Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H18N2O5.ClH |
| Molecular Weight | 330.764 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O
InChI
InChIKey=AAQFSZFQCXLMNT-ACMTZBLWSA-N
InChI=1S/C14H18N2O5.ClH/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);1H/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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
Target ID: Q8TE23 Gene ID: 80834.0 Gene Symbol: TAS1R2 Target Organism: Homo sapiens (Human) |
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Target ID: Q7RTX0 Gene ID: 83756.0 Gene Symbol: TAS1R3 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Canderel Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| One on one. Is aspartame safe to use? | 2001 Jan |
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| [Simultaneous determination of various food additives by high performance liquid chromatography]. | 2001 Mar |
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| Modified DNA aptamers against sweet agent aspartame. | 2002 |
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| The effect of various substances on the suppression of the bitterness of quinine-human gustatory sensation, binding, and taste sensor studies. | 2002 Dec |
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| [Controversies with aspartame]. | 2003 |
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| Physiological mechanisms mediating aspartame-induced satiety. | 2003 Apr |
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| An intermediate in a new synthesis approach to beta-substituted beta-hydroxyaspartame. | 2003 Aug |
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| Wants to clear up Internet misinformation regarding aspartame. | 2003 Aug 1 |
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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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| The diet factor in pediatric and adolescent migraine. | 2003 Jan |
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| Possible pathomechanism of autoimmune hepatitis. | 2003 Jan-Feb |
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| [Development of an optimized formulation of damask marmalade with low energy level using Taguchi methodology]. | 2003 Jun |
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| Headspace solid-phase micro-extraction gas chromatography method for the determination of methanol in aspartame sweeteners. | 2003 Jun |
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| Taste perception with age: generic or specific losses in supra-threshold intensities of five taste qualities? | 2003 Jun |
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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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| Effects of sugar intake on body weight: a review. | 2003 May |
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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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| Electrochemical study of the complexes of aspartame with Cu(II), Ni(II) and Zn(II) ions in the aqueous medium. | 2003 May 23 |
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| Systemic contact dermatitis of the eyelids caused by formaldehyde derived from aspartame? | 2003 Nov |
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| Construction of hybrid peptide synthetases for the production of alpha-l-aspartyl-l-phenylalanine, a precursor for the high-intensity sweetener aspartame. | 2003 Nov |
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| Aspartame disease: a possible cause for concomitant Graves' disease and pulmonary hypertension. | 2004 |
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| The effects of nicotine and sucrose on spatial memory and attention. | 2004 Apr |
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| The brain-cancer puzzle. | 2004 Apr |
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| Dietary estimated intake of intense sweeteners by Italian teenagers. Present levels and projections derived from the INRAN-RM-2001 food survey. | 2004 Apr |
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| Receptors for bitter, sweet and umami taste couple to inhibitory G protein signaling pathways. | 2004 Apr 12 |
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| Genotoxicity of aspartame. | 2004 Aug |
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| Aspartame and aspartame derivatives effect human thrombin catalytic activity. | 2004 Dec 20 |
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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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| Position of the American Dietetic Association: use of nutritive and nonnutritive sweeteners. | 2004 Feb |
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| The combination effect of L-arginine and NaCl on bitterness suppression of amino acid solutions. | 2004 Feb |
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| Effect of four-day psyllium supplementation on bowel preparation for colonoscopy:A prospective double blind randomized trial [ISRCTN76623768]. | 2004 Feb 2 |
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| Behavioral study in the gray mouse lemur (Microcebus murinus) using compounds considered sweet by humans. | 2004 Jan |
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| Influence of repeated consumption of beverages containing sucrose or intense sweeteners on food intake. | 2004 Jan |
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| Intercalation of amino acids and peptides into Mg-Al layered double hydroxide by reconstruction method. | 2004 Jan 28 |
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| Oral zinc sulfate solutions inhibit sweet taste perception. | 2004 Jul |
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| Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester. | 2004 Jun |
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| Effects of short-chain fructo-oligosaccharides on glucose and lipid metabolism in mild hypercholesterolaemic individuals. | 2004 Jun |
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| Acetaminophen-containing chewable tablets with suppressed bitterness and improved oral feeling. | 2004 Jun 18 |
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| Aspartame has no effect on the polymerization of sickle hemoglobin. | 2004 Mar |
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| [Adverse effect of aspartame--does it exist?]. | 2004 Mar 18 |
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| Chronic aspartame affects T-maze performance, brain cholinergic receptors and Na+,K+-ATPase in rats. | 2004 May |
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| Flow-through spectrophotometric sensor for the determination of aspartame in low-calorie and dietary products. | 2004 Oct |
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| Effect of concentration on taste-taste interactions in foods for elderly and young subjects. | 2004 Oct |
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| Artificial sweeteners--do they bear a carcinogenic risk? | 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
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
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
by
admin
on
Edited
Fri Dec 15 18:34:38 GMT 2023
by
admin
on
Fri Dec 15 18:34:38 GMT 2023
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| Record UNII |
MH4IO18KU0
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| Record Status |
Validated (UNII)
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| Record Version |
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