Sulfur Compounds in Foods

303 Pages·1994·22.58 MB·English

by  Cynthia J. Mussinan and Mary E. Keelan (Eds.)

ACS SYMPOSIUM SERIES 564
Sulfur Compounds in Foods
1 Cynthia J. Mussinan, EDITOR
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w International Flavors & Fragrances
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99 Mary E. Keelan, EDITOR
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b International Flavors & Fragrances
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pubs.acs.y 29, 199
2 | http://Date: Jul Developed from a symposium sponsored
y 15, 201blication by the Diviastio thn eo 2f 0A6gtrhic Nulattuioranla al nMde Feotiondg Chemistry
Jul Pu of the American Chemical Society,
Chicago, Illinois
August 22-27, 1993
American Chemical Society, Washington, DC 1994
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
Library of Congress Cataloging-in-Publication Data
Sulfur compounds in foods / Cynthia J. Mussinan, editor, Mary E.
Keelan, editor.
p. cm.—(ACS symposium series, ISSN 0097-6156; 564)
"Developed from a symposium sponsored by the Division of
Agricultural and Food Chemistry at the 206th National Meeting of the
American Chemical Society, Chicago, Illinois, August 22-27, 1993."
Includes bibliographical references and indexes.
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w ISBN 0-8412-2943-0
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6 1. Food—Composition—Congresses. 2. Sulphur compounds—
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0 Congresses. 3. Flavor—Congresses.
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19 I. Mussinan, Cynthia J., 1946- . II. Keelan, Mary E., 1965- .
k- III. American Chemical Society. Division of Agricultural and Food
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1/ Chemistry. IV. American Chemical Society. Meeting (206th: 1993:
02 Chicago, Ill.) V. Series.
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1 TX511.S85 1994
oi: 664—dc20 94-20826
org 4 | d CIP
pubs.acs.y 29, 199 The paper used in this publication meets the minimum requirements of American National
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PRINTED IN THE UNITED STATES OF AMERICA
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
1994 Advisory Board
ACS Symposium Series
M. Joan Comstock, Series Editor
Robert J. Alaimo Douglas R. Lloyd
Procter & Gamble Pharmaceuticals The University of Texas at Austin
Mark Arnold Cynthia A. Maryanoff
University of Iowa R. W. Johnson Pharmaceutical
Research Institute
David Baker
University of Tennessee Julius J. Menn
Western Cotton Research Laboratory,
01 Arindam Bose U.S. Department of Agriculture
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w Pfizer Central Research
4.f Roger A. Minear
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05 Robert F. Brady, Jr. University of Illinois
94- Naval Research Laboratory at Urbana-Champaign
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b Margaret A. Cavanaugh Vincent Pecoraro
1/
2 National Science Foundation University of Michigan
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0.
oi: 1 Arthur B. Ellis Marshall Phillips
org 4 | d University of Wisconsin at Madison Delmont Laboratories
pubs.acs.y 29, 199 DLeehnignhi sU nWive. rHsiteys s NGoerothrg Cea rWolin. aR Sotbaeter tUsn iversity
2 | http://Date: Jul HIBiMro Ashlmi aIdteon Research Center AM.a cTarlausmtera Cno Sllcehgew artz
y 15, 201blication MUnaivdeersleitiyn oef MPe.n Jnsoyulvlalineia JUonhivner sRity. Sohf aIlplilneoyis
Jul Pu Lawrence P. Klemann at Urbana-Champaign
Nabisco Foods Group L. Somasundaram
DuPont
Gretchen S. Kohl
Dow-Corning Corporation Michael D. Taylor
Parke-Davis Pharmaceutical Research
Bonnie Lawlor
Institute for Scientific Information Peter Willett
University of Sheffield (England)
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
Foreword
iHE ACS SYMPOSIUM SERIES was first published in 1974 to
provide a mechanism for publishing symposia quickly in book
form. The purpose of this series is to publish comprehensive
books developed from symposia, which are usually "snapshots
in time" of the current research being done on a topic, plus
some review material on the topic. For this reason, it is neces
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0 sary that the papers be published as quickly as possible.
w
4.f Before a symposium-based book is put under contract, the
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05 proposed table of contents is reviewed for appropriateness to
94- the topic and for comprehensiveness of the collection. Some
9
k-1 papers are excluded at this point, and others are added to
b
1/ round out the scope of the volume. In addition, a draft of each
2
10 paper is peer-reviewed prior to final acceptance or rejection.
0.
1 This anonymous review process is supervised by the organiz
oi: er^) of the symposium, who become the editor(s) of the book.
org 4 | d The authors then revise their papers according to the recom
pubs.acs.y 29, 199 mcaemnedraat-iroenasd yo cf opbyo,t ha ntdh esu bremviietw theres fiannadl ptahpee rse dtioto rths,e perdeiptoarrse,
2 | http://Date: Jul vwiehwo cAphsae pcaek r rstuh alaert,e a olinnl lncyleu codersesidgai rniyna lrt herveeis seviaoornlcushm h eapsva.ep ebVresee rnabn amtdiam od reri.eg pinraodl urec
y 15, 201blication tions of previously published papers are not accepted.
Jul Pu M. Joan Comstock
Series Editor
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
Preface
IHE CONTRIBUTION OF SULFUR COMPOUNDS to the flavor and off-
flavor characteristics of foods has been studied for many years. Advances
in analytical techniques and instrumentation and mechanistic studies have
led to a better understanding of the formation and mode of action of
these compounds. Recent interest, however, has focused on their impor
tance in areas other than flavor. The role of dietary sulfur compounds as
1 anticarcinogens, antimicrobials, and antioxidants has been and continues
0
pr0 to be extensively studied.
64. Although each of the afore-mentioned areas could itself be the sub
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4-0 ject of a book, the purpose of this book is to provide an overview of the
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9 entire subject. Various chapters discuss the organoleptic characteristics,
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k- analysis, formation, and functional properties of this important class of
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21/ compounds.
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0.1 We would like to thank everyone who contributed to the success of
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oi: the symposium upon which this book is based. We would also like to
pubs.acs.org y 29, 1994 | d KtnEholraawannfltk,e, d aGgonueidv ra t Mhucedhc aaCfnpiont-reRamrno iuccaikruae.t l,h soHurpesrp soahrnetyd , o rfIe nvttiheeewrn eafrotsil.ol onwaFilni ngFa lllacyov, mowrpsea n&gier saF:t reafDuglrrlaayng coaeccsok,,
2 | http://Date: Jul CYNTHIA J. MUSSINAN
y 15, 201blication IR1n5e1tse5eran Hractihigoh n&wa alD yFe lv3aev6loo prsm &en Ft ragrances
Jul Pu Union Beach, NJ 07735
MARY E. KEELAN
International Flavors & Fragrances
800 Rose Lane
Union Beach, NJ 07735
March 23, 1994
ix
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
Chapter 1
Sulfur Compounds in Foods
An Overview
1Cynthia J. Mussinan and 2Mary E. Keelan
1International Flavors and Fragrances, Research and Development,
1515 Highway 36, Union Beach, NJ 07735
2International Flavors and Fragrances, 800 Rose Lane,
Union Beach, NJ 07735
01 The importance of sulfur compounds to the flavor and off-flavor
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h characteristics of foods is well known and continues to be stud
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64. ied. Mechanistic studies have led to a greater understanding of
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4-0 the formation and mode of action of these compounds. Re
99 cently, however, more attention has been given to some of their
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k- non-sensory characteristics, particularly to their antimicrobial
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1/ and anticarcinogenic effects.
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y 15, 201blication vcuegrreetnacbele so,f dsauilrfuyr p croodmupcotsu nedtcs. ,i na sf owoedlsl awso iunl dh ebaete cdo mfopoldeste. wNioth doiusct umsseinotnio onf o thf eth oecir
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reviews of the literature concerning the role of thiazoles, thiophenes, and thiols in
food flavor through 1975 can be found in Maga's series of review articles (3-5).
Sensory Properties
While the occurrence of sulfur compounds is of interest, their sensory properties
can be critical to the flavor of a food. According to Boelens and van Gemert (2)
"most of the volatile sulfur compounds are essential constituents of the material.
That means they are necessary for the sensory quality, but that they are not charac
teristic. A small number of the sulfur compounds, however, are characteristic com
pounds..." These compounds, by themselves, can be recognized as having the same
0097-6156/94/0564-0001$08.00/0
© 1994 American Chemical Society
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
2 SULFUR COMPOUNDS IN FOODS
basic organoleptic character as the material. They are the so-called character-
impact compounds. Examples are shown in Table I. Since some of these com
pounds have extremely low threshold values, they can be important to the flavor of
a food at the ppb level. For example, one of the compounds reported in onion, pro
pyl propane thiosulfonate, has a powerful and distinct odor of freshly cut onion
(14). Since the threshold of this compound (1.5ppb) is several hundred times lower
than its concentration (0.5ppm), it undoubtedly makes a significant contribution to
the overall onion flavor (75).
Table I. Character-Impact Sulfur Compounds
01 Food Comoound Reference
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h
c Bread 2-acetyl thiazoline 6
4.
6
05 Cabbage dimethyl sulfide 7
4-
99 Coffee furfuryl mercaptan 8
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bk- Grapefruit 1 -p-menthene-8-thiol 9
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02 Passionfruit 2-methyl-4-propyl-1,3-oxathiane 10
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oi: 1 Potato methional 11
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2 | http://Date: Jul foods, Athletyho huagvhe saulslfou rb eceonm ipmoupnlidcast eadre i nim opffo-rftlaavnot rc odnetvrieblouptomrse ntot (tCheh ifnl aavnodr Loifn mdsaanyy,
y 15, 201blication fCsomhoaadlp.l t eqru E8avn, etNintia eisrinn c eatn m ahle.a,a vtCe h waahp deteerrele 7tes)ru.i olfBuuser ceacfuofsemcetp t ohouenny d thhsa ev aeor ersg uavcnehor lyleo pwitmi ctph corhersatahrnaoctl dtestro, oontfhl aye
Jul Pu organoleptic character, high levels of volatile sulfides can form undesirable flavors
(76). Although hydrogen sulfide may be important to the aroma of various fresh
citrus juices, dimethyl sulfide has been implicated in off-flavors in canned orange
and grapefruit juices. The latter compound probably comes from heat degradation
during processing (77). Hydrogen sulfide, dimethyl sulfide, and dimethyl disulfide
have been associated with the cooked, cabbage-like, sulfurous odor and flavor that
occurs when milk is heated. This undesirable character develops during ultra-high-
temperature (UHT) sterilization, but typically disappears after several days of stor
age (18).
Analysis
The minute quantities of sulfur compounds found in many foods makes their analy
sis and quantitation a challenging problem. Extraction without further
fractionation, will, in many cases, not result in a high enough concentration of
these trace sulfur constituents to permit their identification by gas chromatogra-
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
1. MUSSINAN AND KEELAN Sulfur Compounds in Foods: An Overview 3
phy/mass spectrometry (GC/MS). Element-selective detectors are useful tools for
quickly locating sulfur compounds in complex mixtures and for monitoring their
presence through subsequent isolation and fractionation steps (79, Mistry et al.,
Chapter 2). The most commonly used sulfur detector is the flame photometric de
tector (FPD) (20). More recently, a new chemiluminescence detector (SCD) was
developed for GC (27, Steely, Chapter 3). The SCD is reported to be sensitive, se
lective and linear. In a 1988 applications note (22), dimethyl sulfide was deter
mined in beer by headspace analysis without any preconcentration. Levels of this
compound in beer are typically l-1000ppb. Atomic emission detection (AED) has
recently been commercially developed for gas chromatography. The AED can be
tuned to selectively detect any element in any compound that can be eluted from a
GC (23). Using these detectors as guides, the analyst can target those fractions or
areas of a chromatogram containing sulfur for careful analysis by GC/MS or other
01 hyphenated techniques like supercritical fluid chromatography/mass spectrometry
0
ch (SFC/MS).
4.
6
5 Artifacts
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9 When attempting to analyze for sulfur constituents, the possibility of artifact forma
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1
k- tion must be carefully considered (Block and Calvey, Chapter 6; Spanier et al.,
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1/ Chapter 5). Many sulfur compounds are thermally unstable. Therefore, it's not
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10 surprising that the high temperatures typically encountered in the inlet of a gas
10. chromatograph can lead to artifact formation. As Block (24) pointed out, many of
oi: the thiosulfinates and related sulfoxides found in garlic and onion are thermally un
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y 15, 201blication tmheeithr osdtsa bsiulictyh. a sI nli qcuaisde csh wrohmeraeto ginrasptahbyil iotyr NisM eRvi dneeendt, taol tberen uastievde., low-temperature
Jul Pu Formation
The mechanism of formation of sulfur compounds has also been studied in depth,
either directly, or using model systems (Tressl et al. Chapter 18). Nonvolatile pre
cursors to volatile sulfur compounds in foods are the sulfur containing amino acids
(cysteine/cystine, and methionine), reducing sugars, and thiamin (vitamin Bl). The
amino acids and reducing sugars react in the so-called Maillard reaction first de
scribed by L.C. Maillard in 1912 (25) and since extensively studied (26). The di-
carbonyls which form during this reaction catalyze the Strecker degradation of cys
teine to mercaptoacetaldehyde, acetaldehyde, hydrogen sulfide and other
compounds (27). Similarly, the Strecker degradation of methionine produces me-
thional which further hydrolyzes to methyl mercaptan and hydroxypropionalde-
hyde. The volatile sulfur compounds, hydrogen sulfide and methyl mercaptan, are
highly odored and quite reactive. Both will readily react with carbonyl compounds
and carbon-carbon double bonds to yield many potent flavor compounds (28). In
addition to the Maillard reaction which involves a thermal degradation, methionine
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
4 SULFUR COMPOUNDS IN FOODS
may degrade by enzymatic means to form dimethyl sulfide, another very powerful
flavor compound (28). These small, reactive molecules may serve as precursors for
other sulfur containing flavor compounds. For example, hydrogen sulfide may re­
act with furanones leading to the formation of sulfur containing heterocycles (29).
Methanethiol may also further react forming mono-, di- and trisulfides (29). The
thermal degradation of thiamin (vitamin Bl) provides another source of sulfur con­
taining flavor compounds, many of them heterocyclic (30', Guntert et al., Chapter
Π).
Functional Properties
While the sensory properties of sulfur compounds have been of interest for many
years, recent attention has focused more heavily on some of the other functional
properties of these compounds. Certain sulfur compounds have been found to have
1 antioxidative, antimicrobial, and human medicinal properties.
0
0
h
c Antioxidative Properties. When cooked meat is refrigerated, a rancid or stale fla­
4.
56 vor usually develops within 48 hrs. This character has been termed "warmed-over
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4- flavor"(WOF) and is generally attributed to the oxidation of lipids. Various syn­
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19 thetic and natural antioxidants have been used to reduce the development of WOF.
bk- Among the natural antioxidants used are the sulfur containing amino acid cysteine,
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2 and various Maillard reaction products. Eiserich and Shibamoto (Chapter 20)
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0.1 found that certain volatile sulfur heterocycles derived from Maillard reaction sys­
1
oi: tems can function as antioxidants.
pubs.acs.org y 29, 1994 | d ttaih oimonl orsed soeNunlal tftibounrrrgoa fw lir nupn hiithtne gejnu .of iTlocsreh m oepa fhp tiweroenhnsoei tlnosecf, egaC rnaoil pulfei necsdry seus stnaeidrnianedbre gl Seoo i bnrb rggorlolweuwttonann tcih noi(og3lon7 rre)e. aswUcttuasiodisnni egfsod cu dantuhfdfreei n itcegof fareocecxiddtiu d ocaafes­
2 | http://Date: Jul tMhee doixciidnaatlio Pn roofp cearftfieeisc. acAidcc, othrduisn gp rtoote cLtainwgs oitn fr (o3m2), b rgoawrlnicin igs. one of the most re­
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have focused on its organosulfur compounds because studies have shown that re­
moval of the thiosulfinates eliminates many of these effects. Almost all human
studies on the lipid-lowering effects of garlic and garlic products showed signifi­
cant decreases in serum cholesterol and serum triglyceride. Reports that onion and
garlic contain hypoglycemic (blood sugar reducing) agents go back about 50 years.
In fact, the ancient literature reveals their use in treating diabetes (33).
Garlic, and to a lesser extent onion, have been found to possess antimicro­
bial properties. They are extensively used in the Oriental diet and have been used
to treat various ailments, especially those associated with bacterial infections (34).
The antibacterial effect of garlic has been attributed to allicin, S-2-propenyl 2-
propenethiosulfinate. Garlic extract has been found effective against various
strains of influenza virus in mice (33). Kubota and Kobayashi (Chapter 19) iso­
lated two sulfur compounds from the fruit of Scorodocarpus borneensis
Becc.("wood garlic") which were found to possess antibacterial and/or antifungal
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.
1. MUSSINAN AND KEELAN Sulfur Compounds in Foods: An Overvie5w
properties. Neither of these compounds had been previously found in the allium
genus.
Various organic sulfides present in Allium have been found to have anticar-
cinogenic activity. For example, allyl sulfide, a constituent of garlic oil, inhibited
colon cancer in mice exposed to 1,2-dimethylhydrazine, and allyl methyl disulfide,
allyl methyl disulfide, allyl disulfide, and allyl sulfide all inhibited benzo[a]pyrene-
induced neoplasma of the forestomach and lung in female mice (35). Lam et al.
(Chapter 22) investigated the ability of 2-n-butyl thiophene, a constituent of roast
beef aroma, to inhibit chemically induced carcinogenesis in three different tumor
systems. This compound was found to be effective in the forestomach, lung, and
colon models.
Conclusion
1 The chemistry of sulfur compounds in foods is very complex and continues to be
0
h0 extensively studied. Both cooked and uncooked foods contain organoleptically im­
c
4. portant sulfur-containing compounds. Conversely, the off-odors of numerous foods
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0 have been attributed to sulfur compounds. In addition to their sensory properties,
4-
9 recent work has been increasingly geared towards other functional properties of
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k- these compounds, especially antioxidant, antimicrobial, and anticarcinogenic ef­
b
1/ fects. These areas will, no doubt, continue to be the subject of research for years to
2
10 come.
0.
1
oi: Literature Cited
pubs.acs.org y 29, 1994 | d 231... 2BMS4oha,ea g1lhae4i.nd1 Jsi..,, Α MF.;. .;H CR.R;u Cvba inCn, rGLite..J mR.;e eDrvt.,' S FLo.ouJo.z dPa ,Se Lcri.f.A. N .& uC FtRrl.Ca 1v C9. 71r5i9t,9. 63R(,2 e1)v,8 .,1 F25o39o.. d Sci. Nutr. 1986,
2 | http://Date: Jul 45.. MMaaggaa.. JJ..ΑA..;; CCRRCC CCrriitt.. RReevv.. FFoooodd SSccii.. NNuuttrr.. 11997756,, 67((32)),, 214417..
y 15, 201blication 6. DTerarawneirsth, iF, .R, E.;d B.;u Ntteurryn,b Rer.gG:. ;V Gerulaagda Hgnani,s D C.aGr.l , I1n9 G75e;r 1u7c7h--1u8n6d. Geschmackstoffe;
Jul Pu 7. TB.uEt.t;e rTye, rRan.Gis.h iI,n R F.,l aEvdosr.; SAcCieSn Pcreo:f eSsseionnsaibl lRee Pferreinncciep lBeso oakn; dA Tmeecrhicnainq Cuehse;m Ai­cree,
cal Society: Washington, DC, 1993; 259-286.
8. Tressl, R.; Silwar, R. J .Agric. Food Chem. 1981, 29, 1078.
9. Demole, E.; Enggist, P.; Ohloff, G. Helv. Chim Acta 1982, 65, 1785.
10. Winter, M.; Furrer, Α.; Willhalm, B.; Thommen, W. Helv. Chim Acta 1976,
59(5), 1613.
11. Buttery, R.G.; Seifert, R.M.; Guadagni, D.G.; Ling, L.C. J. Agric. Food Chem.
1971, 19, 969.
12. Buttery, R.G.; Teranishi, R.; Ling, L.C.; J. Agric. Food Chem. 1987, 35, 540-
544.
13. Sloot, D.; Harkes, P. J. Agric. Food Chem. 1975, 23, 356.
14. Boelens, M.; de Valois, P.J.; Wobben, H.J.; van der Gen, A. J. Agric. Food
Chem. 1971, 19, 984.
In Sulfur Compounds in Foods; Mussinan, C., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1994.