56038-13-2

Basic information

• Product Name: Sucralose
• Synonyms: 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl4-chloro-4-deoxy-alpha-d-gala;4,1’,6’-trichloro-4,1’,6’-trideoxy-galacto-sucrose;alpha-d-galactopyranoside,1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl4-ch;ctopyranoside;loro-4-deoxy-;1,6-DICHLORO-1,6-DIDEOXY-BETA-D-FRUCTOFURANOSYL-4-CHLORO-4-DEOXY-ALPHA-D-GALACOTOPYRANOSIDE;1,6-Dichloro-1,6-dideoxy-beta-D-fructofuranosyl 4-chloro-4-deoxy-alpha-D-galactose;SUCRALOSE
• CAS NO: 56038-13-2
• Molecular Formula: C₁₂H₁₉Cl₃O₈
• Molecular Weight: 397.63
• EINECS: 259-952-2
• Product Categories: Miscellaneous Biochemicals;pharmacetical;Oligosaccharide Compounds;Nutritional Supplements;Sweeteners;Oligosaccharides;Ring Systems;Food & Flavor Additives;Food Ingredients;HISTOSTAT;Food addive,sweeteners;Food additives
• Mol File: 56038-13-2.mol

Chemical Properties

• Melting Point: 115-1018°C
• Boiling Point: 104-107 C
• Flash Point: 358.7 °C
• Appearance: White/Powder
• Density: 1.375 g/cm
• Vapor Pressure: 8.79E-21mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Do you have solubility information on this product that you woul
• PKA: 12.52±0.70(Predicted)
• Water Solubility: Soluble in Water.
• Stability: Hygroscopic
• Merck: 14,8880
• BRN: 3654410
• CAS DataBase Reference: Sucralose(CAS DataBase Reference)
• NIST Chemistry Reference: Sucralose(56038-13-2)
• EPA Substance Registry System: Sucralose(56038-13-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• RTECS: LW5440140
• Hazardous Substances Data: 56038-13-2(Hazardous Substances Data)

Usage

Chemical Properties

Sucralose is a white to off-white colored, free-flowing, crystalline powder.

History

Sucralose, 1,6-dichloro-1,6-dideoxy-β-D-fructofuranosyl- 4-chloro-4-deoxy-α-D-galactopyranoside, is a trichloro-galactosucrose sweetener developed by the British sugar company Tate & Lyle during the 1970s (U.S. Pat. 4,343,934 (Aug. 10, 1982), M. R. Jenner and D. Waite (to Talres Development), (U.S. Pat. 4,362,869 (Dec. 7, 1982), M. R. Jenner and co-workers (to Talres Development), and (U.S. Pat. 4,435,440 (Mar. 6, 1984), L. Hough, S. P. Phadnis, and R. A. Khan (to Tate & Lyle). It was licensed to McNeil-PPC, Inc., a Johnson & Johnson subsidiary, in the United States until a new agreement took place in February, 2004. McNeil Nutritionals retained ownership of SPLENDA Brand and the right for its worldwide retail and food service business. Tate & Lyle became the sole manufacturer of SPLENDA Brand sucralose and owned the right for its worldwide ingredient sales.

Uses

Different sources of media describe the Uses of 56038-13-2 differently. You can refer to the following data:
1. A low-calorie artificial sweetener
2. High intensity sweetener manufactured by replacing three hydroxyl groups on the sucrose molecule with three chlorine atoms. The results are a sweetener of 0 cal that is not digested. It is 600 times as sweet as sugar with a similar flavor profile. It is heat stable, readily soluble, and maintains its stability at elevated temperatures. It has been approved for use in specific categories that include baked products, beverages, confectioneries, and certain desserts and toppings.
3. Sucralose (1,6-dichloro-1,6-dideoxy-p-fructofuranosyl-4-chloro-oc- D-galactopyra- noside) is a nonnutritive sweetener based on sucrose. It is selectively chlorinated and the glycoside link between the two rings is resistant to hydrolysis by acid or enzymes, so it is not metabolized. It has 400 to 800 times the sweetness of sucrose, is very soluble in water, and is stable in heat. It can be used in food products that are baked or fried. Sucralose is produced by the selective chlorination of the sucrose molecule using a patented process by Tate and LyIe that replaces the three hydroxyl groups (OH) with three chlorine (Cl) atoms. This modified sugar is minimally absorbed by the body and passes out unchanged. It was approved for use in foods and beverages in 1999 in the United States.

Production Methods

Sucralose may be prepared by a variety of methods that involve the selective substitution of three sucrose hydroxyl groups by chlorine. Sucralose can also be synthesized by the reaction of sucrose (or an acetate) with thionyl chloride.

Definition

ChEBI: A disaccharide derivative consisting of 4-chloro-4-deoxy-alpha-D-galactopyranose and 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranose units linked by a glycosidic bond.

General Description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.Sucralose is a polar, chlorinated sugar synthesized from saccharose precursor. It is widely used as a sweetener in a number of food and beverage products.

Pharmaceutical Applications

Sucralose is used as a sweetening agent in beverages, foods, and pharmaceutical applications. It has a sweetening power approximately 300–1000 times that of sucrose and has no aftertaste. It has no nutritional value, is noncariogenic, does not promote dental caries, and produces no glycemic response.

Biochem/physiol Actions

A synthetic sweet tastant detectable by humans. Activates T1R2/T1R3 sweet taste receptors on enteroendocrine cells and elicits increased hormonal secretion of glucagon-like peptide-1 and glucose-dependent insulinotrophic peptide.

Safety

Sucralose is generally regarded as a nontoxic and nonirritant material and is approved, in a number of countries, for use in food products. Following oral consumption, sucralose is mainly unabsorbed and is excreted in the feces. The WHO has set an acceptable daily intake for sucralose of up to 15 mg/kg body-weight. LD50 (mouse, oral): > 16 g/kg LD50 (rat, oral): > 10 g/kg

storage

Sucralose is a relatively stable material. In aqueous solution, at highly acidic conditions (pH < 3), and at high temperatures (≤35℃), it is hydrolyzed to a limited extent, producing 4-chloro-4- deoxygalactose and 1,6-dichloro-1,6-dideoxyfructose. In food products, sucralose remains stable throughout extended storage periods, even at low pH. However, it is most stable at pH 5–6. Sucralose should be stored in a well-closed container in a cool, dry place, at a temperature not exceeding 21℃. Sucralose, when heated at elevated temperatures, may break down with the release of carbon dioxide, carbon monoxide, and minor amounts of hydrogen chloride.

Regulatory Status

The FDA, in April 1998, approved sucralose for use as a tabletop sweetener and as an additive in a variety of food products. In the UK, sucralose was fully authorized for use in food products in 2005. It is also accepted for use in many other countries worldwide. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.

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

Upstream product

• 63648-81-7 6-O-acetyl sucrose 
• 69-65-8 mannitol 
• 63648-85-1 6-acetyl sucrose 
• 63648-78-2 sucrose-6-acetate 
• 55832-20-7 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-β-D-fructofuranoside 
• 1445-45-0 Trimethyl orthoacetate 
• 104-15-4 toluene-4-sulfonic acid 
• 75-64-9 tert-butylamine 
• 57-50-1 Sucrose 
• 936001-72-8 sucrose-6-acetate 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 
• 105066-21-5 sucralose-6-acetate 

Downstream Products

• 55832-20-7 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-β-D-fructofuranoside 
• 129747-85-9 2,3-di-O-acetyl-6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-di-O-acetyl-1,6-dichloro-1,6-dideoxy-β-D-fructofuranoside 
• 82920-04-5 2,3-di-O-acetyl-6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-β-D-lyxo-hexulofuranoside 
• 82920-03-4 6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-β-D-lyxo-hexulofuranoside 
• 82919-99-1 6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-α-D-galactopyranosyl 1,6-dichloro-1,6-dideoxy-β-D-fructofuranoside 
• 82920-00-1 3,6-anhydro-4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-β-D-lyxo-hexulofuranoside 
• 82920-01-2 4-chloro-4-deoxy-α-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-β-D-lyxo-hexulofuranoside 

Relevant articles and documents

Bioconversion of sucralose-6-acetate to sucralose using immobilized microbial cells

Bioconversion of sucralose-6-acetate to sucralose, an artificial sweetener has been carried out using Arthrobacter sp. (ABL) and Bacillus subtilis (RRL-1789) strains isolated at IIIM, Jammu, India. Biotransformation of sucralose-6-acetate to sucralose involves use of microbial whole cells, immobilized whole cells and immobilized whole cell bioreactor. Immobilized whole cells packed bed reactor has shown much superior biotransformation process in aqueous system using green technology, where purification of the final product is not required. The final sucralose bioproduct was directly concentrated under vacuum to get white crystalline powder. The immobilized whole cell bioreactor was used for more than three cycles continuously, thus provided much cheaper, less time consuming and easy down streaming process. Moreover, the method does not require any purification steps, which is otherwise requisite for presently available methods for sucralose production, resulting in even lower cost of overall process.

A chlorinating agent preparation method and its method of preparing sucralose

The invention provides a preparation method of a novel chlorinating agent, which includes following steps: 1) dissolving an N,N-disubstituted formamide derivative in a nonprotic organic solvent and cooling the solution to 0 DEG C with stirring; 2) adding dropwisely thionyl chloride or oxalyl chloride to the solution obtained in the step 1) with dropwise addition temperature controlled to be 10-20 DEG C, heating the solution to 20-40 DEG C when the dropwise addition is finished, and performing a reaction for 1-2 h and cooling the solution to room temperature after the reaction finished; and 3) filtering the reaction product to obtain the chlorinating agent. The preparation method increases selectivity of a chlorination reaction, wherein the chlorination is carried out in a stepwise temperature increasing manner, so that yield of chlorination is greatly increased. The method solves difficulty of separation of the sucralose and reduces the production cost of the sucralose.

Recrystallization method of sucrose-6-acetate and applications thereof

The invention discloses a recrystallization method of sucrose-6-acetate, and applications thereof. The recrystallization method comprise following steps: a solvent is added into a sucrose-6-acetate mixture obtained via sucrose esterification; and stirring, dissolving, filtering, and drying are carried out so as to obtain sucrose-6-acetate, wherein the solvent is a mixture of a nitrile solvent and an ether solvent. The recrystallization method is capable of increasing sucrose-6-acetate purity, and reducing adverse influences on subsequent chlorination.

A method of preparing sucralose

The invention provides a modified synthetic technology for sucralose. Trimethyl orthoacetate and excess sucrose are subjected to a cyclization reaction in DMF for improving the utilization rate of high-price trimethyl orthoacetate, then a low-polarity solvent is added into the reaction solution so as to enable unreacted sucrose to be crystallized and precipitated from the reaction solution, after separation, the purity of sucrose-4,6-cyclic ester in the reaction solution is 95% or more; then through ring opening and acyl migration, the content of sucrose-6-ester in the reaction solution is 90% or more; the DMF solution of sucrose-6-ester is subjected to dewatering processing and then directly subjected to a next-step chlorination reaction, and the chlorination product is subjected to deacetylation by sodium methoxide so as to obtain sucralose; and unreacted sucrose can be recovered for using, and the reaction total yield, calculated based on sucrose, can reach 37% or more. Compared with conventional technology, the utilization rate of trimethyl orthoacetate in the technology is improved by 10% or more.

Deacylating method of sucralose-6-acetate

The invention discloses a deacylating method of sucralose-6-acetate, comprising the following steps: adding sucralose-6-acetate into methanol solution of sodium methylate, reacting at 58-62 DEG C for 3-5 hours, vacuum distilling and recycling methanol, and washing obtained solid with ethyl acetate to obtain sucralose. Compared with existing deacylating methods of sucralose-6-acetate, the method of the invention can be used to provide significant deacylating effect, and the yield of sucralose after deacylating is up to higher than 85%.

Trichlorosaccharose-6-acetate continuous deacetyl systems trichlorosaccharose method

The invention provides a method for preparing sucralose by continuously deacetylating sucralose-6-acetate. According to the method, in the presence of a basic catalyst, the sucralose-6-acetate is deacetylated to generate the sucralose, the catalyst is added in a segmented mode according to pH of a reaction solution, a novel reactor is adopted so that the catalyst can be rapidly mixed and dispersed, and the reaction temperature is easy to control. The synthetic sucralose has the advantages that residual quantity of the sucralose-6-acetate is small, the content of dichloro sucrose is low, the usage amount of the catalyst is small, the yield of the sucralose is high, continuous operation is achieved, the production cycle is shortened, and production cost is saved.

CHLORINATION OF SUCROSE-6-ESTERS

There is provided a method for the chlorination of a sucrose-6-acylate to produce a 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose-6-acylate, wherein said method comprises the following steps (i) to (v): (i) providing a first component comprising sucrose-6-acylate; (ii) providing a second component comprising a chlorinating agent; (iii) combining said first component and said second component to afford a mixture; (iv) heating said mixture for a heating period in order to provide chlorination of sucrose- 6-acylate at the 4, 1' and 6' positions thereof; (v) quenching said mixture to produce a 4,1',6'-trichloro-4,1',6'-trideoxy- galactosucrose-6-acylate; wherein at least one of said first component and said second component comprises a reaction vehicle, and said reaction vehicle comprises a tertiary amide; and wherein said mixture comprises a cosolvent during a least a portion of the heating period of step (iv), wherein said cosolvent comprises perfluorooctane.

PROCESS FOR THE PREPARATION OF SUCRALOSE

The present invention provides a method for preparing colorless sucralose, wherein 4,1′,6′-trichloro-4,1′,6′-trideoxy-galacto sucrose-6- acetate containing colored impurities formed during chlorination of sucrose-6-acetate is treated with sodium hypochlorite, where sodium hypochlorite acts both as a decolorizing agent and as a reagent for the ester hydrolysis.

Oral Solid Dosage Form Containing Nanoparticles and Process of Formulating the Same Using Fish Gelatin

An oral solid dosage form containing nanoparticles is made by (a) reducing the particle size of at least one pharmaceutically active ingredient dispersed in a solution containing fish gelatin to form a nanosuspension and (b) freeze-drying the nanosuspension of step (a) to form the oral solid dosage form.

Method of sucralose synthesis yield

The invention discloses a method for improving the yield of sucralose, including reacting sucrose to produce sucrose-6-acetate in the existence of an azo reagent as a catalyst and acetic acid as an acylating agent in a proper solvent; then reacting sucrose-6-acetate with a proper chlorinating agent to produce sucralose-6-acetate in a non-proton polar solvent with TCA as a catalyst; and at last, alcoholyzing sucralose-6-acetate in KOH/methanol to obtain sucralose.