April 25, 2024, 06:23:05 PM
Forum Rules: Read This Before Posting


Topic: 6-hydroxy-2H-pyran-3(6H)-one: INSTABILITY IN WATER  (Read 1753 times)

0 Members and 1 Guest are viewing this topic.

Offline STM

  • Regular Member
  • ***
  • Posts: 45
  • Mole Snacks: +0/-0
6-hydroxy-2H-pyran-3(6H)-one: INSTABILITY IN WATER
« on: June 26, 2017, 04:13:45 AM »
I recently purchased 6-hydroxy-2h-pyran-3(6h)-one and prepared its stock solution in water after which i prepared some standard solution for calibration. This compound is the product of reaction between Furfuryl alcohol and singlet oxygen.

My purpose was to identify its peak from the chromatogram and also quantify it.

I prepared the calibration curve immediately using the freshly prepared stock and standard solution. I obtained a slope (about 30, 000).

I retained the stock solution, stored in the dark in brown borosilicate bottle  and used it the some few days after for calibration. Surprisingly, the signal I got this time had reduced greatly (about 2 orders) for each standard solution signifying decomposition of the compound.

Please can someone educate me further on why this compound behaved so. There is no suggestion in literature on any special storage or preservation for it.

This is important for my work as it can greatly affect my calculations.

Thank you

Offline pgk

  • Chemist
  • Full Member
  • *
  • Posts: 892
  • Mole Snacks: +97/-24
Re: 6-hydroxy-2H-pyran-3(6H)-one: INSTABILITY IN WATER
« Reply #1 on: June 27, 2017, 10:57:40 AM »
Regardless the preparation method, 6-hydroxy-2H-pyran-3(6H)-one is the intramolecular hemiacetal of 5-hydroxy-4-oxo-2-pentenal.
HOCH2COCH=CHCH=O
As a consequence, 6-hydroxy-2H-pyran-3(6H)-one is quickly hydrolyzed to the “mother” compound (5-hydroxy-4-oxo-2-pentenal).
Acetals and hemacetals are instable in acidic medium but relatively stable in neutral and alkaline medium.
So, try to neutralize the medium or alkalize with a little amount of Na2Co3 (if being compatible) and see if you get a better aqueous stability.

Sponsored Links