(2S)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

• ChemBase ID: 69648
• Molecular Formular: C5H7NO2
• Molecular Mass: 113.11458
• Monoisotopic Mass: 113.04767847
• SMILES: N1[C@@H](C=CC1)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1NCC=C1
• InChI: InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h1-2,4,6H,3H2,(H,7,8)/t4-/m0/s1
• InChIKey: OMGHIGVFLOPEHJ-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,5-dihydro-1H-pyrrole-2-carboxylic acid
• IUPAC Traditional name: (2S)-2,5-dihydro-1H-pyrrole-2-carboxylic acid
• Synonyms: 3,4-Dehydro-L-proline; 3,4-Dehydro-L-proline; (S)-3-Pyrroline-2-carboxylic acid; 3,4-Didehydro-L-proline; (S)-2,5-Dihydro-1H-pyrrole-2-carboxylic acid; (S)-3-吡咯啉-2-羧酸; 3,4-二脱氢-L-脯氨酸; 3,4-脱氢-L-脯氨酸

Database IDs

• CAS Number: 4043-88-3
• EC Number: 223-738-7
• MDL Number: MFCD00065964
• Beilstein Number: 5376764
• PubChem SID: 162035374; 24893903
• PubChem CID: 94284

CALCULATED PROPERTIES

• Acid pKa: 1.7623979
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.6187618
• LogD (pH = 7.4): -2.6189113
• Log P: -2.6187227
• Molar Refractivity: 28.8729 cm^3
• Polarizability: 11.044176 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 239-241 °C (dec.); 248-250 °C(lit.)
• Optical Rotation: [α]20/D -385°, c = 2 in H2O; [α]20/D -400±10°, c = 0.2% in H2O

Safety Information

• Storage Warning: IRRITANT
• RTECS: UX9371345
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 95+%; 98%
• Empirical Formula (Hill Notation): C5H7NO2

DETAILS

Sigma Aldrich - D4893

包装
10, 50 mg in poly bottle

Sigma Aldrich - 30890

Other Notes
Review: Analogs and homologs of proline and hydroxyproline1