Europäisches Patentamt *EP001229805B1* (19) European Patent Office Office européen des brevets (11) EP 1 229 805 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A23L 3/3472, A23L 3/3526, of the grant of the patent: A23L 3/3535, A23L 3/3508, 25.02.2004 Bulletin 2004/09 A23B 7/154 (21) Application number: 00980671.2 (86) International application number: PCT/US2000/032078 (22) Date of filing: 20.11.2000 (87) International publication number: WO 2001/035769 (25.05.2001 Gazette 2001/21) (54) Beverage products comprising a preservative system consisting of an isothiocyanate in combination with a sorbate and/or a benzoate Getränkeprodukte enthaltend ein Konservierungssystem bestehend aus einem Isothiocyanat in Kombination mit einem Sorbat und/oder einem Benzoat Boissons pourvues d’un système de conservation contenant un isothiocyanate en combinaison avec un sorbate et/ou un benzoate (84) Designated Contracting States: • BUNKE, Paul, Ralph AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU Cincinnati, OH 45248 (US) MC NL PT SE TR (74) Representative: Kremer, Véronique et al (30) Priority: 18.11.1999 US 442558 Procter & Gamble Service GmbH Sulzbacher Strasse 40-50 (43) Date of publication of application: 65824 Schwalbach am Taunus (DE) 14.08.2002 Bulletin 2002/33 (56) References cited: (73) Proprietor: THE PROCTER & GAMBLE COMPANY EP-A- 0 452 273 EP-A- 0 867 125 Cincinnati, Ohio 45202 (US) WO-A-00/54838 WO-A-98/50005 GB-A- 568 009 GB-A- 568 011 (72) Inventors: GB-A- 1 473 037 US-A- 3 725 030 • EKANAYAKE, Athula US-A- 3 844 761 US-A- 4 756 919 Cincinnati, OH 45249 (US) US-A- 4 948 617 US-A- 5 968 567 • BUNGER, John, Robert US-A- 5 985 303 Union, KY 41091 (US) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 229 805 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 229 805 B1 Description FIELD OF THE INVENTION 5 [0001] The present invention relates to beverage products comprising a constituent comprising one or more isothi- ocyanate compound and a sorbate and/or benzoate preservative. The present invention further relates to a method of preserving a beverage product by incorporating the foregoing preservative system. BACKGROUND OF THE INVENTION 10 [0002] Consumer products can provide a hospitable environment for rapid microbial growth. Such exposure can, and frequently does, result from inadvertent microbial inoculation of the product during manufacturing or packaging. Spoilage microorganisms, for example in food or beverage products, can then rapidly proliferate by feeding on nutrients provided by the product. 15 [0003] Preservatives, such as sorbates, benzoates, organic acids, and combinations thereof have been used in various products, particularly foods and beverages, to provide some degree of microbial inhibition. At levels effective to inhibit microbial growth, some of these preservatives can contribute off-flavors in the product, thus making the product undesirable for its intended purpose. For example, accepted usage levels for potassium sorbate is typically in the range of from about 200 ppm to about 3000 ppm. However, at the higher end of this accepted usage range, potassium sorbate 20 can contribute to off-flavors in the foods or beverages. [0004] Additionally, certain preservative systems are not effective in the presence of fortification components, includ- ing various vitamins and minerals. For example, calcium fortification in certain food or beverage products can render the preservative system inactive, thereby failing to inhibit microbial growth. Therefore, wherein nutrient fortification is desirable, expensive preservative components such as dimethyl dicarbonate (DMDC) must be utilized to inhibit micro- 25 bial growth in the fortified product. [0005] It has been disclosed that oil of mustard, which contains isothiocyanates, exhibits an antibacterial and an- timycotic effect in oral therapies and on certain foods. See e.g., Sekiyama et al., U.S. Patent No. 5,334,373, assigned to Nippon Sanso Corp., issued August 2, 1994; and Madaus et al., U.S. Patent No. 3,998,964, issued December 21, 1976. However, it has been suggested that mustard oil can irritate the mucous membranes and may not be well tolerated 30 by individuals ingesting the oil. See e.g., Madaus et al., Additionally, mustard oil can exhibit strong characteristic flavors which render the oil unfavorable for use in food or beverage products. Accordingly, mustard oil has not been widely known or widely utilized in the art for its antibacterial and antimycotic effect, particularly in products suitable for ingestion such as food and beverage products. [0006] However, the present inventors have surprisingly discovered that one or more isothiocyanate compounds, in 35 combination with a sorbate and / or benzoate preservative, exhibits a strong antimicrobial effect without imparting off- flavors or offensive odors in the final product In doing so, the present inventors have discovered a synergistic relation- ship between the relative effects of each of the preservative components when utilized in combination. Surprisingly, when utilized in combination, each of the preservative components are effective at levels low enough to maintain the organoleptic integrity of the final beverage product. The present inventors have further surprisingly discovered that 40 such antimicrobial effect is maintained even in the presence of fortification nutrients such as calcium, thus overcoming the problems associated with currently fortified products. Accordingly, the preservative systems of the present invention are utilized at relatively low levels, provides maintenance of flavor and odor integrity, and are effective against microbial growth even in the presence of fortification nutrients. [0007] Representative of the art are also following references: EP-A-867 125 discloses a preservative system for 45 food and beverage comprising water-soluble hemicellulose, optionally in combination with other possible preservative ingredients. US 5,968,567 discloses food and beverage products containing glucosinolates and isothiocyanates de- rived from Cruciferae in the form of seed flour or seed extracts. US 5,958,303 discloses the use of horseradish extract or mustard extract or allyl isothiocyanate as food preservative. GB-A-568009 and GB-A-568011 discloses insecticidal preparations containing a mixture of alkyl isothiocyanate and a benzoate. US 4,948,617 discloses food products con- 50 taining mustard oil as flavoring agent and sodium benzoate as preservative. GB-A-1,473,037 discloses preservative for food by incorporation of various antimicrobial agents, agents whereby turnip extract and sodium benzoate are cited as possibilities in extensive lists. EP-A-452 273 discloses the combination of pepper-like constituents selected from extensive listing (including mustard oil and horseradish extract) with formate esters as flavoring compositions in foods and beverages. WO98/50005 discloses cosmetic compositions, whereby horseradish extract, sorbate and benzoate 55 are mentioned as possible ingredients in extensive lists. All of these references fail to disclose beverage products with the specific combination of ingredients claimed. 2 EP 1 229 805 B1 SUMMARY OF THE INVENTION [0008] The present invention relates to beverage products comprising the following preservative system: 5 (a) a constituent comprising one or more isothiocyanate compounds; and (b) a preservative selected from sorbate preservatives, benzoate preservatives, and mixtures thereof. [0009] The present invention further relates to methods of preserving a beverage product comprising incorporating the foregoing preservative system into the product. 10 [0010] The present invention relates to beverage products comprising: (a) a constituent comprising one or more isothiocyanate compounds; (b) a preservative selected from the group consisting of sorbate preservatives, benzoate preservatives, and mix- tures thereof; and 15 (c) a beverage member selected front the group consisting of water, fruit juice, tea solids, milk solids, fruit flavors, botanical flavors, and mixtures thereof. [0011] In accordance with the present invention, the beverage products requiring an antimicrobial effect include for example, ready-to-drink products and concentrates). 20 DETAILED DESCRIPTION OF THE INVENTION [0012] The present invention relates to beverage products according to claim 1, and to a method of preserving a beverage product according to claim 9. 25 [0013] All percentages, ratios, and proportions used herein are by weight unless otherwise specified. Definition and Usage of Terms [0014] The following is a list of definitions for term used herein: 30 [0015] As used herein, "alkenyl" is an unsaturated hydrocarbon straight, branched, or cyclic chain radical. Preferably, the alkenyl is a straight or branched chain radical, most preferably straight. Alkenyls have at least one olefinic double bond. Unless otherwise specified, alkenyls have from 2 to 15 carbon atoms (C2 -C15); preferably from 2 to 10 carbon atoms (C2-C10); more preferably from 2 to 8 carbon atoms (C2 -C8), even more preferably from 2 to 6 carbon atoms (C2 -C6), and most preferably from 2 to 4 carbon atoms (C2 -C4). Non-limiting