4H-PYRAN-4-ONE Chemical Properties

Melting point:

32-34 °C(lit.)

Boiling point:

210-215 °C(lit.)

Density 

1.20

refractive index 

1.5238

Flash point:

214 °F

storage temp. 

2-8°C

solubility 

Slightly soluble in water, soluble in alcohol and oils.

form 

clear liquid

color 

Light yellow to Brown

Odor

Warm, slight ly pungent, hay-like herbaceous odor of moderate to poor tenacity.

BRN 

105293

Stability:

Polymerizes under exposure to air (oxygen) and alkali. Turns darker brown, and its odor fades.

InChIKey

CVQUWLDCFXOXEN-UHFFFAOYSA-N

LogP

-0.628 (est)

CAS DataBase Reference

108-97-4

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-8-10

HS Code 

2932.99.9090

MSDS

• Language:English Provider:SigmaAldrich

4H-PYRAN-4-ONE Usage And Synthesis

Uses

4H-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
[2] Patent: EP1700853, 2006, A1. Location in patent: Page/Page column 12

4H-PYRAN-4-ONE(108-97-4)Related Product Information

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