ASPARTAME (CHEM004783)

Record Information
Version1.0
Creation Date2016-05-19 01:54:46 UTC
Update Date2026-08-19 06:28:24 UTC
Accession NumberCHEM004783
Identification
Common NameASPARTAME
ClassSmall Molecule
Description
Flavoring agent sweeter than sugar, metabolized as phenylalanine and aspartic acid.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • Suspected Compounds – Schymanski Project
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Methyl N-L-alpha-aspartyl-L-phenylalanateChEBI
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl esterChEBI
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acidChEBI
AminoSweetChEBI
Asp-phe-omeChEBI
AspartamChEBI
AspartamoChEBI
AspartamumChEBI
Aspartylphenylalanine methyl esterChEBI
e 951ChEBI
L-Aspartyl-L-phenylalanine methyl esterChEBI
NutraSweetChEBI
SanectaChEBI
1-Methyl N-L-a-aspartyl-L-phenylalanateGenerator
1-Methyl N-L-a-aspartyl-L-phenylalanic acidGenerator
1-Methyl N-L-alpha-aspartyl-L-phenylalanic acidGenerator
1-Methyl N-L-α-aspartyl-L-phenylalanateGenerator
1-Methyl N-L-α-aspartyl-L-phenylalanic acidGenerator
3-Amino-N-(a-carboxyphenethyl)succinamate N-methyl esterGenerator
3-Amino-N-(a-carboxyphenethyl)succinamic acid N-methyl esterGenerator
3-Amino-N-(alpha-carboxyphenethyl)succinamate N-methyl esterGenerator
3-Amino-N-(α-carboxyphenethyl)succinamate N-methyl esterGenerator
3-Amino-N-(α-carboxyphenethyl)succinamic acid N-methyl esterGenerator
3-Amino-N-(a-methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(a-methoxycarbonylphenethyl) succinamic acidGenerator
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(α-methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(α-methoxycarbonylphenethyl) succinamic acidGenerator
CanderelHMDB
Dipeptide sweetenerHMDB
L-Aspartyl-L-3-phenylalanine methyl esterHMDB
L-Aspartyl-L-phenylalanyl methyl esterHMDB
Methyl aspartylphenylalanateHMDB
Pal sweetHMDB
Palsweet dietHMDB
Sweet dipeptideHMDB
Methyl aspartylphenylalanineHMDB
Methyl ester, aspartylphenylalanineHMDB
Muro brand OF aspartameHMDB
Aspartame hermes brandHMDB
Aspartame prodes brandHMDB
Aspartylphenylalanine, methylHMDB
GoldswiteHMDB
Hermesetas goldHMDB
Aspartame fuca brandHMDB
Aspartame muro brandHMDB
Diététiques et santé brand OF aspartameHMDB
Fuca brand OF aspartameHMDB
Prodes brand OF aspartameHMDB
Tri sweetHMDB
Gold, hermesetasHMDB
Hermes brand OF aspartameHMDB
MilisucreHMDB
NozucarHMDB
Tri-sweetHMDB
TriSweetHMDB
Chemical FormulaC14H18N2O5
Average Molecular Mass294.303 g/mol
Monoisotopic Mass294.122 g/mol
CAS Registry Number22839-47-0
IUPAC Name(3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
Traditional Nameaspartame
SMILESCOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O
InChI IdentifierInChI=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
InChI KeyIAOZJIPTCAWIRG-QWRGUYRKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Phenylalanine or derivatives
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid ester
  • Organic 1,3-dipolar compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.65 g/LALOGPS
logP-1.2ALOGPS
logP-2.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)8.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.22 m³·mol⁻¹ChemAxon
Polarizability29.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
External Links
DrugBank IDDB00168
HMDB IDHMDB0001894
FooDB IDFDB000569
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-5583
METLIN ID6377
PDB IDNot Available
Wikipedia LinkAspartame
Chemspider ID118630
ChEBI ID2877
PubChem Compound ID134601
Kegg Compound IDC11045
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fuganti, Claudio; Grasselli, Piero; Malpezzi, Luciana; Casati, Paolo. Synthesis of aspartame via asymmetric hydrogenation of N-protected (Z)-N-a-L-aspartyl-D-phenylalanine methyl ester. Journal of Organic Chemistry (1986), 51(7), 1126-8.
2. Lam S, Azumaya H, Karmen A: High-performance liquid chromatography of amino acids in urine and cerebrospinal fluid. J Chromatogr. 1984 Oct 19;302:21-9.
3. Fernstrom JD: Dietary amino acids and brain function. J Am Diet Assoc. 1994 Jan;94(1):71-7.
4. Azcurra AI, Calamari SE, Yankilevich ER, Battellino LJ, Cattoni ST, Colantonio G: [Effects of local treatment with sodium fluoride mouthrinse on peroxidase and hypothiocyanite saliva levels in adolescent]/. Acta Physiol Pharmacol Ther Latinoam. 1997;47(4):211-20.
5. Busch U, Schmid J, Heinzel G, Schmaus H, Baierl J, Huber C, Roth W: Pharmacokinetics of meloxicam in animals and the relevance to humans. Drug Metab Dispos. 1998 Jun;26(6):576-84.
6. Bidiwala KS, Lorenz JM, Kleinman LI: Renal function correlates of postnatal diuresis in preterm infants. Pediatrics. 1988 Jul;82(1):50-8.
7. Burns TS, Stargel WW, Tschanz C, Kotsonis FN, Hurwitz A: Aspartame and sucrose produce a similar increase in the plasma phenylalanine to large neutral amino acid ratio in healthy subjects. Pharmacology. 1991;43(4):210-9.
8. Romano M, Casacci F, De Marchi F, Pacei T, Esteve A, Lomuscio G, Mennini T, Salmona M: Effects of aspartame and carbohydrate administration on human and rat plasma large neutral amino acid levels and rat brain amino acid and monoamine levels. J Nutr. 1989 Jan;119(1):75-81.
9. McMasters DR, Vedani A: Ochratoxin binding to phenylalanyl-tRNA synthetase: computational approach to the mechanism of ochratoxicosis and its antagonism. J Med Chem. 1999 Aug 12;42(16):3075-86.
10. Kochansky CJ, Rippley RK, Yan KX, Song H, Wallace MA, Dean D, Jones AN, Lasseter K, Schwartz J, Vincent SH, Franklin RB, Wagner J: Absorption, metabolism, and excretion of [14C]MK-0767 (2-methoxy-5-(2,4-dioxo-5-thiazolidinyl)-N-[[4-(trifluoromethyl)phenyl] methyl]benzamide) in humans. Drug Metab Dispos. 2006 Sep;34(9):1457-61. Epub 2006 Jun 13.
11. Koeppe RA, Shulkin BL, Rosenspire KC, Shaw LA, Betz AL, Mangner T, Price JC, Agranoff BW: Effect of aspartame-derived phenylalanine on neutral amino acid uptake in human brain: a positron emission tomography study. J Neurochem. 1991 May;56(5):1526-35.
12. Yang D, Beylot M, Agarwal KC, Soloviev MV, Brunengraber H: Assay of the human liver citric acid cycle probe phenylacetylglutamine and of phenylacetate in plasma by gas chromatography-mass spectrometry. Anal Biochem. 1993 Jul;212(1):277-82.
13. Maher TJ, Wurtman RJ: Possible neurologic effects of aspartame, a widely used food additive. Environ Health Perspect. 1987 Nov;75:53-7.
14. Wurtman RJ, Maher TJ: Effects of oral aspartame on plasma phenylalanine in humans and experimental rodents. Short note. J Neural Transm. 1987;70(1-2):169-73.
15. Lam S: Stereoselective analysis of D and L dansyl amino acids as the mixed chelate copper(II) complexes by HPLC. J Chromatogr Sci. 1984 Sep;22(9):416-23.
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