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Aspartame

Catalog No. DB00168 Name DrugBank
CAS Number 22839-47-0 Website http://www.ualberta.ca/
M. F. C14H18N2O5 Telephone (780) 492-3111
M. W. 294.30312 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 53

SYNONYMS

IUPAC name
3-amino-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid
IUPAC Traditional name
aspartame
Brand Name
Tri-sweet
Equal
Canderel
Nutrasweet
Aminosweet
Synonyms
Methyl N-L-alpha-aspartyl-L-phenylalaninate
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester
1-Methyl N-L-alpha-aspartyl-L-phenylalanine
Asp-phe-ome
Aspartame [USAN:BAN:INN]
Aspartamo [INN-Spanish]
Aspartamum [INN-Latin]
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acid
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester, stereoisomer
Methyl L-aspartyl-L-phenylalanine
L-Aspartyl-L-phenylalanine methyl ester
Aspartam [INN-French]
APM
Aspartylphenylalanine methyl ester
1-Methyl N-L-alpha-aspartyl-L-phenylalanate
N-L-alpha-Aspartyl-L-phenylalanine 1-methyl ester
Methyl L-alpha-aspartyl-L-phenylalanate
Methyl aspartylphenylalanate
Dipeptide sweetener
Sweet dipeptide

DATABASE IDS

CAS Number 22839-47-0

PROPERTIES

Hydrophobicity(logP) -0.1
Solubility The solubility of aspartame in water is dependent on pH and temperature, the maximum solubility is reached at pH 2.2 (20 mg/mL at 25oC) and the minimum solubility at pH 5.2 (pHi) is 13.5 mg/mL at 25oC.

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description Flavoring agent sweeter than sugar, metabolized as phenylalanine and aspartic acid. [PubChem]
Indication Used as a diet supplement and sugar substitute.
Pharmacology 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.
Toxicity Mild gastrointestinal side effects including diarrhea have been reported.
Affected Organisms
Humans and other mammals
Biotransformation Approximately 10% of aspartame (by weight) is broken down into methanol in the small intestine. Most of the methanol is absorbed and quickly converted into formaldehyde. Approximately 50% of aspartame (by weight) is broken down into phenylalanine. Approximately 40% of aspartame (by mass) is broken down into aspartic acid.
Absorption Absorbed in the small intestine, aspartame is metabolized and absorbed very quickly.
Half Life At room temperature, aspartame is most stable at pH 4.3, where its half-life is nearly 300 days. At pH 7 however, its half-life is only a few days.
External Links
Wikipedia

REFERENCES