diethyl 2-oxo-2H-chromen-7-yl phosphate

• ChemBase ID: 155010
• Molecular Formular: C13H15O6P
• Molecular Mass: 298.228361
• Monoisotopic Mass: 298.06062483
• SMILES: CCOP(=O)(OCC)Oc1ccc2ccc(=O)oc2c1
• Canonical SMILES: CCOP(=O)(Oc1ccc2c(c1)oc(=O)cc2)OCC
• InChI: InChI=1S/C13H15O6P/c1-3-16-20(15,17-4-2)19-11-7-5-10-6-8-13(14)18-12(10)9-11/h5-9H,3-4H2,1-2H3
• InChIKey: LZXQXHKDCNQUOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl 2-oxo-2H-chromen-7-yl phosphate
• IUPAC Traditional name: diethyl 2-oxochromen-7-yl phosphate
• Synonyms: DEUP; UBP; Diethylumbelliferyl phosphate

Database IDs

• CAS Number: 897-83-6
• PubChem SID: 24894155; 162249148
• PubChem CID: 16219277

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.2954664
• LogD (pH = 7.4): 2.2954664
• Log P: 2.2954664
• Molar Refractivity: 72.8642 cm^3
• Polarizability: 28.504896 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: colorless to yellow oil

Safety Information

• RTECS: GN7350000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H17O6P

DETAILS

Sigma Aldrich - D7692

Biochem/physiol Actions
Diethylumbelliferyl phosphate is a selective, potent cholesterol esterase inhibitor. It blocks steroidogenesis primarily by preventing cholesterol transport into the mitochondria of steroidogenic cells. Inhibitors of cholesterol esterase are anticipated to limit the absorption of dietary cholesterol. IC50 = 11.6 μM.