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T4887

Sigma-Aldrich

T-2 Toxin

from Fusarium sp., powder, ≥98% (HPLC)

Synonym(s):

12,13-Epoxytrichothec-9-ene-3,4,8,15-tetrol-4,15-diacetate-8-isovalerate, 4β,15-Diacetoxy-3α-hydroxy-8α-(3-methylbutyryloxy)-12,13-epoxytrichothec-9-ene

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About This Item

Empirical Formula (Hill Notation):
C24H34O9
CAS Number:
21259-20-1
Molecular Weight:
466.52
Beilstein/REAXYS Number:
3575695
EC Number:
244-297-7
MDL number:
MFCD00871255
UNSPSC Code:
85151701
PubChem Substance ID:
24900234
NACRES:
NA.77

biological source

Fusarium sp.

Quality Level

200

assay

≥98% (HPLC)

form

powder

availability

not available in USA, Japan

color

white

solubility

chloroform: soluble 9.80-10.20 mg/mL, clear, colorless to faintly yellow
DMSO: freely soluble
petroleum ether: slightly soluble

storage temp.

−20°C

SMILES string

[H][C@]12O[C@]3([H])[C@H](O)[C@@H](OC(C)=O)[C@](C)([C@@]1(COC(C)=O)C[C@H](OC(=O)CC(C)C)C(C)=C2)[C@]34CO4

InChI

1S/C24H34O9/c1-12(2)7-18(27)32-16-9-23(10-29-14(4)25)17(8-13(16)3)33-21-19(28)20(31-15(5)26)22(23,6)24(21)11-30-24/h8,12,16-17,19-21,28H,7,9-11H2,1-6H3/t16-,17+,19+,20+,21+,22+,23+,24-/m0/s1

InChI key

BXFOFFBJRFZBQZ-QYWOHJEZSA-N

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Application

T-2 toxin can cause degenerative lesions in articular cartilage of rats8. Furthermore, immunotoxicity studies have reported that T-2 toxin can cause cell death in human lymphoid T cells and also induces cell membrane damage in B cells9.

Biochem/physiol Actions

The trichothecenes, such as T2 Toxin, are mycotoxins produced by fungi of the genus Fusarium. They are commonly present in foods and feed of cereal origin. T-2 toxin induces DNA damage and cell death on prolonged administration. These effects can be partially blocked by antioxidants, such as glutathione, coenzyme Q10, or α-tocopherol. Increases blood-brain barrier permeability and inhibits monoamine oxidase activity in brain.

Quality

Chromatographically purified

Preparation Note

T-2 Toxin is soluble in chloroform at 9.80 - 10.20 mg/ml and yields a clear, colorless to faint yellow solution. Furthermore, the product is freely soluble in DMSO and slightly soluble in petroleum ether.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Skin Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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F Atroshi et al.
Molecular aspects of medicine, 18 Suppl, S255-S258 (1997-01-01)
Active oxygen species are reported to cause organ damage. This study was therefore designed to determine whether oxidative stress contributed to the initiation or progression of hepatic DNA damage produced by T-2 toxin. The aim of the study was also
Paweł Wojtacha et al.
Toxins, 13(4) (2021-05-01)
Plant materials used in the production of pig feed are frequently contaminated with mycotoxins. T-2 toxin is a secondary metabolite of selected Fusarium species, and it can exert a harmful influence on living organisms. Most mycotoxins enter the body via
J Shinozuka et al.
Toxicologic pathology, 26(5), 674-681 (1998-10-28)
We examined T-2 toxin-induced lesions in the bone marrow and splenic red pulp as many as 48 hr after oral inoculation with 10 mg/kg body weight of T-2 toxin in female ICR:CD-1 mice. Histopathologically, the bone marrow and splenic red
Z Islam et al.
Bioscience, biotechnology, and biochemistry, 62(8), 1492-1497 (1998-10-03)
Recently we found that a single administration of T-2 toxin (T-2), a trichothecene mycotoxin, into mice induced DNA fragmentation, a biochemical hallmark of apoptosis, in the thymus. In this study, we investigated the effective chemical structure(s) of T-2-derived metabolites capable
Agnieszka Chlebicz et al.
Probiotics and antimicrobial proteins, 12(1), 289-301 (2019-02-06)
The aim of the following research was to determine the detoxification properties of probiotic Lactobacillus sp. bacteria (12 strains) and S. cerevisiae yeast (6 strains) towards mycotoxins, such as aflatoxin B1, deoxynivalenol, fumonisins, T-2 toxin and zearalenone, which pose as
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