5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one

• ChemBase ID: 154083
• Molecular Formular: C11H13NO3
• Molecular Mass: 207.22582
• Monoisotopic Mass: 207.08954328
• SMILES: Cc1cccc(c1)N1CC(OC1=O)CO
• Canonical SMILES: OCC1OC(=O)N(C1)c1cccc(c1)C
• InChI: InChI=1S/C11H13NO3/c1-8-3-2-4-9(5-8)12-6-10(7-13)15-11(12)14/h2-5,10,13H,6-7H2,1H3
• InChIKey: MXUNKHLAEDCYJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: toloxatone
• Synonyms: 5-(hydroxymethyl)-3-(3-methylphenyl)-2-oxazolidinone; Humoryl; Toloxatone

Database IDs

• CAS Number: 29218-27-7
• EC Number: 249-522-2
• MDL Number: MFCD00865391
• PubChem SID: 162248222
• PubChem CID: 34521

CALCULATED PROPERTIES

• Acid pKa: 14.608045
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4058748
• LogD (pH = 7.4): 1.4058748
• Log P: 1.4058748
• Molar Refractivity: 54.6952 cm^3
• Polarizability: 21.257605 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: solid

Safety Information

• Storage Condition: desiccated
• RTECS: RQ2867500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H13NO3

DETAILS

Sigma Aldrich - T3452

Biochem/physiol Actions
Toloxatone is a reversible monoamine oxidase A inhibitor (MAOI) and antidepressant. Toloxatone belongs to the aryloxazolidinones, a relatively new class of reversible monoamine oxidase A inhibitors (MAOI). Studies show that derivatives such as 3-aryloxazolidin-2-one (oxazolidinones), which are regularly used to treat gram positive infections, represent a new class of reversible as well as irreversible inhibitors for MAO-A and MAO-B enzymes that are able to inhibit protein synthesis and also used for neurodegenerative-type pathologies.