(3S)-3-aminooxolan-2-one hydrochloride

• ChemBase ID: 69394
• Molecular Formular: C4H8ClNO2
• Molecular Mass: 137.56482
• Monoisotopic Mass: 137.02435618
• SMILES: C1(=O)[C@@H](N)CCO1.Cl
• Canonical SMILES: O=C1OCC[C@@H]1N.Cl
• InChI: InChI=1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
• InChIKey: XBKCXPRYTLOQKS-DFWYDOINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-aminooxolan-2-one hydrochloride
• IUPAC Traditional name: L-homoserine lactone group hydrochloride; L-homoserine lactone hydrochloride
• Synonyms: HSI; L-Homoserine lactone hydrochloride; (S)-α-Amino-γ-butyrolactone hydrochloride; (S)-Homoserine-lactone hydrochloride; L-Homoserine lactone hydrochloride; (S)-Homoserine Lactone Hydrochloride; L-Homoserine Lactone, Hydrochloride; (3S)-3-Aminodihydro-2(3H)-furanone Hydrochloride; L-高丝氨酸内酯 盐酸盐; (S)-α-氨基-γ-丁内酯 盐酸盐; L-高丝氨酸内酯 盐酸盐

Database IDs

• CAS Number: 2185-03-7; 2185-02-6
• EC Number: 218-571-1
• MDL Number: MFCD00058172
• Beilstein Number: 3562187
• PubChem SID: 24869524; 162035120; 24846043; 24895811
• PubChem CID: 2733667

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.7108617
• LogD (pH = 7.4): -1.1681297
• Log P: -0.9011904
• Molar Refractivity: 23.4142 cm^3
• Polarizability: 9.7096 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly Soluble in Ethanol; Water
• Apperance: White Solid
• Melting Point: >230°C dec.; 210-220 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -27.5±1°, c = 1% in H2O; [α]20/D -27.8°, c = 1 in H2O

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, TLC); 95+%; 97%
• Empirical Formula (Hill Notation): C4H7NO2 · HCl

DETAILS

Sigma Aldrich - 459224

Packaging
1 g in glass bottle

Sigma Aldrich - 07254

Other Notes
Chiral building block; opening of the lactone to the bromo ester and N-protection proceeds without racemization1,2; Synthesis of (S,S)-2,5-diaminoadipate3