Nivalenol from Fusarium nivale - ≥99%(HPLC) , CAS No.23282-20-4

CAS: 23282-20-4 Cat. No.: N139791 Molecular Weight: 312.3 EC Number: 621-749-5

GRADE & PURITY ≥99%(HPLC)

Synonyms

Trichothec-9-en-8-one,12,13-epoxy-3a,4b,7a,15-tetrahydroxy-(8CI) | 12,13-Epoxy-3a,4b,7a,15-tetrahydroxytrichothec-9-en-8-one | 3a,4b,7a,15-Tetrahydroxyscrip-9-en-8-one | NSC 269143 | Nivalenol | NSC 269143 | 12,13-EPOXY-3.ALPHA.,4.BETA.,7.ALPHA.,15-TETRAH

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Nivalenol is a type - B trichothecene mycotoxin, produced by molds such as Fusarium cerealis, Fusarium graminearum. Nivalenol may be formed by higher plants and by mamals, as a productt of biodegradation of other thrichothecenes.
Nivalenol (0.01 mg/ml) induces apoptosis in HL60 cells (Ueno et al., 1995). Nivalenol was shown to inhibit protein synthesis in rabbit reticulocytes in vitro. Nivalenol inhibited the synthesis of nucleic acids in vitro (Ueno and Fukushima, 1968)

Specifications

Synonyms

Trichothec-9-en-8-one, 12, 13-epoxy-3a, 4b, 7a, 15-tetrahydroxy-(8CI) | 12, 13-Epoxy-3a, 4b, 7a, 15-tetrahydroxytrichothec-9-en-8-one | 3a, 4b, 7a, 15-Tetrahydroxyscrip-9-en-8-one | NSC 269143 | Nivalenol | NSC 269143 | 12, 13-EPOXY-3.ALPHA., 4.BETA., 7.ALPHA., 15-TETRAH

Specifications & Purity

≥99%(HPLC)

Biochemical and Physiological Mechanisms

Trichothecene mycotoxin. Cytotoxic in vitro (EC 50 = 0.96 μM). Decreases cell proliferation. Pro-apoptotic activity. Active in vitro and in vivo .

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.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%(HPLC)

Names and Identifiers

• Canonical Smiles: CC1=CC2C(C(C1=O)O)(C3(C(C(C(C34CO4)O2)O)O)C)CO
• IUPAC Name: (1S,2R,3S,7R,9R,10R,11S,12S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
• InChIKey: UKOTXHQERFPCBU-XBXCNEFVSA-N
• INCHI: 1S/C15H20O7/c1-6-3-7-14(4-16,11(20)8(6)17)13(2)10(19)9(18)12(22-7)15(13)5-21-15/h3,7,9-12,16,18-20H,4-5H2,1-2H3/t7-,9-,10-,11-,12-,13-,14-,15+/m1/s1
• Isomeric SMILES: CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3([C@@H]([C@H]([C@H]([C@@]34CO4)O2)O)O)C)CO
• WGK Germany: 3
• Molecular Weight: 312.3
• Reaxy-Rn: 25496613
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25496613&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 Polyols 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 - Polyol - Organoheterocyclic compound - Organic oxide - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Alcohol - Primary 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(non-human)

Arabidopsis thaliana (307 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Saccharomyces cerevisiae (19171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Dichloromethane, DMSO, Methanol. Slightly soluble in water,
• Sensitivity: Light Sensitive
• Melt Point(°C): 127°C-130°C
• Molecular Weight: 312.310 g/mol
• XLogP3: -1.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 312.121 Da
• Monoisotopic Mass: 312.121 Da
• Topological Polar Surface Area: 120.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 588.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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

References

1. Lakshani Madushika, Yongming Huang, Menghan Sun, Yuxuan Liu, Linfang Lu, Xiaoli Li, Na Li, Kang Jiang, Sumei Ling, Shihua Wang.  (2025)  Development of sensitive and rapid immunoassays for Moniliformin (MON) detection based on nanomaterials labeled monoclonal antibodies.  FOOD CHEMISTRY,      [PMID:39842210] [10.1016/j.foodchem.2025.142911]