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55589-62-3

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55589-62-3 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 55589-62-3 differently. You can refer to the following data:
1. White to Off-White Solid
2. Acesulfame potassium occurs as a colorless to white-colored, odorless, crystalline powder with an intensely sweet taste.

Originator

Acesulfame Potassium ,Hoechst

History

Acesulfame-K, the potassium salt of acesulfame, is a sweetener that resembles saccharin in structure and taste profile. 5,6-Dimethyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide, the first of many sweet compounds belonging to the dihydrooxathiazinone dioxide class, was discovered accidentally in 1967. From these many sweet compounds, acesulfame was chosen for commercialization. To improve water solubility, the potassium salt was made. Acesulfame-K (Sunett) was approved for dry product use in the United States in 1988 and in Canada in October, 1994. In 2003, acesulfame-K was approved as a general purposes sweetener by the FDA.

Uses

Different sources of media describe the Uses of 55589-62-3 differently. You can refer to the following data:
1. 'New generation', heat-stable sweetener that has not been suspected to cause cancer nor be genotoxic. Allelic variation of the Tas1r3 gene affects behavioral taste responses to this molecule, suggesting that it is a T1R3 receptor ligand.
2. Potassium salt as sweetener for foods, cosmetics.
3. Acesulfame-K is the potassium salt of 6-methyl-l,2,3-oxathiazin-4(3H)- one-2,2-dioxide. This sweetener was discovered in Germany and was first approved by the FDA in 1988 for use as a nonnutritive sweetener. The complex chemical name of this substance led to the creation of the trademark common name, acesulfame-K, which is based on its following relationships to acetocetic acid and sulfanic acid, and to its potassium salt nature. Acesulfame-K is 200 times as sweet as sugar and is not metabolized and is thus noncaloric. It is exceptionally stable at elevated temperatures encountered in baking, and it is also stable in acidic products, such as carbonated soft drinks. It has a synergistic effect when mixed with other low-calorie sweetners, such as aspartame. Common applications of acesulfame-K are table uses, chewing gums, beverages, foods, bakery products, confectionary, oral hygiene products, and pharmaceuticals.

Production Methods

Different sources of media describe the Production Methods of 55589-62-3 differently. You can refer to the following data:
1. Acesulfame potassium is synthesized from acetoacetic acid tertbutyl ester and fluorosulfonyl isocyanate. The resulting compound is transformed to fluorosulfonyl acetoacetic acid amide, which is then cyclized in the presence of potassium hydroxide to form the oxathiazinone dioxide ring system. Because of the strong acidity of this compound, the potassium salt is produced directly. An alternative synthesis route for acesulfame potassium starts with the reaction between diketene and amidosulfonic acid. In the presence of dehydrating agents, and after neutralization with potassium hydroxide, acesulfame potassium is formed.
2. The principal commercial process for acesulfame-K is depicted below:

Manufacturing Process

80 g (1.096 mol) of dimethylethylamine were added drop-wise, with cooling, to 80 g (0.825 mol) of sulfamic acid suspended in 500 ml of glacial acetic acid. When dissolution was complete, 80 ml (1.038 mol) of diketene were added, while cooling at 25°-35°C. After 16 hours, the mixture was evaporated and the residue was stirred with acetone, whereupon crystallization of dimethylethylammonium acetoacetamide-N-sulfonate took place. Yield: 110 g (43%), melting point 73°-75°C. 12.7 g (50 mmol) of dimethylethylammonium acetoacetamide-N-sulfonate in 110 ml of methylene chloride were added drop-wise to 8 ml (200 mmol) of liquid SO3 in 100 ml of CH2Cl2 at -30°C, stirring vigorously, within 60 minutes. 30 minutes later, 50 ml of ethyl acetate and 50 g of ice were added to the solution. The organic phase was separated off, and the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were dried over sodium sulfate, evaporated and the residue was dissolved in methanol. On neutralization of the solution with methanolic KOH, the potassium salt of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide precipitated out. Yield: 7.3 g (73%). The product was detected by thinlayer chromatography; the structure of it was confirmed with IR spectrum.

Pharmaceutical Applications

Acesulfame potassium is used as an intense sweetening agent in cosmetics, foods, beverage products, table-top sweeteners, vitamin and pharmaceutical preparations, including powder mixes, tablets, and liquid products. It is widely used as a sugar substitute in compounded formulations,and as a toothpaste sweetener. The approximate sweetening power is 180–200 times that of sucrose, similar to aspartame, about one-third as sweet as sucralose, one-half as sweet as sodium saccharin, and about 4-5 times sweeter than sodium cyclamate.It enhances flavor systems and can be used to mask some unpleasant taste characteristics.

Safety Profile

When heated to decompositionemits toxic fumes of SOx.

Safety

Acesulfame potassium is widely used in beverages, cosmetics, foods, and pharmaceutical formulations, and is generally regarded as a relatively nontoxic and nonirritant material. Pharmacokinetic studies have shown that acesulfame potassium is not metabolized and is rapidly excreted unchanged in the urine. Long-term feeding studies in rats and dogs showed no evidence to suggest acesulfame potassium is mutagenic or carcinogenic. The WHO has set an acceptable daily intake for acesulfame potassium of up to 15 mg/kg body-weight.The Scientific Committee for Foods of the European Union has set a daily intake value of up to 9 mg/kg of body-weight. LD50 (rat, IP): 2.2 g/kg LD50 (rat, oral): 6.9–8.0 g/kg

storage

Acesulfame potassium possesses good stability. In the bulk form it shows no sign of decomposition at ambient temperature over many years. In aqueous solutions (pH 3.0–3.5 at 208℃) no reduction in sweetness was observed over a period of approximately 2 years. Stability at elevated temperatures is good, although some decomposition was noted following storage at 408℃ for several months. Sterilization and pasteurization do not affect the taste of acesulfame potassium. The bulk material should be stored in a well-closed container in a cool, dry place and protected from light.

Regulatory Status

Included in the FDA Inactive Ingredients Database for oral and sublingual preparations. Included in the Canadian List of Acceptable Non-medicinal Ingredients. Accepted for use in Europe as a food additive. It is also accepted for use in certain food products in the USA and several countries in Central and South America, the Middle East, Africa, Asia, and Australia.

Check Digit Verification of cas no

The CAS Registry Mumber 55589-62-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,5,5,8 and 9 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 55589-62:
(7*5)+(6*5)+(5*5)+(4*8)+(3*9)+(2*6)+(1*2)=163
163 % 10 = 3
So 55589-62-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1/p-1

55589-62-3 Well-known Company Product Price

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  • Supelco

  • (47134)  AcesulfameK  analytical standard

  • 55589-62-3

  • 000000000000047134

  • 257.40CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1266)  AcesulfameK  pharmaceutical secondary standard; traceable to USP and PhEur

  • 55589-62-3

  • PHR1266-500MG

  • 804.73CNY

  • Detail
  • Sigma-Aldrich

  • (A0070000)  Acesulfamepotassium  European Pharmacopoeia (EP) Reference Standard

  • 55589-62-3

  • A0070000

  • 1,880.19CNY

  • Detail
  • USP

  • (1002505)  Acesulfamepotassium  United States Pharmacopeia (USP) Reference Standard

  • 55589-62-3

  • 1002505-200MG

  • 7,733.70CNY

  • Detail

55589-62-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Acesulfame potassium

1.2 Other means of identification

Product number -
Other names ace-SUHL-faym

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:55589-62-3 SDS

55589-62-3Synthetic route

Triethylammoniumsalz der Acetoacetamid-N-sulfonsaeure
99911-48-5

Triethylammoniumsalz der Acetoacetamid-N-sulfonsaeure

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
Stage #1: Triethylammoniumsalz der Acetoacetamid-N-sulfonsaeure With sulfur trioxide In dichloromethane; water at 100℃; under 75007.5 Torr; for 2.77778E-06h;
Stage #2: With potassium hydroxide In water at 50℃; for 0.1h; Pressure; Temperature;
85%
Stage #1: Triethylammoniumsalz der Acetoacetamid-N-sulfonsaeure With sulfur trioxide In dichloromethane at 1.5 - 4.5℃;
Stage #2: With potassium hydroxide In water Temperature;
56.7%
Yield given. Multistep reaction;
Stage #1: Triethylammoniumsalz der Acetoacetamid-N-sulfonsaeure With sulfur trioxide In dichloromethane at -35 - -25℃; for 0.0833333h;
Stage #2: With water In dichloromethane at -22 - 20℃;
Stage #3: With potassium hydroxide In dichloromethane; water at 24 - 26℃; Time; Temperature; Reagent/catalyst;
With sulfur trioxide In dichloromethane at 11℃;
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
Stage #1: 4-methyleneoxetan-2-one With aminosulfonic acid; triethylamine In dichloromethane at 20 - 25℃; for 0.00833333h;
Stage #2: With sulfur trioxide In dichloromethane at 20 - 40℃; under 0 - 7500.75 Torr;
Stage #3: With potassium hydroxide In dichloromethane; water Temperature;
85%
acetoacetamido
5977-14-0

acetoacetamido

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
Yield given. Multistep reaction;
fluorosulfonyl fluoride
640723-20-2, 2699-79-8, 12769-73-2

fluorosulfonyl fluoride

methanolic KOH

methanolic KOH

acetoacetamido
5977-14-0

acetoacetamido

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
With triethylamine In acetonitrile
methanolic KOH

methanolic KOH

acetoacetamido
5977-14-0

acetoacetamido

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
With triethylamine In acetonitrile
acetosulfam
33665-90-6

acetosulfam

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 35℃; Product distribution / selectivity;
C4H5NO4S*4O3S

C4H5NO4S*4O3S

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
Stage #1: C4H5NO4S*4O3S With water In dichloromethane at -22 - -5℃; for 0.166667h;
Stage #2: With potassium hydroxide In dichloromethane; water at 24 - 26℃; for 0.333333h;
acetosulfam
33665-90-6

acetosulfam

A

5-chloroacesulfame potassium

5-chloroacesulfame potassium

B

potassium acesulfame
55589-62-3

potassium acesulfame

Conditions
ConditionsYield
With potassium hydroxide at 25℃; for 0.333333h;
potassium acesulfame
55589-62-3

potassium acesulfame

oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

oxybuprocaine acesulfamate

oxybuprocaine acesulfamate

Conditions
ConditionsYield
In ethanol at 20℃;100%
N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-octylguanidinium chloride
1260486-47-2

N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-octylguanidinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-octylguanidinium acesulfamate
1260486-62-1

N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-octylguanidinium acesulfamate

Conditions
ConditionsYield
In water at 60℃;99%
potassium acesulfame
55589-62-3

potassium acesulfame

epinephrine hydrochloride
55-31-2

epinephrine hydrochloride

epinephrine acesulfamate

epinephrine acesulfamate

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;99%
potassium acesulfame
55589-62-3

potassium acesulfame

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium 6-methyl-1,2,3-oxathiazin-4-olate 2,2-dioxide

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium 6-methyl-1,2,3-oxathiazin-4-olate 2,2-dioxide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;98%
N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-decylguanidinium chloride
1260486-48-3

N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-decylguanidinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-decylguanidinium acesulfamate
1260486-63-2

N,N-diethyl-N',N'-di-n-propyl-N''-n-hexyl-N''-n-decylguanidinium acesulfamate

Conditions
ConditionsYield
In water at 60℃;97%
potassium acesulfame
55589-62-3

potassium acesulfame

mepivacaine hydrochloride
1722-62-9

mepivacaine hydrochloride

mepivacaine acesulfamate

mepivacaine acesulfamate

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;97%
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

water
7732-18-5

water

potassium acesulfame
55589-62-3

potassium acesulfame

cobalt(II) perchlorate hexahydrate

cobalt(II) perchlorate hexahydrate

C10H20CoN4O4(2+)*2C4H4NO4S(1-)*2H2O

C10H20CoN4O4(2+)*2C4H4NO4S(1-)*2H2O

Conditions
ConditionsYield
In ethanol at 65 - 75℃; for 6h; High pressure;92%
Dodecyl-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-dimethyl-ammonium; chloride

Dodecyl-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-dimethyl-ammonium; chloride

potassium acesulfame
55589-62-3

potassium acesulfame

butyldimethyl[(1R,2S,5R)-(-)menthoxymethyl]ammonium acesulfamate

butyldimethyl[(1R,2S,5R)-(-)menthoxymethyl]ammonium acesulfamate

Conditions
ConditionsYield
In water at 20℃; for 2h;91.5%
3-hydroxy-1-pentyloxymethylpyridinium chloride
454234-72-1

3-hydroxy-1-pentyloxymethylpyridinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

3-hydroxy-1-pentyloxymethylpyridinium acesulfamate
1127350-75-7

3-hydroxy-1-pentyloxymethylpyridinium acesulfamate

Conditions
ConditionsYield
In water for 26h;91%
1-butoxymethyl-3-hydroxypyridinium chloride
454234-71-0

1-butoxymethyl-3-hydroxypyridinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

1-butoxymethyl-3-hydroxypyridinium acesulfamate
1127350-74-6

1-butoxymethyl-3-hydroxypyridinium acesulfamate

Conditions
ConditionsYield
In water for 26h;91%
3-hydroxy-1-propoxymethylpyridinium chloride
454234-70-9

3-hydroxy-1-propoxymethylpyridinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

3-hydroxy-1-propoxymethylpyridinium acesulfamate
1127350-73-5

3-hydroxy-1-propoxymethylpyridinium acesulfamate

Conditions
ConditionsYield
In water for 26h;90%
3-hydroxy-1-undecyloxymethylpyridinium chloride
454234-78-7

3-hydroxy-1-undecyloxymethylpyridinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

3-hydroxy-1-undecyloxymethylpyridinium acesulfamate
1127350-78-0

3-hydroxy-1-undecyloxymethylpyridinium acesulfamate

Conditions
ConditionsYield
In water for 26h;90%
zinc perchlorate

zinc perchlorate

potassium acesulfame
55589-62-3

potassium acesulfame

acesulfame zinc

acesulfame zinc

Conditions
ConditionsYield
In water Cooling with ice;90%
sodium tetrachloropalladate

sodium tetrachloropalladate

potassium acesulfame
55589-62-3

potassium acesulfame

dipotassium-tetrakis[6-methyl-1,2,3-oxathiazine-4(3H)-one-3-ato-2,2-dioxide]palladate(II)

dipotassium-tetrakis[6-methyl-1,2,3-oxathiazine-4(3H)-one-3-ato-2,2-dioxide]palladate(II)

Conditions
ConditionsYield
In water soln. of Na2PdCl4 and the oxathiazine-dioxide in 3 ml H2O stirred (12 h, room temp.); ppt. sucked off, washed with H2O and EtOH, dried (vac.); elem. anal.;89%
N,N-diethyl-N',N'-di-n-propyl-N'',N''-di-n-hexylguanidinium chloride
1260486-46-1

N,N-diethyl-N',N'-di-n-propyl-N'',N''-di-n-hexylguanidinium chloride

potassium acesulfame
55589-62-3

potassium acesulfame

N,N-diethyl-N',N'-di-n-propyl-N'',N''-di-n-hexyl-guanidinium acesulfamate
1260486-61-0

N,N-diethyl-N',N'-di-n-propyl-N'',N''-di-n-hexyl-guanidinium acesulfamate

Conditions
ConditionsYield
In water at 60℃;88%
potassium acesulfame
55589-62-3

potassium acesulfame

dimethyl dodecyl 3-hydroxypropyl ammonium bromide

dimethyl dodecyl 3-hydroxypropyl ammonium bromide

C17H38NO(1+)*C4H4NO4S(1-)

C17H38NO(1+)*C4H4NO4S(1-)

Conditions
ConditionsYield
In ethanol at 60℃; for 24h;88%
potassium acesulfame
55589-62-3

potassium acesulfame

N-(3-(diethoxyphosphoryl)propyl)-N,N-dimethyloctadecan-1-ammonium bromide

N-(3-(diethoxyphosphoryl)propyl)-N,N-dimethyloctadecan-1-ammonium bromide

N-(3-(diethoxyphosphoryl) propyl)-N,N-dimethyloctadecan-1-aminium-6-methyl-4-oxo-4H-1,2,3-oxathiazin-3-ide-2,2-dioxide

N-(3-(diethoxyphosphoryl) propyl)-N,N-dimethyloctadecan-1-aminium-6-methyl-4-oxo-4H-1,2,3-oxathiazin-3-ide-2,2-dioxide

Conditions
ConditionsYield
In ethanol at 60℃; for 24h;88%
potassium acesulfame
55589-62-3

potassium acesulfame

3'-nitro-2-bromoacetophenone
2227-64-7

3'-nitro-2-bromoacetophenone

6-methyl-3-[2-(3-nitrophenyl)-2-oxoethyl]-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide
1621619-40-6

6-methyl-3-[2-(3-nitrophenyl)-2-oxoethyl]-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;87%
C16H36NO2(1+)*Br(1-)

C16H36NO2(1+)*Br(1-)

potassium acesulfame
55589-62-3

potassium acesulfame

dodecyl(2-(2-hydroxyethoxy)ethyl)dimethylammonium acesulfame

dodecyl(2-(2-hydroxyethoxy)ethyl)dimethylammonium acesulfame

Conditions
ConditionsYield
In methanol at 40℃; for 24h;87%
C20H44NO2(1+)*Br(1-)

C20H44NO2(1+)*Br(1-)

potassium acesulfame
55589-62-3

potassium acesulfame

hexadecyl(2-(2-hydroxyethoxy)ethyl)dimethylammonium acesulfame

hexadecyl(2-(2-hydroxyethoxy)ethyl)dimethylammonium acesulfame

Conditions
ConditionsYield
In methanol at 40℃; for 24h;86%

55589-62-3Relevant articles and documents

A new method for the preparation of 6-Methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide, Potassium salt (acesulfame K)

Linkies,Reuschling

, p. 405 - 406 (1990)

A simple two-step synthesis of the title compound, an artificial sweetener, starting from amidosulfonic acid and diketene is described.

Potassium acetylsulfamate composition

-

Paragraph 0076; 0083-0088, (2021/09/29)

The invention discloses an acesulfame potassium composition, comprising potassium acetylsulfamate and potassium acetylsulfamate, wherein the content of chloride of potassium acetylsulfamate is less 300 ppm. The composition is prepared by adding triethylamine in an amino sulfonic acid solution to carry out amination reaction, and generating an amino sulfonic acid ammonium salt solution. A diketene is added to an ammonium sulfamate solution, acylation reaction is carried out under the action of a solid acid catalyst, and an intermediate solution is obtained. The intermediate solution and the cyclization agent solution are subjected to sulphonation cyclization reaction under the action of a supported solid alkali heterogeneous catalyst to obtain a sulfonated cyclization product, and Hydrolysis step and salt formation step, the potassium acetylsulfamate composition with extremely low impurity content can be prepared through combination of the two catalysts, so that the process of post-treatment of the potassium acetylsulfanilamide is reduced to a great extent, and the production cost of potassium acetylsulfanilate is reduced.

Preparation method of acesulfame potassium composition

-

Paragraph 0072; 0075-0084, (2021/10/30)

The invention relates to a preparation method of an acesulfame potassium composition. According to the preparation method, a proper amount of organic acid is added to adjust the pH value of a neutralization reaction solution so as to change the pH value of an acetoacesulfame triethylamine salt solution generated by acylation reaction, so that the subsequent cyclization hydrolysis yield is increased to 95% or above, and therefore, the chromatic value of the acesulfame potassium composition finished product is influenced, and the product quality is improved.

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