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US 7,413,758B2 9 10 Example 5 An alkalimetalormetalionprecipitationtreatmentofthe double extractedhop solids?ltrateWas alsoundertaken. Hop alpha-acidsandiso-alpha-acidsoftenshoWacharacteristicof complexingWithalkalimetalions,divalentions,andtransi tional metal ions such as magnesium, calcium, lead, ferric, Zinc, etc. The tri-keto group on the alpha-acid molecule has thefunctionalityofchelatingWithvariousmetalions.Some of the complexes thus formed are less soluble in Water and alcohol.Accordingly,inordertoselectdesirableandeffective alkalimetalormetalionsWhichcomplyWithFDA regula tions, and to stilmeet breWing requirements, a number of inorganic salts such as calcium carbonate, calcium hydrox ide,magnesiumhydroxide,magnesiumacetate,Zincsulfate, and Zinc acetate Were selected. To 1200millilitersof?ltratefromthedoubleextraction,an equal amount of distilled Water Was added to reduce the solubilityofsubsequentformingcomplexesofalpha/iso-al pha-acids.From 1to5gramsofthealkalimetalormetalsalts, Ca(OH)2,Ca(OAc)2,CuCl,CUSO4,ZnSO4,andZn(OAc)2, 20 respectively, Were added to the diluted ?ltrate, and mixed for one hour at room temperature. The amounts of alpha/iso alpha-acidWeremonitoredbyHPLC, untilnofurtherreduc tion Was observed. The precipitate Was removed by ?ltration through a Whatman #4 ?lter paper, and the ?ltrate Was then 25 added back to the solid residues of the double extraction in a TABLE 2-continued Data of Light Stable Hop Products Added in BreWs 5 liter round bottom ?ask. The thus formed mixture Was rotary evaporated (under 31 torr at 40-500 C.) to remove ethanol and Water. LyophiliZing removed the residual mois ture and afforded dried solids for subsequent usage. Example6 CuCl ZnSO4 ZnSO4 Zn(OAc)2 Zn(OAc)2 NaBH4 NaBH4 Double X Double X DoubleX+HOF 192 DoubleX+HOF 175 A hydrogenationofthedoubleextractedhopsolids?ltrate Was alsoundertaken.Theresidualalpha/iso-alphaacidsinthe double extracted hop solids ?ltrate can be hydrogenated to 35 light stable form as tetrahydroalpha-iso-alpha acids. The residual alpha/iso-alpha acids in the double extracted hop solids ?ltrate Were subjected to hydrogenation using noble metalsasthecatalysts.After?ltratingoffthecatalysts,alight stableethanolsolutionstilcontaining?avorprecursorsWas 40 obtained. Recombining the ethanol solution and the double extractedhopsolidresiduesaffordedaslurry.Evaporationoff of the ethanol in the mixture produced a light stable hop product. To400millilitersofdoubleextractedhopsolids?ltrateWas 45 added 2 grams of Pd/C catalyst in an autoclave. The mixture Was hydrogenated under 30 psig and 500 C. for 1 hour. The catalyst Was removed by ?ltration and the ?ltrate Was then combined With the double extracted hop solid residues in a 5 literround bottom ?ask. The mixture Was rotary evaporated under 27 torr at 30-400 C. until the solids Were dried. 50 Example7 A numberoftheabovelightstablehopproductsWerethus preparedandanalyZedbyHPLC (asshoWninTable2). 55 TABLE 2 Data of Light Stable Hop Products Added in Brews # LS-HopsType Treatment Addition Rate % Residualalpha/ (ppm) iso-alpha-acids 2000 0.110 2000 0.080 60 65 l GalenaHop Solids 2 CascadeHop Solids None None 30 Despite the estimation and prediction of light stability, actuallightstabilitymustbecon?rmedbysensoryobserva tion. Possible light stable hop products made in accordance With each of the four techniques discussed above, and other treated light stable hop product samples, Were submitted for pilot breWs, as folloWs. The double extracted hop solids residues of Example 2 (Double X, Examples 23 and 24) employing 95% ethanol extraction, Were breWed at 1920 and 1748 ppm, respectively, as Pilot BreWs 8679 and 8670. To evaluatetheeffectoftheHop OilFraction(HOF) and compensateforthelossofaromaand?avorcomponents resultingfromdoubleextraction,1gramofHOF Wasaddedto 8 grams of the double extracted hop solids residues of Example 2 (Examples 25 and 26). These Were breWed at 192 and 175 ppm levels, as Pilot BreWs 8685 and 8686. Ionexchangeresintreatedsamples(Examples3,4,5,6and 11) Were breWed as Pilot BreWs 8664, 8666, 8665, 8667, and 8673. Sample 12 did not breW due to containing a higher alpha/iso-alpha-acidscontent. AdditionalPilotBreWs,numbered8671,8672,8674,8675, 8676, 8677, 8683, 8681, and 8682 Were hopped With various alkali metal ion precipitated light stable (LS) Hop Products correspondingtoExamples8,10,13,15,16,20,14,18,and 19,respectively. In addition to the above, tWo sodium borohydride reduc tion treated hop solids (Examples 21 and 22) Were breWed as PilotBreWs 8678and8684.ThreecontrolPilotBreWs,Num bers 8661, 8662, and 8663, Were unhopped (8661) and hopped With 2000 ppm of Galena hop solids (8662) and Cascadehopsolids(8663),respectively.Analyticaldatamay be found in Tables 3 and 4, hereinafter. Samples of the Pilot BreWs, all bottled in 12 OZ clear bottles, then packaged in six-pack paper carriers having a height of 5% inches, Were exposed to 25 foot-candles of ?uorescentlightfor20days.A totalof23productsWerethus evaluated. Testing Was conducted on each exposed sample, andcomparedtoacorrespondingunexposedsample.Allsuch testing involved subjectively rating the samples on sulfur characterandskunkycharacter.Mean scoresarebasedupon # LS-HopsType Treatment Addition Rate % Residualalpha/ (ppm) iso-alpha-acids 1592 0.010 1434 0.014 1630 0.040 984 0.003 1612 0.037 1288 0.014 862 0.019 660 0.010 1216 0.015 1338 0.036 846 0.012 1468 0.017 1570 0.042 1194 0.010 860 0.013 1476 0.021 1288 0.023 1760 0.029 1538 0.110 1846 0.085 1920 0.048 1748 0.016 0.048 0.016 3 lA-Galena 4 lB-Cascade 5 3A-Galena 6 3B-Cascade 7 4A-Galena - 8 4B-Cascade 9 5A-Galena 10 5B-Cascade 11 6A-Galena 12 6B-Cascade 13 7A-Galena 14 7B-Cascade 15 8A-Galena 16 8B-Cascade 17 9A-Galena 18 9B-Cascade 19 10A-Galena 20 l0B-Cascade 21 llA-Galena 22 llB-Cascade 23 12A-Galena 24 l2B-Cascade 25 13A-Galena 26 l3B-Cascade 1X4-pH 8 1X4-pH 8 1X4-neutral 1X4-neutral CuSO4 CuSO4 Cu(OAc)2 Cu(OAc)2 3X4-neutral 3X4-neutral Ca(OH)2 Ca(OAc)2 CuClPDF Image | PREPARATION OF LIGHT STABLE HOP PRODUCTS
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