CasNo: 22839-47-0
Molecular Formula: C14H18N2O5
Appearance: White powder or tablets
Discovery |
Aspartame was discovered accidentally in 1965 by James M. Schlatter, an organic chemist working for G. D. Searle & Company, during a search for drugs to treat gastric ulcers. |
Composition and Metabolism |
Aspartame is metabolized in the gut to phenylalanine, aspartic acid, and methanol. |
Use limits |
Rapid metabolism in the body; does not accumulate. |
chemical property |
White crystalline powder with an intense sweet taste. |
Description |
Aspartame is a dipeptide ester consisting of phenylalanine and aspartic acid. Its chemical name is aspartyl-phenylalanine methyl ester. |
Category |
Toxic substances |
Explosive hazard characteristics |
Edible contact dermatitis. |
Combustible hazard characteristics |
Combustible; combustion produces toxic nitrogen oxide smoke |
Storage and transportation characteristics |
Combustible; combustion produces toxic nitrogen oxide smoke |
Fire extinguishing agent |
Dry powder, foam, sand, carbon dioxide, mist water |
Uses |
Aspartame is a synthetic non-caloric sweetener widely used in the food and beverage industry. |
Characteristics |
Aspartame has no odor but has an intense sweet taste. |
Originator |
Canderel,Searle,France,1979 |
Definition |
ChEBI: A dipeptide composed of methyl L-phenylalaninate and L-aspartic acid joined by a peptide linkage. |
Preparation |
By coupling the amino acids L-phenylalanine and L-aspartic acid, and the esterification of the carboxyl group of the phenylalanine moiety to produce the methyl ester. This esterification can occur before or after coupling. The crystallized slurry is centrifuged and the resulting “wet-cake” is washed to remove impurities. |
Production Methods |
Aspartame is synthesized using the L enantiomer of phenylalanine. The L enantiomer is separated from the D enantiomer, the racemic mixture, by reacting it with acetic anhydride (CH32 |
Therapeutic Function |
Sugar supplement |
Metabolism in the Body |
In the body, aspartame metabolizes into phenylalanine, methanol, and aspartic acid. |
Biochem/physiol Actions |
Asp-Phe methyl ester (Asp-Phe-OMe) is used as a synthetic sweeter, sugar substitute. Asp-Phe methyl ester is being studied for a variety of potential benefits as a nutrition supplement, such as the delay of osteoarthritis and modulation of rheumatoid factor activity. Asp-Phe methyl ester is being studied for its effect on thrombin activity and blood clotting. |
Safety Profile |
Human systemic effects byingestion: allergic dermatitis. Experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of NOx. |
Environmental Fate |
|
Metabolic pathway |
The rate of aspartame degradation is faster in a phosphate buffer solution than in a citrate buffer solution at the same pH and buffer concentration. The primary mechanism by which aspartame degrades, the formation of diketo piperazine, involves the nucleophilic attack of carbonyl by the free amine, which requires proton transfer. |
Incompatibilities |
Differential scanning calorimetry experiments with some directly compressible tablet excipients suggests that aspartame is incompatible with dibasic calcium phosphate and also with the lubricant magnesium stearate. Reactions between aspartame and sugar alcohols are also known. |
Regulatory Status |
Accepted for use as a food additive in Europe and in the USA. Included in the FDA Inactive Ingredients Database (oral powder for reconstitution, buccal patch, granules, syrups, and tablets). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients. |
Who Evaluation |
Evaluation year: 2016 |
InChI:InChI=1/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)/t10-,11-/m0/s1
The metabolism of aspartame has been studied in mice, rats, rabbits, dogs, monkeys, and humans. The compound was digested in all species in the same way as are natural constituents of the diet....
The use of the artificial sweetener, aspartame, has long been contemplated and studied by various researchers, and people are concerned about its negative effects. Aspartame is composed of phenylalanine (50%), aspartic acid (40%) and methanol (10%).
The protected aspartame, 4, has been pre...
mannitol
L-Asp-L-Phe-OMe
Conditions | Yield |
---|---|
|
anhydride du N-chloroacetyl-L-acide aspartique
methyl (2S)-2-amino-3-phenylpropanoate
L-Asp-L-Phe-OMe
α-L-aspartyl-L-phenylalanine methyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid; thiourea; sodium chloride; In methanol; 1,1-dichloroethane; water;
|
48% |
Boc-Asp(OtBu)-Phe-OMe
Z-Asp(OBzl)-Phe-OMe
methyl (2S)-2-amino-3-phenylpropanoate
<(4S)-2,2-bis(trifluoromethyl)-5-oxo-1,3-oxazolidine-4-yl>acetate
N,N-dimethyl-L-aspartyl-L-phenylalanine methyl ester
methanol
L-Aspartic acid
L-phenylalanine