Record Information
Version1.0
Creation date2018-05-02 12:04:28 UTC
Update date2018-05-04 14:25:33 UTC
FoodComEx IDPC001176
FoodDB RecordFDB000569
Chemical Information
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-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
a-APMdb_source
APMbiospider
Asp-phe-omebiospider
Aspartambiospider
Aspartame (NF/inn)biospider
Aspartame [usan:ban:inn]biospider
Aspartame, l,l-alpha-biospider
Aspartamobiospider
Aspartamumbiospider
Aspartylphenylalanine methyl esterbiospider
Candereldb_source
Dipeptide sweetenerbiospider
e 951HMDB
E951db_source
Equalbiospider
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 aspartylphenylalaninedb_source
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
Pal sweetbiospider
Palsweet dietbiospider
SC-18862db_source
Sweet dipeptidebiospider
Tri-sweetbiospider
Chemical FormulaC14H18N2O5
IUPAC name(3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 245-247° (double Mp) (235-236° dec.)DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage Conditions-18°C
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
AKSci E436
AKSci J10514
AKSci HMDB0001894
Glentham GE0967
MetaSci HMDB0001894
Toronto Research Chemicals A790015