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US 7,413,758B2 12 PREPARATION OF LIGHT STABLE HOP PRODUCTS CROSS REFERENCES TO RELATED APPLICATIONS Thisapplicationisacontinuation-in-partofUS. applica tion Ser. No. 10/106,603 ?led Mar. 26, 2002, now US. Pat. No. 7,258,887 STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH Notapplicable. BACKGROUND OF THE INVENTION 1.FieldoftheInvention Thepresentinventionisdirectedtothepreparationoflight stablehopproducts,containinglitleornoalpha/iso-alpha 20 acids, that can be used for providing hop ?avor and character for beer products Which may be packaged in ?int, clear, or green bottles. This invention produces a hop product Which imparts not only hop ?avor and mouthfeel indistinguishable fromoriginalWholehops,butalsoprovideslightstabilityand25 ?avor variations in malt beverages. Such treated hop solids can contribute hop ?avor and mouthfeel to beer With loW bitterness. 2.DescriptionoftheRelatedArt fermentedbeveragebyadditionofthesolidhopresidue remainingafterCO2 extraction(asthesolehoppingagent)to the Wort, boiling the mixture, removing the solids from the fermented mixture, and fermenting the remainder to obtain the ?nal product. While this method does provide a breW having less bitterness but a comparable hop ?avor to a breW preparedusingWholehops,itdoesnotfullyaddresstheissue of iso-alpha-acids present in the solid hop residue. In one embodiment of the Ting et al. ’235 method, the solid hop residue and a hop character fraction (HCF, i.e., the residue of a hop extract remaining after removal of all alpha-acids and all beta-acids from the hop extract obtained from the CO2 extraction), are pelletiZed and added to the Wort prior to or duringboiling.AfterthemixtureisboiledandfermentedWith yeast to convert the hop components and the Wort, the solids arethenseparatedtoobtaintheliquidproduct.Sincethesolid hop residue is present in the breWing kettle, iso-alpha-acids are present in the ?nal breW, potentially leading to an unde sirable skunk ?avor. Tingetal.,inUS. Pat.No. 5,767,319,teachconversionof iso-alpha-acids to light stable tetrahydroiso-alpha-acids, Which are knoWn bittering agents. While an improvement over previous conversion methods, the patent necessitates additional treatment steps to obtain speci?ed metal salts of theiso-alpha-acids,dissolvingthemetalsaltsinanaqueous alcoholmedium,andreducingtheiso-alpha-acidsbyhydro genationunderspeci?cconditionstoformthetetrahydroiso alpha-acids, Which are then recovered from the reaction medium. Such a method clearly adds complexity to the desiredgoalofprovidingalightstableformofahopproduct. Hops,intheformofeitherthegrounddriedplantorpellets,30 havebeenusedinbreWingtogivemaltbeveragessuchasbeer or ale their essential characteristics of aroma, ?avor, mouth feel, and bitterness, as Well as contributing foam and anti microbialactivitytothebreW.Hopscomprisesoftresins,hard supercritical?uidform,fortheconversionofiso-alpha-acids resins,Waxes,lipids,andcarbohydrates.Thesoftresins35 orbeta-acidstotetrahydroiso-alpha-acids(tetrahydroisohu include alpha-acids, beta-acids and hop oils. The hops are usuallyaddedtotheboilingWortinthebreWingkettle,andthe promoterforthebeta-acids.Aspreviouslyindicated,tetrahy Wortisthenfermentedbyyeasttoproducethe?nishedprod droiso-alpha-acidsareknoWnlight-stableFDA-approvedbit uct.Duringboiling,alpha-acidsinthehopsareconvertedinto iso-alpha-acids,Whichcontributethebitternessandfoamin40 the ?nished product. Such iso-alpha-acids are, hoWever, sus ceptible to a photochemical reaction Which produces “skunk”, an undesirable sulfur ?avor characteristic resulting from the presence of 3-methyl-2-butene-1-thiol. This reac tionisknoWntooccurWhenthe?nishedproductincluding 45 iso-alpha-acids is packaged in ?int (clear White), clear or greenbottlesandexposedtolight. teringagentsWhichmay beusedtoaddhop ?avoringtobeer. Inthispatent,itWasnotedthatthetetrahydroiso-alpha-acids Were previously generally not made from the alpha-acids for economicalreasons.Thehydrogenationmethodofthispatent permits the use of alpha-acids as a source of tetrahydroiso alpha-acidforuseinbreWing. Additional patents to Ting et al. include US. Pat. Nos. 5,523,489,5,874,633,and5,917,093.Inthesepatents,meth ods for the preparation and/or puri?cation of tetrahydroiso alpha-acids (tetrahydroisohumulones) are discussed. In US. Pat. No. 5,523,489, tetrahydroisohumulones are prepared fromisohumulonesbyhydrogenationinethanol.InUS.Pat. No. 5,917,093, alpha-acids and beta-acids present in the hop oilfractionofCO2 hopextractsarepuri?edbymixingWithan absorbent to remove catalyst poisons, thereby reducing the amount of catalyst necessary for hydrogenation to tetrahy droiso-alpha-acidsandtetrahydrodesoxy-alpha-acids.In US. Pat.No.5,874,633,patenteesteachamethodofhydro genating and formulating a starting solution of iso-alpha Hopsmaybeseparatedintohopsolidsandhopsoftresins, i.e. hop extract containing the extracted alpha-acids, beta acids,andhopoils,byemployingliquid/supercriticalCO2or50 less-polar organic solvent extractions. The hop extract con tributes most of the bitterness ?avor in beer. Beer breWed solely With the hop extract does not impart a complete hops ?avor spectrum to the beer due to the absence of the Water solublecomponents,Whichapparentlyremaininthehop55 solids. The bitterness ?avor can also be added as pure forms afterfermentationorinthe?nishedproducts.Tointegratethe fullspectrumofhop?avorWouldthusrequiretheadditionof acidstoobtainconcentratedsolutionsoftetrahydroiso-alpha hop solids to the breW, but the hop solids have been found to containtraceamountsofalpha/iso-alpha-acids,Which,dueto 60 lackoflightstability,contributetoskunkinessinbeer.There fore, to obtain the full ?avor of the hops While avoiding skunkinessinbeer,lightstablehopproductsthatcanbeused to produce a beer Would be of value. ItisknoWnthatthereareanumberofUS.patentsrelative 65 to this matter, such as Ting et al. US. Pat. No. 5,783,235, Which teaches the preparation of a hop ?avored, less bitter lation and characteriZation of a group of odorless and non volatile glycosides from extracted hops (hop solids Which havepreviouslybeenextractedWithliquid/supercriticalCO2 or less-polar solvents.) These glycosides are Water soluble andconsistofagroupofaromaticcompoundsconjugatedto mono-, di- and tri-saccharides. These glycosides are respon sible for the formation of kettle hop ?avor. Through both Inaddition,Tingetal.teach,inUS. Pat.No. 6,020,019,a method for the hydrogenation of hop soft resins, Wherein carbon dioxide is used as a reaction solvent, in liquid or mulones), preferably using an acidic loWer alcohol to act as a acids. InUS. Pat.No. 5,972,411,Goldsteinetal.teachtheisoPDF Image | PREPARATION OF LIGHT STABLE HOP PRODUCTS
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