CA1047306A - Synthetic meat flavors for texturised vegetable protein - Google Patents

Synthetic meat flavors for texturised vegetable protein

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Publication number
CA1047306A
CA1047306A CA219,083A CA219083A CA1047306A CA 1047306 A CA1047306 A CA 1047306A CA 219083 A CA219083 A CA 219083A CA 1047306 A CA1047306 A CA 1047306A
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Canada
Prior art keywords
protein
plastein
weight
process according
product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA219,083A
Other languages
French (fr)
Inventor
David A. Jonas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Corp
Original Assignee
Pfizer Corp
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Filing date
Publication date
Priority to GB735074A priority Critical patent/GB1469331A/en
Application filed by Pfizer Corp filed Critical Pfizer Corp
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Publication of CA1047306A publication Critical patent/CA1047306A/en
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Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/21Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning

Abstract

ABSTRACT OF THE DISCLOSURE
A novel process for preparing a flavoring agent by reaction of a monosaccharide and a plastein supplemented with a sulfur-containing amino acid in the presence of water at 80 to 120°C., and the product thereby obtained, as well as meat-flavored textured protein compositions having incorporated therein 0.1 to 10% by weight of the above flavoring agent.

Description

3~i ~ ~ ~r t~e 1~
This invention relates to flavoring a~ents and particularly to agents for imparting a meat flavor to protein compositions, especially textured vegetable protelns. The invention iæ also concerned with ~lavored protein compositions, part~cularly flavored textured vegetable protein compositions, whlch have been flavored with the said flavoring Qgents .
Descri~tl ~
Unlted Kingdom Patent Speci~ication ~o. 1,082,504 describes and claims a process ~or preparlne a beef-~lavored substance which com-prises heating in admixture, a hexose or pentose monosaccharide with cysteine, in the presence of water, untll a bee~-~lavored mlxture is obtained, addin~ ~or each part by weiæht o~ said beef-flavored mixture ~rom 5 to 15 parts o~ vegetable protein hydrolysate and from 0.5 to 1.5 parts o~ a 5'-r-lbonucleotide and heating for about 2 hours at least 70C.
United Kingdom Patent Speci~ication No. 1,135,123, ~hich is a Patent of AdditiQn to No~ 1,082,5Q4, describes and claims a similar process and include~ the u~e o~ cyqtine as the amino acidO
It ha8 now been found that a process similar to that dlsclosed in Specifica~tfqns 1,082,504 and~l,l35,123, and in t4e corresponding Unlted Sta~es Speci~ication 3,365,306, but inYolving the reaction of qupplemented plasteins bith mo~osaccharides provides improved meat ~lavor compositions.
Thè plastein reaction is know to be an enzymatic process for .

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the growth of peptide chains, i.e., the reversal of the usual protein degradation by proteinase (see for ex~mple, Yamashita et al- J- of AOE~
~nd Food Chem.. ~, 1151 (1971~, and re~erences cited therein.-'rhus, ~ plasteins are a mixture of protein-liXe high molecular weight compounds formed from lower molecular weight fragments. The plasteins ~hich have been found to be advantagebus for the production o~ flavoring agent~
are those which have been supplemented wlth sulphur-containing amlno acids, ~or example methionine or cysteine. Since the presence Or lo~
molecular weight peptides or free ~nino acids may lePd to off flavors they may optionally be re ~ed by, ror example, dialysis or fractional precipitation.
Meat flavors are rormed by the reaction of these supplemented ;~
plQsteins with monosaccharides (hexose or pentose) in water at elevated temperature, this reaction being known as the Maillard reaction, the re~ct~on o~ the ani~o ~roup of an amino acid molety ~ith the glycosidic hydroxyl group of ~ monosacchsride, followed by otherl more complex change~ which resuit in the formation of brown pigments (See the Merck Index, 8th Editlon9 p. 1189,1968).
The rla~or may be diried by the addition of known fla~or difier~ such BS ~onosodium glutamate, be~ore reaction with the mono-sacchQride.
Su~mary of the Invention ~ he in~e~tion comprises a proce~s for preparing ~ flavoring sge~t by the reaction o~ a mixture Or one part by weight o~ a hexose or pentose monosacchnside snd ~rom about one to ten parts by wei~ht of ~
plssteip suppleme~ted with a sulfur-containing amino acld in an gmount of ~rom 5 to 50~ by ~eight based on the supplemented plastein ~aid reaction i8 carri~d out by hesting the miYture in the presence o~ ~at~r a$ a temporature in the ran8e of ~bout ôO to 120C., and the flavorin4 age~t pr~pared by the said process.

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3(~i The invention al80 provides a meat-flQvored textured protein composition having incorporated therein from about 0.1 to 10% by weight based on the dry weieht of textured protein, of the flavoring agent prepared by the above-mentioned process.
Detailed Description of the Invention ~he present invenkion provides a process for the preparation of a flavoring agent which comprises mixing together one part by weight of a hexose or pentose monosaccharide and from 1 to 20 parts by weight, -preferably ~rom 4 to 10 parts by weight, of a plastein supplemented with a sulphur-containing amino acid, and heating the mixture in the presence of ~ater at a temperature in the range of about 80 to 120C. If deslred, the flavor ma~ be ~urther impro~ed by including in the mixture, preferab1y before heating, a flavor modi~ier, e.g. monosodium glutamate.
Preferably, the heating is conducted for at least four hours .
at 100C., although the heating period may be correspondingly shorter or longer at higher or lower temperatures, respectively. When conducting the reaction at a temperature at the upper end of the specified range, i.e. above 100C, it will clearly be necessary to operate under an elevated pressure.
It has been ~ound in accordance with the invention that the heating perlod necessary to complete reaction varies according to the mono9accharide used. For example, a hexose (such as glucose) requires a period o~ at leart 20 hours at 100 or at least 5 hours at 120 (under elevated pr~s~ure), while a pentosr (such ribose)requlres only 4 hours at 100 or l hou~r at 120.
~ As alr~ady~mentioned, the pre~erred ratio (by weight) of mono-s`acoharide to plastein is in the range from 1:4 to 1:10, and it has been ~3und in accordance with the invention that ratios lower than 1:10 impart :
~rather weak ~lavors bo protein compositions in which the flavoring agent 30 ~ ir incorporated. As the ratio is increased above l:lO, undesirable off-' : :

~0~73~!6 flavors begin to appear in such compositions, but these only become strone at ratio~ a~ove 1:40 Thus the optimum ratio is about 1:10.
The monosodium glutamate may be included in the mixture ak ra~ios of one part to from one to ten parts be weight o~ plastein, preferably one part to about five parts by weight of plastein. At a ratio of less than 1:5 the ~lavor improvement is rather weak, while at ratios above 1:5 little further advantage is obtained.
The water content of the mixture i~ also important ~or flavor quality and depenas on the monosaccharlde used. ~he amount of water present ~hould in all ca~es be 3uch as to provlde at least two parbs by weight of water for each part o~ supplememted plastein. With a pentose (such as ribose) improvement in flavor guality increases wit~ amounts of water up to five parts by weight of ~ater, but further incr~asing the amount o~ waber, although not deleterious Q8 bo fla~or qualiby, merely d~lute~ the product. Th~ preferred ratio of water bo ~upplem~nted plastein when a pento3e i9 u~ed is therefore about 5:1. With a hexose (such as ~luco~e), however, improvement in ~lavor quality conti~ues ~ith increa~in~ amounts o~ ~ater up to twenty parbs by weight o~ water. The prererred ratlo o~ water to suppleme~ted plastein when a hexo~e is u~ed is therefore about 20:1.
~ince the optimum rabio o~ plastein to monosaccharide is about 10:1 and the prererred r~tio of plastein to mono~oaium glutamate iB about 5:1, the preferred water ~ontent of the total mixture before hea~ing, when a pentose is used ls 5 parts by weight of water in 6.3 parts of the mixture, i.e. about 80% water by wei~ht, and when a hexose is used, is 20 parts by weight of water in 21~3 parts o~ the mixture, i~e. about 94% water by weight.
The in~ention also provides a ~lavoring agent whenever prepared by the above process.
The supplemented plastein used In the proces~ o~ this invention ini-tially may be prepared ~rom a hydrolyæed protein, e.g~ digest derivéd ~rom soya protein~ ~af~lower protein, peanub protein~ cottonseed protein or other vegeta-

-4- -~0~ 3~6 table protein, fish protein or microbial protein, such as ~ungal protein, with a proteolytic enzyme, e.g. pepsin. The hydrolyzed protein is concentrated, sup-plemented with a sui~able derivative of a sulfur-containing amino acid, for example, methionine, cysteine, cystine or lanthionine, and the suppl~mented plastein is then prepared by incubating the hydrolyzed protein together with the sulfur-containing amino acid or a derivative of the amino acid, for example an alkyl ester or a salt thereof, in t~e presence of a further amount o~ enzyme under condition~ such QS to cause polycondensation to occur. Preferred alkyl groups in the alkyl estçrs o~ the sulfur-containing amino acids are those con-taining from about one to ~our carbon atoms. Examples of suitable derivativesare the methyl ester o~ Dl-methionine, ethyl ester of L-methionine, n-propyl ester of DL-cysteine, isopropyl ester of L~cy~teine, n-butyl ester o~ DL-cysteine hy~rochloride, dimethyl-L-cystine, dimethyl-L-cystine dihydrochloride, diethyi-DL-cystine sulfate, diisobutyl-meso-lanthionine, dimethyl-L-lanthionine dihydrochloride and dieth~l-D-lanthionine dih~drobromide.
The preparation of plastein from hydrolyzed protein has been known ~or a ~ery long time and the conditions for plastein formation are also well known (see, ~or example, Cuthbertson et al., Biochem. J~ 1931, 25, 2003)~
Supplementation with methionine hQs also been previousl~ described by Y~bbhit~, ¦ bl., J. A~ric. Food Ohb~., 1971, ~, 1151.

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The product may be either dried as such, ior example by free7e-drying, or further treated by ~ialysis or fractional precipitation e.g. with ethanol, j, . .
~to remove undesirable by-products which might produce oEf-flavors.
. The amount of sulEur-containing amino acid which may be used for ¦jsupplementing the plastein can vary within wide limits but is normally in the Irange o~ from about 5 to 50% by weight based on the supplemented plastein, and 'Ipreferably from about 15 to 20~, since lower proportions lead to weaker meat flavors in the ultimate product while proportions greater ~han 20% can lead to 1the appearallce of off-flavors. ~ i 10l~ ~ The supplemented plastein prepared as described above is then heated ¦¦with water and the hexose or pentose monosaccharide, for example ribose, glu- ¦
jlcose or arabinose, and optionally the flavor modifier, for example, monosodium ~¦glutamate, to produce a flavoring agent according to the invention. A parti-¦ cular-advantage of meat flavors formed from~plasteins in this way is their pro-151 perty of being only slowly liberatedjfrom protein compositions containing them when the latter are chewed. They are thus useful for flavoring materials ¦requiring a good deal of chewing, such as textured proteins and especially ¦textured vegetable proteins such as~soya protein. In such a situation it may Ibe advantageous to supplement the plastein derived meat flavor with a more I
20ilrapidly released meat flavor which may be of synthetic or natural origin, I
~iPor example, the beef-flavored substances of Um ted States Patent No. 3,365,306 ',and United Kin~dom Patent ~os. 1,082,504 and 1,135,123, and the chicken and ¦¦beef flavored products marketed by Pfizer Inc., under the Trade ~lark "Corral", 1-l or they may be of natural origin, for~example, natural m2at stocks or ex~racts.
The~flavorlng agents of~the present invention may be incorporated in '`the finished textured protein product, together with other meat flavors iE
i : : - I
de9ired,~by contacting~the protein product with an aqueous solution containing the fIavoring agents. It has been found, in accordance with a further aspect !¦ of the invention, however~ that the Elavoring agents of the present invention 30~ can be incorpo~ated in the textured~protein belore it is shaped into its ii ` ~ ' . : ' ' ~04730G
finished form, e.g. b~ incorporation in the protein before extrusion at hiBh temperature and pressure, sinoe the ~lavoring agents o~ the present invention are not inactivated at the high temperatures and pressures u~ed in ~uch pro-cesses, e.g., temperature of about 100 to 150C. and pressures of about 300 to 3000 pounds per square inch.
Textured protein products ma~v be defined as food products made from edible protein sources and are characterized b~v having structural integrity and identifiable texture such that each unit will withstand hydration in cooking and other procedures used in preparing food for consumption. ~extured proteins, especially textured so~a protein are well known in the art, see for example, Gutcho, "Textured Foods and Allied Products,1' No~es Data Corporation, 1973 and refere~oes therein.
Examples of proteins w~ich may be employed in the invention to form the above described compositions in which the flavoring agents of the inven-t1on are incorporated into the textured protein products or incorporated into the protein product prior to texturizlng by exbrusion are ~oya protein, saf-flower protein, peanut protein, cottonseed protein, casein, ~ish protein, mlcrobial proteins and other edible protein and protein containine products well kno~n to those skilled in the art.
Accordin~ly, the present invention further provides a textured pro-tein composition, especlally a meat-flavored textured ~egetable protein compo-~ition, whioh comprises a textured protein, for example a textured vegetable protein, haYing incorporated therein from 0.1 to 10 per cent by weight, pre ~erably ~rom 0.75 to 6% by wei~ht, o~ a flavoring agent o~ the invention, based on the dry wei~ht of textured protein.
Th~ following Examples illustrate the preparation of flavoring agents acoording to the in~ention and the production o~ textured proteln co=positions incorporatin6 such ~lavoring agents. Unless otherwise seated 11 peroenta~es are by weight and temperatures are in C. In all cases pepslD used ia 1:10,000 erade.

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3~6 EXAMPLE I
ta) Hydrolysis of Soya Protein A aommercial soya protein isolate, Fu~ipro M, ("Fujipro" is a Trade Mark) is used as ~tarting material.
500 g of Fujipro M is dissol~ed in 22.5 litres of demineralised waker and the pH adjusted to 1.60 with hydro-chloric acid. The solukion is heated to 37 and 5.0 g of pepsin is add~d, the whole is then incubated at 37 ~or 40 hours by which time the nitrogen containing material ls 98.5 soluble in 10% trichloro-acetic acid (TCA). The mixkure is boiled for 15 minutes, ad~usted t~ pH 5.0 wlth aqueous sodium hydroxide and filkered. The filtrate contains 0.26% w/v nitrogen ~f which 99.3% is soluble~ in 10% TCA. The filtrate is then concentrated to about 40% protei.n by evaporatlon under reduc~d pre~sure a~
40C., to give a substrate which is suitable for plast~in ~ormation.
(bj 50.0 ml. o~ concentrated peptio digest obtained as in (a) and containing 46.6% w/v protein with a degree of pro-~eolysis of 99.3% (i.e. 99.3~ of nltrogen is 301uble in lO~
TCA) is mixed wi~h 5.0 g of L-methionine ethyl e~ter and the whole is heat~d to 37C. 0.25 g. o~ pepsin ls added and the whole inaubated~at 37C , ~or 24 hours.
~ ~he product may be freeze dried and a~ such con~ains 77.1~ of it~ nitrogen soluble in 10% TCA, repre enting a pla~tein 25 ~ ~ yield of 20 5~based on the hydrolysed protein plus;methionine~
Alternatively, the product ma~ be dialysed again~t demi~nerali-~ed~water for 48 hours, which lowers the amount o TCA~so~luble nitrogen to 56.2~, and subsequently reeze dried.
~Either product m~y be used for f~avor ~ormation through -the ~ dialyséd ma~erial is preferable~
~ 8-4~3at6 (c) Flavor Agent Formation 1.0 g of the dialyzed powder prepared above 0.5 e. o~ ribose and 0.3 g. of monosodium glutamate are heated in 10 ml. o~ water at 100C. for 4 hours and freeze dried. The resulting product has the fla~or o~ cooked beef.

(a) 5 k~. of FuJipro M is suspended in 200 litres of deminer-alised w&ter and the pH ad~usted to 1.6 with 1.4 kg of concentrated hydro;
chloric acid. The mixture is then heated to ~50~, 50 g o~ pepsin (1:10,000 grade) is added and the whole is heated and ætirred at 50 ~or 4 hours. The temperature is then raised rapidl~ (in 15 minutes) to 80, while 40% caustic soda is added to raise the pH to 5.0, and held at 80 for 30 minutes. After coolin~ overnight, the pH of the mixture is read3usted to 5.0 with caustic soda thus uslng a total o~ 600 g sodium hydroxide. ~he product is filtered and concentrated to ~ protein content o~ a~out 46% in a final ~olume of 7 litrQs. The protein content is 80.2% soluble in TCA, i.e. has a degree o~
proteolysis o~ ôO.2%, and has an average molecular weight o~ 1050, as deter-mined b~ end-~roup analysis, ~bj ~o 605 litres of the product o~ (a) containing 3 kg of ~ydrolyzed protein (ôO.2% soluble in 10% ~CA) is added 750 g. (25%) of DL-mothioninQ ethrl ester and the pH o~ the solution is ad~usted to 4.5 with 300 o~ c~nc~ntrated h~drochl~ric acid. The solut1on is then heated to 55, 4 g o~ pepsin is add~d and the whole i9 maintained at 65 ~or 24 hours to yield a ~is~ous aQUeous paste containing Q 3.62 kg if plastein. ~he pla~tein thus produced has~a methlonine content o~ 550 g (15%) and contain~ 45~4f o~ its nitrogen soluble~in 10% ~'CA (representing a plastein yield o~ 35%) a~d an ~ aYerQge moleoular weight Or~5,800.

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1¦ - Suspension of this material in 75 litres of industrial methylated j spirit (95:5 ethanol:methanol mixture) and stirring for 2 hours yields an insoluble precipitate wbich, after iltration and drying in vacuo, yields ~; 3.55 Icg of a white powder, containing 95% plastein with an average molecular 5 1¦ weight of 6,400.
! (c) ~oo g of the paste obtained in (b3, before precipitation ` with methylated spirit, containing 375 g of plastein, is mixed with 40 g ~' - ' ' i ~ ribose, 80 g monosodium glutamate and 2.0 litres of water, heated under reflux ¦~ for 4 hours, cooled and made up to 2.5 litres with water. The product is an i lOIi~ aq,ueoos solution containlng about 20% by weight of a flavoring agent according to the invention, and comprising 15% ~g.llO0 ml.) plastein.

The procedure of Example 2 is repeated usin~g amounts of DL-methioninle 15~ ethyl ester in part (b) varying from 150 g to 3 kg (5% to 100%iby weight, bas~ed;~on the hydrolysed proteln to af~ord products containing Erom 5% to 50%
methionine. While all products demonstrated acceptable meat flavor; those con;taining lS to 20Z methionine were oE especially good flavor quality ;and strength. ~ I -20 !~
~ EXAMPLE 4 ~ , `t` - ~
: ~ .... : i ~ .
The procedure of Example 2 is repeated using DL-methionine ethyl :: ~ ~
ester~hydrochloride in~ part (bj in place of the free ester, with ~slmilar results.~

s;
. ; EX~LE 5 ,l The proceclure of Examp].e 2 is repeated usin~ the following sulfur~ j ! containing amino acids or amino acid derivati~es in part (b) in place of DL- I
i methionine ethyl ester with similar results.
.5 , L-cysteine hydrochloride monoh~drate 11 -. DL-cysteine methyl ester .
¦ . L-cysteiren-butyl ester .
;I DL-cysteine isobutyl ester hydrochloride ~ . L-methionine isopropyl ester 10 l ~ . DL-methionine n-propyl ester hemisulfate .
- ! I DL-methionine , .
l . ., . . . ' .~ ~ , . ' . .
- ll L-Cystine .
~ L-Cystine dimethyl ester dihydrochloride - ll DL-Cystine di-n-butyl ester .
15 I ` ~ DL-Cystine di-n-butyl ester dihydrobromide ~ t~
. . . -: a mix~ure of DL and meso lanthionine ~ .
. ¦ ~ . meso lanthionine diethyl ester - ~
: . DL-lanthionine dimethyl ester dihydrochloride ¦

20 ~ . E~A~LE 6 . ¦
``-` il .' - . : . .,, ~ :., 1 ~¦ The procedure:of Example 2 is repeated using amounts of ribose.in part ~j(C) varying from 18 to 375 8. with simiIar results. . . ... P

. ¦ ~ EXAMPLE 7 -~ ..
~ .~ :
. ~ : : ~The procedure of Example 2 lS repeated using an equal weight of glu- .
`cosé or arabinose in~place~ of ribose in part (c?, and heating under reflux for 20 hours~, wirh~similar;~results.

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~4~3~6 EXAMPLE_8 The procedure o~ Example 2 is repeated usin~ amounts o~
m~nosodium glutamate varying ~rom 35 to 400 g. with similar results.

The procedure o~ Example 2 is repeated7 except that in part (c) heating is carried out (under elevated pressure) at a temperature Or 120 ~or l hour, wlth similar results.
EXAMPLE lO
The procedure o~ Example 2 is repeated, except that in part(c) heating is carried out at a temperature o~ oOC. ~or 16 hours with similar re~ults.

~he procedure o~ Example 2 is repeated, but using amounts o~ water in part (c) varying from 750 ml. to 4 litres, with similar results.

~he procedure of Example 2, parts (a) and ~b) is repeated, but (c) iB replaced by the;~ollowing:
~00 g o~ the ~lnal powder proauct o~ (b)a containing 300 g plastein i8 mixed uitb 40 g rlbose, 80 g monosodium glutamate and 2 11tres 20 of water, heated at 100 under re~lux, coeled and the solution made up to 2.53 ~. litres with water. ~he product is again a~ a~ueous solution con-bainin~ aboub 20% by wei~ht o~ a ~lavoring agent according to the invention, and ~ompr1s1nc 15% (g.jlOO ml.) plaste1n.
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~ 12- -10~73~6 j ! ~XAMPLE 13 ~ .

iThe procedure of Example 2, parts ~a) and (b), is repeated, but (c) !
is replaced by the following: i 200 g of the final powder product oE (b), containlng 190 g plastein, ~ is ~ixed with 20 g glucose, 40 g monosodium glutamate and 4 litres of water, ¦, heated at 100 for 20 hours, cooled and the solution n1ade up to 5 l.itres with ~
. water. The product is an aqueous solution containing about 5% by weight of a .
! flavoring agent accordlng to the invention, and comprising 3.8% (g.llOO ml.) plastein.

Ii. . -, ' ' , : .
~ . EXAMPLE 14 ¦
lO I The procedure of Example 13 is repeated, except that heating is !

¦I carried out (under elevated pressure? at a temperature of 120 for 5 hours, with .
i similar results. ~ , EXAMPLE 15 ~ ~ ~ ~ I :
~ - Preparatlon of.flavored, textured vegetable Protein (TVP) ~¦

. - 15 ¦ A mixture of 10 g dry, textured soya protein ~produced by extruding i . I wet so~a flour or grits under high pressure at;a temperature above 100C.),O.lg. .
. ¦ of the:freeze-dried product o~ Example l and 25 ml. of a lO~ (lOgllOOml) aque- , ll, ous solution of~"Corral" beef flavor paste are heated in a stoppered tube at ¦ .
¦¦ 90 for 2 hours. ~ .

20. The product, which lS a re-hydrated, texturised vegetable protein ~
: ~contalning the equivalent of 7% "Corral" beef flavor paste and 0.3% of a I i . ~ 1avo~iog a8ent according to the present invention (based on the wet weight the product) has tlie taste and texture:of cooked beef and has a long-lasting ~ll bee ElavQr,~

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~ j . l !i 7~6 !

A similar product made with "Corral" beef flavor paste alone, ~7ithout ,I the flavoring agent of the presen~ invention,has a similar flavor which is muchi ¦ more quickly lost on chewing and is therefore an inferior product.
! Corral beef flavor paste is a product sold by Pfizer Inc. of New 5 , York, New York, r.s.A. and is a flavoring composition made in accordance with ,I the disclosure in United States Specification No. 3365306 and United Kingdom ¦¦ Specification No. 1135123. ~ ~
Il ' - ' . . .
Il ~ EXAMPLE 16 1 10; When the procedure of Example 15 is repeated wi~l~ 0.05%, 0.1%, 0 5%~ !
0.75%, 2%, 5%, 6%, 7%, 10% and 20% of~the freeze dried product of Example 1 , (percentages based on weight of dry, textured soya protein) and the rehydrated t texturized protein products evaluàted for flavor quality and~~duratibn,the !~ following results are obtained. ~
.lsl! . ` -. . -.. .
¦ Weight % of Product of Example 1 Comments `
¦ 0~00 ~control) meaty, non-persistent 'I 0.05 meaty, not appreciably different from con-i` troI - I
20 !l 0.1 meaty, slightly longer lastlng than control¦
i i ~ ' ' ~ 11 0.5 , meaty, appreciably persist~nt ~
. ~ ';, 0.75 meaty, persistent - 5 i; 2 ~ ~ meaty, persistent ~ !
.
'~ S. ~ meaty, persistent 25.... ~ ~;6 ~ meaty, persistent ¦~
7~ meaty,~persistent, trace of bitterness !
o ~ meaty,~persi8tent, trace of bitterness ` . 20 ~ ~ ~ meaty, persistent, b~t bitter tasting.

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Il . EX~ E 17 ¦¦ When the procedure o~ Example 15 is r~peated but the textu~ed soya ji protein is replaced in each case by textured safflower protein, textured 1 peanut protein, textured cottonseed protein or textured casein, similar l results are obtained.
' ~' ~

. One part of dry textured soya protein product produced afi in .
I Example 15 is re-hydrated with two parts (by weight) of an aqueous solution .
¦¦ of either "Corral'l beef (or chicken) flavor paste alone or "Corral" beef ¦1, (or chicke~) flavor paste and a product of one of Examples 2, 12 ~r 13, to ¦ give a flavored product containing the amounts o~ flavoring material (or j materials) shown in Table I as wt % "Corral" paste or plastein content oE
¦ product of Examples 2, 12, or 13, based on the weight of hydrated product.
. I The flavored products are tested for flavor quality and persistence on cheuing 15 I by panels of judges, scored on an arbitrary scale for quallty and ranked for l I
¦ persistence in each of the groups ~A) to (~) containing different proportions I .
. . . I of a "Corral" flavor and a flavor of the present invention. Results a~e also¦
¦ shown in Table I. l . I . ~, ............................ . . I
¦ : TABLE I . ¦ I
~0 ll (1) (2) (3) l Il (A) "Corral" beef flavor past:e? % . 4.5 3.62.7 !
` I! ` Product of Example 2, % plastein 0.0 0.5 1.0 ¦
¦¦ Flavour ficor.e . 102 116 129 I¦ Mean rank for persistence . 2.33 2.00 l.S?

' ` 11 ' ' ,, ' ' ' ' ~

~-1 -: ~ ' . ' ` '. . .1 ' " '~ ' '` ' ' , ' ' ' .. I '' , ' :' I
., ~j, ' . , .
I! `

1 1 0 ~ 7 ~ 0 ~ (1) (~) (3) I (B) "Corral" beef 1avor paste, % Z.8 2.3 I.8 Product of Example 2, % plastein 0.0 .26 .50 i Flavor score 102 118 121 ¦
Mean rank for persistence . 2.50 2.0 1.50 5 i (C) "Corral" chicken flavor paste, % 4.5 3.6 2.7 I! Product of Example 2, % plastein 0.0 0.5 1.1 .
¦¦ F1avor score 116 128 142 ~
i Mean rank for persistence 2.43 1.86 1.71 l :
I (D) "Corral" beef flavor paste, % 4.5 3.6 2.7 .10 ¦i Product of Example 12, % plastein 0.0 0.5 1.1 . ¦
! Flavor score , ~ 112 . 125 132 Mean rank for persistence - 2.50 1. 95 ln55 ¦ (E) 'iCorral'i beef flavor paste, ~ 4 5 ~ 3.6 2.7 l ¦¦ ~ Product of Example 13, % plastein 0.0 1.0 2,0 . ¦ . .
.15 1 - Flavor score : 102 133 150 ! IMean rank for persistence . 2.80 1.80 1.40 1:
, . ' I -: ' '' : .
. I : ~he results of these tests show that products flavored with a combination .
¦ of a "Corral" flavor and a flavoring agent of the present.invention not only ¦
2 1I have an improved~flavor compared with products flavored wlth "Corral" alone, l ~
but also have a greater persistence of flavor on chewing, the degree of per- :
I sistence:increasing with the proportions of flavoring agent according to the. , .
`!~ present invention. It is also apparent ~hat the produc~s of Examples 2 and 12, .
I (derived from supplemented plastein and ribose) have approximately twice the .

`~S 1 flavoring strength (weight fo~ weight) of "Corral" paste ~hile that of .1. :Example 13 tderived from supplemented plastein and glucose) has an approxi- !
.~~, ~ mately~equivalent:flavorlng strength to "CoFral" paste.

Il i . ~1 . . ~ . , .
,:

-... . . ...... .. . ~ . ~. ... .... ~ ... . .

~ 7~ I ~
1, . EX~'L~ 19 ..
jl Defatted ~oya grits (10 pa~ts by wei~ ) were conta~ted with water i (2.5 parts by weight~ contain mg in solution the amounts of "Corral" beef flavor paste or a product of one of Examples 2, 12 or 13 shown in Table II as ~ wt % "Corral" paste or plastein content of product of Examples 2, 12 or 13, ¦¦based on the weight of dry product. The hydrated products were then extruded ¦at 130-140~ and 1000 p.s.i. to form dry., te~tured vegetable protein products .
wbich were then tested for nature and perslstence of flavor.
Results are shown in Table II

10 I TABLE II ~ ¦
,~ .
1................. "'' , ' '' ~' ' 11 . l Flavoring agents . % Flavor of product ~
~1'' ~ . I
. "Corral" beef flavor paste 5.5 soya-like (unflavored) .

'!Corral" beef flàvor paste 11.0 meaty, non-persistent :

Product of Example 2 1.3 meaty, pe}sistent . Product of Example 2 2.6 mea~y, persistent . Product of Example 12 2.6 meaty, persistent Product oE Example 13 5.2 meaty, persistent ' .
,, I .' . . I ~ .

, The resu~t9 show that the beef flavor of tl?e "Corral" paste only . survives the extrusion conditions when a very large amount (117~ of paste is 'incorporated, whereas amounts of flavoring agents according to the present ! invention equivalent to 2.6% or 5.2% "Corral" paste result in flavored exeruded 7- , 1~ , , . ,, ' . ' I

1~ ~ . . .

3C~6 products. Moreover, the latter have a persistent ~lavor on chewing, whereas even the product initially containg 11% "Corral"
paste did not impart a persistent flavor to ~he extruded product on chewing.

The procedure of Example 19 is repeated but the defatted soya grits are extruded at 100 and 3,000 p.s.i., 130 and 300 p.s.i., 150 and 500 p.s.i. and 120,2000 p.s.i.with similæ results.

nhen the procedure of Example l9 is repeated but the defatted soya grits is replaced in each case by defatted saf-flower meal, defatted peanut meal, defatted cottonseed meal, defatted sesame seed meal, a mixture of casein and corn meal con-taining 60% protein, a mixture of microbial protein ~single cell protein available from Exxon)"Exxon" is a Trade Mark~ and wheat flour containlng65% protein or a mixture of fish protein con-centrate and wheat flour containing 45% protein, comparable results are obtained.

Dry, textured soya protein product is re-hydrated (as in Example 18) with aqueous solutions of "Corral" beef flavor paste, alone or with varying amounts of products of Examples 2, 12 or 13 to give flavored products containing the amount of ~lavor shown in Table III, expressed as wt % plastein content based on the weight of the hydrated product.
TABLE III
Flavoring ~ Product Agent of Invention "Corral" beef flavor paste (B) _ 6.0%
(C) Example 2, 1.0% 2.6%
(D) Example 2, 1.2% 3.6%
~E) Example 2, 1.5% 3.6%
~ (F) ~ Example 12, 1.0% 2.6%
(G) Example 13, 2.0% 2.6%

.

~ ''.

~47 _3 Defatted soya grits (10 parts by weight) are contacted with water (2.5 parts by weight) containing in solution a product o~ one o~ Examples 2, 12, or 13, with or without "Corral" beef ~lavor paste, in the amounts sho~n in ~able IV (as wt % based on the weight o~ dry product, as in Example 19).
Ihe hydrated products are then extruded as in Example 19 and re-hydrated with 20 parts by wei~ht o~ water containing in solution 0~5 parts by weight of "Cor-ral" bee~ flavor paste, thereby adding 5% "Corral" beef ~lavor paste (based on the dry weight o~ product) to the flavoring agent or agents already present.
TABXæ I~
Flavorin~ _ __ __ __ __ __ __ __ .~
Product A.~ o~ . _ Example wt ~ dry- wt % wet b % dry* wt % wet (H) 2 1.3 0.~3 _ 1~67 (J) 2 I.3 0.~3 3.3 2-77 (K) 12 1.3 0.~3 3.3 2.77 (L) 13 2.6 0.ô7 3.3 2-77 (M) 2 2.6 o.87 - 1.~67 (~) 12 2.6 0.87 - 1.67 (P) 13 5.2 1.73 - 1.67 (Q) ~ - 1.67 (R) _ 3 40 *added be~ore extrusion ~ter re-hydration, including addibional "Corral"

:: :
: , 19 .:

:~,~73~

For comparison, extruded products (Q) and (R) are also made by ¦ ) ! the same method, but in wllich no flavoring ~gent is added before extrusion and sufficient "Corral" beef f]avor paste is added during re-hydration, to give 1.67% or 3.4% "Corral", respectively, based on the wet weight of the product. i . `' ' il 5 1l Various pairs of the products (A) to (R) of each of Examples 22 Il and 23 have been tested for flavor quality and persistence by panels of judges l by the "triangular" method, i.e. two samples of one product of each pair and one sample of the other product are submit~ed to the members of each panel , and, if one sample is correctly identified as being different from the other 10 ¦¦ two, then a judgement is made either of the quality or of the persistence ! of its ~iavor in comparlson with t~at of the other two.
By this method, it has been found that, for the products of Exam-¦~ ples 22, product (C) has a significantly better quallty beef flavor than i ¦¦ product (A), with similar flavor strength. Products (D) and (E) also have 15 l¦ significantly better quality beef flavors than product (B) with similar ¦ flavor strengths. ;
11 ~oreover, product (D) has a signiEicantly more persistent beef ¦¦ flavor on chewing than product (B). Products (F) and (G) also have goodquality beef flavors, though that of product (C) is significantly better 20 ll than that of product (F) and that of product (F) ls significantly better than that of product (G~.
All the products of ~xample 23 hàve beef ~lavors of good quality and all but products ~Q) and (R) have flavors which are persistent on chewing ¦ It h~s be~n found, however, that products ~U~ and (J) have significantly ~5 l! bet~er quality flavors than produet (Q), while the fIavor of product (J) is I
~ot significantly different from that of product (N), confirming that "Cor- j il ral~ includod in the product before extrusion has ~o effect on the flavor f !
Il , . 1- .
., . ` 11 . . ` ~
1' . . I
20- . , ' : !

-, I

~4~730~ , 1l, the product, aftcr extr~lsion. Products (K) and (L) also have good quality¦¦ beef flavors, though that of product (J) is significantly better than that of j products (K) and (L) which have flavors of similar quality. Products (~) and (P) have significantly better quality and significantly more persistent ',i . I
5 ~I flavors on chewing than product (R). Product (M) has a significantly !`
I b`etter quality flavor than product (P), while that of product (N) is similar to that of product (P).
!-. .
,~ I ~, . . . .

. .,1 . .

il`' '"`` ` ` ` ' ` `: j I . ., ! ~ ` :

, ~ .

-, . ~ ....
,' `

~`: il ` :` . `

Claims (20)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A process for preparing a flavoring agent which com-prises the reaction of a mixture of one part by weight of a hexose or pentose monosaccharide and from about one to ten parts by weight of a plastein supplemented with a sulfur-con-taining amino acid, in an amount of from 5 to 50% by weight based on the supplemented plastein said reaction is carried out by heating said mixture in the presence of water at a tempera-ture in the range of about 80° to 120°C.
2. A process according to claim 1, wherein said hexose or pentose monosaccharide is selected from the group consisting of glucose, ribose and arabinose.
3. A process according to claim 1, wherein the weight ratio of said monosaccharide to said supplemented plastein is from about 1:4 to 1:10.
4. A process according to claim 3, wherein said weight ratio is about 1:10.
5. A process according to claim 1, wherein a flavor modifier is included in the mixture before heating.
6. A process according to claim 5, wherein said flavor modifier is monosodium glutamate.
7. A process according to claim 6, wherein the weight ratio of monosodium glutamate to plastein is from about 1:1 to 1:10.
8. A process according to claim 7, wherein said weight ratio is about 1:5.
9. A process according to claim 1, wherein the amount of said water in the mixture before heating is such as to provide at least about two parts by weight of water for each part of said supplemented plastein.
10. A process according to claim 1, wherein said mono-saccharide is a pentose and the weight ratio of water to sup-plemented plastein before heating is about 5:1.
11. A process according to claim 1, wherein said mono-saccharide is a hexose and the weight ratio of water to sup-plemented plastein is about 20:1.
12. A process according to claim 1, wherein the amount of said sulfur-containing amino acid is from about 15 to 20%
by weight based on the supplemented plastein.
13. A process according to claim 1, wherein said sulfur-containing amino acid used to supplement the plastein is selected from the group consisting of methionine, cysteine, cystine and lanthionine.
14. A process according to claim 13, wherein said sulfur-containing amino acid employed is in the form of a lower alkyl ester, said alkyl having from about one to four carbon atoms.
15. A flavoring agent prepared by the process of claim 1.
16. A meat-flavored textured protein composition com-prising a textured protein having incorporated therein from about 0.1 to 10% by weight based on the dry weight of tex-tured protein, of said flavoring agent of claim 15.
17. A meat-flavored textured protein composition com-prising a textured protein having incorporated therein from about 0.75 to 6% by weight, based on the dry weight of tex-tured protein, of said flavoring agent of claim 15.
18. A meat-flavored textured protein composition according to claim 16, wherein after said flavoring agent is incorporated, the mixture is extruded at a pressure of from about 300-3000 pounds per square inch and at a temperature in the range of about 100 to 150°C.
19. A composition according to claim 16, wherein said protein is vegetable protein.
20. A composition according to claim 19, wherein said vegetable protein is soya protein.
CA219,083A 1974-02-18 1975-01-30 Synthetic meat flavors for texturised vegetable protein Expired CA1047306A (en)

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DK (1) DK57175A (en)
FR (1) FR2260957B3 (en)
GB (1) GB1469331A (en)
IE (1) IE40609B1 (en)
LU (1) LU71861A1 (en)
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US3300402A (en) * 1964-01-09 1967-01-24 Purifax Inc Purification of putrescible unstable wastes
CH670743A5 (en) * 1987-04-06 1989-07-14 Nestle Sa
CH682878A5 (en) * 1991-11-01 1993-12-15 Nestle Sa Method for avoiding the browning of a food product.
GB0319463D0 (en) * 2003-08-20 2003-09-17 Givaudan Sa Compounds
AU2006272595C1 (en) 2005-07-26 2014-08-28 Knauf Insulation Gmbh Binders and materials made therewith
GB0520872D0 (en) * 2005-10-14 2005-11-23 Hofmann Thomas F Onion flavour compounds and use
CN101720341B (en) 2007-01-25 2013-06-12 克瑙夫绝缘私人有限公司 Composite wood
US9828287B2 (en) 2007-01-25 2017-11-28 Knauf Insulation, Inc. Binders and materials made therewith
WO2008127936A2 (en) 2007-04-13 2008-10-23 Knauf Insulation Gmbh Composite maillard-resole binders
GB0715100D0 (en) 2007-08-03 2007-09-12 Knauf Insulation Ltd Binders
WO2011015946A2 (en) 2009-08-07 2011-02-10 Knauf Insulation Molasses binder
KR101835899B1 (en) 2010-05-07 2018-03-07 크나우프 인설레이션, 인크. Carbohydrate binders and materials made therewith
KR101837215B1 (en) 2010-05-07 2018-03-09 크나우프 인설레이션, 인크. Carbohydrate polyamine binders and materials made therewith
GB201214734D0 (en) 2012-08-17 2012-10-03 Knauf Insulation Ltd Wood board and process for its production

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JPS50111265A (en) 1975-09-01
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IE40609B1 (en) 1979-07-04
DK57175A (en) 1975-10-27
GB1469331A (en) 1977-04-06
NL7501741A (en) 1975-08-20
DE2506715C3 (en) 1978-06-29
FR2260957A1 (en) 1975-09-12
BE825417A1 (en)
LU71861A1 (en) 1977-01-05
FR2260957B3 (en) 1977-10-28
IE40609L (en) 1975-08-18
CA1047306A1 (en)
BE825417A (en) 1975-08-11

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