Food Flavor 1 0 ubs.acs.org 8-0988.fw0 p0 http://bk-20 9 | 21/ 00 01 er 22, 2doi: 10. ctob08 | O0 on 0, 2 5.2 er 3 4b 2.m 2e 7.1ept 7S ed by Date: nloadation wc Doubli P In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. 1 0 ubs.acs.org 8-0988.fw0 p0 http://bk-20 9 | 21/ 00 01 er 22, 2doi: 10. ctob08 | O0 on 0, 2 5.2 er 3 4b 2.m 2e 7.1ept 7S ed by Date: nloadation wc Doubli P In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. ACS SYMPOSIUM SERIES 988 Food Flavor 1 ubs.acs.org 8-0988.fw00 ChemistrBy,i oSloegniscoarly A Ecvtiavliutya tion, and p0 http://bk-20 9 | 21/ 00 01 er 22, 2doi: 10. HirotoKsahgia wTaa Umnuivreras,it yE ditor ctob08 | O0 on 0, 2 Susan E. Ebeler, Editor 5.2 er 3 University of California 4b 2.m 2e 77.1Sept Kikue Kubota, Editor ed by Date: Ochanomizu University nloadation Dowublic Gary R. Takeoka, Editor P Agricultural Research Service, U.S. Department of Agriculture Sponsored by the ACS Division of Agricultural and Food Chemistry, Inc. American Chemical Society, Washington, DC In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. Library of Congress Cataloging-in-Publication Data Food flavor: chemistry, sensory evaluation, and biological activity / Hirotoshi Tamura... [et al.], editor; sponsored by the ACS Division of Agricultural and Food Chemistry, Inc. p. cm.—(ACS symposium series ; 988) Includes bibliographical references and index. 01 ISBN 978-0-8412-7411-2 (alk. paper) pubs.acs.org 08-0988.fw0 F1Il..a TFvaoomor—du—rCaB,o Hniogitrreoectshosnsehso..l o4IgI. y.F —AomoCdeor naicngaranelys Cssieshs—e. mC2i.oc Fanlgo roSedos—csieesSt.ye .n5 sD.o Firvoyio seidvo anal udoadft iAitoigvnre—isc—uClCtounorgnargle rasesnssdsees s.F . o3o. d http://bk-20 Chemistry, Inc. 9 | 21/ TP248.65.F66F695 2008 00 664'.072—dc22 01 er 22, 2doi: 10. The paper used in this publication meets the m2in00im70u6m05 9r1e quirements of ctob08 | American National Standard for Information Sciences—Permanence of Paper on O0, 20 for Printed Library Materials, ANSI Z39.48-1984. 5.2 er 3 Copyright © 2008 American Chemical Society 4b 2.m Distributed by Oxford University Press 2e 7.1ept All Rights Reserved. Reprographic copying beyond that permitted by Sections ed by 7Date: S tC1h0lae7ta roaar np c1ee0r- 8cCh oaefnp ttteehrre, fUeIne.Sc ..o , Cf 2o$2p42y0 r.2igR5ho tsp eAlwucost o i$ds0 a.7Dll5orw ipveeedr, pfDoaargn ievn etiersrs n,p aaMli duA steo 0 1othn9e2ly 3,C , pUorpoSyvAriidg. ehdt wnloadcation uRnedpeurb lliiccaetniosne forro rmep AroCdSu.c tDioinre fcotr t hsaelsee oafn pda gotehse rin p tehrims ibssoiookn irse qpueersmtsit tteod AonClSy Doubli Copyright Office, Publications Division, 1155 16th Street, N.W., Washington, P DC 20036. The citation of trade names and/or names of manufacturers in this publication is not to be construed as an endorsement or as approval by ACS of the commercial products or services referenced herein; nor should the mere reference herein to any drawing, specification, chemical process, or other data be regarded as a license or as a conveyance of any right or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce, use, or sell any patented invention or copyrighted work that may in any way be related thereto. Registered names, trademarks, etc., used in this publication, even without specific indication thereof, are not to be considered unprotected by law. PRINTED IN THE UNITED STATES OF AMERICA In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. Foreword The ACS Symposium Series was first published in 1974 to pro vide a mechanism for publishing symposia quickly in book form. The purpose of the series is to publish timely, comprehensive books devel 01 oped from ACS sponsored symposia based on current scientific re ubs.acs.org 8-0988.fw0 oaseuthadericre hno.c reOg. acncaizsaiotinoanlsl yw, bhoeno ktsh ea reto dpeicv eislo opfe dk eferonm in styermespto tsoia tshpeo cnhsoermedis tbryy p0 http://bk-20 Before agreeing to publish a book, the proposed table of con 9 | 21/ tents is reviewed for appropriate and comprehensive coverage and for 00 01 interest to the audience. Some papers may be excluded to better focus ctober 22, 208 | doi: 10. tachphepa prbotoeprorsika ;at ero,e t hopevereesr r-vmrieaevywi e bwoere daid npdtrreoidod rut octo to prfryion vacli hdaaecp ccteoerpmst apnarrecehe eanodsrd ivreeedjn.e ecsDtsir.o anWf,t sha neodnf O0 on 0, 2 manuscripts are prepared in camera-ready format. 5.2 er 3 As a rule, only original research papers and original review 4b 22.em papers are included in the volumes. Verbatim reproductions of previ 77.1Sept ously published papers are not accepted. ed by Date: nloadation ACS Books Department wc Doubli P In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. Preface The investigation of nature is an infinite pasture-ground where all may graze, and where the more bite, the longer the grass grows, the sweeter is its flavor, and the more it nourishes. 1 org pr00 Aldous Huxley s.8. c8 s.a09 09 | http://pub021/bk-2008- wexipll otnheen Atiinsa vlw esget rinogeawattirho tnhsie n o efin dfdeo nootdfi f tihacnea dtf iiobrnset v doerefa cgnaede wef l oafvf ltoahrve o le2r a1dcst? oc meCnpetourturayni,dn slw,y h, eethrxee 01 October 22, 2008 | doi: 10. ppseoeprsiaserinbactlieeo dnh advsuecr iienlengdc teht oet ht1ha9et 7 rm0esal adatneivd e idl1ye9 n8mt0iasft,i ucharaetis o fnisel olodwfs eotdhf.e gAsaens dn ctehhwer oamcdoavmtaonpgcoreauspn hdinys on 0, 2 and high-performance liquid chromatography. However, the pasture- 5.2 er 3 ground for new discoveries is still growing and nourishing new flavor 2.4mb chemists and new developments in flavor chemistry. These proceedings, 2e 7.1ept based on a symposium held at the Pacific Region of the American 7S nloaded by ation Date: Cestxhacneedmlilniecgnastl eoSvf iofdlceainvectoyer cfihnoe r mDthiesect erfymu. tbuerre 2g0ro0w5,t h ina nHd othneo lunleue,d sH faowr aniie wp rouvniddeer wc Doubli In the first section of this book (Chapters 1-4) the focus is on P new and improved approaches for identifying and quantifying flavor compounds. At the time of the symposium and publication of this proceedings, we are well into the "-omics" (including metabolomics) era of science; the need to rapidly measure large numbers of compounds simultaneously while still providing the selectivity and sensitivity needed to measure flavor compounds present in low ppb and ppt levels is pushing analytical chemists to the limits of the currently available technology. As shown in these chapters, developments in multi dimensional separations, new chromatographic stationary phases, diverse sensors for rapidly detecting multiple compounds, and the ability to xi In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. quantitatively measure interactions between flavors and matrix com ponents are among the areas of current and future development. Flavor chemistry and formation are the focus of the next two sections (Chapters 5-16). Understanding how agricultural practices and food processing conditions affect the synthesis and degradation of flavors is of growing interest as scientists and consumers continue to recognize that conditions which provide the most stable products for storage or transportation are not always the same as those conditions that provide the maximum desirable flavor qualities. New food sources for modern consumers, often based on foods of indigenous diets, also continue to contribute to increasing diversity of flavors and unique 1 chemistries. Finally, identification of genes and enzymes involved in g 00 orpr flavor formation in foods, such as strawberries, will lead to improved s.8. s.ac098 varieties of fruits and vegetables as well as coming full circle to 9 | http://pub21/bk-2008- icgmoennpderosit viaoinnndgs eocnuazrny mubneeds eforosprtt aiinmmdipiznreogdv eotodf fhlmaovawox ri amagtirtzirceibu eultxtueprsra.e ls asinodn foanodd parcoticveistsyi nogf 0010 Although flavor chemists have often previously focused on October 22, 2008 | doi: 10. aosefr en fscloaurvryor erp nrcotlopyme trrptyioeiusn ngod tfso i ncadhdiadvnriegdseussa la arceso muan pdfoueunrnscdttaisno, dnthi neog fc hhinaotlweler anscegtneisoso ntrhsy a wtp esitcrhci eenoptttihisoetnrs on 0, 2 flavor compounds and with other nonvolatile matrix components. The 5.2 er 3 fourth section of these proceedings (Chapters 17-21) focuses on these 4b 2.m complex interactions as well as on the sensory factors that influence 2e 7.1ept consumer choice in selecting foods with maximal nutritional value. 7S nloaded by ation Date: rteencodgs ntiot Finoinon ta tlohlyna,lt y it nha etch tebiv iolaatlsiootg nis ceoacflt isaoecnnt si(ovCrihytya rpoetfce erepss tso2er2ns-t i2fa3ol r) o, tiatlhsse teare,n dair so filmnacvaro,e rcasos lieonxrg, wc Doubli and mouthfeel, but also that many flavor compounds can also provide P beneficial health effects in preventing degenerative diseases such as heart disease and cancer. We hope that readers of these proceedings will come to agree with Aldous Huxley that the investigation of flavor chemistry is an infinite pasture-ground that continues to thrive and provide new insights and challenges for analytical chemists, food scientists, biochemists, and geneticists working toward the common goal of understanding and improving food and beverage flavor. We also hope that these chapters may provide inspiration to a new generation of scientists who will grow and expand the field even further. xii In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. Acknowledgments The symposium and book would not have been possible without the financial support of: The ACS Division of Agricultural and Food Chemistry, Inc., Firmenich SA, Japan Tobacco Incorporated, Ogawa & Company, Ltd., Suntory Ltd., Takasago International Corporation, Takata Koryo Company, Ltd., and T. Hasegawa Company, Ltd. We are grateful for their generous contributions. Hirotoshi Tamura 1 Department of Biochemistry and Food Science g 00 orpr Kagawa University s.8. s.ac098 2393 Miki-Cho 9 | http://pub21/bk-2008- KKJaiaptgaaa-nGw ua n7 61-0795 00 01 ober 22, 28 | doi: 10. DSuepsaarntm Een. tE obfe Vleitri culture and Enology Oct00 University of California on 0, 2 One Shields Avenue 5.2 er 3 Davis, CA 95616 4b 2.m 2e 7.1ept Kikue Kubota 7S nloaded by ation Date: DLOaecbphoaarrntaomtmoerniyzt uoo fUf FNnoiuovtder riCstiihotyen m anisdt rFy ood Science wc Doubli 2-1-1 Otsuka P Bunkyo-ku Tokyo 112-8610 Japan Gary R. Takeoka Western Regional Research Center Agricultural Research Service U.S. Department of Agriculture 800 Buchanan Street Albany, CA 94710 xiii In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. Chapter 1 Comprehensive Two-Dimensional Gas Chromatography: Application to Aroma and Essential Oil Analysis M. D. R. Gomes da Silva1, Z. Cardeal2, and P. J. Marriott3,* 1 g 00 orch 1REQUIMTE, Departamento de Química, Faculdade de Ciências e s.8. s.ac098 Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal ub8- 2Chemistry Department, ICEx, Federal University of Minas Gerais, p0 09 | http://021/bk-20 3 ASAcuivsetenrnacieldisaa,n AR CMnetonITntri Uoe fnCoiavrre Rlrosesist e6ya6,r G2c7hP,3 Oo1 n2B 7So0exp- 92a40r7a16t iBVoen lM oS eHclibeonorucizeron,n Setc e3h,0 o0Mo1lG Ao, fuB Asrtaprzapilllii aed 01 er 22, 2doi: 10. Corresponding author: [email protected] ctob08 | O0 on 0, 2 5.2 er 3 4b 2.m 7.12epte Comprehensive two-dimensional gas chromatography (GC×GC) 7S is a powerful analytical tool that can be applied to food and ed by Date: essential oil samples to enhance separation capacity and spectral nloadation rbeestotelurt iopena kc aidpeanbtiilfiitciaesti.o nT hasissi gannmaleyntitcsa lw hteecnhn uiqseude ianl staon daellmow ws ith wc Doubli spectrometric detection systems by means of fewer interferences P and thus true mass spectra of the individually isolated compounds in the 2D space. The development of more accurate and sensitive quantification methodologies permit improved characterization of complex samples, or target compounds in complex matrices. New approaches to isolation of aroma compounds from the matrix, for olfactory assessment based on targeted multidimensional GC are possible. © 2008 American Chemical Society 3 In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008. 4 Aroma Analysis: Sampling, hyphenated separations and the multidimensional approach Flavor results from compounds that are divided into two broad classes of compounds: those that are responsible for taste and those that are responsible for odors, the latter designated as aroma compounds. The matrix can affect perception of the odor and taste (1). The compounds that are considered as aroma substances are primarily those that are present in the matrix or sample headspace in concentrations higher than the odor and/or taste threshold. Essential oils are mainly obtained by steam distillation or simultaneous g 001 distillation extraction where temperature and pressure are carefully selected in orch order to avoid, as far as possible, loss of volatile compounds by thermal s.8. s.ac098 decomposition, oxidation or hydrolysis (2, 3). Microextraction procedures have ub8- been developed in order to analyze trace levels of certain important taste- and odor- p0 9 | http://21/bk-20 cfsroaeuliesd i nmpghe ctahosomed pm fooiucrnr ohd-esea xidntsr pwacaatctieoer na ( n(4Sa)lPy.M sTisEh w)e i(nt5ho)v ,t ehhle aa svn aabrleyiecttiocyma ole fs ccaao lpaeto ehpdeu alfadibrs,ep rassic meof ptfeleecr,hi nsnogiql vsuoeemn ote f 00 01 October 22, 2008 | doi: 10. ded(SqaeBtugairSl eihEbear) ni oudwfml ain sssag im dtiuespav tlrieieonlqongups ie rsiedesdl ep.(c 7oAt)sinv,s iiaibtnynlce.a r lWeo(6ags)hoi,iun lcssgat rmteqhfeuueta hl novetodixfl piuncemaarmtieimoe neodn f ts iattnhilr e peb rqasouorc irelspdiobtuirrvprieeuti vmapen h aedanxs edptr.r a uncTdtoiehonnin-st on 0, 2 technique has also been applied to flavor analysis, after thermal desorption of the 5.2 er 3 coated bar prior to GC or multi-dimensional GC analysis (8-10). 4b 22.em Essential oils are very complex samples that constitute volatile compounds 7.1ept (less than 100 u) to semi-volatile compounds (around 300 u). Those samples are 7S ed by Date: moro stlliyn ecaorm pstrriuscetdu roefs ,t erpveanriooiuds codmegproeuensd s,o wf huicnhs apturerasteinont ,m asnuyb sitsiotumtieornics, c yacnlidc nloadation oxygenated moieties, that produce similar or identical mass spectra, normally DowPublic ctihmroem waitnodgorawph (i1c1al)l ya nads stohcuiast eadp pwroipthriiant ec ocmolpulmexn gprhoauspes sienle cat inoanr,r oinwje crteitoenn tiaonnd detection system choice are usual analytical criteria (12). Hyphenation of the GC separation step with spectroscopic techniques is often required for absolute component identification. Thus high resolution GC (HRGC) in tandem with Fourier transform infrared (HRGC-FTIR) is a very powerful identification tool. Nevertheless it demands very high solute concentrations and quantitative component separations for collection of sufficiently clean spectra (13). HRGC- MS is nowadays the most popular hyphenated technique aimed towards the characterization and identification of complex volatile sample constituents. Nevertheless, notwithstanding the continuous development of instrumentation, techniques and analytical methods in the field of GC and MS, total separation of all the compounds of a mixture and their unique identification is still either impractical or physically unachievable because of the high sample complexities In Food Flavor; Tamura, H., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2008.
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