Penicillic acid is a mycotoxin produced by a number of species of the genera Penicillium and Aspergillus .
| Penicillic acid | |
|---|---|
 | |
| Are common | |
| Systematic name | (2Z) -3-methoxy-5-methyl-4-oxo-2,5-hexadiene acid |
| Chem. formula | C 8 H 10 O 4 |
| Physical properties | |
| Molar mass | 170.163 g / mol |
| Thermal properties | |
| T. melt. | 83 ° C |
| Classification | |
| Reg. CAS number | 90-65-3 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| ChemSpider | |
Content
Properties
It exists in the form of two tautomeric forms - γ-keto acid and γ-hydroxylactone, which was shown in 1936.
From pentane , hexane and benzene it crystallizes with the formation of anhydrous needle crystals with a melting point of 83–85 ° C. It crystallizes from water to form a monohydrate in the form of large monoclinic or triclinic rhombic crystals with a melting point of 58–64 ° C.
Solubility in cold water and cold benzene is 2%. It is soluble in hot water, alcohol, ether, chloroform , insoluble in pentano-hexane mixture.
In the alkali forms a bright red complex compound with hydroxylamine with a maximum absorption at 530 nm. With ammonium forms a reddish-purple complex with a maximum absorption at 545 nm.
An intermediate product in the biosynthesis of penicillic acid is orsellic acid .
History
Oxford and colleagues in 1942 investigated the antimicrobial activity of penicillic acid. The substance has been shown to be active against gram-negative and some gram-positive bacteria. The substance was too toxic (LD 50 for mice with subcutaneous administration - 100 mg / kg).
Chemically synthesized in 1947 by Ralph Raphael .
Penicillic acid was shown to be a powerful carcinogen in the 1960s.
Notes
Literature
- Microbial Toxins: A Comprehensive Treatise / A. Ciegler, S. Kadis, SJ Ajl (eds.). - New York; London, 1971. - Vol. VI. Fungal Toxins. - P. 414-420.