THE CHEMISTRY OF C O O D D AND CANNED MEAT FLAVOR*

STEPJ3EN S. CHANG Rutgers, The Sta te University

INTRODUCTIOIJ

The study of meat f lavor has been extensive and numerous. Recently, Herz and Chang made a thorough review of t h i s subject and published t h e i r findings i n the 1970 issue of Volume 18 of Advances i n Food Research. This made it possible f o r t h i s t a l k t o be completely devoted t o the attempt of our laboratory i n thc isolat ion and ident i f icat ion of vo la t i l e f lavor cDmpounds which a re responsible f o r the character is t ic f lavor of boiled beef, and the off-flavor i n canned beef stew.

Experimental Results and Discussion

I n our study, 284 lbs . of beef were obtained f rm the semitendonous muscles of 43 s t ee r s of the same feeding l o t with known h i s t w y , as shown i n s l i d e 1. water. The v o l a t i l e compounds isolated from t h i s boiled beef were considered the f lavor of the f resh sample. Another 44 lbs . D f the composite beef sample were boiled with water, freeze-dried, canned under an atmosphere below 2% of oxygen and stored a t 6 0 0 ~ f o r 18 months. v o l a t i l e cDmpounds isolated from t h i s sample a f t e r rehydration were considered t h e aged boiled beef f lavor . szmple were processed and stored under various conditions.

Fif ty-s ix lbs . of the composite sample were boiled with

The

The other 184 l b s . of the beef

It i s our philosophy t h a t i n order t o ident i fy the complete spectrum of v o l a t i l e f lavor compounds i n a food, par t icu lar ly those compounds which have flavor charac te r i s t ics of t he food i n question, we must f irst i s d a t e a suf f ic ien t amount of the vo la t i l e f lavor compounds and t h a t the isolated v o l a t i l e compounds must have a f lavor reminiscent of the genuine f lavor ol' the or ig ina l food. The apparatus, as shown i n s l i d e 2, w a s spec ia l ly designed and b u i l t t o serve this purpose.

'The boiled beef was made in to a water s lurry, using a meat grinder ard n blaring blender. 70% i n f l a sk B . evacuated t o a vacuum which should be 0.01 rmn H g a t the end of t he cold t r a p s . The apparatus on the l e f t of the pump, C , was under atmospheric pressure. The last three t r aps were cooled with l iquid nitrogen and t h e f irst f ive t raps were cooled with dry i c e . The water slurry of boiled beef was fed in to t h e vaporizer, D, a t a constant, continuous r a t e with the use of a posi t ive displacement ro ta t ing and reciprocating pump.

The water slurry was s t i r r e d and mair;tEined a t The whole apparatus on the r igh t of the pump, C y w a s

The

* Presented a t the 26th Annual Reciprocal Meat Conference o f t h e Americen Meat Science Association, 1973.

77 SLIDE 1

Semitendinosus Mus cle s

of 4 3 Steers *

SAMFLES USED FOR 'THE STUDY OF FLAVOR DETERIORATION OF BOILED G E E F

i )

Tolatile Flavor Compounds

Analyzed

I Freeze Dried

Canned (below 2% oxygen)

for 18 months

and stored under various conditions

Volatile Flavor Compounds

Analyzed

SLIDE 2

APPARATUS FOR T€E ISOL4TION

OF VOLATILE FLAVOR CO?.fP3UIL’DS

FROM BCILED R E L F

evaporizer was maintained a t lO5OC by circulat ing heated glycerine i n the outer jacket. The water s lu r ry of boiled beef w a s , therefore, s,:>jected t o a f l a sh evaporation as it w a s released f m m t h e pump t o the vaporizer. It then flowed down the evaporizer as a t h i n f i l m under vacuum with heat supplied from outside. The vo la t i l e f lavor compounds and water were thus ef fec t ive ly evaporated and then condensed i n the cold t r aps . col lected i n the t raps was then combined, melted and extracted w i t h e the r . The ether extract was concentrated t o a volume sui table f o r gas chromatography by procedures reported by our laboratory previously.

The condensate

When the isolated boiled beef was gas chromatographed with a 20 f t . 1/8 i n . column, packed with Carbowax 2M, a large number of peaks was obtained, as shown i n s l i d e 3 . This was used as the standard p ro f i l e f o r our study on the e f f ec t of processing and storage upon the f lavor deter iorat ion of beef. complexity of t he boiled beef flavor, none of the peaks represents a pure compound.

It should be noted, however, t h a t due t o the

The isolated boiled beef flavor w a s , therefore, fractionated f i rs t by preparative gas chromatograay, using a 3/8 inch column, packed with methyl s i l i cone SE-30. were obtained. The chromatography was repeated fo r a number of times and each f rac t ion was accumulatively collected i n one t r a p . 10 were of par t icu lar i n t e re s t because these two fract ions seemed t o have a charac te r i s t ic boiled beef f lavor .

Eighteen broad fract ions, as shown i n s l i d e 4,

Fractions 6 and

Each of t he broad fract ions was then chromatographed f o r the second time, using a 1/8 inch d i a . column, packed with Carbarax 2CN on Anachrom ABS. Each of the sub-fractions thus obtained w a s again col lected. When necessary, they were chromatographed f o r t he t h i r d time, u n t i l pure compounds were obtained.

The pure gas chromatographic f ract ions were ident i f ied by the in t e r - pretat ion of t h e i r infrared, mass and NMR spectra. The ident i f ica t ion was f i n a l l y confirmed with the use of authentic compounds; when they were not avai lable commercially, they were synthesized i n our own laboratory.

A t o t a l of 57 compounds has been ident i f ied i n the vo la t i l e compounds i so la ted from boiled beef. A number of the compounds have never been reported before as components of meat f lavor and a few compmnds have never been ident i f ied before i n any food f lavor .

Eight of the cmpounds ident i f ied were hydrocarbons, one was an e s t e r , and one was an ether, as shown i n s l i d e 5 . The s i ze o f t h e peak representing the compound was indicated by "XS" i f t he peak w a s extra small, "S" i f small, "M" if medium, "L" if large and "XL" i f extra la rge .

The long chain hydrocarbons are ra ther unusual. Although hydro- carbons have been reported as autoxidative decomposition products of unsaturated f a t t y acids, those with Carbon 16, 17 and 18 have seldom been reported.

m w cl Y

80

81

-i i, 1,

1

1 c

- 0

-. -*. 1'

VOLtZTILE COMPOUNDS O F HOILFD 13EFY

lu-

Fraction Identified As L

1.

ESTER

Ethyl Acetate

HYDROCARBONS

n - Hexane

n - Dodecane

n - Pentadecane

n - Hexadecane

n - Heptadecane

n - Octadecsne

1 - Undecene

. 1 - Pentadecene

Peak Size -

S

S

11

S

S

S

L

S

XL

S

Eleven alcohols were ident i f ied i n boiled beef flavor, as shown i n s l i d e 6. extra large gas chromatographic peaks. The unsaturated alcohols have strong flavors and may s igni f icant ly contribute t o the f lavor of the food. For example, 1-octene-3-01, has a strong rmrshrom f lavor .

Two of them, n-hexanol and 1-octen-3-01, were represcc’id by

The number of aldehydes and ketones ident i f ied was not as large as expected, a s shown i n s l i d e 7. autoxidative decomposition products of l i p ids were not found i n the boiled beef f lavor . This might be due t o two reasons. One, the beef sample used was quite lean. boi l ing with water. Two, the period of boi l ing w i t h water wag r e l a t ive ly short and the i so la t ion of f lavor compounds w a s conducted in a continuous manner under mild conditions. This produced a genuine boiled beef flavor and prevented fur ther decomposition during the i s o h t i o n process, with the formation of a r t i f a c t s . of carbonyl compounds could be isolated and ident i f ied, i f the sample of beef contained excess f a t s , i f the boi l ing period were prolonged, and i f the conditions used f o r the i so la t ion of vo la t i l e f lavor compounds were such that fur ther oxidation and decomposition of l i p i d s could take place.

Many of t he carbonyl compounds which were

A l l t he excess fat was careful ly trimmed off before

It is quite conceivable that large amounts

Among the carbonyl compounds ident i f ied, two m i g h t s ign i f icant ly They are diacetyl and acetoin. contribute t o the boiled beef f lavor .

The odor and flavor of d iace ty l i s well known. Acetoin, as represented by a n extra large gas chromatographic peak, can serve as an abundant source of d iace ty l .

Five aromatic compounds, one lactone, and three acids were a l so ident i f ied as vo la t i l e compounds i n boiled beef, as shown i n s l i de 5. None of them appears t o be essent ia l t o the charac te r i s t ic hiled beef f lavor .

The most in te res t ing compounds ident i f ied i n the vo la t i l e compounds isolated from boiled beef are , undoubtedly, those shown i n s l i de 9 .

2-methyl-3-tetrahydrofuranone has recent ly been r e p x t e d as a component of coffee f lavor . laboratory as predominantly responsible f o r the reversion f lavor of soybean o i l .

2-Pentyl fu ran has been reported by our

These two compounds a re a l so found i n boiled beef f lavor .

Thiophone -2-carboxaldehyde and 5 -methylthiofuraldehyde were ident i f ied by t h e i r infrared and mass spectra. 3 ,4- t r i thiolane and 2, 4, 5-trimethyl - A3 - oxazoline a re most important because they have never been reported before as components of food f lavor .

The last two cmpounds, 2,5-dimethyl-l,

Since the t r i t h io l ane w a s a component of the broad fract ion, No. 10, and the oxazoline a component of the broad fract ion, No. 6, and since these two broad fract ions were or iginal ly determined as having a boiled beef f lavor , it w a s hoped that these two new compounds m i g h t be responsible f o r the charac te r i s t ic boiled beef f lavor .

'JOLQTILE COMPOUN9S IN ROLLED BEEF

Fraction Identified A s

ALCOHOLS

Ethanol

n - Propanol

n - Butanol

n - Pentanol

n - Hexanol

n - Octanol

Is o butanol

Isopentsnol

2 - Hexenol

1 - Penten - 3 - 01

1 - Octen - 3 - 01

Dimethyl sulfide

D irne t h v 1 4 i s ulf id e

Methyl propyl sulfide

Methyl allyl sulfide

Diallyl sulfide

Peak Size

__I

L

L

S

M

XL

M

S

xs

S

S

. - XL

xs xs

xs

xs xs

~~ ~~

*By Retention Time Only

-..--- Fraction Identified As

-- - v 1. ALDEHYDES

n - Pentanal

n - Hexanal

n - Heptanal

n - Octanal

n - Nonanal

n - Hexadecanal

Isopentanal

2 - Octenal

6 - Methyl - 2 - hepten - 1 - a1 .

VII. KETONES

Diacetyl

Ace toin

4 - Octanone

3 - Nonanone

3 - Dodecanone

L

XL

L

L

L

M

S

S

S

- L

XL

S

S

S

VOLATILE COMFOUNDS IN BOILED BEEF

Fraction Identified A s

Y1II. AROMATIC COMPOUNDS

Benzene

Toluene

n - Propyl benzene

Ben a; aldehyde

0 - Methyl kenzylaldehyde

E. LACTONE

y - Valero lactone ..

X . ACIDS

Fropionic Acid

Butyric Acid

Hexanoic Acid

Peak S i z e

L

S

S

XL

S

xs

M

M

S

__ - . - . . . - . - - . . . . . . . . - - . .. - - - - . . . . . . _. . - . -87

SLIDE 9

VOLATILE COMPOUNDS E'l BOIIAED BEEF

Fraction Identified A8

I. RING COMPOUNDS

2 - Methyl - 3 - tetrahydro - furanone

2 - Pentyl furan

Thiophene - 2 - carboxaldehyde

5 - Methylthiofuraldehyde

2 , 5 - Dimethyl - 1 , 3, 4 - tr ithiola n

2, 4, 5 - Trimethyl - A3 - ' oxazoline

Peak Size

S

M

XL

S

L

XL

Structure

s -- S

2, 5-Dimethyl-1, 3, 4-trithiol;ine w a s then prepared by the reaction 3f acetaldehyde, sulfur and hydrogen sulf ide i n the presence of diisobutylemine. 2, 4, 5-Triinethyld 3-oxazoline w a s prepared by the reaction 3f ammonia, acetaldehyde and acetoin. Unfortunately, organoleptic examinations of the two authentic compounds indicated t h a t nei ther of them had any character is t ic boiled beef flavor .

Two other ident i f ied compounds as shown i n s l i d e 10 are of' great i n t e re s t , but not because they are important t o the boiled beef f lavor . One i s dichlorobenzene, which is probably a pesticide residue. The other is BHT, which i s probably an antioxidant used i n t h e feed. The i d e n t i f i c a t i m of these two compounds i n boiled beef cer ta in ly demonstrated the sens i t i v i ty of the methodology of f lavor chemistry today.

The changes i n vo la t i l e f lavor compounds during freeze drying and storage of boiled beef were studied by the comparison of the peak s i ze i n the gas chromatograms. The Illethodology w e used fo r the i so la t ion of the vo la t i l e f lavor compounds and t h e i r gas chromatography yielded peak s izes w i t h a reproducibil i ty of 1: 5%. Therefore, any change i n peak area larger than this amount was considered t o be t rue changes in t h e concentration of the vo la t i l e f lavor compounds.

The vo la t i l e f lavor compounds isolated from f r e sh boiled beef and stored, freeze-dried boiled beef, yielded similar chromatograms when fractionated by preparative gas chromatography. devebped dwing the processing and storage. However, there were a number of s ignif icant changes of the r e l a t ive s i ze of the d i f fe ren t peaks, as shown i n s l i d e 11. storage and freeze-drying, the r e l a t ive concentration of f ract ions 1, 2 and 5 w a s g rea t ly increased, where t h a t of f ract ions 3, 6, 8 and 10 w a s grea t ly reduced. This seems t o indicate t h a t deter iorat ion of f lavor during storage and freeze-drying of boiled beef i s not due t o t h e creation of new compounds, but ra ther , due t o the change of r e l a t ive concentrations of the or iginal ly exis t ing compounds.

No new peaks were

It could be eas i ly observed that during

It should be noted that this conclusion is based upon a study of t h e storage of lean beef under an atmosphere containing less than 2% oxygen. It may not apply t o the storage of boiled beef w i t h more fa t under a n atmosphere of a i r . It is interest ing t o note tha t during storage 31' freeze-dried beef, f ract ions 6 and 10 were d ras t i ca l ly reduced. two fract ions, when eluted from the gas chromatograph, had a meaty f lavor . This seems t o correlate well with the organoleptic observation t h a t the f lavor of the rehydrated, freeze-dried and stored boiled beef was infer ior t o t h a t of the f resh boiled beef.

These

Similar techniques were used t o study the change i n flavor cmpounds, qua l i ta t ive ly as well as quant i ta t ively, fo r the deter iorat ion of the f lavor of beef stew during the canning process. Volati le f lavor compounds were isolated separately from canned beef stew and f resh cooked beef stew. The samples were special ly prepared with no spices added i n D r d e r t o avoid unnccessary complications.

SLIDE IO 1

VOLATILE COMPOUNDS IN BOILED BEIEF

- Fraction Identified A s

- Dichlorobenzene

3, 5 - Ditert. - butyl - 4 - hydroxy toluene .

Peak Size

S

M

I

:

n w -

Ul w J n H

v1

1 w

The sample of the canned beef stew was divided in to two small portions and one large portion. Volat i le f lavor canpounds from each of the three portions were isolated separately. i so la ted from the two small portions indicated t h a t the isolat ion process and the gas chromatographic analysis of the isolated vola t i les were reproducible. The gas chromatogram of the vola t i les isolated from the canned beef stew w a s then compared t o t h a t of the fresh cmked beef stew shown i n s l i d e 12. The chromatograms c lear ly indicated there were qua l i ta t ive and quant i ta t ive differences i n the gas chromatograghic peaks. Sniffing of the eff luent gas from the gas chromatograph corresponding t o each of t he peaks c l ea r ly demonstrated that the canned beef stew had l e s s t o t a l vo la t i l e s , but more and la rger peaks with undesirable odor charac te r i s t ics , such as burned rubber and burned sugar.

The gas chromatograms of the vola t i les

Ident i f icat ion of the chemical nature of the peaks, which are e i ther qua l i ta t ive ly or quant i ta t ively d i f fe ren t i n the vola t i les isolated from the f resh beef stew and the canned beef stew, i s now i n progress.

Since a considerable amount of work had been done and no gas chroma- tographic f ract ion with charac te r i s t ic boiled beef flavor w a s ident i f ied, we began t o question the v a l i d i t y of using gas chromatography fo r the fract ionat ion of boiled beef f lavor . compound or compounds with the charac te r i s t ic boiled beef f lavor were retained on the column due t o the i r high polar i ty , or were decomposed under the high temperature of gas chromatography.

We began t o wonder whether the

In order t o t e s t t h i s suspicion, a new batch of v o l a t i l e f lavor compounds was isolated. The isolated vo la t i l e f lavor c0mporn.d~ we,-e separated i n t o an acidic , a basic and a neutral f ract ion, as shown i n s l i d e 13. The acidic compound had no flavor and w a s discarded. The basic f rac t ion had a strong, nutty f lavor . chromatography and the gas chromatographic f ract ions were ident i f ied by a combination of infrared and mass spectrometry. Among the compounds ident i f ied were 2,5-dimethyl pyrazine and 2-ethyl-3,6-dimethyl pyrazine .

It was fractionated by gas

The neutral f rac t ion had a strong, pleasant boiled beef f lavor , When a small amount of t h i s f rac t ion was dissolved i n water, it yielded the desired boiled beef f lavor .

hken the neutral f rac t ion was injected in to the gas chromatograph, with e i t h e r a Carbowax 2C.M column or methyl s i l icone SE-30 column, the t o t a l eff luent condensate appeared t o lack the character is t ic boiled beef f lavor , as shown i n s l i d e 14. temperature. Again, the desired boiled beef flavor was los't, a f t e r the sample was gas chromatographed .

We t r i e d t o lower the inject ion port

These experiments lead us t o believe t h a t the compound or compounds with the character is t ic boiled beef flavor simply could not be gas chromatogramed. Therefore, we decided t o develop an automatic, high- pressure l iquid column chromatographic method which does not require the high temperature of gas chromatography, t o f ract ionate the vo la t i l e f lavor compounds isolated from boiled beef.

- - 92' - - . . . .- . . - . . . . . . . - - . _. .

2 w n J VI

r r-

E 0 k

W

0 N

t;

0) C N rd k h

.r(

PI h

d $. c, x 3 c,

5 z c .r(

CI '",

M E 0 k .c) I

m

N

t

! !

61 f? 4 5 c-1 61

a I$ k E+ 2 0 u e a 0)

.rl

z Q, P c 0 V

The apparatus we used w a s assembled from components made by a i f f e ren t companies. This has a t least th ree advantages. One, it can u t i l i z e the unique, desirable designs of several companies. Two, it is easier t o modify and repair the d i f fe ren t cmponents . Three, it is more economica.1.

"he micro bore glass columns of inside diameters 1, 2, and 3 mm. were made by Chromatronix, Inc., Berkeley, California. Connections and injectors were made of Teflon. This setup can stand 500 p s i of pressure. Metal columns were avoided t o prevent adsorptions and s ide e f f ec t s . The solvent was delivered i n t o the column by using a model CMP-2 pulseless pump from Chromatronix, Inc. This pump is su i tab le f o r organic solvents and can del iver solvent a t a constant f l o w r a t e up t o a pressure of 500 p s i .

The ef f luent from t h e column was constantly passed through a model 200 W detector, manufactured by Chromatronix, Inc . This detector has a c e l l capacity of only 8 pl. recorded by a Beckman l inea r 10-inch recorder of 10 m v . from the detector was then collected by a Buchler automatic f rac t ion co l lec tor

The adsorption a t 254 mp was continuously The eff luent

Eight lmown compounds, which were previously found as components of boiled beef f lavor , were pur i f ied by gas chromatography. each compound required t o give a 25% recorder response i s shown i n s l i de 15

The amount of

Theoretically, Undecane should not show any adsorption a t 254 mp. The response might, therefore, only be due t o the change of t he solvent f ront i n the detector .

The r e su l t s appeared t o be qui te sat isfactory, as the ones with even the lowest s ens i t i v i ty correspmded t o the sens i t i v i ty of an ordinary thermal conductivity detector of a gas chromatograph set a t an attenuation of 2.

The m a x i n u mount of samples appliable t o a Sil-X column, one mm. ins ide diameter and one m. in length, is shown i n s l i d e 16. amount which can be injected in to the column without any s igni f icant l o s s i n resolution. These results also appeared sa t i s fac tory because t h e amount the one mm. I . D . column can handle is s igni f icant ly higher than the sens i t i v i ty of t he detector . Furthermore, this amount is ?ilr:7 more than enough f o r the determination of the infrared and mass spectra of these compounds.

This i s the

The high pressure l iqu id chramatography j u s t described i s then applied t o separate a mixture of the eight known compounds. When a Sil-X column w a s used, only f i v e d i s t i n c t peaks were observed, as shown i n s l i de 17. It is, therefore, evident t h a t the separation cannot be accanplished by j u s t using one column. A scheme, using the conbination of d i f fe ren t columns t o separate these eight known cmpounds, was, therefore, designed and carr ied out a s shown i n s l i d e 18.

SLIIJE 15

RESPCINSES OF CHROMATRONIX MODEL 200 UV PHOTOMFTER

Compound

(W Amount Required =or

25% Recorder: F t$sponse -

Und e can e 0.02

Butyl Acetate 0.015 I

Nonyl Alcohol 0.02

3 -Heptanone 0.006

'3-Decanone 0.007

Butyl Benzene 0.0004

y-Valerolactme 0.01

Phenyl Ether < 0.0005

97 SLIDE 15

AMOCI'JT OT SAMPLES .APPLLIBLT;' TO A SIL-X COLUMN

(1 mm I.D. x 1 mm)

c

COMPOUND )rl

Undecane 0.48

.- Butyl Acetate 0.30 - Wonyl Alcohol 0.36

3-Heptanone 0.36

3 -De can0 ne 0. 36 -

Butyl Benzene 0.08

y -Vale r olact one 0. 30

Phenyl Ethe r 0.04

, f'

!

100

90

8C

7c

6C

5(

4i

3(

2(

1C

c

CHROLMATOGRAM OF A MIXTURE CF EIGHT KNOWN COMPOUNDS

U

Column: 1 m x 1 mm I. D. G l a s s Colurnn Packing : Solvent: Hexane to Chloroform Gradient Flow, Rate: 24 ml/hr. Pr e s sur e : Temperature: 2 5OC

Nester - Faus t SIL-X

300 p s i

t I I I I I I I I I 1 I 1 I

0 5 10 15 20 25 30 35 40 45 50 55 60 5 5

Time (Minutes)

SLIDE 1.7

i

3

a w 2 E 61 d 3-( a

b.4 0

X J

I

W VI

99

t

I

!3 V I 4 .A : k ' 0 V

0 1 w G

100

'The mixture of t h e eight known cmpounds w a s f irst separated by Sil-X adscrptim chromatography, using hexane t o chloroform i n gradient e lut ion. Among the f ive peaks obtained, only peak 5 was a pure compound, Y-valerolactone. Fraction l w a s separated in to two fract ions by reverse phase par t i t ion chromatography, using ETH and 4 9 methanol i n water. base s ta t ionary phase, permanently bound on porous glass beads, mnnufactured by DuPont. The first fract ion w a s ident i f ied as 3-dccanone. The second fract ion w 2 s further separated by reverse phase par t i t ion chromatography, using Corasil-C 18 and 48% methanol i n water. Corasil-' 7 0 is octadecyl t r ichlorosi lane, permanently bound 3n porous glass beaus, produced by Water Associates. Between the two fract ions sbtained, one was butyl benzene. The other f ract ion w a s f i n a l l y sc ' i.tited by adsorption chromatography, usir?g Vydac and hexane. i n e r t support, produced by the Separation Group. obtained, one w a s a m i x t u r e of phenyl ether and undecane, and the other was nonyl alcohol.

ETH i s a s i l icone

Vydac i s a s r ec i a l ly activated s i l i c a coated on h n g the four f ract ions

The second f rac t ion obtained from S i l - X was fur ther fractionated by Corasil C 18 reverse phase pa r t i t i on chromatography, using 3% methanol i n water. One f rac t ion thus obtained w a s pure butyl acetate and the other was 3-heptanone. It, therefore, appeared that the mixture of eight known compounds which were previously ident i f ied i n boiled meat could be successfully fractionated by t h i s scheme of repeated high pressure liquid chromatography .

CONCLUSION

The vo la t i l e f lavor compounds i n fresh boiled beef have been isolated, fractionated, and ident i f ied . The gas chromatogram of the vola t i les isolated from f resh boiled beef was compared t o t h a t of t h e vola t i les isolated from aged, freeze-dried boiled beef. The sane method was used t o study t h e changes i n vo la t i l e f lavor compounds which a r e responsible f o r t he deter iorat ion of beef stew during the canning process. A high- pressure, l iqu id column chromatographic procedure was developed t o fur ther study the vo la t i l e f lavor compunds of boiled beef which m i g h t have d i f f i c u l t i e s i n p a s s b g through the gas chromatographic column.

101

AARON WASSERMAN: May I ask p u a question, D r . k e . You m i d t h a t Fractions 6 and 10 had a boiled beef f lavor . They went through the gas chromatograph a l l right and did not l o s t t he flavor?

-

DR. LEE: "he Fractions 6 a d 10 were reminiscent of a meaty f lavor . They were not exactly boiled beef f lavor .

JOHN SINK: One announcement before the break. D r . Hedrick.

HAROLD HEDFUCK: I w i s h t o announce the r e su l t s of the elect ion we had j u s t before lunch. the Board of Directors: John Morrell and Co.; and Steve Zobriski, CSRS.

The following three persons have been elected t o Gary Smith, Texas A & M University; B i l l Kramlich,

Remember that there w i l l be a business session a t 4:O'j. We w i l l be e lec t ing a Chairman of the Reciprocal Meat Conference for next year from these three candidates: Fred Parrish, Jim Christian and Warren Tauber. One other announcement--the Personnel Cornnittee has some arrangements s e t up i n Room 115 f o r those who are seeking employment and those who a re seeking employees. They might ge t together and Vern C a h i l l w i l l be happy t o assist you i n any way they can.

Charley Adams, Gene King

W e w i l l now adjourn f o r t he break.

AARON WASSER14AN: As you see, there a r e large numbexsof canpounds present i n these extracts and aromas that the beef people have been studying. that had beef aroma has been almost impossible, as D r . Lee has mentioned. The idea has been that perhaps w e could blend some of these compounds but I think t h i s has a l s o been qui te a t a sk . material, however, and today we are going t o hear something about synthetic meat flavors both from a chemical standpoint and as t h e i r possible use i n preparations i n w h i c h enhancement of meat flavor is desirable. on the subject i s D r . Ira Katz who is Director of Flavor Research f o r Internat ional Flavors and Fragrances.

As you can imagine, t rying t o f b d one par t icu lar canpound

There have been other sources of

To speak