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Details

Stereochemistry ACHIRAL
Molecular Formula C4H5NO4S
Molecular Weight 163.152
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACESULFAME

SMILES

CC1=CC(=O)NS(=O)(=O)O1

InChI

InChIKey=YGCFIWIQZPHFLU-UHFFFAOYSA-N
InChI=1S/C4H5NO4S/c1-3-2-4(6)5-10(7,8)9-3/h2H,1H3,(H,5,6)

HIDE SMILES / InChI

Molecular Formula C4H5NO4S
Molecular Weight 163.152
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Acesulfame is a non-nutritive sweetener Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K (K being the symbol for potassium), and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number (additive code) E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova). In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3- oxathiazine-4(3H)-one 2,2-dioxide. Acesulfame K has been approved for a variety of uses in more than 90 countries. In 1998, the FDA broadened the US approval of acesulfame K to allow its use in nonalcoholic beverages. It is often blended with sucralose and used to decrease the bitter aftertaste of aspartame. A wide range of low-calorie foods and drinks contain acesulfame K, including table-top sweeteners, chewing gum, jam, dairy products, frozen desserts, drinks and baked goods. Acesulfame K is not broken down when digested, nor is it stored in the body. After being consumed, it is quickly absorbed by the body and then rapidly excreted, unchanged.

Originator

Curator's Comment: Acesulfame potassium was developed after the accidental discovery of a similar compound (5,6-dimethyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide) in 1967 by Karl Clauss and Harald Jensen at Hoechst AG.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.41 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Acesulfame K

Approved Use

Nonnutritive sweetener

Launch Date

1988
PubMed

PubMed

TitleDatePubMed
Calculation of the intake of three intense sweeteners in young insulin-dependent diabetics.
2001 Jul
[Simultaneous determination of various food additives by high performance liquid chromatography].
2001 Mar
Fluoride concentration and pH of iced tea products.
2002 Nov-Dec
Determination of acesulfame and sucralose in oral electrolyte maintenance solution by liquid chromatography.
2003 Jan-Feb
Comparison of the responses of the chorda tympani and glossopharyngeal nerves to taste stimuli in C57BL/6J mice.
2003 Mar 4
The powder flow and compact mechanical properties of sucrose and three high-intensity sweeteners used in chewable tablets.
2003 May 12
Dietary estimated intake of intense sweeteners by Italian teenagers. Present levels and projections derived from the INRAN-RM-2001 food survey.
2004 Apr
Sweet success: Ionic liquids derived from non-nutritive sweeteners.
2004 Mar 21
Bitter taste receptors for saccharin and acesulfame K.
2004 Nov 10
The cysteine-rich region of T1R3 determines responses to intensely sweet proteins.
2004 Oct 22
[Analysis of nine kinds of sweeteners in foods by LC/MS].
2005 Jun
Haplotypes at the Tas2r locus on distal chromosome 6 vary with quinine taste sensitivity in inbred mice.
2005 Jun 6
Bis(acesulfamato-kappa2N3,O4)bis(2-aminopyrimidine-kappaN1)copper(II).
2005 May
NTP toxicology studies of acesulfame potassium (CAS No. 55589-62-3) in genetically modified (FVB Tg.AC Hemizygous) mice and carcinogenicity studies of acesulfame potassium in genetically modified [B6.129-Trp53(tm1Brd) (N5) Haploinsufficient] mice (feed studies)mice.
2005 Oct
Enhancement of rat bladder contraction by artificial sweeteners via increased extracellular Ca2+ influx.
2006 Dec 1
Development of a healthy biscuit: an alternative approach to biscuit manufacture.
2006 Mar 15
Linear response of mutans streptococci to increasing frequency of xylitol chewing gum use: a randomized controlled trial [ISRCTN43479664].
2006 Mar 24
Taste masking analysis in pharmaceutical formulation development using an electronic tongue.
2006 Mar 9
Direct simultaneous determination of eight sweeteners in foods by capillary isotachophoresis.
2006 May
Testing needed for acesulfame potassium, an artificial sweetener.
2006 Sep
The erosive potential of some flavoured waters.
2007 Jan
Sweet taste receptors in rat small intestine stimulate glucose absorption through apical GLUT2.
2007 Jul 1
The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor.
2007 Oct 12
Behavioral genetics and taste.
2007 Sep 18
Glucose sensing in L cells: a primary cell study.
2008 Dec
Detection of food additives by voltammetry at the liquid-liquid interface.
2008 Jun 25
Spanish Ketogenic Mediterranean Diet: a healthy cardiovascular diet for weight loss.
2008 Oct 26
Reducing added sugar intake in Norway by replacing sugar sweetened beverages with beverages containing intense sweeteners - a risk benefit assessment.
2008 Sep
Sensory properties and color measurements of dietary chocolates with different compositions during storage for up to 360 days.
2009
General and persistent effects of high-intensity sweeteners on body weight gain and caloric compensation in rats.
2009 Aug
[Simultaneous determination of artificial sweeteners in beverage by ultra performance liquid chromatography].
2009 Jan
Standards of medical care in diabetes--2009.
2009 Jan
Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT).
2009 Jul
Acute ingestion of a novel whey-derived peptide improves vascular endothelial responses in healthy individuals: a randomized, placebo controlled trial.
2009 Jul 22
Ubiquitous occurrence of the artificial sweetener acesulfame in the aquatic environment: an ideal chemical marker of domestic wastewater in groundwater.
2009 Jun 15
Incretin release from gut is acutely enhanced by sugar but not by sweeteners in vivo.
2009 Mar
In vivo cytogenetic studies on aspartame.
2010
[Determination of five synthetic sweeteners in wines using high performance liquid chromatography-tandem mass spectrometry].
2010 Aug
[Simultaneous determination of six food additives in meat products by high performance liquid chromatography].
2010 Dec
Impact of ionic liquids in environment and humans: an overview.
2010 Dec
Standards of medical care in diabetes--2010.
2010 Jan
Inadequate toxicity tests of food additive acesulfame.
2010 Jan-Mar
Gain weight by "going diet?" Artificial sweeteners and the neurobiology of sugar cravings: Neuroscience 2010.
2010 Jun
Performance of conventional multi-barrier drinking water treatment plants for the removal of four artificial sweeteners.
2010 Jun
An electronic tongue: evaluation of the masking efficacy of sweetening and/or flavoring agents on the bitter taste of epinephrine.
2010 Jun
Modulation of bitter taste perception by a small molecule hTAS2R antagonist.
2010 Jun 22
[Simultaneous determination of various aseptics and sweeteners in milk and dairy products].
2010 Mar
Pt(II) and Ag(I) complexes with acesulfame: crystal structure and a study of their antitumoral, antimicrobial and antiviral activities.
2010 May
Polymorphism in acesulfame sweetener: structure-property and stability relationships of bending and brittle crystals.
2010 May 28
Rational development of taste masked oral liquids guided by an electronic tongue.
2010 Nov 15
Patents

Patents

Sample Use Guides

Acceptable daily intake: 9mg per kg of body weight
Route of Administration: Oral
Acesulfame`s effect on the contractile response of isolated rat detrusor muscle strips was evaluated. The atropine-resistant response to EFS was marginally increased by acesulfame K 10(-6) M. Acesulfame K 10(-6) M increased the maximum contractile response to alpha,beta methylene ATP by 35% (+/-9.6%) (p<0.05) and to KCl by 12% (+/-3.1%) (p<0.01). Acesulfame K 10(-6) M increased the log EC(50) from -2.79 (+/-0.037) to -3.03 (+/-0.048, p<0.01).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:12:20 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:20 GMT 2023
Record UNII
MA3UYZ6K1H
Record Status Validated (UNII)
Record Version
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Name Type Language
ACESULFAME
HSDB   II   INN   MI   WHO-DD  
INN  
Official Name English
ACESULFAME [II]
Common Name English
ACESULFAME [HSDB]
Common Name English
ACESULFAME [MI]
Common Name English
acesulfame [INN]
Common Name English
Acesulfame [WHO-DD]
Common Name English
6-METHYL-1,2,3-OXATHIAZIN-4(3H)-ONE 2,2-DIOXIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C283
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
Code System Code Type Description
EVMPD
SUB05216MIG
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
HSDB
3914
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
PUBCHEM
36573
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
251-622-6
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID0048006
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
RXCUI
1310546
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL176687
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
LACTMED
Acesulfame
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
DAILYMED
MA3UYZ6K1H
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
CAS
33665-90-6
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
FDA UNII
MA3UYZ6K1H
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
CHEBI
83501
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
INN
3768
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
NCI_THESAURUS
C76511
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
MERCK INDEX
m1308
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY Merck Index
SMS_ID
100000087935
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY