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Beauvericin

SIGMA/B7510 - ≥97% (HPLC)

Synonym: cyclo(D-α-Hydroxyisovaleryl-L-N-methyl-Phe)3

CAS Number: 26048-05-5
Empirical Formula (Hill Notation): C45H57N3O9
Molecular Weight: 783.95
MDL Number: MFCD00056846
Linear Formula: C45H57N3O9
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-B7510-5MG 5 mg
 $248.00
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assay ≥97% (HPLC)
color white to off-white
form powder or crystals
InChI 1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3
InChI key GYSCAQFHASJXRS-UHFFFAOYSA-N
Quality Level 200 
SMILES string CC(C)C1OC(=O)C(Cc2ccccc2)N(C)C(=O)C(OC(=O)C(Cc3ccccc3)N(C)C(=O)C(OC(=O)C(Cc4ccccc4)N(C)C1=O)C(C)C)C(C)C
storage temp. 2-8°C
technique(s) HPLC: suitable
Application: Beauvericin has been used as an antimicrobial bioactive compound to test its effect on engineered Saccharomyces cerevisiae strains. It has also been used as a mycotoxin standard in the reverse-phase (RP) high-pressure liquid chromatography (HPLC) to quantify mycotoxins produced by Fusarium oxysporum isolates.
Biochem/physiol Actions: Beauvericin (BEA) is a commercial entomopathogenic mycoinsecticide with antiviral, antibacterial, insecticidal, and cytotoxic properties. It elicits apoptotic and nematicidal activities as well. Beauvericin blocks multidrug efflux and Tor complex 1 (TORC1) kinase. It possesses ionophoric functionality and favors channel formation in patches of ventricular myocytes and synthetic membranes. It is shown to inhibit L-type voltage-dependent Ca2+ current in the neuroblastoma cells.
Biochem/physiol Actions: Beauvericin (BEA), a cyclohexadepsipeptide produced by the fungus Beauveria bassiana (Bals.), has antiviral, antibacterial, nematicidal, insecticidal, cytotoxic, and apoptotic activity.
General description: Beauvericin is a cyclohexadepsipeptide from the fungus Beauveria bassiana that belongs to the enniatin antibiotic family. It comprises three D-hydroxyisovaleryl and N-methylphenylalanyl residues each.
Packaging: Bottomless glass bottle. Contents are inside inserted fused cone.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥97% (HPLC)
Storage Temp. 2-8°C
UNSPSC 12352209

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