Volatile Components of an Unflavored Textured Soy Protein
JENNIFER M. AMES and GLESNI MACLEOD
ABSTRACT
Aroma volatiles of textured soy protein (TSP) were extracted and
concentrated to a valid isolate using established techniques. By
GC-MS mainly, 146 positive identifications and 26 partial charac-
terizations were made. The majority have not been published pre-
viously as volatiles of TSP or relevant raw materials (raw soybeans,
flakes, flours, concentrates, isolates). Some are probably natural
soybean metabolites - p-damascenone and bovolide being reported
here for the first time in soy. Many result from lipid oxidation/
degradation and from heating sugars and/or amino acids. How-
ever, carotenoid degradation and aromatic ring fusion are also indi-
cated, and could play a hitherto undetermined role in soy proc-
essing technology.
INTRODUCTION
PREVIOUS PUBLICATIONS on the volatile components
of unflavored textured soy protein (TSP), or any relevant
TSP raw materials, have included analysis of (a) the raw
bean (Fujimaki et al., 1965; Arai et al., 1966a; Arai et al.,
1967; Wang, 1972; Greuell, 1974; Honig and Rackis, 1975;
Honig et al., 1979; Moll et al., 1979; Doi et al., 1980; Kato
et al., 1981; Batin&Haberle et al., 1981); (b) soy flakes or
flours (Teeter et al., 1955; Fujimaki et al., 1965; Arai et al.,
1966b; Sessa et al., 1969; Maga and Lorenz, 1974; Maga,
1977; Honig et al., 1979; Hsieh et al., 1982; Melton et al.,
1981; How and Morr, 1982); (c) soy concentrate (Honig
et al., 1979); (d) soy isolate (Qvist and von Sydow, 1974;
Honig et al., 1979; Jackson, 198 1; How and Morr, 1982);
and (e) TSP (Palkert, 1980). From all these analyses, about
200 volatile components have been identified.
It is noteworthy that only one publication (Palkert,
1980) has reported the analysis of textured (extruded)
soy protein volatiles, and in that study 55 identifications
were made, 20 of which had not been reported previously
in the soy products subjected to less severe heat treatment.
The evolution and use of TSP as a basis for meat anologs
has been one of the most significant food technology de-
velopments of recent years. In an attempt to create authen-
tic meat substitutes, the flavor industry has responded with
a notable growth of improved simulated meat flavors.
However, even if perfect meat flavors existed, the success-
ful flavoring of soy protein is limited by off-flavors inher-
ent in soy (or developed during processing) and the absence
of a good, attractive positive e.g. meat-like flavor (Rackis
et al., 1979; Schutte and van den Ouweland, 1979). It
follows therefore that a bland TSP is a useful pre-requisite,
and a knowledge of the volatile components which derive
from TSP should help achieve this goal. The work described
here was initiated in this context.
MATERIALS & METHODS
Isolation of volatile components
Isolate 1. Commercially produced TSP (15Og), manufactured
Authors Ames and MacLeod are affiliated with the Dept. of food
Science & Nutrition, Queen Elizabeth College, Univ. of London,
Campden Hill Road, London W8 7AH, England.
1552-JOURNAL OF FOOD SCIENCE-Volume 49 (1984)
from defatted soy flour, was mixed with distilled water (700mL)
in a 1OL flask and extracted for 1 hr in a Likens and Nickerson
(1964) apparatus, as modified by MacLeod and Cave (1975), using
triple-distilled 2-methylbutane (20mL) as the solvent. The extract
was concentrated to 2OOpL by a low temperature/high vacuum
distillation procedure (MacLeod and Coppock, 1976) using a re-
duced pressure of approx. 0.02 mm Hg.
Isolate 2. A more concentrated isolate was obtained as above
but using TSP (300 g), distilled water (1500mL) and 2-methyl-
butane (20mL). Three such extracts were combined during concen-
tration to 2OOpL.
Blank isolate. A blank isolate was obtained, as for isolate 2, but
using distilled water only in the 1OL flask during solvent extraction.
Gas chromatography
Isolates were analyzed by gas chromatography (CC) on packed
and capillary columns using, respectively, Pye-Unicam Series 104
(Model 64) and Perkin Elmer Sigma 2B instruments, both equipped
with a heated (250°C) FID. For the fused silica capillary column
(50m x 0.32mm i.d.) coated with 0.5nm film of BP20 bonded
stationary phase (equivalent to PEG 20M), helium carrier gas
(2mL/min) was used in conjunction with a nitrogen make-up
gas (30mL/min) and the temperature program was 6O’C for 3 min,
followed by an increase of 2OC/min to 200°C for the remainder
of the run. The injection point heater was at 25O”C, and typically
l+L were injected using s lit ratios varying from 5: 1 to 2O:l
at an attenuation of 1 x 10 ,I (5 x 10-l’ A fsd). Retention times
and peak areas were recorded by a Hewlett Packard integrator
(Model 3370B); for isolate 1, peak areas were expressed as a per-
centage of the total peak area i.e. relative percentage abundance
(RPA). Packed column analyses were performed using a glass
column (5.5m x 4mm i.d.) packed with 10% PEGZOM coated on
acid-washed loo-120 BSS mesh Diatomite C, with* nitrogen (30-
mL/min) as the carrier gas and a temperature program of 60°C
for 10 mm, followed by an increase of 12”C/min to 175°C for the
remainder of the run. Typically 4 - 10 PL were injected at an atten-
uation of 1 x lo3 (1 x 10h9 A fsd).
Gas chromatography-mass spectrometry
Components were identified as far as possible by gas chromatog-
raphy-mass spectrometry (GC-MS) analysis of isolate 2, using a Per-
kin Elmer Sigma 3 GC interfaced via a single-stageall glassjet sepa-
rator at 250°C to a Kratos MS 25 instrument linked online to a
Kratos DS 50s data processing system and equipped with a com-
puter-controlled multipeak monitoring (MPM) unit. The same GC
conditions as described above were employed but using Grade A
helium (40 mL/min) as the carrier gas for the packed column.
Significant operating parameters of the mass spectrometer during
electron impact ionization work were as follows: ionization voltage
70eV; ionization current 100 PA; source temperature 200°C; accel-
erating voltage 1.3 kV (packed), 4 kV (capillary); resolution 600;
scan speed 3 set/decade (packed), 1 set/decade (capillary), repeti-
tive throughout the run. Identical conditions were employed during
chemical ionization mass spectrometry except for the following:
reagent gas, methane; ionization potential 110eV; emission current
5mA.
Gas chromatography/microwave plasma detection (GC-MPD)
Selective detection of carbon, hydrogen, oxygen, nitrogen and
sulfur in the volatile components separated by GC was achieved by
a microwave plasma detector (MPD), the operation and reliability
of which has been discussed (Brenner, 1978). An MPD (Applied
Chromatography Systems) was coupled to a Pye Unicam Series 104
(Model 84) GC. The GC conditions described above for the packed
column were employed, but using, as carrier gas, Grade A helium
purified by a r&e ias .purifier (British Oxygen Co., RGP MK3).
Significant operating parameters of the MPD were as follows: tube
current lOOmA (oxygen scavenge), 50mA (nitrogen scavenge);
HV attenuators C15, H14, N13, 013, S13, Cl 12; ghost corrections
variable. Analyses were performed in triplicate using both scavenge
gases.
Empirical formulae were calculated by relating elemental GC
peak heights to those of compounds positively identified by GC-MS:
C Ht of C pk in UK Ht of X pk in Std No. of C atoms in Std
-= X X
X HtofXpkinUK HtofCpkinStd No. of X atoms in Std
where X is an element other than carbon (C) which occurs in
the unkonwn (UK), and C/X is the ratio of carbon atoms to X
atoms in the unknown. The internal standards used were toluene,
2-butylfuran, 2-pentylfuran, benzaldehyde and naphthalene.
Odor assessment
Aromas of components separated by GC using 1OrL isolate 2
on the packed column in the Pye Unicam 104 instrument, were
described at an external GC odor port by three experienced asses-
sors. An outlet splitter (1O:l) diverted the major fraction of the
eluate through a heated (200°C) line to the odor port.
RESULTS&DISCUSSION
VALID AROMA ISOLATES of the TSP were prepared
using well-established procedures that have been reported
previously (MacLeod and Coppock, 1976). Aroma isola-
tion conditions were less severe than those used during
processing of soybeans to TSP (Pagington, 1975; Kinsella,
1978), and the heat treatment was fairly representative of
normal cooking conditions. The creation of artifacts during
isolation was therefore unlikely, and this is supported by
the fact that an aroma which was characteristic and highly
representative of the reconstituted and heated (1 hr) TSP
was associated with isolate 1; these aromas were described
by three experienced assessors as cereal-like (not roasted),
slightly green/beany and slightly musty/moldy. The quali-
tative GC peak patterns of the two isolates were identical,
but isolate 2 was more concentrated than isolate 1.
Isolates were analyzed by GC, GC-MPD and GC-MS
(using both electron impact and chemical ionization mass
spectrometry) and the results are presented in Table 1. Use
of triple-distilled solvent gave a blank isolate chromatogram
showing only the 2-methylbutane peak, closely followed by
two small impurity peaks, and these are not included in
Table 1. The retention data given in the table were ob-
tained using the 50m fused silica column coated with BP20.
Kova’ts retention indices (Jennings and Shibamoto, 1980)
of many components (on PEG 20M) are also included,
and they confirm the general elution sequence. Select
element detection and the calculation of empirical formulae
by GC-MPD analysis also confirmed mass spectral interpre-
tations in several instances. The qualitative data in Table
1 were obtained using packed and capillary columns; some
components were best identified by GC-MS using one type
of column. In all instances where positive identities are
given, the mass spectra obtained on GC-MS agreed with
those in the literature (e.g. Lardelli et al., 1966; Demole
et al., 1970; Eight Peak Index of Mass Spectra, 1974;
Jennings and Shibamoto, 1980; Kennet et al., 1977-l 982).
The polar PEG 20M (and equivalent) columns were selected
for analysis because they gave far superior resolution of the
total isolate than similar nonpolar OVlOl (and equivalent)
columns. However, the minimum temperature requirement
of about 60°C for PEG 20M did preclude the identity of
low boiling components such as pentane.
The complex chemical composition of the volatile frac-
tion is immediately obvious from Table 1. A total of 146
aroma components was positively identified together with
a further 26 partial characterizations comprising, in all,
about 85% (w/w) of the volatiles. Most of the unidentified
components were present in extremely small concentra-
tions and gave rise to poor mass spectra, but three sizeable
GC peaks (representing 2.0, 1.5 and 1.5% of the total vola-
tiles) could not be characterized. One hundred three
components reported here have not been reported previ-
ously as volatiles of any relevant TSP raw materials i.e.
raw soybeans, flakes, flours, concentrates or isolates; an
additional 35 compounds were not reported by PaIkert
(1980) in the only previous study on TSP volatiles. Such
newly identified components are clearly labelled in
Table 1.
A wide range of chemical classes is represented in
the TSP aroma; these are mainly aliphatic hydrocarbons,
alcohols, aldehydes, ketones, sulfur compounds, esters,
benzenoids, terpenes, furans, la&ones, thiophens, pyrazines
and thiazoles. Some possible precursors and formation
pathways for several of the components identified are pre-
sented in Table 2, which shows that many can be accounted
for by lipid oxidation/degradation and/or the effect of heat
on sugars and/or amino acids. Thermal degradations, if any,
during chromatography were deemed insignificant, as evi-
denced by the fact that a chromatogram obtained using the
capillary column and lower GC temperature conditions
(final column temperature 15O’C; detector and injector
175’C) could be correlated with the original chromato-
gram. These temperatures approximate those used during
extrusion of soy protein when considerably higher pres-
sures are also used.
It is well established that autoxidation and/or the action
of lipoxygenase is of paramount importance in soy flour
(Heinze et al., 1978). In addition, during certain stages of
soybean processing and especially during soaking, lipid
degradation may be catalyzed by other enzymes including
lipases, phospholipases, “hydroperoxidases” and isomerases
(Gardner, 1980). Furthermore thermally induced oxida-
tion, as well as nonoxidative thermal degradation of lipids,
can occur in any product - such as TSP - subjected to
heat. Some residual oil remains even in defatted products
(Heinze et al., 1978) and the polyunsaturated fatty acid
content of soy lipids is 63% (Masson, 198 1). Linoleic and
linolenic acids are believed to be the most common oxida-
tion substrates (Smouse and Chang, 1967; Litman and
Numrych, 1978; Kinsella and Damodaran, 1980) and their
oxidation is facilitated by maceration of the bean and/or
the presence of moisture (Kinsella and Damodaran, 1980).
The predominant oxidation products are alkanals, alk-2-
enals, alka-2,4-dienals, the corresponding alcohols and both
saturated and unsaturated ketones (Hoffman, 1962; Forss,
1972; Tress1 et al., 1972; Frankel, 1983), and these are also
the major volatile components of reverted soybean oil
(Smouse and Change, 1967; Selke et al., 1970). Gremli
(1974) concluded that aldehydes represent the major
fraction of soy protein volatiles, and in agreement with this,
aliphatic aldehydes were present in the highest concentra-
tion (“32% of the total volatiles) in our TSP aroma -
largely due to hexanal at 15.5% of the volatiles; other major
aldehydes present were pentanal, hept-2-enal, act-2-enal
and deca-2,4-dienal (see Table 1). The latter compound is
the major volatile carbonyl component produced on de-
gradation of linoleic acid at elevated temperatures (Swo-
boda and Lea, 1965; Kimoto and Gaddis, 1969) and has
been associated with the flavor of fried foods (Forss, 1972).
It has been identified in a variety of soy protein products,
and its formation is likely to be enhanced during toasting
and extrusion. Two of its isomers, present at a combined
level of 5.0% in our TSP aroma, have been associated pre-
viously with an undesirable fatty, oily note in soy (Heinze
et al., 1978). Aldehydes generally are believed to affect the
flavor of soy products to the greatest extent, due not only
Volume 49 (1984)-JOURNAL OF FOOD SCIENCE-1553
 TEXTURED SOY PROTEIN VOLATILES.. .
Table I- Volatile components of an unflavored textured SOY Protein
NW@ KG-J& N.3wd.b KWitS
identifi- ‘tl index identifi- index
Component cation (mini (lit.1 WA Odor quality Component cation (lit.) RPA Odor quality
3.methvbentane 4.41 0.02 35.35 0.20
a dimethylethylpyrazme* “U””
2.methylpentane 4.55 0.25 Z*cetylfuran a 1491 0.01
35.91
methylcyclopentened 4.62 0.50
Z-oentvlthiophen 36.00 1462 0.01
acetaldeh& 4.82 690 1 .oo a C,-p&&e 36.34 0.02
cyclohexaned 5.47 765 0.10
Pfuraldehvde 36.43 1449 0.25 roasted cereal,
cmmsd 600 0.10 Oil”. fatty. sweaty roasted lamb fat.
methylpropanald 800 0.20 caramel. burnt rancid
cerbonyl sulfide 5.52 0.02 burnt
hspta-2.4dienald b 36.51 0.05 “npleamt. green,
*CatOne 5.62 910 0.75
sap-like
butanalC 6.56 0.01
2.6dimethylstyrene a 36.68 0.02
I-methylfurand 866
indene * 37.01 0.02
2.methyloctaned 6.73 0.10 green
1.3dimethqWethylbenzene a 37.06 0.10
butanone 7.12 908 0.05
dean-Z-one 37.39 1460 0.10
Zmethqlbutanal 7.38 0.20
hepte-2.4dienald b 37.60 1 .oo green, c”c”mber
3.methylbutenala 7.38 937 0.60 fresh green,
decanal b 37.75 1485 0.01 slightly green,
them. solvent
7.70 fragrant
2.2.4.trimethvlheptane 0.10
7.78 0.01 a dimethylindan * 38.09 0.01
non9en-Z-ane a 39.62 0.25
a.oa 951 0.60 buttery, caramel
benzaldehyde 39.43 1502 6.00 almonds, nutty
butanedione Idiacetyl) a.78 0.10 butterv
1,2,3,4-tetrahvdronaphthalene a 39.93 0.20
butenoned (methyl vinyl ketone) ii: green.&e,
p*~tdd 8.66 1002 -)
1.75 grassy dec4enal
non-Zrnal
a
*
39.97
40.30
15231~)
1540
0.05
0.75
damed - caramel, buttery
octan-l*l b 40.72 1519 0.25 floral. hyacinth,
Z.methylbuten-Zal 9.38 1.25
trichloromethane 9.76 0.05 oily, fatty
2.methylpyrrole * 41.05 0.01
thiophen 10.12 3.25 fruity. stored
2.methvl.1.2.3.4-tetra- a 41.94 0.01
epples
hydronaphthalene
Z-ethyl.5.methylfuran 10.25 1024 0.02
2,4 (or2,5ldimethyl- a 42.25 0.02
2-propylfuran 10.25 1083 0.02
ethyl butenoate 10.52 1025 0.10 isopropylbenzene
rxta 3,5dien-2.one 42.65 1.75
totuened 10.93 0.10 them. solvent
2-propionqlfurand 43.04 1563 0.02 green, nutty
pentans-2.3dione a 11.57 1044 0.25 buttery. caramel
octa 2.4dienald 43.26 0.02
dimethyl disulfide b 12.25 1081 0.10
3methylindawl-one 171 43.45 0.02
psnten-2*,1 b 12.25 1091
hexanal octe-2,4dieneld 43.85 0.05 oily, walnuts
12.65 1064 15.50 green
1.6dimethylindan 45.51 0.10
2methvlthiophenc 13.05 0.01
phenylacetaldehvded 47.41 1646 0.02 floral. fragrant
2-methvlbut-2wal 13.36 0.02
acetophenone 47.69 1627 0.10 slightly meaty
ppinene 13.56 1124 0.05
nona.2,4dienald 48.33 0.01
Z-methylbutyl eceteted 14.26 1110 0.26 ester”, pear-drops
e trimethylindan a 49.33
ethylbenzeneC 14.58 0.20
thiophen-3.cerboxeldehyde * 49.15 0.01
2.butylfuran 14.77 1130 0.50 wet hay
o-hydroxybenzeldehyde 8 49.40 1668 0.10
p-X~lCd 15.12’ 1140 0.06 stale, cold meat fet
(salicylaldehyde)
in-xytenec~d 15.26 1147 0.10 unpleasant, rancid
heptadecane a 49.64 1700 0.02
heptene-2.3dione 15.57 1138 0.25
thiophen.Zcarbpxaldehyde a 50.15 0.20
carJene 15.65 1144 0.06
a terpenoid * 50.15 0.05
lllVV2R”R 16.20 1156 0.10
6.methyl-1.2.3.4. 8 50.43 ‘0.02
isopropylbenrenec*d (cumenel 17.05 0.05 them. solvent
tetrehydronaphthalene
heptan-2-oned 17.63 1172 2.25 slightly green,
nona-2,4dienald 50.83 0.25 unpleerant,
““‘W
cereal-like,
17.96 1166 1 .oo gr..";""ttv
wet WOOI
O-%Vleflec 17.96 1191 0.10
terephthaldehyded a 51.25 0.05
limonene a 18.32 1206 1.75 fruity. fragrant naphthalene 52.95 0.50
hexanl-al 18.99 1192 0.20
undec-Z-enal 53.82 0.06
propylbenzeneC a 19.41 0.05 deca-2,4dienald 54.62 0.50
hex-Z-enel b 19.68 1207 0.05 n.methvIecetophenoneC 55.59 1750 0.05
l-ethyl-3.methylbsn~ene~ a 19.77 0:10 beta-2.hdienaid 57.47 4.50
Z-pentylfuran b 20.13 1229 3.50 2.cdimethvltiophen-3. 57.47 0.20
penmn-~.o~d 20.70 1213 2.75 Yeast-like
thiazole carboxaldehyde
21.08 ‘246 0.02 2-b”t.n~yl-5-m~thylfUran * 57.79 0.05
1746
pecimene 21.08 12501t)
1 -trans.but-2enoyl.2.6.6. 8 58.15 16OV 0.20
1.3.5.trimethylbfin~ene~ 21.20
trimethvlcvclohexa.t.3diene’
rtyrene 21.46 @dama&exmel
ocmn3~ne 21.59 1190 0.01
2-methylnaphthalenec a 59.81 0.05 floral, fragrant
Zmethylbutyl butenoate 21.85 1259 0.10 2-acetyl4.methyC a 61.11 0.01
l-athyl.2.methylbenzeneC 21.85 0.02 cyclopentane-1,3dione
methylpymzine 22.20 1251 0.05 I-mothyl”aphthaleneC * 61.67 0.10 hay
e methyl iso~ro~vlbenzene a 22.29 0.05 a monclterpene * 62.05 0.05
la cvminel 2-phenylethanolc a 62.28 1859 0.01 floral, fragrant
a methyl isopropylbenzene * 22.62 0.10
2,6di+butylq- 62.90 0.10 toasted cereal
la cqmene) hydroxytoluene ISHT)
1.2.4.trimethylben~ene~ * 23.48 0.20
undeca-2.4dienal * 63.49 0.02
octan-z-one 23.76 1275 0.20 fragrant
0.06
Z~ethyl-5.pentanoylfuran (I 63.69
oct*n*1 23.93 1278 0.20 oily, nut oil Zpentenoylthiophen a 63.97 1993 0.02
B diethylbenzene * 24.50 0.05 nutty. green Z.phenylb”t-Z-enal a 64.31 0.02
rep-like
2-athylnaphthalenec a 64.60 0.05
* 24.72 0.10 benrothiarole a 65.20 0.20
a b&,&z&e a 25.26 0.02 lethylnaphtheleneC a 65.51 0.10
2.5dimethylpyrazinec*d 26.23 1306 0.25 e dimethvlnaohthalene a 65.71 0.25
hept-2anald b 26.47 2.0 oily, 6tde. mm
10.meth;l&decane a 66.66 0.01
cid, linseed oil e dimethvlnaphthalene 8 67.32 0.05
* C&enzene a 26.54 0.02 e dimethylnephthalene 67.67
* 0.20
ethylpyrazine b 27.12 0.20 burnt, iron 1 ,Idiisopropyl-3. a 68.05 0.05
scorch ethylbenzene
hexan-l-old 27.30 1316 6.0 green, earthy pantadecen-Zone * 68.50 0.05
cvclohexvl acetate 27.90 1343 0.10 i dimethylnaphthalene 8 69.65 0.02
abimeth~lethylbenrene 28.01 0.02 4hydroxydecanoic acid, * 69.86 2101 0.10
2.butylthiophen 28.09 0.10 lactone Iydecalactcn.el
a dimethylethylbazene 20.44 0.10 en isopropylnephthalene * 70.39 0.10
l.Zdimethyl-3-ethylbeanlene 26.91 0.20
1,4diisopropyl-2.5. a 72.52 0.50
o-methylrtyrene 29.20 0.02
30.60 1420 0.05 fragrent. slightly dimethylbenzenel7l
nonen-zone 0.05
diphenylmethane a 72.97
fruity
an isopropylnaphthalene * 73.47 0.02
nonamP b 30.73 1382 0.50 sweet, fragrant
a trimethylnaphthelene a 73.66
Zbthyl.S-methylpyrazine 30.87 0.50 0.05
B trimethvlnephthalene a 73.66
hex.Z.en-l-old b 30.97 13681tI 2.75 ralad vegetable,
a trimeth~lnaphthelene a 74.66 0.02
rancid, blue
2,3dimethyl4-hydroxynona- a 77.04 2133h 0.05
cheese
trimethylpyrazine 31.82 1387 0.05 2.4dienoic acid, lactonef
octJen.2.one b 31.95 1.50 flat. dull. green Ibovolidel
a trimethylbenzeldehyde * 77.44 0.05
e tetr?methvlbenrene II 32.96 0.01
2.methoxv4-vinvlphenol b 78.35 1.75
act-amaId b 33.38 1427 2.50 dandelion/dock
l.WeO ~p.vinyl&iacoil~
2-benzylideneheptanal a 84.63 2211
cd-1 -en-3.al b 33.70 2.25 oily, fatty. cucum-
tmr, stale nuts (or-pentylcinnamaldehydel
to their low odor threshold values (Kinsella and Damo- Crs terpenoid-related compound, P-damascenone, was
daran, 1980), but also to their ability to bind to soy pro- also present (see Fig. 1). This compound was first identified
tein (Gremli, 1974). Components of Table 2, other than by Demole et al. (1970) in Bulgarian rose oil, and it has
aliphatic aldehydes, which could have derived from lipid since been reported in Burley tobacco (Demole and Ber-
degradation and which were present in relatively large thet, 1971) and in several plant foods e.g. cooked apples
concentrations in the TSP aroma were heptan-2-one, oct- (Nursten and Wolffe, 1972) and tea (Renold et al., 1974).
3-en-2-one, pentan-l-01, hexan-l-01, hex-2-en-l-01, act-1 - It derives in nature from oxidative degradation of the caro-
en-3-01, benzaldehyde and 2-pentylfuran. Several of the
aliphatic hydrocarbons of Table 1 have not been identified
previously in relevant soy raw materials and probably
arise from thermal nonoxidative degradation of lipids Table 2-hssible origins of some of the TSP aroma components
e.g. during extrusion (Nawar, 1969; Litman and Numrych, Lipid oxidation/ Heated sugars and/or
degradation amino acids Other
1978).
Table 2 shows that a significant impact of heat is to pro- octan.@=de cqclohexane”.
decane=‘g butanal” methqlcqclo-
duce certain short chain aliphatic aldehydes, ketones and hsptadecane pentanelkw pentanek’
sulfur compounds, certain benzenoids, furanoids, thiophens pentan-l-ol*bCdfh haxan# tol”erd’
hexan-l-old’” methylpropanalty*a’ m-xylene”
and pyrazines. Thermal degradation of sugars, pyrolysis octan-1 x.Pd*’ 2.methylbutanaltVb’ BHTm’
of amino acids, Strecker degradations and Maillard reac- pentan-2.olf 3~methylbutanal”’ p-vinylguaiacol”’
2,6dimethyl-
tions will certainly occur during extrusion - a process hexan-2-ol aceronetU
hex-2-w-l.ol butanonetux naphthalenel’
involving temperatures of about 15O’C and pressures of oct-len3.ol”bc*’ butanedionetx naphthalener””
about 1000 psi (Pagington, 1975). Thiamin degradation by butanalbcfg oentene-2.3.dio& monoterpenasP’
heat may also contribute to the presence of 2-methylfuran pentanalbcd*f b”te”o”ei P-damascenoneP’o’
hexanalabcdef tol”e”.P=‘d’ 2.methylfuran”
and 2-methylthiophen (van der Linde et al., 1979) while heptanalbcdf e’hylbanzene’=’ bovolideP’
thermal decarboxylation of ferulic acid is the likely expla- octanalabcdef propylbenzenec’ 2-methylthiophen”
nonanalabCdef 0.xv1enet chloroform”
nation for the presence of p-vinylguaiacol (Greuell, 1974). decanatabcde m-xylenetx
Thiophen is present in the TSP aroma at the relatively high 2.methylbut-2.enal p-xy1enetx
concentration of 3.25% of the total volatiles, and previous hex-2-enalcg 1,2,4-trimethylbenzene’
hept-2.enalabce 1.3.5.trimethylb,enzene’
studies reporting the presence of thiophens in soy protein act-2enalabcdfg benzaldehydeXC
products have also involved the application of heat at non-2enaPdfi phenylactaldehydevc’
undec-2enalabcde acetophenonee’
121’C or above (Qvist and von Sydow, 1974; Palkert, dec-4-enalj sytrene=
1980). Similarly, the only soy protein product in which hepta-2,4dienalfgk inden&
dimethyl disulfide has been reported previously was a octa-2.4dienals carbonyl sulfide”
nona-2,4dienalabc dimethql disulfide””
heated soy isolate (Qvist and von Sydow, 1974). Also, deca-2,4dienalsabCe 2-methylfurant
pyrazines have been identified only in heated soy products undeca-2,4dienal P-ethvlfuran’
heptan-2-oned’g’mn P-probylfurant
(Maga, 1977; Doi et al., 1980; Palkert, 1980). octan-20nedfg’mn 2-ethyl-5.methylfuran’
Certain compounds are renowned for their contribution “0”*n-2-0”&*” 2.furaldehyde”“g’
to soy off-flavors. For example, green, beany off-odor has decen-2oneg*” 2-ecerylfurantwxg’“’
pentadecan-2.onegm” thiophan”‘g’
been attributed to several aliphatic alcohols, aldehydes, octan-3onee 2.methylthiophenxf
ketones (including pent-1-en-3-one i.e. ethyl vinyl ketone) butanedionea 2-butylthiophen
and 2-pentylfuran (e.g. Mattick and Hand, 1969; Heinze oentane-2.3dione’ 2-pentylthiophen
heptane-213dione thiophen-2.cerboxaldehydexh’
et al., 1978; van den Ouweland and Schutte, 1978; Rackis act-3-m2-aid thiophen-3-carboxaldehyde
et al., 1979; Kinsella and Damodaran, 1980). Oxidized, non3en-Z-one 2,5dimethqlthiophen-3-
octa-3-,5dien-2-o& carboxaldehyd$
oily, rancid and paint-like odors have been attributed to p-xylwle0 2-methylpyrrole’
the higher alka-2,4-dienals (Rackis et al., 1979). Musty, alkylbenrenesP methylpyrazin&’
moldy quality has been associated with geosmin and aceto- benzaldehqdeafo ethqlpqrazin&
acetophenone*’ 2.5.dimethqlpqrazine9’j’
phenone (Rackis et al., 1979; Kinsella and Damodaran, naphthalane 2,6dimethylpyrazin&
1980) while a cooked off-flavor is reported to develop as a 2.butylfuran” trimethylpqrazinewg’i’
z-pentylfuranbcef’or 2.ethyl-5-methylpyrazine
result of the presence of p-vinylphenol and p-vinylguaiacol 7-decalactone’ thiazoleg’
(van den Ouweland and Schutte, 1978). In the present
t Frankel (1960) ~sesse (1979)
study, specific attempts were made to detect these com- Fran*el et a,. (1981) mNaw*r *t al. (1978)
z Frankel (1963) Nawar (19691
pounds, including use of the MPM unit of the GC-MS, but Selke et et. (1977) “Litmanand Numrych (1976)
no evidence of the presence of either ethyl vinyl ketone ; SoIke et al. (1960) 0 For** (1972,
.$mouse,and Chang (1967) PMln et *I. (1977)
(I 1047, reference compound) or p-vinylphenol or geosmin t Chang et et. (1978) 7 Kawada al al. (1967)
/ Tressl St a,. (1977) Chang et el. (1966)
could be obtained. The absence of ethyl vinyl ketone was Selke et al. (1978) ' W~ta"abeandS~to(1971)
j hthgs (1970)
also noted by Palkert (1980) in his study of TSP. It derives
t Thermal dagradatlon Of glucose (Suglsawa. 1966; Keynes at al.. 1956; w*1ter
from lipoxygenase action, and other oxidation products and Fagerson. 1966)
“P~rol~sls of various amino acids (MacLeod and SeyYedaln-Ardeblll, 1961)
were certainly present in our TSP volatiles. Both p-cou- LStrecker degradation (MacLeod and Seyyedeln-Ardeblll. 1961)
maric acid and ferulic acid, the precursors of p-vinylphenol Hsated glucose (or fructose)/glyclne (van den Ouwaland et al., 1976)
XHmted glucose/cYstslne (Scanlen et al., 1975)
and p-vinylguaiacol respectively (Rackis et al., 1979), are YPyrOlySls of vallns (Merritt and Robertson
?,P~rol~sIs of leuclne (Lien end Newer. 197hl
1957)

reportedly extracted from soy flour with polar solvents a. Pyroiysis of methlo&e (Fujlmakl ei al., 1569)
b’ PYrOlysls Of lsoleuclne (Lien and Newer. 1974)
e.g. aqueous ethanol (Rackis et al., 1979; Kinsella, 1978) C’ Pyrolysis of phenylelenine (MacLeOd and Seyyedeln-Ardeblll. 1961)
d: PY~o~Y~~sof tyrosine (Merritt and RObertsOn. 1967)
such that the resultant product does not develop the offen- ;, DeCOmpOnsitlOn Of trYPtOphen (Klnsella and OamOdaran, 1960)
sive cooked flavor; however if this explains the absence of PYrOlYSlS of Cystelne (Kate et al.. 1973a; Merritt and Robertson.
',: l4aat.d cYStei”s Ior cYstl”e,,carbO”Yl CornpoUnd (Kate at (I,., 1973b)
1967)

p-vinylphenol in the TSP volatiles, it would appear that Heated Cystelne/cystineribose (Mulders. 1973)
1’Pyrolysis of serlne or threonlne (Wang end Odell. 1973; Kato et el., 1970)
ferulic acid is the more likely of the two precursors to sur- L,Heeted glucosel/n9S/NHS (Shlbamoto and Russell, 1977)
Possible Impurity In defatting solvent (Honlg et al., 1979)
vive such treatment. I’ ;rhsrmal degradotlon Of carOtsnOlds (Finer. 1949; Drewerr et el.. 1961)
“1 Lipid antioxidant (FranksI. 1960)
Some of the compounds identified here for the first n, Thermal decerboxylatlon of ferullc acid (Greusll, 1974)
time in TSP (or its relevant raw materials) deserve special O, Fused ring formation
P, Naturally-xcurrlng
from Other benzenotds
metabollte
(Vltrthum et al.. 1975)

mention. The monoterpenes (Cio) are probably naturally o, Oxldatlve degrsdatlon Of cerotenolds (Iroe et al.. 1973)
:, Thlamln degrsdatlon (van der Linda et et.. 1979)
occurring metabolites of the bean. However, an interesting Possible CO”tamlne”t derlvlng fro,,, pestlclde 1eslduOs (HO and Coleman.

Volume 49 (1984)-JOURNAL OF FOOD SCIENCE-1555

 TEXTURED SOY PROTEIN VOLATILES.. .

tenoid neoxanthin (Isoe et al., 1973) and, although it is realized (Drawert et al., 1981). Additionally, as evidenced
present in green tobacco, curing ageing increases its concen- by the identification of several naphthalene derivatives,
tration considerably (Enzell, 1981); a similar increased aromatic ring fusion or cyclization may also result under
production may occur TSP during processing and storage. extrusion conditions.
Thermal degradation of carotenoids is known to occur
and, for example, P-carotene forms toluene, m-xylene and REFERENCES
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Doi. Y.. Tsugita. T.. and Kurata, T. 1980. Changes of headspace
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1962; Lardelli et al., 1966); it was so-named because of its mas. In “Flavour ‘81,” Third Weurman Symposium. Munich,
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THIS STUDY SHOWS that the aroma of TSP is due to a dised fats by gas chromatography-mass spectrometry: 7. Volatile
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Fig. l-Chemical structure of p-damascenone and bovolide.

1556-JOURNAL OF FOOD iCIENCE-Volume 49 (19841

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London) for the award of a postgraduate scholarship (to JMA).

Volume 49 (1984kJOURNAL OF FOOD SCIENCE- 1557