Deoxynivalenol - ≥98% , CAS No.51481-10-8

CAS: 51481-10-8 Cat. No.: B135944 Formula: C₁₅H₂₀O₆ Molecular Weight: 296.32 EC Number: 610-668-0

GRADE & PURITY ≥98%

Synonyms

(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0?,?]dodecan]-5'-en-4'-one | AS-75858 | Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3-alpha,7-alpha)- | Vomitoxin | 3J6 |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Deoxynivalenol is a mycotoxin usually produced by Fusarium species and is often detected in grains. This compound demonstrates immunosuppressive characteristics at high concentrations and immunostimulatory effects at low concentrations. Other effects of this mycotoxin include down-regulation of genes involved in protein synthesis, proliferation, ribosomal proteins, and mitochondria. Further studies show that Deoxynivalenol is an inducer of calcium release from the endoplasmic reticulum.
A Fusarium mycotoxin.The main toxic effect of Deoxynivalenol is inhibition of protein synthesis via binding to the ribosome.In agricultural R&D, it is widely used to select crops strains with increased resistance against Fusarium.

Application：

Deoxynivalenol has been used:
as a mycotoxin to induce cytotoxicity in porcine jejunal epithelial cells and study the protective effects of Saccharomyces cerevisiae on the cell viability of host cells.
to induce toxicity in nude mice to study the effect of probiotics (Lactobacillus rhamnosus GG (LGG) or Lactobacillus acidophilus (LA)) supplementation on host protection.
as a thyroid hormone receptor (TRβ) antagonist in cell-based luciferase reporter gene (CALUX) assay.

Specifications

Synonyms

(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0?,?]dodecan]-5'-en-4'-one | AS-75858 | Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3-alpha,7-alpha)- | Vomitoxin | 3J6 |

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Deoxynivalenol (DON) blocks the synthesis of DNA and RNA by inhibiting the process of translation.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

Pubchem Sid

508816304

Canonical Smiles

CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)CO

IUPAC Name

(1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one

InChIKey

LINOMUASTDIRTM-QGRHZQQGSA-N

INCHI

1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/m1/s1

Isomeric SMILES

CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3(C[C@H]([C@H]([C@@]34CO4)O2)O)C)CO

WGK Germany

3

RTECS

YD0167000

Molecular Weight

296.32

Reaxy-Rn

36544681

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=36544681&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Trichothecenes
• Alternative Parents: Oxepanes Cyclohexenones Oxanes Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Epoxides Dialkyl ethers Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Trichothecene skeleton - Cyclohexenone - Oxepane - Oxane - Cyclic alcohol - Ketone - Secondary alcohol - Cyclic ketone - Dialkyl ether - Oxirane - Ether - Oxacycle - Organoheterocyclic compound - Organic oxide - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Primary alcohol - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

K562 (73714 Activities)

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Associated Targets(non-human)

Bipolaris oryzae (287 Activities)

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Arabidopsis thaliana (307 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Mus musculus (284745 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in methanol, chloroform, water (slightly), ethanol (9.8 - 10.2 mg/ml), and DMSO.
• Sensitivity: Moisture sensitive
• Molecular Weight: 296.310 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 296.126 Da
• Monoisotopic Mass: 296.126 Da
• Topological Polar Surface Area: 99.500 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 558.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1