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
1. Mycotoxins
Birgit Puschner Vet Clin North Am Small Anim Pract . 2002 Mar;32(2):409-19. doi: 10.1016/s0195-5616(01)00011-0.
The relevance of many mycotoxins to small animal health is difficult to assess, because available information has not been collated and reviewed. Only aflatoxins, penitrem A, and roquefortine have been confirmed in natural mycotoxicoses in pets. Effects of tricothecene mycotoxins, patulin, and penicillic acid on dogs and cats have only been studied experimentally and have not been confirmed in natural outbreaks. Although they make up only a small portion of the cases presented to veterinarians, mycotoxicoses often require special effort. Establishing an accurate diagnosis is crucial to minimize exposure and provide adequate treatment. In most cases, clinical examination, clinical pathologic testing, and analytical chemistry analysis of suspect feed are necessary to reach a diagnosis.
2. Production of penicillic acid by Aspergillus sclerotiorum CGF
S W Kang, C H Park, S I Hong, S W Kim Bioresour Technol . 2007 Jan;98(1):191-7. doi: 10.1016/j.biortech.2005.11.033.
The production of penicillic acid by Aspergillus sclerotiorum CGF for the biocontrol of Phytophthora disease was investigated in submerged fermentation using media composed of different nutrients. Soluble starch was found to be the most effective substrate among the carbon sources used, and produced the highest penicillic acid concentration of 2.98 mg ml(-1). When organic nitrogen sources were used, pharmamedia, yeast extract, and polypeptone-S were found to be suitable organic nitrogen sources (2.46-2.71 mg ml(-1)). The production of penicillic acid was not detected in when inorganic nitrogen sources were used. Only Na2HPO4, among the metal ions and phosphate salts tested, increased the production of penicillic acid (approximately 20%). When A. sclerotiorum CGF was cultured in optimal medium [8.0% (w/v) soluble starch, 0.6% (w/v) yeast extract, and 0.3% (w/v) Na2HPO4], maximum penicillic acid concentration (approximately 9.40 mg ml(-1)) and cell mass (approximately 17.4 g l(-1)) were obtained after 12 days.
3. Penicillic acid in fruits: method development, validation by liquid chromatography-tandem mass spectrometry and survey in southern China
Yingxin You, Yanna Rao, Jiaying Hong, Haiying Wu, Jialing Li, Wenbi Guan J Sci Food Agric . 2021 May;101(7):2779-2787. doi: 10.1002/jsfa.10906.
Background:Penicillic acid (PA) is produced by Aspergillus spp. and Penicillium spp., which are common postharvest and storage fungi of fruits. PA can be of concern for human health because of its toxicity and high fruit consumption by the population. However, no data on PA occurrence in various fruits have yet been reported. A quick, easy, cheap, effective, rugged and safe (QuEChERS) approach for PA determination in various fruits was developed and applied to explore PA incidence in fruits.Results:The modified QuEChERS procedure with extraction by ethyl acetate and purification by multi-walled carbon nanotubes (MWCNTs), primary secondary amine (PSA) and octadecyl silane (C18) was established to determine PA in various fruits by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). The average recoveries were 72.9-102.2% and relative standard deviations (RSDs) were 1.3-7.9%. A total of 161 fruits samples, including kiwi, apple, peach, grape and mandarin/orange, were collected in southern China. The incidence of PA in fruits was 14.9% and the levels of PA contamination were 0.200-0.596 μg kg-1. Our results suggested that orange/mandarin, grape and kiwi were favorable matrices for Aspergillus spp. and Penicillium spp. to produce PA, rather than peach and apple.Conclusion:To the best of our knowledge, this is the first report about PA contamination in various fruits in China. Our study emphasizes the necessity of the current established method, which could be used for continuous monitoring of PA and reducing the health risk to Chinese consumers. © 2020 Society of Chemical Industry.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
