Aspergillic acid

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Structural formula
Aspergillic acid
Simplified structural formula without stereochemistry
General
Surname Aspergillic acid
other names
  • 6-butan-2-yl-1-hydroxy-3- (2-methylpropyl) pyrazin-2-one
  • 6- sec -Butyl-1-hydroxy-3-isobutyl-2 (1 H ) -pyrazinone
  • 6- sec -Butyl-3-isobutylpyrazinol-1-oxide
  • 2-Hydroxy-3-isobutyl-6- (1-methylpropyl) pyrazine-1-oxide
  • 3-isobutyl-6- sec- butyl-2-hydroxypyrazine-1-oxide
Molecular formula C 12 H 20 N 2 O 2
Brief description

pale yellow needles

External identifiers / databases
CAS number 490-02-8
PubChem 73679
Wikidata Q4807880
properties
Molar mass 224.30 g mol −1
Physical state

firmly

Melting point

97-99 ° C

safety instructions
GHS hazard labeling
no classification available
Toxicological data

4–5 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aspergillic acid is an antibiotic and fungicide made from some strains of Aspergillus flavus .

properties

Aspergillic acid is toxic, presumably partly as a chelator due to the binding of calcium ions. In mice, doses greater than 5 milligrams can cause convulsions and death. Aspergillic acid has reduced effectiveness in the presence of iron - ions .

presentation

Analogs of Aspergillus Acid

Aspergillic acid can be extracted from cell cultures . Different strains of aspergillus produce different analogs of aspergillic acid, e.g. B. Flavacol from Aspergillus flavus , which can then be hydroxylated by Aspergillus sclerotiorum at the nitrogen atom to neoaspergillic acid. Further hydroxylation produces neohydroxyaspergillic acid.

Breakdown of aspergillic acid

A total synthesis for racemic aspergillic acid has been described. Aspergillic acid can be broken down into leucine and isoleucine .

history

Edwin C. White and Justina H. Hill discovered a bactericidal activity against Gram-positive and Gram-negative bacteria in filtrates of tryptone- salt culture media in 1940 after a strain of Aspergillus flavus was cultured therein. Aspergillic acid was crystallized in 1943.

Individual evidence

  1. ↑ a b c d Entry on aspergillic acid. In: Römpp Online . Georg Thieme Verlag, accessed on January 17, 2015.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ a b c J.C. MacDonald: Biosynthesis of aspergillic acid. In: The Journal of Biological Chemistry . Volume 236, February 1961, ISSN  0021-9258 , pp. 512-514, PMID 13764736 .
  4. ↑ SS Deshpande: Handbook of Food Toxicology CRC Press, 2002. ISBN 9780203908969 .
  5. ↑ JC MacDonald: Toxicity, analysis, and production of aspergillic acid and its analogues. In: Canadian Journal of Biochemistry . Volume 51, Number 9, September 1973, ISSN  0008-4018 , pp. 1311-1315, PMID 4355132 .
  6. ↑ a b c Tadeusz Korzybski, Zuzanna Kowszyk-Gindifer, Wlodzimierz Kurylowicz: Antibiotics: Origin, Nature and Properties. Elsevier, 2013. ISBN 9781483223049 . P. 1279.
  7. ^ A b c Arnold Brossi: The Alkaloids: Chemistry and Pharmacology V29: Chemistry and Pharmacology , Volume 29. Academic Press, 1986. ISBN 9780080865539 . P. 190.
  8. ↑ a b J. D. Bu'Lock: Biosynthesis . Volume 5 of Biosynthesis: A Review of the Literature Published During 1970 and 1971, Chemical Society (Gran Bretaña) Royal Society of Chemistry, 1977. ISBN 9780851865430 . P. 252.
  9. ↑ Mitsuo Masaki, Yasuhiro Chigira, Masaki Ohta: Total Syntheses of Racemic Aspergillic Acid and Neoaspergillic Acid. In: The Journal of Organic Chemistry. 31, 1966, pp. 4143-4146, doi : 10.1021 / jo01350a062 .
  10. ^ Robert Alan Lewis: Lewis' Dictionary of Toxicology. CRC Press, 1998. ISBN 9781566702232 . P. 123.