Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/33—Artificial sweetening agents containing sugars or derivatives
  • A23L27/34—Sugar alcohols
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
  • C07H15/08—Polyoxyalkylene derivatives
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
  • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
  • C12N9/90—Isomerases (5.)
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
  • C12P19/00—Preparation of compounds containing saccharide radicals
  • C12P19/24—Preparation of compounds containing saccharide radicals produced by the action of an isomerase, e.g. fructose
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S426/00—Food or edible material: processes, compositions, and products
  • Y10S426/804—Low calorie, low sodium or hypoallergic

Definitions

• 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.
• 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.
• 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.
• 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.
• the mixture is compressed into tablets having a weight of from 3 to about 6 grams.
• 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.
• the isomaltitol after the heating stage, for example, in the preparation of chocolates, sweets, jams and jellies, and ice cream.
• 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.
• isomaltitol may be produced in accordance with the procedure set forth in German Pat. No. 1,049,800.
• 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.
• 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.
• carbohydrates may be mentioned fructose, xylitol, and sorbitol.
• 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.
• a sweetener agent which comprises isomaltitol and a synthetic sweetener composition.
• 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.
• a sweetened food composition of claim 10 wherein said naturally sweet carbohydrate is fructose.
• a method of providing a dietary foodstuff particularly suitable for diabetics which comprises admixing isomaltitol with a naturally sweet carbohydrate.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Health & Medical Sciences (AREA)
• Genetics & Genomics (AREA)
• Biochemistry (AREA)
• Biotechnology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Molecular Biology (AREA)
• Bioinformatics & Cheminformatics (AREA)
• General Engineering & Computer Science (AREA)
• Microbiology (AREA)
• Crystallography & Structural Chemistry (AREA)
• Proteomics, Peptides & Aminoacids (AREA)
• Biomedical Technology (AREA)
• Food Science & Technology (AREA)
• Polymers & Plastics (AREA)
• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Nutrition Science (AREA)
• Seasonings (AREA)
• Preparation Of Compounds By Using Micro-Organisms (AREA)
• Tires In General (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Preventing Corrosion Or Incrustation Of Metals (AREA)
• Saccharide Compounds (AREA)
• Coloring Foods And Improving Nutritive Qualities (AREA)
• Confectionery (AREA)

Applications Claiming Priority (1)

Publications (1)

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Cited By (35)

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Citations (1)

• 1972
  • 1972-04-12 DE DE2217628A patent/DE2217628C2/de not_active Expired
• 1973
  • 1973-03-27 GB GB1478673A patent/GB1429334A/en not_active Expired
  • 1973-03-28 BE BE129378A patent/BE797458A/xx not_active IP Right Cessation
  • 1973-03-29 AT AT274873A patent/AT330204B/de not_active IP Right Cessation
  • 1973-04-03 FI FI731018A patent/FI51714C/fi active
  • 1973-04-11 US US349969A patent/US3865957A/en not_active Expired - Lifetime
  • 1973-04-12 BR BR732665A patent/BR7302665D0/pt unknown
  • 1973-04-12 SU SU7301906951A patent/SU578900A3/ru active
• 1974
  • 1974-01-11 SU SU7401987824A patent/SU571240A1/ru active
• 1979
  • 1979-10-26 JP JP13788379A patent/JPS55108271A/ja active Granted

Patent Citations (1)

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