Tetronic acid
| Structural formula | |||||||||||||||||||
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| Structural formula of a tautomer (conjugated enol form) | |||||||||||||||||||
| General | |||||||||||||||||||
| Surname | Tetronic acid | ||||||||||||||||||
| other names |
Furan-2,4-dione |
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| Molecular formula | C 4 H 4 O 3 | ||||||||||||||||||
| Brief description |
colorless, crystalline substance |
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| properties | |||||||||||||||||||
| Molar mass | 100.07 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
141 ° C |
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| pK s value |
3.76 |
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| solubility |
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| safety instructions | |||||||||||||||||||
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| 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 .