U.S. patent number 3,865,957 [Application Number 05/349,969] was granted by the patent office on 1975-02-11 for low calorie sweetener and sweetener base.
This patent grant is currently assigned to Sueddeutsche Zucker-Aktiengesellschaft. Invention is credited to Ludwig Haberl, Hubert Schieweck, Georg Steinle.
United States Patent |
3,865,957 |
Schieweck , et al. |
February 11, 1975 |
Low calorie sweetener and sweetener base
Abstract
Isomaltitol, which is represented by the formula ##SPC1## 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.
Inventors: |
Schieweck; Hubert (Obrigheim,
DT), Steinle; Georg (Grunstadt, DT),
Haberl; Ludwig (Obrigheim, DT) |
Assignee: |
Sueddeutsche
Zucker-Aktiengesellschaft (Mannheim, DT)
|
Family
ID: |
5841739 |
Appl.
No.: |
05/349,969 |
Filed: |
April 11, 1973 |
Foreign Application Priority Data
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Apr 12, 1972 [DT] |
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2217628 |
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Current U.S.
Class: |
426/548; 426/804;
426/658 |
Current CPC
Class: |
C07H
15/04 (20130101); C07H 15/08 (20130101); A23L
27/34 (20160801); C12P 19/24 (20130101); C12N
9/90 (20130101); Y10S 426/804 (20130101) |
Current International
Class: |
A23L
1/236 (20060101); C12P 19/24 (20060101); C07H
15/08 (20060101); C07H 15/00 (20060101); C07H
15/04 (20060101); C12N 9/90 (20060101); C12P
19/00 (20060101); A23l 001/26 () |
Field of
Search: |
;426/213,217,65,175,190,191,221 ;260/29R ;127/29,30 |
References Cited
[Referenced By]
U.S. Patent Documents
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3705039 |
December 1972 |
Mitsuhashi et al. |
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Other References
wolfrom, M. L., et al., "Isomaltitol," J. Am. Soc. Vol. 74, (1952),
10-62-1064..
|
Primary Examiner: Monacell; A. Louis
Assistant Examiner: Massung; Esther L.
Attorney, Agent or Firm: Armstrong, Nikaido & Wegner
Claims
What is claimed is:
1. 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.
5. 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 99.65:0.35.
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 the addition 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 yeild 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.
Description
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, U.S. 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
##SPC2##
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 U.S. 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 I, 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 80.mu. 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 of a
natural soft drink is obtained.
EXAMPLE VI
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 VII
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 VIII
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 IX
Low calorie sandkuchen are produced in the following manner. 140 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.degree. 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
150.degree. 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 two-thirds 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
Isomaltitol 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 of lactulose. Also,
isomaltitol may be used concerning liver disorders in the place of
insulin as a test substance in renal clearance deteriminations.
* * * * *