(3S)-3-amino-3-{[(1R)-1-[(2,2,4,4-tetramethylthietan-3-yl)carbamoyl]ethyl]carbamoyl}propanoic acid

• ChemBase ID: 70630
• Molecular Formular: C14H25N3O4S
• Molecular Mass: 331.431
• Monoisotopic Mass: 331.1565773
• SMILES: C(=O)(C[C@@H](C(=O)N[C@@H](C(=O)NC1C(SC1(C)C)(C)C)C)N)O
• Canonical SMILES: OC(=O)C[C@@H](C(=O)N[C@@H](C(=O)NC1C(C)(C)SC1(C)C)C)N
• InChI: InChI=1S/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)/t7-,8+/m1/s1
• InChIKey: IVBOUFAWPCPFTQ-SFYZADRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-3-{[(1R)-1-[(2,2,4,4-tetramethylthietan-3-yl)carbamoyl]ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-amino-3-{[(1R)-1-[(2,2,4,4-tetramethylthietan-3-yl)carbamoyl]ethyl]carbamoyl}propanoic acid; alitame
• Synonyms: (S)-3-Amino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetramethylthietan-3-yl)amino)propan-2-yl)amino)butanoic acid; L-alpha-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide; Alitame; L-α-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide; CP 54802

Database IDs

• CAS Number: 80863-62-3
• MDL Number: MFCD00868124
• PubChem SID: 162036345
• PubChem CID: 64763
• Chemspider ID: 58297
• Unique Ingredient Identifier: 6KI9M51JOG
• Wikipedia Title: Alitame

CALCULATED PROPERTIES

• Acid pKa: 3.441787
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.8922005
• LogD (pH = 7.4): -2.9453313
• Log P: -2.8917203
• Molar Refractivity: 83.5821 cm^3
• Polarizability: 33.388428 Å^3
• Polar Surface Area: 121.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 132-137°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - A536500

Alitame is a dipeptide amide derivative of aspartic acid used as an artificial sweetener. Alitame is about ten times sweeter than Aspartame (A790015) with a half life about twice as long.

REFERENCES

• Glowaky, R.C. et al.: ACS. Symp. Ser., 450, 57 (1991)
• Hendrick, M.E. et al.: Adv. Sweet., 226 (1991)
• Auerbach, M.H. et al.: Food Sci. Technol., 112, 31 (1991)