NO121493B - - Google Patents

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NO121493B
NO121493B NO165773A NO16577366A NO121493B NO 121493 B NO121493 B NO 121493B NO 165773 A NO165773 A NO 165773A NO 16577366 A NO16577366 A NO 16577366A NO 121493 B NO121493 B NO 121493B
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Norway
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monosaccharide units
fermentation
value
corresponds
oligosaccharides
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NO165773A
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Norwegian (no)
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E Conrad
G Frostell
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Lyckeby Staerkelsefoeraedling
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Publication of NO121493B publication Critical patent/NO121493B/no

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B30/00Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
    • C08B30/12Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
    • C08B30/18Dextrin, e.g. yellow canari, white dextrin, amylodextrin or maltodextrin; Methods of depolymerisation, e.g. by irradiation or mechanically
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30Artificial sweetening agents
    • A23L27/33Artificial sweetening agents containing sugars or derivatives
    • A23L27/34Sugar alcohols

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Saccharide Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Confectionery (AREA)
  • Seasonings (AREA)

Description

Fremgangsmåte for fremstilling av et sukkererstatningsmiddel. Method for producing a sugar substitute.

Tillegg til patent nr. 117.422Addendum to patent no. 117,422

Oppfinnelsen vedrorer en modifikasjon av fremgangsmåten for fremstilling av et sukkererstatningsmiddel ifolge norsk patent nr. 117.422. The invention relates to a modification of the method for producing a sugar substitute according to Norwegian patent no. 117,422.

Det er kjent at for fremstilling av slike produkter som vanlig-vis inneholder sukker, f.eks. karameller, konfektyrer og andre sotsaker, å anvende sorbitol for å unngå faren for karies. For-delen ved anvendelsen av sorbitol består i at sorbitol ikke for-årsaker noen gjæring som kan være hovedårsaken til at karies og andre ugunstige tilstander ved tennene fremkommer. It is known that for the production of such products which usually contain sugar, e.g. caramels, confectionery and other sweets, to use sorbitol to avoid the risk of caries. The advantage of using sorbitol is that sorbitol does not cause any fermentation which can be the main cause of caries and other unfavorable conditions in the teeth.

Det har dog vist seg at ved fortæring av sorbitolholdig næring og nytelsesmiddel, f.eks. karameller ofte medforer fordoyelses-forstyrrelser avhengig av den lille resorpsjon av sorbitol i tarmen, hvorved en avforende virkning oppstår. Hos folsomme personer fremkommer slike besvær etter fortæring av ca. 50 g ren sorbitol, andre personer kan tåle betydelig storre sorbitolmeng-der uten noen som helst bieffekter fremkommer. However, it has been shown that when consuming sorbitol-containing food and recreational drugs, e.g. Caramels often cause digestive disturbances depending on the small resorption of sorbitol in the intestine, whereby a laxative effect occurs. In sensitive people, such problems appear after consuming approx. 50 g of pure sorbitol, other people can tolerate significantly larger amounts of sorbitol without any side effects appearing.

Av det forananforte fremgår at det foreligger et behov for et ytterligere forbedret erstatningsmiddel for sukker for anvendelse i karameller, konfektyrer og ligenede produkter, hvilket erstatningsmiddel ikke medforer en fordoyelsesbesværlighet og dessuten minsker risikoen for at karies oppstår. From the above it appears that there is a need for a further improved substitute for sugar for use in caramels, confectionery and similar products, which substitute does not cause difficulty in digestion and also reduces the risk of caries occurring.

Foreliggende oppfinnelse vedrorer et slikt forbedret sukkererstatningsmiddel som ikke har noen avforende virkning og ikke eller i bare ytterst liten grad har anledning til kariesangrep på tennene. The present invention relates to such an improved sugar substitute which has no exfoliating effect and does not, or only to an extremely small extent, cause caries to attack the teeth.

Grunnsubstansen for sukkererstatningsmidlet ifblge oppfinnelsen er polysakkarider, f.eks. stivelse og sukkererstatningsmidlet ifolge oppfinnelsen fremstilles på slik måte at polysakkarid, f.eks. stivelse, underkastes en partiel hydrolyse, f.eks. ved forhoyet temperatur på ca. 150°C, under sure, svakt hydrolyserende betingelser, slik som ved en pH-verdi mellom 2 og 4, og under anvendelse av en svak organisk eller uorganisk syre eller et surt salt som surt medium. Ved hydrolysen tilpasser temperatur, pH-verdi og trykk slik i forhold tii hverandre at man får den onskede partielle hydrolyse av utgangsmaterialet. The basic substance for the sugar substitute according to the invention is polysaccharides, e.g. starch and the sugar substitute according to the invention are prepared in such a way that polysaccharide, e.g. starch, is subjected to a partial hydrolysis, e.g. at an elevated temperature of approx. 150°C, under acidic, slightly hydrolyzing conditions, such as at a pH value between 2 and 4, and using a weak organic or inorganic acid or an acidic salt as acidic medium. During the hydrolysis, the temperature, pH value and pressure are adapted in such a way that the desired partial hydrolysis of the starting material is obtained.

Fortrinnsvis gjennomfores dog den svakt partielle hydrolyse under anvendelse av et lavaktivt enzym idet hydrolysen gjennomfores under optimale betingelser for det spesielt anvendte enzym. Preferably, however, the weak partial hydrolysis is carried out using a low-activity enzyme, as the hydrolysis is carried out under optimal conditions for the particular enzyme used.

Det for stivelseshydrolysen anvendte enzym består fortrinnsvis av et enzym med svakt hydrolyserende virkning. Et flertal enzymer av denne art kjennes på markedet. The enzyme used for starch hydrolysis preferably consists of an enzyme with a weak hydrolysing effect. A majority of enzymes of this type are known on the market.

Et foretrukket egnet poly-sakkaridutgangsmateriale er stivelse, A preferred suitable polysaccharide starting material is starch,

f.eks. maisstivelse eller potetstivelse.e.g. corn starch or potato starch.

Ved den partielle hydrolyse av stivelse omdannes denne hovedsaklig til dextriner og lavere poly- eller oligosakkarider, som inneholder 2-20 monosakkaridenheter, fortrinnsvis 3-10 monosakkaridenheter, mens frie monosakkarider, slik som glukose eller disakkarider i det hele tatt ikke eller bare i begrenset omfang dannes. Ifolge oppfinnelsen gjennomfores hydrolysen slik at poly- eller oligosakkaridene i middeltall inneholder omtrent 3-5 monosakkaridenheter, f.eks. 4 monosakkaridenheter, idet innholdet av reduserende grupper er lavere enn det som tilsvarer en dextroseekvivalentverdi på 15 %. Når den onskede nedbrytning er oppnådd, avbrytes hydrolysen, hvilket ved hydrolyse i surt miljo og ved forhoyet temperatur skjer ved noytralisasjon av syren og/eller senkning av temperaturen, mens avbrytelsen av enzymatisk hydrolyse skjer ved temperaturforhoyelse for å 6de-legge enzymet. During the partial hydrolysis of starch, this is mainly converted into dextrins and lower polysaccharides or oligosaccharides, which contain 2-20 monosaccharide units, preferably 3-10 monosaccharide units, while free monosaccharides, such as glucose or disaccharides not at all or only to a limited extent is formed. According to the invention, the hydrolysis is carried out so that the average number of polysaccharides or oligosaccharides contains approximately 3-5 monosaccharide units, e.g. 4 monosaccharide units, the content of reducing groups being lower than that corresponding to a dextrose equivalent value of 15%. When the desired decomposition has been achieved, the hydrolysis is interrupted, which in the case of hydrolysis in an acidic environment and at an elevated temperature occurs by neutralization of the acid and/or lowering the temperature, while the interruption of enzymatic hydrolysis occurs when the temperature is increased to 6de-lay the enzyme.

Ifolge en utforelsesform for fremgangsmåten underkastes det hy-drolyserte materialet for ytterligere reduksjon av mengden forgjærbare mono- og disakkarider en gjæring i hvilke tilfelle hy-drolyseprodukter kan oppvise et innhold reduserende grupper, According to one embodiment of the method, the hydrolysed material is subjected to a fermentation to further reduce the amount of fermentable mono- and disaccharides, in which case hydrolysis products may exhibit a content-reducing group,

som er storre enn det som tilsvarer en dextroseekvivalentverdi på 15 %, for de en reduksjon av mengden reduserende stoffer til under denne grenseverdi skjer ved gjæring. which is greater than what corresponds to a dextrose equivalent value of 15%, for which a reduction of the amount of reducing substances to below this limit value occurs during fermentation.

De ved stivelsens partielle hydrolyse erholdte dextriner og lavere poly- eller oligosakkarider underkastes derpå på i og for seg kjent måte en fullstendig hydrogenering, fortrinnsvis ved forhoyet temperatur, med anvendelse av for eksempel Raney-nikkel som katalysator. The dextrins and lower polysaccharides or oligosaccharides obtained by the partial hydrolysis of the starch are then subjected in a manner known per se to a complete hydrogenation, preferably at an elevated temperature, using, for example, Raney nickel as a catalyst.

Ved hydreringen overfores samtlige resulterende monosakkarid-grupper som forekommer i endestilling i dextrinene eller poly-eller oligosakkaridene, til fullstendig hydrert tilstand, dvs. det dannes en pol<y>dforbindelse. Ved dette nedsettes materialets forgjærbarhet. During the hydration, all resulting monosaccharide groups occurring in the terminal position in the dextrins or poly- or oligosaccharides are transferred to a fully hydrated state, i.e. a pol<y>d compound is formed. This reduces the fermentability of the material.

Den hydrerte blanding av dextriner og poly- eller oligosakkarider som oppnås på foran angitte måte, og som i middeltall inneholder 3-5 monosakkaridenheter pr. molekyl, oppviser en lavere sothetsgrad enn sakkarose, hvilket beror på det forhold at mono-eller disakkaridene i hydrolyseringstrinnet i det hele tatt ikke eller bare i ringe grad dannes, eller at disse fjernes ved det eventuelt innskutte forgjæringstrinn. Av denne grunn kan man blande det ved hydreringstrinnet erholdte produkt med et syntet-isk sotningsmiddel, slik som sakkarin eller natriumcyklamat i slik mengde, at man får et produkt med en sothetsgrad som tilsvarer den for sakkarose. På denne måte oppnås at den erholdte blanding direkte kan erstatte en tilsvarende mengde sakkarose ved fremstilling av næringsmiddel og nytelsesmidler av de mest forskjellige arter inklusiv karameller og andre sotsaker. The hydrated mixture of dextrins and polysaccharides or oligosaccharides which is obtained in the manner indicated above, and which on average contains 3-5 monosaccharide units per molecule, exhibits a lower degree of sweetness than sucrose, which is due to the fact that the mono- or disaccharides in the hydrolysis step are not formed at all or only to a small extent, or that these are removed by the possibly interrupted fermentation step. For this reason, the product obtained in the hydration step can be mixed with a synthetic sweetening agent, such as saccharin or sodium cyclamate in such an amount, that a product with a degree of sweetness corresponding to that of sucrose is obtained. In this way, it is achieved that the obtained mixture can directly replace a corresponding amount of sucrose in the production of food and pleasure products of the most diverse types, including caramels and other sweets.

Produkt ifolge oppfinnelsen kan fremstilles i form av en viskos sirup, dvs. i opplosning, men det er både mulig å underkaste oppldsningen en torring, slik at man får et hvitt pulver, som bare i liten grad er hydroskopisk. Torringen kan skje på vanlig forekommende måte, f.eks. ved forstbvningstbrring, valsetorring eller frysetorring. Product according to the invention can be produced in the form of a viscous syrup, i.e. in solution, but it is also possible to subject the solution to drying, so that a white powder is obtained, which is only slightly hydroscopic. The drying can take place in the usual way, e.g. by solidification removal, roller drying or freeze drying.

Oppfinnelsen belyses nærmere ved hjelp av folgende eksempler, i hvilke deler og prosent refererer til torrvekt, om ikke annet er angitt, og temperaturene angis i Celsiusgrader. The invention is explained in more detail by means of the following examples, in which parts and percentages refer to dry weight, unless otherwise stated, and the temperatures are given in degrees Celsius.

EKSEMPEL I Sur hydrolyse.EXAMPLE I Acid hydrolysis.

En oppslemming av potetstivelse, som inneholder 45% torrsubstans (2000 kg potetmel inneholdende 1800 kg torr stivelse og 2000 liter vann) ble blandet med 5 liter 37 %-ig teknisk saltsyre. Blandingens pH var 2,2. Forsukringen ble gjennomfort i 30 minutter ved 130° og ved et overtrykk på 3 for å overfore stivelsen til et dextrinholdig nedbrytningsprodukt. Mengden reduserte substanser, beregnet som dextros, var 12 %. Reaksjonsblandingen ble nøytralisert til pH 6,5 med 20 liter 15 % natriumkarbonatopplosning. Opplosningen ble avfarget med aktivt karbon og de faste substanser ble fjernet gjennom sentrifugering. Derpå ble Raney-nikkelkatalysator i en mengde på 2 %, dvs. 36 kg avsatt.Hydreringen ble gjennomfort ved et hydrogengasstrykk på 75 og ved en temperatur ved 145°. Hydrogengassforbruket var 30 m hy-drogengass, beregnet ved NTP. Hydreringen gjennomfores på vanlig måte og inntil en likevektstilstand oppnås, dvs. inntil samtlige reduserende stoffer er hydrogenert. Katalysatoren fjernes ved separering. A slurry of potato starch, which contains 45% dry substance (2000 kg of potato flour containing 1800 kg of dry starch and 2000 liters of water) was mixed with 5 liters of 37% technical hydrochloric acid. The pH of the mixture was 2.2. The saccharification was carried out for 30 minutes at 130° and at an overpressure of 3 to convert the starch into a dextrin-containing degradation product. The amount of reduced substances, calculated as dextrose, was 12%. The reaction mixture was neutralized to pH 6.5 with 20 liters of 15% sodium carbonate solution. The solution was decolorized with activated carbon and the solids were removed by centrifugation. Raney nickel catalyst in an amount of 2%, i.e. 36 kg, was then deposited. The hydrogenation was carried out at a hydrogen gas pressure of 75 and at a temperature of 145°. Hydrogen gas consumption was 30 m hydrogen gas, calculated at NTP. The hydrogenation is carried out in the usual way and until an equilibrium state is reached, i.e. until all reducing substances have been hydrogenated. The catalyst is removed by separation.

For fjerning av metalljoner og syrasjon ble opplosningen fort gjennom en katjonutvekslerharpiks og gjennom en anjonutveksler-harpiks, hvoretter opplosningen ble konsentrert ved fordampning i vakuum og forstovningstorres for å gi ikke hygroskopisk pulver. To remove metal ions and acidification, the solution was passed through a cation exchange resin and through an anion exchange resin, after which the solution was concentrated by evaporation in vacuo and spray-dried to give a non-hygroscopic powder.

Når man tilsikter å fremstille et produkt, som direkte kan an-vendes som erstatningsmiddel for sakkarose, ble den konsentrerte opplosning for forstovningstorring tilsatt natriumcyklamat i en mengde tilsvarende 10 g pr. kg torrsubstans. When it is intended to produce a product which can be directly used as a substitute for sucrose, sodium cyclamate was added to the concentrated solution for spray drying in an amount corresponding to 10 g per kg dry matter.

EKSEMPEL II Enzymatisk hydrolyse.EXAMPLE II Enzymatic hydrolysis.

Den 45 %-ige stivelsessuspensjon ifolge eksempel I ble blandet med 3 kg enzym (bakteriell a-Amylase). Oppløsningens pH-verdi var 6,2. Ved tilsetning av natriumkarbonatopplosning ble pH-ver-dien innstilt på 7,5. Suspensjonen ble oppvarmet 15 minutter ved en temperatur på 90°. Derpå ble enzymet innaktivitert gjennom oppvarmning under 5 minutter ved en temperatur på 110°C. Sluttproduktet utgjorde en opplosning, som hovedsaklig inneholdt dextrinholdig nedbrytningsprodukter. Innholdets reduserende stoffer beregnet som dextros, var 4,6 %. Opplosningen ble avfarget, separert og hydrert, slik som beskrevet i eksempel I. I hydreringstrinnet ble 26 m 3 hydrogen forbrukt ved NTP. The 45% starch suspension according to example I was mixed with 3 kg of enzyme (bacterial α-Amylase). The solution's pH value was 6.2. By adding sodium carbonate solution, the pH value was set to 7.5. The suspension was heated for 15 minutes at a temperature of 90°. The enzyme was then inactivated by heating for 5 minutes at a temperature of 110°C. The final product was a solution, which mainly contained dextrin-containing degradation products. The content of reducing substances, calculated as dextrose, was 4.6%. The solution was decoloured, separated and hydrated, as described in example I. In the hydration step, 26 m 3 of hydrogen were consumed at NTP.

EKSEMPEL III Forgjæring av mono- og disakkarider som mellom-trinn. EXAMPLE III Fermentation of mono- and disaccharides as an intermediate step.

For å få et lavest mulig innhold av mono- og disakkarider ble folgende mellomliggende trinn utfort ved fremgangsmåten ifolge eksempel I. In order to obtain the lowest possible content of mono- and disaccharides, the following intermediate steps were carried out in the method according to example I.

Ved å oke forsukringstiden i eksempel I fra 30 minutter til 60By increasing the saccharification time in example I from 30 minutes to 60

minutter (eller fra 15 minutter til 60 minutter i eksempel 2)minutes (or from 15 minutes to 60 minutes in example 2)

ble en reduseringsverdi på 27 % oppnådd. Opplosningen ble nøy-a reduction value of 27% was achieved. The solution was precisely

tralisert til pH 5,0 med 18 liter 15 96-ig natriumkarbonatopplos-tralized to pH 5.0 with 18 liters of 15 96-ig sodium carbonate solution

ning. Temperaturen ble innstilt på 30° og 10 kg bryggerigjær (Saccharomycetes cerevisiae) ble tilsatt. Forgjæringen ble gjennomfort på vanlig måte og avsluttet etter omtrent 48 timer, nothing. The temperature was set at 30° and 10 kg of brewer's yeast (Saccharomycetes cerevisiae) was added. The pre-fermentation was carried out in the usual way and ended after approximately 48 hours,

da karbonsyreutvekslingen opphdrte. Mengden reduserende sukker var da redusert til omtrent 1,2 96. Opplosningen ble avfarget med aktivt karbon og filtrert. Den erholdte klare opplosningen ble hydrert slik som beskrevet ovenfor. Den forbrukte hydrogen- when carbonic acid exchange ceased. The amount of reducing sugar was then reduced to about 1.2 96. The solution was decolorized with activated carbon and filtered. The resulting clear solution was hydrated as described above. The consumed hydrogen

gassmengden var 12 m 3 ved NTP.the amount of gas was 12 m 3 at NTP.

Den hydrogenerte opplosning ble skilt fra katalysatoren, filtrertThe hydrogenated solution was separated from the catalyst, filtered

og behandlet med jonutvekslerharpiks. Ved det etterfølgende for-dampningstrinn ble den dannede alkohol fjernet. and treated with ion exchange resin. In the subsequent evaporation step, the alcohol formed was removed.

Claims (1)

Modifikasjon av fremgangsmåten for fremstilling av et sukkererstatningsmiddel ifolge norsk patent nr. 117.422, fortrinnsvis for anvendelse i karameller, konfektyrer og andre sotsaker, karakterisert ved at man hydrolyserer poly-sakkaridholdig utgangsmateriale, fortrinnsvis stivelse, til et produkt, som består av dextriner og/eller lavere poly- eller oligosakkarider, som inneholder 2-20 monosakkaridenheter,Modification of the method for the production of a sugar substitute according to Norwegian patent no. 117,422, preferably for use in caramels, confections and other sweet products, characterized by hydrolyzing polysaccharide-containing starting material, preferably starch, into a product consisting of dextrins and/or lower polysaccharides or oligosaccharides, containing 2-20 monosaccharide units, fortrinnsvis 3-10 monosakkaridenheter, idet middelverdien for monosakkaridenhetene pr. molekyl er 3 - 5 og fortrinnsvis 4, idet innholdet reduserende grupper er lavere enn hva som tilsvarer en dextroseekvivalentverdi på 15 96, eventuelt underkaster de i hydrolysetrinnet dannede forgjærbare mono- og disakkarider en forgjæring, hvis mengden av de i hydrolysetrinnet dannede substanser med reduserbare grupper overstiger det som tilsvarer en dextroseekvivalentverdi på 15 96, ved hvilken forgjæring denne verdi senkes til under 15 96 og at man deretter hydroge-nerer produktet som inneholder dextriner og/eller lavere poly-eller oligosakkarider, hvoretter man, hvis onsket, for okning av sothetsgraden i det ved hydrogeneringen erholdte produkt tilsette dette sotningsmiddel, f.eks. sakkarin eller natriumcyklamat, i en slik mengde at blandingens sothetsgrad tilsvarer den for sukker.preferably 3-10 monosaccharide units, the average value for the monosaccharide units per molecule is 3 - 5 and preferably 4, as the content of reducing groups is lower than what corresponds to a dextrose equivalent value of 15 96, possibly subject the fermentable mono- and disaccharides formed in the hydrolysis step to a fermentation, if the quantity of the substances with reducible groups formed in the hydrolysis step exceeds what corresponds to a dextrose equivalent value of 15 96 , by which pre-fermentation this value is lowered to below 15 96 and that the product containing dextrins and/or lower poly- or oligosaccharides is then hydrogenated, after which, if desired, to increase the degree of sootiness in the product obtained by hydrogenation, this sooting agent is added, e.g. . saccharin or sodium cyclamate, in such a quantity that the degree of sweetness of the mixture corresponds to that of sugar.
NO165773A 1965-11-29 1966-11-28 NO121493B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB50609/65A GB1169538A (en) 1965-11-29 1965-11-29 Sugar Substitute and a Process for the Preparation thereof

Publications (1)

Publication Number Publication Date
NO121493B true NO121493B (en) 1971-03-08

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BE (1) BE690318A (en)
CH (1) CH489540A (en)
DE (1) DE1692721B2 (en)
DK (1) DK136132B (en)
FI (1) FI47626C (en)
FR (1) FR1502352A (en)
GB (1) GB1169538A (en)
IL (1) IL26905A (en)
LU (1) LU52387A1 (en)
NL (1) NL138892B (en)
NO (1) NO121493B (en)
SE (1) SE308980B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4947547A (en) * 1972-09-11 1974-05-08
FR2445839A1 (en) * 1979-01-08 1980-08-01 Roquette Freres HYDROLYSATE OF POSSIBLE HYDROGEN STARCH, PROCESS FOR THE PREPARATION THEREOF AND APPLICATIONS THEREOF
US4435380A (en) 1982-01-29 1984-03-06 Lever Brothers Company Humectants for clear gel dentifrice compositions
GB2166637A (en) * 1984-10-04 1986-05-14 Powell & Scholefield Limited Drink concentrate
DK0572424T3 (en) * 1991-02-20 1997-04-14 Cultor Oy Reduced polydextrose
BR9907096A (en) 1998-01-20 2000-10-24 Grain Processing Corp Reduced malto-oligosaccharides

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FR1502352A (en) 1967-11-18
IL26905A (en) 1970-07-19
DE1692721A1 (en) 1970-05-27
CH489540A (en) 1970-04-30
GB1169538A (en) 1969-11-05
FI47626C (en) 1974-02-11
DK136132C (en) 1980-03-03
NL6616422A (en) 1967-05-30
SE308980B (en) 1969-03-03
FI47626B (en) 1973-10-31
DK136132B (en) 1977-08-22
BE690318A (en) 1967-05-02
NL138892B (en) 1973-05-15
LU52387A1 (en) 1967-01-18
DE1692721B2 (en) 1973-04-19

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