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860328

Sigma-Aldrich

Penicillic acid

Synonym(s):

3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid, PA

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About This Item

Empirical Formula (Hill Notation):
C8H10O4
CAS Number:
Molecular Weight:
170.16
EC Number:
MDL number:
UNSPSC Code:
12352103
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SMILES string

CO\C(=C/C(O)=O)C(=O)C(C)=C

InChI

1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4-

InChI key

VOUGEZYPVGAPBB-XQRVVYSFSA-N

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Biochem/physiol Actions

Penicillic acid is a polyketide mycotoxin produced by several species of Aspergillus and Penicillium species. It induces single and double strand DNA breaks. Penicillic acid irreversibly inhibits GDP-mannose dehydrogenase (DMG), an alginate synthesis enzyme. It also inhibits muscle aldose dehydrogenase, alcohol dehydrogenase, and lactate dehydrogenase.
Penicillic acid is a polyketide mycotoxin that can induces single and double strand DNA breaks. Inhibits several dehydrogenases including LDH and ADH.

Warning

Carcinogenic mycotoxin.

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S D Stoev et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 27(1), 72-88 (2009-09-16)
Spontaneous nephropathy in Bulgaria, which is observed frequently during meat inspection and which differs morphologically from the classical description of mycotoxic porcine/chicken nephropathy as made in Denmark, was found to have a multi-mycotoxic aetiology being mainly provoked by a combined
Tasso G C Montenegro et al.
Chemistry & biodiversity, 9(10), 2203-2209 (2012-10-20)
The cytotoxic activity at 50 μg/ml of extracts obtained from eleven fungal strains associated to Eudistoma vannamei, an endemic ascidian from Northeast Brazil, against two cell lines, i.e., the HCT-8 (colon cancer) and the MDA-MB-435 (melanoma) cell lines, was investigated.
Mohmed Moslem et al.
Foodborne pathogens and disease, 7(7), 857-861 (2010-04-07)
Postharvest blue mold decay caused by Penicillium spp. is the most important disease of fresh apple fruit in the world, which extend from the field to the store. Two new Penicillium spp. responsible for apple fruit decay were recovered. The
Thomas Bovbjerg Rasmussen et al.
Microbiology (Reading, England), 151(Pt 5), 1325-1340 (2005-05-05)
Quorum sensing (QS) communication systems are thought to afford bacteria with a mechanism to strategically cause disease. One example is Pseudomonas aeruginosa, which infects immunocompromised individuals such as cystic fibrosis patients. The authors have previously documented that blockage of the
S D Stoev et al.
Veterinary research communications, 28(8), 727-746 (2004-12-22)
The combined toxic effect of ochratoxin A (OTA) and penicillic acid (PA) on the body mass, the weight and pathomorphology of some internal organs was studied in 85 broiler chickens fed a mouldy diet containing 130, 300 or 800 ppb

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