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23282-20-4,MFCD00133673
Catalog No.:AA00I4GU

23282-20-4 | Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-,(3a,4b,7a)-

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00I4GU
Chemical Name:
Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-,(3a,4b,7a)-
CAS Number:
23282-20-4
Molecular Formula:
C15H20O7
Molecular Weight:
312.3151
MDL Number:
MFCD00133673
SMILES:
OCC12C(C=C(C(=O)C1O)C)OC1C3(C2(C)C(O)C1O)OC3
Properties
Computed Properties
 
Complexity:
588  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
1  
XLogP3:
-1.7  

Literature

Title: Co-exposure to low doses of the food contaminants deoxynivalenol and nivalenol has a synergistic inflammatory effect on intestinal explants.

Journal: Archives of toxicology 20170701

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: Integrated Transcriptional and Proteomic Analysis of Growth Hormone Suppression Mediated by Trichothecene T-2 Toxin in Rat GH3 Cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20151001

Title: Effects of oral exposure to naturally-occurring and synthetic deoxynivalenol congeners on proinflammatory cytokine and chemokine mRNA expression in the mouse.

Journal: Toxicology and applied pharmacology 20140715

Title: Modulation of mucin mRNA (MUC5AC and MUC5B) expression and protein production and secretion in Caco-2/HT29-MTX co-cultures following exposure to individual and combined Fusarium mycotoxins.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20140501

Title: Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20140401

Title: Individual and combined effects of Fusarium toxins on the mRNA expression of pro-inflammatory cytokines in swine jejunal epithelial cells.

Journal: Toxicology letters 20130718

Title: Comparison of emetic potencies of the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20130101

Title: Comprehensive gene expression analysis of type B trichothecenes.

Journal: Journal of agricultural and food chemistry 20120919

Title: Determination of deoxynivalenol and nivalenol by liquid chromatography and fluorimetric detection with on-line chemical post-column derivatization.

Journal: Talanta 20120815

Title: TRI12 based quantitative real-time PCR assays reveal the distribution of trichothecene genotypes of F. graminearum and F. culmorum isolates in Danish small grain cereals.

Journal: International journal of food microbiology 20120716

Title: Development of a PCR assay to detect the potential production of nivalenol in Fusarium poae.

Journal: FEMS microbiology letters 20120701

Title: Comparison of murine anorectic responses to the 8-ketotrichothecenes 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, fusarenon X and nivalenol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120601

Title: Molecular studies to identify the Fusarium species responsible for HT-2 and T-2 mycotoxins in UK oats.

Journal: International journal of food microbiology 20120515

Title: Natural deoxynivalenol occurrence and genotype and chemotype determination of a field population of the Fusarium graminearum complex associated with soybean in Argentina.

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

Title: The effects of mycotoxins and selenium deficiency on tissue-engineered cartilage.

Journal: Cells, tissues, organs 20120101

Title: Mycotoxin contamination of cereal grain commodities in relation to climate in North West Europe.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 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: Interlaboratory study of LC-UV and LC-MS methods for the simultaneous determination of deoxynivalenol and nivalenol in wheat.

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20120101

Title: Genotyping and phenotyping of Fusarium graminearum isolates from Germany related to their mycotoxin biosynthesis.

Journal: International journal of food microbiology 20111115

Title: Pathogenicity, symptom development, and mycotoxin formation in wheat by Fusarium species frequently isolated from sugar beet.

Journal: Phytopathology 20111101

Title: Distinct distribution of deoxynivalenol, nivalenol, and ergosterol in Fusarium-infected Japanese soft red winter wheat milling fractions.

Journal: Mycopathologia 20111001

Title: Verification of the effectiveness of SCAR (sequence characterized amplified region) primers for the identification of Polish strains of Fusarium culmorum and their potential ability to produce B-trichothecenes and zearalenone.

Journal: International journal of food microbiology 20110815

Title: Molecular survey of trichothecene genotypes of Fusarium graminearum species complex from barley in southern Brazil.

Journal: International journal of food microbiology 20110815

Title: Incidence of Fusarium species and mycotoxins in silage maize.

Journal: Toxins 20110801

Title: Occurrence of Fusarium mycotoxins in rice and its milling by-products in Korea.

Journal: Journal of food protection 20110701

Title: Trichothecene genotypes and chemotypes in Fusarium graminearum strains isolated from wheat in Argentina.

Journal: International journal of food microbiology 20110227

Title: Species diversity and toxigenic potential of Fusarium graminearum complex isolates from maize fields in northwest Argentina.

Journal: International journal of food microbiology 20110131

Title: Rapid deposition of glomerular IgA in BALB/c mice by nivalenol and its modifying effect on high IgA strain (HIGA) mice.

Journal: Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20110101

Title: Nivalenol-type populations of Fusarium graminearum and F. asiaticum are prevalent on wheat in southern Louisiana.

Journal: Phytopathology 20110101

Title: [Biosynthesis of 4,15-diacetylnivalenol by Fusarium sambucinum Fuckel var. minus].

Journal: Prikladnaia biokhimiia i mikrobiologiia 20110101

Title: Nuclear factor-κB inhibitors alleviate nivalenol-induced cytotoxicity in HL60 cells.

Journal: Environmental toxicology and pharmacology 20110101

Title: [Dietary exposure assessment of some important Fusarium toxins in cereal-based products in China].

Journal: Wei sheng yan jiu = Journal of hygiene research 20101101

Title: Mechanism-based alternative monitoring of endoplasmic reticulum stress by 8-keto-trichothecene mycotoxins using human intestinal epithelial cell line.

Journal: Toxicology letters 20101020

Title: Distribution of deoxynivalenol and nivalenol in milling fractions from fusarium-infected Japanese wheat cultivars.

Journal: Journal of food protection 20101001

Title: Deoxynivalenol and nivalenol accumulation in wheat infected with Fusarium graminearum during grain development.

Journal: Phytopathology 20100801

Title: Rapid detection of nivalenol and deoxynivalenol in wheat using surface plasmon resonance immunoassay.

Journal: Analytica chimica acta 20100719

Title: A rapid method with ultra-high-performance liquid chromatography-tandem mass spectrometry for simultaneous determination of five type B trichothecenes in traditional Chinese medicines.

Journal: Journal of separation science 20100701

Title: Acidic pH as a determinant of TRI gene expression and trichothecene B biosynthesis in Fusarium graminearum.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20100501

Title: [Effect of Nivalenol and selenium on IL-1beta and TNF-alpha secretion in cultured chondrocytes].

Journal: Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology 20100401

Title: Trichothecene mycotoxins associated with potato dry rot caused by Fusarium graminearum.

Journal: Phytopathology 20100301

Title: Development and validation of a method based on a QuEChERS procedure and heart-cutting GC-MS for determination of five mycotoxins in cereal products.

Journal: Journal of separation science 20100301

Title: Genetic Fusarium chemotyping as a useful tool for predicting nivalenol contamination in winter wheat.

Journal: International journal of food microbiology 20100227

Title: Deoxynivalenol and nivalenol inhibit lipopolysaccharide-induced nitric oxide production by mouse macrophage cells.

Journal: Toxicology letters 20100201

Title: Trichothecenes NIV and DON modulate the maturation of murine dendritic cells.

Journal: Toxicon : official journal of the International Society on Toxinology 20100101

Title: Determination of nivalenol and deoxynivalenol by liquid chromatography/atmospheric pressure photoionization mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20091001

Title: Pro-apoptotic effects of nivalenol and deoxynivalenol trichothecenes in J774A.1 murine macrophages.

Journal: Toxicology letters 20090825

Title: Fusarium mycotoxin content of UK organic and conventional oats.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20090701

Title: Quantification of Fusarium poae DNA and associated mycotoxins in asymptomatically contaminated wheat.

Journal: International journal of food microbiology 20090415

Title: Epithelial cell survival by activating transcription factor 3 (ATF3) in response to chemical ribosome-inactivating stress.

Journal: Biochemical pharmacology 20090315

Title: Occurrence of Fusarium mycotoxins in maize imported into the UK, 2004-2007.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20090301

Title: Immune effects of four Fusarium-toxins (FB1, ZEA, NIV, DON) on the proliferation of Jurkat cells and porcine lymphocytes: in vitro study.

Journal: Veterinary research communications 20080901

Title: Nivalenol and the targeting of the female reproductive system as well as haematopoietic and immune systems in rats after 90-day exposure through the diet.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080901

Title: Distribution of trichothecenes, zearalenone, and ergosterol in a fractionated wheat harvest lot.

Journal: Journal of agricultural and food chemistry 20080827

Title: PCR analysis of the Tri13 gene to determine the genetic potential of Fusarium graminearum isolates from Iran to produce nivalenol and deoxynivalenol.

Journal: Mycopathologia 20080801

Title: Fate of fusarenon-X in broilers and ducks.

Journal: Poultry science 20080801

Title: Gibberella ear rot of maize (Zea mays) in Nepal: distribution of the mycotoxins nivalenol and deoxynivalenol in naturally and experimentally infected maize.

Journal: Journal of agricultural and food chemistry 20080709

Title: Effects of four Fusarium toxins (fumonisin B(1), alpha-zearalenol, nivalenol and deoxynivalenol) on porcine whole-blood cellular proliferation.

Journal: Toxicon : official journal of the International Society on Toxinology 20080701

Title: Fusarium populations on Chinese barley show a dramatic gradient in mycotoxin profiles.

Journal: Phytopathology 20080601

Title: Quantum chemical treatment of nivalenol and its tautomers.

Journal: Journal of hazardous materials 20080501

Title: Determination of trichothecenes in cereals and cereal-based products by liquid chromatography-tandem mass spectrometry.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080301

Title: Fate of the fusarium mycotoxins, deoxynivalenol, nivalenol and zearalenone, during extrusion of wholemeal wheat grain.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080301

Title: Mycotoxins in breakfast cereals from the Canadian retail market: a 3-year survey.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20080301

Title: Trichothecenes and mycoflora in wheat harvested in nine locations in Buenos Aires province, Argentina.

Journal: Mycopathologia 20080201

Title: A 90-day subchronic toxicity study of nivalenol, a trichothecene mycotoxin, in F344 rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080101

Title: Immunotoxicity of nivalenol after subchronic dietary exposure to rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080101

Title: Wheat-infecting Fusarium species in Poland--their chemotypes and frequencies revealed by PCR assay.

Journal: Journal of applied genetics 20080101

Title: Changes in fungi and mycotoxins in pearl millet under controlled storage conditions.

Journal: Mycopathologia 20071101

Title: Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay.

Journal: Journal of agricultural and food chemistry 20070808

Title: Determination of the trichothecene mycotoxin chemotypes and associated geographical distribution and phylogenetic species of the Fusarium graminearum clade from China.

Journal: Mycological research 20070801

Title: Determination of molar absorptivity coefficients for major type-B trichothecenes and certification of calibrators for deoxynivalenol and nivalenol.

Journal: Analytical and bioanalytical chemistry 20070701

Title: The activities of mycotoxins derived from Fusarium and related substances in a short-term transformation assay using v-Ha-ras-transfected BALB/3T3 cells (Bhas 42 cells).

Journal: Mutation research 20070615

Title: Transepithelial transport of fusariotoxin nivalenol: mediation of secretion by ABC transporters.

Journal: Toxicology letters 20070515

Title: Genotoxic potential associated with low levels of the Fusarium mycotoxins nivalenol and fusarenon X in a human intestinal cell line.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20070401

Title: The trichothecenes and their biosynthesis.

Journal: Fortschritte der Chemie organischer Naturstoffe = Progress in the chemistry of organic natural products. Progres dans la chimie des substances organiques naturelles 20070101

Title: Effect of subacute oral doses of nivalenol on immune and metabolic defence systems in mice.

Journal: Veterinary research 20070101

Title: Comparison of four C18 columns for the liquid chromatographic determination of deoxynivalenol in naturally contaminated wheat.

Journal: Journal of AOAC International 20070101

Title: Mycotoxins nivalenol and deoxynivalenol differentially modulate cytokine mRNA expression in Jurkat T cells.

Journal: Cytokine 20061001

Title: Differential induction of apoptosis by type A and B trichothecenes in Jurkat T-lymphocytes.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20060901

Title: Production and characterization of a monoclonal antibody that cross-reacts with the mycotoxins nivalenol and 4-deoxynivalenol.

Journal: Food additives and contaminants 20060801

Title: New possibilities of matrix-assisted laser desorption ionization time of flight mass spectrometry to analyze barley malt quality. Highly sensitive detection of mycotoxins.

Journal: Environmental toxicology 20060801

Title: Natural occurrence of mycotoxins in staple cereals from Ethiopia.

Journal: Mycopathologia 20060701

Title: Multiplex PCR assay for the identification of nivalenol, 3- and 15-acetyl-deoxynivalenol chemotypes in Fusarium.

Journal: FEMS microbiology letters 20060601

Title: Individual and combined effects of low oral doses of deoxynivalenol and nivalenol in mice.

Journal: Cellular and molecular biology (Noisy-le-Grand, France) 20051104

Title: Development of a multicomponent method for Fusarium toxins using LC-MS/MS and its application during a survey for the content of T-2 toxin and deoxynivalenol in various feed and food samples.

Journal: Food additives and contaminants 20050801

Title: Estimated dietary exposure to principal food mycotoxins from the first French Total Diet Study.

Journal: Food additives and contaminants 20050701

Title: Structural elucidation and analysis of thermal degradation products of the Fusarium mycotoxin nivalenol.

Journal: Molecular nutrition & food research 20050401

Title: A rapid multiresidual determination of type A and type B trichothecenes in wheat flour by HPLC-ESI-MS.

Journal: Food additives and contaminants 20050301

Title: Development of a generic PCR detection of deoxynivalenol- and nivalenol-chemotypes of Fusarium graminearum.

Journal: FEMS microbiology letters 20050215

Title: Toxicity data relevant for hazard characterization.

Journal: Toxicology letters 20041010

Title: Effects of grain sampling procedures on fusarium mycotoxin assays in wheat grains.

Journal: Journal of agricultural and food chemistry 20041006

Title: Development of early apoptosis and changes in T-cell subsets in mouse thymocyte primary cultures treated with nivalenol.

Journal: Experimental and molecular pathology 20041001

Title: A practical method for measuring deoxynivalenol, nivalenol, and T-2 + HT-2 toxin in foods by an enzyme-linked immunosorbent assay using monoclonal antibodies.

Journal: Bioscience, biotechnology, and biochemistry 20041001

Title: Nivalenol, a main Fusarium toxin in dietary foods from high-risk areas of cancer of esophagus and gastric cardia in China, induced benign and malignant tumors in mice.

Journal: Oncology reports 20040801

Title: Influence of environmental factors on the biosynthesis of type B trichothecenes by isolates of Fusarium spp. from Spanish crops.

Journal: International journal of food microbiology 20040701

Title: Placental and milk transmission of trichothecene mycotoxins, nivalenol and fusarenon-X, in mice.

Journal: Toxicon : official journal of the International Society on Toxinology 20040701

Title: Evaluation of the intestinal absorption of deoxynivalenol and nivalenol by an in vitro gastrointestinal model, and the binding efficacy of activated carbon and other adsorbent materials.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040501

Title: Functional demarcation of the Fusarium core trichothecene gene cluster.

Journal: Fungal genetics and biology : FG & B 20040401

Title: Comparative cytotoxicity of deoxynivalenol, nivalenol, their acetylated derivatives and de-epoxy metabolites.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040401

Title: Natural occurrence of trichothecenes on lodged and water-damaged domestic rice in Japan.

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20040401

Title: Toxicity and apoptosis induced by the mycotoxins nivalenol, deoxynivalenol and fumonisin B1 in a human erythroleukemia cell line.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20040201

Title: Cytotoxicity induced by nivalenol, deoxynivalenol, and fumonisin B1 in the SF-9 insect cell line.

Journal: In vitro cellular & developmental biology. Animal 20040101

Title: Effects of heating procedures on deoxynivalenol, nivalenol and zearalenone levels in naturally contaminated barley and wheat.

Journal: Food additives and contaminants 20031201

Title: Development of early apopotosis and changes in lymphocyte subsets in lymphoid organs of mice orally inoculated with nivalenol.

Journal: Experimental and molecular pathology 20030801

Title: The fates of trichothecene mycotoxins, nivalenol and fusarenon-X, in mice.

Journal: Toxicon : official journal of the International Society on Toxinology 20030601

Title: Lack of de-epoxidation of type B trichothecenes in incubates with human faeces.

Journal: Food additives and contaminants 20030601

Title: Deoxynivalenol and other Fusarium toxins in wheat and rye flours on the Danish market.

Journal: Food additives and contaminants 20030401

Title: Polymorphism of trichothecene biosynthesis genes in deoxynivalenol- and nivalenol-producing Fusarium graminearum isolates.

Journal: Mycological research 20030201

Title: Determination of deoxynivalenol and nivalenol in corn and wheat by liquid chromatography with electrospray mass spectrometry.

Journal: Journal of AOAC International 20030101

Title: Two-dimensional environmental profiles of growth, deoxynivalenol and nivalenol production by Fusarium culmorum on a wheat-based substrate.

Journal: Letters in applied microbiology 20030101

Title: Effects on health and blood plasma parameters of laying hens by pure nivalenol in the diet.

Journal: Journal of animal physiology and animal nutrition 20021201

Title: Transformation of trichothecenes in ileal digesta and faeces from pigs.

Journal: Archiv fur Tierernahrung 20020801

Title: Nivalenol--induced apoptosis in thymus, spleen and Peyer's patches of mice.

Journal: Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20020201

Title: Fusarium toxins in wheat flour collected in an area in southwest Germany.

Journal: International journal of food microbiology 20020130

Title: Stability of the fusarium mycotoxins nivalenol, deoxynivalenol and zearalenone in ground maize under typical cooking environments.

Journal: Food additives and contaminants 20011101

Title: Effect of time, temperature and solvent on the stability of T-2 toxin, HT-2 toxin, deoxynivalenol and nivalenol calibrants.

Journal: Food additives and contaminants 20011101

Title: Trichothecenes, ochratoxin A and zearalenone contamination and fusarium infection in Finnish cereal samples in 1998.

Journal: Food additives and contaminants 20010801

Title: Critical study of and improvements in chromatographic methods for the analysis of type B trichothecenes.

Journal: Journal of chromatography. A 20010518

Title: Fusariotoxins in kernels of winter wheat cultivars field samples collected during 1993 in Poland.

Journal: Die Nahrung 20010201

Title: Chromatographic methods for trichothecenes.

Journal: Methods in molecular biology (Clifton, N.J.) 20010101

Title: Impact of competitive fungi on Trichothecene production by Fusarium graminearum.

Journal: Journal of agricultural and food chemistry 20010101

Title: Production of culmorin compounds and other secondary metabolites by Fusarium culmorum and F. graminearum strains isolated from Norwegian cereals.

Journal: Mycopathologia 20010101

Title: Levels of fungi and mycotoxins in samples of grain and grain dust collected on farms in Eastern Poland.

Journal: Annals of agricultural and environmental medicine : AAEM 20010101

Title: Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells.

Journal: Toxicology 19951215

Title: Bryła M, et al. Natural Occurrence of Nivalenol, Deoxynivalenol, and Deoxynivalenol-3-Glucoside in Polish Winter Wheat. Toxins (Basel). 2018 Feb 13;10(2).

Title: Aupanun S, et al. Individual and combined mycotoxins deoxynivalenol, nivalenol, and fusarenon-X induced apoptosis in lymphoid tissues of mice after oral exposure. Toxicon. 2019 Jul;165:83-94.

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Tags:23282-20-4 Molecular Formula|23282-20-4 MDL|23282-20-4 SMILES|23282-20-4 Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-,(3a,4b,7a)- |Organic_Building_Blocks