3-oxo-3H-phenoxazin-7-yl acetate

• ChemBase ID: 156025
• Molecular Formular: C14H9NO4
• Molecular Mass: 255.22556
• Monoisotopic Mass: 255.05315777
• SMILES: CC(=O)Oc1ccc2c(c1)oc1cc(=O)ccc1n2
• Canonical SMILES: CC(=O)Oc1ccc2c(c1)oc1c(n2)ccc(=O)c1
• InChI: InChI=1S/C14H9NO4/c1-8(16)18-10-3-5-12-14(7-10)19-13-6-9(17)2-4-11(13)15-12/h2-7H,1H3
• InChIKey: UJWKHDKBOVPINX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxo-3H-phenoxazin-7-yl acetate
• IUPAC Traditional name: 7-oxophenoxazin-3-yl acetate
• Synonyms: Resorufin acetate

Database IDs

• CAS Number: 1152-14-3
• MDL Number: MFCD00037659
• Beilstein Number: 246139
• PubChem SID: 162250163; 24888122
• PubChem CID: 3080579

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.6850156
• LogD (pH = 7.4): 1.6850157
• Log P: 1.6850157
• Molar Refractivity: 71.0761 cm^3
• Polarizability: 25.349115 Å^3
• Polar Surface Area: 64.96 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohols: soluble; DMF: soluble; DMSO: soluble
• Melting Point: 223 °C(lit.)
• Fluorescence: λex 500 nm; λem 593 nm in 0.1 M phosphate pH 8.0 (chymotrypsin); λex 540 nm; λem 590 nm in DMSO; λex 571 nm; λem 584 nm (Reaction product)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/22-36/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H332
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C14H9NO4

DETAILS

Sigma Aldrich - 83636

Application
suitable as fluorogenic substrate for hydrolytic enzymes (cellulases, chymotrypsin)
Other Notes
Studies on the esterase activity of cytosolic aldehyde dehydrogenase1