WO2005020716A1 - Solution d'aspartame - Google Patents

Solution d'aspartame Download PDF

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Publication number
WO2005020716A1
WO2005020716A1 PCT/CH2003/000587 CH0300587W WO2005020716A1 WO 2005020716 A1 WO2005020716 A1 WO 2005020716A1 CH 0300587 W CH0300587 W CH 0300587W WO 2005020716 A1 WO2005020716 A1 WO 2005020716A1
Authority
WO
WIPO (PCT)
Prior art keywords
aspartame
solution
cyclodextrin
beta
anyone
Prior art date
Application number
PCT/CH2003/000587
Other languages
English (en)
Inventor
Harald Meyer
Original Assignee
Ajinomoto Switzerland Ag
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.)
Filing date
Publication date
Application filed by Ajinomoto Switzerland Ag filed Critical Ajinomoto Switzerland Ag
Priority to CNA038270056A priority Critical patent/CN1826057A/zh
Priority to EP03818371A priority patent/EP1657983A1/fr
Priority to AU2003250732A priority patent/AU2003250732A1/en
Priority to PCT/CH2003/000587 priority patent/WO2005020716A1/fr
Publication of WO2005020716A1 publication Critical patent/WO2005020716A1/fr

Links

Classifications

    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners
    • 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
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention concerns an aspartame solution, in particular a highly concentrated aqueous as- parta e solution and uses thereof.
  • Aspartame is a high potential sweetener that for its sugar-like taste is broadly applied to sweeten food stuffs.
  • One disadvantage of aspartame is its low solubility in water of only about 1%.
  • Cyclodextrins are known to act as solubility enhancers for several substances . The solubility enhancing effect is due to the formation of a 1:1 complex. Therefore, over the past years cyclodextrin derivatives, in particular specificly substituted cyclodextrins, have been developed that have enhanced solubility.
  • Unfortunately such highly soluble cyclodextrin derivatives are not approved for use in foodstuffs. Thus, for foodstuff applications only the natural cyclodextrins may be used.
  • a general object of the present invention to provide a high-concentrated aqueous aspar- tame solution suitable for foodstuff applications .
  • Other objects of the present invention are - a method for producing an aqueous aspartame solution of the present invention, - the use of beta-cyclodextrin to produce an aqueous aspartame solution of the present invention, - the use of an aspartame solution of the present invention for improving the taste of beverages, in particular milk, - the use of an aspartame solution of the present invention in the production of fermented or not fermented milk products, - a beverage or foodstuff, in particular a milk derived beverage or foodstuff, comprising an aspartame solution of the present invention, - an aseptic bag comprising a solution of the present invention and its use in a liquid dosing and mixing apparatus .
  • the aqueous aspartame solution of the present invention is manifested by the features that it comprises aspartame and beta- cyclodextrin . It has surprisingly been found that aspartame and beta-cyclodextrin have a synergistic effect resulting in highly concentrated stable solutions comprising about 15 - 17 % beta-cyclodextrin and about 5 % aspartame. In view of the synergistic effect, in a concentration range above the solubility of the single com- pounds, equimolar amounts should be used to ensure that no undissolved substances remain in the solution.
  • sterilization can simultaneously serve as sterilization.
  • Another possibility to get sterilization is e.g. by pasteurization, in particular by heating the solution at a pH in the range of about 4.2 to 4.5, since in said pH-range the aspartame degradation is slowest.
  • the production of the solution can be performed either at ambient temperature or at enhanced temperature. Enhanced temperature does not much reduce the time needed to get a solution, since stirring over a long time (up to 24 hours) is in any case preferred in order to ensure complete formation of the 1 : 1 complex.
  • Suitable stirring methods are in particular mechanical stirring. The stirring intensity seems not to be critical. E.g. soft stirring (50 to 200 rpm) , in particular around 150 rpm, proved to be suitable.
  • the stirring usually is performed until full dissolution (complex formation) is obtained.
  • Presently preferred dissolution parameters are stirring for a short time, e.g. 10 to 20 min., in particular about 15 min. , at enhanced temperature of usually about 45°C to 55°C, in particular approx. 50°C, followed by stirring for up to about and often about 24 hours at low temperature of usually about 20 to 30°C, in particular at ambient temperature.
  • the aspartame and/or the beta-cyclodextrin can be mixed as solids and the resulting mixture can be added to water or, preferably the water to the mixture.
  • the aspartame and/or the beta-cyclodextrin can be suspended in part or all of the water and then mixed in the adequate ratio.
  • the actual procedure chosen, however, should ensure that the cyclodextrin and the aspartame both remain as fine powders, i.e. have a large surface, since otherwise the dissolution is too slow.
  • Further substances, in particular water soluble substances such as acids, colorants, stabilizers, an- tioxidants, vitamins, a ino acids, peptides etc., can be added during stirring.
  • any not dissolved substances are preferably filtered off.
  • a suitable filter has a pore diameter of about 2 ⁇ m.
  • the inventive solution preferably has a pH in the range of about 4.2 to 4.5 in which aspartame - also in a complex with cyclodextrin - is most stable, and the solution should not be stored for more than 6 months .
  • the decompo- sition rate of aspartame in the presence or absence of beta-cyclodextrin is about 6 % in 150 days at 20° and a pH of about 4.5.
  • the beta- cyclodextrin has the tendency to crystallize. Due to the comparably small surface of such crystals, the crystallization can hardly be inverted. Thus, precipita- tion/crystallization at low temperatures should be avoided.
  • aspartame is the sweetener of choice provided that a sufficiently high- concentrated solution can be provided such that it can be dosed without inadmissibly diluting the milk.
  • a sufficiently high- concentrated solution can be provided such that it can be dosed without inadmissibly diluting the milk.
  • Such sufficiently concentrated solution has now been provided by the present invention.
  • With the concentrated solution of the present invention at most 1ml/l has to be added, often less.
  • the advantage of an aspartame solution is that it can be packed in aseptic bags and - due to the liquid form - easily processed in sterile equipment. Any dusting, adherence to walls etc. known for pulverized aspartame is avoided thereby leading to a more constant dosing, less down-time due to maintenance of the equipment etc .
  • One suitable apparatus is the FlexDos ® system of Tetra Pak ® , e.g. the FlexDos ® apparatus designated FDU 2000 or FDU 3000 as described in a prospectus marked n ⁇ 2003 Tetra Pak Arom Pak, Produced by Clavis, Lund, Code 8803en, Printed in Sweden . 2003-03 " .
  • Such apparatus is available from Tetra Pak Arom Pak ® , Maskinvagen 5, SE- 227 30 Lund, Sweden.
  • Further applications of the inventive solution are beverages in general, but also milk products such as fermented or not fermented milk products, e.g. yogurt .
  • the Figure shows the degradation over the time of aspartame in a 1 : 1 complex with beta- cyclodextrine at a pH of about 4.5 and at a temperature of 20°C.
  • Highly concentrated aspartame solutions can e.g. be produced by using the following ingredients:
  • Citric Acid (as Citric Acid Monohydrate) : C 5 H 8 0 7 -H 2 0
  • Cyclodextrin, aspartame and optionally citric acid were dry blended. Then purified water of 50°C was added. After stirring (approx. 150 rpm) for 15. min. the solution was let to cool down. A clear solution was obtained. Agitation at approx. 150 rpm was continued for 24h. The solu- tion became slightly opaque. A sterile filtration through a filter with 0.2 ⁇ m pore width (use of prefilter recommended) was performed. For storage and transport a temperature in the range of 10 to 30°C, preferably of about 20°C, should be ensured.
  • the aspartame (APM) degradation of high concentrated aspartame solution over the time and at 20°C was determined (see Figure) .
  • the aspartame solution prepared as described above can directly be used or packed in aseptic containers, in particular bags; or it can first be further sterilized, e.g. by pasteurization, prior to use or packing, or a pasteurization can be performed on the already filled bags .
  • the bags can be directly used or stored and/or shipped, preferably at temperatures of about 10 to 30°C, much preferred about 20°C.
  • a preferred method for use is that the bag is fixed to a suitable dosing and mixing apparatus such that solution out of the bag is dosed to a larger flow of basic foodstuff, e.g. beverage or, in particular, milk.
  • the milk can in addition be supplemented with other additives such as flavors. It can suitably be sterilized prior to the addition of the aspartame solution and/or in a further purification step, e.g. a pasteurization step, after the supplementation and optional packing into bags for distribution to food markets etc.
  • the aspartame solution of the present invention can e.g. be added at the same point as the flavors .
  • the high-concentrated aspartame solution of the present invention can be used for the production of a broad variety of beverages and foodstuffs .
  • beverages and foodstuffs comprising aspartame and beta cyclodex- trine, in particular in equimolar amounts, are also an object of the present invention.
  • the highly concentrated aspartame solution of the present invention can also be used as a liquid house- hold sweetener for sweetening hot or cold beverages, desserts etc . While there are shown and described presently preferred embodiments of the invention, it is to be distinctly understood that the invention is not limited thereto but may be otherwise variously embodied and practiced within the scope of the following claims.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Microbiology (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention porte sur une solution aqueuse présentant une forte concentration d'aspartame due à l'utilisation de bêta-cyclodextrine en tant qu'agent renforçateur de solubilité.
PCT/CH2003/000587 2003-08-28 2003-08-28 Solution d'aspartame WO2005020716A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CNA038270056A CN1826057A (zh) 2003-08-28 2003-08-28 阿司帕坦溶液
EP03818371A EP1657983A1 (fr) 2003-08-28 2003-08-28 Solution d'aspartame
AU2003250732A AU2003250732A1 (en) 2003-08-28 2003-08-28 Aspartame solution
PCT/CH2003/000587 WO2005020716A1 (fr) 2003-08-28 2003-08-28 Solution d'aspartame

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CH2003/000587 WO2005020716A1 (fr) 2003-08-28 2003-08-28 Solution d'aspartame

Publications (1)

Publication Number Publication Date
WO2005020716A1 true WO2005020716A1 (fr) 2005-03-10

Family

ID=34230813

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH2003/000587 WO2005020716A1 (fr) 2003-08-28 2003-08-28 Solution d'aspartame

Country Status (4)

Country Link
EP (1) EP1657983A1 (fr)
CN (1) CN1826057A (fr)
AU (1) AU2003250732A1 (fr)
WO (1) WO2005020716A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107812022A (zh) * 2017-11-09 2018-03-20 昆药集团血塞通药业股份有限公司 血塞通颗粒及其生产工艺

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097950A1 (fr) * 1982-06-28 1984-01-11 Ajinomoto Co., Inc. Composition stabilisée d'aspartame, procédé pour sa production et denrée alimentaire aqueuse
US4751095A (en) * 1983-07-28 1988-06-14 Karl Curtis L Aspartame stabilization with cyclodextrin
US4931302A (en) * 1989-02-17 1990-06-05 Kraft General Foods, Inc. Aseptically-packaged, aspartame-containing puddings
WO2000015049A1 (fr) * 1998-09-17 2000-03-23 The Nutrasweet Company UTILISATION DE CYCLODEXTRINE POUR STABILISER LE N-[N- (3,3-DIMETHYLBUTYL) -L-α- ASPARTYL] -L-PHENYLALANINE 1-ESTER METHYLIQUE

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097950A1 (fr) * 1982-06-28 1984-01-11 Ajinomoto Co., Inc. Composition stabilisée d'aspartame, procédé pour sa production et denrée alimentaire aqueuse
US4751095A (en) * 1983-07-28 1988-06-14 Karl Curtis L Aspartame stabilization with cyclodextrin
US4931302A (en) * 1989-02-17 1990-06-05 Kraft General Foods, Inc. Aseptically-packaged, aspartame-containing puddings
WO2000015049A1 (fr) * 1998-09-17 2000-03-23 The Nutrasweet Company UTILISATION DE CYCLODEXTRINE POUR STABILISER LE N-[N- (3,3-DIMETHYLBUTYL) -L-α- ASPARTYL] -L-PHENYLALANINE 1-ESTER METHYLIQUE

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "Food uses for cyclodextrins limited only by imagination.", FOOD ENGINEERING 1992, vol. 64, no. 11, November 1992 (1992-11-01), pages 22, 24, XP009031669 *

Also Published As

Publication number Publication date
AU2003250732A1 (en) 2005-03-16
EP1657983A1 (fr) 2006-05-24
CN1826057A (zh) 2006-08-30

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