(2S)-azetidine-2-carboxylic acid

• ChemBase ID: 63597
• Molecular Formular: C4H7NO2
• Molecular Mass: 101.10388
• Monoisotopic Mass: 101.04767847
• SMILES: [C@H]1(C(=O)O)NCC1
• Canonical SMILES: OC(=O)[C@@H]1CCN1
• InChI: InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
• InChIKey: IADUEWIQBXOCDZ-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-azetidine-2-carboxylic acid
• IUPAC Traditional name: L-azetidine 2-carboxylic acid
• Synonyms: (S)-(-) Azetidine-2-carboxylic acid; L-Azetidine-2-carboxylic acid; (S)-Azetidine-2-carboxylic acid; L-Azetidine-2-carboxylic acid; H-Aze-OH; (S)-(-)-Azetidine-2-carboxylic acid; Azetidine-2-carboxylic acid; (S)-(-)-氮杂环丁烷-2-甲酸

Database IDs

• CAS Number: 2133-34-8
• EC Number: 218-362-5
• MDL Number: MFCD00005166
• Beilstein Number: 80680; 80678
• Merck Index: 14908
• PubChem SID: 24278205; 162029336; 24847213
• PubChem CID: 16486
• CHEBI ID: 6198
• CHEMBL: 1165239
• Chemspider ID: 15628
• Wikipedia Title: Azetidine-2-carboxylic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.7564697
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.0860164
• LogD (pH = 7.4): -3.0861597
• Log P: -3.0859778
• Molar Refractivity: 23.4197 cm^3
• Polarizability: 9.473591 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 5.0 g/100 ml in water
• Apperance: crystalline solid
• Melting Point: ~215 °C (dec.); 215°C; ca 217°C dec.
• Boiling Point: 242°C
• Flash Point: 100.1 °C
• Density: 1.275 g/cm3
• Optical Rotation: [α]20/D -123±2°, c = 4% in H2O; -123 (c=4 in H2O)

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: CM4310500
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: >95%; ≥98.0% (NT); ≥99%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C4H7NO2

DETAILS

Apollo Scientific Ltd - OR1250T

A four-membered ring analog of L-Proline used as an intermediate in the synthesis of polypeptides.

Sigma Aldrich - A0760

Packaging
1 g in poly bottle
50, 100, 250 mg in poly bottle
Biochem/physiol Actions
L-Azetidine-2-carboxylic acid is an inhibitor of collagen synthesis that is anti-angiogenic. It is a four-membered ring analog of L-proline that causes protein misconstruction when incorporated instead of proline.

Sigma Aldrich - 11542

Other Notes
Preparation of mugineic acid1; 4-Oxidation to the corresponding lactam2
Biochem/physiol Actions
L-Azetidine-2-carboxylic acid is an inhibitor of collagen synthesis that is anti-angiogenic. It is a four-membered ring analog of L-proline that causes protein misconstruction when incorporated instead of proline.