2-[(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid

• ChemBase ID: 148297
• Molecular Formular: C13H14N2O4
• Molecular Mass: 262.26126
• Monoisotopic Mass: 262.09535694
• SMILES: c1ccc(cc1)C[C@H]1C(=O)N[C@H](C(=O)N1)CC(=O)O
• Canonical SMILES: OC(=O)C[C@@H]1NC(=O)[C@@H](NC1=O)Cc1ccccc1
• InChI: InChI=1S/C13H14N2O4/c16-11(17)7-10-13(19)14-9(12(18)15-10)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2,(H,14,19)(H,15,18)(H,16,17)/t9-,10-/m0/s1
• InChIKey: VNHJXYUDIBQDDX-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid
• IUPAC Traditional name: [(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid
• Synonyms: (2S-cis)-(-)-5-Benzyl-3,6-dioxo-2-piperazineacetic acid; (2S,5S)-3,6-Dioxo-5-(phenylmethyl)-2-piperazineacetic Acid; (2S-cis)-3,6-Dioxo-5-(phenylmethyl)-2-piperazineacetic Acid; (2S,5S)-5-Benzyl-3,6-dioxo-2-piperazineacetic Acid; (2S-顺式)-(-)-5-苄基-3,6-二氧-2-哌嗪乙酸

Database IDs

• CAS Number: 5262-10-2
• EC Number: 226-075-1
• MDL Number: MFCD00190764
• PubChem SID: 24866391; 162242473
• PubChem CID: 111054

CALCULATED PROPERTIES

• Acid pKa: 4.0504317
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.5196522
• LogD (pH = 7.4): -3.1881022
• Log P: -0.058523536
• Molar Refractivity: 65.2492 cm^3
• Polarizability: 25.499569 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 270-272 °C(lit.)
• Optical Rotation: [α]20/D -9.0°, c = 0.9 in acetic acid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C13H14N2O4

DETAILS

Sigma Aldrich - 421650

Packaging
1 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - B276305

The diketopiperazine impurity of the sweetening agent Aspartame (A790015). It is also found in in processed cocoa powder.

REFERENCES

• Bonvehi, J.S. et al.: Eur. Food. Res. Technol., 210, 189 (1983)
• Ciranni Signoretti, E. et al.: Boll. Chim. Farmac., 122, 289 (1983)
• Prudel, M. et al.: Nahrung, 29, 381 (1983)