bk-1989-0409.ch036

Chapter 36

Downloaded by UNIV OF SYDNEY on June 22, 2017 | http://pubs.acs.org Publication Date: October 3, 1989 | doi: 10.1021/bk-1989-0409.ch036

Volatile Flavor Components in Thermally Processed Louisiana Red Swamp Crayfish and Blue Crab 1

2

T. C.-Y. Hsieh, W. Vejaphan , S. S. Williams , and J . E . Matiella Department of Food Science, Louisiana Agricultural Experiment Station, Louisiana State University Agricultural Center, Baton Rouge, LA 70803 and College of Agriculture and Louisiana Sea Grant College Program, Louisiana State University, Baton Rouge, LA 70803-4200 Louisiana crayfish (Procambarus clarkii) and blue crab (Callinectes sapidus) were analyzed for volatile flavor components. Dynamic headspace sampling, capillary column gas chromatography, mass spectrometry and chromatographycoupled aroma perception were used for characterization. Over 100 volatile components were identified in boiled crayfish t a i l meat, boild crayfish hepatopancreas and/or pasteurized crabmeat. Crayfish and crabs are two important crustacean seafoods i n Louisiana, one o f the most important seafood-producing states. Crayfish are about the s i z e o f a shrimp and look l i k e small lobsters. Crayfish, also known as "crawfish" i n Louisiana, have been regarded as one o f the most important elements i n Cajun cuisine, which i s famous f o r i t s unique f l a v o r s . Louisiana's c r a y f i s h industry comprises the largest commercial crustacean aquaculture industry i n the United States with an annual harvest exceeding 45 m i l l i o n kg and i s increasing (1). The red swamp c r a y f i s h i s the major commercial species. While the t a i l meat has been the major edible portion o f c r a y f i s h , i t s hepatopancreas, a l s o known as crawfish " f a t " i n Louisiana, i s t r a d i t i o n a l l y considered a r i c h source o f natural c r a y f i s h f l a v o r s . K i n l i n e t a l . (2) used steam d i s t i l l a t i o n as a method o f i s o l a t i o n and analyzed the v o l a t i l e components o f hepatopancreas from a b o i l e d c r a y f i s h sample a f t e r the sample had been stored frozen f o r 3-4 months. Information on the f l a v o r components i n f r e s h l y b o i l e d c r a y f i s h i s needed f o r c r a y f i s h product q u a l i t y improvement. Current address: Lever Brothers Thailand, Inc., Bangkok, Thailand Current address: T. J. Lipton, Inc., Englewood Cliffs, NJ 07632

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0097-6156/89/0409-0386$06.00/0 c 1989 American Chemical Society Parliment et al.; Thermal Generation of Aromas ACS Symposium Series; American Chemical Society: Washington, DC, 1989.


36.

HSIEHETAL.

Flavor Components of Swamp Crayfish and Blue Crab

Besides the A t l a n t i c coast, Louisiana and the Gulf coast states are a l s o famous f o r t h e i r abundant supply o f blue crabs. The meat from cooked blue crabs, with i t s d e l i g h t f u l aroma and taste, has long been appreciated by people worldwide. The highly perishable character o f t h i s delicacy l i m i t e d i t s market to coastal regions. Since the development of pasteurization processes f o r crabmeat, s h e l f l i f e under r e f r i g e r a t i o n was extended from 7-10 days to about 9 months, enabling market expansion t o d i s t a n t regions. The presence o f c e r t a i n objectionable flavors i n pasteurized crabmeat has been a p e r i o d i c complaint. Unfortunately, very l i t t l e information i s a v a i l a b l e on the (composition o f v o l a t i l e f l a v o r s o f t h i s product. This paper discusses i n i t i a l r e s u l t s obtained from analysis o f the v o l a t i l e components o f the t a i l meat and the hepatopancreas o f b o i l e d c r a y f i s h and the v o l a t i l e components from pasteurized crabmeat samples using a procedure o f combined dynamic headspace sampling, c a p i l l a r y column gas chromatography and mass spectrometry. MATERIALS & METHODS Materials L i v e red swamp c r a y f i s h (Procambarus c l a r k i i ) and pasteurized blue crab (Callinectes sapidus) meat samples were purchased from l o c a l seafood r e t a i l e r s . Sample Preparation L i v e c r a y f i s h were processed and the t a i l meat prepared as described by Vejaphan e t a l . (3). The hepatopancreas samples from b o i l e d c r a y f i s h were b r i e f l y ground i n a mortar and p e s t l e and were analyzed immediately. The pasteurized crabmeat samples were r e f r i g e r a t e d i n the o r i g i n a l sealed cans for 290 days and were analyzed immediately upon opening. Dynamic Headspace Sampling/Gas spectrometry

Chromatography/Mass

Procedures used have been described elsewhere (3). RESULTS & DISCUSSION F i f t y - e i g h t v o l a t i l e compounds were i d e n t i f i e d i n the dynamic headspace o f the t a i l meat from b o i l e d c r a y f i s h . Forty-nine v o l a t i l e compounds were i d e n t i f i e d i n the dynamic headspace o f b o i l e d c r a y f i s h hepatopancreatic t i s s u e , while f o r t y - f i v e v o l a t i l e components were i d e n t i f i e d i n the dynamic headspace of pasteurized crabmeat. These compounds are l i s t e d i n Table I with the exception o f n-alkanes.

Parliment et al.; Thermal Generation of Aromas ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

387

388

THERMAL GENERATION OF AROMAS TABLE I. V O L A T I L E COMPONENTS I D E N T I F I E D I N T H E D Y N A M I C H E A D S P A C E O F T A I L MEAT (T) A N D H E P A T O P A N C R E A S (H) FROM B O I L E D C R A Y F I S H A N D FROM P A S T E U R I Z E D CRABMEAT (C)

RETENTION COMPOUND

AREA %

INDEX

0

Η

Τ


3-METHYLHUTANAL 2-PROPANOL 2-ETHYLFURAN PENTANAL 2-PENTANONE 2,3-BUTANEDIONE ALPHA-PINENE TOLUENE 3-HEXANONE 2,3-PENTANEDIONE DIMETHYL D I S U L F I D E 2-HEXANONE HEXANAL 2-INETHYLTHIOPHENE 2-METHYL-2-BUTENAL P-XYLENE ETHYLBENZENE T-2-PENTENAL M-XYLENE 1-BUTANOL O-XYLENE 2-HEPTANONE PYRIDINE HEPTANAL LIMONENE PROPYLBENZENE 3-METHYL-L-BUTANOL 3-HEXANOIA 4-ETHYLTOLUENE T-2-HEXENAL 3-ETHYLTOLUENE 2-PENTYLFURAN 2-HEXANOL 1,3,5-TRIMETHYLBENZENE A

A

THIAZOLE L-PENTANOL

A

STYRENE ETHYLTOLUENE METHY LPYRAZ I N E P-CYMENE 1,2,4-TRIMETHYLBENZENE C4-ALKYLBENZENE C4-ALKYLBENZENE

910 926 945 975 980 982 1017 1040 1052 1070 1079 1088 1090 1100 1103 1132 1132 1138 1144 1156 1188 1190 1189 1193 1197 1214 1218 1220 1227 1228 1230 1235 1245 1251 1258 1266 1267 1269 1273 1275 1288 1288 1291

C 6.0 2.2 0.4 23.9 0.3

0.2

2.3 0.3 5.6 1.4 0.1 0.1

0.1

o.I

D

α

ο.ι 0.6. o.I

0.7

3.0 0.5 5.9 1.1

D

0.1 0.4 1.6 1.5 1.0

0.1 0.1 0.2

1.1 0.7 1.8

0.1 0.3 0.4 0.2 0.1 0.1

D

0.4

1.0

0.8 0.2 1.4 0.3

0.4

0.1

0.4 0.4 0.2 0.5 0.6

0.3

o.I

0.2

A

0.4

0.1

0.6 0.7 0.3 0.4

0.1 0.4 0.1

0.7 A

0.2 0.1 0.1 0.4

0.1 0.7 1.1 5.4

Continued on next page


36. HSIEH ET AL*

Flavor Components of Swamp Crayfish and Blue Crab Table I. Continued AREA %

RETENTION COMPOUND

INDEX

0

Τ 2-OCTANONE OCTANAL CYCLOHEXANONE 1,4-DIETHYLBENZENE CYCLOHEXANONE A C4-ALKYLBENZENE A C4-ALKYLBENZENE


A

A

A

2-PENTEN-L-OL 2,5-DIMETHYLPYRAZINE 2,6-DIMETHYLPYRAZINE T-2-HEPTENAL A C4-ALKYIBENZENE A

2 - E THY LPYRAZ I N E 1,2,3-TRIMETHYLBENZENE A C4-ALKYLBENZENE A

1-HEXANOL 3-NONANONE A C4-ALKYLHENZENE L-HEXANOL

1293 1297 1296 1305 1307 1308 1310 1324 1325 1331 1334

C

0.1 0.7

0.1 0.1

d α

0.1 0.1 0.1 0.1

0.1 0.1

0.1 0.4 0.1

0.2

1347 1359

0.2

1363

D

o.i ο.ι

1334 1339 1344

1362 A

0.1 0.3

Η

0.1 0.6 0.2

o.i

d

0.1 0.1

1370

A

CYCLOPROPYLBENZENE

A

A C4-ALKYLBENZENE DIMETHYL TRI S U L F I D E S A

1377 1378 1389

0.1 0.1 0.1

3-ETHYL-2-METHYL1390 1396 1401 1407 1410 1433 1435

PYRAZINE 2-NONANONE NONANAL TRIMETHYLPYRAZ I N E 2-BUTOXYETHANOL A C4-ALKYLBENZENE A C4-ALKYLBENZENE 5-NONEN-2-ONEA T-2-OCTENAL A C4-ALKYLBENZENE

1437 1438 A

ETHYL-DIMETHYLPYRAZINE 1,3-DICHLOROBENZENE 1,4-DICHLOROBENZENE

0.5 0.2

0.2 2.3 0.4

0.2 0.4 0.5 0.3 1.0

1446

AN

OCTENOL

A

L-OCTEN-3-OL 1,4-DICHLOROBENZENE 1-HEPTANOL 3-METHYLTHIOPROPANAL 2,4-HEPTADIENAL /*> A

FURFURAL A C4-ALKYLBENZENE 1,2-DICHLOROBENZENE A

DECANAL

D

0.1

1448 1453 1454 1456 1456 1456 1463 1469

0.1

o.:

0.8 0.3

o.:

1.7 0.1

0. 0.2 0.1 0.9

1475 1481 1495 1497 1498

D

D

0. 0.3 0.2 0. Continued on next page


389

390

THERMAL GENERATION

OF AROMAS

Table I. Continued

CCNPOUND

RETENTION INDEX

C

AREA % Τ

2-DECANONE

1500

T,T-2,4-HEPTADIENAL

1503

N-DECANAL

0.6

LH-PYRROLE

1506 1526

BENZALDEHYDE T-2-NONENAL

1535 1544

0.7

0.5

0.1

0.3

1-OCTANOL

1565

0.2

1571

0.1

3-UNDECANONE

A

0.2 0.9 0.3

2 , 6 - N O N A D I E N A L /B

1594

2-UNDECANONE ACETOPHENONE

0.4 0.2

1-NONANOL NAPHTHALENE

1603 1660 1665 1748

1-DECANOL

1765

0.1

T,T-2,4-DECADIENAL 2-INETHYLNAPHTHALENE

1821

A


Η

0.2

0.2 0.3 0.8

1-UNDECANOL

1863 1876

0.2 0.1

1-METHYLNAPHTHALENE PHENOL

1898 2014

0.1 0.1

A

0.3

: TENTATIVELY I D E N T I F I E D B Y MATCHING THE SAMPLE SPECTRUM WITH LITERATURE REFERENCE SPECTRA WITHOUT CONFIRMATION O F THE R E T E N T I O N I N D E X WITH THAT O F AN AUTHENTIC STANDARD.

K

: CONFIGURATION DETERMINED.

°

: N - A L K A N E S NOT I N C L U D E D . : AREA% S M A L L E R T H A N T H E N U M B E R

D

0.8

OF GEOMETRIC ISOMERS

NOT

INDICATED.



36.

HSIEHETAL.


Three alkylpyrazines, including methylpyrazine, 2,5-dimethylpyrazine and 2,6-dimethylpyrazine, were i d e n t i f i e d as nutty components i n b o i l e d c r a y f i s h t a i l meat. Six a l k y l pyrazines (methylpyrazine, 2,6-dimethylpyrazine, ethylpyrazine, 3-ethyl-2-methylpyrazine, trimethylpyrazine and an ethyl-dimethylpyrazine) were i d e n t i f i e d i n the headspace o f c r a y f i s h hepatopancreas. Pyrazines are generally considered as key f l a v o r components i n many heat processed foods ybecause they contribute nutty, roasted or toasted aromas. Since the formation o f alkylpyrazines has been found to increase when food samples were heated at higher temperatures (4-5), cooking c r a y f i s h at higher temperatures such as f r y i n g may enhance the formation o f these and other nutty f l a v o r s . Interestingly, no pyrazines were found i n the pasteurized crabmeat. lH-pyrrole was i d e n t i f i e d i n the b o i l e d t a i l meat. Although i t d i d not give a strong nutty aroma comparable to those o f alkylpyrazines, lH-pyrrole could s t i l l be a desirable f l a v o r component o f b o i l e d c r a y f i s h t a i l meat due t o i t s s l i g h t l y burnt and sweet character. Dimethyl d i s u l f i d e and dimethyl t r i s u l f i d e were i d e n t i f i e d i n c r a y f i s h t a i l meat with the former also i d e n t i f i e d i n the b o i l e d c r a y f i s h hepatopancreas and the pasteurized crabmeat. These two s t r a i g h t chain sulfur-œntaining compounds e x h i b i t a cooked cabbage and spoilage odor. Although not present as major components i n c r a y f i s h , these compounds generally are considered undesirable. Dimethyl d i s u l f i d e and dimethyl t r i s u l f i d e have been found previously i n thermally processed seafoods and meat products (6-11). A heterocyclic sulfur-containing compound, 2-methylthiophene, was i d e n t i f i e d i n b o i l e d c r a y f i s h t a i l meat and pasteurized crabmeat. Thiazole and 3-methylthiopropanal were i d e n t i f i e d i n the c r a y f i s h hepatopancreas. Heterocyclic sulfur-œntaining compounds play important r o l e s i n generating meaty aromas i n a v a r i e t y o f meat products and are considered important v o l a t i l e aroma components o f marine crustaceans (1214). The 2-methylthiophene could be an important f l a v o r component i n b o i l e d c r a y f i s h t a i l meat. Both t h i a z o l e and 3methylthiopropanal were important contributors to the desirable meaty aroma associated with c r a y f i s h hepatopancreas. The 3-methyl-thiopropanal, i d e n t i f i e d i n b o i l e d c r a y f i s h hepatopancreas, i s derived from Strecker degradation o f methionine (15), and has been considered t o be an important component i n basic meat f l a v o r (16). Pyridine was detected i n the headspace o f the hepatopancreas from f r e s h l y b o i l e d c r a y f i s h . Pyridine and 2-ethylpyridine have been previously reported as components i n the atmospheric d i s t i l l a t e from a sample o f c r a y f i s h hepatopancreas frozen f o r three months (2). As shown i n Table I, many v o l a t i l e f l a v o r components were i d e n t i f i e d i n the samples analyzed. L i p i d composition generally a f f e c t s storage s t a b i l i t y o f various foods. Cmega-3 polyunsaturated f a t t y acids (PUFA) have been i d e n t i f i e d i n the edible portions o f pond-raised and w i l d c r a y f i s h . Crayfish were reported to have higher l e v e l s o f omega-3 PUFA than


391


392

THERMAL GENERATION OF AROMAS e i t h e r brown shrimp or fresh water prawns (17). The high s u s c e p t i b i l i t y to q u a l i t y deterioration and the formation o f l i p i d degradation products i n c r a y f i s h are probably d i r e c t l y r e l a t e d to i t s high omega-3 PUFA concentrations. Eight v o l a t i l e aldehydes containing 5 to 10 carbons were i d e n t i f i e d i n the c r a y f i s h t a i l meat. F i f t e e n aldehydes were detected i n the dynamic headspace o f c r a y f i s h hepatopancreat i c tissue and included 4 saturated aldehydes, 6 alkenals, 4 dienals and 1 aromatic aldehyde. Five saturated aldehydes were i d e n t i f i e d i n pasteurized crabmeat. A l l o f these compounds have been previously i d e n t i f i e d i n the steam d i s t i l l a t e o f the c r a y f i s h hepatopancreatic t i s s u e ; however, only pentanal and hexanal have been detected i n the headspace f r a c t i o n (2). In our study, the saturated and mono-unsaturated aldehydes gave greasy green p l a n t - l i k e odors and probably were not desirable c r a y f i s h f l a v o r components. The compound 3-methylbutanal was i d e n t i f i e d i n the c r a y f i s h t a i l meat and the pasteurized crabmeat, g i v i n g a green p l a n t - l i k e aroma. This compound was reported as one o f the major c o n s t i tuents i n sheep l i v e r v o l a t i l e s (18). Benzaldehyde gave a pleasant almond nutty and f r u i t y aroma and was i d e n t i f i e d i n pasteurized crabmeat and both o f the c r a y f i s h samples. F u r f u r a l , mainly a carbohydrate degradation product, also was i d e n t i f i e d i n the pasteurized crabmeat sample with an i n t e r e s t i n g s l i g h t l y sweet and cooked f l a v o r . This compound might be an important component consistent with the o v e r a l l desirable aroma o f pasteurized crabmeat. The alkadienals could be formed from the autoxidation o f PUFA and may contribute desirable aromas to f r e s h l y prepared foods (19). Further degradation o f alkadienals often increased undesirable f l a v o r s . Josephson and Lindsay demonstrated that 2,4-decadienal could produce 2-octenal and ethanal (20); and 2,6-nonadienal could produce 4-heptenal and ethanal (21) v i a r e t r o - a l d o l condensation mechanisms. Hsieh et a l . (22) reported that isomers o f various alkadienals and a l k a t r i e n a l s gave green, greasy and oxidized f i s h o i l odors i n crude menhaden f i s h o i l . Ketones were found t o be the major v o l a t i l e components i n b o i l e d c r a y f i s h t a i l meats. A t o t a l o f seven saturated ketones (C6 - C l l ) , one unsaturated ketone, one c y c l i c ketone, one aromatic ketone and two alkanediones were i d e n t i f i e d i n the b o i l e d c r a y f i s h t a i l meat. The two alkanediones, 2,3butanedione and 2,3-pentanedione, gave an intense buttery and desirable aroma. Acetophenone imparted sweet rose f l o r a l odor. Four methyl ketones (C7 - C l l ) and 2,3-pentanedione were i d e n t i f i e d i n b o i l e d c r a y f i s h hepatopancreas. Four methyl ketones (C5 - C8) were i d e n t i f i e d i n pasteurized crabmeat. These methyl ketones were usually associated with green, f r u i t y aromas and gave more f l o r a l aromas as chain length increased. Several ketones (C4 - C8) a l s o have been reported as v o l a t i l e flavors o f shrimp (13). The diketones might be important aroma components f o r c r a y f i s h t a i l meat and hepatopancreas products i n providing desirable balance o f the meaty and buttery notes.



36.

HSIEH ET AL.


A series o f alcohols (C4 - C l l ) were i d e n t i f i e d i n the t a i l meat. Odor threshold concentrations were generally higher f o r alcohols than the aldehyde counterparts. Except for 1-pentanol, the remainder o f alcohol peaks were very small and might not be s i g n i f i c a n t i n o v e r a l l aroma o f b o i l e d c r a y f i s h t a i l meat. Josephson e t a l . (23-25) found l-octen-3o l , an enzymatic reaction product derived from l i p i d s , to be one o f the v o l a t i l e components widely d i s t r i b u t e d i n fresh and saltwater f i s h . The compound 2-butoxyethanol i d e n t i f i e d i n c r a y f i s h t a i l meat (3) has been reported i n beef products (2627). GC aroma perception o f standard 2-butoxyethanol gave a spicy and woody note, hence t h i s compound could be an important f l a v o r component o f the b o i l e d c r a y f i s h t a i l meat. Ethyl furan was i d e n t i f i e d i n pasteurized crabmeat. 2Pentylfuran was a l s o i d e n t i f i e d i n a l l three samples and contributed negatively to the f l a v o r q u a l i t y o f both c r a y f i s h and blue crab. Limonene was i d e n t i f i e d i n a l l three samples and p o s s i b l y entered these crustaceans v i a food ingestion. Limonene has been found as a v o l a t i l e component i n f i s h (24), k r i l l (28) and shrimp (13). Eleven, t h i r t e e n and twenty alkylhenzenes were i d e n t i f i e d among the v o l a t i l e s i n the b o i l e d c r a y f i s h t a i l meat, hepatopancreas and the pasteurized crabmeat, r e s p e c t i v e l y . The alkylbenzenes and the naphthalenes might have come from environmental pollutants. Lee e t a l . (30) reported r a p i d uptake o f naphthalene i n marine f i s h . Several chlorobenzenes i d e n t i f i e d i n the c r a y f i s h and crabmeat samples p o s s i b l y were degradation products o f various p e s t i c i d e s . Neff e t a l . (29) reported that aromatic hydrocarbons accumulated i n f i s h to a greater extent and were retained longer than the alkanes. Phenol was a l s o i d e n t i f i e d i n a l l three samples. The medicinal odor o f phenol contributed negatively to these products. Kubota et a l . (28) i d e n t i f i e d xylenes and phenol as v o l a t i l e components that contributed undesirable odors to cooked k r i l l . Besides those discussed above, many areas i n the GC aranagrams o f the v o l a t i l e s from the three samples contained i n t e r e s t i n g aroma c h a r a c t e r i s t i c s , including strong nutty, musty nutty, nutty meaty, good meaty, salty-meaty, mushrooml i k e and cooked egg-yolk l i k e aromas. A substantial amount o f information on v o l a t i l e s can be obtained with l e s s than 30 g o f each o f these samples i n a d i r e c t DHS/GC/MS a n a l y s i s . DHS operation sweeps v o l a t i l e f l a v o r s from the surface o f food samples i n a s i m i l a r way as we s n i f f f o r the v o l a t i l e flavors of a food. DHS does not require high sampling temperature or solvent f o r extraction and may be considered as a low-artifact aroma sampling technique. The concentrating e f f e c t o f DHS provides better s e n s i t i v i t y than s t a t i c headspace sampling. Techniques such as GC-coupled aroma perception and GC/MS i d e n t i f i c a t i o n can be used to complement other approaches i n improvement o f f l a v o r q u a l i t y o f a v a r i e t y o f products.


393

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THERMAL GENERATION OF AROMAS

ACKNOWLEDGMEMS

Louisiana A g r i c u l t u r a l Experiment Station manuscript No.8821-2601. This study was supported, i n part, by grants from Louisiana Sea Grant College Program.


LITERATURE CITED

1. Meyers, S.P. Infofish Marketing Digest. 1987, May/June. ρ 31. 2. Kinlin, T.; Walradt, J . P.; Denton, W. In Fresh Water Crayfish: International Symposium on Freshwater Crayfish, Avault, J. W., Jr., Ed.; Louisiana State University, Div. Continuing Education: Baton Rouge, LA. 1974; pp 175-184. 3. Vejaphan, W.; Hsieh, T. C.-Y.; Williams, S. S. J . Food Sci. 1988, 53, 1666. 4. Koehler, P. E.; Odell, G. V. J . Agric. Food Chem. 1970, 18, 895. 5. Shibamoto, T.; Bernhard, R. A. J. Agric. Food Chem. 1976, 24, 847. 6. Sipos, J . C.; Ackman, R. G. J . Fish Res. Bd. Canada. 1964, 21, 423. 7. Ronald, A. P.; Thomson, W. A. B. J . Fish. Res. Bd. Canada. 1964, 21, 1481. 8. Huges, R. B. J . Sci. Food Agric. 1964, 15, 290. 9. Wilson, R. Α.; Mussinan, C. J.; Katz, I.; Sanderson, A. J. Agric. Food Chem. 1973, 21, 873. 10. Whitfield, F. B.; Freeman, D. J.; Last, J . H.; Bannister, P. A. Chem. Ind. 1981, March, ρ 158. 11. Whitfield, F. B.; Freeman, D. J.; Bannister, P. A. Chem. Ind. 1981, October, ρ 692. 12. Kubota, K.; Kobayashi, Α.; Yamanishi, T. Agric. Biol. Chem. 1980, 44, 2677. 13. Kubota, K.; Shijimaya, H.; Kobayashi, A. Agric. Biol. Chem. 1986, 50, 2867. 14. Choi, S. H.; Kobayashi, Α.; Yamanishi, T. Agric. Biol. Chem. 1983, 47, 337. 15. Wainwright, T.; McMahon, J . F; McDowell, J . J . Sci. Food. Agric. 1972, 23, 911. 16. Shankaranarayana, M.L.; Raghavan, B.; Abraham, K.O; Natarajan, C.P. CRC Crit. Rev. Food Tech. 1974, 4, 395. 17. Chanmugam, P.; Boudreau, M; Hwang, D. H. J . Food Sci. 1986, 51, 1556. 18. Lorenz, G.; Stern, D.J.; Flath, R.A.; Haddon, W.F.; Tillin, S.; Teranishi, R. J . Agric. Food Chem. 1983, 31, 1052. 19. Harkes, P. D.; Begemann, W. J. J. Amer. Oil Chem. Soc. 1974, 51, 356. 20. Josephson, D. B.; Lindsay, R. C. J . Food Sci. 1987, 52, 1186. 21. Josephson, D. B.; Lindsay, R. C. J . Amer. Oil Chem. Soc. 1987, 64, 132. 22. Hsieh, T. C.-Y.; Williams, S.S.; Vejaphan, W.; Meyers, S.P. J . Amer. Oil Chem. Soc. 1989, 66, 114.



36. HSIEH ET AL.

Flavor Components ofSwamp Crayfish and Blue Crab

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