Tenuazonic acid (Cu salt)

Molecular Formula:

C20H28CuN2O6

CAS number:

12427-40-6

Fermentek product code:

TNZ

Source:

Alternaria sp.

Brand/grade:

For research

Specifications

Appearance:

Light blue-greenish powder

Purity by HPLC:

≥98% ; refer to CoA for more data

Purity By TLC:

≥98% ; refer to CoA for more data

Solubility test:

Clear blue-green solution at 10mg/ml Dichloromethane

Chemical identification

Names and identifiers:

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.

Description:

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.

Molecular weight:

455.99

InChl Key:

LLXUERDQXVXQAY-UHFFFAOYSA-N

Canonical SMILES:

CCC(C)C1C(=C(C(=O)N1)C(=O)C)O.CCC(C)C1C(=C(C(=O)N1)C(=O)C)O.[Cu]

Further Information

Solubility ( literature ):

Soluble in DMSO, pure ethanol, methanol

Compound Classification:

Pyrrolidinone mycotoxin
Antineoplastic agent
Acetylcholinesterase inhibitor
Inhibits natural photosystem II.

Storage, handling:

Store in a freezer upon arrival, at -10°C to -25°C

Keep the lid tightly closed.

Avoid exposing to strong direct light.

Other vendors may recommend higher temperatures for storage.

Applications:

Potential antineoplastic agent,
Used in research on Alzheimer’s Disease treatment
Potential herbicide.

Disclaimer:

For Research use only

Not for Human or Drug use

Not extracted from humans or animals

Refer to MSDS for further safety and handling instructions

Semi-Synthetic

Composition

Ingredient type:

Fermentek product

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

Special Info

Available since:

2013

Other Fields

Title:

Transport information

Value:

Pg III