GB1572536A - Creation of Inventions and Patents with Artificial Intelligence

GB1572536A – Stabilised l-aspartyl-l-phenylalamine methylester composition
– Google Patents

GB1572536A – Stabilised l-aspartyl-l-phenylalamine methylester composition
– Google Patents
Stabilised l-aspartyl-l-phenylalamine methylester composition

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Publication number
GB1572536A

GB1572536A
GB54334/77A
GB5433477A
GB1572536A
GB 1572536 A
GB1572536 A
GB 1572536A
GB 54334/77 A
GB54334/77 A
GB 54334/77A
GB 5433477 A
GB5433477 A
GB 5433477A
GB 1572536 A
GB1572536 A
GB 1572536A
Authority
GB
United Kingdom
Prior art keywords
apm
composition according
gum
aspartyl
composition
Prior art date
1977-01-24
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
GB54334/77A
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.)

General Foods Corp

Original Assignee
General Foods Corp
Priority date (The priority date 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 date listed.)
1977-01-24
Filing date
1977-12-30
Publication date
1980-07-30

1977-12-30
Application filed by General Foods Corp
filed
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General Foods Corp

1980-07-30
Publication of GB1572536A
publication
Critical
patent/GB1572536A/en

Status
Expired
legal-status
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Classifications

A—HUMAN NECESSITIES

A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES

A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF

A23G4/00—Chewing gum

A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds

A—HUMAN NECESSITIES

A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES

A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF

A23G4/00—Chewing gum

A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds

A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides

A—HUMAN NECESSITIES

A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES

A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF

A23G4/00—Chewing gum

A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products

A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated

Description

PATENT SPECIFICATION ( 11) 1 572 536
CD ( 21) Application No 54334/77 ( 22) Filed 30 Dec 1977 > ( 31) Convention Application No 761836 ( 19) ( 32) Filed 24 Jan 1977 in > ( 33) United States of America (US) ( 44) Complete Specification published 30 July 1980 ( 51) INT CL 3 A 23 L 1/236 B Ol J 13/00 ( 52) Index at acceptance A 2 B 303 309 401 412 503 504 602 660 BB B 8 C A ( 54) STABILISED L-ASPARTYL-L-PHENYLALAMINE METHYLESTER COMPOSITION ( 71) We, GENERAL FOODS CORPORATION, a Delaware, Corporation, of, 250 North Street, White Plains, New York 10625, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly c described in and by the following statement: 5
This invention relates to stabilised L aspartyl L phenylalanine methyl ester compositions.
Chewing gums are generally comprised of a substantially water insoluble, chewable gum base such as chicle Incorporated within this gum base may be plasticizers or softeners to improve the consistency and texture of the gum flavours 10 and sweetening agents such as sugar or corn syrup, or for sugarless gums artificial sweeteners.
L aspartyl L phenylalinine methyl ester (APM) is a dipeptide sweetening agent described in British Patent Specification 1152977 and U S Patent No.
3,492,131 and is a desirable chewing gum sweetening agent Another attribute of 15 APM is that it may be added in effective amounts to a normally sweetened sugar or sugarless chewing gum to produce longer lasting sweetness and flavour as disclosed in U S Patent Nos 3,943,258 and 3,982,023.
In the normal course of manufacture, shipment and storage of chewing gums, the product is often exposed to relatively high temperatures; i e, 700 F to 1000 F 20 plus, for extended periods of time The stability of APM is temperature sensitive.
High temperatures induce the ester linkage to hydrolyze to the dipeptide aspartylphenylaldnine This dipeptide can then cyclize to the corresponding diketopiperazine When this transition takes place, the sweetness of the APM is proportionately lessened Thus, the effectiveness of APM in a chewing gum 25 composition is greatly reduced when the gum is subjected to high thermal storage conditions Therefore, it would be highly desirable if a simple system were devised whereby the decomposition of APM in chewing gum when stored at elevated temperatures could be greatly reduced.
According to the invention there is provided a stabilised L aspartyl L 30 phenylalanine methyl ester composition wherein the L aspartyl L phenylalanine methyl ester is fired with an encapsulating agent (as hereinbefore defined) which is gum Arabic or a reaction product of a compound containing a polyvalent metal ion with an ungelatinized starch acid-ester of a substituted dicarboxylic acid, which starch acid-ester is represented by the formula: 35 R, Starch-O Oc-R-COOH wherein R is dimethylene or trimethylene and R 1 is alkyl, alkenyl, aralkyl or aralkenyl In the food industry reference to encapsulation has come to mean surrounding of particles with a coating in general terms Thus the term “fixed with an encapsulating agent” includes fixing in a continuous matrix 40 Particularly the invention relates to such a composition incorporated into a chewing gum Thus there is specifically provided a sweetened chewing gum composition which comprises gum base, flavour, a bulking agent and L aspartyl L phenylalanine methyl ester (APM) wherein the APM is fixed in an encapsulating agent selected from the group consisting of gum Arabic and a dextrin which is the reaction product of a compound containing a polyvalent metallic ion, with specified ungelatinized starch acid-esters of substituted dicarboxylic acids.
APM is useful in chewing gum as a sweetener and as a sweetness and flavour extender 5 The compositions of the invention generally substantially increase the storage stability of APM when it is combined in the chewing gum confection Heretofore chewing gum containing APM has been found to lose in excess of 70 % of its sweetening potency when stored at 1000 F/30 % rh for 20 weeks The product of the instant invention contains APM which is fixed in gum Arabic and/or dextrin This 10 fixation or encapsulation usually greatly reduces the amount of decomposition of APM in the gum system.
L aspartyl L phenylalanine methyl ester (APM) is a relatively recent development in food technology It is commercially available from G D Searle & Company, Skokie, Illinois, under the trademark name Equa 200 it is a sugar 15 substitute with a sweetening potency approximately two hundred times that of sucrose.
Typical Analysis for Food Grade Equa 200 Identity A Appearance: White Crystalline powder 20 B Odor: Almost odorless (very slight acetic odor) C Taste ( 0 07 % in water): Clean, sweet taste, free of significant bitter, sour, or salty off-notes 25 D Chemical identity tests 1Amino Acid: Positive 2 Ester: Positive E Specific rotation in 15 N formic acid: + 15 91 30 F p H of the 0 8 % solution: 5 32 Assay Titration by Lithium Methoxide: 99 9 % Purity A Clarity and color of solution ( 0.8 % solution): Clear and colorless, no suspended particles B Transmission of solution ( 1 % in 2 N HCI): 99 % at 430 nm C Loss on drying ( 1051 C/4 hours): 3 9 % 40 D Residue on ignition: 0 04 E Heavy metal: 5 ppm F Arsenic: 0 1 ppm G Diketopiperazine: 0 5 % Microbiological 45 A E coli Negative B Salmonella Negative C Coagulase+Staph Negative L aspartyl L phenylalanine methyl ester is a highly desirable replacement for sugar or sucrose in such comestibles as breakfast cereals, dry bases for 50 beverages, gelatin foods, fillings and dairy product analogue toppings However, APM contains an ester linkage that under certain moisture, temperature and p H conditions hydrolyzes to the dipeptide aspartylphenylalanine The dipeptide can then cyclize to the corresponding diketopiperazine (DKP).
A potential for APM to go spontaneously to DKP results in a proportional loss 55 of product sweetness Thus, products which are subjected to extreme heat such as baking are incompatible with APM Further, the products which do incorporate APM will have substantially diminished sweetening potency when adverse conditions such as elevated storage temperatures are encountered.
A chewing gum system is particularly enhanced by incorporating APM within 60 it As a basic sugar substitute, as disclosed in U S Patent No 3,642,491 a sugarless 1,572,536 3 1,572,536 3 chewing gum may be obtained which has a clean sugar-like sweetness and in which no synthetic flavor or after-taste is perceived U S Patent No 3,943,258 teaches that the addition of APM to sugar and sugarless chewing gum compositions in effective amounts extends a time period over which both flavor and sweetness are discernible during chewing According to the practice of the instant invention, the 5 APM may be used as the sole sweetener in a chewing gum composition or added to a sweetened chewing gum as an enhancer or extender.
The gum base may be any chewable, substantially water insoluble base such as chicle and substitutes thereof, guttagkay, sorva, jelutong, synthetic polymers such as polyvinyl acetate, synthetic resins, rubbers and the like and mixtures of these 10 materials The amount of gum base employed may vary widely depending on the type base used and other ingredients making up the final gum product and other like factors Generally, however, it has been found that anywhere from 15 to 40 % by weight of the final gum composition may be used and preferably from about 20 to about 30 % Plasticizers or softeners such as lanolin, propylene glycol, glycerol 15 and the like and mixtures thereof may optionally be incorporated within the gum base to achieve a desired texture and consistency Generally, the flavors employed in chewing gums may be the essential oils or synthetic flavors or mixtures of these.
Flavors such as wintergreen, spearmint, peppermint, birch, anise, fruit flavors, and the like may be used satisfactorily with the variety of gum bases The amount of 20 flavoring material is normally a matter of preference, but may be subject to the consideration of such factors as type of flavor used and the type of base used and the like Generally, flavoring materials account for about 1 % by weight of the total gum composition.
In order to obtain a sweetened gum, the remaining portion of the gum 25 composition is generally a sweetener such as a sugar or for sugarless gums a sugar substitute By sugar is meant sucrose, dextrose, corn syrup solids (their substitutes) and the like and mixtures thereof Sugar substitutes may be any sweetening agent used in sugarless gum such as mannitol, sorbitol, xylitol, saccharin, cyclamate, dihydrochalcone and dipeptides, particularly L aspartyl L phenylalanine 30 methyl ester Sugar and sugar alcohols may also be defined as bulking agents and generally comprise a major amount by weight of the total gum composition.
Additionally, non-sweet bulking agents such as hydrolyzed cereal solids may be included in the gum composition.
The basic concept of the instant invention resides in fixing or encapsulating 35 the APM in order to retard and/or prevent the conversion of APM to DKP under certain moisture, temperature and p H conditions which affect a chewing gum system It has been found that APM may be successfully fixed in gum Arabic and a particular dextrin which is commercially available under the registered trademark name Capsul as manufactured by National Starch and Chemical Corporation, 40 New York, New York.
Physical Properties:
Color White to off-white Form Powder p H 3 (approx) 45 Moisture 5 % (approx) Capsul dextrin, as disclosed in U S Patent No 3,091,567, is a reaction product of a compound containing a polyvalent metallic ion, with an ungelatinized starch acid-ester of a substituted dicarboxylic acid Such starch acidesters may be represented diagrammatically by the following formula: 50 R, Starch-OOC-R-COOH where R is a radical selected from the class consisting of dimethylene and trimethylene radicals, and R 1 is a hydrocarbon constituent selected from the class consisting of alkyl, alkenyl, aralkyl or aralkenyl groups The abovedescribed ungelatinized starch acid-esters are prepared by reacting an ungelatinized starch, in 55 an alkaline medium, with a substituted cyclic dicarboxylic acid anhydride having the following formula:
Trademark 1,572,536 0 wherein R and R 1 are as defined above Substituted cyclic dicarboxylic anhydrides falling within this formula are the substituted succinic and glutaric acid anhydrides.
In the preferred embodiment of this invention, the APM fixation is accomplished by spray drying prior to incorporating it into the chewing gums 5 Other methods such as coacervation may be employed The spray drying process comprises forming an emulsion of APM and the gum Arabic or dextrin in a continuous aqueous solution The emulsion is then passed through a spray nozzle and broken up into numerous droplets The droplets are introduced into a drying environment and as their moisture is given up the droplets are formed into solid 10 particles The APM now exists as part of the solid matrix which is to be incorporated in a chewing gum formulation.
In the preferred embodiment of the instant invention, an aqueous solution of APM and an encapsulating agent are passed through a positive displacement homogenizer at pressures between 250 psi and 500 psi and preferably 1500 psi to 15 2500 psi so that the components are thoroughly mixed and/or emulsified Next, it is most preferable to introduce the product stream into the body of the spray dryer via a rotating disc-type nozzle The product stream contacts the disc which may be rotated by separate means or by the pressure of the product stream and thereby the product stream is dispersed into numerous droplets within the spray dryer The 20 rotating disc allows a more uniform product distribution of the material to be spray dried within the tower.
The temperatures employed in the drying process are typically in an air temperature range of 3501 F to 5501 F on the inlet side and 1750 F to 300 ‘F on the outlet side Preferably the inlet temperature is between 375 OF and 425 OF and the 25 outlet temperature is between 200 OF and 2500 F The temperature of the solution entering the dryer is preferably between 600 F and 120 ‘F and most preferably between 700 F and 90 F The dispersion wheel or rotating disc may operate between about 200 rpm and 1000 rpm and preferably between 550 rpm and 850 rpm The concentration of solids entering the dryer may be between 10 % to 45 % 30 solids by weight Preferably the total solids concentration will be between 20 % and % by weight.
The ratio of encapsulating agent to APM may vary between about 10:1 to about 2:1 and most preferably will be between 5:1 to 3:1 The ratio of encapsulating agent to APM of the final product will be the same as the ratios comprising the inlet 35 stream since substantially all of the water is removed during drying.
Example I
Peppermint Flavor Chewing Gum Sucrose/Dextrose Formulation % Control APM in APM in 40 Ingredient Free APM Gum Arabic Capsul Chewing Gum Base 24 000 24 000 24 000 Sugar, 6 x 29 197 28 097 28 097 Dextrose Monohydrate 29 000 27 500 27 500 Corn Syrup, 45 5 Baume 15 000 15 000 15 000 45 Glycerol 0 800 0 800 0 800 Lecithin 0 200 0 200 0 200 APM 0 650 Peppermint Oil+Enhancer 1 153 1 153 1 153 20 % APM Fixed in Gum Arabic 3 250 50 % APM Fixed in Capsul Dextrin 3 250 000 100 000 100 000 Trademark 1,572,536 5 Example I (cont’d) Co-Drying of APM Dryer diameter: 12 feet Total height: 30 feet Vertical drying height: 14 feet (which is the distance between the nozzle and 5 the top of the cone-shaped lower section of the spray dryer).
Gum Arabic A solution comprising 240 pounds of gum Arabic, 60 pounds of APM and 110 gallons of water is prepared The solution is passed through a MantinGalin positive displacement homogenizer at an operating pressure of 2000 psi The 10 product stream is fed to the spray dryer via a rotating disc nozzle The disc is rotated at 800 rpm The average inlet temperature is 410 F and the outlet temperature is 215 F Feed temperature of the solution is 78 F.
Capsul The Capsul is co-dried under the same conditions as the Gum Arabic 15 Preparation of Sugar APM Chewing Gum 2000 Gram Batch in I Gallon Sigma Mixer 1 Soften gum base in a steam-jacketed sigma-blade mixer at 120-130 F for five minutes.
2 Add the glycerine and lecithin and mix five minutes 20 3 Add corn syrup, mix five minutes.
4 Add 1/2 the sucrose/dextrose mixture, mix thoroughly.
Add remaining sucrose/dextrose blended with APM or fixed APM, mix thoroughly.
6 Add flavor, mix for two minutes 25 7 Pass the gum through sheeting rolls at approximately 100 O F, to a thickness of 0 068-0 075 “.
8 Temper the sheets at 70 F/45 % RH for 24 hours, score into sticks and package.
Effect of Fixation on APM Stability 30 Sucrose/Dextrose Peppermint Formulations % APM Loss at 100 F Sample # Description 4 wks 9 wks 17 wks 20 wks
1 Control-Free APM 23 38 73 2 APM fixed in Gum Arabic 5 12 40 35 3 APM fixed in Capsul Dextrin 0 16 50 Example II
Peppermint Flavor Chewing Gum Sugarless Formulations % APM in 40 Control APM in Capsul Ingredient Free APM Gum Arabic Dextrin Chewing Gum Base 27 000 27 000 27 000 Sorbitol 47 174 44 574 44 574 Sorbo Solution ( 70 %) 17 300 17 300 17 300 45 Mannitol 6 100 6 100 6 100 Glycerol 0 500 0 500 0 500 Peppermint Oil+Enhancer 1 276 1 276 1 276 APM 0 650 20 % APM in Gum Arabic 3 250 50 % APM in Capsul Dextrin 3 250 000 100 000 100 000 Co-drying of Gum Arabic and Capsul same as Example I.
Trademark Example II (cont’d) Sugarless APM Chewing Gum Process Procedure for 1,750 Gram Batch in 1 Gallon Sigma Mixer 1 Preheat mixer to 150 OF with mixture of steam and water It may be necessary to soften base in mixer, or before adding to mixer, to get proper 5 mixing.
2 Add base and glycerol, mix 5-10 minutes.
3 Add 1/2 of sorbitol and mannitol, blend for 5-10 minutes.
4 Add sorbo solution and mix until uniform (approx 5 minutes).
5 Preblend APM or fixed APM and remaining sorbitol and mannitol, and 10 add to mixer Shut off steam, allow cold water to circulate in jacket Mix 5 minutes.
6 Check mix for grainyness If grainy, mix for additional 5-10 minutes.
7 Add flavor, mix 2-3 minutes.
8 Remove from mixer, pass the gum through sheeting rolls at approximately 15 1000 F to a thickness of 0 68-0 075.
9 Temper the sheets at 700 F/45 % RH for 24 hours, score into sticks and package.
Effect of Fixation on APM Stability Sugarless Peppermint Formulations 20 % APM Loss at 100 IF.
Sample # Description 4 wks 9 wks 20 wks
4 Control-Free APM 22 33 64 APM Fixed in Gum Arabic 17 22 43 6 APM Fixed in Capsul dextrin 21 32 54 25 We are aware of the Artificial Sweeteners in Food Regulations ( 1969) (Sl 1817) and nothing contained herein should be construed as an instruction to breach said regulations nor do we make any claim to use of the invention in contravention of the law.
The Comptroller considers that the invention described in this specification 30

Claims (9)

cannot be performed without substantial risk of infringement of Claim I
of the specification of Patent No 1,152,977.
WHAT WE CLAIM IS:1 A stabilised L aspartyl L phenylalanine methyl ester composition wherein the L aspartyl L phenylalanine methyl ester is fixed with an 35 encapsulating agent (as hereinbefore defined) which is gum Arabic or a reaction production of a compound containing a polyvalent metal ion with an ungelatinized starch acid-ester of a substituted dicarboxylic acid, which starch acidester is represented by the formula:
R, Starch-OOC-R-COOH 40 wherein R is dimethylene or trimethylene and R 1 is alkyl, alkenyl, aralkyl or aralkenyl.

2 A composition according to Claim I wherein the weight ratio of methyl ester to encapsulating agent is from 10:1 to 2:1.

3 A composition according to Claim 1 wherein the weight ratio is from 5:1 to 45 3:1.

4 A composition according to any one of Claims 1 to 3 wherein the encapsulation has been effected by co-drying an aqueous emulsion of the ester and encapsulating agent.

5 A composition according to claim I wherein the co-drying has been effected 50 by spray-drying the emulsion.

6 A composition according to any one of claims 1 to 5 whenever incorporated into a chewing gum comprising gum base, flavour and a bulking agent.

7 A composition according to Claim 6 wherein the bulking agent is a sugar.
Trademark 1,572,536 7 1,572,536 7

8 A composition according to Claim 6 wherein the bulking agent is a sugar alcohol which is sorbitol, mannitol, xylitol or a mixture thereof.

9 A stabilised composition containing L aspartyl L phenylalanine methyl ester substantially as hereinbefore specifically described.
LANGNER PARRY, Chartered Patent Agents, High Holborn House, 52-54 High Holborn, London, WCIV 6 RR.
Agents for the Applicants.
Printed for Her Majesty’s Stationery Office, by the Courier Press, Leamington Spa 1980 Published by The Patent Office, 25 Southampton Buildings, London WC 2 A l AY from which copies may be obtained.

GB54334/77A
1977-01-24
1977-12-30
Stabilised l-aspartyl-l-phenylalamine methylester composition

Expired

GB1572536A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US05/761,836

US4122195A
(en)

1977-01-24
1977-01-24
Fixation of APM in chewing gum

Publications (1)

Publication Number
Publication Date

GB1572536A
true

GB1572536A
(en)

1980-07-30

Family
ID=25063377
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB54334/77A
Expired

GB1572536A
(en)

1977-01-24
1977-12-30
Stabilised l-aspartyl-l-phenylalamine methylester composition

Country Status (12)

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US
(2)

US4122195A
(en)

JP
(1)

JPS5934106B2
(en)

AU
(1)

AU511732B2
(en)

BE
(1)

BE863138A
(en)

CA
(1)

CA1099574A
(en)

CH
(1)

CH628212A5
(en)

DE
(1)

DE2800202C2
(en)

FR
(1)

FR2377770A1
(en)

GB
(1)

GB1572536A
(en)

IT
(1)

IT1102814B
(en)

NL
(1)

NL188781C
(en)

SE
(1)

SE7714919L
(en)

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Assignee
Title

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1996-03-14
1999-09-14
Wm. Wrigley Jr. Company
Chewing gum containing gum talha

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IT
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active

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JP
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Also Published As

Publication number
Publication date

DE2800202A1
(en)

1978-07-27

US4139639A
(en)

1979-02-13

IT7847742D0
(en)

1978-01-23

NL7800596A
(en)

1978-07-26

CH628212A5
(en)

1982-02-26

NL188781B
(en)

1992-05-06

NL188781C
(en)

1992-10-01

JPS53101571A
(en)

1978-09-05

FR2377770B1
(en)

1980-08-22

FR2377770A1
(en)

1978-08-18

US4122195A
(en)

1978-10-24

AU3285178A
(en)

1979-08-09

BE863138A
(en)

1978-05-16

CA1099574A
(en)

1981-04-21

SE7714919L
(en)

1978-07-25

AU511732B2
(en)

1980-09-04

IT1102814B
(en)

1985-10-07

DE2800202C2
(en)

1986-09-25

JPS5934106B2
(en)

1984-08-20

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