EP4103574A1 - Concentrés d'allulose sous forme amorphe solide - Google Patents

Concentrés d'allulose sous forme amorphe solide

Info

Publication number
EP4103574A1
EP4103574A1 EP21703924.7A EP21703924A EP4103574A1 EP 4103574 A1 EP4103574 A1 EP 4103574A1 EP 21703924 A EP21703924 A EP 21703924A EP 4103574 A1 EP4103574 A1 EP 4103574A1
Authority
EP
European Patent Office
Prior art keywords
allulose
weight
concentrate
fructose
syrup
Prior art date
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.)
Pending
Application number
EP21703924.7A
Other languages
German (de)
English (en)
Inventor
Anna JUNKLEWITZ
Stephan Mohr
Steffen BUTZ
Michael BOGNAR
Timo Koch
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.)
Savanna Ingredients GmbH
Original Assignee
Savanna Ingredients GmbH
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 Savanna Ingredients GmbH filed Critical Savanna Ingredients GmbH
Publication of EP4103574A1 publication Critical patent/EP4103574A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification

Definitions

  • the invention is in the field of food technology and relates to allulose concentrates and a method for their production.
  • Allulose is a low-calorie sugar with a similar sweet taste to sugar. Allulose is one of many different sugars that occur in very small amounts in nature. Allulose was originally identified from wheat and has since been found in certain fruits such as jackfruit, figs, and raisins. Allulose is naturally found in small amounts in a variety of sweet foods such as caramel sauce, maple syrup, and brown sugar. Allulose is absorbed by the body but not metabolized, so it is virtually calorie-free.
  • allulose is commercialized in the form of a syrup.
  • these allulose syrups show considerable stability problems, so that the quality of the product is no longer optimal after a longer storage period, in particular with regard to the sensory properties, color, purity and temperature resistance.
  • the drying of food is one of the oldest and at the same time most natural preservation methods and has proven itself to this day as a gentle preservation.
  • Drying is generally understood to mean the removal of liquids from the material to be dried, by evaporation, evaporation or other technical processes.
  • the dry material can be produced in the form of powder or granules, in pieces or slices or, for example in the case of fruit, left whole. Due to the removal of moisture, the dry goods have a significantly lower weight after the treatment, while at the same time the important and valuable components are retained.
  • Freeze drying is a particularly preferred drying method because it has proven to be a particularly gentle drying method in terms of taste or rehydration ability. In this process, however, the material to be dried must first be frozen in order to sublimate the water from it. The disadvantage of this process is the fact that it is very energy-intensive.
  • the object of the present invention was thus to provide allulose concentrates in solid, amorphous form, which are produced from an allulose syrup, which are free from the disadvantages outlined above.
  • the new allulose concentrates should have improved storage and temperature stability compared to allulose in syrup form, so that an allulose syrup is obtained after reconstitution by adding water which, in terms of its composition and organoleptic properties, does not differ from the freshly prepared, original allulose syrup is different.
  • the present invention relates to allulose concentrates in solid amorphous form, which are characterized in that they have an allulose content of at least about 20% by weight.
  • the allulose concentrates according to the invention have a considerably improved storage and temperature stability compared to the corresponding alluloses in syrup form from which they were obtained.
  • the solid amorphous allulose concentrates according to the invention enable the production of an allulose syrup by reconstitution by means of the addition of water, which in the In terms of its composition and organoleptic properties, it was indistinguishable from the freshly prepared original allulose syrup from which it was obtained.
  • concentrate relates to dry or aqueous compositions in which a total amount of allulose of 20 to 99% by weight, based on the total solids, is contained.
  • “Syrup” in the context of the present invention is a thick, concentrated solution of a sugar or sugar substitute that is obtained from sugary liquids or plant extracts by cooking or other techniques, in particular by enzymatic cleavage or conversion processes.
  • Allulose also called psicose, is a ketohexose.
  • allulose is preferably provided in the form of the D-enantiomer, i.e. D-allulose (CAS No. 551-68-8).
  • D-allulose can exist in the form of various anomers such as a-D-allulose and ß-D-allulose.
  • the solid amorphous allulose concentrates according to the invention are at least 90% by weight, preferably at least 95% by weight and in particular about 98 to about 99.5% by weight in amorphous form.
  • the allulose concentrates according to the invention have an allulose content of at least about 40% by weight, preferably at least about 50% by weight, preferably at least about 60% by weight, particularly preferably at least about 70% by weight. -%, and particularly preferably at least about 75% by weight.
  • the allulose concentrates according to the invention of the present invention are distinguished by the fact that the allulose content is in the range from about 20 to about 99% by weight.
  • the allulose content is in the range from about 25 to about 95% by weight, preferably in the range from about 40 to about 90% by weight, preferably in the range from about 45 to about 85% by weight, and particularly preferably in the range from about 50 to about 80% by weight.
  • the allulose concentrates according to the invention can also contain fructose.
  • the allulose concentrates according to the invention can have a maximum fructose content of about 80% by weight.
  • the allulose concentrates according to the invention have a content of a maximum of about 60% by weight, preferably a maximum of about 50% by weight, preferably a maximum of about 40% by weight, particularly preferably a maximum of about 30% by weight , and particularly preferably a maximum of about 25% by weight of fructose.
  • the fructose content is in the range from about 25 to about 80% by weight, preferably in the range from about 40 to about 60% by weight, and particularly preferably in the range from about 45% up to about 55% by weight.
  • the allulose concentrates according to the invention have a content of at least about 20% by weight of allulose and a maximum of about 80% by weight of fructose, preferably at least about 25% by weight of allulose and a maximum of about 75% by weight % Fructose, preferably at least about 40% by weight allulose and at most about 60% by weight fructose, preferably at least about 50% by weight allulose and at most about 50% by weight fructose, preferably at least about 60% by weight allulose and a maximum of about 40% by weight of fructose, preferably at least about 70% by weight of allulose and a maximum of about 30% by weight of fructose, and particularly preferably at least about 75% by weight of allulose and a maximum of about 25% by weight of fructose .
  • the weight ratio of allulose: fructose is about 20:80 to about 80:20, in a second embodiment about 90:10 to 95: 5.
  • the solid amorphous allulose concentrates according to the invention are characterized in that they have a maximum content of about 0.1% by weight of water, preferably of a maximum of about 0.05% by weight and particularly preferably of a maximum of about 0.01 Wt%.
  • Another object of the invention relates to a method for producing a solid amorphous allulose concentrate, comprising or consisting of the following steps:
  • step (c) drying the intermediate product from step (b) or the allulose concentrate from step (a) on a spray, freeze or belt dryer with subsequent comminution, and finally
  • an allulose concentrate is initially provided in syrup form; it can be a commercially available allulose concentrate in syrup form or an allulose concentrate in syrup form, which was produced by a method from the prior art.
  • the allulose concentrate in syrup form from step (a) comprises or consists of the following components:
  • the allulose concentrate in syrup form from step (a) has a content of about 25 to about 40% by weight of water, particularly preferably a content of about 30% by weight.
  • the allulose concentrate in syrup form from step (a) has a dry matter of about 10 to about 30% by weight.
  • the allulose concentrate in syrup form from step (a) is subjected to evaporation, cooling or displacement crystallization with a protic solvent or a combination of these.
  • the allulose crystals obtained in this way are preferably separated off by filtration and then subjected to drying with subsequent comminution; then the dry end product obtained in this way is discharged (steps (c) and (d) of the process according to the invention).
  • Suitable protic solvents for the crystallization of the allulose from the allulose concentrate in syrup form are branched or unbranched Ci-C 6 alcohols, preferably ethanol and / or isopropanol. During the crystallization, the solid then consists entirely or at least predominantly of ß-D-psicopyranose.
  • the allulose concentrate in syrup form from step (a) can optionally be fed into an evaporator, preferably a plate film evaporator, in which it is applied with a temperature gradient of about 100 to about 50 ° C and in particular about 95 to about 55 ° C and / or a pressure gradient is gently dewatered, so that the intermediate product obtained in this way has a dry matter of about 60 to about 85% by weight, preferably about 80% by weight.
  • the allulose concentrate in syrup form from step (a) or the concentrated intermediate product from step (b) is then likewise dried.
  • the method described above enables the production of the solid amorphous allulose concentrates.
  • the present invention therefore also relates to amorphous, solid allulose concentrates which can be obtained by
  • step (b) optionally the concentrate from step (a) is concentrated
  • step (c) Subjecting the intermediate product from step (b) or the allulose concentrate from step (a) to drying on a spray, freeze or belt dryer with subsequent comminution, and finally
  • the solid amorphous allulose concentrates according to the invention represent an excellent alternative to storage over a longer period of the previously customary allulose syrups, since the concentrates are characterized by improved resistance and stability.
  • a freshly prepared allulose concentrate in syrup form (product A) with a dry matter of 70 wt .-% (65 wt .-% allulose and 5 wt .-% fructose) was in a plate film evaporator with application of a temperature gradient from 95 to 55 ° C evaporated to a dry matter of 75% by weight.
  • the intermediate product obtained was applied to the conveyor belt of a vacuum belt dryer via a feed pump. This had three heating zones (60, 50 and 40 ° C) and a cooling zone (20 ° C) (pressure: 40 mbar).
  • the product obtained was crushed and packaged, and stored at 22 ° C. for 14 months. After this time, the syrup was reconstituted by adding an appropriate amount of water, so that an allulose concentrate in syrup form (product A1) was obtained, which was identical to the original product A in terms of composition.
  • a glass bottle was filled with a freshly prepared product A, as defined in Example 1.
  • the product was stored for 14 months under identical conditions as the product according to the invention according to Example 1, so that a product A2 was obtained.
  • the solid amorphous allulose concentrates according to the invention therefore represent an excellent alternative for storing the previously customary allulose syrups over a longer period of time, since the concentrates are distinguished by their resistance and stability.
  • allulose syrups can be produced reproducibly in a very simple and efficient manner from the solid amorphous allulose concentrates according to the invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Catalysts (AREA)
  • Materials For Medical Uses (AREA)

Abstract

L'invention concerne des concentrés d'allulose sous forme amorphe solide, caractérisés en ce qu'ils contiennent au moins environ 20 % en poids d'allulose. L'invention concerne également un procédé de fabrication de ces concentrés.
EP21703924.7A 2020-02-12 2021-02-08 Concentrés d'allulose sous forme amorphe solide Pending EP4103574A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20156797.1A EP3865499A1 (fr) 2020-02-12 2020-02-12 Concentrés d'allulose sous forme solide amorphe
PCT/EP2021/052966 WO2021160564A1 (fr) 2020-02-12 2021-02-08 Concentrés d'allulose sous forme amorphe solide

Publications (1)

Publication Number Publication Date
EP4103574A1 true EP4103574A1 (fr) 2022-12-21

Family

ID=69571904

Family Applications (2)

Application Number Title Priority Date Filing Date
EP20156797.1A Withdrawn EP3865499A1 (fr) 2020-02-12 2020-02-12 Concentrés d'allulose sous forme solide amorphe
EP21703924.7A Pending EP4103574A1 (fr) 2020-02-12 2021-02-08 Concentrés d'allulose sous forme amorphe solide

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP20156797.1A Withdrawn EP3865499A1 (fr) 2020-02-12 2020-02-12 Concentrés d'allulose sous forme solide amorphe

Country Status (5)

Country Link
US (1) US20230126056A1 (fr)
EP (2) EP3865499A1 (fr)
KR (1) KR20220140784A (fr)
MX (1) MX2022009908A (fr)
WO (1) WO2021160564A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4000419A1 (fr) 2020-11-23 2022-05-25 Savanna Ingredients GmbH Séchage des cristeaux allulose
WO2024047121A1 (fr) 2022-09-01 2024-03-07 Savanna Ingredients Gmbh Procédé de préparation d'une composition d'allulose particulaire

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101189640B1 (ko) * 2010-03-26 2012-10-12 씨제이제일제당 (주) Ｄ-사이코스 결정을 제조하는 방법
ES2541653B1 (es) 2015-02-26 2016-04-13 Francisco Javier VILLAR CLOQUELL Dispositivo de trazado y pintado de dibujos en relieve para ciegos y personas con dificultad motora manual
WO2017029244A1 (fr) * 2015-08-14 2017-02-23 Pfeifer & Langen GmbH & Co. KG Composition d'allulose en poudre
US20190315790A1 (en) 2016-11-11 2019-10-17 Pfeifer & Langen GmbH & Co. KG Synthesis of d-allulose
KR102072695B1 (ko) * 2016-12-08 2020-03-02 주식회사 삼양사 재순환을 이용한 사이코스의 제조방법 및 장치

Also Published As

Publication number Publication date
US20230126056A1 (en) 2023-04-27
WO2021160564A1 (fr) 2021-08-19
KR20220140784A (ko) 2022-10-18
MX2022009908A (es) 2022-09-09
EP3865499A1 (fr) 2021-08-18

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