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Acesulfame potassium structure
Acesulfame potassium structure

Acesulfame potassium

Iupac Name:potassium;6-methyl-2,2-dioxo-1-oxa-2$l^{6}-thia-3-azanidacyclohex-5-en-4-one
CAS No.:55589-62-3
Molecular Weight:201.237
Introduction: '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.
1. Names and Identifiers
1.1 Name
Acesulfame potassium
1.2 Synonyms

1,2,3-Oxathiazin-4(3H)-one, 6-methyl-, 2,2-dioxide, potassium salt 1,2,3-Oxathiazin-4(3H)-one, 6-methyl-, 2,2-dioxide, potassium salt (1:1) 1,2,3-oxathiazin-4-ol, 6-methyl-, 2,2-dioxide, potassium salt (1:1) 6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide potassium salt 6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide, potassium salt ace-SUHL-faym Acesulfame potassium salt Acesulfame-K Acesulfam-K Acesulfaml-K ACESULPHAME-K EINECS 259-715-3 MFCD00043833 Potassium 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide Potassium 6-methyl-4-oxo-4H-1,2,3-oxathiazin-3-ide 2,2-dioxide Potassium acesulfame potassiumacesulfame SUNETTE SWEET ONE

1.3 CAS No.
55589-62-3
1.4 CID
11074431
1.5 EINECS(EC#)
259-715-3
1.6 Molecular Formula
C4H4KNO4S (isomer)
1.7 Inchi
InChI=1S/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1/p-1
1.8 InChkey
WBZFUFAFFUEMEI-UHFFFAOYSA-M
1.9 Canonical Smiles
CC1=CC(=O)[N-]S(=O)(=O)O1.[K+]
1.10 Isomers Smiles
CC1=CC(=O)[N-]S(=O)(=O)O1.[K+]
2. Properties
3.1 Density
1.512
3.2 Melting Point
229-232℃ (dec.)
3.3 Boiling Point
332.7°C at 760 mmHg
3.4 Flash Point
155°C
3.5 Appearance
White, odorless, free flowing crystalline powder
3.6 Chemical Properties
White to Off-White Solid
3.7 Color/Form
White crystalline solid
3.8 Odor
odorless with sweet taste
3.9 StorageTemp
0-6°C
3.10 Water Solubility
Soluble
3. Use and Manufacturing
4.1 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.
4.2 Produe Method
Acesulfame potassium is synthesized from acetoacetic acid tertbutylester and fluorosulfonyl isocyanate. The resulting compoundis transformed to fluorosulfonyl acetoacetic acid amide, which isthen cyclized in the presence of potassium hydroxide to form theoxathiazinone dioxide ring system. Because of the strong acidity ofthis compound, the potassium salt is produced directly.An alternative synthesis route for acesulfame potassium startswith the reaction between diketene and amidosulfonic acid. In thepresence of dehydrating agents, and after neutralization withpotassium hydroxide, acesulfame potassium is formed.
4.3 Safety Profile
When heated to decompositionemits toxic fumes of SOx.
4.4 Usage
'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.
4. Safety and Handling
5.1 Risk Statements
R36/37/38
5.2 Safety Statements
S26
5.3 Transport
25kgs
5.4 Safety

Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements 26-36/37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
WGK Germany: 1
RTECS: RP4489165
As?with aspartame,sucralose,saccharin, and other sweeteners that are sweeter than common sugars, there is concern over the safety of acesulfame potassium. Although studies of these sweeteners show varying and controversial degrees of dietary safety,USFDA (the United States Food and Drug Administration) has approved these for use as general-purpose sweetening agents. Critics of the use of acesulfame potassium say the chemical has not been studied adequately and may be carcinogenic, although these claims have been dismissed by the USFDA and by equivalent authorities in the European Union.
Based largely on animal studies,Several potential problems associated with the use of acesulfame have been raised:
1. been shown to stimulate insulin secretion in rats in a dose dependent fashion thereby possibly aggravating reactive hypoglycemia ("low blood sugar attacks").
2.?no increased incidence of tumors in response to administration of acesulfame K.

5.5 Specification

White to Off-White Solid
usageEng:'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.
Safety Statements:26-36/37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
5.6 Toxicity
LD50 in rats (mg/kg): 7431 orally, 2243 i.p. (Mayer, Kemper)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

8. Precursor and Product
9. Computational chemical data
  • Molecular Weight:201.237g/mol
  • Molecular Formula:C4H4KNO4S
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:200.94981027
  • Monoisotopic Mass:200.94981027
  • Complexity:288
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:5
  • Topological Polar Surface Area:69.8
  • Heavy Atom Count:11
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:2
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