(3S)-3-amino-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propanoic acid

• ChemBase ID: 131909
• Molecular Formular: C13H16N2O5
• Molecular Mass: 280.27654
• Monoisotopic Mass: 280.10592162
• SMILES: c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)N
• Canonical SMILES: OC(=O)C[C@@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)N
• InChI: InChI=1S/C13H16N2O5/c14-9(7-11(16)17)12(18)15-10(13(19)20)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,14H2,(H,15,18)(H,16,17)(H,19,20)/t9-,10-/m0/s1
• InChIKey: YZQCXOFQZKCETR-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: L-aspartyl-L-phenylalanine
• Synonyms: L-α-Aspartyl-L-phenylalanine; N-L-α-Aspartyl-L-phenylalanine; Demethylaspartame; α-Aspartylphenylalanine; α-L-Aspartyl-L-phenylalanine; Thiamine Impurity B; L-Aspartyl-L-phenylalanine; L-Aspartyl-L-phenylalanine; Aspartame acid; Asp-Phe; L-天冬氨酰-L-苯丙氨酸; 阿斯巴甜酸; 天冬氨酰-苯丙氨酸

Database IDs

• CAS Number: 13433-09-5
• EC Number: 236-557-3
• MDL Number: MFCD00063155
• Beilstein Number: 2817528
• PubChem SID: 162226186; 24866392
• PubChem CID: 93078

CALCULATED PROPERTIES

• Acid pKa: 3.1651475
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.0073814
• LogD (pH = 7.4): -5.6260757
• Log P: -2.7545905
• Molar Refractivity: 68.4491 cm^3
• Polarizability: 27.079271 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 236-239 °C(lit.)
• Optical Rotation: [α]20/D +12.5°, c = 1 in 0.5 M HCl

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 96%
• Linear Formula: HOOCCH2CH(NH2)CONHCH(CH2C6H5)CO2H

DETAILS

Sigma Aldrich - 421669

Packaging
100, 250 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 421669.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A790010

L-Aspartyl-L-phenylalanine is an impurity of Thiamine (T344185). Thiamine Impurity B.

REFERENCES

• Aluwihare, L., et al.: Science, 308, 1007 (2005)
• Koch, B., et al.: Anal. Chem., 79, 1758 (2005)
• Reemtsma, T., et al.: Environ. Sci. Technol., 42, 1430 (2005)