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PREPARATION OF LIGHT STABLE HOP PRODUCTS

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PREPARATION OF LIGHT STABLE HOP PRODUCTS ( preparation-light-stable-hop-products )

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US 7,413,758B2 34 chemical and biological transformations, an essence and ?a vorant can be prepared for addition to an unhopped beer. These kettle hop ?avor essences and ?avorants provide economy,consistency,?exibility,qualityandconvenienceto the brewing process because only one unhopped Wort is required to breW a stock of unhopped beer, Which can then be dosed With the desired amount of kettle hop ?avor essence and ?avorant. acids, the treated hop solids are mixed With a second alcohol solvent to form a mixture of the treated hop solids and the second alcohol solvent, and the mixture of the treated hop solids and the second alcohol solvent is separated into hop solidsresiduesandasecond?ltrateincludingalpha/iso-alpha acids,Whereinalightstablehopproductcomprisingthehop solids residues is formed. The exhaustive extraction (double extraction,orDX)ofhopsolidsyieldshopsolidsresiduesand ?ltratescontainingmostofanytracealpha/iso-alpha-acids. InUS. Pat.Nos.5,013,571and5,013,572,Hayteaches methodsforconvertingalphaacidstohopbittering?avorsby Inasecondaspectofthepresentinvention,the?rst?ltrate exposing the alpha acids to an environment capable of isomeriZing and reducing the alpha acids to form either tet rahydroiso-alpha-acids or hexahydroiso-alpha acids, and then steam stripping odor forming impurities from such to producepuri?edlightstablehopbiteringcompounds. and/or the second ?ltrate may then be subjected to further processing. In one version of the second aspect of the inven tion,the?rst?ltrateand/orthesecond?ltrateareappliedtoan ionexchangeremovalofthealpha/iso-alpha-acidsinthe?rst ?ltrate and/or the second ?ltrate from the double extraction, folloWedbyreturnofthee?luentfromtheionexchangetothe hop solidsresiduesofthedoubleextraction,andfolloWedby concentration of this mixture to obtain a more ?avorful light Inadditiontotheabove,US. Pat.No.4,002,683,ofTodd, Jr.,teachesaprocessforisomeriZingalphaacidstoiso-alpha acids by contact With an aqueous solution of a metal ion to formmaterialssuitableforuseasbitteringadditives,Wherein stablehopproduct.Inanotherversionofthesecondaspectof aWater-immiscibleorganicsolventinWhichthealphaacidis20 solubleisemployed.Todd,Jr.,alsoteaches,inUS. Pat.Nos. 4,666,731and4,844,939,theseparationoftheconstituentsof CO2 Hop Extracts employing aqueous alkali, folloWed by conversion of the separated alpha acid fraction into an iso alphaacidorisohumulonefractionusefulinthebitteringof25 beer.Moreover,Todd,Jr.etal.teach,inUS. Pat.Nos.4,778, 691 and 4,956,195, the removal of odor-forming impurities fromhop?avorsbyextractingintoWateratapH above5,and separatingtheaqueousphasecontainingtheimpuritiesfrom thealpha/iso-alpha-acidsinthe?rst?ltrateand/orthesecond thepuri?edhop?avors,torecovera?avoringagentselected30 ?ltratefromthedoubleextraction,folloWedbyreturnofthe fromunreducedandreducedalphaacidsandiso-alpha-acids ?ltrateofthehydrogenationtothehop solidsresiduesofthe Whichisessentiallyodor-causing-impurityfree.And,inUS. doubleextraction,andfollowedbyconcentrationofthismix Pat. No. 5,073,396, Todd, Jr. teaches the use ofa non-acidic hop ?avor fraction for production of beer, Wherein the hop ?avorfractionismadefromCO2hopextracttoprovidean 35 extractessentiallydevoidofalphaandbetaacids,byfraction breWsWerecon?rmedtobelightstable,andthehopproducts ation of the hop extract With an alkaline solution Within con trolledpHranges.InUS Pat.No.5,296,637,Steginketal. teach production of odor-free tetrahydroisohumulates from alphaacidsviathetetrahydrohumulatesandsubsequent40 isomeriZation. Thus, there are a number of processes for the preparation, separation, puri?cation, and use ofhop bittering ?avors for beer.HoWever,amethodfortheproductionoflightstablehop productscontaininglitleornoalpha/iso-alpha-acids,Which 45 also impart hop aroma and ?avor to the breWing of beer equivalent to or comparable to the aroma and ?avor attained from the use of conventional Whole hops or hop pellets, has notpreviouslybeenprovided. 50 SUMMARY OF THE INVENTION attributes. In a ?rst aspect, the present invention is a method for the preparation of a light stable hop product. In the method, hop solidsaremixedWitha?rstalcoholsolventtoformamixture ofthehopsolidsandthe?rstalcoholsolvent,themixtureof65 the hop solids and the ?rst alcohol solvent is separated into treated hop solids and a ?rst ?ltrate including alpha/iso-alpha employed made a contribution to kettle hop ?avor attributes ofthebeer.Stillfurther,itWas foundthatthelightstablehop products could be reconstituted With: (i) a hop oil fraction (HOF),thatis,asolvent(e.g.,CO2)hopextractinWhichthe alpha acids are removed and a portion of the beta acids are removed leaving, among other things, hop oils and beta acids, (i) a beta-acid rich fraction, that is, a solvent (e.g., CO2) hop extractinWhichthealphaacidsareremovedleav ing,amongotherthings,hopoilsandbeta-acids,and/or(i) light stable bittering agents (e.g., hydrogenated iso-alpha acids)toyieldafurther?avorimprovementWithoutcausing lightinstabilityinbreWedproduct. Itisthusanadvantageofthepresentinventiontoprovidean inexpensivemethodforthepreparationoflightstablehop products,Whichareusefulinprovidinghop?avorandmouth feelforbreWedproducttobepackagedinclear,?intorgreen bottles. Such breWed product is found to be less subject to skunk ?avor resulting from exposure to light over time. The present invention provides means for providing light stable hop products Which impart hop aroma and ?avor to beerWhenusedinpreparingbeer,Withoutthepotentialfor 55 lightsensitivityinthebeerresultinginskunkiness.Several techniques have been employed to prepare light stable hop products that can be used to prepare light stable beers. Beers preparedusingtheselightstablehopproductsWereevaluated tionoflightstablehopproductsWhichareusefulinproviding bysensorytestingforlightstabilityandacceptablehop?avor60 theinvention,the?rst?ltrateand/orthesecond?ltrateare subjectedtoametalionprecipitationtreatmentremovalofthe alpha/iso-alpha-acids in the ?rst ?ltrate and/or the second ?ltrate from the double extraction, folloWed by return of the ?ltrateoftheprecipitationtreatmenttothehopsolidsresidues ofthedoubleextraction,andfolloWedbyconcentrationof thismixturetoobtainalightstablehopproduct.Inyetanother version of the second aspect of the invention, the ?rst ?ltrate and/or the second ?ltrate are subjected to hydrogenation of ture to obtain a light stable hop product. When the light stable hop products of these techniques WereusedinthepreparationofbreWedbeer,theresulting DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for the prepara hop?avorandmouthfeelforbreWedproducttobepackaged in clear, ?int or green bottles. The method includes the steps of mixing hop solids With a ?rst alcohol solvent to form a mixture of the hop solids and the ?rst alcohol solvent, sepa ratingthemixtureofthehop solidsandthe?rstalcohol solventintotreatedhopsolidsanda?rst?ltrateincluding alpha/iso-alpha acids, mixing the treated hop solids With a second alcohol solvent to form a mixture of the treated hop

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