta or Sinapis Alba (yellow or white), and Brassica Juncea (black, brown or oriental).
  • this invention is not intended to be limited to the above-listed types of mustard seed.
  • Different varieties of mustard seeds can produce varying amounts of isothiocyanate, thought to be responsible for the antimicrobial effect of the seeds as set forth in more detail below. These variations are dependent upon the different types, combinations and levels of glucosinolate compounds within the particular variety of the mustard, as well as upon varied growing conditions.
  • any other genus associated with the Crucifer family is also useful in accordance with this invention.
  • Some of the plant varieties within this family include turnips, cabbage, brussel sprouts, radishes, rutabaga, broccoli, cauliflower, rape seed, horse radish, and cranbe. It is believed that each of this plants contains a glucosinolate compound and an enzyme capable of activating the glucosinolate.
  • Mustard seeds contain active components, such as an enzyme referred to as myrosinase, along with several compounds referred to as glucosinolates.
  • the glucosinolates and the enzyme co-exist within the seed without combining, but when allowed to combine in the presence of water they create isothiocyanate, which is believed to be responsible, at least in part, for the antimicrobial activity.
  • One of the antimicrobial isothiocyanates is known as allyl isothiocyanate (AITC), although other compounds within the seed may similarly be active components which contribute to the antimicrobial effect.
  • AITC allyl isothiocyanate
  • the composition comprises as an active component the mustard seed extract AITC, discussed above.
  • AITC is plated onto a dry carrier and processed into a dry powder.
  • Any conventional carrier can be employed, and can include starch or the like. Specific examples of carriers include maltodextrin and potato starch, although those skilled in the art will recognize that other suitable carriers are equally useful in accordance with this invention.
  • liquid AITC is sprayed onto a dry powder carrier, with the resulting product being a dry powder that has the liquid AITC incorporated therein as an ingredient.
  • the composition can include as the active ingredient a starch plated AITC which is encapsulated with fat by conventional means.
  • the fats which can be employed to encapsulate the AITC include animal fats such as beef fat or pork fat, although other suitable fats can be used.
  • the AITC can also be encapsulated by vegetable oils, or any other appropriate encapsulating products known to those skilled in the art. The AITC is first plated, and is then encapsulated as discussed above to form a resultant dry powder. Such encapsulation delays the release of the AITC, and thereby the antimicrobial effect thereof, until the food product within which it is incorporated is being cooked.
  • the composition comprises encapsulated AITC (or other active component), combined with the non- encapsulated AITC (or other active component), to enhance the antimicrobial action, as the non-encapsulated product controls the bacteria on contact even under refrigeration temperatures, while the encapsulated product provides additional antimicrobial effect as the fat melts and the previously encapsulated AITC is allowed to contact the food product during the cooking process just before the food is consumed. This aids in antimicrobial effectiveness, particularly in situations in which marginal cooking procedures are employed.
  • the food products which are particularly suited for employing the antimicrobial composition of this invention include a variety of foods and meat proteins, such as raw meats, which can further include beef, pork, poultry, lamb, veal, fish, restructured meats, and processed meats, particularly uncooked processed meats such as fermented sausage. Collectively, these food products are referred to herein simply as "meat” or “meat products.” Such terms are not intended to be limiting, as other food products plagued by bacterial pathogens can be aided by this invention.
  • Particularly suited for the antimicrobial composition and process of the present invention are ground meats, whereby the grinding process further distributes the composition within the meat product to maintain contact with and thereby control surface bacteria which are also incorporated into the meat during the grinding process.
  • restructured meats are also particularly suited for the antimicrobial composition and process of the present invention, as the composition which has coated the surface of the meat pieces maintains contact with the surface bacteria which ultimately is incorporated into the restructured meat product as the pieces are bound together, shaped and formed.
  • composition of the present invention is preferably combined with the food product to deliver a concentration of the active component, for example AITC, ranging from about 50 to 5000 ppm, and more preferably in the range of about 200 to 2500 ppm, and most preferably in the range of about 500 to 2500 ppm.
  • a concentration of the active component for example AITC
  • concentration of active component ranging from about 50 to 5000 ppm, and more preferably in the range of about 200 to 2500 ppm, and most preferably in the range of about 500 to 2500 ppm.
  • a method for producing an antimicrobial effect on food products comprising creating a composition including a mustard seed product or derivative thereof, a synthetically produced equivalent thereof, or a combination of a mustard seed product or derivative thereof and a synthetically produced equivalent thereof; applying the composition to a food product; blending the composition throughout the food product to effectively coat the surface area thereof; allowing the composition to contact the surface area presented by the food product and creating an antimicrobial effect on the bacteria present on the food product.
  • an antimicrobial composition can be added directly to food products to produce an antimicrobial effect in the food products, particularly in raw meat products.
  • the composition can be added either as an ingredient in the meat product, or as a product applied to the surface of the meat.
  • the antimicrobial composition is added to ground meat immediately before, during or immediately subsequent to the grinding process in order to evenly distribute the product throughout the ground meat, killing a large percentage of the bacteria within the meat on contact, including such bacteria as E. coll, and inhibiting the growth of the bacteria.
  • the composition is added to restructured meat products prior to the shaping and forming of the same.
  • restructured meat refers to a meat product formed from smaller pieces of typically lower valued meats which are bound together, shaped and reformed to create a more valuable piece of meat. Examples of restructured meat products include chicken fillets and restructured beef tenderloin steaks.
  • the following process is preferred. Chunks of meat or meat trimmings are provided, and an appropriate amount of the antimicrobial composition, preferably plated AITC, sufficient to achieve the desired concentration of AITC or other active component, is added to the meat, such as by uniformly sprinkling the antimicrobial composition over the meat pieces.
  • the meat pieces with the composition sprinkled thereon are then mixed in a conventional manner for a period of time sufficient to evenly distribute the powder over the surface of the meat pieces.
  • Conventional food mixers are appropriately used for this procedure.
  • this may be followed by a holding time for additional antimicrobial activity prior to subsequent processing. This time can range from approximately one to 30 minutes.
  • the coated meat pieces are then processed by grinding or restructuring by conventional means. Because microorganisms are generally present only on the exposed surfaces of meat pieces, the antimicrobial composition is applied to the meat pieces prior to grinding or restructuring. As the meat pieces are ground or restructured, the composition remains in contact with the surface bacteria that is ground or restructured therein. Thus, in accordance with the present invention, application of the composition prior to grinding or restructuring dramatically increases the effective concentration of the antimicrobial composition on the potentially contaminated meat surfaces, thereby dramatically increasing the antibacterial activity.
  • the composition in a second method of the present invention, can be processed into a slurry or other sprayable form for spraying directly on the carcass or large portions of meat, including primal or subprimal sections, such as at the processing plant, or just prior to packaging or freezing. Bacteria are present only on the outer surface of the meat pieces or poultry carcass, and thus such a method of treatment can be effective for producing an antimicrobial effect which will ultimately create a safer end product.
  • still another method of the present invention contemplates processing the composition into a liquefied form as by the addition of a large quantity of water thereto.
  • composition is then introduced into a vat or other container, and the carcass (or other large portion) of the meat or poultry product is dipped therein prior to packaging, freezing or further processing of such products.
  • Other applications of this invention contemplate use of the composition with fish products, including spraying the composition onto the fish prior to packaging, processing or freezing.
  • the antimicrobial characteristics of the composition when combined with meat and poultry products, as well as with other food products, can achieve within these food products a much needed antimicrobial effect, controlling a number of known harmful or food spoilage bacteria or other pathogen strains.
  • the multiple known strains of E In addition to the multiple known strains of E.
  • composition used in accordance with the methods of this invention is also useful for killing and inhibiting the growth of Streptococcus faecalis, Shigella flexneri, Hafnia alvei, Enterobacter aerogenes, Serratia marcescens, Staphylococcus aureus, Pseudomonas aeruginosa, Citrobacter freundii, Klebsiellapneumoniae, multiple strains of Listeria, and multiple strains of Salmonella.
  • this list is intended to be illustrative, and is not intended to limit the scope of microorganisms against which this invention is useful.
  • AITC or other active ingredient in the composition will likewise control multiple types of yeasts, molds, and fungi.
  • the composition of the present invention is also useful against food spoilage bacteria. This, coupled with the antioxidant effect in mustard seed products, as well as their derivatives and synthetic equivalents, tends to enhance the shelf life of food products.
  • this invention is useful in maintaining the color of a food product, such as a meat product, thereby further enhancing the shelf life of the product.
  • an initial antimicrobial action occurs when the composition is first mixed with the meat or other food product, and a secondary action occurs during the cooking process as the increased temperature combines with the composition to create additional antimicrobial activity.
  • the same general process is employed as set forth above for combining the composition with the meat product.
  • the meat is then cooked in patties or other appropriate form.
  • the antimicrobial effect of the composition is enhanced.
  • the antimicrobial composition which comprises encapsulated AITC, either alone or in combination with non-encapsulated AITC.
  • the non-encapsulated AITC achieves an initial antimicrobial effect upon direct contact with the meat product, as described above, and upon cooking, the encapsulated AITC achieves an additional antimicrobial action as the fat surrounding the AITC melts, and the AITC incorporated therein is then allowed to directly contact the meat within which it is situated.
  • the following examples are intended to be illustrative of the present invention, but are not intended to be limiting.
  • the first type of mustard seed product comprised AITC plated onto starch to form a dry powdered or granular product. This first product was prepared in two concentrations, a starch-maltodextrin plated extract with 7% available AITC, and a starch plated extract with 14% available AITC.
  • the second type of mustard seed product comprised AITC plated onto starch and then encapsulated by fat. This product was prepared as a fat-encapsulated/starch plated extract with 7% available AITC. Trimmings such as those used to make ground beef were provided.
  • a portion of the beef was removed for use in evaluating the natural flora present therein, and the remaining beef was inoculated with approximately 4 log, 0 cfu/g of a five strain mixture of E. coli O157:H7 stationary phase culture and allowed to stand for 18 to 24 hours at 2° C. From each of these two portions, a control was prepared which consisted of a segment of the meat treated with potato starch only, without any .AITC or other active component incorporated therein.
  • the 7% starch/plated AITC was added to a first part of both the inoculated and the non-inoculated beef trimmings by sprinkling the same as uniformly as possible to achieve a concentration of approximately 500 ppm AITC with respect to the beef as Samples la and lb, and the 14% starch/plated AITC was added to a second part of the beef portions to achieve a concentration of 500 ppm AITC as Samples 2a and 2b.
  • the encapsulated AITC was also sprinkled uniformly on third and fourth parts of both the inoculated and the non-inoculated beef to achieve concentrations of 500 ppm and 2200 ppm AITC with respect to the beef, as Samples 3a, 3b and 4a, 4b, respectively.
  • the meat trimmings with the plated AITC sprinkled thereon were then mixed in a conventional food mixer for a total of two minutes to evenly distribute the powder over the surface of the meat pieces. These coated meat pieces were held for approximately 30 minutes, and were then coarse ground by conventional means.
  • Each of the above samples were packaged and stored for a total of seven days.
  • a first segment of each of the Samples la-4a and lb-4b and of the controls was stored at 4°C, and a second segment was stored at 11 °C.
  • Samples la-4a and lb-4b and the controls were evaluated at intervals during storage for total microbial levels of the natural food spoilage flora, and of E. coli. After four days, the samples were then fine ground by conventional means. Further readings of the total microbial levels were taken at days 5 and 7. The results of these tests are summarized below in Tables 1-8.
  • the ground beef and antimicrobial composition samples were formulated using plated AITC and encapsulated AITC products, and the general methods as set forth in Example 1.
  • the composition used in this example included a starch plated extract with 14% available AITC, and a fat-encapsulated/plated extract with 7% available AITC.
  • Beef trimmings used to make ground beef were provided. All of the beef was inoculated with a five strain mixture of stationary phase E. coli O157:H7 cultures to a level of approximately 7 log, 0 cfu/g. This inoculated beef was allowed to stand for 18 to 24 hours at 2°C.
  • a control segment was combined with potato starch, and the remaining beef trimmings were combined with the plated AITC by uniform sprinkling to achieve concentrations of approximately 500 ppm and 2200 ppm AITC with respect to the beef, Samples 5 and 6, respectively.
  • Beef trimmings were also combined by uniform sprinkling with the encapsulated AITC to achieve concentrations of approximately 500 ppm and 2200 ppm AITC with respect to the beef, Samples 7 and 8, respectively.
  • the meat trimmings with the AITC composition sprinkled thereon were then mixed in a conventional food mixer for a total of two minutes to evenly distribute the powder over the surface of the meat pieces. These coated meat pieces were held for approximately 30 minutes, and were then coarse ground by conventional means.
  • Samples 5-8 were then packaged and stored for a total of 4 days at 4°C. Readings were taken to determine microbial levels of the Samples and the control initially, and on day 4 after fine grinding. On day 4, the Samples and controls were fine ground and patties were prepared from each. The patties were cooked on day 5 on an electric skillet to internal endpoint temperatures of 130, 140, 150 and 160°F measured at the geometric center of the patties using a rapid response type K thermocouple probe. Two patties (patty A and patty B) were measured from each sample at each temperature. Prior to cooking and at each cooking temperature, levels of E. coli were noted and log reductions in recoverable E. coli populations were determined and compared among mustard types and concentrations. The results of these tests are summarized in Table 9 below.
  • POS means E.coli O157:H7 was detected by enrichment techniques but below the detection limit of 5 cfu/g (0.71og 10 cfu/g).
  • An antimicrobial composition comprising as its active component a combination of AITC extracted from mustard seed and of synthetically prepared AITC, both plated into a dry powder as discussed above.
  • the composition is sprinkled uniformly over the surfaces of the meat to coat the surfaces and achieve a concentration of AITC with respect to the meat of 2500 ppm.
  • the meat pieces with the AITC composition sprinkled thereon are then mixed in a conventional manner using a conventional food mixer for a period of time sufficient to evenly distribute the powder over the surface of the meat pieces.
  • the meat and AITC composition mixture is held for approximately 10 minutes.
  • the coated meat pieces are then ground by conventional means to produce ground meat.
  • the meat chunks and antimicrobial composition are combined according to the process of Example 3, but the composition comprises as the active ingredient synthetic AITC.
  • the synthetic AITC can be plated or encapsulated, or a combination of the two. A sufficient amount of the composition is combined with the meat product to achieve a concentration of AITC with respect to the meat of 1500 ppm.
  • Chunks of meat or meat trimmings are provided.
  • An antimicrobial composition is prepared comprising as its active ingredient a combination of AITC extracted from mustard seed and plated into a dry powder as discussed above, and synthetically prepared AITC.
  • the composition is uniformly sprinkled over the surfaces of the meat to coat the surfaces and achieve a concentration with respect to the meat of 800 ppm AITC.
  • the meat pieces with the AITC composition sprinkled thereon are then mixed in a conventional manner using a conventional food mixture for a period of time sufficient to evenly distribute the powder over the surface of the meat pieces.
  • the coated meat pieces are then processed by binding, shaping and forming to make a restructured meat product.
  • spices other than mustard seed product are useful.
  • these spices should have essential oils which have antimicrobial tendencies.
  • Some of the more effective of these spices include garlic, onion, and clove products.
  • Other spices exhibiting a lesser degree of antimicrobial effect include ginger, basil, cumin, and coriander. It has been found, and is within the scope of this invention, that an enhanced antimicrobial effect may exist in the combination of mustard or its derivative, or the synthetic equivalent thereof, with one or more of these or other spices, or with other flavoring ingredients (such as liquid smoke) to cause the desired antimicrobial effect.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

Cette invention concerne une composition antimicrobienne et un procédé qui permet de produire un effet antimicrobien sur des produits alimentaires par inhibition de la croissance de bactéries pathogènes et de bactéries qui altèrent la nourriture. La composition contient un ingrédient actif qui est une graine de moutarde ou un dérivé de cette dernière ou encore un équivalent de synthèse de cette dernière. On ajoute directement la composition dans les produits alimentaires tels que des viandes crues ou non cuites pour obtenir un effet antimicrobien au moyen de la réduction et de la régulation de la croissance des bactéries, sans pour autant modifier négativement l'aspect, le goût ou la texture de la viande.
PCT/US1998/001784 1997-01-30 1998-01-30 Composition antimicrobienne et procede de production d'un effet antimicrobien sur des produits alimentaires WO1998033391A1 (fr)

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Application Number Priority Date Filing Date Title
AU61384/98A AU6138498A (en) 1997-01-30 1998-01-30 Antimicrobial composition and method for food products

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US3665497P 1997-01-30 1997-01-30
US60/036,654 1997-01-30
US1538898A 1998-01-29 1998-01-29
US09/015,388 1998-01-29

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
US6361812B1 (en) 1999-11-18 2002-03-26 The Procter & Gamble Co. Products comprising an isothiocyanate preservative system and methods of their use
WO2003001922A1 (fr) * 2001-06-28 2003-01-09 L'air Liquide - Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude Procede de conservation et de desinfection d'un produit alimentaire
WO2005032283A1 (fr) * 2003-10-01 2005-04-14 The Procter & Gamble Company Conservateurs a base d'isothiocyanate et procedes d'utilisation correspondants
WO2007074350A1 (fr) * 2005-12-28 2007-07-05 Andrea Marinello Dispositif de traitement de maladies de l'artère carotide
US8475862B2 (en) 2003-10-01 2013-07-02 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
CN113967226A (zh) * 2021-11-15 2022-01-25 广东工业大学 一种抑制细菌群体感应系统的药物

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EP0312519A2 (fr) * 1987-09-18 1989-04-19 Monsanto Company Contrôle des bactéries sur les carcasses de poulets
JPH04357953A (ja) * 1991-02-06 1992-12-10 Noboru Yamada ガス状抗菌性物質徐放製剤
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JPH0812511A (ja) * 1994-06-30 1996-01-16 Nakano Vinegar Co Ltd 徐放性抗菌材の製造方法、該方法により得られる徐放性抗菌材、及びその用途

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JPS5799182A (en) * 1980-12-11 1982-06-19 Ueda Seiyu Kk Mustard oil emulsified composition having antimicrobial action
EP0312519A2 (fr) * 1987-09-18 1989-04-19 Monsanto Company Contrôle des bactéries sur les carcasses de poulets
JPH04357953A (ja) * 1991-02-06 1992-12-10 Noboru Yamada ガス状抗菌性物質徐放製剤
EP0557946A1 (fr) * 1992-02-26 1993-09-01 The Green Cross Corporation Composition contenant l'isothiocyanate allylique et son utilisation
JPH0812511A (ja) * 1994-06-30 1996-01-16 Nakano Vinegar Co Ltd 徐放性抗菌材の製造方法、該方法により得られる徐放性抗菌材、及びその用途

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Cited By (12)

* Cited by examiner, † Cited by third party
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US6361812B1 (en) 1999-11-18 2002-03-26 The Procter & Gamble Co. Products comprising an isothiocyanate preservative system and methods of their use
US6558723B2 (en) 1999-11-18 2003-05-06 The Procter & Gamble Co. Products comprising an isothiocyanate preservative system and methods of their use
US7105190B2 (en) 1999-11-18 2006-09-12 The Procter & Gamble Company Products comprising an isothiocyanate preservative system and methods of their use
WO2003001922A1 (fr) * 2001-06-28 2003-01-09 L'air Liquide - Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude Procede de conservation et de desinfection d'un produit alimentaire
WO2005032283A1 (fr) * 2003-10-01 2005-04-14 The Procter & Gamble Company Conservateurs a base d'isothiocyanate et procedes d'utilisation correspondants
AU2004278001B2 (en) * 2003-10-01 2008-08-14 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
US7658961B2 (en) 2003-10-01 2010-02-09 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
US8084072B2 (en) 2003-10-01 2011-12-27 Procter & Gamble Isothiocyanate preservatives and methods of their use
US8277859B2 (en) 2003-10-01 2012-10-02 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
US8475862B2 (en) 2003-10-01 2013-07-02 The Procter & Gamble Company Isothiocyanate preservatives and methods of their use
WO2007074350A1 (fr) * 2005-12-28 2007-07-05 Andrea Marinello Dispositif de traitement de maladies de l'artère carotide
CN113967226A (zh) * 2021-11-15 2022-01-25 广东工业大学 一种抑制细菌群体感应系统的药物

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