| Identification | Back Directory | [Name]
4H-PYRAN-4-ONE | [CAS]
108-97-4 | [Synonyms]
4-Pyrone
Pyrocoman
PYRAN-4-ONE
GAMMA-PYRONE
4H-PYRAN-4-ONE
4H-Pyran, 4-oxo-
4H-PYRAN-4-ONE, 98+%
4H-Pyran-4-one
GAMMA-PYRONE, 4-PYRONE | [EINECS(EC#)]
203-634-8 | [Molecular Formula]
C5H4O2 | [MDL Number]
MFCD00006576 | [MOL File]
108-97-4.mol | [Molecular Weight]
96.08 |
| Chemical Properties | Back Directory | [Melting point ]
32-34 °C(lit.)
| [Boiling point ]
210-215 °C(lit.)
| [density ]
1.20 | [refractive index ]
1.5238 | [Fp ]
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 |
| Hazard Information | Back Directory | [Definition]
ChEBI: A pyranone that is 4H-pyran substituted by an oxo group at position 4. | [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.
| [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 |
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