Tetramic acid

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Structural formula
Diketo form
Structural formula of the diketo form
General
Surname Tetramic acid
other names
  • Pyrrolidine-2,4-dione
  • 2,4-pyrrolidinedione
  • 4-oxobutyrolactam
  • 1,5-dihydro-4-hydroxy-2 H -pyrrol-2-one
Molecular formula C 4 H 5 NO 2
Brief description

pale yellow solid

External identifiers / databases
CAS number
  • 37772-89-7 (2,4-pyrrolidinedione)
  • 503-83-3 (1,5-dihydro-4-hydroxy-2 H -pyrrol-2-one)
PubChem 54687243
Wikidata Q15632820
properties
Molar mass 99.09 g mol −1
Physical state

firmly

Melting point

> 360 ° C

pK s value

6.4

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The tetramic is a chemical compound from the group of pyrrolidine - derivatives and a β- keto - γ-butyrolactam .

Selection of tautomeric forms of tetramic acid.

It occurs in several tautomeric forms, but the diketo form is preferred. Tetramic acid can be viewed as a nitrogen analogue of tetronic acid , which also shows keto-enol tautomerism .

Tetramic acid itself is practically non-existent in nature in its free form, but it is widely used in derivatives in marine invertebrates such as sponges, slime molds and microorganisms , in which they perform various functions, e.g. For example, as dyes , meet. In humans, some tetramic acid as antibiotics ( cyclopiazonic , Magnesidin , tenuazonic acid ) or against leukemia cell lines ( Aurantosid A and Aurantosid B ) is effective.

Individual evidence

  1. ↑ a b c Entry on tetramic acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 19, 2013.
  2. ↑ entry to tetramic Acid in ChemicalBook , accessed on August 19, 2013.
  3. ↑ 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. 30 , urn : nbn: de: bvb: 703-opus-7699 (dissertation, University of Bayreuth).
  4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.