Enniatin B

Enniatin B

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It is produced by the strain of Fusarium orthoceras var. enniatinum. It has insecticidal and antifungal activity.

Enniatin B

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BBF-01786 1 mg $469 In stock
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Catalog Number BBF-01786
CAS 917-13-5
Description It is produced by the strain of Fusarium orthoceras var. enniatinum. It has insecticidal and antifungal activity.
Molecular Formula C33H57N3O9
Molecular Weight 639.82
Antibiotic Activity Spectrum Fungi
Synonyms 3-N-Methylvaline Enniatin; Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl]; Cyclo(3-methyl-D-2-hydroxybutanoyl-N-methyl-L-valyl-3-methyl-D-2-hydroxybutanoyl-N-methyl-L-valyl-3-methyl-D-2-hydroxybutanoyl-N-methyl-L-valyl)
IUPAC Name (3S,6R,9S,12R,15S,18R)-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
Canonical SMILES CC(C)C1C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
InChI InChI=1S/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3/t22-,23-,24-,25+,26+,27+/m0/s1
InChI Key MIZMDSVSLSIMSC-VYLWARHZSA-N
Boiling Point 827.0±65.0 °C (Predicted)
Melting Point 173-175 °C
Purity >99% by HPLC
Density 1.036±0.06 g/cm3 (Predicted)
Solubility Soluble in Chloroform, Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water
Appearance White powder
Storage -20 °C
1.Mouse tissue distribution and persistence of the food-born fusariotoxins Enniatin B and Beauvericin.
Rodríguez-Carrasco Y1, Heilos D2, Richter L3, Süssmuth RD3, Heffeter P4, Sulyok M5, Kenner L6, Berger W7, Dornetshuber-Fleiss R8. Toxicol Lett. 2016 Apr 15;247:35-44. doi: 10.1016/j.toxlet.2016.02.008. Epub 2016 Feb 15.
The fusariotoxins Enniatin B (Enn B) and Beauvericin (Bea) have recently aroused interest as food contaminants and as potential anticancer drugs. However, limited data are available about their toxic profile. Aim of this study was to investigate their pharmacological behavior in vivo and their persistence in mice. Therefore, liquid chromatography tandem mass spectrometry (LC-MS/MS) was used to analyze the distribution of Enn B and Bea in selected tissue samples and biological fluids originating from mice treated intraperitoneally with these cyclohexadepsipeptides. Overall, no toxicological signs during life time or pathological changes were observed. Moreover, both fusariotoxins were found in all tissues and serum but not in urine. Highest amounts were measured in liver and fat demonstrating the moleculeś tendency to bioaccumulate in lipophilic tissues. While for Bea no metabolites could be detected, for Enn B three phase I metabolites (dioxygenated-Enn B, mono- and di-demethylated-Enn B) were found in liver and colon, with dioxygenated-Enn B being most prominent.

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