Penicillic acid
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Category | Antibiotics |
Catalog number | BBF-02673 |
CAS | 90-65-3 |
Molecular Weight | 170.16 |
Molecular Formula | C8H10O4 |
Purity | 98% |
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Description
It is produced by the strain of Pen. puberulum. It is an antibiotic with activity against gram-positive bacteria, negative bacteria and mycobacterium. It is also used as a raw material for various semisynthetic penicillins. Penicillic acid, a kind of polyketide mycotoxin, has been found to restrain GDP-mannose dehydrogenase and sorts of other dehydrogenases. It causes DNA to break.
Specification
Related CAS | 74667-52-0 (sodium salt) |
Synonyms | 3-Methoxy-5-methyl-4-oxohexa-2,5-dienoic acid; Penicillinsaure; NSC 402844; γ-Keto-β-methoxy-δ-methylene-Δα-hexenoic Acid; HSDB 3523 |
Storage | Store at -20°C |
IUPAC Name | (2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid |
Canonical SMILES | CC(=C)C(=O)C(=CC(=O)O)OC |
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- |
InChI Key | VOUGEZYPVGAPBB-XQRVVYSFSA-N |
Source | Penicillic acid is a mycotoxin produced by several species of Aspergillus and Penicillium. It can be found on contaminated crops such as corn. |
Properties
Appearance | Crystal |
Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycobacteria |
Boiling Point | 285.7±35.0°C at 760 mmHg |
Melting Point | 85-86°C |
Density | 1.157 g/cm3 |
Solubility | Soluble in Chloroform, Water, Ethanol, Dichloromethane |
Toxicity
Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
Mechanism Of Toxicity | Penicillic acid has been shown to inhibit alcohol and lactate dehydrogenases by forming covalent adducts with either cysteine or lysine residues at the enzyme active sites. Penicillic acid also binds directly to the active center cysteine in the large subunit of caspase-8, thus inhibiting FasL-induced apoptosis by targeting self-processing of caspase-8. Penicillic acid is also mutagenic and can cause DNA single-strand breaks, chromosome aberrations, and inhibition of DNA synthesis. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. |
Toxicity | LD50: 600 mg/kg (Oral, Mouse); LD50: 250 mg/kg (Intravenous, Mouse); LD50: 90 mg/kg (Intraperitoneal, Mouse). |
Reference Reading
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2