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E9661

Sigma-Aldrich

Enniatin A

from Gnomonia errabunda, ≥95% (HPLC)

Synonyme(s) :

Cyclo[(2R)- 2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl- N-methyl-L- isoleucyl]

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About This Item

Formule empirique (notation de Hill):
C36H63N3O9
Numéro CAS:
2503-13-1
Poids moléculaire :
681.90
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Source biologique

Gnomonia errabunda

Niveau de qualité

200

Pureté

≥95% (HPLC)

Solubilité

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

Température de stockage

−20°C

InChI

1S/C36H63N3O9/c1-16-22(10)25-34(43)46-29(20(6)7)32(41)38(14)27(24(12)18-3)36(45)48-30(21(8)9)33(42)39(15)26(23(11)17-2)35(44)47-28(19(4)5)31(40)37(25)13/h19-30H,16-18H2,1-15H3/t22-,23-,24-,25-,26-,27-,28+,29+,30+/m0/s1

Clé InChI

TWHBYJSVDCWICV-BHZTXFQCSA-N

Application

Enniatin A may be used as a mycotoxin reference standard in ultra-performance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS) and liquid chromatography with tandem mass spectrometry (LC-MS-MS)

Actions biochimiques/physiologiques

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).

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301 + H311 + H331

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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No transfer of the non-regulated mycotoxins, beauvericin and enniatins, from feeds to farmed fish reared on plant-based diets
Nacher-Mestre J, et al.
Food Chemistry, 126773-126773 (2020)
Sevcan Mamur et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 35(8), 1633-1644 (2018-06-12)
Enniatin A (EN-A) is a Fusarium mycotoxin which is a common contaminant in grains and especially in maize and it causes serious loss of product. The aim of this study was to investigate the cytotoxic effects using 3-(4,5-dimethylthiazolyl-2)-2,5 diphenyltetrazolium bromide
Multi-mycotoxin contamination of couscous semolina commercialized in Morocco
Zinedine A, et al.
Food Chemistry, 214, 440-446 (2017)
Development and validation of ultra-high-performance liquid chromatography-tandem mass spectrometry methods for the simultaneous determination of beauvericin, enniatins (A, A1, B, B1) and cereulide in maize, wheat, pasta and rice
Decleer M, et al.
Journal of Chromatography A, 1472, 35-43 (2016)
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

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