WO1996007331A1 - Compositions comprenant des cristaux combines, son procede de preparation et son utilisation - Google Patents

Compositions comprenant des cristaux combines, son procede de preparation et son utilisation Download PDF

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Publication number
WO1996007331A1
WO1996007331A1 PCT/FI1995/000490 FI9500490W WO9607331A1 WO 1996007331 A1 WO1996007331 A1 WO 1996007331A1 FI 9500490 W FI9500490 W FI 9500490W WO 9607331 A1 WO9607331 A1 WO 9607331A1
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WO
WIPO (PCT)
Prior art keywords
composition
crystals
grinding
xylitol
sorbitol
Prior art date
Application number
PCT/FI1995/000490
Other languages
English (en)
Inventor
Juha Nurmi
Heikki Heikkilä
Helena Halttunen
Paula Perkkalainen
Ilkka Pitkänen
Original Assignee
Xyrofin Oy
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 Xyrofin Oy filed Critical Xyrofin Oy
Publication of WO1996007331A1 publication Critical patent/WO1996007331A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/06—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing beet sugar or cane sugar if specifically mentioned or containing other carbohydrates, e.g. starches, gums, alcohol sugar, polysaccharides, dextrin or containing high or low amount of carbohydrate

Definitions

  • Composition comprising co-crystals, method for its manufacture, and its use
  • the present invention relates to compositions comprising co-crystals of at least two compounds, prepared by grinding.
  • the compounds forming these co- crystals comprised in the composition of the invention are selected from a group consisting of monosaccharides, disaccharides and oligosaccharides and physiologically acceptable polyols.
  • the invention also relates to a method for producing such a composition, in which at least two crystalline compounds selected from mono ⁇ saccharides, disaccharides and oligosaccharides and physiologically acceptable polyols are ground as a mix- ture in a solid state at a temperature substantially lower than the melting points of the components.
  • Co-crystals are crystals formed by two or more compounds.
  • a co-crystal has a unique crystal structure, which is different from the crystal structure of its components.
  • a physiologically acceptable polyol in this context means a hydrogenated product corresponding to a monosaccharide, disaccharide or oligosaccharide, i.e. a sugar alcohol.
  • the compounds from which co-crystals have been prepared in the study concerned are substituted benzoic acid derivatives wherefrom co- crystals have been obtained both by crystallization from a solution and by grinding.
  • co- crystals can be produced from sugars and sugar alcohols by grinding also in cases where crystallization from a solution will not produce co-crystals, but the compounds are separable in a pure form by crystallization from the solution.
  • particulate, i.e. powdery or granular, products having sugars and sugar alcohols as raw mater ⁇ ials have been developed for the needs of the sweets and tableting industries.
  • Granular products in which the sugar or sugar alcohol is agglomerated with the aid of a binder and which are suitable for preparing tablets by the direct compression method are described for example in Finnish Patent 81 004 (xylitol with polyol as a binder), Finnish Patent Application 892797 (fructose with polyol as a binder) and Finnish Patent Application 932696 (xylitol with polymerized reducing sugar, alkali metal carboxymethyl cellulose or hydrogenated starch hydrolysate as a binder).
  • the main component of the product is granulated by adding thereto an aqueous solution of a binder, and after granulation the product is dried and possibly sifted.
  • U.S. Patent 5 158 789 relates to a sorbitol/xyl- itol co-crystal produced by melt crystallization.
  • the co-crystal is produced by melting the starting materials into a homogeneous melt, cooling the melt with simultaneous stirring until a viscous mass has been obtained, and slowly cooling this mass until the sorbitol/xylitol mixture is crystal ⁇ lized throughout.
  • the resultant co-crystal product is reported to be easier to tablet and to compound into chewing-gum, and also easier to handle in the sweets industry and/or in pharmaceutical compositions, to make use of the advantageous effects of xylitol.
  • the method for preparing co-crystals as disclosed in this patent publication is, however, expensive and slow and requires high temperatures in the melting step. Furthermore, the crystallized solid mass must be crushed and possibly ground as a last step to make it usable.
  • the product thus prepared by melting crystallization is an agglomer ⁇ ate in its physical properties. It is composed of numerous microcrystals adhering together.
  • U.S. Patent 5 075 291 discloses a similar method for preparing a pharmaceutical composition, the com ⁇ position comprising a crystalline sugar alcohol derived from at least one monosaccharide or polysaccharide and having particles of at least one pharmaceutically active compound homogeneously dispersed in its crystal matrix.
  • the product in accordance with this patent comprises 5-35% by weight of mannitol.
  • the starting materials are melted, stirred, the slightly cooled mass is extruded and allowed to cool for several days at room temperature and ground.
  • Finnish Patent Application 915876 relates to a directly compressible powdery composition based on xyl ⁇ itol.
  • Xylitol is stated to be present in an amount of at least 60% by weight of the composition, and possible other components of the composition include a sacchar- ide, oligosaccharide or polysaccharide or a correspond- ing hydrogenated compound thereof.
  • the process disclosed comprises thermomechanical treatment in which the start ⁇ ing material mixture partly melts and is extruded.
  • the residence time in the heat zone is 5-300 seconds, and the extruded partly molten mass is cooled, crushed and sifted; the particle size of the resultant product is in excess of 50 ⁇ , typically in excess of 100 ⁇ m.
  • a substantially dry composition in accordance with the invention which comprises co-crystals formed by at least two compounds selected from monosaccharides, disaccharides and oligo- saccharides and physiologically acceptable polyols, said co-crystals being produced by grinding a mixture of crystalline starting materials in a solid state.
  • the expression "substantially dry” in this con ⁇ text means that the amount of free water is less than about 5% by weight, preferably less than 1% by weight.
  • the invention also relates to a method for form ⁇ ing co-crystals from at least two compounds selected from monosaccharides, disaccharides and oligosaccharides and physiologically acceptable polyols, the method being characterized in that a mixture of crystalline starting materials is ground in a solid state at a temperature substantially lower than the melting points of the com ⁇ ponents until a fine product consisting of co-crystals is produced.
  • the grinding temperature in the method of the invention is not critical, as long as it is substan ⁇ tially lower than the melting point of any of the com ⁇ ponents in the mixture.
  • a grinding temper ⁇ ature suitable for a mixture of xylitol and sorbitol is in the range 15-50 °C. As a rule, the grinding is prefer ⁇ ably carried out at room temperature.
  • the invention is based on the finding that co- crystals can be obtained from compounds of the above type by grinding a mixture of starting materials in a solid state, provided that the melting points of the starting materials are sufficiently close to one an ⁇ other.
  • the difference between melting points should normally be less than about 30 °C, preferably less than 20 °C.
  • Monosaccharides, disaccharides and oligosacchar ⁇ ides that are possible in the preparation of the product of the invention include glucose, fructose, galactose, xylose, sucrose, mannose, lactose, maltose, isomaltose and raffinose.
  • the physiologically acceptable polyol(s) can be selected for instance from the following; sor ⁇ bitol, xylitol, maltitol, lactitol, mannitol, galactitol and isomalt.
  • the co-crystals are formed of sorbitol and xylitol, in which case the product is also suitable for diabetics and the special advantages of xylitol are also gained for example in regard to caries prevention.
  • Formation of a xylitol/sorbitol co-crystal by the method of the invention is particularly unexpected for the reason that the generally employed method for purifying xylitol from sorbitol is to crystallize it from an aque ⁇ ous solution containing these compounds, that is, such co-crystals are not formed from an aqueous solution. This completely deviates from what is to be anticipated on the basis of the above dissertation by G. M. Franken- bach.
  • the proximity of the melting points referred to above must be taken into account in the selection of the starting materials.
  • grinding did not produce co- crystals from a mannitol/sorbitol mixture (difference between melting points about 65 °C) or from a mannitol/ xylitol mixture (difference between melting points about 70 °C).
  • the grinding is carried out in a pulverizer wherein a large amount of energy is bound to the material to be ground and the particles are in intimate contact with one another for relatively long periods of time; the comminuting being based mainly on abrasion (rather than compression, impact or prall).
  • Suitable grinding devices include rod mills, ball mills and tube mills.
  • the composi- tion of the invention comprises 5-100% of co-crystals.
  • the product obtained by grinding may also include pure starting materials. If, for example, a mixture of sor ⁇ bitol and xylitol having 20 molar per cent of sorbitol and a balance of xylitol is ground, a product can be obtained in which all sorbitol is co-crystallized with an amount of xylitol corresponding to the co-crystal form, and thus the product comprises both co-crystals and free xylitol.
  • Co-crystallization of xylitol and sorbitol will take place at least at a molar ratio about 1:1, which in the above case will yield a product comprising 40% of co-crystals, the remainder being xylitol.
  • a powdery co- crystallized product is directly obtained from the crys- talline starting materials by grinding.
  • the particle size of the product is below 50 ⁇ m.
  • the product can be used as such for instance for tableting and as a raw material for the sweets industry, or it may be agglomerated into granules by methods known in the art, possibly employing binders as an aid in the agglomeration.
  • the scope of the present invention encompasses a product obtained by co-crystallization grinding and also granules obtained therefrom by agglomeration, as well as the use thereof in the preparation of pharmaceutical products, sweets and chewing-gum, and in the food industry, for instance in bakery products.
  • composition of the invention may also com ⁇ prise additives incorporated into the starting material mixture to be ground or into the product obtained from the grinding step or in connection with the agglomer ⁇ ation.
  • additives may be e.g. aromas and dyes, poly- dextrose, inulin, carboxymethyl cellulose etc.
  • Sugar alcohol mixtures xylitol/D-sorbitol, xyl- itol/D-mannitol and D-mannitol/D-sorbitol were prepared by weighing these reagents into each mixture in given molar ratios.
  • the reagents employed were: D-sorbitol, Fluka art. 85532, D-(-)-mannitol, Merck art. 5982, and xylitol by Cultor Ltd, the purity of which was ascer ⁇ tained.
  • the phases of the reagents and their thermal properties were measured prior to and after grinding by DSC and X-ray diffraction methods.
  • the D-(-)-mannitol by Merck was in the monoclinic 6-form
  • the D-sorbitol by Fluka was a mixture of A and r-polymorphs.
  • the mixtures of crystalline reagents were ground in a ball mill pulverizer FRITSCH Pulverizette type 07.302 with a speed setting 8-9 (scale 1-10) for 20 minutes.
  • TG Thermogravimetric
  • DSC differential scanning calorimetric
  • X-ray diffraction analyses were performed on each sample.
  • HP Plotter 7475A, PE DSC7 (software). The TG analyses were performed in platinum crucibles in an air flow, flow rate 40-60 cm 3 /min. The samples weighed 3 to 9 mg, the heating rate was 2 °C/ min, and the temperature range was 25-200 °C.
  • the DSC analyses were performed in 50 ⁇ l perforated aluminium crucibles in nitrogen flow, flow rate 50-60 cm 3 /min.
  • the samples weighed 3 to 9 g, the heating rate was 2 °C/min, and the temperature range was varied from the range 25-120 °C to the range 25-180 °C in accordance with the sample.
  • the X-ray diffraction patterns were measured with the ENRAF NONIUS PDS120 diffractometer furnished with an INEL CPS120 detector.
  • the radiation applied was mono ⁇ chromatic CuK ⁇ x radiation (wavelength 1.54056A).
  • the samples did not contain any appreciable amounts of moisture.
  • the "onset" and peak values for melting and the heats of fusion were measured from pure starting materials and ground pure starting materials by DSC.
  • the mean values and their standard deviations from two analyses are shown in Table 1 (standard deviation values in paren ⁇ theses).
  • the polymorphic forms of the starting materials were determined by DSC and X-ray diffraction.
  • the melting points of the starting materials employed were as follows: xylitol 93.0 °C, D-sorbitol 97.0 °C and D-mannitol 164.4 °C.
  • phase diagrams for the xylitol/D-mannitol, D- mannitol/D-sorbitol and xylitol/D-sorbitol systems were drawn up by using the melting peak values obtained from the DSC graphs, and they are shown in Figures 1, 2 and 3 in which
  • Figure 1 is a phase diagram for the system xyl ⁇ itol/D-mannitol
  • Figure 2 is a phase diagram for the system D- mannitol/D-sorbitol
  • Figure 3 is a phase diagram for the system xylitol/D-sorbitol.
  • the horizontal line shown in Figure 3 is the mean value of the melting points of the xylitol/D-sorbitol co-crystals in the zone 0.25/0.75-0.75/0.25 of the molar ratios (xylitol/D-sorbitol) of the co-crystal.
  • xylitol/D- mannitol and D-sorbitol/D-mannitol showed no signs of co-crystal formation in the solid state.
  • the melting point for the sugar alcohol having the lower melting point (xylitol and D-sorbitol, respectively) changed only very little when a sugar alcohol having a higher melting point (D-mannitol) was present.
  • the melting point of D-mannitol decreased when the molar ratio of xylitol or D-sorbitol, respectively, increased, in which situation xylitol and D-sorbitol were present as im ⁇ purities in D-mannitol.
  • the total heats of fusion of the melting process as measured for these samples were equi- valent to the values calculated from the heats of fusion of pure samples when the molar ratios of the samples were taken into account.
  • the DSC graphs determined for samples in which the starting materials had been separ ⁇ ately ground and thereafter mixed were equivalent to the DSC graphs for samples in which the starting materials had been ground together.
  • phase diagram for the xylitol/D-sorbitol sys- tem differed from the phase diagrams of the two previous systems. It complied with the shape of the phase dia ⁇ grams of two such components as do not form solid solu ⁇ tions with one another. However, the DSC patterns showed no characteristic configuration of eutectic melting, which would have been perceived as a sharp melting peak in the DSC graph.
  • the DSC graphs that were measured from samples in which the starting materials had been separ ⁇ ately ground and thereafter mixed differed from the DSC curves of samples in which the starting materials had been ground together.
  • Figure 4 shows the normalized DSC curves of xyl- itol/sorbitol mixtures for a case where the starting materials have been ground separately and for a case where they have been ground together.
  • the intersection of the two lines gives 76.2 °C as the melting point for the co-crystal of these compounds and 0.495/0.505 as the molar ratio (xyl ⁇ itol/D-sorbitol) thereof.
  • the mean value and standard deviation for the melting peak values calculated for molar ratios 0.25/0.75 and 0.75/0.25 was 76.1 (0.3) °C.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nutrition Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une composition sèche comprenant des cristaux combinés. On prépare ces derniers par broyage d'un mélange comprenant au moins deux composés cristallins sélectionnés parmi des monosaccharides, des disaccharides et des oligosaccharides, ainsi que des polyols physiologiquement acceptables à l'état solide. L'invention concerne également un procédé de préparation de ladite composition. On peut utiliser celle-ci dans la préparation de produits pharmaceutiques, de bonbons et de gommes à mâcher, ainsi que dans l'industrie alimentaire, par exemple dans des produits de boulangerie.
PCT/FI1995/000490 1994-09-09 1995-09-08 Compositions comprenant des cristaux combines, son procede de preparation et son utilisation WO1996007331A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI944182A FI944182A (fi) 1994-09-09 1994-09-09 Yhtenäiskiteitä sisältävä koostumus, menetelmä sen valmistamiseksi ja sen käyttö
FI944182 1994-09-09

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2888129A1 (fr) * 2005-07-08 2007-01-12 Roquette Freres Procede de production d'une poudre contenant des particules cristallines de xylitol avec un autre polyol
EP1842436A1 (fr) * 2005-01-24 2007-10-10 Nikken Fine Chemical Co., Ltd. Eutectique d'alcools de sucres et procede pour la produire
WO2007144683A1 (fr) * 2006-06-13 2007-12-21 Ingenio Del Cauca S.A. - Incauca S.A. Processus de co-cristallisation de saccharose avec un édulcorant naturel et produit ainsi obtenu
WO2008153945A2 (fr) * 2007-06-06 2008-12-18 University Of South Florida Compositions nutraceutiques de co-cristal
WO2010013035A1 (fr) * 2008-07-26 2010-02-04 University Of Bradford Procédé et produit
US7790905B2 (en) 2002-02-15 2010-09-07 Mcneil-Ppc, Inc. Pharmaceutical propylene glycol solvate compositions
US7927613B2 (en) 2002-02-15 2011-04-19 University Of South Florida Pharmaceutical co-crystal compositions
US8183290B2 (en) 2002-12-30 2012-05-22 Mcneil-Ppc, Inc. Pharmaceutically acceptable propylene glycol solvate of naproxen
CN101717325B (zh) * 2009-11-25 2012-12-05 山东蜜福堂食品有限公司 一种共晶体木糖醇的制备方法
US8362062B2 (en) 2002-02-15 2013-01-29 Mcneil-Ppc, Inc. Pharmaceutical compositions with improved dissolution
WO2014031162A1 (fr) * 2012-08-20 2014-02-27 Forest Laboratories Holdings Limited Forme cristalline de dérivés de carbamoyl-cyclohexane
US10501817B2 (en) 2010-03-16 2019-12-10 Imperial Sugar Company Process for the manufacture of co-crystallized sucrose natural sweeteners and the products thereof
US10633344B2 (en) 2002-03-01 2020-04-28 University Of South Florida Multiple-component solid phases containing at least one active pharmaceutical ingredient

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528604A1 (fr) * 1991-08-09 1993-02-24 SPI POLYOLS, Inc. Compositions sorbitol/xylitol cocristallisées à partir de la phase fondue
WO1994021827A1 (fr) * 1993-03-19 1994-09-29 Xyrofin Oy Agent edulcorant, son procede de production et son application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528604A1 (fr) * 1991-08-09 1993-02-24 SPI POLYOLS, Inc. Compositions sorbitol/xylitol cocristallisées à partir de la phase fondue
WO1994021827A1 (fr) * 1993-03-19 1994-09-29 Xyrofin Oy Agent edulcorant, son procede de production et son application

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7790905B2 (en) 2002-02-15 2010-09-07 Mcneil-Ppc, Inc. Pharmaceutical propylene glycol solvate compositions
US8362062B2 (en) 2002-02-15 2013-01-29 Mcneil-Ppc, Inc. Pharmaceutical compositions with improved dissolution
US7927613B2 (en) 2002-02-15 2011-04-19 University Of South Florida Pharmaceutical co-crystal compositions
US10633344B2 (en) 2002-03-01 2020-04-28 University Of South Florida Multiple-component solid phases containing at least one active pharmaceutical ingredient
US8183290B2 (en) 2002-12-30 2012-05-22 Mcneil-Ppc, Inc. Pharmaceutically acceptable propylene glycol solvate of naproxen
EP1842436A4 (fr) * 2005-01-24 2014-02-19 Food Science Co Ltd B Eutectique d'alcools de sucres et procede pour la produire
EP1842436A1 (fr) * 2005-01-24 2007-10-10 Nikken Fine Chemical Co., Ltd. Eutectique d'alcools de sucres et procede pour la produire
US8112935B2 (en) 2005-07-08 2012-02-14 Roquette Freres Method for producing a powder containing xylitol crystal particles with another polyol
WO2007006885A3 (fr) * 2005-07-08 2007-03-29 Roquette Freres Procede de production d'une poudre contenant des particules cristallines de xylitol avec un autre polyol
WO2007006885A2 (fr) * 2005-07-08 2007-01-18 Roquette Freres Procede de production d'une poudre contenant des particules cristallines de xylitol avec un autre polyol
FR2888129A1 (fr) * 2005-07-08 2007-01-12 Roquette Freres Procede de production d'une poudre contenant des particules cristallines de xylitol avec un autre polyol
US20140154359A1 (en) * 2006-06-13 2014-06-05 Ingenio Del Cauca S.A. -Incauca S.A. Process for co-crystallizing sucrose and a natural sweetener and the product thereof
WO2007144683A1 (fr) * 2006-06-13 2007-12-21 Ingenio Del Cauca S.A. - Incauca S.A. Processus de co-cristallisation de saccharose avec un édulcorant naturel et produit ainsi obtenu
US8404297B2 (en) 2006-06-13 2013-03-26 Ingenio del Cauca S.A.—Incauca S.A. Process for co-crystallizing sucrose and a natural sweetener and the product thereof
WO2008153945A2 (fr) * 2007-06-06 2008-12-18 University Of South Florida Compositions nutraceutiques de co-cristal
US10376521B2 (en) 2007-06-06 2019-08-13 University Of South Florida Nutraceutical co-crystal compositions
WO2008153945A3 (fr) * 2007-06-06 2009-02-12 Univ South Florida Compositions nutraceutiques de co-cristal
US10842797B2 (en) 2007-06-06 2020-11-24 University Of South Florida Nutraceutical co-crystal compositions
WO2010013035A1 (fr) * 2008-07-26 2010-02-04 University Of Bradford Procédé et produit
CN101717325B (zh) * 2009-11-25 2012-12-05 山东蜜福堂食品有限公司 一种共晶体木糖醇的制备方法
US10501817B2 (en) 2010-03-16 2019-12-10 Imperial Sugar Company Process for the manufacture of co-crystallized sucrose natural sweeteners and the products thereof
WO2014031162A1 (fr) * 2012-08-20 2014-02-27 Forest Laboratories Holdings Limited Forme cristalline de dérivés de carbamoyl-cyclohexane

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Publication number Publication date
FI944182A0 (fi) 1994-09-09
FI944182A (fi) 1996-03-10

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