Record Information
Creation date2010-04-08 22:04:37 UTC
Update date2018-05-28 23:02:10 UTC
Primary IDFDB000569
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAspartame
DescriptionCompd. with 100 times the sweetness of sucrose. Artificial sweetener permitted in foods in EU at 300-5500 ppmand is also permitted in USA. Widely used in foods, beverages and pharmaceutical formulations Aspartame (L-alpha-aspartyl-L-phenylalanine methyl ester) is a low-calorie sweetener used to sweeten a wide variety of low- and reduced-calorie foods and beverages, including low-calorie tabletop sweeteners. Aspartame is composed of two amino acids, aspartic acid and phenylalanine, as the methyl ester. Aspartic acid and phenylalanine are also found naturally in protein containing foods, including meats, grains and dairy products. Methyl esters are also found naturally in many foods such as fruits and vegetable and their juices. Upon digestion, aspartame breaks down into three components (aspartic acid, phenylalanine and methanol), which are then absorbed into the blood and used in normal body processes. Neither aspartame nor its components accumulates in the body. These components are used in the body in the same ways as when they are derived from common foods.; Aspartame is an artificial sweetener. It is 200 times sweeter than sugar in typical concentrations, without the high energy value of sugar. While aspartame, like other peptides, has a caloric value of 4 kilocalories (17 kilojoules) per gram, the quantity of aspartame needed to produce a sweet taste is so small that its caloric contribution is negligible, which makes it a popular sweetener for those trying to avoid calories from sugar. The taste of aspartame is not identical to that of sugar: the sweetness of aspartame has a slower onset and longer duration than that of sugar. Blends of aspartame with acesulfame potassium?usually listed in ingredients as acesulfame K?are alleged[who?] to taste more like sugar, and to be sweeter than either substitute used alone.; Aspartame is the name for an artificial, non-carbohydrate sweetener, aspartyl-phenylalanine-1-methyl ester; This sweetener is marketed under a number of trademark names, including Equal, NutraSweet, and Canderel, and is an ingredient of approximately 6,000 consumer foods and beverages sold worldwide, including (but not limited to) diet sodas and other soft drinks, instant breakfasts, breath mints, cereals, sugar-free chewing gum, cocoa mixes, frozen desserts, gelatin desserts, juices, laxatives, chewable vitamins supplements, milk drinks, pharmaceutical drugs and supplements, shake mixes, tabletop sweeteners, teas, instant coffees, topping mixes, wine coolers and yogurt. It is provided as a table condiment in some countries. However, aspartame is not always suitable for baking because it often breaks down when heated and loses much of its sweetness. Aspartame is also one of the main sugar substitutes used by people with diabetes.; i.e., the methyl ester of the dipeptide of the amino acids aspartic acid and phenylalanine. It is marketed under a number of trademark names, such as Equal, and Canderel, and is an ingredient of approximately 6,000 consumer foods and beverages sold worldwide. It is commonly used in diet soft drinks, and is often provided as a table condiment. It is also used in some brands of chewable vitamin supplements. In the European Union, it is also known under the E number (additive code) E951. Aspartame is also one of the sugar substitutes used by diabetics. Upon ingestion, aspartame breaks down into several constituent chemicals, including the naturally-occurring essential amino acid phenylalanine which is a health hazard to the few people born with phenylketonuria, a congenital inability to process phenylalanine. Aspartic acid is an amino acid commonly found in foods. Approximately 40% of aspartame (by mass) is broken down into aspartic acid. Because aspartame is metabolized and absorbed very quickly (unlike aspartic acid-containing proteins in foods), it is known that aspartame could spike blood plasma levels of aspartate. Aspartic acid is in a class of chemicals known as excitotoxins. Abnormally high levels of excitotoxins have been shown in hundreds of animals studies to cause damage to areas of the brain unprotected by the blood-brain barrier and a variety of chronic diseases arising out of this neurotoxicity.
CAS Number22839-47-0
Gold, hermesetasMeSH
Hermesetas goldMeSH
Aspartylphenylalanine, methylMeSH
Aspartylphenylalanine methyl esterMeSH
Methyl ester, aspartylphenylalanineMeSH
Tri sweetMeSH
Methyl aspartylphenylalanineMeSH
1-Methyl N-L-a-aspartyl-L-phenylalanateGenerator
1-Methyl N-L-a-aspartyl-L-phenylalanic acidGenerator
1-Methyl N-L-alpha-aspartyl-L-phenylalanatebiospider
1-Methyl N-L-alpha-aspartyl-L-phenylalanic acidGenerator
1-Methyl N-L-alpha-aspartyl-L-phenylalaninebiospider
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-(a-Methoxycarbonylphenethyl) succinamateGenerator
3-amino-N-(a-Methoxycarbonylphenethyl) succinamic acidGenerator
3-amino-N-(alpha-Carboxyphenethyl)succinamate N-methyl esterGenerator
3-amino-N-(alpha-Carboxyphenethyl)succinamic acid N-methyl esterChEBI
3-amino-N-(alpha-Methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acidbiospider
3-amino-N-(α-carboxyphenethyl)succinamate N-methyl esterGenerator
3-amino-N-(α-carboxyphenethyl)succinamic acid N-methyl esterGenerator
3-amino-N-(α-methoxycarbonylphenethyl) succinamateGenerator
3-amino-N-(α-methoxycarbonylphenethyl) succinamic acidGenerator
Aspartame (NF/inn)biospider
Aspartame [usan:ban:inn]biospider
Aspartame, l,l-alpha-biospider
Dipeptide sweetenerbiospider
e 951HMDB
L-Aspartyl-L-3-phenylalanine methyl esterbiospider
L-aspartyl-l-phenylalanine methyl esterbiospider
L-aspartyl-l-phenylalanyl methyl esterbiospider
L-Phenylalanine, L-alpha-aspartyl-, 2-methyl esterbiospider
L-Phenylalanine, N-L-alpha-aspartyl-, 1-methyl esterbiospider
Methyl aspartylphenylalanatebiospider
Methyl l-alpha-aspartyl-l-phenylalanatebiospider
Methyl l-aspartyl-l-phenylalaninebiospider
Methyl n-l-alpha-aspartyl-l-phenylalaninatebiospider
N-a-Aspartyl-L-phenylalanine 1-methyl ester, 9CIdb_source
N-L-alpha-Aspartyl-L-phenylalanine 1-methyl esterbiospider
Pal sweetbiospider
Palsweet dietbiospider
Sweet dipeptidebiospider
Predicted Properties
Water Solubility0.44 g/LALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.74 m³·mol⁻¹ChemAxon
Polarizability29.37 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H18N2O5
IUPAC name3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)-C-hydroxycarbonimidoyl]propanoic acid
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)
Average Molecular Weight294.3031
Monoisotopic Molecular Weight294.121571696
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
  • Alpha peptide
  • Phenylalanine or derivatives
  • Aspartic acid or derivatives
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Methyl ester
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Carboxylic acid
  • Organic oxygen compound
  • Primary amine
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 6.16%; N 9.52%; O 27.18%DFC
Melting PointMp 245-247° (double Mp) (235-236° dec.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D +32 (c, 1 in AcOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
TypeDescriptionSplash KeyView
Predicted GC-MSAspartame, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-9110000000-f5ee3d317c353c8c070bSpectrum
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-4290000000-78eca8194ea207885c3e2018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-9830000000-2ebffc8dbd4b056136b52018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-06e0d62d78c51ebb70212018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-2dd74f3b3a55388361ad2018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02dm-1490000000-2d21c56fc433f05d69492018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01si-9810000000-336adb09a6b6f7adf8fc2018-04-06View Spectrum
NMRNot Available
ChemSpider ID118630
KEGG Compound IDC11045
Pubchem Compound ID134601
Pubchem Substance IDNot Available
ChEBI ID2877
Phenol-Explorer IDNot Available
DrugBank IDDB00168
CRC / DFC (Dictionary of Food Compounds) IDBDS15-X:BDS15-X
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAspartame
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference