Chemical Property of (3S)-3-azaniumyl-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoate
Chemical Property:
- Appearance/Colour:White powder or tablets
- Vapor Pressure:2.6E-12mmHg at 25°C
- Melting Point:242-248 °C
- Refractive Index:14.5 ° (C=4, 15mol/L Formic Acid)
- Boiling Point:535.8 °C at 760 mmHg
- PKA:pKa 3.19±0.01 (H2O t=25.0 I=0.100(NaCl))(Approximate);7.87±0.02(H2O t=25.0 I=0.100(NaCl))(Approximate)
- Flash Point:277.8 °C
- PSA：118.72000
- Density:1.28 g/cm3
- LogP:0.78010
- Storage Temp.:2-8°C
- Solubility.:Sparingly soluble or slightly soluble in water and in ethanol (96 per cent), practically insoluble in hexane and in methylene chloride.
- Water Solubility.:Soluble in formic acid, dimethyl sulfoxide. Sparingly soluble in water and ethanol.
- XLogP3:-2.1
- Hydrogen Bond Donor Count:2
- Hydrogen Bond Acceptor Count:5
- Rotatable Bond Count:7
- Exact Mass:294.12157168
- Heavy Atom Count:21
- Complexity:374
- Purity/Quality:
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99% *data from raw suppliers
Aspartame *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- Safety Statements:
22-24/25
- MSDS Files:
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SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Canonical SMILES:COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)[O-])[NH3+]
- Isomeric SMILES:COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)[O-])[NH3+]
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Composition and Usage
Aspartame is the methyl-ester of the aspartate-phenylalanine dipeptide and is widely used as a sweetener in both the food and pharmaceutical industries. It is found in over 5000 food products globally, including low-calorie beverages, dessert mixes, yogurt, multivitamins, morning cereals, and medicines.
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Discovery and Approval
Invented in 1965 by James M. Schlatter during research on antiulcer drugs, aspartame's sweetness was discovered accidentally. Approved by the U.S. FDA in 1981, it is about 200 times sweeter than sugar with almost zero calories.
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Acceptable Daily Intake and Labeling
The acceptable daily intake of aspartame is 40 mg/kg body weight in Europe and 50 mg/kg body weight in the United States. Products containing aspartame must be labeled to inform consumers, especially those with phenylketonuria, as it contains phenylalanine.
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Metabolism and Risks
Aspartame is hydrolyzed and absorbed in the gastrointestinal tract, releasing methanol, aspartic acid, and phenylalanine. Prolonged consumption may pose risks, especially to phenylketonuria patients.
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Applications Beyond Sweetening
Aspartame has been used in encapsulation processes to improve properties like stability, taste, color, and texture, extending storage times. It finds applications in food, cosmetics, agrochemicals, and pharmaceuticals.
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Stability and Degradation
Aspartame is stable in solid form but degrades in solution, especially in high temperatures or pH values above 6. It also loses sweetness when reacting with certain flavorings, aldehydes, or ketones.
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Usage in Baking and Confectionery
Although decomposed by baking, aspartame salts, and metal complexes can protect it, allowing its use in pastries. Its high sweetness makes it common in confectionery products like chewing gums.
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Safety Assessment and Genotoxic Properties
Despite safety assessments by various regulatory bodies, few studies have tested aspartame's genotoxic properties in vivo and in vitro, and none were conducted according to GLP standards.
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General Description
Aspartame is a dipeptide sweetener synthesized using immobilized penicillinacylase, which selectively cleaves the N-phenacetyl protecting group from N-phenacetyl aspartame to yield aspartame and phenylacetic acid. This enzymatic method offers a more efficient and selective alternative to traditional synthesis routes by enabling the removal of the nitrogen protecting group under mild conditions (pH 7.5), with the reaction rate influenced by the substituents at the α-carboxyl group of aspartic acid and its absolute configuration.
