Record Information
Version1.0
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
Structure
Thumb
Synonyms
SynonymSource
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
1-Methyl N-L-alpha-aspartyl-L-phenylalaninebiospider
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-(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
a-APMdb_source
APMbiospider
Aspartame (NF/inn)biospider
Aspartame [usan:ban:inn]biospider
Aspartame, l,l-alpha-biospider
E951db_source
Equalbiospider
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 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
Nutrasweetdb_source
SC-18862db_source
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP-2.1ALOGPS
logP-1.7ChemAxon
logS-2.8ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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)
InChI KeyIAOZJIPTCAWIRG-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)C(CC1=CC=CC=C1)N=C(O)C(N)CC(O)=O
Average Molecular Weight294.3031
Monoisotopic Molecular Weight294.121571696
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9220000000-2625126bd17025b83933View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5904000000-075be5fd36b94f425650View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ns-0690000000-e92f66ca1ae82b0ccd81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-8eec324eec1e64466b1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01b9-2900000000-e8415697953bc139924bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0080-0890000000-b2e2c2a89ceaf3d1f9dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-0930000000-d8dbb5a34c019dc70708View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0080-0890000000-b2e2c2a89ceaf3d1f9dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-4390000000-5ea0d55c8c75f40eefdeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0109-9730000000-badb4105789050b52346View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-22c71b3445a360c7886aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-c48af459412db76084ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02bg-1690000000-df82228a7343c200b8d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03gu-9700000000-db183663829759af70f9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID118630
ChEMBL IDCHEMBL171679
KEGG Compound IDC11045
Pubchem Compound ID134601
Pubchem Substance IDNot Available
ChEBI ID2877
Phenol-Explorer IDNot Available
DrugBank IDDB00168
HMDB IDHMDB01894
CRC / DFC (Dictionary of Food Compounds) IDBDS15-X:BDS15-X
EAFUS ID263
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPME
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference