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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.
Lactitol is a gastrointestinal agent.
Synonyms: D-Lactitol
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 585-86-4 |
| Formula : | C12H24O11 |
| M.W : | 344.31 |
| SMILES Code : | OC[C@H](O)[C@@H](O)[C@H](O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)[C@H](O)CO |
| Synonyms : |
D-Lactitol
|
| English Name : | (2S,3R,4R,5R)-4-(((2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexane-1,2,3,5,6-pentaol |
| MDL No. : | MFCD00079407 |
| GHS Pictogram: | |
| Signal Word: | |
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| Precautionary Statements: | |
| Class: | |
| UN#: | |
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* 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 |
|---|---|---|
| With hydrogen In water at 60 - 120℃; for 0 - 4.5h; | 2; 4A; 4B; 8B; 9 Example 2; The effect of sequential temperature adjustments (temperature ramping); A lactose solution was prepared in the same way as in Example 1. The equipment used for the hydrogenation as well as the hydrogenation pressure, the mixing rate, the catalyst and the catalyst dosage in the hydrogenation were the same as in Example 1. Three consecutive batches were hydrogenated with the same catalyst without any regeneration of the catalyst in the same way as in Example 1.The hydrogenations were performed for 240 minutes. The temperature in the hydrogenation reactor was adjusted during the hydrogenation and varied in the tests as follows (in test 1 , the whole hydrogenation was carried out at the same final temperature, whereas in tests 2 to 5 the hydrogenation was started at a lower temperature and the temperature was then rised gradually to the final hydrogenation temperature):Test 1 : the whole reaction was carried out at 120 0C.Test 2: temperature ramping from 9O0C to 12O0C during the first 30 minutes of the reaction (1 C7min).Test 3: temperature ramping from 9O0C to 12O0C during the first 60 minutes (0.5 °C/min).Test 4: temperature ramping from 9O0C to 12O0C during the first 120 minutes (0.25°C/min).Test 5: temperature ramping from 6O0C to 12O0C during the first 120 minutes (0.5°C/min).The test results are shown in Figures 2 and 3. The results show the retarded and significantly lower production of lactobionic acid when the reaction was started at a lower temperature and the temperature was then rised slowly from 6O0C or 9O0C to 12O0C. Despite the lower temperature during the first part of the hydrogenation, a high conversion degree of lactose to lactitol was achieved at the end the hydrogenation reactions. The conversion in the first batch was 100% and in the third batch 95 to 98%. With recycled catalysts, the conversion was higher when temperature ramping was used compared to the reaction without temperature ramping.Furthermore, the following table 1 shows that temperature ramping clearly improved the hydrogenation selectivity.Table 1Lactitol selectivity at 99% conversion levelFurthermore, Figure 4 shows that temperature ramping significantly decreased leaching of nickel and aluminium from the catalyst compared to the test where the whole reaction was carried out at 12O0C.; Example 4A; The effect of the hydrogenation pressure on the hydrogenation of lactose; Lactose (manufactured by Leprino Foods) was dissolved in ion- exchanged water to obtain a lactose solution containing 40% lactose by weight. The hydrogenations were carried out at 12O0C at four different hydrogenation pressures (20, 35, 55 and 70 bar). The hydrogenation catalyst was a sponge nickel catalyst (manufactured by Acticat) and the catalyst load was 10% by weight (50% dry content).The hydrogenation results are shown in Figure 9A, 9B and 9C. Figure 9A shows the influence of the hydrogen pressure on lactose conversion as a function of the hydrogenation time. Figure 9B shows the influence of the hydrogen pressure on lactitol selectivity as a function of lactose conversion. Figure 9C shows the influence of the hydrogen pressure on the formation of lac- tobionic acid as a function of lactose conversion.The results of Figures 9A, 9B and 9C show that the formation of lac- tobionic acid formation increases during the lactose hydrogenation process, leading to decreased reaction rate and decreased lactitol selectivity, if the hydrogen pressure in the reactor is low.; Example 4B; The effect of sequential pressure adjustments (pressure ramping) on the formation of lactobionic acid in the hydrogenation of lactose to lactitol; A lactose solution was prepared in the same way as in Example 1. The equipment used for the hydrogenation and the catalyst were the same as in Example 1. The lactose solution was hydrogenated at a temperature of 12O0C and at a hydrogen pressure of 50 bar. The catalyst dosage was 10% by weight (50% by weight of the dry substance) of the initial lactose amount. Three consecutive hydrogenation batches were carried out with the same catalyst. Hydrogenations were performed for 240 minutes. The pressure in the hydrogenation reactor was adjusted during the hydrogenation to show how insufficient hydrogen pressure and insufficient amount of hydrogen on the catalyst surface affects the hydrogenation reaction. Three tests were carried out as follows:Test 1 : the whole reaction was carried out at 12O0C and at a hydrogen pressure of 50 bar. Test 2: temperature ramping from 9O0C to 12O0C at 50 bar during the first 30 minutes.Test 3: pressure ramping from 20 bar to 50 bar (1 bar/min) at 120 0C for the first 30 minutes.The test results are shown in Figure 9D. The results show the retarded conversion of lactose to lactitol when the pressure ramping from 20 bar to 50 bar during the first 30 minutes was in use. The effect was very similar when the temperature at the beginning of the hydrogenation reaction was rised gradually from 9O0C to 12O0C. However, the formation of lactobionic acid in the process with the pressure ramping was even higher than in the process where the pressure was 50 bar during the whole hydrogenation process and clearly higher than in the process where the temperature ramping was in use (Figure 10). The test results show that the formation of lactobionic acid will speed up when the hydrogen pressure is too low and the surface of the catalyst does not contain enough hydrogen.The test results in Figure 9 D also show that the use of temperature ramping improves conversion rate and the conversion of 90% in the third consecutive batch is achieved about 10% faster than without temperature ramping due to the lower formation of lactobionic acid.; Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-products; Further experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate.; Example 9; The effect of mixing on the hydrogenation of lactoseLactose (manufactured by Leprino Foods) was dissolved in ion- exchanged water to obtain a lactose solution containing 40% lactose by weight. The hydrogenations were carried out at 12O0C and at a hydrogen pressure of 50 bar with three different mixing rates (600, 900 and 1800 rpm). The catalyst and the catalyst load were the same as in Example 1.The hydrogenation results are shown in Figures 19, 20 and 21. Figure 19 shows the influence of the mixing rate on lactose conversion as a function of the hydrogenation time. Figure 20 shows the effect of the mixing rate on lactitol selectivity as a function of lactose conversion. Figure 21 shows the effect of the mixing rate on the formation of lactobionic acid as a function of lactose conversion.The results show that lactobionic acid formation increases during the lactose hydrogenation process, leading to decreased hydrogenation rate and decreased lactitol selectivity, if mixing in the hydrogenation reactor is inefficient. | |
| With sodium benzoate; hydrogen In water at 120℃; for 0 - 4h; | 8B Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-productsFurther experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate. | |
| With hydrogen; benzoic acid In water at 120℃; for 0 - 4h; | 8B Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-productsFurther experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate. |
| With formic acid; hydrogen In water at 120℃; for 0 - 4h; | 8B Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-productsFurther experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate. | |
| With hydrogen; citric acid In water at 120℃; for 0 - 4h; | 8B Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-productsFurther experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate. | |
| With hydrogen; acetic acid In water at 120℃; for 0 - 4h; | 8B Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-productsFurther experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate. | |
| With hydrogen; propionic acid In water at 120℃; for 0 - 4h; | 8B Example 8B; The effect of the addition of acetic acid and various other carboxylic acids on the formation of lactobionic acid and other by-productsFurther experiments were carried out by adding acetic acid as well as some other carboxylic acids and salts thereof (benzoic acid, sodium ben- zoate, formic acid and propionic acid) into the hydrogenation batch prior to the beginning of the hydrogenation. The hydrogenations were performed with sponge nickel catalyst in the same way as in Example 8A.The results are presented in Figures 14 to 18. Figure 14 shows the effect of the addition of benzoic acid and sodium benzoate on the formation of lactobionic acid as a function of the hydrogenation time. Figure 15 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of lactobionic acid as a function of the hydrogenation time. Figure 16 shows the effect of the addition of benzoic acid and sodium benzoate on the the formation of by-products as a function of the hydrogenation time. Figure 17 shows the effect of the addition of acetic acid, formic acid and propionic acid on the formation of by-products as a function of the hydrogenation time. Figure 18 shows the effect of the addition of acetic acid, citric acid and lactobionic acid on the conversion of lactose to lactitol.The results of Figures 14 to 17 show that the addition of benzoic acid, acetic acid, formic acid and propionic acid decrease the formation of lactobionic acid (Figures 14 and 15) and improve the product selectivity (Figures 16 and 17). Figure 18 shows that the addition of acetic acid does not significantly influence the hydrogenation rate, whereas the addition of citric acid and lactobionic acid significantly decreased the hydrogenation rate. |

Tags: Lactitol | D-Lactitol | Antibacterial | Natural Products-Other Structure | Anti-Infection | By Structure | 585-86-4
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| P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
| Code | Phrase |
| P401 | |
| P402 | Store in a dry place. |
| P403 | Store in a well-ventilated place. |
| P404 | Store in a closed container. |
| P405 | Store locked up. |
| P406 | Store in corrosive resistant/ container with a resistant inner liner. |
| P407 | Maintain air gap between stacks/pallets. |
| P410 | Protect from sunlight. |
| P411 | |
| P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
| P413 | |
| P420 | Store away from other materials. |
| P422 | |
| P402 + P404 | Store in a dry place. Store in a closed container. |
| P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
| P403 + P235 | Store in a well-ventilated place. Keep cool. |
| P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
| P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
| P411 + P235 | Keep cool. |
Disposal | |
| Code | Phrase |
| P501 | Dispose of contents/container to ... |
| P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
| Code | Phrase |
| H200 | Unstable explosive |
| H201 | Explosive; mass explosion hazard |
| H202 | Explosive; severe projection hazard |
| H203 | Explosive; fire, blast or projection hazard |
| H204 | Fire or projection hazard |
| H205 | May mass explode in fire |
| H220 | Extremely flammable gas |
| H221 | Flammable gas |
| H222 | Extremely flammable aerosol |
| H223 | Flammable aerosol |
| H224 | Extremely flammable liquid and vapour |
| H225 | Highly flammable liquid and vapour |
| H226 | Flammable liquid and vapour |
| H227 | Combustible liquid |
| H228 | Flammable solid |
| H229 | Pressurized container: may burst if heated |
| H230 | May react explosively even in the absence of air |
| H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
| H240 | Heating may cause an explosion |
| H241 | Heating may cause a fire or explosion |
| H242 | Heating may cause a fire |
| H250 | Catches fire spontaneously if exposed to air |
| H251 | Self-heating; may catch fire |
| H252 | Self-heating in large quantities; may catch fire |
| H260 | In contact with water releases flammable gases which may ignite spontaneously |
| H261 | In contact with water releases flammable gas |
| H270 | May cause or intensify fire; oxidizer |
| H271 | May cause fire or explosion; strong oxidizer |
| H272 | May intensify fire; oxidizer |
| H280 | Contains gas under pressure; may explode if heated |
| H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
| H290 | May be corrosive to metals |
Health hazards | |
| Code | Phrase |
| H300 | Fatal if swallowed |
| H301 | Toxic if swallowed |
| H302 | Harmful if swallowed |
| H303 | May be harmful if swallowed |
| H304 | May be fatal if swallowed and enters airways |
| H305 | May be harmful if swallowed and enters airways |
| H310 | Fatal in contact with skin |
| H311 | Toxic in contact with skin |
| H312 | Harmful in contact with skin |
| 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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