Alternariol monomethyl ether
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04425 |
| CAS | 26894-49-5 |
| Molecular Weight | 272.25 |
| Molecular Formula | C15H12O5 |
| Purity | >95% |
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Description
The 50 ppm acetonitrile solution of Alternariol monomethyl ether, shows activities as a cholinesterase inhibitor as well as an anti-fungal agent, could be commonly used as a standard solution. It is an alternaria mycotoxin and genotoxin, which can inhibit the activity of DNA-topoisomerases.
Specification
| Related CAS | 23452-05-3 (3,7-dihydroxy-9-methoxy) |
| Synonyms | 6H-Dibenzo[b,d]pyran-6-one, 3,7(3,9 or 7,9)-dihydroxy-9(7 or 3)-methoxy-1-methyl-; 3,7(3,9 or 7,9)-Dihydroxy-9(7 or 3)-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; Alternariol, methyl ether |
| Storage | Store at 2-8°C |
| IUPAC Name | 3,7(3,9 or 7,9)-dihydroxy-9(7 or 3)-methoxy-1-methylbenzo[c]chromen-6-one |
Properties
| Appearance | White to Light Beige Solid |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 559.169°C at 760 mmHg |
| Melting Point | 266-268°C (dec.) |
| Density | 1.427 g/cm3 |
| Solubility | Slightly soluble in DMSO, Methanol (Heated) |
Reference Reading
1. Alternariol monomethyl ether toxicity and genotoxicity in male Sprague-Dawley rats: 28-Day in vivo multi-endpoint assessment
Xinyao Tang, Yiyi Chen, Xia Zhu, Yeqiu Miao, Dongxia Wang, Jing Zhang, Ruirui Li, Lishi Zhang, Jinyao Chen Mutat Res Genet Toxicol Environ Mutagen. 2022 Jan;873:503435. doi: 10.1016/j.mrgentox.2021.503435. Epub 2021 Dec 2.
Alternariol monomethyl ether (AME), a typical Alternaria toxin, has often been detected in grains. We have measured the general toxicity and genotoxicity of AME with a 28-day multi-endpoint (Pig-a assay + in vivo micronucleus [MN] test + comet assay) platform. Male Sprague-Dawley rats were administered AME (1.84, 3.67, or 7.35 μg/kg body weight/day), N-Ethyl-N-nitrosourea (40 mg/kg body weight/day), or corn oil by gavage for 28 consecutive days. Another group (AME-high-dose + recovery) was maintained for a further 14 days after the end of the AME administration. Hematology and serum biochemistry results suggested that AME might compromise the immune system. The histopathology results indicated that AME can cause liver (inflammatory cell infiltration, steatosis, and edema), kidney (renal glomerular atrophy), and spleen (white pulp atrophy) damage. The genotoxicity results showed that AME can induce gene mutations, chromosome breakage, and DNA damage, but the effects were diminished after the recovery period. According to point-of-departure analysis (BMDL10), the risk to the population of exposure to AME cannot be ignored and further assessment is needed.
2. Occurrence and Determination of Alternaria Mycotoxins Alternariol, Alternariol Monomethyl Ether, and Tentoxin in Wheat Grains by QuEChERS Method
Nikola Puvača, Giuseppina Avantaggiato, Jordan Merkuri, Gorica Vuković, Vojislava Bursić, Magdalena Cara Toxins (Basel). 2022 Nov 12;14(11):791. doi: 10.3390/toxins14110791.
The Alternaria mycotoxins such as alternariol (AOH), alternariol monomethyl ether (AME), and tentoxin (TEN) are mycotoxins, which can contaminate cereal-based raw materials. Today, wheat is one of the most important crops in temperate zones, and it is in increasing demand in the Western Balkans countries that are urbanizing and industrializing. This research aimed to investigate the occurrence and determine the concentration of Alternaria mycotoxins AOH, AME, and TEN in wheat samples from the Republic of Serbia and the Republic of Albania, harvested in the year 2020 in the period between 15 June and 15 July. A total of 80 wheat grain samples, 40 from each country, were analyzed by an QuEChERS (quick, easy, cheap, effective, rugged, and safe) method. From the obtained results, it can be seen that the mean concentration of AOH was 3.3 µg/kg and AME was 2.2 µg/kg in wheat samples from Serbia, while TEN from both Serbia and Albania was under the limit of quantification (
3. About Alternaria toxins in cocoa and chocolate products-method development and monitoring of alternariol, alternariol monomethyl ether and tenuazonic acid
Julia Schultz, Kim Marie Umberath, Marion Raters, Frank Heckel Mycotoxin Res. 2022 Aug;38(3):167-173. doi: 10.1007/s12550-022-00457-z. Epub 2022 Apr 18.
A quick and selective analytical method was developed via LC-MS/MS for the simultaneous quantitation of alternariol (AOH), alternariol monomethyl ether (AME) and tenuazonic acid (TeA) which belong to the large group of secondary metabolites produced by fungi of the genus Alternaria. Cocoa is susceptible to a number of toxin-producing microorganisms, including Aspergillus and Penicillium species. The method relies on a single-step extraction, followed by an easy clean up, dilution of the raw extract and direct analysis. To assess whether cocoa and chocolate products can be a source of Alternaria toxins, a monitoring of cocoa and chocolate products (N = 99) as well as cocoa raw and semi-finished materials (cocoa shells, cocoa masses; N = 10) was performed. As the results, cocoa and products made from cocoa (without other ingredients) are no source of the Alternaria toxins considered here.
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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 ╳
