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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants.
Synonyms: D(-)-Fructose; Fruit sugar; D-arabino-hexulose
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Search for reports by entering the product batch number.
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CAS No. : | 57-48-7 |
Formula : | C6H12O6 |
M.W : | 180.16 |
SMILES Code : | [H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)CO |
Synonyms : |
D(-)-Fructose; Fruit sugar; D-arabino-hexulose
|
MDL No. : | MFCD00148910 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.89 %Chromat. | With Aspergillus flavus NFCCI 2364 culture filtrate In aq. buffer at 55℃; for 24 h; Microbiological reaction | General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50percent (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55°C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414). |
25.31 %Chromat. | With Aspergillus niger SI 19 culture filtrate In aq. buffer at 55℃; for 24 h; Microbiological reaction | General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50percent (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55°C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water;phosphoric acid; at 50 - 95℃; for 0.25 - 0.75h;pH 1.75 - 3.75; | Figure 4, from a second laboratorial work, is a TLC - Thin Layer Chromatography on silicagel 60 (Merck) developed with the mixture isopropanol : ethyl acetate : water 5:1 :2 as mobile phase and with partial runs of 1/3, 2/3, and 3/3 of the front line and developed with orcinol : sulfuric acid : methanol at 1000C for 5 minutes. This figure illustrates the profile of FOS - Fructooligosaccharides when one hydrolyzes purified inulin from dahlia roots (5g%) with phosphoric acid at pH = 2.5 at 850C during 15 minutes (15), 30 minutes (30), and 45 minutes (45), indicating that the modulation of a single kinetic parameter - time of hydrolysis - already allows to govern the quantitative relation of FOS > fructose (cases 15 and 30) or the opposite (FOS < fructose; 45). A similar strategy for FOS > fructose may also be governed by the other parameters (pH itself or temperature of hydrolysis), as shown for hydrolysis of inulin with phosphoric or citric acids at pHs from 1.75 to 3.75 in the range of 5O0C to 95oC (as better explained in Figure 5). In Figure 4, (f) and (g) denotes for free fructose and glucose, respectively. GP refers to the Degree of Polymerization. It is remarkable that phosphoric or citric hydrolyses of inulin may be effectively addressed <n="27"/>to the preferential preparation of FOS - Fructooligosaccharides since when addressed to a higher fructose content (lane 45), some amount of the co-product HMF - hydroxymethylfurfural turns clearly visible in the front zone of the chromatogram. Its companion spot most probably is a DFA (difructose anhydride).; Figure 5 is a bar graphic comparing the effect of the kinetic parameters such as temperature and time of hydrolysis once fixed the hidrogenionic potential at pH = 2.5 and their respective capacities for the modulation on the qualitative nature of the products from the hydrolyses of dahlia inulin with phosphoric or citric acids when the substrate is used at a concentration of 5g%. According to the intended innovation in this patent request - the preferential production of FOS or FrutoOligoSaccharides - is obviously that, for each range of temperature, namely, 750C, 850C ou 950C, either in the phosphoric or in the citric hydrolyses, the formation of FOS is preferential in (8x2 =) 16 assays, except for those two - at 950C and during 25 minutes - where fructose shows predominance with respect to FOS. Incidentally, those two exceptional conditions - which are not the scope of this patent request - also led to the formation of some HMF - hydroxymethylfurfural - undesirable in a inulin hydrolysis, with the attenuating condition that a less expensive practice as activated charcoal is able to remove the contaminant HMF. Concerning the reaction yield reported to the initial inulin input, the diluted phosphoric acid guarantees in the times of 25 min at 850C and of 15 min at 950C percentages of hydrolyses up to 80%, being the most of the products - 76% and 63%, respectively - FOS or frutooligosaccharides and being the remaining fructose since HMF is no longer detected under these conditions of hydrolysis. The same approach is attained with citric acid although with somewhat reduced yields - 64% or 76%, but even so FOS correspond to 78% and 74% of the hydrolysis products.; Figure 6 derives from another practical example of laboratory work, namely a high performance liquid chromatography or HPLC in a column of 10 micra microparticles of silica gel derivatized with amino groups and provided by Spectraphysics. Twenty microliters of a citric hydrolyzate of inulin at 10% obtained at pH 2.5 during 5 or 15 minutes at 850C were applied to the column and elution proceeded with 70% acetonitrile at a 1 mL/min flow rate and the monitoring was carried out with DRI- differential refraction index. It is shown that in both conditions <n="28"/>- 5 and 15 minutes - inulin is converted, by citric acid, into a family of FOS - FructoOligoSaccharides with DP - Degree of Polymerization - 3 to 18 or more (considering the analytical capacity of the referred column), still emphazing that fructose, with respect to FOS concentration, contributes with a maximum of 25% and a minimum of 5%.; Figure 7, resulting from another practical laboratory work, is also - like Figure 6 - a HPLC but carried out with samples arising from phosphoric acid hydrolyses under the same conditions of those described in Figure 6. The qualitative profiles for FOS are quite similar in both figures. In 8 of 9 assays, FOS predominates. In the nineth - 25 minutes of hydrolysis at higher temperature - FOS and fructose contents are more or less equivalent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water;citric acid; at 50 - 95℃; for 0.25 - 0.75h;pH 1.75 - 3.75; | Figure 4, from a second laboratorial work, is a TLC - Thin Layer Chromatography on silicagel 60 (Merck) developed with the mixture isopropanol : ethyl acetate : water 5:1 :2 as mobile phase and with partial runs of 1/3, 2/3, and 3/3 of the front line and developed with orcinol : sulfuric acid : methanol at 1000C for 5 minutes. This figure illustrates the profile of FOS - Fructooligosaccharides when one hydrolyzes purified inulin from dahlia roots (5g%) with phosphoric acid at pH = 2.5 at 850C during 15 minutes (15), 30 minutes (30), and 45 minutes (45), indicating that the modulation of a single kinetic parameter - time of hydrolysis - already allows to govern the quantitative relation of FOS > fructose (cases 15 and 30) or the opposite (FOS < fructose; 45). A similar strategy for FOS > fructose may also be governed by the other parameters (pH itself or temperature of hydrolysis), as shown for hydrolysis of inulin with phosphoric or citric acids at pHs from 1.75 to 3.75 in the range of 5O0C to 95oC (as better explained in Figure 5). In Figure 4, (f) and (g) denotes for free fructose and glucose, respectively. GP refers to the Degree of Polymerization. It is remarkable that phosphoric or citric hydrolyses of inulin may be effectively addressed <n="27"/>to the preferential preparation of FOS - Fructooligosaccharides since when addressed to a higher fructose content (lane 45), some amount of the co-product HMF - hydroxymethylfurfural turns clearly visible in the front zone of the chromatogram. Its companion spot most probably is a DFA (difructose anhydride).; Figure 5 is a bar graphic comparing the effect of the kinetic parameters such as temperature and time of hydrolysis once fixed the hidrogenionic potential at pH = 2.5 and their respective capacities for the modulation on the qualitative nature of the products from the hydrolyses of dahlia inulin with phosphoric or citric acids when the substrate is used at a concentration of 5g%. According to the intended innovation in this patent request - the preferential production of FOS or FrutoOligoSaccharides - is obviously that, for each range of temperature, namely, 750C, 850C ou 950C, either in the phosphoric or in the citric hydrolyses, the formation of FOS is preferential in (8x2 =) 16 assays, except for those two - at 950C and during 25 minutes - where fructose shows predominance with respect to FOS. Incidentally, those two exceptional conditions - which are not the scope of this patent request - also led to the formation of some HMF - hydroxymethylfurfural - undesirable in a inulin hydrolysis, with the attenuating condition that a less expensive practice as activated charcoal is able to remove the contaminant HMF. Concerning the reaction yield reported to the initial inulin input, the diluted phosphoric acid guarantees in the times of 25 min at 850C and of 15 min at 950C percentages of hydrolyses up to 80%, being the most of the products - 76% and 63%, respectively - FOS or frutooligosaccharides and being the remaining fructose since HMF is no longer detected under these conditions of hydrolysis. The same approach is attained with citric acid although with somewhat reduced yields - 64% or 76%, but even so FOS correspond to 78% and 74% of the hydrolysis products.; Figure 6 derives from another practical example of laboratory work, namely a high performance liquid chromatography or HPLC in a column of 10 micra microparticles of silica gel derivatized with amino groups and provided by Spectraphysics. Twenty microliters of a citric hydrolyzate of inulin at 10% obtained at pH 2.5 during 5 or 15 minutes at 850C were applied to the column and elution proceeded with 70% acetonitrile at a 1 mL/min flow rate and the monitoring was carried out with DRI- differential refraction index. It is shown that in both conditions <n="28"/>- 5 and 15 minutes - inulin is converted, by citric acid, into a family of FOS - FructoOligoSaccharides with DP - Degree of Polymerization - 3 to 18 or more (considering the analytical capacity of the referred column), still emphazing that fructose, with respect to FOS concentration, contributes with a maximum of 25% and a minimum of 5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.25%Chromat.; 29.89%Chromat.; 25.26%Chromat. | With Aspergillus flavus NFCCI 2364 culture filtrate; In aq. buffer; at 55℃; for 24h;pH 5.5;Microbiological reaction; | General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50% (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414). |
5.94%Chromat.; 23.74%Chromat.; 25.31%Chromat. | With Aspergillus niger SI 19 culture filtrate; In aq. buffer; at 55℃; for 24h;pH 5.5;Microbiological reaction; | General procedure: FOS production was carried out by adding 1ml of enzyme samples collected at various time intervals to 3ml of 50% (w/v) sucrose dissolved in 0.1M citrate buffer (pH 5.5) for period of 24h at 55C. The amount of FOS formation in the samples was analyzed by high performance liquid chromatography (HPLC, Waters) with sugar-pak column (6.5×300mm) and refractive index (RI) differential detector (RI 2414). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Viscozyme L (-fructosyltransferase) immobilized on chitosan spheres; In aq. acetate buffer; at 50℃;pH 4.5;Flow reactor; | Production of invert sugar was carried using a solution of sucrose150 g/L diluted in 50 mM sodium acetate buffer pH 4.5. The solu-tion was pumped at flow rates of (0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0,4.7) mL/min in both fluidized and packed bed reactors. Four bed vol-umes of solution were passed through the column before taking the sample to achieve stationary state. These experiments were carriedout in duplicate, changing the column bed at each experiment |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With FAD; Escherichia coli L-rhamnulose-1-phosphate aldolase; Streptococcus pneumonia glycerol phosphate oxidase; In water-d2; at 30℃; for 22h;pH 7;Enzymatic reaction; | General procedure: To a solution of DL-glycerol 3-phosphate magnesium salt (548.78 mg, 2.4 mmol) in 6.86 mL ddH2O was added <strong>[497-09-6]D-glyceraldehyde</strong> (or L-glyceraldehyde) (2 mL, 0.5 M, 1.0 mmol) at pH 7.0, glycerol phosphate oxidase saturated with FAD (final concentration 0.2 mg/mL), catalase (1000 U, 1.18 muL) and aldolase (final concentration 0.5 mg/mL). ddH2O was added to bring the total volume to 10 mL if necessary. The reaction mixture was shaken at 30 °C for 22 h and the reaction was monitored by TLC (developed by nBuOH/AcOH/H2O 2/1/1 (v/v/v) and stained with anisaldehyde sugar stain). The pH was then adjusted to pH ~5 with 6 N HCl and 11 muL acid phosphatase (18 U) was added and the mixture was shaken at 37 °C for 24 h. After cooling to rt., the pH was adjusted to 7.0 with 1 N NaOH and the mixture was diluted with methanol. The solution was filtered through Celite and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/iPrOH/H2O 9/3/1 (v/v/v)) to afford a pale yellow syrup which was further purified by Bio gel P-2 column. The mixture of monosaccharides could be isolated by Ca2+ exchange resin column. The purification process using P-2 column or Ca2+ exchange resin column was performed with the same procedure we previously used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With FAD; Thermus thermophilus HB8 L-fuculose-1-phosphate aldolase; Streptococcus pneumonia glycerol phosphate oxidase; In water-d2; at 30℃; for 22h;pH 7;Enzymatic reaction; | General procedure: To a solution of DL-glycerol 3-phosphate magnesium salt (548.78 mg, 2.4 mmol) in 6.86 mL ddH2O was added <strong>[497-09-6]D-glyceraldehyde</strong> (or L-glyceraldehyde) (2 mL, 0.5 M, 1.0 mmol) at pH 7.0, glycerol phosphate oxidase saturated with FAD (final concentration 0.2 mg/mL), catalase (1000 U, 1.18 muL) and aldolase (final concentration 0.5 mg/mL). ddH2O was added to bring the total volume to 10 mL if necessary. The reaction mixture was shaken at 30 °C for 22 h and the reaction was monitored by TLC (developed by nBuOH/AcOH/H2O 2/1/1 (v/v/v) and stained with anisaldehyde sugar stain). The pH was then adjusted to pH ~5 with 6 N HCl and 11 muL acid phosphatase (18 U) was added and the mixture was shaken at 37 °C for 24 h. After cooling to rt., the pH was adjusted to 7.0 with 1 N NaOH and the mixture was diluted with methanol. The solution was filtered through Celite and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/iPrOH/H2O 9/3/1 (v/v/v)) to afford a pale yellow syrup which was further purified by Bio gel P-2 column. The mixture of monosaccharides could be isolated by Ca2+ exchange resin column. The purification process using P-2 column or Ca2+ exchange resin column was performed with the same procedure we previously used. |
Tags: 57-48-7 synthesis path| 57-48-7 SDS| 57-48-7 COA| 57-48-7 purity| 57-48-7 application| 57-48-7 NMR| 57-48-7 COA| 57-48-7 structure
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H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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