Tetronic acid
Structural formula | |||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Structural formula of a tautomer (conjugated enol form) | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Tetronic acid | ||||||||||||||||||
other names |
Furan-2,4-dione |
||||||||||||||||||
Molecular formula | C 4 H 4 O 3 | ||||||||||||||||||
Brief description |
colorless, crystalline substance |
||||||||||||||||||
External identifiers / databases | |||||||||||||||||||
|
|||||||||||||||||||
properties | |||||||||||||||||||
Molar mass | 100.07 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
||||||||||||||||||
Melting point |
141 ° C |
||||||||||||||||||
pK s value |
3.76 |
||||||||||||||||||
solubility |
|
||||||||||||||||||
safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
The tetronic is a chemical substance from the group of γ- lactone . It results from the lactonization of 4-hydroxyacetoacetic acid . Technically, tetronic acid is obtained from ethyl 4-chloroacetoacetate . It occurs in several tautomeric forms.
Many natural substances, such as B. ascorbic acid or penicillanic acid have the β-keto-γ-butyrolactone structural motif of tetronic acid. Tetronic acid can be viewed as an oxygen analogue of tetramic acid , which also shows keto-enol tautomerism .
Individual evidence
- ↑ a b c d e Entry on tetronic acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 15, 2013.
- ↑ a b Bertram Barnickel: 3-functionalization of Tetron and tetramic: Contributions to the total synthesis of Bakkenolid-A and A Macrocidin . Bayreuth 2011, DNB 1010489143 , p. 13 , urn : nbn: de: bvb: 703-opus-7699 (dissertation, University of Bayreuth).
- ↑ a b Data sheet Tetronic acid, 96% from AlfaAesar, accessed on September 28, 2013 ( PDF )(JavaScript required) .
- ↑ Karl-Bernd Walter, Hans-Hartwig Otto: Nitrogen-containing derivatives of tetronic acid . In: Arch. Pharm. Band 320 , 1987, pp. 749-755 , doi : 10.1002 / ardp.19873200814 .