FComEx: Aspartame (PC000526)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:09 UTC

Update date

2017-01-19 02:36:27 UTC

FoodComEx ID

PC000526

FoodDB Record

FDB000569

Chemical Information

Name

Aspartame

Description

Compd. 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 Number

22839-47-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1-Methyl N-L-a-aspartyl-L-phenylalanate	Generator
1-Methyl N-L-a-aspartyl-L-phenylalanic acid	Generator
1-Methyl N-L-alpha-aspartyl-L-phenylalanate	biospider
1-Methyl N-L-alpha-aspartyl-L-phenylalanic acid	Generator
1-Methyl N-L-alpha-aspartyl-L-phenylalanine	biospider
1-Methyl N-L-α-aspartyl-L-phenylalanate	Generator
1-Methyl N-L-α-aspartyl-L-phenylalanic acid	Generator
3-amino-N-(a-Carboxyphenethyl)succinamate N-methyl ester	Generator
3-amino-N-(a-Carboxyphenethyl)succinamic acid N-methyl ester	Generator
3-amino-N-(a-Methoxycarbonylphenethyl) succinamate	Generator
3-amino-N-(a-Methoxycarbonylphenethyl) succinamic acid	Generator
3-amino-N-(alpha-Carboxyphenethyl)succinamate N-methyl ester	Generator
3-amino-N-(alpha-Carboxyphenethyl)succinamic acid N-methyl ester	ChEBI
3-amino-N-(alpha-Methoxycarbonylphenethyl) succinamate	Generator
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acid	biospider
3-amino-N-(α-carboxyphenethyl)succinamate N-methyl ester	Generator
3-amino-N-(α-carboxyphenethyl)succinamic acid N-methyl ester	Generator
3-amino-N-(α-methoxycarbonylphenethyl) succinamate	Generator
3-amino-N-(α-methoxycarbonylphenethyl) succinamic acid	Generator
a-APM	db_source
APM	biospider
Asp-phe-ome	biospider
Aspartam	biospider
Aspartame (NF/inn)	biospider
Aspartame [usan:ban:inn]	biospider
Aspartame, l,l-alpha-	biospider
Aspartamo	biospider
Aspartamum	biospider
Aspartylphenylalanine methyl ester	biospider
Canderel	db_source
Dipeptide sweetener	biospider
e 951	HMDB
E951	db_source
Equal	biospider
L-Aspartyl-L-3-phenylalanine methyl ester	biospider
L-aspartyl-l-phenylalanine methyl ester	biospider
L-aspartyl-l-phenylalanyl methyl ester	biospider
L-Phenylalanine, L-alpha-aspartyl-, 2-methyl ester	biospider
L-Phenylalanine, N-L-alpha-aspartyl-, 1-methyl ester	biospider
Methyl aspartylphenylalanate	biospider
Methyl aspartylphenylalanine	db_source
Methyl l-alpha-aspartyl-l-phenylalanate	biospider
Methyl l-aspartyl-l-phenylalanine	biospider
Methyl n-l-alpha-aspartyl-l-phenylalaninate	biospider
N-a-Aspartyl-L-phenylalanine 1-methyl ester, 9CI	db_source
N-L-alpha-Aspartyl-L-phenylalanine 1-methyl ester	biospider
Nutrasweet	db_source
Pal sweet	biospider
Palsweet diet	biospider
SC-18862	db_source
Sweet dipeptide	biospider
Tri-sweet	biospider

Chemical Formula

C14H18N2O5

IUPAC name

3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)-C-hydroxycarbonimidoyl]propanoic acid

InChI Identifier

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)

InChI Key

IAOZJIPTCAWIRG-UHFFFAOYSA-N

Isomeric SMILES

COC(=O)C(CC1=CC=CC=C1)N=C(O)C(N)CC(O)=O

Average Molecular Weight

294.3031

Monoisotopic Molecular Weight

294.121571696

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents