Chemicals and Drugs

Zearalenone

(S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

(S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.

Chemical Identity

Chemical Information

Molecular Formula
C18H22O5
Molecular Weight
318.4 g/mol
CAS Registry No.
17924-92-4
IUPAC Name
(4S,12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
InChIKey
MBMQEIFVQACCCH-QBODLPLBSA-N
SMILES
C[C@H]1CCCC(=O)CCC/C=C/C2=C(C(=CC(=C2)O)O)C(=O)O1
MeSH Unique ID
D015025
Source
PubChem CID 5281576

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

5 entry terms
  • F-2 Toxin
  • F2 Toxin
  • F 2 Toxin
  • Toxin, F-2
  • Toxin, F2

MeSH Record

Aspects Covered

27 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

a mycotoxin & non-steroidal estrogen; do not confuse with zearalanone (index under ZEARALENONE /analogs)

MeSH Record

History Note

91(75); was see under RESORCINOLS 1975-90

MeSH Record

Previous Indexing

  • Lactones (1966-1974)
  • Resorcinols (1966-1974)

MeSH Hierarchy

Tree Numbers

  1. D02w.455w.426w.559w.389.657w.852w.900w
  2. D02w.540w.950w
  3. D23.946w.587w.989w

AMA Style

References

  1. National Library of Medicine. Zearalenone. Medical Subject Headings (MeSH). 2026. Unique ID D015025. http://id.nlm.nih.gov/mesh/2026/D015025
  2. Zearalenone. In: Wikipedia. https://en.wikipedia.org/wiki/Zearalenone
  3. Zearalenone. In: Wikidata. https://www.wikidata.org/wiki/Q169326
  4. Zearalenone. In: PubChem Compound. CID 5281576. https://pubchem.ncbi.nlm.nih.gov/compound/5281576