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Flavor Chemistry of Wine and Other Alcoholic Beverages PDF

332 Pages·2012·12.07 MB·English
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Flavor Chemistry of Wine and 1 0 g w0 bs.acs.or2-1104.f Other Alcoholic Beverages u1 p0 p://k-2 2 | htt021/b 11 y 16, 20doi: 10. 36 on Jul6, 2012 | 11 4.y 3.3Jul 9.16eb): 8W ded by Date ( wnloaation Doblic u P In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. 1 0 g w0 bs.acs.or2-1104.f u1 p0 p://k-2 2 | htt021/b 11 y 16, 20doi: 10. 36 on Jul6, 2012 | 11 4.y 3.3Jul 9.16eb): 8W ded by Date ( wnloaation Doblic u P In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. 1104 ACS SYMPOSIUM SERIES Flavor Chemistry of Wine and Other Alcoholic Beverages Michael C. Qian, Editor Oregon State University 1 0 g w0 Corvallis, Oregon bs.acs.or2-1104.f Thomas H. Shellhammer, Editor u1 p://pk-20 Oregon State University 2 | htt021/b Corvallis, Oregon 11 y 16, 20doi: 10. 36 on Jul6, 2012 | 11 4.y 3.3Jul 9.16eb): 8W ded by Date ( wnloaation Sponsored by the Doublic ACSDivisionofAgriculturalandFoodChemistry,Inc. P AmericanChemicalSociety,Washington,DC DistributedinprintbyOxfordUniversityPress,Inc. In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. LibraryofCongressCataloging-in-PublicationData Flavorchemistryofwineandotheralcoholicbeverages/MichaelC.Qian,editor,Oregon StateUniversityCorvallis,Oregon,ThomasH.Shellhammer,editor,OregonState UniversityCorvallis,Oregon;sponsoredbytheACSDivisionofAgriculturalandFood 1 Chemistry,Inc. 0 g w0 pages;cm.-- (ACSsymposiumseries;1104) bs.acs.or2-1104.f 1II.SncBWluNidn9ees7--8bF-il0ba-lv8ioo4gr1ra2an-p2dh7io9cda0ol-r3r-e-(fCaelroken.ngpcraeepssesaren)sd.2in.dWexi.ne--Chemistry--Congresses.3. Alcoholic pu01 beverages--Flavorandodor--Congresses. I.Qian,Michael,editorofcompilation.II. p://k-2 Shellhammer,ThomasH.,editorofcompilation.III.AmericanChemicalSociety.Division 2 | htt021/b oTfPA5g4r8ic.5u.lFtu5r5aFl5a3nd20F1o2odChemistry,sponsoringbody. 11 y 16, 20doi: 10. 663′.2--dc23 36 on Jul6, 2012 | 4.1y 1 ThepaperusedinthispublicationmeetstheminimumrequirementsofAmericanNational 3.3Jul Standard for Information Sciences—Permanence of Paper for Printed Library Materials, 9.16eb): ANSIZ39.48n1984. 8W ded by Date ( Copyright©2012AmericanChemicalSociety wnloaation DistributedinprintbyOxfordUniversityPress,Inc. Doublic oAfllthReiUgh.Sts.RCeospeyrrviegdh.tRAecptriosgarllaopwhiecdcfoopryinintegrnbaelyuosnedotnhlayt,pperromviidtteeddtbhyatSaepcteiro-ncsha1p0t7erofre1e0o8f P $40.25plus$0.75perpageispaidtotheCopyrightClearanceCenter,Inc.,222Rosewood Drive,Danvers,MA01923,USA.Republicationorreproductionforsaleofpagesinthis bookispermittedonlyunderlicensefromACS.Directtheseandotherpermissionrequests toACSCopyrightOffice,PublicationsDivision,115516thStreet,N.W.,Washington,DC 20036. Thecitationoftradenamesand/ornamesofmanufacturersinthispublicationisnottobe construedasanendorsementorasapprovalbyACSofthecommercialproductsorservices referenced herein; nor should the mere reference herein to any drawing, specification, chemicalprocess, orotherdataberegardedasalicenseorasaconveyanceofanyright or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce,use,orsellanypatentedinventionorcopyrightedworkthatmayinanywaybe relatedthereto. Registerednames,trademarks,etc.,usedinthispublication,evenwithout specificindicationthereof,arenottobeconsideredunprotectedbylaw. PRINTEDINTHEUNITEDSTATESOFAMERICA In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Foreword The ACS Symposium Series was first published in 1974 to provide a mechanism for publishing symposia quickly in book form. The purpose of the series is to publish timely, comprehensive books developed from the ACS sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare developed from symposia sponsored by other organizations when the topic is of 1 g w00 keeninteresttothechemistryaudience. bs.acs.or2-1104.f forapBperfoopreriaatgereaenidncgotmoppruebhleisnhsiavebocookv,etrhaegeparonpdofsoerdintatebrleesottfoctohneteanutdsieisncreev.iSeowmede u1 p://pk-20 papersmaybeexcludedtobetterfocusthebook;othersmaybeaddedtoprovide 2 | htt021/b caodmdepdr.eDhernasftisveonfecshsa.ptWersheanreappeperro-prerviaiteew,eodvperrvioierwtoofirnainltarcocdeupcttaonrcyecohrarpetjeercstioarne, 11 36 on July 16, 206, 2012 | doi: 10. aiannrecdlunmAdoaetsndaauciscncreurptilhtpeeet,dsv.oaonrleluymproeerspi.gariVnedaelribnraectsiamemarercerhap-rrpoeadapudecyrtsifoonarnsmdoafto.prirgeivniaolusrepvuiebwlishpeadpepraspaerres 11 4.y 3.3Jul 9.16eb): 8W ACSBooksDepartment ded by Date ( wnloaation Doblic u P In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Preface Aroma is one of the most important quality attributes for wine and many other alcoholicbeverages. However,thechemicalcompositionofmostalcoholicbeverages is so complex that it has always been a challenge for scientists to fully understand theirflavorchemistry. Thelowconcentrationofkeyaromacompounds,suchasthiols, thelowsensorythresholdofmanyimportantcontributorstoaromaandtheinterfering 1 bs.acs.org 2-1104.pr00 oianlfcsoiaghnhoatllsymtacbaiaotrluixtintmshtearukflmeaevthnoetraataicnocdnu,rflapataevrotairncupallryaerscliuysrsetohxretsregimnreeawltyeinrcehaacalcnleedsnsagilibcnioglih.toyWliociftbhLetCvhe-erMaagSdev,sannhecawes u1 beenachieved. p0 p://k-2 This book is derived from the American Chemical Society symposium “Flavor 12 | htt1021/b tChheepmuirsptoryseooffAslhcaorhinoglinceBwevinefroargmesa”tihoenldonotnhAeflugavuostr2c2h-e2m6i,s2tr0y1o0f,wininBeo,sbtoeenr,,ManAd,owthitehr n July 16, 20012 | doi: 10. oththeearAcaalsdceeocmhtioioclniaconbfdethrinvisderubasogtoreiksa.ilsPsdcaeirevtniocttiiepfidacntcotsotmhoefmflthuainvsiotsireyasm.npdoflsaiuvmorwpreerceusrcsoiernstiinstwsifnroemgrbapoeths o2 and their conversion in wine. This aspect is important because the origin of many 89.163.34.136 Web): July 16, vauanninnddieqaayucreeocaamurrdmoa.muplraaestcifouonrusanordresidnairwreeictnhteleycsiaenncflobenendcsaoerduyrbcmyedeetndavbirioerlcoittnleymsteoonfwtpailnnaedntgvsr,iattiphceeusilr.tubSriiaonltcrpearnathsceftoisceremairanotimtohnae d by ate ( Anothersignificantportionfocusesonagingprocessesduringwineproduction. eD adn Aging is a dynamic process involving both volatile and nonvolatile compounds. oo wnlcati During this process some compounds degrade, whereas other compounds form. Dobli Understanding these processes are of economic importance, particularly for wine u P sinceagingcanbesuchacriticalstepinitsproduction. This symposium book is a unique volume that describes the advances in flavor chemistry research related to alcoholic beverages. It will be an excellent reference bookforallscientistsandprofessionalsengagingintheresearchanddevelopmentin thefieldoffoodandbeverageflavoringandflavoringredients. Wearegratefultothe authorsfortheircontributionsaswellastothereviewersfortheirvaluablecritiques. MichaelC.Qian DepartmentofFoodScienceandTechnology,OregonStateUniversity 100WiegandHall,Corvallis,Oregon97331-6602 ThomasH.Shellhammer DepartmentofFoodScienceandTechnology,OregonStateUniversity 100WiegandHall,Corvallis,Oregon97331-6602 ix In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Editors’ Biographies Michael C. Qian MichaelC.Qian,Ph.D.,isafacultymemberatOregonStateUniversity. Hereceived hisB.S.degreeinChemistryfromWuhanUniversityofChina, hisM.S.degreeinFood Science from the University of Illinois at Urbana-Champaign, and his Ph.D. from the g 01 UniversityofMinnesotaundertheguidanceofDr. GaryReineccius. Dr. Qian’sresearch cs.or4.ot0 iinnvteorlevsitnsgatsOolrveegnotnlesSstasteamUpnlieveprrseitpyarfaotciouns osnucflhavaosrscohleidmipsthrayseanmdiicnrsot-reuxmtreancttailona,naslyosliids a0 bs.11 phase dynamic extraction, stir bar sorptive extraction, and fast GC, multi-dimensional p://pu2012- GC/GC-MS analysis of volatile aroma compounds. His research area has covered y 17, 2012 | httoi: 10.1021/bk- coaraorrosingpmtibrniaeba/rflulryrtaie,vosaonenrsadcrtcohshettrmhpaewaicpfibaeeelrl/rsdbryaioon)fc,dhflw1eai2mvnoebicroaaconlhkdgecemwhniiaensprteartyetgi.rorsaHnipneienshth,daebasiefipreyeurl,bpdalrionosfdhdefluhdcaotvmpso,sors.rmcHehateehlmlhafanirssu5tirm0tysapa(debneeldars-cairgknenbavileifiyertrcwiiaceenasdtl, NIV on Jul6, 2012 | d cpHhueebamllitsihshteBrdye.nbeHyfietthohefaSsAmpmareellrviFicorauunsiltCys,hcaeonm-deidcMaitilecdSrooV/cNoielaatnytio,l-eaennSdcualifpsusrauClftirooemnqupoeofnuAtncdstpsiveieankFFeoroooadtdC,noFatmliaopvnooanrleaannntsdd, RNELL Ueb): July 1 aiisnstceaurrnreraestenioatlrnycahslesmrcveiieenntgitnisagtss..vDiBcr.eeQfcohiraaenirhwoefacstahamefeAortgmorieacrcuacldthuearmiarlioaaf,nADdCrF.oSQoAdiagCnFhdsepFmelniastvt1roy0rDSyueivbairsDsioiivnnisionifodAnusCatnrSdy. OW by Cate ( d D nloadecation Thomas H. Shellhammer DowPubli ThomasH.Shellhammer,Ph.D.,istheNor’WesterProfessorofFermentationScience in the Department of Food Science and Technology at Oregon State University where he leads the brewing science education and research programs. His brewing research investigateshopsandbeerquality,hop-derivedbitternessanditsqualityassessment,and theoriginsofhoparomaandflavorinbeer. Hedirectsthebrewingeducationcomponent oftheFermentationScienceprogramatOSUandteachescoursesaboutbrewingscience and technology, beer and raw materials analyses, as well as an overview of the history, business, and technology of the wine, beer, and spirits industries. Dr. Shellhammer receivedhisPh.D.fromtheUniversityofCalifornia,Davisin1996.Duringthe2008−2009 academicyear,whileonsabbaticalleavefromOSU,heworkedattheTechnicalUniversity ofBerlinasaFulbrightScholarandAlexandervonHumboldtFellow.Dr.Shellhammeris amemberoftheBoardofExaminersfortheInstituteofBrewingandDistilling,London, England,aFellowoftheInstituteofFoodTechnologists,andtheChairmanoftheEditorial BoardoftheMBAATechnicalQuarterly. ©2012AmericanChemicalSociety In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Chapter 1 Spice Up Your Life: Analysis of Key Aroma Compounds in Shiraz M. J. Herderich,* T. E. Siebert, M. Parker, D. L. Capone, D.W.Jeffery,†P.Osidacz, andI.L.Francis 1 0 bs.acs.org 2-1104.ch0 †PTrheeseAntusatdradGlriealesnns:WOSsicnmheooRnolde,soeSfaAArcg5hr0i6Icn4u,slttAuituruest,ter,FaPoli.oaOd.aBnodxW19in7,e, u1 2 | http://p021/bk-20 Waite RGeslee*naEr-OcmhsamIinlo:sntmdit,auSrteko,uuTsth.hheAeruUdsentrriviacelhira@s,it5ay0w6or4fi.,AcAodmuesl.atariudalei,aPMB 1, 11 16, 20oi: 10. 36 on July 6, 2012 | d SeshsiernaztiailsfAorusptrraoldiau’csinmgoastuinmiqpuoertadnivterresditygroafperevdarwieintye, satnydleiss, 11 4.y includingsomeofAustralia’s‘icon’wines. Anecdotalevidence 9.163.3eb): Jul squugaglietystsAtuhsattraalsiapnicyS,h‘ipraezppweri’neasr.omDaeisspiimtepothrteanstigtonisfiocmanecheigohf 8W ed by Date ( aSrhoimraazctoomthpeouAnudsstrtahlaiatnarwetihneekseeyctcoor,nltirtitbleutiosrsktnootwhnepaebrocuetivtehde Downloadublication aScrohomimrapazouahnnadddrfleelasuvpdooeundrsiibodlfeenptfrioefirmcatihtuiimosndquiusntatilinilctyrtievSceehni‘rtpalyez.ppwIeinrn’et,hairasonmpdaapthiener P we summarise the untargeted metabolomics approaches and GC-MS-O experiments employed for the identification of key Shirazgrapeandwinesesquiterpenes,α-ylangene(Parkeretal. J. Agric. Food Chem. 2007, 55, 5948–5955) and rotundone (Wood et al. J. Agric. Food Chem. 2008, 56, 3738–3744). Therelativelyunknownsesquiterpenerotundonewasidentified as an important aroma impact compound in grapes, wine, and common spices with a strong spicy, peppercorn aroma. An aroma detection threshold of 16 ng/L in red wine indicates that rotundone is a major contributor to peppery characters in Shirazgrapesandwine,andtoalesserextentinwineofother varieties,andweexploresomefactorsthatinfluencerotundone concentrationsinwine. ©2012AmericanChemicalSociety In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012. Introduction Shirazisoneoftheworld’stopsixgrapevarietiesalongwithMerlot,Cabernet Sauvignon, Pinot Noir, Sauvignon Blanc and Chardonnay. The vineyard area planted to Syrah/Shiraz vines has grown from less than 10,000 hectares in the early1980stomorethan140,000hectaresin2004/2005. About50%ofShirazis growninFrance,and25%inAustralia,withArgentina,SouthAfrica,California, Chile, USA, Italy, New Zealand, Greece, Spain, Switzerland and other smaller producingcountriesaccountingfortheremainder. ShirazisAustralia’sfavourite redwinevariety,accountingfor51.4%ofthetotalcrushofredgrapesor25.8% oftotalwinegrapeproductionof1.6milliontonnesin2009/10(1). Shiraz (the name used by many New World producers for the grapevine 1 0 variety known as Syrah in France) is an ancient variety and is thought to have g h0 bs.acs.or2-1104.c e11m8030e2rAg.eDdTo(f2rod);matietM,wgoarnsadpaeelusssoearobenlaesntioclfhletuhsaeenddfirfDsotruvrweinzienaeivmnaartihkeeitniengsofrtrtoohmearrnroivRwehnôinrnoeAoVtueasdtlrleaSylhi,aircaianz. u1 p0 p://k-2 vines that have been planted in Australia more than 120 to 160 years ago in the 2 | htt021/b HanudntdeirveVrasleleayr,oVmiacstorraiangainndg tfhroemBaprlousmsa, bVearlrlieeys. aSndhircahzocwoilnaetes thoavliequinotreirceestainndg 11 16, 20oi: 10. istpsicoew,ndeoprenindibnlgenodnsthweitrhegCioanbse.rnSehtirSaazuivsiganvoenr,ywvietrhsaGtirleenvaacrhieetyanadndMiosuursveeddroen, 36 on July 6, 2012 | d ocmoroorVle-cioilnigmtneainetsere.lwyiflnPaerovsmo(ufiorneredne,txsapAmicupyslteraanlfidraonsmomSthheietriamAzedssetlmyaliiednsetyHinsitclyllulse,dseoorfetlMheegaarGngtra,armeptpeRpiapinveser)ry;, 11 89.163.34.Web): July i(ClBlouaosrntorasawstaeaVrthraaellorearyn,CgMelacorLefasVreeannlsleoVyray;lesa)wt,traeinebdtutcleehsaotcchooemlraymtya,onnmdlyuriscfcohuuwlnadirnaiennsdS(Hhriiuprnaetz-efrwruViinateelld,eFywi)g.inuTeroes d by ate ( 1comparesthesensoryprofilesgeneratedbyatrainedsensorydescriptivepanel Downloadeblication D othhfiegthwweroinienwfi‘nrpoeemsppfterhore’macroaoomcleoaro,Ml‘earsatrarginandrgeeatnRcwyiav’remarnerdreg‘gairocaindpie(t0-yg6’r.MoIwRni)cnowgnartsreagrsiatottenhde(3sSi)gh.niriCafizlceafarnrotllmyy, u theBarossaValley(06BV)hadsignificantlymore‘overallfruit’,‘darkfruit’,and P ‘jammyfruit’aromaandflavour. Despite the importance of Shiraz to the Australian wine industry, little was known until recently about the aroma compounds that are the key contributors to the perceived aroma and flavour of premium quality Shiraz wine. Anecdotalevidence,tastingnotes,andthebacklabelsofAustralianShiraz wine bottles suggested that a ‘spicy’, ‘pepper’ aroma is important to some high quality Australian Shiraz wines. The pepper character could be thought of as quintessentially Australian and possibly may even form part of the ‘terroir’ for a particular wine, yet the compound(s) responsible for this distinctive aroma in Shirazhadnotbeenidentified. Thusitwasimportanttoisolateandgainagreater understanding of such a powerful odorant that is present in grapes and wine in ourownbackyard. 4 In Flavor Chemistry of Wine and Other Alcoholic Beverages; Qian, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2012.

Description:
Content: PREFACE ; ANALYTICAL ; 1. SPICE UP YOUR LIFE: ANALYSIS OF KEY AROMA COMPOUNDS IN SHIRAZ ; M. J. HERDERICH, T. E. SIEBERT, M. PARKER, D. L. CAPONE, D. W. JEFFERY, P. OSIDACZ, AND I. L. FRANCIS ; 2. ANALYTICAL INVESTIGATIONS OF WINE ODORANT 3-MERCAPTOHEXAN-1-OL AND ITS PRECURSORS ; DIMITRA L.
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