Zeranol

Modify Date: 2024-01-02 18:47:05

Zeranol Structure
Zeranol structure
 Common Name Zeranol
CAS Number 26538-44-3 Molecular Weight 322.396
Density 1.2±0.1 g/cm3 Boiling Point 576.0±50.0 °C at 760 mmHg
Molecular Formula C18H26O5 Melting Point 178 - 185ºC
MSDS Chinese USA Flash Point 207.9±23.6 °C
Symbol GHS02 GHS07
GHS02, GHS07		 Signal Word Danger

 Use of Zeranol


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].

 Names

Name (7R,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one
Synonym More Synonyms

 Zeranol 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
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

 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
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

Zearalenone structure

Zearalenone

CAS#:17924-92-4

~45%

Zeranol Structure

Zeranol

CAS#:26538-44-3
Literature: INTERVET INTERNATIONAL B.V.; BETHELL, John, Richard; REID, Gary, Robert; AFFLECK, Krista, Marie; BREINING, Tibor Patent: WO2010/115478 A1, 2010 ; Location in patent: Page/Page column 22 ;
(3S,7R)-14,16-di-O-benzyl-3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one structure

(3S,7R)-14,16-d...

CAS#:106315-76-8

~83%

Zeranol Structure

Zeranol

CAS#:26538-44-3
Literature: Snatzke; Angeli; Decorte; et al. Helvetica Chimica Acta, 1986 , vol. 69, # 3 p. 734 - 748
2-[10(S)-Hydroxy-6-oxo-trans-1-undecenyl]-4,6-bis(benzyloxy)benzoic Acid μ-Lacton structure

2-[10(S)-Hydrox...

CAS#:34297-69-3

~%

Zeranol Structure

Zeranol

CAS#:26538-44-3
Literature: Snatzke; Angeli; Decorte; et al. Helvetica Chimica Acta, 1986 , vol. 69, # 3 p. 734 - 748
(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one structure

(3S,7R)-7,14,16...

CAS#:325142-22-1

~%

b-Zearalanol structure

b-Zearalanol

CAS#:42422-68-4
Zeranol Structure

Zeranol

CAS#:26538-44-3
Literature: Gelo, Mirjana; Sunjic, Vitomir Tetrahedron, 1992 , vol. 48, # 31 p. 6511 - 6520
(3S)-14,16-dihydroxy-3-methyl-1-oxo-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-7-yl acetate structure

(3S)-14,16-dihy...

CAS#:37786-44-0

~%

b-Zearalanol structure

b-Zearalanol

CAS#:42422-68-4
Zeranol Structure

Zeranol

CAS#:26538-44-3
Literature: Gelo, Mirjana; Sunjic, Vitomir Tetrahedron, 1992 , vol. 48, # 31 p. 6511 - 6520
α-Zearalenol structure

α-Zearalenol

CAS#:36455-72-8

~%

Zeranol Structure

Zeranol

CAS#:26538-44-3
Literature: Hellwig, Veronika; Mayer-Bartschmid, Anke; Mueller, Hartwig; Greif, Gisela; Kleymann, Gerald; Zitzmann, Werner; Tichy, Hans-Volker; Stadler, Marc Journal of Natural Products, 2003 , vol. 66, # 6 p. 829 - 837

 Articles33

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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...

 Synonyms

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
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Related Compounds: More...
Zeranol
55331-29-8
zeranol
325142-22-1
|A-Zeranol
42422-68-4
Chemsrc provides Zeranol(CAS#:26538-44-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Zeranol are included as well.>> amp version: Zeranol

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