(3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid

• ChemBase ID: 70035
• Molecular Formular: C14H18N2O5
• Molecular Mass: 294.30312
• Monoisotopic Mass: 294.12157169
• SMILES: C(=O)([C@@H](N)CC(=O)O)N[C@H](C(=O)OC)Cc1ccccc1
• Canonical SMILES: COC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)Cc1ccccc1
• InChI: 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)/t10-,11-/m0/s1
• InChIKey: IAOZJIPTCAWIRG-QWRGUYRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: aspartame
• Synonyms: Asp-Phe methyl ester; Nutrasweet; Aspartame; Canderel; Dipeptide Sweetener; E 951; Equal; Finn; L-Aspartame; Pal Sweet; Palsweet Diet; Sweet Dipeptide; Zero-Cal; α-Aspartame; α-L-Aspartyl-L-phenylalanine Methyl Ester; α-Sweet; L-α-Aspartyl-L-phenylalanine 2-Methyl Ester; (S)-3-amino-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic acid; Aspartame; L-ASPARTYL-L-PHENYLALANINE METHYL ESTER; Asp-Phe methyl ester; Aspartame; N-(L-α-Aspartyl)-L-phenylalanine methyl ester; Asp-Phe-OMe; Asp-Phe methyl ester; N-(L-α-天冬氨酰)-L-苯丙氨酸甲酯; 天冬甜素; 阿斯巴甜; 天冬酰-苯丙氨酸甲酯; 天冬酰-苯丙氨酸甲酯; 天冬甜素

Database IDs

• CAS Number: 22839-47-0
• EC Number: 245-261-3
• MDL Number: MFCD00002724
• Beilstein Number: 2223850
• PubChem SID: 162035760; 24870725; 24890947
• PubChem CID: 134601
• CHEBI ID: 2877
• CHEMBL: 171679
• Chemspider ID: 118630
• DrugBank ID: DB00168
• KEGG ID: C11045
• Unique Ingredient Identifier: Z0H242BBR1
• Wikipedia Title: Aspartame
• E Number: E951

CALCULATED PROPERTIES

• Acid pKa: 3.525723
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.2199712
• LogD (pH = 7.4): -2.2454615
• Log P: -2.2182105
• Molar Refractivity: 73.2182 cm^3
• Polarizability: 29.14675 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; slightly soluble in ethanol; sparingly soluble in water
• Apperance: White Solid
• Melting Point: 237-238°C; 242-248 °C; 246–247 °C; 247-249°C
• Boiling Point: decomposes
• Density: 1.347 g/cm^3
• pKa: 4.5–6.0
• Sweetness: 160-200 × sucrose

Safety Information

• Storage Condition: -20°C; 2-8°C; Refrigerator
• Storage Warning: IRRITANT
• RTECS: WM3407000
• German water hazard class: 2
• TSCA Listed: false
• NFPA704:
  

  1

  1

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• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥99.0% (HPLC); 95+%
• Grade: analytical standard
• Salt Data: Free Base
• Packaging: pkg of 500 mg
• Impurities: ≤4.5% water
• Linear Formula: HOOCCH2CH(NH2)CONHCH(CH2C6H5)COOCH3
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02190007

Crystalline
Potent synthetic sweetener

Selleck Chemicals - S2036

Research Area: Cancer
Biological Activity:

Sigma Aldrich - A5139

Biochem/physiol Actions
First generation synthetic sugar alternative that has been studied for its carcinogenic potential.
包装
1, 5, 25 g in poly bottle

Sigma Aldrich - 47135

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 47135.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A790015

A dipeptide ester about 160 times sweeter than sucrose in aqueous solution. A non-nutritive sweetener.

REFERENCES

• Cloninger, B., et al.: Science, 170, 81 (1970)
• Oppermann, et al.: J. Nutr., 103, 1454 (1970)