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Category: information only not used for fragrances or flavors
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 827.04 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 849.00 °F. TCC ( 454.00 °C. ) (est)
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| logP (o/w): | 3.048 (est) |
| Soluble in: |
| | water, 0.01675 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | information only not used for fragrances or flavors |
| Recommendation for enniatin usage levels up to: | | | not for fragrance use.
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| Recommendation for enniatin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| European Food Safety Authority (EFSA) reference(s): |
Scientific Opinion on the risks to human and animal health related to the presence of beauvericin and enniatins in food and feed View page or View pdf |
In vivo toxicity and genotoxicity of beauvericin and enniatins. Combined approach to study in vivo toxicity and genotoxicity of mycotoxins beauvericin (BEA) and enniatin B (ENNB) View page or View pdf |
| EPI System: | View |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 3084092 |
| National Institute of Allergy and Infectious Diseases: | Data |
| | (3S,9S,15S)-4,10,16-trimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
| Chemidplus: | 0011113625 |
References:
| | (3S,9S,15S)-4,10,16-trimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 3084092 |
| Pubchem (sid): | 135231468 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (3S,9S,15S)-4,10,16- | trimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
Articles:
| PubMed: | Occurrence of pre- and post-harvest mycotoxins and other secondary metabolites in danish maize silage. |
| PubMed: | Effect of fungal colonization of wheat grains with Fusarium spp. on food choice, weight gain and mortality of meal beetle larvae (Tenebrio molitor). |
| PubMed: | Evaluation of immunologic effect of Enniatin A and quantitative determination in feces, urine and serum on treated Wistar rats. |
| PubMed: | Multiclass analysis of mycotoxins in biscuits by high performance liquid chromatography-tandem mass spectrometry. Comparison of different extraction procedures. |
| PubMed: | Cooccurrence of mycotoxins in maize and poultry feeds from Brazil by liquid chromatography/tandem mass spectrometry. |
| PubMed: | A preliminary study in Wistar rats with enniatin A contaminated feed. |
| PubMed: | Pilot toxicokinetic study and absolute oral bioavailability of the Fusarium mycotoxin enniatin B1 in pigs. |
| PubMed: | Inducing secondary metabolite production by the endophytic fungus Fusarium tricinctum through coculture with Bacillus subtilis. |
| PubMed: | Trascriptional regulation of enniatins production by Fusarium avenaceum. |
| PubMed: | Optimization of enniatin production by solid-phase fermentation of Fusarium tricinctum. |
| PubMed: | Occurrence of Fusarium mycotoxins in Italian cereal and cereal products from organic farming. |
| PubMed: | Effects of beauvericin, enniatin b and moniliformin on human dendritic cells and macrophages: an in vitro study. |
| PubMed: | The emerging mycotoxin, enniatin B1, down-modulates the gastrointestinal toxicity of T-2 toxin in vitro on intestinal epithelial cells and ex vivo on intestinal explants. |
| PubMed: | Quantitative determination of the Fusarium mycotoxins beauvericin, enniatin A, A1, B and B1 in pig plasma using high performance liquid chromatography-tandem mass spectrometry. |
| PubMed: | Sequence divergence of the enniatin synthase gene in relation to production of beauvericin and enniatins in Fusarium species. |
| PubMed: | Development and validation of a (semi-)quantitative UHPLC-MS/MS method for the determination of 191 mycotoxins and other fungal metabolites in almonds, hazelnuts, peanuts and pistachios. |
| PubMed: | Fusarium fungi and associated metabolites presence on grapes from Slovakia. |
| PubMed: | Cytotoxic potency of mycotoxins in cultures of V79 lung fibroblast cells. |
| PubMed: | Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities. |
| PubMed: | Co-exposure of Fusarium mycotoxins: in vitro myelotoxicity assessment on human hematopoietic progenitors. |
| PubMed: | Specific interactions between the Candida albicans ABC transporter Cdr1p ectodomain and a D-octapeptide derivative inhibitor. |
| PubMed: | Biosynthesis of 15N3-labeled enniatins and beauvericin and their application to stable isotope dilution assays. |
| PubMed: | Lysosomes as a possible target of enniatin B-induced toxicity in Caco-2 cells. |
| PubMed: | Enniatin B-induced cell death and inflammatory responses in RAW 267.4 murine macrophages. |
| PubMed: | Stimulatory effect on rat thymocytes proliferation and antimicrobial activity of two 6-(propan-2-yl)-4-methyl-morpholine-2,5-diones. |
| PubMed: | In vitro myelotoxicity assessment of the emerging mycotoxins Beauvericin, Enniatin b and Moniliformin on human hematopoietic progenitors. |
| PubMed: | Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market. |
| PubMed: | Effects of ¹⁴C-labelled precursor feeding on production of beauvericin, enniatins H, I, and MK1688 by Fusarium oxysporum KFCC11363P. |
| PubMed: | Multilocus phylogenetics show high intraspecific variability within Fusarium avenaceum. |
| PubMed: | Stimulation of erythrocyte phospholipid scrambling by enniatin A. |
| PubMed: | Pathogenicity, symptom development, and mycotoxin formation in wheat by Fusarium species frequently isolated from sugar beet. |
| PubMed: | In vitro metabolism of the mycotoxin enniatin B in different species and cytochrome p450 enzyme phenotyping by chemical inhibitors. |
| PubMed: | Multi-mycotoxin analysis in eggs using a QuEChERS-based extraction procedure and ultra-high-pressure liquid chromatography coupled to triple quadrupole mass spectrometry. |
| PubMed: | In vitro phase I metabolism of the depsipeptide enniatin B. |
| PubMed: | Antibacterial activity of the enniatin B, produced by Fusarium tricinctum in liquid culture, and cytotoxic effects on Caco-2 cells. |
| PubMed: | Toxigenicity of enniatins from Western Australian Fusarium species to brine shrimp (Artemia franciscana). |
| PubMed: | Statistical optimization of culture conditions for the production of enniatins H, I, and MK1688 by Fusarium oxysporum KFCC 11363P. |
| PubMed: | Development of TaqMan assays for the quantitative detection of Fusarium avenaceum/Fusarium tricinctum and Fusarium poae esyn1 genotypes from cereal grain. |
| PubMed: | The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis. |
| PubMed: | Antifungal effects of the bioactive compounds enniatins A, A(1), B, B(1). |
| PubMed: | Multi-mycotoxin analysis of maize silage by LC-MS/MS. |
| PubMed: | A two-locus DNA sequence database for typing plant and human pathogens within the Fusarium oxysporum species complex. |
| PubMed: | Structural analysis of enniatin H, I, and MK1688 and beauvericin by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and their production by Fusarium oxysporum KFCC 11363P. |
| PubMed: | Oxidative stress and DNA interactions are not involved in Enniatin- and Beauvericin-mediated apoptosis induction. |
| PubMed: | Identification of Nile red as a fluorescent substrate of the Candida albicans ATP-binding cassette transporters Cdr1p and Cdr2p and the major facilitator superfamily transporter Mdr1p. |
| PubMed: | Interactions between ABC-transport proteins and the secondary Fusarium metabolites enniatin and beauvericin. |
| PubMed: | [Roles of drug efflux pump genes in the mechanism of Saccharomyces albicans biofilm drug tolerance]. |
| PubMed: | The Fusarium toxin enniatin B exerts no genotoxic activity, but pronounced cytotoxicity in vitro. |
| PubMed: | Structural studies on minor enniatins from Fusarium sp. VI 03441: novel N-methyl-threonine containing enniatins. |
| PubMed: | Apoptosis induced by enniatins H and MK1688 isolated from Fusarium oxysporum FB1501. |
| PubMed: | The emerging Fusarium toxin enniatin B: in-vitro studies on its genotoxic potential and cytotoxicity in V79 cells in relation to other mycotoxins. |
| PubMed: | Characterization of the kinetics and mechanisms of inhibition of drugs interacting with the S. cerevisiae multidrug resistance pumps Pdr5p and Snq2p. |
| PubMed: | In vitro synthesis of new cyclodepsipeptides of the PF1022-type: probing the alpha-D-hydroxy acid tolerance of PF1022 synthetase. |
| PubMed: | Enniatins A1, B and B1 from an endophytic strain of Fusarium tricinctum induce apoptotic cell death in H4IIE hepatoma cells accompanied by inhibition of ERK phosphorylation. |
| PubMed: | Development of a LC-MS/MS method for the analysis of enniatins and beauvericin in whole fresh and ensiled maize. |
| PubMed: | Enniatins produced by Fusarium dimerum, an endophytic fungal strain. |
| PubMed: | A bioassay for the simultaneous measurement of metabolic activity, membrane integrity, and lysosomal activity in cell cultures. |
| PubMed: | Diversity in Beauvericin and Enniatins H, I, and MK1688 by Fusarium oxysporum isolated from potato. |
| PubMed: | In vitro synthesis of new enniatins: probing the alpha-D-hydroxy carboxylic acid binding pocket of the multienzyme enniatin synthetase. |
| PubMed: | Synthesis and anthelmintic activity of cyclohexadepsipeptides with cyclohexylmethyl side chains. |
| PubMed: | Functional characterization of the recombinant N-methyltransferase domain from the multienzyme enniatin synthetase. |
| PubMed: | PCR approach based on the esyn1 gene for the detection of potential enniatin-producing Fusarium species. |
| PubMed: | Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells. |
| PubMed: | Synthesis and anthelmintic activity of substituted (R)-phenyllactic acid containing cyclohexadepsipeptides. |
| PubMed: | Genetic variation, real-time PCR, metabolites and mycotoxins ofFusarium avenaceum and related species. |
| PubMed: | Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum. |
| PubMed: | Effects of moniliformin in presence of cyclohexadepsipeptides on isolated mammalian tissue and cells. |
| PubMed: | N-Methyl-4-hydroxy-2-pyridinone analogues from Fusarium oxysporum. |
| PubMed: | Cyclohexadepsipeptides (CHDPs) with improved anthelmintical efficacy against the gastrointestinal nematode (Haemonchus contortus) in sheep. |
| PubMed: | Actions of the antibiotic mycotoxins beauvericin and enniatin on mammalian tissue. |
| PubMed: | A new function of isonitrile as an inhibitor of the Pdr5p multidrug ABC transporter in Saccharomyces cerevisiae. |
| PubMed: | Occurrence of mycotoxin in Farro samples from southern Italy. |
| PubMed: | Enniatin production by the entomopathogenic fungus Verticillium hemipterigenum BCC 1449. |
| PubMed: | Enniatin has a new function as an inhibitor of Pdr5p, one of the ABC transporters in Saccharomyces cerevisiae. |
| PubMed: | Determination of beauvericin and four other enniatins in grain by liquid chromatography-mass spectrometry. |
| PubMed: | Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples. |
| PubMed: | Diversity in metabolite production by Fusarium langsethiae, Fusarium poae, and Fusarium sporotrichioides. |
| PubMed: | Investigation of the electrophysiological properties of enniatins. |
| PubMed: | Synthesis and investigation of a new cyclo (Nalpha-dipicolinoyl) pentapeptide of a breast and CNS cytotoxic activity and an ionophoric specificity. |
| PubMed: | Enniatins of Fusarium sp. strain F31 and their inhibition of Botrytis cinerea spore germination. |
| PubMed: | Cytotoxicity of fungal metabolites to lepidopteran (Spodoptera frugiperda) cell line (SF-9). |
| PubMed: | A new method for in vitro detection of microbially produced mitochondrial toxins. |
| PubMed: | Synthesis and anthelmintic activity of cyclohexadepsipeptides with (S,S,S,R,S,R)-configuration. |
| PubMed: | Application of the empirical force field to macrocyclic ion carriers, siderophores, and biomimetic analogs. |
| PubMed: | Enniatin synthetase is a monomer with extended structure: evidence for an intramolecular reaction mechanism. |
| PubMed: | JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species. |
| PubMed: | Directed biosynthesis of new enniatins. |
| PubMed: | Occurrence of beauvericin and enniatins in wheat affected by Fusarium avenaceum head blight. |
| PubMed: | Simultaneous determination of beauvericin, enniatins, and fusaproliferin by high performance liquid chromatography. |
| PubMed: | Mutational analysis of the N-methyltransferase domain of the multifunctional enzyme enniatin synthetase. |
| PubMed: | [The hypolipidemic action of antibiotic 86/88 (enniatin B) in a hepatoblastoma G2 cell culture]. |
| PubMed: | Biosynthesis of PF1022A and related cyclooctadepsipeptides. |
| PubMed: | Effects of neutral ionophores on membrane electrical characteristics of NG108-15 cells. |
| PubMed: | Biosynthesis of the mycotoxin enniatin inFusarium species. |
| PubMed: | Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat. |
| PubMed: | Effect of disruption of the enniatin synthetase gene on the virulence of Fusarium avenaceum. |
| PubMed: | Enniatin production by fusarium strains and its effect on potato tuber tissue. |
| PubMed: | Alkali cation transport through liposomes by the antimicrobial fusafungine and its constitutive enniatins. |
| PubMed: | Highly conserved N-methyltransferases as an integral part of peptide synthetases. |
| PubMed: | Arrangement of catalytic sites in the multifunctional enzyme enniatin synthetase. |
| PubMed: | Production of type A trichothecenes and enniatin B by Fusarium sambucinum Fuckel sensu lato. |
| PubMed: | Bacterial expression of catalytically active fragments of the multifunctional enzyme enniatin synthetase. |
| PubMed: | Molecular characterization of the enniatin synthetase gene encoding a multifunctional enzyme catalysing N-methyldepsipeptide formation in Fusarium scirpi. |
| PubMed: | Enniatin synthetases from different fusaria exhibiting distinct amino acid specificities. |
| PubMed: | New cyclodepsipeptides, enniatins D, E and F produced by Fusarium sp. FO-1305. |
| PubMed: | A highly specific D-hydroxyisovalerate dehydrogenase from the enniatin producer Fusarium sambucinum. |
| PubMed: | Interaction of cyclic peptides and depsipeptides with calmodulin. |
| PubMed: | Nonribosomal biosynthesis of peptide antibiotics. |
| PubMed: | Cyclosporin synthetase. The most complex peptide synthesizing multienzyme polypeptide so far described. |
| PubMed: | Toxicity and toxin production by Fusarium isolates from New Zealand. |
| PubMed: | Regularly alternating L,D-peptides. III. Hexacyclic peptides from valine or phenylalanine. |
| PubMed: | Constitutive Expression of Enniatin Synthetase during Fermentative Growth of Fusarium scirpi. |
| PubMed: | Enniatins fromFusarium avenaceum isolated from balsam fir foliage and their toxicity to spruce budworm larvae,Choristoneura fumiferana (Clem.) (Lepidoptera: Tortricidae). |
| PubMed: | Synthesis of beauvericin by a multifunctional enzyme. |
| PubMed: | Monoclonal antibodies to the multienzyme enniatin synthetase. Production and use in structural studies. |
| PubMed: | Enniatin B and valinomycin as ion carriers: an empirical force field analysis. |
| PubMed: | Cell-free synthesis of the depsipeptide beauvericin. |
| PubMed: | Mechanism of depsipeptide formation catalyzed by enniatin synthetase. |
| PubMed: | Enniatin synthetase, a novel type of multifunctional enzyme catalyzing depsipeptide synthesis in Fusarium oxysporum. |
| PubMed: | [Structural studies on enniatin B (author's transl)]. |
| PubMed: | A laser-temperature-jump method for the study of the rate of transfer of hydrophobic ions and carriers across the interface of thin lipid membranes. |
| PubMed: | [Studies of nitrogenous metabolite from Fusarium arthrosporioides. I. Extraction and purification of enniatin B and pharmacological activity tests (author's transl)]. |
| PubMed: | Kinetics of L-[14C]leucine transport in Saccharomyces cerevisiae: effect of energy coupling inhibitors. |
| PubMed: | [Biosynthesis of enniatin by washed cells of Fusarium sambucinum]. |
| PubMed: | Alkali ion transport through lipid bilayer membranes mediated by enniatin A and B and beauvericin. |
| PubMed: | Biosynthesis of enniatin B: partial purification and characterization of the synthesizing enzyme and studies of the biosynthesis. |
| PubMed: | [Enniatin B synthesis by a Fusarium sambucinum Fuck culture]. |
| PubMed: | Facilitated transport of di- and trinitrophenolate ions across lipid membranes by valinomycin and nonactin. |
| PubMed: | Biosynthesis of enniatin B. |
| PubMed: | Crystalline conformation of enniatin B. |
| PubMed: | Enniatin production by Fusarium sambucinum: primary, secondary, and unitary metabolism. |
| PubMed: | A comparison of beauvericin, enniatin and valinomycin as calcium transporting agents in liposomes and chromatophores. |
| PubMed: | Natural enniatin A, a mixture of optical isomers containing both erythro- and threo-N-methyl-L-isoleucine residues. |
| PubMed: | The enniatin ionophores. Conformation and ion binding properties. |
| PubMed: | Production of enniatin A. |
| PubMed: | A molecular orbital study on the conformation of enniatin B. |
| PubMed: | Cyclodepsipeptides as chemical tools for studying ionic transport through membranes. |
| PubMed: | The physicochemical basis of the functioning of biological membranes: dynamic conformational properties of enniatin B and its K+ complex in solution. |
| PubMed: | Structure of the K+ complex with enniatin B, a macrocyclic antibiotic with K+ transport properties. |
| PubMed: | The action of certain antibiotics on mitochondrial, erythrocyte and artificial phospholipid membranes. The role of induced proton permeability. |
| PubMed: | Thiourea and potassium permeability of phospholipid bilayer membranes as affected by enniatin B. |
| PubMed: | Topochemical approach in studies of the structure-activity relation: enantio-enniatin B. |
| PubMed: | [Not Available]. |
| PubMed: | [Not Available]. |
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