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641-38-3,MFCD00133068
Catalog No.:AA00EBIM

641-38-3 | 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00EBIM
Chemical Name:
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE
CAS Number:
641-38-3
Molecular Formula:
C14H10O5
Molecular Weight:
258.2262
MDL Number:
MFCD00133068
SMILES:
Oc1cc(C)c2c(c1)oc(=O)c1c2cc(O)cc1O
NSC Number:
638263
Properties
Properties
 
BP:
586.894°C at 760 mmHg  
MP:
>300℃ (dec.)  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
371  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
XLogP3:
2.9  

Literature

Title: In vitro combinatory effects of the Alternaria mycotoxins alternariol and altertoxin II and potentially involved miRNAs.

Journal: Toxicology letters 20170205

Title: Impact of phase I metabolism on uptake, oxidative stress and genotoxicity of the emerging mycotoxin alternariol and its monomethyl ether in esophageal cells.

Journal: Archives of toxicology 20170101

Title: Dual effectiveness of Alternaria but not Fusarium mycotoxins against human topoisomerase II and bacterial gyrase.

Journal: Archives of toxicology 20170101

Title: Endocrine activity of mycotoxins and mycotoxin mixtures.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20161001

Title: Impact of Alternaria toxins on CYP1A1 expression in different human tumor cells and relevance for genotoxicity.

Journal: Toxicology letters 20160105

Title: The mycotoxin alternariol induces DNA damage and modify macrophage phenotype and inflammatory responses.

Journal: Toxicology letters 20151119

Title: Oxidative DNA damage and disturbance of antioxidant capacity by alternariol in Caco-2 cells.

Journal: Toxicology letters 20150601

Title: Autophagy and senescence, stress responses induced by the DNA-damaging mycotoxin alternariol.

Journal: Toxicology 20141204

Title: An in vitro investigation of endocrine disrupting effects of the mycotoxin alternariol.

Journal: Toxicology and applied pharmacology 20130815

Title: Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether.

Journal: Toxicology letters 20130110

Title: Induced production of mycotoxins in an endophytic fungus from the medicinal plant Datura stramonium L.

Journal: Bioorganic & medicinal chemistry letters 20121015

Title: Alternaria toxins: Altertoxin II is a much stronger mutagen and DNA strand breaking mycotoxin than alternariol and its methyl ether in cultured mammalian cells.

Journal: Toxicology letters 20121002

Title: Minor contribution of alternariol, alternariol monomethyl ether and tenuazonic acid to the genotoxic properties of extracts from Alternaria alternata infested rice.

Journal: Toxicology letters 20121002

Title: Benzopyranones from the endophytic fungus Hyalodendriella sp. Ponipodef12 and their bioactivities.

Journal: Molecules (Basel, Switzerland) 20120925

Title: Quantitation of mycotoxins in food and feed from Burkina Faso and Mozambique using a modern LC-MS/MS multitoxin method.

Journal: Journal of agricultural and food chemistry 20120912

Title: Cell death induced by the Alternaria mycotoxin Alternariol.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20120901

Title: Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp.

Journal: Fitoterapia 20120901

Title: HOG MAP kinase regulation of alternariol biosynthesis in Alternaria alternata is important for substrate colonization.

Journal: International journal of food microbiology 20120716

Title: Alternariol induces DNA polymerase β expression through the PKA-CREB signaling pathway.

Journal: International journal of oncology 20120601

Title: Illuminating the diversity of aromatic polyketide synthases in Aspergillus nidulans.

Journal: Journal of the American Chemical Society 20120516

Title: Alternariol 9-O-methyl ether.

Journal: Acta crystallographica. Section E, Structure reports online 20120501

Title: The Alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome P450 1A1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor.

Journal: Archives of toxicology 20120401

Title: Mouse hepatoma cell lines differing in aryl hydrocarbon receptor-mediated signaling have different activities for glucuronidation.

Journal: Archives of toxicology 20120401

Title: Verrulactones A and B, new inhibitors of Staphylococcus aureus enoyl-ACP reductase produced by Penicillium verruculosum F375.

Journal: Bioorganic & medicinal chemistry letters 20120401

Title: Toxigenic Alternaria species from Argentinean blueberries.

Journal: International journal of food microbiology 20120315

Title: Chemical and molecular characterization of Phomopsis and Cytospora-like endophytes from different host plants in Brazil.

Journal: Fungal biology 20120201

Title: [Enzyme immunoassay of the secondary metabolites of micromycetes as components of lichen substances].

Journal: Prikladnaia biokhimiia i mikrobiologiia 20120101

Title: Influence of pH and carbon to nitrogen ratio on mycotoxin production by Alternaria alternata in submerged cultivation.

Journal: AMB Express 20120101

Title: A Dutch field survey on fungal infection and mycotoxin concentrations in maize.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20120101

Title: Identification of a polyketide synthase required for alternariol (AOH) and alternariol-9-methyl ether (AME) formation in Alternaria alternata.

Journal: PloS one 20120101

Title: Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market.

Journal: Journal of agricultural and food chemistry 20111228

Title: Influence of water activity and temperature on growth and mycotoxin production by Alternaria alternata on irradiated soya beans.

Journal: International journal of food microbiology 20110915

Title: Oxidative metabolism of the mycotoxins alternariol and alternariol-9-methyl ether in precision-cut rat liver slices in vitro.

Journal: Molecular nutrition & food research 20110701

Title: Widespread occurrence of low levels of alternariol in apple and tomato products, as determined by comparative immunochemical assessment using monoclonal and polyclonal antibodies.

Journal: Journal of agricultural and food chemistry 20110622

Title: The influence of different nitrogen and carbon sources on mycotoxin production in Alternaria alternata.

Journal: International journal of food microbiology 20110527

Title: AFLP variability, toxin production, and pathogenicity of Alternaria species from Argentinean tomato fruits and puree.

Journal: International journal of food microbiology 20110227

Title: [Enzyme immunassay of alternariol for the assessment of risk of agricultural products contamination].

Journal: Prikladnaia biokhimiia i mikrobiologiia 20110101

Title: Three bianthraquinone derivatives from the mangrove endophytic fungus Alternaria sp. ZJ9-6B from the South China Sea.

Journal: Marine drugs 20110101

Title: Process development for the elucidation of mycotoxin formation in Alternaria alternata.

Journal: AMB Express 20110101

Title: [Simultaneous determination of four Alternaria toxins in apple juice concentrate by ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry].

Journal: Se pu = Chinese journal of chromatography 20101201

Title: Analysis of multiple mycotoxins in cereals under ambient conditions using direct analysis in real time (DART) ionization coupled to high resolution mass spectrometry.

Journal: Talanta 20101015

Title: Production and migration of mycotoxins in sweet pepper analyzed by Multimycotoxin LC-MS/MS.

Journal: Journal of agricultural and food chemistry 20101013

Title: Degradation of the Alternaria mycotoxins alternariol, alternariol monomethyl ether, and altenuene upon bread baking.

Journal: Journal of agricultural and food chemistry 20100908

Title: Water activity and temperature effects on mycotoxin production by Alternaria alternata on a synthetic tomato medium.

Journal: International journal of food microbiology 20100901

Title: The transcription factor StuA regulates central carbon metabolism, mycotoxin production, and effector gene expression in the wheat pathogen Stagonospora nodorum.

Journal: Eukaryotic cell 20100701

Title: Alternariol.

Journal: Acta crystallographica. Section E, Structure reports online 20100601

Title: Multi-mycotoxin analysis of maize silage by LC-MS/MS.

Journal: Analytical and bioanalytical chemistry 20100501

Title: Light regulation of metabolic pathways in fungi.

Journal: Applied microbiology and biotechnology 20100201

Title: Impact of water activity and temperature on growth and alternariol and alternariol monomethyl ether production of Alternaria alternata isolated from soybean.

Journal: Journal of food protection 20100201

Title: Occurrence of mycotoxins in feed as analyzed by a multi-mycotoxin LC-MS/MS method.

Journal: Journal of agricultural and food chemistry 20100113

Title: Self-reported chemicals exposure, beliefs about disease causation, and risk of breast cancer in the Cape Cod Breast Cancer and Environment Study: a case-control study.

Journal: Environmental health : a global access science source 20100101

Title: Effects of gamma radiation on the growth of Alternaria alternata and on the production of alternariol and alternariol monomethyl ether in sunflower seeds.

Journal: Food microbiology 20091201

Title: Cytotoxic metabolites produced by Alternaria no.28, an endophytic fungus isolated from Ginkgo biloba.

Journal: Natural product communications 20091101

Title: Stable isotope dilution assays of alternariol and alternariol monomethyl ether in beverages.

Journal: Journal of agricultural and food chemistry 20090624

Title: LC-MS/MS multi-analyte method for mycotoxin determination in food supplements.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20090601

Title: The mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro.

Journal: Toxicology letters 20090425

Title: Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform.

Journal: Molecular nutrition & food research 20090401

Title: [Acute cytotoxicity of alternariol on NIH/3T3 cells].

Journal: Wei sheng yan jiu = Journal of hygiene research 20090301

Title: Mycoflora and mycotoxin production in oilseed cakes during farm storage.

Journal: Journal of agricultural and food chemistry 20090225

Title: Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis.

Journal: Rapid communications in mass spectrometry : RCM 20090101

Title: An overview of conventional and emerging analytical methods for the determination of mycotoxins.

Journal: International journal of molecular sciences 20090101

Title: New antitumour fungal metabolites from Alternaria porri.

Journal: Natural product research 20090101

Title: Influence of alternariol (AOH) on regulator proteins of cap-dependent translation in porcine endometrial cells.

Journal: Toxicology letters 20081110

Title: Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense.

Journal: Journal of natural products 20080601

Title: Alternaria toxins in wheat during the 2004 to 2005 Argentinean harvest.

Journal: Journal of food protection 20080601

Title: LC-MS/MS multi-method for mycotoxins after single extraction, with validation data for peanut, pistachio, wheat, maize, cornflakes, raisins and figs.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080401

Title: Mycotoxin production by Alternaria strains isolated from Argentinean wheat.

Journal: International journal of food microbiology 20071101

Title: Analysis of alternariol and alternariol monomethyl ether on flavedo and albedo tissues of tangerines (Citrus reticulata) with symptoms of alternaria brown spot.

Journal: Journal of agricultural and food chemistry 20070627

Title: Novel oxidative in vitro metabolites of the mycotoxins alternariol and alternariol methyl ether.

Journal: Molecular nutrition & food research 20070301

Title: [Putative mycotoxin-producing fungi isolated from alpataco (Prosopis flexuosa) fruits].

Journal: Revista iberoamericana de micologia 20070301

Title: Real-time PCR quantification of the AM-toxin gene and HPLC qualification of toxigenic metabolites from Alternaria species from apples.

Journal: International journal of food microbiology 20060901

Title: Mutagenicity of the mycotoxin alternariol in cultured mammalian cells.

Journal: Toxicology letters 20060714

Title: Further examination of the effects of nitrosylation on Alternaria alternata mycotoxin mutagenicity in vitro.

Journal: Mutation research 20060714

Title: Survey of the mycobiota of Spanish malting barley and evaluation of the mycotoxin producing potential of species of Alternaria, Aspergillus and Fusarium.

Journal: International journal of food microbiology 20060425

Title: Estrogenic and clastogenic potential of the mycotoxin alternariol in cultured mammalian cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060301

Title: Toxigenic fungi isolated from dried vine fruits in Argentina.

Journal: International journal of food microbiology 20050925

Title: Mycoflora and occurrence of alternariol and alternariol monomethyl ether in Brazilian sunflower from sowing to harvest.

Journal: Journal of agricultural and food chemistry 20050713

Title: Total synthesis of alternariol.

Journal: The Journal of organic chemistry 20050415

Title: Toxigenic profile of Alternaria alternata and Alternaria radicina occurring on umbelliferous plants.

Journal: Food additives and contaminants 20050401

Title: Liquid chromatographic determination of Alternaria toxins in carrots.

Journal: Journal of AOAC International 20040101

Title: Liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry of the Alternaria mycotoxins alternariol and alternariol monomethyl ether in fruit juices and beverages.

Journal: Journal of chromatography. A 20030523

Title: 6H-dibenzo[b,d]pyran-6-one derivatives from the cultured lichen mycobionts of Graphis spp. and their biosynthetic origin.

Journal: Phytochemistry 20030101

Title: Survey of Brazilian tomato products for alternariol, alternariol monomethyl ether, tenuazonic acid and cyclopiazonic acid.

Journal: Food additives and contaminants 20010701

Title: Production of alternariol and alternariol methyl ether by Alternaria alternata grown on fruits at various temperatures.

Journal: Journal of food protection 20010401

Title: Production of alternaria mycotoxins by Alternaria alternata isolated from weather-damaged wheat.

Journal: Journal of food protection 20010401

Title: Examination of Alternaria alternata mutagenicity and effects of nitrosylation using the Ames Salmonella test.

Journal: Teratogenesis, carcinogenesis, and mutagenesis 20010101

Title: Analysis of agricultural commodities and foods for Alternaria mycotoxins.

Journal: Journal of AOAC International 20010101

Title: Fliszár-Nyúl E, et al. Interaction of Mycotoxin Alternariol with Serum Albumin. Int J Mol Sci. 2019 May 12;20(9). pii: E2352.

Title: Grover S, et al. The Alternaria alternate Mycotoxin Alternariol Suppresses Lipopolysaccharide-Induced Inflammation. Int J Mol Sci. 2017 Jul 20;18(7). pii: E1577.

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SDS
Tags:641-38-3 Molecular Formula|641-38-3 MDL|641-38-3 SMILES|641-38-3 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE