Zeranol

Names

[ Name ]:
Zeranol

[Synonym ]:
EINECS 247-769-0
1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-, (3S,7R)-
6-(6,10-Dihydroxyundecyl)-β-resorcylic Acid μ-Lactone
(3S,7R)-3,4,5,6,7,8,9
a-Zearalanol
Zeranol
Ralgro
(3S,7R)-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one
(3S,7R)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
α-zearalanol
MFCD00083519
Ralone
Zearalanol
Ralabol
Zearanol

Biological Activity

[Description]:

Zeranol, a metabolite of the mycoestrogen zearalenone, is an estrogen receptor agonist. Zeranol is used as a growth promoter of livestock due to its strong estrogenic activity[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Endocrinology

[In Vitro]

Zeranol exerts dose-dependent biphasic effects on ER-positive human breast carcinoma cells, accelerating cell growth at low concentrations and inducing apoptosis at high concentrations[2].

[References]

[1]. Kennedy DG, et al. Zeranol is formed from Fusarium spp. toxins in cattle in vivo. Food Addit Contam. 1998 May-Jun;15(4):393-400.

[2]. Yuri T, et al. Biphasic effects of zeranol on the growth of estrogen receptor-positive human breast carcinoma cells. Oncol Rep. 2006 Dec;16(6):1307-12.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
576.0±50.0 °C at 760 mmHg

[ Melting Point ]:
178 - 185ºC

[ Molecular Formula ]:
C₁₈H₂₆O₅

[ Molecular Weight ]:
322.396

[ Flash Point ]:
207.9±23.6 °C

[ Exact Mass ]:
322.178009

[ PSA ]:
86.99000

[ LogP ]:
3.86

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DM2520000

CHEMICAL NAME :: 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3 - methyl-, (3S,7X)-

CAS REGISTRY NUMBER :: 26538-44-3

LAST UPDATED :: 199712

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C18-H26-O5

MOLECULAR WEIGHT :: 322.44

WISWESSER LINE NOTATION :: T6-14- GVO&TJ CQ EQ I1 MQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 52 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 52 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 52 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 52 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 7 mg/kg

SEX/DURATION :: female 10-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2100 ug/kg

SEX/DURATION :: female 10-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 300 mg/kg

SEX/DURATION :: female 9-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - sex ratio

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 300 ug/kg

SEX/DURATION :: female 9-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - delayed effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 4-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

DOSE :: 72 ug/kg

SEX/DURATION :: male 26 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

DOSE :: 72 ug/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 750 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 261,181,1991

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302-H312-H319-H332

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R60;R36/37/38

[ Safety Phrases ]:
S53-S36/37/39-S45

[ RIDADR ]:
UN 1648 3 / PGII

[ WGK Germany ]:
3

[ RTECS ]:
DM2520000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Simultaneous determination of six resorcylic acid lactones in feed using liquid chromatography-tandem mass spectrometry and multi-walled carbon nanotubes as a dispersive solid phase extraction sorbent.

J. Chromatogr. A. 1307 , 41-8, (2013)

A simple and cost-effective pre-treatment procedure was developed for six resorcylic acid lactones (RALs) in feed using dispersive solid phase extraction (dSPE) with multi-walled carbon nanotubes (MWC...

Effect of zeranol on expression of apoptotic and cell cycle proteins in murine placentae.

Toxicology 314(1) , 148-54, (2013)

Mycotoxins are chemicals produced by fungus and many of them are toxic to humans. Zeranol is a mycotoxin used to promote growth in cattle in North America; yet such a practice draws concern about the ...

Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships.

J. Nat. Prod. 74 , 1126-31, (2011)

As part of our ongoing investigation of filamentous fungi for anticancer leads, an active fungal extract was identified from the Mycosynthetix library (MSX 63935; related to Phoma sp.). The initial ex...