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Penicillic Acid

SKU
P-1179
  • CAS:90-65-3
  • Formula:C8H10O4
  • MW:170.16 Da
  • Appearance:White powder
  • Purity:≥98%
Product Name Qty
Penicillic Acid
10 mg
$122.35
Penicillic Acid
50 mg
$285.49
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Description

Penicillic acid is a potential antibiotic. It is carcinogenic and mutagenic by inducing DNA single strand breaks.

Penicillic acid is a mycotoxin isolated from Penicillium cyclopium and has known mutagenic and cytotoxic effects by arresting cell cycle in a metaphase and interrupting DNA synthesis.

It also irreversibly inactivates GMD (GDP-mannose dehydrogenase) which catalyzes GDP-mannuronic acid to alginate.

It has been reported that penicillic acid is a biologically active QSI (Quorum sensing inhibitory) compound and that neutrophils become activated when bacteria are treated with the acid.

 

Applications

• Antibiotics

• Used as an inactivator of GMD (GDP-mannose dehydrogenase)

• Used in quorum sensing studies

 

References

• “Characterization of GDP-mannose Dehydrogenase from the Brown Alga Ectocarpus siliculosus Providing the Precursor for the Alginate Polymer”

• “Inactivation of GDP-mannose dehydrogenase from Pseudomonas aeruginosa by penicillic acid identifies a critical active site loop”

• “Synthesis of the Antibiotic, Penicillic Acid”

• “Mutagenicity and inducibility of DNA single-strand breaks and chromosome aberrations by various mycotoxins"

• “Identity and effects of quorum-sensing inhibitors produced by Penicillium species” 

 

Not for human therapeutic use or for medicinal purposes. For research applications only.

More Information
Alternate Name/Synonyms
3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid; Penicillinsaure; Kyselina penicilova
SKU
P-1179
CAS #
90-65-3
Chemical Name
3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid
Chemical Formula
C8H10O4
Molecular Weight
170.16 Da
Appearance
White powder
Purity
≥98%
Solubility
Soluble in water
Melting Point
83-84°C
Storage Temp
-20°C
USE
Penicillic acid is a mycotoxin isolated from various strains of Penicillium and Aspergillus fungi that demonstrates mutagenic and cytotoxic effects. This compound is demonstrated to induce single-strand DNA breaks and to inhibit DNA synthesis in CHO cells. Penicillic acid is also reported to irreversibly inactivate GMD (GDP-mannose dehydrogenase), interrupting the committed step in alginate biosynthesis. Penicillic acid is an inhibitor of ADH/AKR1A1 and LDH.
Merck Index
Merck Index: 13.7163.2001
MDL NUMBER
MFCD00004365
CHEMACX
X1008780-6
INCHI
InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4+
SMILES
CC(=C)C(=O)/C(=CC(=O)O)/OC
RTECS
MM2625000
UN #'S
UN 3462
PACKING GROUP
II
Handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire protection.
Certificate of Analysis 1
P-1179, J1305.pdf
Certificate of Analysis 2
P-1179_P-1179,_A9083B.pdf
GHS PICTOGRAMS
HandlingAvoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire protection.
UN #'SUN 3462
Packing GroupII
CitationsWell-known quorum sensing inhibitors do not affect bacterial quorum sensing-regulated bean sprout spoilage
Profiling acylated homoserine lactones in Yersinia ruckeri and influence of exogenous acyl homoserine lactones and known quorum-sensing inhibitors on protease production
Mycotoxic nephropathy in Bulgarian pigs and chickens: complex aetiology and similarity to Balkan endemic nephropathy
Complex etiology and pathology of mycotoxic nephropathy in South African pigs
A comparative study of fungi and mycotoxin contamination in animal products from selected rural and urban areas of South Africa with particular reference to the impact of this on health of rural black people
Characterisation of innate T cells in response to oral bacterial infection
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