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Chemistry

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Also known as: 33665-90-6, Acetosulfam, 6-methyl-1,2,3-oxathiazin-4(3h)-one 2,2-dioxide, Acesulfamum, Acesulfamo, 6-methyl-2,2-dioxooxathiazin-4-one
Molecular Formula
C4H5NO4S
Molecular Weight
163.15  g/mol
InChI Key
YGCFIWIQZPHFLU-UHFFFAOYSA-N
FDA UNII
MA3UYZ6K1H

Acesulfamo
1 2D Structure

Acesulfamo

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-methyl-2,2-dioxooxathiazin-4-one
2.1.2 InChI
InChI=1S/C4H5NO4S/c1-3-2-4(6)5-10(7,8)9-3/h2H,1H3,(H,5,6)
2.1.3 InChI Key
YGCFIWIQZPHFLU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=O)NS(=O)(=O)O1
2.2 Other Identifiers
2.2.1 UNII
MA3UYZ6K1H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acesulfam-k

2. Acesulfame Calcium

3. Acesulfame K

4. Acesulfame Potassium

5. Acesulfame Sodium

6. Acetosulfam

7. Acetosulfam Potassium

8. Acetosulfam, Potassium Salt

9. Acetosulfam, Sodium Salt

10. Acetosulfame

11. Acetosulfame Calcium

2.3.2 Depositor-Supplied Synonyms

1. 33665-90-6

2. Acetosulfam

3. 6-methyl-1,2,3-oxathiazin-4(3h)-one 2,2-dioxide

4. Acesulfamum

5. Acesulfamo

6. 6-methyl-2,2-dioxooxathiazin-4-one

7. 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide

8. Chebi:83501

9. Acesulfame Potassium

10. Ma3uyz6k1h

11. 6-methyl-1,2,3-oxathiazin-4(3h)-on 2,2-dioxid

12. 1,2,3-oxathiazin-4(3h)-one, 6-methyl-, 2,2-dioxide

13. 3,4-dihydro-6-methyl-1,2,3-oxathiazin-4-one 2,2-dioxide

14. 3,4-dihydro-6-methyl-1,2,3-oxathiazin-4-one-2,2-dioxide

15. Acesulfame-potassium

16. Acetosulfame

17. Acesulfame [ban:inn]

18. Acesulfame [inn:ban]

19. Acesulfamum [inn-latin]

20. Unii-ma3uyz6k1h

21. Acesulfamo [inn-spanish]

22. Hsdb 3914

23. Aud

24. Acesulfame Form Ii

25. Einecs 251-622-6

26. Acesulfame [ii]

27. Acesulfame [mi]

28. Acesulfame [inn]

29. Acesulfame [hsdb]

30. Schembl3551

31. Acesulfame [who-dd]

32. Chembl176687

33. Dtxsid0048006

34. Schembl12166504

35. 6-methyl-2h-1,2lambda~6~,3-oxathiazine-2,2,4(3h)-trione

36. 6-methyl-3,4-dihydro-1,2lambda6,3-oxathiazine-2,2,4-trione

37. Zinc2009976

38. Bbl036697

39. Bdbm50367132

40. Stl559076

41. Akos006273139

42. Vs-13634

43. Ft-0652563

44. E80533

45. Q2823822

46. 6-methyl-1,2,3-oxathiazin-4(3h)-one 2,2-dioxide, 9ci

47. 6-methyl-3,4-dihydro-1,2??,3-oxathiazine-2,2,4-trione

48. [4(3h)-oxo-6-methyl-1,2,3-oxathiazine 2,2-dioxide]-3-ide

49. 6-methyl-3,4-dihydro-1,2$l^{6},3-oxathiazine-2,2,4-trione

50. 6-methyl-3,4-dihydro-1,2,3-oxa-thiazin-4-one 2,2-dioxide

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 163.15 g/mol
Molecular Formula C4H5NO4S
XLogP3-0.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass162.99392881 g/mol
Monoisotopic Mass162.99392881 g/mol
Topological Polar Surface Area80.8 Ų
Heavy Atom Count10
Formal Charge0
Complexity283
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

/MILK/ Nonnutritive sweeteners (NNS), including saccharin, sucralose, aspartame, and acesulfame-potassium, are commonly consumed in the general population, and all except for saccharin are considered safe for use during pregnancy and lactation. Sucralose (Splenda) currently holds the majority of the NNS market share and is often combined with acesulfame-potassium in a wide variety of foods and beverages. To date, saccharin is the only NNS reported to be found in human breast milk after maternal consumption, while there is no apparent information on the other NNS. Breast milk samples were collected from 20 lactating volunteers, irrespective of their habitual NNS intake. Saccharin, sucralose, and acesulfame-potassium were present in 65% of participants' milk samples, whereas aspartame was not detected. These data indicate that NNS are frequently ingested by nursing infants, and thus prospective clinical studies are necessary to determine whether early NNS exposure via breast milk may have clinical implications. /Acesulfame potassium/

PMID:26267522 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5583633 Sylvetsky AC et al; J Toxicol Environ Health A 78 (16): 1029-32 (2015)


Single oral doses of 10 mg (14)C-Acesulfame K/kg bw given to rats and dogs were rapidly absorbed. Maximum blood levels reached were 0.75 plus or minus 0.2 g/mL in rats, 0.5 hr after dosing, and 6.56 plus or minus 2.08 g/mL in dogs, 1-1.5 hr after dosing. In rats, 82-100% of the dose, and in dogs, 85-100% of the dose was excreted in the urine; in both species, 97-100% of the total radioactivity was excreted in feces, and total recovery approximated 100%. Rats given 10 consecutive daily doses of 10 mg/kg orally did not show evidence of accumulation. Three days after dosing, the concn in the organs and plasma was 0.4 nMol/g in liver, and <0.2 nMol/g in other tissues. Seven days after dosing, the concn in dogs was <0.2 nMol/g in all tissues examined. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


After pretreatment for seven days with a diet containing 3% Acesulfame K, male rats were given a dose of 250 mg Acesulfame K containing (14)C-Acesulfame K (9.6 x 108 dpm) by oral gavage. After eight hours the animals were killed and liver and spleen excised; DNA and chromatin protein was isolated from these organs. No radioactivity could be detected on any DNA sample. A low level of activity (8-11 dpm/mg protein) was associated with chromatin protein and this was claimed to be due to non-covalent interactions of unchanged Acesulfame K. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


Single oral doses of approximately 15 mg (14)C-Acesulfame K/kg bw were administered to male and female rats which had been pretreated with unlabeled Acesulfame K at a level of 300 mg/kg diet for 60 days. Control animals without pretreatment were also similarly dosed with (14)C-Acesulfame K. In all animals 95.1-98.2% of the dose was recovered in urine and cage washings and 0.95-2.86% in feces. Total recoveries were 96.3-99.2%. Excretion of radioactivity was rapid and displayed biphasic kinetics; 92.6-96.8% of the dose was excreted in 24 hours. ... No significant differences in route or rate of excretion were observed between sexes nor between controls and animals pretreated with Acesulfame K for 60 days. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


For more Absorption, Distribution and Excretion (Complete) data for Acesulfame (8 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

The metabolism of Acesulfame K was investigated in the urine and feces of rats and dogs which had received single oral doses of 10 mg/kg bw, and in the urine and bile of pigs dosed orally with 5 mg/kg bw. The analytical methods used (thin-layer chromatography, mass spectrometry and isotope dilution) detected only the original substance in these samples. Separation by TLC of urinary extracts from rats used in the above study revealed only one peak which was identical with Acesulfame K. No metabolites were detected in control or Acesulfame K-pretreated animals. Similarly, no metabolites were detected in animals which had been pretreated with 1% Acesulfame K for 7 days. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


The metabolism of Acesulfame K was studied in serum and urine from human volunteers following a single dose of 30 mg/individual. Only the original substance was detected in all samples. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


4.3 Biological Half-Life

/After/ single oral doses of approximately 15 mg (14)C-Acesulfame K/kg bw were administered to male and female rats which had been pretreated with unlabeled Acesulfame K at a level of 300 mg/kg diet for 60 days; ... the half-life of the rapid phase was 4-4.5 hours and of the slower phase (accounting for <0.5% of the dose) was 109-257 hours. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


After iv admin of a single dose of 10 mg (14C)-Acesulfame K/kg bw to rats, the radioactivity was excreted quantitatively in urine and the plasma half-life was 0.23 hr. /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


In lactating rats given a single oral dose of (14)C-Acesulfame K of about 10.6 mg/kg bw, ...the biological half-lives were similar in milk (5.6 hr) and blood (4 hr). /Acesulfame K/

WHO Food Additive Series 28: Acesulfame Potassium (1990). Available from, as of October 30, 2017: https://www.inchem.org/documents/jecfa/jecmono/v28je13.htm


The purpose of this work was...the determination of acesulfame-K (AcK) in C57BL mouse plasma and urine. Male and female animals were dosed orally (gavage) and intravenously at 10 mg/kg and then plasma and urine collected at up to 24 hours post dose. Plasma samples were analyzed with an HPLC method... and urine was analyzed with a second HPLC method .... Both methods used saccharin as internal standard with detection by UV absorbance at 230 nm. Following IV administration, plasma AcK concentrations declined rapidly and linearly within 120 min and a second AcK peak was observed at 240 minutes. Half-life was estimated to be 11-15 minutes. Plasma concentrations of AcK reached maximal levels within 45 minutes and rapidly declined following oral doses. Plasma AcK were below limits of detection by 480 minutes post dose. A second peak was also observed following oral administration, suggesting enterohepatic recirculation. Following IV and PO administration, 45% (males) and 70% (females) of the dose was excreted in urine by 24 hr. Oral bioavailability was estimated to be 90-100% based on urinary data.

Lodge J, et al; Toxicol Sci 90 (1-S): 117 (2006)


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27-Jan-2021
24-Oct-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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