(4S)-4-benzyl-3-(but-2-enoyl)-1,3-oxazolidin-2-one

• ChemBase ID: 135413
• Molecular Formular: C14H15NO3
• Molecular Mass: 245.2738
• Monoisotopic Mass: 245.10519335
• SMILES: C/C=C/C(=O)N1[C@H](COC1=O)Cc1ccccc1
• Canonical SMILES: C/C=C/C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1
• InChI: InChI=1S/C14H15NO3/c1-2-6-13(16)15-12(10-18-14(15)17)9-11-7-4-3-5-8-11/h2-8,12H,9-10H2,1H3/t12-/m0/s1
• InChIKey: UTZAFVPPWUIPBH-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-benzyl-3-(but-2-enoyl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-benzyl-3-(but-2-enoyl)-1,3-oxazolidin-2-one
• Synonyms: (N-Crotonyl)-(4S)-benzyl-2-oxazolidinone; (S)-(+)-4-Benzyl-3-crotonyl-2-oxazolidinone; Locostatin; (4S)-3-[(E)-1-Oxo-2-butenyl]-4-(phenylmethyl)-2-oxazolidinone; (4S)-3-[(E)-But-2-enoyl]-4-benzyl-2-oxazolidinone; UIC-1005; (N-巴豆酰)-(4S)-苄基-2-噁唑烷酮; (S)-(+)-4-苄基-3-巴豆酰-2-噁唑烷酮

Database IDs

• CAS Number: 90719-30-5; 133812-16-5
• MDL Number: MFCD00278769
• PubChem SID: 162229687; 24878077
• PubChem CID: 5702600

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.8455915
• LogD (pH = 7.4): 2.8455915
• Log P: 2.8455915
• Molar Refractivity: 67.9421 cm^3
• Polarizability: 26.067081 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥30 mg/mL
• Apperance: white to off-white powder
• Melting Point: 84-88 °C(lit.)
• Optical Rotation: [α]20/D +76°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 97%
• Empirical Formula (Hill Notation): C14H15NO3

DETAILS

Sigma Aldrich - L5670

Biochem/physiol Actions
Locostatin is a cell permeable, potent inhibitor of Raf kinase inhibitor protein (RKIP)/Raf1 kinase interaction and an inhibitor of cell migration.