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Publication numberUS3865957 A
Publication typeGrant
Publication dateFeb 11, 1975
Filing dateApr 11, 1973
Priority dateApr 12, 1972
Also published asDE2217628B1, DE2217628C2
Publication numberUS 3865957 A, US 3865957A, US-A-3865957, US3865957 A, US3865957A
InventorsHubert Schieweck, Georg Steinle, Ludwig Haberl
Original AssigneeSueddeutsche Zucker Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Low calorie sweetener and sweetener base
US 3865957 A
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Description  (OCR text may contain errors)

United States Patent 1 1 Schieweck et al.

[451 Feb.-11, 1975 LOW CALORIE SWEETENER AND SWEETENER BASE [75] Inventors: Hubert Schieweck, Obrigheim;

Georg Steinle, Grunstadt; Ludwig Haberl, Obrigheim, all of Germany [73] Assignee: Sueddeutsche Zucker-Aktiengesellschaft, Mannheim, Germany 221 Filed: Apr. 11, 1973 21 Appl. No.: 349,969

[30] Foreign Application Priority Data Apr. 12, 1972 Germany 2217628 [52] US. Cl 426/213, 426/217, 426/380 [51] Int. Cl A231 l/26 [58] Field of Search 426/213, 217, 65, 175,

[56] References Cited UNITED STATES PATENTS 12/1972 Mitsuhashi et al 426/190 X OTHER PUBLICATIONS Wolfrom, M. L., et al., Isomaltitol, J. Am. Chem.

Soc. Vol. 74, (1952) 10-62-1064.

Primary ExaminerA. Louis Monacell Assistant Examiner-Esther L. Massung Attorney, Agent, or FirmArmstrong, Nikaido & Wegner [57] ABSTRACT lsomaltitol, which is represented by the formula has been discovered to be a highly suitable sweetening agent for human consumption, either alone or with other sweet carbohydrates, or as a base for use with other sweeteners such as the methyl ester of L-aspartyl-L-phenylalanine.

13 Claims, N0 Drawings LOW CALORIE SWEETENER AND SWEETENER BASE BACKGROUND OF THE INVENTION In recent years there has been an ever increasing consciousness of the need for good health, and particularly for conscientious weight control. However, in part due to the increasingly urban life of most people, it has become difficult for many to maintain a proper weight control program. Accordingly, many have come to rely upon sugar substitutes as one means of controlling weight problems. During the sixties it was thought that an ideal solution had been achieved through the widespread use of cyclamates, both for beverages as well as in foodstuffs. However, due to the potential dangers of side effects, this sugar substitute, once thought by many the ideal solution for a low calorie sweetener, now has been generally withdrawn from the world as a sugar substitute. Accordingly, and in particular with the increased reliance upon sugar substitutes generated by the widespread use of cyclamates, the need for an ideal sugar substitute has become even greater than the period prior to the introduction of cyclamates. Various sugar substitutes have been proposed in recent years, some with the potential of being suitable as the ideal substitute for sugar. Schlatter, US. Pat. No. 3,492,131, describes a synthetic sweetener which is a lower alkyl ester of L-aspartyl-L-phenylalanine. Schlatter describes this sweetener as being of a remarkably greater potency than sucrose. The sweetness of an aqueous solution of L-aspartyl-L-phenylalanine (methyl ester) is described as being detected in a concentration between 0.5 to 1.0 percent as compared to sucrose. It is, therefore, 100-200 times as sweet as sucrose. One of the difficulties generated by such a powerful sweetening agent is that it is difficult to use with such a high degree of sweetening power. Other research efforts in the field of sweeteners is reported in German Auslegeschrift No. 1,903,075 and British patent specification No. 1,253,300 which respectively report on maltitol and lactitol, both of which are reported to be low in calories and therefore useful for dietary purposes. These substances suffer from the drawback that they are used in the practical sense exclusively in the syrup form, although the chemical literature reports the crystalization of maltitol and lactitol, respectively, in Karrer et al., Reduktionsproduckte von Disacchariden: Maltit, Lactit, Cellobit, Helv. Chem. Acta., Vol. 20, pages 86-90 (1937), and K. R. Brown et al., Crystalline Lactositol in J. American Chem. Soc., Vol. 60, pages 571-573 (1958). Efforts have been made to duplicate the results of Karrer et al., and Brown et al., to produce crystalline maltitol and lactitol. It has been found, however, that the crystalline form can be obtained only with difficulty from an ethanolic solution.

SUMMARY OF THE INVENTION In accordance with the invention, we have discovered a new sweetening composition which avoids the drawbacks mentioned above, particularly being suitable as a low calorie synthetic sweetener useable as a solid form in the manner of sugar, either alone or in combination with other sweeteners such as the methyl ester of L-aspartyl-L-phenylalanine. The new sweetener composition of the invention is based upon isomaltitol which has the formula In contrast to the problems of producing a crystalline form of maltitol and lactitol, it has been found that crystalline isomaltitol can be readily crystallized from an aqueous solution. As the product is for human consumption, the purity of the product is important from a standpoint of health, and is also important from a standpoint of marketability pure white crystals being the only form which would simulate the appearance of natural sugar. The ready crystallization of isomaltitol from water therefore makes it possible to economically produce a low calorie sweetener having the appearance of sugar. Isomaltitol is low in calories and therefore finds many applications in the dietary field as a sugar substitute and sweetener, as well as being particularly suited as the base for compatible artificial sweeteners such as the methyl ester of L-aspartyl-L-phenylalanine. By varying the proportions of the isomaltitol and the artificial sweeteners in the mixture, varying degrees of sweetness can be achieved; in particular, it is possible to provide mixtures which duplicate the degree of sweetness of natural sugar. The practical advantage of providing such a mixture is seen from the fact that the consumer is able to use the mixture in the same manner as natural sugar, for example, substituting a like amount of the sugar substitute for natural sugar in every day recipes. In commercial production of foodstuffs and beverages it is possible to convert production of a normal foodstuff to a dietetic foodstuff by merely substituting the sugar substitute of the invention for sugar, without adjusting the various ratios of other components.

A particularly advantageous sugar substitute in accordance with the invention comprises the methyl ester of L-aspartyl-L-phenylalanine and isomaltitol in a weight ratio of 0.35:99.65. This mixture may be used in the normal manner that crystalline sugar is used, owing to the advantage of a substantially identical degree of sweetness per unit weight, and due to the facile crystallization of the isomaltitol from aqueous medium. It may be used in the crystalline form for bulk commercial use or household food preparation. In one preferred aspect of the invention, the mixture is compressed into tablets having a weight of from 3 to about 6 grams.

For the industrial or household manufacture of foodstuffs and beverages the mixture of isomaltitol and other synthetic sweeteners can be either in the solid or liquid form or directly substituted for sugar where no further heating of the foodstuff or beverage is required after addition of the sugar substitute, such as, for example, in the preparation of soft drinks and other cold beverages. Where a heating process is required in the preparation of foodstuffs and beverages, it is desirable to add the isomaltitol after the heating stage, for example, in the preparation of chocolates, sweets, jams and jellies, and ice cream.

The following examples serve to further illustrate the invention:

The preparation of isomaltitol may be accomplished in the manner set forth in the US. patent application, Ser. No. 349,974, of the same inventors herein, entitled ISOMALTITOL PRODUCTION FROM SUCROSE, and filed on even date herewith. Alternatively, the isomaltitol may be produced in accordance with the procedure set forth in German Pat. No. 1,049,800.

The following examples are provided merely for the purpose of illustration, and are not to be construed as limitive, reference being had to the claimed appended hereto for that purpose. The portions are by weight unless otherwise indicated.

EXAMPLE I A mixture of 99.88 parts isomaltitol and 0.14 parts saccharin (sodium salt of o-benzoic acid sulfimide) was prepared and determined by comparison with nautral sugar to be of the same level sweetness per unit weight.

EXAMPLE II In the case of aqueous solutions of the mixture of Example l, the taste characteristics vary from the same degree of concentration of saccharin solutions; however, in concentrations of greater than 9 percent there is no statistically observable difference in the taste characteristics which can be observed.

EXAMPLE III A mixture of 98.0 parts isomaltitol and 2.0 parts cyclamate (the sodium salt of the cyclohexylsulfonic acid) was determined through experimentation with various mixtures to be of the identical sweetness level of natural sugar, although in their taste characteristics as compared with the same concentration of saccharose solutions there is a variance based upon the concentration of the aqueous solution tested.

EXAMPLE IV A low calorie sweet chocolate was prepared through the incorporation of isomaltitol in place of natural sugar. To prepare, isomaltitol-sweetened chocolate, the following recipe may be used. 25 kg. of isomaltitol, which has first been prepared as a fine powder having a size less than 80y. is mixed with 22.5 kg bulk cocoa and 2.5 kg cocoa-butter with the addition of lecithin and vanilla being also added into the mixture in the usual manner, followed by the usual grinding and mixing. Shortly before the final preparation of the chocolate, there is added to the chocolate mass 88 g of the methyl ester of L-aspartyl-L-phenylalanine. The resultant mixture containing the methyl ester of L-aspartyl- L-phenylalanine is vigorously mixed to obtain a uniform product. The resultant product is an excellent sweet chocolate having the taste and texture of sweet chocolate which is prepared with sugar, differing in having a lower caloric content than the natural sweet chocolate.

EXAMPLE V An orange soft drink is prepared by adding 8.9 kg of the mixture of Example 1 with 12.63 of orange soft drink base. This mixture is dissolved in 78.47 kg water and carbonated in the usual manner with 7 g/l carbon dioxide. An orange soft drink having the taste ofa natural soft drink is obtained.

EXAMPLE Vl By substituting soft drink base of cherry, lime or grape, otherwise following the process of Example V, low calorie cherry soda, lime soda and grape soda can be obtained which have the taste of natural sugar.

EXAMPLE Vll In order to modify a cola such as Coca-Cola to a low calorie cola, 10.95 kg of mixture of Example I is added to 0.66 kg of the cola base, which is then dissolved in 88.39 kg water. Carbon dioxide is added to carbonate to the same degree as described in the manufacture of orange soda in Example V.

EXAMPLE Vlll In order to produce a low calorie ice cream, the following procedure is followed. 22.1 kg of sweet cream having a 40 percent fat content, 58.1 kg whole milk having a 3.7 percent fat content and 4.5 kg skimmed milk powder, together with 0.3 kg stabilizer are mixed with 15 kg isomaltitol, and thereafter homogenized and sterilized in the usual manner. After the sterilization process has been completed, 53 g of fine, powdered methyl ester of L-aspartyl-L-phenylalanine is added to the ice cream mass, followed by vigorous stirring, beating and freezing. The resultant ice cream has the taste and texture of the normally produced higher caloric ice cream utilizing sugar, and particularly has the same degree of sweetness.

EXAMPLE lX Low calorie sandkuchen are produced in the following manner. g butter is mixed with 140 g of crystalline isomaltitol and four egg yolks, and stirred together to make a foamy mass. Thereto is added 140 g flour together with baking powder and finally there is added the whites of four eggs. The mixture is folded and blended in the usual manner, followed by baking at a temperature of 160 C for a period of about 45 minutes. The sandkuchen which are produced appear completely normal in terms of texture, such as the pore size and browning characteristics. The taste of the sandkuchen prepared in accordance with the above procedure was compared with sandkuchen made from sugar, and the same degree of sweetness of the sandkuchen was observed.

EXAMPLE X Low calorie strawberry marmalade are prepared from strawberries which have been mashed in the usual manner for preparation of strawberry marmalade. 1 kg of the thus mashed strawberries is added to 1 kg of crystalline isomaltitol and 8 g of a pectin having SAG-USA as well as 7 g tartaric acid. The mixture is boiled for 3 minutes and then filled directly into the usual glasses.

The dried substance at the end of the boiling was 61.5 percent. The gelatinization of the maramalade proceeded without objection. The low calorie strawberry marmalade of the invention was compared for taste qualities with the identical marmalade made with sugar instead of isomaltitol, with the same results being observed for sweetness and other properties.

EXAMPLE XI To baby food of the usual composition, or to twothirds milk one provides 100 kCal nourishment value. Added to this unit value is 2 g. isomaltitol. The isomaltitol, while providing a sweetening effect, is particularly suited for such baby food as it for the most part accumulates in the large colon, providing for the advantageous nourishment of the infants and small children.

EXAMPLE XII lsomaltitol is also complementary with naturally sweet tasting, nourishing carbohydrate substances, and can be used in admixture with such carbohydrates to bring their sweetness level close to sugar. As examples of such carbohydrates may be mentioned fructose, xylitol, and sorbitol.

To prepare a foodstuff approximating the sweetness of sugar which is particularly suitable for diabetics who must restrict their intake of sugar, a 1:1 mixture of fructose and isomaltitol is prepared.

EXAMPLE XIII Due to the fact that the isomaltitol is largely retained in the large colon, foodstuffs containing isomaltitol, or isomaltitol used in admixture with other constipation aids, may be used in the treatment of chronic constipation in place oflactulose. Also, isomaltitol may be used concerning liver disorders in the place of insulin as a test substance in renal clearance deteriminations.

What is claimed is:

l. A foodstuff or beverage containing a low calorie sweetener agent approximating the taste of natural sugar for human consumption and providing said beverage or foodstuff with a taste normally obtained through pure sugar, said low calorie sweetening agent comprising finely divided, crystalline isomaltitol as the major component, and said sweetener having a degree of purity rendering it suitable in taste, appearance and quality for human consumption.

2. A sweetener agent which comprises isomaltitol and a synthetic sweetener composition.

3. A sweetener agent of claim 2 wherein said synthetic sweetener component is the methyl ester of L-aspartyl-L-phenylalanine.

4. A sweetener agent of claim 2 wherein said synthetic sweetener component is saccharin.

S. A synthetic sweetener of claim 3, wherein isomaltitol comprises at least 98 percent by weight of the mixture.

6. A synthetic sweetener of claim 5, wherein the weight ratio of isomaltitol to the methyl ester of L-aspartyl-L-phenylalanine is about 99.651035.

7. In a sweetened foodstuff wherein the sweet taste is normally derived from sugar, the improvement whereby at least some of the sugar normally present in said sweetened foodstuff is replaced by at least a portion of the sweetener of claim 6, whereby a product of comparable food qualities is provided except for the provision of a lower caloric content.

8. In a sweetened beverage wherein the sweet taste is normally derived from sugar, the improvement whereby at least some of the sugar normally present in said sweetened beverage is replaced by at least a portion of the sweetener of claim 6, whereby a product of comparable food qualities is provided except for the provision of a lower caloric content.

9. In the process of providing a sweetened foodstuff or beverage via theaddition of a sweetener, the improvement which comprises incorporating the sweetener of claim 6, whereby the resultant product has a high quality appearance and taste with a lower caloric content.

10. A sweetened food composition which comprises a naturally sweet carbohydrate foodstuff and isomaltitol, said isomaltitol being present in an amount to yield a food composition having the approximate sweetness of sugar.

11. A sweetened food composition of claim 10 wherein said naturally sweet carbohydrate is fructose. 12. A sweetened food composition of claim 11 wherein fructose and isomaltitol are present in approximately a 1:1 weight ratio.

13. A method of providing a dietary foodstuff particularly suitable for diabetics which comprises admixing isomaltitol with a naturally sweet carbohydrate.

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U.S. Classification426/548, 426/658, 426/804
International ClassificationC12N9/90, C12P19/12, C13K7/00, A23L1/236, C07H15/08, C07H15/04, C12R1/01, C12R1/425, C12P19/24, C12P19/44
Cooperative ClassificationY10S426/804, A23L1/2364, C07H15/04, C07H15/08, C12P19/24, C12N9/90
European ClassificationC07H15/08, C07H15/04, A23L1/236D2, C12N9/90, C12P19/24