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CAS No. : | 5424-20-4 | MDL No. : | MFCD00066397 |
Formula : | C76H52O46 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LRBQNJMCXXYXIU-PPKXGCFTSA-N |
M.W : | 1701.20 | Pubchem ID : | 16129778 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P273-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335-H412 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
96.15 - 97.7% | In water; at 35 - 50℃; for 1h;Product distribution / selectivity; | EXAMPLE 1 <strong>[93-14-1]Guaifenesin</strong> tannate was prepared as follows. In a 1-liter beaker were placed 340 g tannic acid (0.2 m), 163 g water and 39.6 g (0.2 m) of <strong>[93-14-1]guaifenesin</strong>. The mixture was heated to a temperature of 35-50 C. and was stirred for 1 hour. After cooling to room temperature, the entire reaction mixture was freeze dried at a reduced pressure of 200-100 milliTorr and a temperature of -50 to -40 C. for about 36 hours. At this point, the water which had been removed was condensed and its weight equaled about 160 g. The yield of <strong>[93-14-1]guaifenesin</strong> tannate was 365 g (96.15% of theory). EXAMPLE 2 [00036] Example 1 was repeated using a <strong>[93-14-1]guaifenesin</strong>: tannic acid molar ratio of 2: 1. In a 1-liter beaker were placed 340 g tannic acid (0.2 m), 180 g water and 79.3 g (0.4 m) of <strong>[93-14-1]guaifenesin</strong>. The mixture was heated to a temperature of 35-50 C. and was stirred for 1 hour. After cooling to room temperature, the entire reaction mixture was freeze dried at a reduced pressure of 200-100 milliTorr and a temperature of -50 to -40 C. for about 36 hours. At this point the water which had been removed was condensed and its weight equaled about 176 g. The yield of <strong>[93-14-1]guaifenesin</strong> tannate was 405 g (96.6% of theory). EXAMPLE 3 [00037] Example 1 was repeated using a <strong>[93-14-1]guaifenesin</strong>: tannic acid molar ratio of 5: 1. In a 1-liter beaker were placed 340 g tannic acid (0.2 m), 230 g water and 198.2 g (1 m) of <strong>[93-14-1]guaifenesin</strong>. The mixture was heated to a temperature of 35-50 C. and was stirred for 1 hour. After cooling to room temperature, the entire reaction mixture was freeze dried at a reduced pressure of 200-100 milliTorr and a temperature of -50 to -40 C. for about 36 hours. At this point, the water which had been removed was condensed and its weight equaled about 220 g. The yield of <strong>[93-14-1]guaifenesin</strong> tannate (which had a wet appearance) was 526 g (97.7% of theory). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3 EXAMPLE 3 EXAMPLE 3 An aqueous tara extract solution having a tannin concentration of 20% (W/V) was prepared, and the insoluble materials were removed therefrom by filtration. The filtrate was adjusted to pH 7.9 with a 40% (W/V) aqueous sodium hydroxide solution, and 80 ml of the adjusted filtrate was placed in a 150-ml Erlenmeyer flask. After adding 5.04 g (final concentration: 0.75M) of sodium hydrogencarbonate, the resulting mixture was gently stirred over a magnetic stirrer at a temperature of 25° C. A 31% (W/V) aqueous hydrogen peroxide solution was added to the mixture at a constant rate over a period of 3 hours. During the reaction, the pH was maintained at 8.5 with a 40% (W/V) aqueous sodium hydroxide solution. The amount of the aqueous hydrogen peroxide solution used was 12.8 ml. | ||
4 Immobilisation of Tannin EXAMPLE 4 Immobilisation of Tannin 14 g Brewtan is dissolved in 250 ml demineralised water, and treated with NaOH 1 M to a pH of 9.5. Subsequently, 40 g of Daraclar 7500 based silica-spacer is then added, and the suspension is heated to 60° C. for 3 hours. After cooling, the product is collected on a pressure filter and washed with 10 times 100 ml demi water and dried. This yields 39.7 g of slightly brown product. Brewtan is a Chinese gallotannin with between 12 and 30 hydroxyl groups. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In hexane for 2h; | 10 0.5 g of Glatiramer acetate, 2 g of tannic acid and 35 ml hexane were mixed and stirred for 2 hours. The suspension was filtered (fast filtration) , and the solid product was dried at 35°C under vacuum to constant weight and ground in mortar.Yield of dry solid - 2.4 g, Assay of Glatiramer by HPLC 16.6% wt, Chemical yield 90% |
76% | In methanol for 0.25h; | 5 0.5 g Glatiramer acetate was dissolved in 20 ml methanol while stirred. A solution of 2.0 g of tannic acid in 10 ml methanol was added over 15 minutes. Precipitation of solids was observed during the addition. The suspension was stirred for one hour and settled. No solid sedimentation was observed. The solvent was distilled out under vacuum and the residue of evaporation (a brown semisolid mass) was mixed with 20 ml methanol. The resulting suspension was stirred and filtered. Filtered solid was washed with methanol and dried under vacuum at 35 °C to constant weight/ brownish powder material obtained.The yield of dry solid was 0.77 g. An assay of Glatiramer by HPLiC showed a yield of 41.4% by weight and a chemical yield of 76%. |
70% | With sodium chloride In water for 0.166667 - 2.25h; | 2; 3; 4; 6; 7; 8; 9 A 5% aqueous solution containing 2.1 g of glatiramer in the form of glatiramer acetate, with a pH of 5.5, was added to a 10% aqueous solution of tannic acid (USP grade) containing 3.85 g of tannic acid, with a pH of 3.2. 5.2 g of NaCl was added, in the form of 10% aqueous solution, and the suspension was stirred for 30 minutes. The suspension was centrifuged at 3000G for 22 minutes and the clear decantate was poured off.The solid sediment was washed with 80 ml of deionized water followed by 2 ml of 10% NaCl solution, and centrifuged at 3000G, and the clear decantate was poured off. The wet solid was dried under vacuum (25 mbar) at 40 "C. 4.3g of dried solid was attained, with a glatiramer content of 1.56 g (71% yield). The glatiramer content of the combined decantate was 0.64g.; A 5% aqueous solution containing 2.1 g of glatiramer in the form of glatiramer acetate with a pH of 5.5, was added to a 10% aqueous solution of tannic acid (USP grade) containing 6.0 g of tannic acid, with a pH of 3.2. 6.0 g of NaCl 10% aqueous solution was added, and the suspension was stirred for 2.25 hours. The suspension was filtered, and the solid cake was washed with aqueous 0.5% NaCl solution (31 g of solution) . The wet solid was dried under vacuum (25 mbar) at 40°C. 6.2g of dried solid was attained, with a glatiramer content of 1.9 g (86% yield) .The glatiramer content of the combined filtrate and wash was determined to be 0.3 g.; A 5% aqueous solution containing 2.1 g of glatiramer in the form of glatiramer acetate, with a pH of 5.5, was added to a 10% aqueous solution of tannic acid (USP grade) containing 10.0 g of tannic acid, with a pH of 3.2. 9.1g of 10% NaCl aqueous solution were added, and the suspension was stirred for 2.25 hours. The suspension was cooled to a temperature of 100C and filtered. The solid cake was washed with 8Og of 0.5% NaCl solution. The wet washed solid was dried under vacuum (25 mbar) at 400C. 8.1 g of dry solid in the form of brownish pellets were attained. The amount of acetate ion in the sample was determined by gas chromatography to be 0.1%.; 1 g of Glatiramer acetate, 19 ml of deionized water and 1.8ml of 10% NaCl were mixed. After stirring and complete dissolution of a solid solution of 4 g tannic acid in 36 ml deionized water was added. Precipitation of solid product took place during the addition. The suspension was stirred for 10 minutes and was allowed to settl for 5 minutes. Complete solid sedimentation was observed, liquor was decanted and 30ml methanol was added. The product was suspended in methanol by stirring and solvent was distilled out under vacuum. The solid residue was dried at 350C under vacuum to a constant weight and ground in mortar "Substance A" . The decanted liquor was evaporated under vacuum to dryness then the solid residue was ground in mortar "Substance B"."Substance A": Yield of dry solid - 3.7g, Assay of Glatiramer by HPLC 23.7% wt, Chemical yield 91%."Substance B": Yield of dry solid - 1.2g, Assay of Glatiramer by HPLC 7.2% wt.; 5 g Glatiramer acetate was dissolved in 95ml deionized water. After stirring and complete dissolution, a solution containing of 20 g tannic acid and 1.8 ml of 10% NaCl in 180ml deionized water was added. Precipitation of solid product took place during the addition. The suspension was stirred for 5 minutes and was allowed to settle for 5 minutes. Complete solid sedimentation was observed. The liquor was decanted and 100 ml methanol was added. The product was suspended in methanol by stirring and the solvent was distilled out under vacuum. The solid residue was dried at 350C under vacuum to a constant weight and ground in mortar "Substance A" . Decanted liquor was evaporated under vacuum to dryness then the solid residue was ground in a mortar "Substance B" ."Substance A": Yield of dry solid - 18.4g, Assay ofGlatiramer by HPLC 23.5% wt, Chemical yield 90%."Substance B": Yield of dry solid - 8.Og, Assay ofGlatiramer by HPLC 5.4% wt.; 1 g Glatiramer acetate was dissolved in 19 ml deionized water. After stirring and complete dissolution, a solution containing 4g tannic acid and 1.8 ml of 10% NaCl in 19 ml deionized water was added over 10 minutes. Precipitation of a solid product took place during the addition. The suspension was stirred for 5 minutes and was allowed to settle for one hour. Complete solid sedimentation was observed, liquor was decanted and 50ml methanol was added. The product was suspended in ethanol , stirred for one hour and the resulting suspension of semi-solid material was filtered. The solid product was dried at 35,°C under vacuum to a constant weight and ground in mortar.Yield of dry solid - 1.2g, Assay of Glatiramer by HPLC 49.3% wt. Chemical yield 70%.; I g Glatiramer acetate was dissolved in 19 ml deionized water. After stirring and complete dissolution, a solution of containing 4 g tannic acid and 1.8 ml of 10% NaCl in 19 ml deionized water was added over 10 minutes. Precipitation of solid product took place during the addition. The suspension was stirred for 5 minutes and was allowed to settle for one hour. Complete solid sedimentation was observed, liquor was decanted and 70 ml ethanol was added. The product was suspended in ethanol by stirring one then the solvent was distilled out under vacuum and stirring. An additional 30 ml of ethanol was introduced and evaporated to dryness under the same conditions. The solid residue was dried at 350C under vacuum to constant weight and ground in mortar. |
In water | 1A A 5% aqueous solution containing 1.9g of glatiramer acetate, with a pH of 5.5, was added to a 10% aqueous solution of tannic acid (USP grade) containing 2.95g of tannic acid, with a pH of 3.2. The solutions were stirred for a few minutes and a suspension with a pH of 4.6 was formed. The suspension was centrifuged at 3220 G for 25 minutes and the colloidal decantate was separated. The solid sediment was washed with deionized water, and centrifuged again at 3220 G for 25 minutes. The clear decantate was discarded and the solid was dried under vacuum (25 mbar) at 40° C and 2.6g of dried solid was formed . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibutyltin dilaurate In dioxolane, 1,3- at 50℃; for 10h; Inert atmosphere; | 11 The synthesis of gallotannic compound MCI09-H03 was performed as follows. In a first reaction flask, a mixture containing 200 grams of 1 ,3-dioxolane and 10.0 grams of 2-chloroethyl isocyanate was added to a solution containing 100 grams of 1 ,3-dioxolane, 17.01 grams of gallotannin and 0.10 grams of dibutyl tin dilaurate under nitrogen atmosphere and constant stirring at 50°C. The reaction was then stirred for 10 hours. A sample was withdrawn from the reaction. The FTIR spectrum was recorded on KBr pellet. The -NCO peak at 2210 cm 1 was not observed on this FTIR spectrum, which indicated that the reaction was complete.[00220] In another reaction flask, 3.00 grams of potassium hydroxide was added into a solution containing 50 grams of ethanol and 11.6 grams of 5,5-dimethylhydantoin. The reaction mixture was stirred at 40°C for 4 hours. It was then cooled to room temperature. Then, the obtained mixture was added to that in the first reaction flask. The mixture was heated at 40°C for 10 hours. The product was precipitated with 2 liters of water, filtered and washed copiously with water. It was air-dried until constant weight, which produced a pale yellow powder. The idealized chemical structure is shown in Figure 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibutyltin dilaurate In dioxolane, 1,3- at 60℃; for 5h; Inert atmosphere; | 12 Gallotannic compound MCI09-M040 was first prepared as an intermediate. This was performed by slowly adding 50 grams of a 1 ,3-dioxolane solution containing 5.25 grams of 2-chloroethyl isocyanate and 0.05 grams of dibutyl tin dilaurate into 350 grams of a 1 ,3-dioxolane solution containing 85.05 grams of gallotannin under nitrogen atmosphere and constant stirring at 60°C The reaction was completed after 5 hours as indicated by the disappearance of the -NCO peak at 2270 cm-1 on the FTIR spectrum. The ideal structure of this compound is shown in Figure 13.[00224] The synthesis of gallotannic dendrimer MCI09-D001 was performed by slowly adding 2.00 grams of sodium hydride (60 % in mineral oil) into a mixture containing 300.0 grams of 1 ,3-dioxolane and 17.0 grams of gallotannin under nitrogen atmosphere and constant stirring at 50°C. When the hydrogen bubbles disappeared, a mixture containing 400 grams of 1 ,3-dioxolane and 90.30 grams of gallotannic compound MCI09-M040 was slowly added into the reaction mixture and stirring continued at 50°C for an additional 10 hours. Then, a mixture containing 100 grams of 1 ,3-dioxolane, 34.7 grams of Ureido-NCO and 0.1 grams of dibutyl tin dilaurate was slowly added into the reaction mixture. Stirring continued at 60°C for 10 hours. The FTIR spectrum of the reaction mixture showed no -NCO group at 2210 cm 1, which indicated that the reaction was complete. The product was precipitated in 5 liters of water an then filtered and washed copiously with water. It was then air- dried until constant weight to produce a pale yellow powder. The idealized chemical structure of gallotannic dendrimer MCI09-D001 is shown in Figure 14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibutyltin dilaurate In dioxolane, 1,3- at 50℃; for 10h; Inert atmosphere; | 6 Gallotannic compound RGT-03 shown in Figure 7 was synthesized by slowly adding 79.0 grams of 4-cyanatobenzyl cyanide (5 equivalents) and 77.5 grams of 2-isocyanatoethyl methacrylate (5 equivalents) in 500 grams anhydrous 1 ,3-dioxolane to a reaction flask containing 800 grams of anhydrous 1 ,3-dioxolane in which were dissolved 170.1 grams of gallotannin (1 equivalent) and 0.5 grams of dibutyl tin dilaurate at 50°C, under oxygen atmosphere with constant stirring. After 10 hours of reaction, a sample of the reaction mixture was withdrawn from the reaction flask and its FTIR spectrum, recorded on KBr pellet, showed no -N=C=0 peak at 2274 cm 1, which indicated that the reaction was completed. The solid content of RGT-03 was adjusted to 20 % by weight using 1 ,3-dioxolane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibutyltin dilaurate In dioxolane, 1,3- at 50℃; Inert atmosphere; | 10 The synthesis of gallotannic compound MCI09-H02 was performed by slowly adding a mixture containing 200 grams of 1 ,3-dioxolane and 10.0 grams of p-toluenesulfonyl isocyanate into a solution containing 100 grams of 1 ,3-dioxolane, 17.01 grams of gallotannin and 0.10 grams of dibutyl tin dilaurate under nitrogen atmosphere and constant stirring at 50°C. The reaction was then stirred for an additional 10 hours. A sample was withdrawn from the reaction. The FTIR spectrum was recorded on KBr pellet. The -NCO peak at 2210 cm 1 was not observed on this FTIR spectrum, which indicated that the reaction was complete. The product solution is ready for use in coating formulation. The idealized chemical structure is shown in Figure 11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibutyltin dilaurate In dioxolane, 1,3- at 50℃; Inert atmosphere; | 8 The synthesis of gallotannic compound MCI09-M090 was performed by slowly adding a mixture containing 200 grams of 1 ,3-dioxolane and 70.0 grams of Ureido-NCO into a solution containing 100 grams of 1 ,3-dioxolane, 17.01 grams of gallotannin and 0.10 grams of dibutyl tin dilaurate under nitrogen atmosphere and constant stirring at 50°C. The reaction was then stirred for an additional 10 hours. A sample was withdrawn from the reaction. The FTIR spectrum was recorded on KBr pellet. The -NCO peak at 2210 cnr1 was not observed on this FTIR spectrum, which indicated that the reaction was complete. The product was precipitated with 2 liters of water, filtered and washed copiously with water. It was air-dried until constant weight, which produced a pale yellow powder. The idealized chemical structure is shown in Figure 9. |
Yield | Reaction Conditions | Operation in experiment |
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With dibutyltin dilaurate In dioxolane, 1,3- at 50℃; for 30h; Inert atmosphere; | 1 Gallotannic compound RGT-01 shown in Figure 2 was synthesized by slowly adding 155 grams of 2-isocyanatoethyl methacrylate (10 equivalents) in 500 grams anhydrous 1 ,3-dioxolane to a reaction flask containing 800 grams of anhydrous 1 ,3-dioxolane, in which were dissolved 170.1 grams of gallotannin (1 equivalent) and 0.5 grams of dibutyl tin dilaurate at 50°C, under oxygen atmosphere with constant stirring. After 30 hours of reaction, a sample of the reaction mixture was withdrawn from the reaction flask and its FTIR spectrum, recorded on KBr pellet, showed no -N=C=0 peak at 2274 cm-1, which indicated that the reaction was completed. The solid content of RGT-01 was adjusted to 20 % by weight using 1 ,3-dioxolane. |
Yield | Reaction Conditions | Operation in experiment |
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Stage #1: tannic acid With sodium hydride In N,N-dimethyl acetamide for 3h; Inert atmosphere; Stage #2: N-methoxymethyl-(1-methyl-2-(2-chloroethyl)amino)-ethylamide In N,N-dimethyl acetamide at 50℃; for 10h; Inert atmosphere; | 2 Gallotannic compound RGT-02 shown in Figure 3 was synthesized by slowly adding 42.0 grams of sodium hydride (10.5 equivalents) to a reaction flask containing 500 grams of anhydrous N,N-dimethylacetamide, in which were dissolved 170.1 grams of gallotannin under nitrogen atmosphere with constant stirring. About three hours later, the release of hydrogen gas by-product ceased and a solution containing 300 grams of Ν,Ν-dimethylacetamide and 209 grams of MMEA (10 equivalents) was slowly added to the reaction mixture. The reaction was stopped after 10 hours at 50°C. The solvent was removed using a rotary evaporator under vacuum until dry. The obtained solid was dissolved in anhydrous 1 ,3-dioxolane to provide a 20 % solid solution. It was then gravity filtered to remove sodium chloride by-product. |
Yield | Reaction Conditions | Operation in experiment |
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General procedure: IIt was prepared based on our preliminary works [18]. This protocol is subjected to three steps as following: Bio-imprinting (modification in aqueous medium): 50 mg TA was added to the tannase solution, which incorporated 16 IU (assayed by rhodanine-spectrophotometric method [19]) tannase with 5 mL 90 mM pH 6.0 citrate buffer as solvent. The uniform enzyme-substrate mixture was maintained without agitation for 5 min at ambient temperature. The enzyme-substrate mixture was defined as a TA-pH treated tannase (TPt). (The lyophilized powder of TPt is considered as bio-imprinted tannase.) Cryogenic protection (prior to lyophilization) and immobilization: 12.5 muL 200 mM magnesium ion solution, 0.625 mL 1M mannose, 0.15 mL 10 mM Triton-X-100, and 0.5 g celite were decanted to TPt, in turn, and then the mixture was agitated for 5 min. Lyophilization: The modified enzyme mixture was frozen at -20 C overnight, followed by lyophilization using a freeze dryer (VirTis, SP Scientific USA). The lyophilized powders (i.e., IIt) were stored at 4 C until use. As for different requirements, the protocol was modified based on the above steps. 2.3. Transesterification synthesis of propyl gallate. An aliquot of IIt (containing 50 mg TA) was added into approximate 10 mL reaction medium, which is composed of 1 mL n-propanol, 9 mL hexane, and 0.1 mL distilled water. The reaction was performed at 40 C and 200 rpm for 24 h. Conversion rate (CR) in the transesterification reaction refers to the mole percent of TA completely transformed to PG (C0 - Ct) relative to the total dose of TA (a fixed concentration, C0) before the equilibrium of reaction (in a fixed time, t). The reaction rate can be calculated as the following: nu = (C0 - Ct)/t = (C0 - Ct)C0/tC0 = (CR × C0)/t. If k is defined as C0/t, v = kCR, where v is the reaction rate of transesterification catalyzed by tannase, which, in general, denotes the transesterification-catalyzing capability of the enzyme. C0 and Ct are the initial concentration of TA and the residual concentration of TA in a fixed time, t, respectively. In view of C0 and t being constants, v is proportional to CR. Therefore, CR can be used to estimate the catalytic activity of the enzyme. The activation factor (AF) refers to the CR of the modified tannase divided by one of the corresponding control, which intuitively denotes the effect of treatment on the catalytic activity of the enzyme. The control was prepared according to the different requirements. All experiments were performed in duplicate unless stated otherwise. 2.4. Assay of propyl gallate. Samples were assayed by HPLC (Waters 600, Waters, USA) with a Waters 996 photodiode array detector (PDAD) as well as a Phenomenex C18 column (250 × 4.60 mm, 4 mum). The mobile phase was composed of 50 mL of methanol, 50 mL of pure water, and 10 muL of acetic acid. The operating temperature was maintained at 35 C. 20 muL of sample were injected and were detected at 274 nm with PG (HPLC grade) as the control at a flow rate of 1 mL/min. | ||
With immobilized tannase; In hexane; water; at 40℃; for 24h; | The immobilized tannase and 50 mg tannic acid were added into a 25 mL flask with approximate 20 mL reactive mixture com-posed of 2 mL n-propanol, 18 mL bulky medium (i.e., n-propanol,isopropanol, n-hexane, cyclohexane, benzene, and ethylbenzene),and 100 L distilled water. The reaction was carried out at 40C and200 rpm for 24 h. The content of product, propyl gallate (PG), wasdetermined by HPLC (Shimazduo LC-20A, Shimazduo, JPN) to esti-mate the catalytic performance of tannase. All experiments wereperformed in duplicates. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With recombinant Tan410 In aq. phosphate buffer at 35℃; for 0.75h; Enzymatic reaction; | ||
With ammonium nitrate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; magnesium sulfate In water at 35℃; for 39h; Microbiological reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With toluene-4-sulfonic acid In toluene at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
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1.8 g | With sodium hydroxide at 85 - 90℃; for 1h; Sonication; | 5 Example 5 Taking 13g turn jambolans tannin, adding 0.5mol/L sodium hydroxide solution of 390 ml, in 85-90 °C lower, ultrasonic power 500w, ultrasonic reaction time 60 min. The reaction liquid by adding dilute hydrochloric acid under stirring, until the pH value of the reaction liquid 5, filtering, the filter cake after the water washing, ellagic acid to obtain brown crude product, crude product purity is 69.6%. Crude product with embodiment 2 process is refined drying to obtain strawcoloured ellagic acid product 1.8g, content is 98.4%.; The ellagic acid is added to sodium hydroxide dilute solution of the crude product, by adding activated carbon, in the 50 °C reaction under the temperature 1 hour, filtering the reaction liquid, and for washing the filter cake, combined filtrate and wash liquid; adding dilute hydrochloric acid to pH of the solution is adjusted to pH value of 4, filtering, the filter cake is water-washing, and drying to obtain strawcoloured ellagic acid product 0.6g, content is 98.1%. |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20 - 25℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
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86.35% | In water at 60℃; for 5h; | 1.1; 2.1; 3.1; 4.1; 5.1 (1) Weigh tannic acid and histidine with a molar ratio of 1:1 and dissolve them in 50 ml of distilled water, add the histidine solution dropwise to the tannic acid solution and stir well, adjust the pH to 6, and react at 60°C for 5 h. The pH was adjusted to 9 and precipitation occurred, washed three times with twice distilled water, filtered, and dried to obtain a pale yellow solid tannic acid-histidine salt with a yield of 86.35%. |
Yield | Reaction Conditions | Operation in experiment |
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In water at 90℃; | 9.A Example 9; Experiment “A&rdquo Experiment “A” [00036] 14 g of dextromethorphan HBr was mixed with 12 g of water and 34 g of tannic acid. The reaction mixture was heated to 90° C. and stirred for several minutes. After cooling to room temperature, a portion of the product was dried at 50+/-5° C. under 29.5 inches vacuum for 4 hours. One gram of the dried product was added to 110 g of methylene chloride and the mixture was stirred for 20 minutes at room temperature. The resultant mixture was filtered and the precipitate was dried. The precipitate (about 30 g) had a decomposition point of about 210° C. Such decomposition point compares quite closely to the reference decomposition point of 210-215° C. for pure tannic acid, which indicated that the tannic acid had not reacted with the dextromethorphan HBr. [00037] The filtrate was evaporated to dryness and the resultant solid (about 12 g) was then dried. The dried solid had a melting point of about 121° C. which compared quite closely to the melting point of 123° C. for pure dextromethorphan-HBr which indicated that the tannic acid had not reacted with the dextromethorphan-HBr. A sample of the dried solid was then subject to FTIR analysis and the spectrum which was obtained was then compared to the FTIR spectrum of pure dextromethorphan HBR. The two spectra were nearly identical. Therefore, it is clear that the dextromethorphan-HBr did not react with the tannic acid to form dextromethorphan tannate and that the dextromethorphan-HBr was present as a mixture with the tannic acid. | |
With Na casein; potato strach; lactose In water at 90℃; | 9.B Example 9; Experiment “B&rdquo Experiment “B” [00038] Experiment “A” was repeated using additional amounts of lactose, potato starch and Na casein as described by Sawai et al. One gram of the reaction product was mixed with 110 g methylene chloride and then filtered. The solid obtained by evaporating the methylene chloride filtrate to dryness was again found by melting point and FTIR analysis to be substantially all unreacted dextromethorphan-HBr, while the precipitate which did not dissolve in the methylene chloride was found to be a mixture of tannic acid, lactose, potato starch and Na casein. Therefore, it is clear that despite the presence of lactose, potato starch and casein, the dextromethorphan-HBR did not react with the tannic acid and that the reaction product consisted of a mixture of dextromethorphan-HBr, tannic acid, lactose, potato starch and Na casein. |
Yield | Reaction Conditions | Operation in experiment |
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95.6% | Stage #1: tannic acid In water at 85 - 100℃; for 0.166667h; Stage #2: levomethorphan In water at 85 - 100℃; for 1.25h; | 1 EXAMPLE 1 EXAMPLE 1 [00025] A 500 ml flask was equipped with a stirrer, thermometer, nitrogen blanket and a hot water bath. The hot water bath was heated to, and maintained at, a temperature of 85 to 100° C. Water in the amount of 25 g was placed in the flask and thereafter 88.8 g(0.052 m) of tannic acid were added to the heated water over a period of about 5 minutes. Stirring was continued for an additional 10 minutes, while maintaining a temperature of 85-100° C. to thereby obtain a smooth slurry of the tannic acid. Thereafter, 71.2 g (0.262 m) of dextromethorphan were added to the heated slurry, with stirring, over a period of about 15 minutes, while maintaining a temperature of 85-100° C. String was continued for a period of about 1 hour, while maintaining the same temperature and the reaction mixture was then allowed to cool to room temperature. The product became very hard after about 2 hours at room temperature. The yield of the product obtained was 148.8 g (95.6% of theory). Karl Fischer analysis indicated that the product contained 11.1% water. The product was milled to a fine powder and thereafter dried to a moisture content of 3.6% (K.F.) at a temperature of about 40-45° C. while sparging with nitrogen over a 24 hour period. The dried product had a softening point of about 108-115° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 90℃; | 9.C Example 9; Experiment “C&rdquo Experiment “C” [00039] 14 g of dextromethorphan free base was mixed with 12 g of water and 36 g of tannate acid. The mixture was heated with stirring, to 90° C. and maintained at such temperature for several minutes. After cooling to room temperature, the reaction product was dried and powdered. A sample of the powdered product was mixed with methylene chloride, but no dissolution occurred, indicating that the reaction product did not consist of dextromethorphan free base. A sample of the reaction product was dried to a moisture (K.F.) level of about 4% and it was determined that such material had a softening point of about 100° C. (in comparison to the sharp melting point of 123° C. for dextromethorphan-HBr, the melting point of 109.5-112.5° C. for dextromethorphan free base and the decomposition point of 210-215° C. for tannic acid). The reaction product was also subjected to FTIR analysis and the spectrum obtained thereby was quite different from that of either dextromethorphan free base or tannic acid (or dextromethorphan-HBr). Therefore, it is clear that when dextromethorphan free base is reacted with tannic acid in accordance with the process of the invention, a unique type of dextromethorphan tannate product is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 140 - 150℃; for 2h; Neat (no solvent); | 2 EXAMPLE 2 EXAMPLE 2 [00026] A 500 cc resin flask was fitted with a stirrer, thermometer, nitrogen blanket and a hot oil bath. Dextromethorphan in the amount of 71.2 g (0.262 m) was placed in the flask and the temperature of the oil bath was gradually raised to 140-150° C. At this point, the dextromethorphan (which melts at about 110° C.) was fully molten. Tannic acid (neat) in the amount of 89 g (0.052 m) was added over a period of several minutes to the molten dextromethorphan, while stirring was continued and the oil bath temperature was maintained at 140-150° C. Thereafter, stirring was continued for about 2 hours, while maintaining the temperature of the oil bath at about 140-150° C. The reaction mixture was then cooled to room temperature and the tan-colored product was milled to a fine powder, which was then dried under 29 inches of vacuum at 50-55° C. for 24 hours. The yield of the product was 151 g (97% of theory). The softening point of the product which had a moisture content of 2.8% (K.F.) was 138-143° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.6% | Stage #1: tannic acid In isopropyl alcohol at 40 - 45℃; for 1h; Stage #2: levomethorphan In isopropyl alcohol at 45 - 50℃; for 1h; | 5 EXAMPLE 5 EXAMPLE 5 [00029] Example 1 was repeated using the following materials: 34.02 g of tannic acid and 340 g of isopropyl alcohol were placed in the reaction vessel and stirred while maintaining a temperature of about 40-45° C. Thereafter, a clear solution of 27.1 g of dextromethorphan free base in 270 g of isopropyl alcohol was added, over a period of one hour, while stirring, to the reaction vessel while the temperature of the reaction mixture was raised to, and maintained at, 45-50° for an additional hour. The resultant cream-colored solid was filtered off and washed with 25 g of isopropyl alcohol. The reaction product was then dried under vacuum at a temperature of 55-65° C. The yield of the product was 51.1 g (83.6% of theory). The dried product had a moisture content of 4.95% had a softening point of 172-177° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. phosphate buffer |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. phosphate buffer |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
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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