Uses
4
H-Pyran-4-one was used in the synthesis of probes grafted on the lipid headgroups.
Preparation
1) from Diethylacetone dioxalate by cyclization to Chelidonic acid (gamma-Pyrone-
2,6-dicarboxylic acid). The acid yields 4H-Pyran-4-one by decarboxylation.
2) by heating of I-Methoxypent-l -en-3-yn-5-
al diethylacetal with Methanol and water,
using Mercuric sulfate or Sulfuric acid
catalyst.
Definition
ChEBI: A pyranone that is 4H-pyran substituted by an oxo group at position 4.
Synthesis
Example 1 (Synthesis of pyran-4-one): In a 10 mL glass reaction flask fitted with a stirring device and a dropping funnel, 1.0 g (4.8 mmol) of 1,1,5,5-tetramethoxypentan-3-one (CAS: 159015-78-8) was added. Under cooling in an ice bath, 1.2 mL (14.1 mmol) of 12 mol/L hydrochloric acid solution was slowly added dropwise to the reaction flask. After the dropwise addition, the reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method) to confirm the formation of 0.45 g (yield: 97%) of pyran-4-one.
Purification Methods
Purify -pyrone by vacuum distillation; the distillate crystallises and is hygroscopic. It is non-steam vola
References
[1] Patent: EP1700853, 2006, A1. Location in patent: Page/Page column 12
