U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ASPARTAME

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q8TE23
Gene ID: 80834.0
Gene Symbol: TAS1R2
Target Organism: Homo sapiens (Human)
Target ID: Q7RTX0
Gene ID: 83756.0
Gene Symbol: TAS1R3
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Canderel

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Why do some dietary migraine patients claim they get headaches from placebos?
2000 May
Structure, dynamics, and stability of beta-cyclodextrin inclusion complexes of aspartame and neotame.
2001 Apr
Effects of dietary arabinogalactan on gastrointestinal and blood parameters in healthy human subjects.
2001 Aug
[NutraSweet--aspartame].
2001 Feb 19
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
Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study.
2001 May
[Artificial sweeteners--are they potentially carcinogenic?].
2001 Nov 15
Migraine MLT-down: an unusual presentation of migraine in patients with aspartame-triggered headaches.
2001 Oct
Whole nerve chorda tympani responses to sweeteners in C57BL/6ByJ and 129P3/J mice.
2001 Sep
Aspartame: review of safety.
2002 Apr
Boilysin and thermolysin in dipeptide synthesis: a comparative study.
2002 Aug
The effect of retrograde and anterograde glucose administration on memory performance in healthy young adults.
2002 Aug 21
Hepatitis B and C virus prevalence in a rural area of South Korea: the role of acupuncture.
2002 Jul 29
In vivo dental plaque pH variation with regular and diet soft drinks.
2002 Jul-Aug
Effects of L-tyrosine and carbohydrate ingestion on endurance exercise performance.
2002 Nov
Japan's innovators take patent deals to court.
2002 Oct 17
[Controversies with aspartame].
2003
An intermediate in a new synthesis approach to beta-substituted beta-hydroxyaspartame.
2003 Aug
Estimated intake of the artificial sweeteners acesulfame-K, aspartame, cyclamate and saccharin in a group of Swedish diabetics.
2003 Feb
Discovery and structure determination of a novel Maillard-derived sweetness enhancer by application of the comparative taste dilution analysis (cTDA).
2003 Feb 12
Formaldehyde-induced shrinkage of rat thymocytes.
2003 Jan
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
Aspartame disease: a possible cause for concomitant Graves' disease and pulmonary hypertension.
2004
Genotoxicity of aspartame.
2004 Aug
The influence of fat co-administration on the glucose memory facilitation effect.
2004 Feb
Evaluation of a possible proximity effect of aspartame and vitamin C on muscular strength.
2004 Feb
Influence of repeated consumption of beverages containing sucrose or intense sweeteners on food intake.
2004 Jan
Aspartame has no effect on the polymerization of sickle hemoglobin.
2004 Mar
Effect of concentration on taste-taste interactions in foods for elderly and young subjects.
2004 Oct
Aspartame and its effects on health.
2004 Oct 2
Influence of strawberry yogurt composition on aroma release.
2004 Oct 6
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 Sat Dec 16 16:56:28 GMT 2023
Edited
by admin
on Sat Dec 16 16:56:28 GMT 2023
Record UNII
Z0H242BBR1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASPARTAME
EP   FCC   FHFI   HSDB   II   INCI   INN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
METHYL ASPARTYLPHENYLALANATE
Common Name English
ASPARTAME [HSDB]
Common Name English
APM
Code English
L-ASPARTYL-L-PHENYLALANYL METHYL ESTER
Common Name English
E-951
Code English
L-PHENYLALANINE, N-L-.ALPHA.-ASPARTYL-, 1-METHYL ESTER
Common Name English
ASPARTAME [USP-RS]
Common Name English
ASPARTAME [EP MONOGRAPH]
Common Name English
SLADEX
Brand Name English
EQUAL
Brand Name English
ASPARTAME [USAN]
Common Name English
3-Amino-N-(α-carboxyphenethyl)succinamic acid N-methyl ester
Systematic Name English
ASPARTAME [II]
Common Name English
NUTRASWEET
Brand Name English
Aspartame [WHO-DD]
Common Name English
aspartame [INN]
Common Name English
PAL SWEET
Brand Name English
NSC-758953
Code English
ASPARTAME [INCI]
Common Name English
ASPARTAME (E951)
Common Name English
INS NO.951
Common Name English
ASPARTAME [FHFI]
Common Name English
SC-18862
Code English
ASPARTAME [FCC]
Common Name English
INS-951
Common Name English
ZERO-CAL
Brand Name English
ASPARTAME [MI]
Common Name English
ASPARTAME [VANDF]
Common Name English
ASPARTAME [MART.]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 201.66
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
NCI_THESAURUS C283
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
CODEX ALIMENTARIUS (GSFA) INS-951
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
CFR 21 CFR 172.804
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
CFR 21 CFR 201.21
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
DSLD 1055 (Number of products:1)
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
JECFA EVALUATION INS-951
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1043706
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
EU FOOD ADDITIVES
E-951
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
PUBCHEM
134601
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
NSC
758953
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
CAS
22839-47-0
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
LACTMED
Aspartame
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
DRUG BANK
DB00168
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PRIMARY
INN
3019
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-261-3
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL171679
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
MERCK INDEX
m2099
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY Merck Index
DAILYMED
Z0H242BBR1
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID0020107
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
MESH
D001218
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
NCI_THESAURUS
C76513
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
SMS_ID
100000139218
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
FDA UNII
Z0H242BBR1
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
CHEBI
2877
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
RXCUI
1311524
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY RxNorm
EVMPD
SUB84574
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
HSDB
3915
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
WIKIPEDIA
ASPARTAME
Created by admin on Sat Dec 16 16:56:29 GMT 2023 , Edited by admin on Sat Dec 16 16:56:29 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
Related Record Type Details
ACTIVE MOIETY