Acesulfame potassium Chemical Properties

Melting point:

229-232°C (dec.)

Boiling point:

210℃[at 101 325 Pa]

Density 

(solid) 1.81 g/cm3; d (bulk) 1.1-1.3 kg/dm3

vapor pressure 

0.291Pa at 25℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in water, very slightly soluble in acetone and in ethanol (96 per cent).

form 

Solid

color 

White crystalline solid

Odor

odorless with sweet taste

Odor Type

odorless

Water Solubility 

almost transparency

Merck 

14,37

BRN 

3637857

LogP

-2.35 at 23℃

CAS DataBase Reference

55589-62-3(CAS DataBase Reference)

EPA Substance Registry System

Acesulfame-potassium (55589-62-3)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

1

RTECS 

RP4489165

HS Code 

2934990002

Toxicity

LD50 in rats (mg/kg): 7431 orally, 2243 i.p. (Mayer, Kemper)

MSDS

• Language:English Provider:SigmaAldrich

Acesulfame potassium Usage And Synthesis

Description

Acesulfame potassium is approved for use in food as a sweetener. It is included in the ingredient list on the food label as acesulfame K, acesulfame potassium, or Ace-K.  Acesulfame potassium (Ace-K) is regulates  as a food additive. The FDA approved acesulfame potassium for use in specific food and beverage categories in 1988 and in 2003 approved it as a general-purpose sweetener and flavor enhancer in food, except in meat and poultry, under certain conditions of use.  It is widely used in the food industry, such as mouthwash and soft drinks. However, some researches have found that it does harm to the liver and nervous system[1-2].

Chemical Properties

White to Off-White Solid

Chemical Properties

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

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.

Uses

'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.

Uses

Potassium salt as sweetener for foods, cosmetics.

Production Methods

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.

Definition

ChEBI: Acesulfame k is a sulfuric acid derivative.

Production Methods

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.

brand name

Sunett? and Sweet One?

Therapeutic Function

Pharmaceutic aid

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.

Biological Activity

In rats, Acesulfame potassium (AceK) consumption from in-utero to post-weaning stages accelerated puberty onset, accompanied by increased brain gonadotropin-releasing hormone (GnRH) expression.  Intracerebroventricular AceK injection also induced early puberty onset in rats. In N44 hypothalamic neuron cells, AceK treatment increased reactive oxygen species production, which led to protein kinase A (PKA) activation and increased GnRH expression[1].

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.

References

[1] Wu H, et al. Consumption of the nonnutritive sweetener acesulfame potassium increases central precocious puberty risk. Journal of Hazardous Materials, 2023; 461: 132529.
[2] Duan X, et al. Detection of acesulfame potassium in mouthwash based on surface-enhanced Raman spectroscopy. Optical Engineering, 2018; 57: 057102 .

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