Penicillic acid

Penicillic acid
Skeletal formulas of two tautomers
Ball-and-stick model
Names
IUPAC name
5-Hydroxy-5-isopropenyl-4-methoxy-furan-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.826
EC Number
  • 202-008-1
KEGG
UNII
  • InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4-
    Key: VOUGEZYPVGAPBB-XQRVVYSFSA-N
  • CC(=C)C1(C=CC(=O)O1)O
Properties
C8H10O4
Molar mass 170.164 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Penicillic acid is a mycotoxin that is produced by Aspergillus flavus, Aspergillus ostianus and Penicillium roqueforti mold. It is not a product of acid degradation of penicillin.Biosynthesis of the compound has been stablished ( http://dx.doi.org/10.1038/s41467-024-52101-2 ). 

Its first practical synthesis was reported in 1947 by Ralph Raphael, who had worked on penicillin during World War II.[1]

References

  1. ^ Raphael, Ralph (1947). "Synthesis of the Antibiotic, Penicillic Acid". Nature. 160 (4060): 261–262. Bibcode:1947Natur.160..261R. doi:10.1038/160261c0. PMID 20344393. S2CID 4066740.


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