Flavor Chemistry 风味化学.ppt

FlavorChemistryOctober7,2009YuanLiu,Orisit?,Mold,Dicoumarol(Coumadin),Coumarin,Majormetaboliteinman,Isithepatoxic?,1954FDABANSCOUMARIN,ReflectionsonaHalfCenturyofFlavorChemistry,1954-televisionscreensweresmallroundandblackaromaofdampblackearth,Nutty,brown,roasted,earthyandmusty,1950s1960s-Pyrazines,Todayabout60differentpyrazinesareemployedinflavorcreation,AdvancesinFlavoringMaterials,2-acetylthiazoleNutty,popcorn,bread,toastedcereal,2-isobutylthiazoleGreentomatoaromaandtaste;tomatoleafaroma,Sulfurolmeaty-beeflikewithnuttynote,2,4-Dimethyl-5-vinylthiazoleNutty,meatlikenotes,1950s1970sThiazoles,Todayabout45differentthiazolesareemployedinflavorcreation.,AdvancesinFlavoringMaterials,1950sMushroomalcohol(1-octen-3-ol),AlthoughfirstisolatedfromArmillariamatsutakein1937andLater(in1944)fromlavender,thismaterialwasvirtuallyunknowntomostFlavoristsuntilthelate1950s.,Naturalmushroomodor,slightlyfruity,Herbaceous,green,musty,Today,weknowthattheracematesodorisdominatedbytheolfactivelymorepowerful(-)-(R)-enantiomer.,AdvancesinFlavoringMaterials,beta-Pinene,Myrcene,Linalool,Geraniol,Citronellol,Citronellal,Menthol,LinalylAcetate,1959Bainfloral,truejasmin-like3*Ref:T.E.Acreeet.al.,J.Agric.Food.Chem.1985Methyldihydrojasmonates1R,2R-(-)-Floral,sweet,jasminelike240*1S,2S-(+)-Floral,fatty,cis-jasmone,haycharacter,15,360*teanote,slightlylemonpeellike(weak)1S,2R-(-)-epi-Herbal,fatty,tea-like,tobacco,12,500*-damascone,cis-jasmone1R,2S-(+)-epi-Intenselyfloral,jasmine-like,bright,cis-15*jasmone,slightlyfatty,woody,-ionone-like,extremelylonglastingRef:Werkhoff,P.,et.al.,FoodReviewsInternational,2002*detectionthreshold*recognitionthreshold,1964IntroductionofFuraneol,1965FirstpublicationsonisolationofFuraneolfromstrawberryandpineapple,AdvancesinFlavoringMaterials,1965-66-nograpefruitcharacter;virtuallynotaste,Threshold:60,000ppb800ppb,1968PfizerpatentsEthylmaltol,Ethylmaltol(VeltolPlus)wastoutedtobeabout6XstrongerthanmaltolandanimportantsubstituteforCoumarin.Well,atleastitisstrongerthanmaltol.,AdvancesinFlavoringMaterials,AdvancesinFlavoringMaterials,1960s-80sImportantmeatycompounds,2-methylthiophene-3-thiolCookedmeat,Ortho-toluenthiolMeaty,liver,2-methylfuran-3-thiolCookedmeat,2-methyl-4,5-dihydrofuran-3-thiolCookedmeat,DecadienalMeatmushroom-like,earthy,greentinge,AdvancesinFlavoringMaterials,2001TakasagosProfessorRyojiNoyoriwinsthe2001NobelPrizeforChemistry,AdvancesinFlavoringMaterials,AdvancesinanAmbergrisCompoundSynthesis,1950Synthesisof(-)-AmbroxfromSclareolviaSclareolide(90%(-)-Ambrox)1988IntroductionofDL-Ambrox(purelysynthetic)(50%(+/-)-Ambrox+50%diastereomers)1993IntoductionofCetalox(purelysynthetic)(96%(+/-)-Ambrox)2004Introductionof(-)-CetaloxLeavo(purelysynthetic)(99%(-)-Ambrox)presumablyviaresolutionofracemicSclareolideacidwithapseudoephedrineenantiomer,AdvancesinFlavoringMaterials,Mintlactone(1983),Dihydromintlactone(1995),Winelactone(1996),GRASNo.-37644032Odor:Vinous,lactonicMinty,coumarinic,Coumarinic,hay,(coconut)tenaciouslactonic,tonkaFlavor:Lactonic,sweet,herbalCoumarinic,fatty,Coumarinic,herballactonic,coconutThreshold*:0.0000016ppb0.00012ppb0.000039ppb*InairRef:Frerot,et.al.,FlavourFragr.J.,2002;17:218226;Gaudin,Tetrahedron,2000,56:4769-4776,Coumarinicp-MenthaneLactones,A5thtastesensationcalled“Umami”(akaUmani)isnowaccepted.MostcommonexampleisMSG(Monosodiumglutamate)whichenhancesmeat&savoryflavors.,TheFifthTaste,Until1999-2000only4tastesensationsweregenerallyrecognized:Sweete.g.Sucrose,AspartameSoure.g.Citricacid,Phosphoricacid(H+ions)Bittere.g.QuinineSaltySodiumChloride,Biotechnology&theFuture,In1955,Artificialflavoringscomprisedthevastmajorityofflavorsproduced.Asconsumermarketingbecamemoreimportant,adramaticshiftto“natural”flavoringsoccurredrequiringnewandimprovedmethodsfortheproductionofnaturalflavorchemicals.Biotechnologyintheproductionofmanymaterialsisnowcommonplace.But,thiswasonlythebeginning.,TheFutureisuponus.,2000/2001Identificationofcompletesetofhumanolfactorygenes(Lancet,et.al.WeizmannInstitute&Zozulyaet.al.Senomyx)March2002-cloningandcharacterizationofTRPM8&CMR1(coldandmentholreceptors)(McKemyet.al.UCSF&Peieret.al.Novartis)2002/2003characterizationofheterodimericreceptorsT1R2/T1R3(sweetreceptors)andT1R1/T1R3(umamireceptors)(Liet.al.Senomyx)2004EfficacyandPotencyofcoolingsensatesdemonstratedwithTRMP8coldreceptorusingthe(FLIPR)assay(Behrendtet.al.Grnenthal),Biotechnology&theFuture,Biotechnology&theFuture,WATCH,IdentifyingTasteEn