Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Zearalenone
RN: 17924-92-4
UNII: 5W827M159J
InChIKey: MBMQEIFVQACCCH-QBODLPLBSA-N

Note

  • (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.

Molecular Formula

  • C18-H22-O5

Molecular Weight

  • 318.3668
 

Classification Codes

Classification Codes

  • Drug / Therapeutic Agent
  • Estrogens
  • Estrogens, Non-Steroidal
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Mutation Data
  • Natural Product
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Zearalenone

MeSH Heading

  • Zearalenone

Synonyms

  • (-)-Zearalenone
  • (10S)-Zearalenone
  • (S)-(-)-Zearalenone
  • (S)-Zearalenone
  • 6-(10-Hydroxy-6-oxo-trans-1-undecenyl)-beta-resorcylic acid lactone
  • Benzoxacyclotetradec-11-en-1-one, 14,16-dihydroxy-3-methyl-7-oxo-, trans-
  • BRN 1350216
  • CCRIS 623
  • Compound F-2
  • EINECS 241-864-0
  • F-2 toxin
  • FES
  • HSDB 4208
  • Mycotoxin F2
  • NCI-C50226
  • Resorcylic acid, 6-(10-hydroxy-6-oxo-1-undecenyl)-, mu-lactone, trans-
  • Toxin F2
  • trans-Zearalenone
  • UNII-5W827M159J
  • Zearalenone
  • Zenone

Systematic Names

  • (S-(E))-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
  • 1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-, (3S,11E)-
  • 1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-, (S)-(-)-
  • Zearalenone

Superlist Name

  • Zearalenone

Registry Numbers

CAS Registry Number

  • 17924-92-4

FDA UNII

  • 5W827M159J

Other Registry Number

  • 18695-28-8

System Generated Number

  • 0017924924

Structure Descriptors

InChI

1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1

InChIKey

MBMQEIFVQACCCH-QBODLPLBSA-N

Smiles

c12c(cc(cc2O)O)C=CCCCC(=O)CCC[C@@H](OC1=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LD50 oral > 5mg/kg (5mg/kg)   Veterinary and Human Toxicology. Vol. 25, Pg. 335, 1983.
mouse LD oral > 2gm/kg (2000mg/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-235, Pg. 1982,
mouse LD50 intraperitoneal 5mg/kg (5mg/kg)   Veterinary and Human Toxicology. Vol. 25, Pg. 335, 1983.
rat LD50 oral > 16gm/kg (16000mg/kg)   Toxicology and Applied Pharmacology. Vol. 37, Pg. 144, 1976.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 164.5 deg C   EXP
log P (octanol-water) 3.580 (none)   EST
Atmospheric OH Rate Constant 2.74E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.