1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside
Sucralose
CAS: 56038-13-2
Molecular Formula: C12H19Cl3O8
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Names and Identifiers
| Name | Sucralose |
| Synonyms | Sucralose ctopyranoside loro-4-deoxy- 1,6-dichloro-1 4,1',6'-trichlorogalactosucrose Sucralose in stock GMP Factory 4,1',6'-trichloro-4,1',6'-trideoxy-galacto-sucrose 4,1',6',-trichloro-4,1',6'trideoxy-Pentagalactosucrose 1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl4-chloro-4-deoxy-alpha-d-gala alpha-d-galactopyranoside,1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl4-ch 1,6-Dichloro-1,6-dideoxy-beta-D-fructofuranosyl-4-chloro-4-deoxy-alpha-D-galactopyranoside |
| CAS | 56038-13-2 |
| EINECS | 259-952-2 |
| InChI | InChI=1/C12H19Cl3O8/c13-1-4-7(17)10(20)12(3-14,22-4)23-11-9(19)8(18)6(15)5(2-16)21-11/h4-11,16-20H,1-3H2 |
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Physico-chemical Properties
| Molecular Formula | C12H19Cl3O8 |
| Molar Mass | 397.63 |
| Density | 1.375 g/cm |
| Melting Point | 115-1018°C |
| Boling Point | 104-107 C |
| Specific Rotation(α) | D +68.2° (c = 1.1 in ethanol) |
| Flash Point | 358.7°C |
| Water Solubility | Soluble in Water. |
| Solubility | Soluble in water, ethanol, methanol. |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | White or nearly white crystalline powder |
| Color | White |
| Merck | 14,8880 |
| BRN | 3654410 |
| pKa | 12.52±0.70(Predicted) |
| PH | 6-8 (100g/l, H2O, 20°C) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.604 |
| MDL | MFCD03648615 |
| Physical and Chemical Properties | white or nearly white crystalline powder; Odorless, sweet. Light, Heat, acid are stable, soluble in water, ethanol, methanol.
|
| Use | Used as a food sweetener |
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LW5440140 |
| HS Code | 2932 14 00 |
| Toxicity | LD50 orally in Rabbit: > 10000 mg/kg |
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Upstream Downstream Industry
| Raw Materials | D(+)-Sucrose |
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Reference
| Reference Show more | 1. Huang Zhuoquan Liu huanmai Runqiu, etc. Exposure risk assessment of four kinds of food additives in bergamot fruit [J]. Journal of Food Safety and quality testing, 2020 011(008):2645-2649. 2. Li Xiaolan, Huang Cheng'an, Pan pick-up, Wu Siyan, Zheng guili. Evaluation of uncertainty in determination of sucralose in probiotic powder by high performance liquid chromatography [J]. Journal of Food Safety and quality testing, 2020,11(23):8730-8735. 3. Ren, Jing-Nan, et al. "Effect of short-term take of four sweeteners on feed take, solution consumption and neurotransmitters release on mice." Journal of Food Science and Technology 58.6 (2021): 2227-2236.https:// doi.org/10.1007/s13197-020-04733-7 4. Wang, Lifeng, et al. "Chlorine-doped graphene quantum dots with enhanced anti-and pro-oxidant properties." ACS applied materials & interfaces 11.24 (2019): 21822-21829. 5. Yin, Kai‐Jing, et al. "Effect and mechanism of high‐fat diet on the preference for sweeteners on mice." Journal of the Science of Food and Agriculture 101.5 (2021): 1844-1853.https://doi.org/10.1002/jsfa.10798 6. Yin, Kai-Jing et al. "Effects of different sweeteners on behavior and neurotransmitters release in mice." Journal of food science and technology 57.1 (2020): 113-121.https://doi.org/10.1007/s13197-019-04036-6 7. [IF=3.638] Kai-Jing Yin et al."Effect and mechanism of high-fat diet on the preference for sweeteners on mice."J Sci Food Agr. 2021 Mar;101(5):1844-1853 |
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Nature
Open Data Verified Data
White Crystal or crystalline powder, odorless, sweet. Soluble in water (20 ℃, 28.2g/lOOmL), ethanol, insoluble in corn oil. The pH value of 10% aqueous solution is 5~8. No heat, no dental caries, good stability, especially in aqueous solution is very stable.
Last Update：2024-01-02 23:10:35
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Preparation Method
Open Data Verified Data
with sucrose as raw material, by triphenylmethylation (shielding three primary hydroxyl groups), acetylation (shielding five secondary hydroxyl groups), detriphenylmethyl, acetyl migration, chlorination, deacetylated groups were obtained from sucralose.
Last Update：2022-01-01 10:10:21
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Standard
Authoritative Data Verified Data
This product is 1,6-two gas -1,6-dideoxy-Lu -1> fructose -4-gas -4-deoxy-«-D-galactoside. Calculated as the dried product, the content of C12 H19C13 0 8 should be 98. 0% ~ 102.
Last Update：2024-01-02 23:10:35
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder. Color tends to darken when exposed to light and heat.
- This product is soluble in water, soluble in anhydrous ethanol, slightly soluble in ethyl acetate.
specific rotation
take this product l .O g, precision weighing, put in a measuring flask, add water to dissolve and dilute to the scale, shake well, and determine according to law (General rule 0621), the specific rotation is 84. 0 ° to 87 °. 5 degrees.
Last Update：2022-01-01 11:20:15
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Use
Open Data Verified Data
sucralose is a sweetener approved in China. Its sweetness is about 600 times that of sucrose, the sweet taste is pure, and the sweet characteristics are very similar to the sweet quality and sucrose. In general food processing and storage processes are very stable, water-soluble, suitable for a variety of food processing. China's provisions can be used in beverages, pickles, compound seasoning, wine, ice cream, cakes, biscuits, bread and many other fields.
Last Update：2022-01-01 10:10:22
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Differential diagnosis
Authoritative Data Verified Data
- O .lg of the product was taken, dissolved in methanol and diluted to prepare a solution containing 10 M g per lm l as a test solution. An appropriate amount of the three-gas sucrose control was taken, dissolved and diluted with methanol to prepare a solution containing 10 mg per 1 ml as a control solution. The position and color of the main spot of the test solution shall be the same as that of the main spot of the reference solution according to the chromatographic conditions under the relevant substance inspection item.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the three-gas sucrose reference substance (General rule 0402).
The above 1, 2 two items can be done one.
Last Update：2022-01-01 11:20:16
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Exam
Authoritative Data Verified Data
hydrolysate
Take 2. 5 g of this product, put it in a 10ml measuring flask, dissolve it in methanol and dilute it to the scale, shake it well, and use it as a test solution. Take an appropriate amount of mannitol control, dissolve and quantitatively dilute with water to make a solution containing 0. l g of solution, as a control solution (1 ) ; In addition, mannitol and fructose were dissolved in an appropriate amount of the reference substance, and diluted quantitatively with water to prepare a solution containing 0. l g and 0. 4M g mixed solution, as a control solution (2). Take each 5fxl of the control solution (1), (2) and the test solution respectively, and put them on the same silica gel G thin layer plate, and continue to put them after each sample is dried, the area of each point should be basically the same, and the color developing agent (take p-Anisidine 1 .2 3 g and phthalic acid 1.66g, dissolve with methanol 100ml, store the solution in the dark and refrigerated, if the solution fades, it will be ineffective) after spraying, heat in the oven for 15 minutes, immediately after heating, the thin layer plate was observed in a dark background, and the spot of the test solution should not be deeper than the spot of the control solution (2). The control solution (1) should show white spots. If the spots turn black, that is, the thin layer plate is heated for too long, it is necessary to try again.
Related substances
take an appropriate amount of this product, precisely weigh it, dissolve and quantitatively dilute it with fermentation broth to prepare a solution containing O . lg per lm l as a test solution. The sample solution lm l was accurately measured, placed in a 200ml measuring flask, and diluted to the scale with methyl alcohol to serve as a control solution. According to the thin layer chromatography (General 0502) test, Draw 5m for the test solution and 5m for the control solution, point on the same eighteen alkyl silane bonded silica gel thin layer plate (Whatman partial SIL lkc18 F plate or equivalent thin layer plate), with 5% gasification sodium solution-acetonitrile (70 > 30) as the developing agent, at a distance of 1 5 cm, it was taken out to dry, sprayed with 15% sulfuric acid methanol solution, and heated at 125t for 10 minutes. The impurity spots in the test solution shall not be deeper than the main spots in the control solution.
methanol
take about 0.4g of this product, precision weighing, set in the top empty bottle, Precision Add 2M l of water to dissolve, Precision Add internal standard solution (take the right amount of isopropyl alcohol, precision weighing, diluted with water to produce O per lm l. lm g solution) 2ml, sealed, shake, as a test solution; Take the appropriate amount of methanol, precision weighing, diluted with water to make a solution containing 0.2mg per lm l, take 2ml of precision, set in the top empty bottle, Precision Plus 2ml of internal standard solution, Seal, shake, as a control solution. Measured by gas chromatography (General 0521). With 6% cyanophenylpropyl-94% methyl polysiloxane as stationary phase, I injection port temperature 2 20 C; Detector temperature 250C; Initial temperature 3 5 1, for 5 minutes, the temperature was raised to 20 0 C at 50C per minute for 5 minutes. The equilibrium temperature of the headspace bottle is 80C, and the equilibrium time is 30 minutes. The reference solution and the test solution are respectively injected into the headspace * record the chromatogram, and the peak area is calculated according to the internal standard method, containing methanol should not be over 0 .1%.
moisture
take 0.5g of this product, according to the determination method of moisture (General rule 0832 first method), the water content shall not exceed.
ignition residue
The l.O g of this product shall be taken for inspection according to law (General rule 0841), and the remaining residue shall not exceed 0 .7%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 11:20:17
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
The mobile phase was water-acetonitrile (85 : 15) using a Eighteen alkyl silane-bonded silica gel as a filler and a refractive index detector at a flow rate of 1.0ml per minute. The number of theoretical plates shall not be less than 2000 based on the calculation of the three-gas sucrose peak.
assay
take an appropriate amount of this product, dissolve and dilute it with mobile phase to make a solution containing 10 mg per lm l, Take 2(^ 1, inject human liquid chromatograph, record the chromatogram. Another three gas sucrose reference substance was determined by the same method, and the peak area was calculated by the external standard method.
Last Update：2022-01-01 11:20:18
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Category
Authoritative Data Verified Data
pharmaceutical excipients, flavors and sweeteners.
Last Update：2022-01-01 11:20:18
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Storage
Authoritative Data Verified Data
light shielding, sealed storage, temperature does not exceed 25C.
Last Update：2022-01-01 11:20:18
1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside - Reference Information
| LogP | -0.51 at 20℃ |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | sucralose is a white powder product that is highly soluble in water, ethanol, and methanol, is the only sucrose as raw material production of functional sweeteners, its sweetness is 600 times sucrose, and sweet pure, sweet characteristics are very similar to sucrose, without any bitter taste; No heat, no caries, good stability, especially in aqueous solution is particularly stable. After a long period of toxicological tests, it is proved to be the most excellent functional sweetener with high safety. It has been approved by more than 30 countries such as the United States, Canada, Australia, Russia and China. At present, sucralose has been widely used in beverages. |
| properties | sucralose is currently the highest level of development and research of high intensity sweeteners in the world, with excellent performance. sucralose is a white powder product, very soluble in water (solubility 28.2g,20 ℃), 600 times the sweetness of sucrose, and sweet pure, the sweet taste characteristic curve almost overlapped with sucrose. Sucralose is a non-nutritive high-intensity sweetener that is hardly absorbed in the human body and has a zero caloric value. Sucralose is stable in nature and its crystalline product is also stable for 4 years of storage at 20 °c under dry conditions. In aqueous solution, sucralose is the most stable of all high-intensity sweeteners in the pH range of soft drinks (pH3-5) and at normal temperatures, can be stored for more than one year without any change. |
| Use | Non-nutritive sweetener, widely used in beverage, food, medicine, cosmetics and other industries, as sucralose is a new non-nutritive sweetener, which is an ideal food additive for patients with obesity, cardiovascular disease and diabetes, its application in health food and medicine is expanding. In recent years, medical research has used it as a tracer molecule for the determination of colon permeability, and the method is mostly used in the analysis of gas chromatography. The sensitivity and specificity need to be further studied. The product is today's most ideal high-intensity sweeteners for children, adolescents, young, middle-aged, elderly and a variety of diseases, without any nutritional doubt. used as food sweetener, nutritional supplement, one of essential amino acids Non-nutritive sweetener. Non-nutritive sweetener. sucralose is widely used in processed foods such as beverages, chewing gum, dairy products, preserved fruits, jelly pudding, bread, cakes, biscuits, ice cream and jam used as an upstream raw material of food sweeteners: sucrose A synthetic sweetener that activates the T1R2/T1R3 sweet taste receptors on enteroendocrine cells and induces glucagon-like peptide 1(glucagons-like peptide-1,GLP-1) and glucose-dependent secretion of the insulinotropic peptide (peptide). sucralose is a new sweetener approved in China. China's provisions can be used for pickles, compound seasoning, wine, beverages, ice cream, popsicles, cakes, canned fruit, biscuits and bread, the maximum use of 2.5g/kg; In candied fruit, modified chewing gum in the maximum use of 1.5g/kg; Can also be used as table sweeteners, the maximum amount of 0.05g/pack, tablets. |
| food sweetener | sucralose, also known as sucralose, is a strong food sweetener, trade name spluda, referred to as TGS. Sucralose is the fifth generation artificial sweetener after saccharin, sodium cyclamate, aspartame and acesulfame-K. It is the only sweetener with sucrose as raw material so far, it is approved by the state for use in food and beverage additives. Sucralose is the most perfect and competitive artificial sweetener. It has high sweetness, good flavor, non-nutritive, long storage period, low calorific value and high safety. Sucralose from sucrose 4-,1 '-and 6'-hydroxy group is chlorine, by the University of London, UK Professor Leslie Hough and Tate & Lyle co-developed in 1976, it was introduced into the market in 1988. Sucralose is a non-caloric high-power sweetener substance made of sucrose, white powder, odorless, non-hygroscopic and other characteristics, high thermal stability, easily soluble in water, soluble in ethanol and methanol and other organic solvents. Its solubility is 28.2g at 28 °c. The stability is high in the light environment, thermal environment and pH value. |
| Application | sucralose has been widely used in beverages, table sweeteners, ice cream, baked goods, chewing gum, coffee, dairy products, sweet snacks, fruit juice, gelatin food, pudding, sweet sauce, syrup, soy sauce, medicine, cosmetics and other industries. The United States, Canada and other countries have replaced sucrose and other sweeteners in a variety of foods. Sucralose does not damage teeth, does not cause disease as sucrose, fructose and maltose, and is not as sweet as other nutritive sweeteners. Sucralose is available for people with obesity, cardiovascular disease and diabetes. |
| range of use | FAO and FAO/WHO committee on food additives World Health Organization (WHO) its daily allowance is set at 0-15mg/kg body weight. |
| assay | high pressure liquid chromatography was used. The mobile phase consisted of 150ml of acetonitrile in 850ml of water, filtered and degassed. The standard solution is 100mg(We) of a reference standard sample of chlorinated sucrose produced by Tate & Lyle, UK. The volume of the reference standard is set to 100ml with the mobile phase solution, and the amount of the reference standard is recorded as Ws. The mobile phase pressure was 101.325kPa, and the flow rate was 1.5/min. The absorbance at 190nm was detected with an ultraviolet detector. The injection amount of the sample and the standard sample is 20 μl, and the retention time of sucralose is about 9min. Finally, the peak area (Ac) of the sample and the peak area (As) of the standard sample are calculated, the purity% rate of the sample is calculated according to the following formula: purity (%) = Ac × Ws/As × We × 100 Finally, the water content and methanol content in the quality index are determined according to the measurement results of water content and methanol content, percent purity without methanol groups. |
| toxicity | ADI 0-15mg/kg(FAO/WHO,2001). |
| usage limit | GB 2760-1997(g/kg): Table sweetener, 0.05g/pack, tablet; juice-based beverages, pickles, complex flavorings, wine, ice creams, ice cream, popsicles, cakes, biscuits, bread, unsweetened sweet canned fruits, beverages, 0.25; Modified chewing gum, preserved fruit, 1.5. The United States in 4.1, approved for baked goods and pre-mix, beverages and their bases, chewing gum, coffee, tea, imitation dairy products and other 15 types of food. GB 2760-2002(g/kg): solid beverage, fruit and vegetable juice concentrate, salad dressing, 1.25; Mustard dressing, 0.4; Breakfast cereal, sweet milk powder, 1.0; Candy, 1.5; Flavored or fruit yogurt 0.3; fermented wine 0.65; Jam 0.45; Fruit filling 0.25; Heat processed fruit or dehydrated fruit 0.15. |
| production method | The synthetic route of sucralose can be divided into three categories: monoester method, chemical-enzymatic and group migration methods. Chemical-enzymatic 6-SITE group protection method was developed by the company Tate-Lyle. Glucose -6-acetic acid was first produced by fermentation of glucose at 30 ° C. With the highest concentration of glucose -6-acetic acid up to 15g/L, the yield can reach 85% of the theoretical yield. Then the glucose -6-acetic acid was purified by the method of methanol extraction and silica gel column chromatography, and the purification yield was 80% ~ 85%. Under the action of β-fructosyltransferase produced by Bacillus subtilis, glucose -6-acetic acid reacts with sucrose to produce sucrose -6-acetic acid, the concentration of sucrose -6-acetic acid can reach 120g/L, and the yield of this step is 58%. The purity of sucrose -6-acetic acid was 70% by chromatography. The reaction of sucrose -6-acetic acid with a Vilsmeier reagent made from phosphorus pentachloride and DMF results in 4,1 ',6',-trichloro-4, 1 ',6'-trideoxy-sucrose pentaacetic acid, the yield for this step was 39%. Sucralose was obtained by removing the acetic acid group from sucralose pentaacetic acid, and the yield of deacetic acid was 90%. The fermentation Cost of glucose -6-acetic acid is high, and the purification of sucrose -6-acetic acid is difficult, and the total yield is about 20%. The synthetic route is as follows: the method of synthesizing raffinose is also developed by the company Tate-Lyle. Raffinose in plants such as sugar beet and cotton seed, there is no large supply of goods, can be synthesized by the saturated solution of galactose and sucrose at 30 ℃, under the action of shovel galactosidase, the product concentration can reach 7.5g/L. Raffinose is chlorinated with thionyl chloride in the presence of triphenylphosphorus to produce 4,1 ',6',6 '-tetrachloro-4, 1',6 ', 6 ''-tetradeoxygalactose raffinose heptanoacetic acid. 4,1 ',6',6 '-tetrachloro-4, 1',6 ',6'-tetradeoxygalactose raffinose (TCR) was obtained after deacetic acid of the latter, the yield of TCR was 32.6%. Under the reaction of TCR at 30 ℃ and α-galactosidase for 24h, sucralose was produced with the yield of 80% ~ 90%. The total yield was 26%-29%. Monoester method this method was proposed in 1982 by K S of Khan R A and Muyti. According to the reaction principle of alkyd esterification, a certain hydroxyl group in the sucrose molecule is shielded, and the monoester content is as high as possible by controlling the conditions. Then the product is obtained by separation, chlorination, deesterification and purification. This method is difficult to control the position and degree of esterification, and the yield is only 5% ~ 7%. Base called migration method with sucrose as raw material, by three benzene methylation (shielding three primary hydroxyl groups), acetylation (shielding five secondary hydroxyl groups), detriphenylmethyl, acetyl migration, chlorination, deacetylation and other steps give sucralose. Triphenylmethylation and acetylation 50g of sucrose and 60g of N-methylmorpholine were dissolved in 100ml of dimethylformamide at 50 °c. After half an hour, a total of 141.8G of triphenylmethyl chloride (purity 97%) was added in three portions, and heating was continued for 3.5h. An additional 42.7g of sodium bicarbonate was added and the temperature was maintained at 50 °c for 1H. The solution was dried in vacuo, then dissolved in 115 of acetic anhydride, 15.6g of potassium acetate were added, heated to °c and held for 3 hours. After cooling, 124.6 ml of ethanol was added to obtain 183.2G of crystalline material, containing 68.6% G of 6,1,6 '-trioxy-trityl-pentaacetyl sucrose (Tris PA), with a yield. Detriphenylmethyl 200g of Tris PA was dissolved in 1.7 of toluene and cooled to 0 ° C., hydrogen chloride gas g, and a precipitate was formed after 4.5h. It was purified in nitrogen for 1H to remove residual hydrogen chloride gas, filtered and washed with 65ml of toluene to form a granule, which was redissolved in 120ml of 1% triethylamine toluene solution, the mixture was again filtered, washed with 65ml of toluene and dried to give 81g of 2,3,3 ',4,4'-pentaoxy-acetyl sucrose (4-PAS) in 80% yield. Acetyl migration 50g of 4-pas was dissolved in 100ml of water, heated to 60 °c, filtered while hot, and cooled to room temperature. 2.5 of pyridine was added and stirred at room temperature for 1 h. The solution was acidified with 2.5ml of concentrated hydrochloric acid and extracted with dichloromethane (2 x 125ml). The extract was concentrated to 50ml, and heptane (3 × 50ml) was added and stirred to precipitate crystals. After 20min filtration, the crystals were rinsed with 30ml of heptane and dried under vacuum for 16h to give 34g of 2,3,3 ',4', 6-penta-acetylsucrose (6-pas), the yield was 58%. Chlorination 50g of 6-PAS and 50.3g of triphenylphosphine oxide (TPPO) were stirred in 150mL of toluene solution to make slurry, and 32.8mL of thionyl chloride was added at room temperature, the solution was refluxed for 2.5h and then cooled to 40 °c. Then add 200ml of water to further cool to 0 ℃, stir the mixture vigorously for 1H, filter, rinse with 75ml of toluene: water (1:2) to obtain crude 4,1 ',6'-trichloro-4, 1 ',6'-trideoxy-acetyl-galacto-sucrose (TOSPA). It was dissolved in 75% ml of hot methanol, stirred at 20 °c for 1H, recrystallized and filtered again to obtain 40g of pure TOSPA, with a yield. Deacetylation 50g of TOSPA and 1.5g of sodium methoxide were dissolved in of methanol and stirred for h under vacuum. After addition of Amberlite IRC50(H +) resin, the solution was neutralized by stirring again, filtered, and the filtrate was decolorized with 2g of activated carbon and 2g of Celite and concentrated. 92% of ethyl acetate was added and sucralose was crystallized out. After washing and drying, the product weighed 26g and the purity was. The basic reaction is shown in figure 02346-1, which consists of sucrose selectively replacing three hydroxyl groups on sucrose with chlorine. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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Raw Materials for 1,6-dichloro-1,6-dideoxyhex-2-ulofuranosyl 4-chloro-4-deoxyhexopyranoside