Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H18N2O5 |
Molecular Weight | 294.3031 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O
InChI
InChIKey=IAOZJIPTCAWIRG-QWRGUYRKSA-N
InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1
Molecular Formula | C14H18N2O5 |
Molecular Weight | 294.3031 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Aspartame (l-aspartyl-l-phenylalanine methyl ester) known to the public as NutraSweet has been the subject of controversy since it first became an ingredient in food products. The perceived sweetness of aspartame in humans is due to its binding of the heterodimer G-protein coupled receptor formed by the proteins TAS1R2 and TAS1R3. Aspartame was used in experiments on animals to study its role in delays of osteoarthritis. It was shown, that aspartame improved bone cortical density and muscle mass, and might contribute to a better quality of life for these diseased animals. In addition, was investigated the effect in patients with sickle cell anemia. It was revealed, that oral administration of aspartame lead inhibition of sickle cells. That effect was explained by binding aspartame with two human Bence Jones proteins: Mcg and Sea. Thus was suggested, that aspartame could interfere with sickle hemoglobin fibril formation. Then several studies showed that aspartame had no effect on the polymerization of sickle hemoglobin.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q8TE23 Gene ID: 80834.0 Gene Symbol: TAS1R2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11917125 |
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Target ID: Q7RTX0 Gene ID: 83756.0 Gene Symbol: TAS1R3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11917125 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Canderel Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Why do some dietary migraine patients claim they get headaches from placebos? | 2000 May |
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Structure, dynamics, and stability of beta-cyclodextrin inclusion complexes of aspartame and neotame. | 2001 Apr |
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Effects of dietary arabinogalactan on gastrointestinal and blood parameters in healthy human subjects. | 2001 Aug |
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[NutraSweet--aspartame]. | 2001 Feb 19 |
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Calculation of the intake of three intense sweeteners in young insulin-dependent diabetics. | 2001 Jul |
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[Simultaneous determination of various food additives by high performance liquid chromatography]. | 2001 Mar |
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Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study. | 2001 May |
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[Artificial sweeteners--are they potentially carcinogenic?]. | 2001 Nov 15 |
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Migraine MLT-down: an unusual presentation of migraine in patients with aspartame-triggered headaches. | 2001 Oct |
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Whole nerve chorda tympani responses to sweeteners in C57BL/6ByJ and 129P3/J mice. | 2001 Sep |
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Aspartame: review of safety. | 2002 Apr |
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Boilysin and thermolysin in dipeptide synthesis: a comparative study. | 2002 Aug |
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The effect of retrograde and anterograde glucose administration on memory performance in healthy young adults. | 2002 Aug 21 |
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Hepatitis B and C virus prevalence in a rural area of South Korea: the role of acupuncture. | 2002 Jul 29 |
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In vivo dental plaque pH variation with regular and diet soft drinks. | 2002 Jul-Aug |
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Effects of L-tyrosine and carbohydrate ingestion on endurance exercise performance. | 2002 Nov |
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Japan's innovators take patent deals to court. | 2002 Oct 17 |
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[Controversies with aspartame]. | 2003 |
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An intermediate in a new synthesis approach to beta-substituted beta-hydroxyaspartame. | 2003 Aug |
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Estimated intake of the artificial sweeteners acesulfame-K, aspartame, cyclamate and saccharin in a group of Swedish diabetics. | 2003 Feb |
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Discovery and structure determination of a novel Maillard-derived sweetness enhancer by application of the comparative taste dilution analysis (cTDA). | 2003 Feb 12 |
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Formaldehyde-induced shrinkage of rat thymocytes. | 2003 Jan |
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Comparison of the responses of the chorda tympani and glossopharyngeal nerves to taste stimuli in C57BL/6J mice. | 2003 Mar 4 |
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The powder flow and compact mechanical properties of sucrose and three high-intensity sweeteners used in chewable tablets. | 2003 May 12 |
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Aspartame disease: a possible cause for concomitant Graves' disease and pulmonary hypertension. | 2004 |
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Genotoxicity of aspartame. | 2004 Aug |
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The influence of fat co-administration on the glucose memory facilitation effect. | 2004 Feb |
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Evaluation of a possible proximity effect of aspartame and vitamin C on muscular strength. | 2004 Feb |
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Influence of repeated consumption of beverages containing sucrose or intense sweeteners on food intake. | 2004 Jan |
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Aspartame has no effect on the polymerization of sickle hemoglobin. | 2004 Mar |
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Effect of concentration on taste-taste interactions in foods for elderly and young subjects. | 2004 Oct |
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Aspartame and its effects on health. | 2004 Oct 2 |
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Influence of strawberry yogurt composition on aroma release. | 2004 Oct 6 |
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Different functional roles of T1R subunits in the heteromeric taste receptors. | 2004 Sep 28 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11372003
23 subjects from the Sickle Cell Clinic (University of Oklahoma Health Sciences Center, Oklahoma City, Okla) consented to participate in a randomized single-dose administration of 1.5, 3.0, or 6 mg/kg aspartame.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11372003
For the in vitro studies, blood from 20 subjects monitored for sickle cell anemia was collected in heparinized tubes. Specimens were divided in thirds and aspartame was added to 2 tubes to yield a 1 mg/mL or 2 mg/mL concentration. Sickled cells that were present after a drop from each aliquot was added to a fresh 2% metabisulfite solution were counted 3 times. For the in vitro studies, sickled cells decreased from 28% to < 14% when 1 mg/mL aspartame was added and decreased further with 2 mg/mL.
Substance Class |
Chemical
Created
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Record UNII |
Z0H242BBR1
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 201.66
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NCI_THESAURUS |
C283
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CODEX ALIMENTARIUS (GSFA) |
INS-951
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CFR |
21 CFR 172.804
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CFR |
21 CFR 201.21
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DSLD |
1055 (Number of products:1)
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JECFA EVALUATION |
INS-951
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1043706
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E-951
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758953
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22839-47-0
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Aspartame
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DB00168
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CHEMBL171679
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m2099
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Z0H242BBR1
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D001218
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C76513
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100000139218
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Z0H242BBR1
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1311524
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SUB84574
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3915
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ASPARTAME
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
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Related Record | Type | Details | ||
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ACTIVE MOIETY |