Tenuazonic acid Copper Salt

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Category Mycotoxins
Catalog number BBF-05793
CAS 12427-40-6
Molecular Weight 455.99
Molecular Formula C20H28CuN2O6
Purity ≥98%

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Description

Tenuazonic Acid Copper Salt is an alternaria mycotoxin, found in common edible crops. It inhibits protein synthesis in fibroblasts.

Specification

Related CAS 610-88-8 (free acid) 12427-40-6 (hydrate)
Synonyms 3-Pyrrolin-2-one, 3-acetyl-5-sec-butyl-4-hydroxy-, L-, Copper Salt; L-3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one Copper Salt; (5S)-3-Acetyl-1,5-dihydro-4-hydroxy-5-[(1S)-1-methylpropyl]-2H-pyrrol-2-one Copper Salt; AAC-toxin Copper Salt; L-Tenuazonic Acid Copper Salt
Storage Store at 2-8°C
IUPAC Name copper(II) (S)-4-acetyl-2-((S)-sec-butyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-olate
Canonical SMILES CCC(C)C1C(=C(C(=O)N1)C(=O)C)O[Cu]OC2=C(C(=O)NC2C(C)CC)C(=O)C
InChI InChI=1S/2C10H15NO3.Cu/c2*1-4-5(2)8-9(13)7(6(3)12)10(14)11-8;/h2*5,8,13H,4H2,1-3H3,(H,11,14);/q;;+2/p-2
InChI Key IAHMFKOQYRRWFU-UHFFFAOYSA-L

Properties

Appearance Light Blue-greenish Powder
Melting Point >140°C (dec.)
Solubility Soluble in DMSO, Pure Ethanol, Chloroform (Slightly), Methanol (Slightly)

Reference Reading

1. Biosynthesis and preparation of fiveAlternaria metabolites
M Kostecki, J Grabarkiewicz-Szczęsna, J Chelkowski Mycotoxin Res. 1991 Mar;7(1):3-7. doi: 10.1007/BF03192156.
Metabolites ofAlternaria alternata were produced on rice as a solid substrate, chosen out of 6 substrates as the most useful. Optimal methods of extraction, purification, and separation of 5 metabolites were elaborated, using liquid - liquid partition, column chromatography, and preparative TLC. Alternariol, alternariol methyl ether, and copper salt of tenuazonic acid were obtained as crystals, altertoxin and altenuene as a film.

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