(2S)-5-oxooxolane-2-carboxylic acid

• ChemBase ID: 79620
• Molecular Formular: C5H6O4
• Molecular Mass: 130.09874
• Monoisotopic Mass: 130.02660867
• SMILES: O1C(=O)CC[C@H]1C(=O)O
• Canonical SMILES: O=C1CC[C@H](O1)C(=O)O
• InChI: InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m0/s1
• InChIKey: QVADRSWDTZDDGR-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-oxooxolane-2-carboxylic acid
• IUPAC Traditional name: (2S)-5-oxooxolane-2-carboxylic acid
• Synonyms: (2S)-(+)-2-Carboxy-5-oxotetrahydrofuran; (S)-gamma-Carboxy-gamma-butyrolactone; (2S)-(+)-5-Oxotetrahydrofuran-2-carboxylic acid; 5-oxotetrahydrofuran-2-carboxylic acid; (S)-γ-Carboxy-γ-butyrolactone; (S)-5-Oxotetrahydro-2-furancarboxylic acid; (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid; (S)-5-Oxo-tetrahydrofuran-2-carboxylic acid; (2S)-Tetrahydro-5-oxo-2-furancarboxylic Acid; (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic Acid; (2S)-Tetrahydro-5-oxofuran-2-carboxylic Acid; (S)-Tetrahydro-5-oxo-2-furancarboxylic Acid; 5S-(+)-Butyrolactone Carboxylic Acid; (S)-5-Oxo-2-tetrahydrofurancarboxylic Acid; (S)-5-Oxotetrahydro-2-furancarboxylic acid; (S)-γ-羧基-γ-丁内酯; (S)-5-氧代四氢-2-呋喃羧酸; (S)-(+)-5-氧代-2-四氢呋喃羧酸; (S)-5-氧代四氢-2-呋喃羧酸

Database IDs

• CAS Number: 21461-84-7
• MDL Number: MFCD00064516
• Beilstein Number: 1424498
• PubChem SID: 162044383; 24858189
• PubChem CID: 636468

CALCULATED PROPERTIES

• Acid pKa: 3.3285491
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.316238
• LogD (pH = 7.4): -3.580405
• Log P: -0.1605091
• Molar Refractivity: 26.138 cm^3
• Polarizability: 10.711061 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone
• Apperance: White Solid
• Melting Point: 68-72 °C; 71-73 °C(lit.); 71-73°C
• Boiling Point: 150-155 °C/0.2 mmHg(lit.); 150-155°C/0.3mm
• Optical Rotation: [α]20/D +14°, c = 5 in methanol; [α]20/D +16±1°, c = 2% in ethanol

Safety Information

• Storage Warning: Irritant
• 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: ≥98.0% (T); 97%; 98%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C5H6O4

DETAILS

Sigma Aldrich - 301469

Packaging
1, 5 g in glass bottle
Application
Used to prepare municatacin analogs which show cytotoxic activity on tumor cells.1

Sigma Aldrich - 75947

Other Notes
Chiral building block, review1; Synthesis of 2′,3′-dideoxynucleosides2; Derivatizing agent for the determination of the enantiomeric purity of alcohols3