Tenuazonic acid

Tenuazonic acid

Names
Other names 5S,6S-3-acetyl-5-sec-butyl-4-hydroxypyrrolidone-2,4-dione
Identifiers
CAS Registry Number	610-88-8 Y
ChEMBL	ChEMBL511015 N
Jmol-3D images	Image
PubChem	101949
SMILES CCC(C)C1C(=O)C(=C(N1)O)C(=O)C
Properties
Chemical formula	C10H15NO3
Molar mass	197.231
Appearance	colorless, oily substance
Acidity (pKa)	3.5
Pharmacology
Routes of administration	Ingested or Inhaled
Legal status	no legal status yet
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Tenuazonic acid is a mycotoxin. It is a toxic secondary metabolite, produced by Alternaria (e. g. Alternaria alternata or Alternaria tenuis) and Phoma species.^[1] It inhibits the protein synthesis machinery.^[2]

Tenuazonic acid or 5S,6S-3-acetyl-5-sec-butyl-4-hydroxypyrrolidone-2,4-dione^[3] is a colorless oil, soluble in chloroform and methanol.^[4]

In 1991 Tenuazonic acid was reported to inhibit skin tumor promotion in mice ^[5]

References

1. ↑ 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
2. ↑ 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
3. ↑ N. Magan (editor) and M. Olsen (editor): Mycotoxins in Food: Detection and Control. Woodhead Publishing Ltd 2004; ISBN 978-1-85573-733-4, p. 408
4. ↑ J. D. Bewley (edi.), M. Black (edi.) and P. Halmer (edi.): The Encyclopedia of Seeds: Science, Technology and Uses. Cab Intl 2006; ISBN 978-0-85199-723-0; p. 438
5. ↑ Tenuazonic acid page from Fermentek