Specifications
Chemical identification
Synonyms:
- (5S)-3-acetyl-5-[(2S)-butan-2-yl]-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one, copper salt
- Tenuazonic acid, copper salt
- 3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one , copper salt
- Copper, bis[3-acetyl-5-(1-methylpropyl)-2,4-pyrrolidinedionato-O3,O4]
- Copper(2+) bis{(2S)-4-acetyl-2-[(2S)-2-butanyl]-5-oxo-2,5-dihydro-1H-pyrrol-3-olate} ...[ACD/IUPAC Name]
- AAC-toxin (Copper salt)
RTECS: UY7425000
Disambiguation:
There are more variants of Tenuazonic acid:
- CAS 610-88-8 Tenuazonic acid free acid form, C10H15NO3
- 12427-40-6 Tenuazonic acid C20H28CuN2O6.H2O copper salt monohydrate
- 76569-74-9 Tenuazonic acid copper salt C20H28CuN2O6 anhydrous
Some vendors offer Tenuazonic acid, copper salt, but specify CAS RN 610-88-8 belonging to the free acid form.
The EU (ECHA) number which is given below, 636-400-2, belongs to the free acid form. The copper salt form is not registered by ECHA.
Tenuazonic acid is a natural mycotoxin, an inhibitor of protein synthesis. Tenuazonic Acid is an antineoplastic agent and mycotoxin. It Inhibits protein synthesis. It has been shown to inhibit TPA-induced ornithine decarboxylase activity. Lack of ornithine decarboxylase eventually causes DNA damage-induced apoptosis. It has also been shown to inhibit photosystem II.
Tenuazonic acid is offered as its Cuprum salt.
Further Information
Soluble in DMSO, pure ethanol, methanol
- Pyrrolidinone mycotoxin
- Antineoplastic agent
- Acetylcholinesterase inhibitor
- Inhibits natural photosystem II.
Potential antineoplastic agent,
Used in research on Alzheimer’s Disease treatment
Potential herbicide.
Composition
Publications
J. Med. Chem. 1965, 8, 4, 483–486
https://doi.org/10.1021/jm00328a015
Antitumor, Cytotoxic, and Antibacterial Activities of Tenuazonic Acid and Congeneric Tetramic Acids
C. O. Gitterman
Molecules (Basel, Switzerland). 23 (9): 2182.
doi:10.3390/molecules23092182.. PMC 6225478. PMID 30158491
Natural Scaffolds with Multi-Target Activity for the Potential Treatment of Alzheimer's Disease
Piemontese, Luca; Vitucci, Gabriele; Catto, Marco; Laghezza, Antonio; Perna, Filippo Maria; Rullo, Mariagrazia; Loiodice, Fulvio; Capriati, Vito; Solfrizzo, Michele
.