Tenuazonic acid

Tenuazonic acid

Names
IUPAC name (5S)-3-Acetyl-5-[(2S)-butan-2-yl]-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one[1]
Identifiers
CAS Number	610-88-8
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL511015
ECHA InfoCard	100.164.201
PubChem	101949
SMILES O=C1C(C(C)=O)=C(O)[C@@]([C@H](CC)C)([H])N1
Properties
Chemical formula	C10H15NO3
Molar mass	197.23 g·mol^−1
Appearance	White crystalline powder
Acidity (pKa)	3.5
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	* 182 mg kg^−1 (Mice, ♂, oral)[2] 225 mg kg^−1 (Mice, ♂, oral)[3] 81 mg kg^−1 (Mice, ♀, oral)[2]
Pharmacology
Routes of administration	Ingested or Inhaled
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Tenuazonic acid is a mycotoxin produced by Alternaria species.^[4] It is a powerful eukaryotic protein synthesis inhibitor.^[5]

In 1991 Tenuazonic acid was reported to inhibit skin tumor promotion in mice.^[6]

References

1. "Tenuazonic Acid". Cayman Chemical.
2. Miller, F. A. et al.; Nature, 200 (1963), S. 1338–1339
3. Smith, E. R. et al.; Cancer Chemother. Rep. 52 (1968), S. 579–585.
4. Alisa D. Hocking (Editor), John I. Pitt (Editor) and Robert A. Samson (Editor): Advances in Food Mycology. Springer 2006; ISBN 978-0-387-28385-2; p. 23
5. Dilip K. Arora and Arora K. Arora: Fungal Biotechnology in Agricultural, Food, and Environmental Applications. Marcel Dekker Inc; illustrated edition 2003; ISBN 978-0-8247-4770-1; p. 336
6. Tenuazonic acid page from Fermentek