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E5411

Enniatin B

Name: Enniatin B
Brand: SIGMA

From Gnomonia errabunda, ≥95% (HPLC), antibiotic

Synonym(s):

N-Methylcyclo(L-Val-D-Hmb-N-methyl-L-Val-D-Hmb-N-methyl-L-Val-D-Hmb-);(3S,6R,9S,12R,15S,18R)-3,6,9,12,15,18-Hexaisopropyl-4,10,16-trimethyl-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):

C₃₃H₅₇N₃O₉

CAS Number:

917-13-5

Molecular Weight:

639.82

MDL number:

MFCD00236425

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥95% (HPLC)

Quality level:

200

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Product Name

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

biological source

Gnomonia errabunda

Quality Level

200

assay

≥95% (HPLC)

solubility

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

storage temp.

−20°C

SMILES string

N1([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C1=O)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C

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

Related Categories

Bioactive Small Molecules

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

GHS06

signalword

Danger

hcodes

H301 + H311 + H331

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

0000522937

0000453961

0000416831

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Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform.

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

An investigation of the endocrine disrupting potential of enniatin B using in vitro bioassays.

Shewit Kalayou et al.

Toxicology letters, 233(2), 84-94 (2015-01-28)

Evidence that some of the fungal metabolites present in food and feed may act as potential endocrine disruptors is increasing. Enniatin B (ENN B) is among the emerging Fusarium mycotoxins known to contaminate cereals. In this study, the H295R and

Global Trade Item Number

SKU	GTIN
E5411-1MG	04061833604328

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