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Extraction Solution 95% ethanol,Acid 95% ethanol 70% ethanol,Acid 70% ethanol DensityofExtract alpha/Iso-alpha-acid (g/rnl) in Extract (%) 0.81 80 0.99 67 1.04 90 1.02 80 methods have been used to chromatographically purify alpha-acids,beta-acids,andiso-alpha-acidsfromhopsorhop extract,inWhichvariousorganicsolventsandbufferingsolu tionsWereused.We departedfromthisconventionalmeth odology to retain the alpha/iso-alpha-acids on the resins by varying the a?inity of the e?luent and alloWed an elution of alpha/iso-alpha-acids-freeef?uent.Recombiningthealpha/ iso-alpha-acids-free ef?uent and the double extracted hop solid residues afforded a slurry. Evaporation of the aqueous ethanol and drying of the slurry afforded a less distinguish US 7,413,758B2 78 calreactionorreductiondi?icult,itWas decidedtoattempt the reduction or elimination of alpha/iso-alpha-acids in hop solids by extraction in a homogenous solution system. LoW molecular Weight alcohols, such as methanol or ethanol, are capable, With e?icient mixing, of extracting suf?cient amounts ofalpha/iso-alpha-acidsfromhop solids.Due tothe cost and potential toxicity of methanol, ethanol has been utiliZed.Inadditiontobeingsafeforconsumption,95% etha nolislesssolublefortheWater-solublecompounds andvery soluble for the alpha/iso-alpha-acids. An analytical scale extraction condition Was established by comparing the extraction e?iciency of acidic 95% ethanol, 95% ethanol, acidic 70% ethanol, and 70% ethanol, using Galena hop sol ids. Hop solids double extraction experiments Were under taken. To 200 grams of ground hop solids (the solid residue remaining after CO2 extraction of either Cascade hops or Galena hops) Was added 600 milliliters of 95% ethanol. The mixtureWasthenagitated,Withamagneticstirbar,forone hour, folloWed by vacuum ?ltration through a Whatman #4 ?lter paper. The ?ltrate Was retained. The extraction Was repeatedWithanother600millilitersof95% ethanol,andthe mixture Was again vacuum ?ltered through a Whatman #4 ?lter paper. The residues on the funnel Were Washed With an additional100millilitersof95% ethanol.Both?ltratesfrom the tWo extractions Were combined, and the residues Were collected. Results are shoWn in Table 1. TABLE 1 Extraction Ei?ciency Analyzed by HPLC Example3 Furthertreatmentofthedoubleextractedhop solidsliquid ?ltrate Was then undertaken. The treatment sought should selectively minimiZe alpha/iso-alpha-acids, but should also be mild and inert to the ?avor precursors. Hydrogenation, sodium borohydride reduction, caustic treatment, ion exchange, alkali metal and metal precipitation Were consid ered for the elimination of alpha/iso-alpha-acids, or for con versionofalpha/iso-alpha-acidsintolightstableforms(such astetrahydroiso-alpha-acids).Sodiumborohydridereduction ofiso-alpha-acidstorho-iso-alpha-acidsWaspossible,butthe subsequent removal ofundesirable boron compounds added extra steps and expense, and Was therefore considered ine?i cient. HoWever, both ion exchange, alkali metal or metal ion precipitation and hydrogenation shoWed promising results. The thus treated aqueous ethanol solutions Were recombined With the residues and the aqueous ethanol in the mixture Was thenremovedviaevaporationtoformareconstitutedlight stable hop product. The three successful methods are demon stratedhereinafter. Example4 An ion-exchangetreatmentofthedoubleextractedhop Although the acidic ethanol solutions are demonstrably more effective than neutral solutions, it is possible that the acidmay damagethe?avorelementsofhop solids,orinter fere With subsequent treatments. It is also noted that higher Water composition solvents co-extract more Water soluble compounds. For instance, a dark green color solution (With densityof0.99g/ml)Wasobtainedusing95% ethanol,While ayelloW-broWnishcolorsolution(Withadensityof1.02g/ml) Wasobtainedusing70%ethanol.InotherWords,atotalmass ofgreaterthan25% byWeightWasobtainedascomparedto 6% When theWatercompositionWas increasedto30% (70% ethanol/Water)from5% (95%ethanol)extractionofhopsol ids. The best results for the reduction and minimiZation of alpha/iso-alpha-acidsappearedtooccurinalesscomplicated 95% ethanol extract. 45 50 55 no light unstable alpha/iso-alpha-acids. TWotypesofionexchangeresins,BIO-RADTMAG 1X4 and 3X4, available from Bio-Rad Laboratories of Richmond, Calif.,USAWereused.DuetopKadifferences,thedissoci ated alpha/iso-alpha-acid ions exchange With these anions (Cl', OH“, and acetate ion) on the resins. The double extracted hop solids ?ltrate Was diluted With Water (either neutralorpH 8)toincreasea?initybetWeenalpha/iso-alpha acidsandresins.Ionexchangemaybeperformedoneithera column or batch basis. For convenience, a batch basis Was usedinourexperimentation.As aresult,theresidualalpha/ iso-alpha-acids Were signi?cantly reduced, as shoWn in Table 2, items 3, 4, 5, 6, 11, and 12. TWo BIO-RADTM anion exchange resins (AG 1X4, and 3X4,400mesh,chlorideform)Werepre-rinsedWithdistilled Water. The double extracted hop solids ?ltrate Was diluted With a 1:1 ratio of either distilled Water or a pH 8 buffer solution, and then added to the ion exchange resins at an amountof5%ofthetotalmixture.ThemixtureWasalloWed tomix foronehour,then?lteredthroughaWhatman #4 ?lter paper. This ?ltrate Was then mixed With the double extracted hop solids residues. The hop solids residues and the extracted ?avor precursors present in the ?ltrate Were simultaneously andhomogeneouslymixedWhiletheaqueousethanolWas evaporated offby a vacuum rotary evaporator. The resultant light stable hop product Was then dried for ?nal usage. Therefore, hop solids Were extracted using 95% ethanol until most of the alpha/iso-alpha-acids Were removed, and subjectedtothesubsequenttreatments.Thisusuallyrequired tWoconsecutiveextractions,andthehopsolidresiduesafter60 suchadoubleextractionusing95% ethanolstilretainmostof the potential Water-soluble ?avor precursors. This double extracted hop solid residue Was then adopted as a basic light stable hop product, and further treatment of the double extractedhopsolidsliquid?ltratefromthedoubleextraction65 to recover minor amounts of ?avor precursors Was consid ered. 20 25 30 35 40 ablehopproductthantheoriginalhopsolids,butcontaining solids?ltrateWasundertaken.A basicionexchangeresinhas been used in the past to separate alpha/iso-alpha-acids from methanolic, ethanolic, and hexane extract of hops. SuchPDF Image | PREPARATION OF LIGHT STABLE HOP PRODUCTS
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