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Merck
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E5286

Enniatin B1

From Gnomonia errabunda, ≥95% (HPLC), Pdr5p inhibitor

Synonym(s):

2-(N-Methyl-L-isoleucine) Enniatin B, 3-Butan-2-yl-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

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About This Item

Empirical Formula (Hill Notation):
C34H59N3O9
CAS Number:
19914-20-6
Molecular Weight:
653.85
MDL number:
MFCD14635386
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (HPLC)
Quality level:
200

Key Documents

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Product Name

Enniatin B1, from Gnomonia errabunda, ≥95% (HPLC)

SMILES string

N1(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C1=O)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C)C(CC)C)C

InChI

1S/C34H59N3O9/c1-16-22(12)25-34(43)46-27(20(8)9)30(39)36(14)23(17(2)3)32(41)44-26(19(6)7)29(38)35(13)24(18(4)5)33(42)45-28(21(10)11)31(40)37(25)15/h17-28H,16H2,1-15H3

InChI key

UQCSETXJXJTMKO-UHFFFAOYSA-N

biological source

Gnomonia errabunda

assay

≥95% (HPLC)

solubility

DMSO: 10 mg/mL
ethanol: 10 mg/mL
methanol: 10 mg/mL

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Enniatin B1 has been used as a mycotoxin in the cell viability assay of primary porcine brain capillary endothelial cells (PBCEC) and human brain microvascular capillary cells (HBMEC). It has also been used as an analytical standard in mass spectrometry measurements.

Biochem/physiol Actions

Enniatins are a group of cyclohexadepsipeptide mycotoxins produced by Gnomonia errabuda and several Fusaria species, with phytotoxic, antibiotic, and insecticidal activities. Enniatins function as ionophors by their incorporation into the cellular membrane to form dimeric structures that transport monovalent ions across the membrane (especially the mitochondrial membranes) affecting oxidative phosphorylation uncoupling. It has been demonstrated that enniatins have a cytotoxic effect on human cancer cells. Furthermore, incubation of H4IIE hepatoma cells with enniatins strongly diminished phosphorylation of the ERK (p44/p42). Enniatins B and B1 inhibit the multi-drug resistance transporter Pdr5p from Saccharomyces cerevisiae, indicating their beneficial potential in cases of drug resistant patients.
Enniatins are cyclohexadepsipeptide mycotoxins that have phytotoxic, antibiotic, and insecticidal activities and function as ionophors.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000436121
0000436121
0000409703
0000409703
0000260175

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Isabel Krug et al.
PloS one, 13(5), e0197406-e0197406 (2018-05-17)
Enniatins are common contaminants of food and feed and belong to the group of the "emerging" mycotoxins, which are produced by various Fusarium species. Although a wide range of toxic effects, like antibacterial, antifungal, insecticidal and cytotoxic properties, have been
Chemical assessment of mycotoxin contaminants and veterinary residues in Costa Rican animal feed
Leiva A, et al.
International Journal of Food Contamination, 6(1), 5-5 (2019)
Terje Svingen et al.
Environmental toxicology, 32(5), 1658-1664 (2016-09-16)
Mycotoxins are fungi-born metabolites that can contaminate foods through mould-infected crops. They are a significant food/feed-safety issue across the globe and represent a substantial financial burden for the world economy. Moreover, with a changing climate and fungal biota, there is

Related Content

Data Sheet - E5286

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