Umbelliferone → 7-Ethoxycoumarin

HRID 1920621

Reaction equation

HRID 1920621 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.O[C:14]1C=C2C(C=CC(=O)O2)=C[CH:15]=1.S([O-])([O-])(=O)=O>CO.O>[CH2:14]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)[CH3:15]

Participants

5

Reactant 2

HCID 5281426Umbelliferone2×HCID 21972050HCID 21972050, compound

Product 1

HCID 357037-Ethoxycoumarin

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent4×HCID 962WaterSolvent7×

Procedure

Four standards were used: 7-ethoxycoumarin, which was prepared as 1 mg/ml solution in methanol, and 10 μg/ml solutions prepared from the 1 mg/ml solutions in distilled water; the Phase I metabolite of ECOD, 7-hydroxycoumarin (7-HC), which was prepared as a 1 mg/ml solution in 50:50 methanol:water, and 10 μg/ml solutions diluted in distilled water; the Phase II metabolite, 7-HC-glucuronide, which was prepared as a 1 mg/ml solution in 50:50 methanol:water, and subsequently diluted in distilled water to yield a 10 μg/ml solution; and 7-HC-sulphate, prepared as a 1 mg/ml solution in 50:50 methanol:water, and subsequently diluted in distilled water to yield a 10 μg/ml solution. ECOD elutes between 12.919 to 14.647 minutes from the column, while 7-HC elutes at 3.709 to 4.668 minutes. The subsequent breakdown product, 7HC-glucuronide, is retained at 2.265 to 3.947 minutes, and 7HC-sulphate is retained from 10.230 to 12.878 minutes.

Workup

  1. customto yield a 10 μg/ml solution
  2. customto yield a 10 μg/ml solution

Sources & evidence

ORD record
ord-7ecdf86727214a59a249099702a4e45c
Source dataset
uspto-grants-2012_05
Patent number
US08173361B2

Linked notes

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