ChemicalBook--->CAS DataBase List--->17924-92-4

17924-92-4

17924-92-4 Structure

17924-92-4 Structure
IdentificationMore
[Name]

Zearalenone
[CAS]

17924-92-4
[Synonyms]

3,4,5,6,9,10-HEXAHYDRO-14,16-DIHYDROXY-3-METHYL-1H-2-BENZOXACYCLOTETRADECIN-1,7(8H)-DIONE
(E)-(S)-2,4-DIHYDROXY-7-METHYL-7,8,9,10,13,14-HEXAHYDRO-12H-6-OXA-BENZOCYCLOTETRADECENE-5,11-DIONE
MYCOTOXIN F2
ZEARALENONE
ZENONE
ZON
(10s)-zearalenone
(e)--methyl-7-oxo
(s-(e))-xy-3-methyl
(s)-zearalenone
[s-(e)]-xy-3-methyl
16-dihydroxy-3-methyl-7-oxo-1trans-benzoxacyclotetradec-11-en-1-on
1h-2-benzoxacyclotetradecin-1,7(8h)-dione,3,4,5,6,9,10-hexahydro-14,16-dihydro
1h-2-benzoxacyclotetradecin-1-one,3,4,5,6,7,8,9,10-octahydro-14,16-dihydroxy-3
3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-1h-2-benzoxacyclotetradecin-1,
6-(10-hydroxy-6-oxo-1-undecenyl)-,mu-lactone,trans-resorcylicaci
6-(10-hydroxy-6-oxo-trans-1-undecenyl)-beta-resorcylicacidlactone
6-(10-hydroxy-6-oxo-trans-1-undecenyl)-beta-resorcylicacid-n-lactone
7(8h)-dione
compoundf-2
[EINECS(EC#)]

241-864-0
[Molecular Formula]

C18H22O5
[MDL Number]

MFCD00133085
[Molecular Weight]

318.36
[MOL File]

17924-92-4.mol
Chemical PropertiesBack Directory
[Appearance]

Crystalline Solid
[Melting point ]

164-165°C
[alpha ]

25546 -170.5° (c = 1.0 in CH3OH)
[Boiling point ]

377.53°C (rough estimate)
[density ]

1.1270 (rough estimate)
[refractive index ]

1.6120 (estimate)
[Fp ]

6 °C
[storage temp. ]

−20°C
[solubility ]

DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml; Ethanol: 20 mg/ml
[form ]

neat
[pka]

7.58±0.40(Predicted)
[color ]

Off-white
[Usage]

Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones
[Merck ]

13,10169
[BRN ]

1350216
[Major Application]

cleaning products
cosmetics
food and beverages
personal care
[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]

OC1=C(C(O[C@@H](C)CCC2)=O)C(/C=C/CCCC2=O)=CC(O)=C1
[LogP]

3.830 (est)
[CAS DataBase Reference]

17924-92-4(CAS DataBase Reference)
[EPA Substance Registry System]

17924-92-4(EPA Substance)
Questions And AnswerBack Directory
[Preparation]

benzene solution of AlI3 was prepared by stirring the reaction mixture of Al and I2. The methoxy reactant was then dissolved in anhydrous benzene and added to the AlI3 benzene solution. After the reaction was complete, an aqueous solution of NH4Cl and an aqueous solution of sodium metabisulfite were added to quench the reaction. The reaction mixture was then extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4. The desiccant was removed by filtration, and the resulting filtrate was concentrated under vacuum. The residue was then purified by silica gel (EtOAc/PE, 30:70) column chromatography to obtain the target product molecule, Zearalenone.
Safety DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)Health Hazard (GHS08)
GHS05,GHS08
[Signal word ]

Danger
[Hazard statements ]

H314-H361d
[Precautionary statements ]

P202-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
[Hazard Codes ]

C,Xn,F
[Risk Statements ]

R34:Causes burns.
R62:Possible risk of impaired fertility.
R63:Possible risk of harm to the unborn child.
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S16:Keep away from sources of ignition-No smoking .
S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

UN 3261 8/PG 2
[WGK Germany ]

3
[RTECS ]

DM2550000
[F ]

10
[TSCA ]

TSCA listed
[HS Code ]

29322090
[Storage Class]

3 - Flammable liquids
[Hazard Classifications]

Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 2
[Hazardous Substances Data]

17924-92-4(Hazardous Substances Data)
Hazard InformationBack Directory
[General Description]

White microcrystals or white powder.
[Reactivity Profile]

ZEARALENONE(17924-92-4) is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This chemical may be incompatible with alkalis.
[Air & Water Reactions]

This chemical may be sensitive to prolonged exposure to air. Insoluble in water.
[Fire Hazard]

Flash point data for this chemical are not available. ZEARALENONE is probably combustible.
[Chemical Properties]

Crystalline Solid
[Uses]

A phytoestrogenic mycotoxin and ER activator
[Uses]

Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones
[Uses]

Zearalenone is a resorcylic acid lactone produced by a number of Fusarium sp.. Zearalenone acts as a non-steroidal estrogen, binding to estrogen receptor and is uterotropic. Zearalenone induces reproductive problems in animals and, in some animal models, is thought to be a primary initiator of hepatic tumours. In vivo, zearalenone undergoes metabolic reduction to the more estrogenic zearalenol. Contamination of grains, notably maize, by Fusarium species gives rise to high levels of zearalenone and is regarded as an important food quality issue for both humans and animal health.
[Definition]

ChEBI: A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.
[Biochem/physiol Actions]

Zearalenone, a fungal mycotoxin produced by Fusarium, binds the estrogen receptor (ER) and is uterotropic in the newborn rat. It is a common contaminant in cereal grain used for animal and human food, and exerts an estrogenic activity that modulates/disrupts endocrine function in animals and possibly humans.
[Metabolic pathway]

When zearalenone is subjected to microbial transformation by a fungus, Gliocladium roseum, it is converted to a 1 : 1 mixture of 1-(3,5-dihydroxyphenyl)- 10 0 -hydroxy-1-undecen-6'-one and 1-(3,5- dihydroxyphenyl)-6'-hydroxy-1-undecen-10'-one.
[storage]

-20°C
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

[S-(E)]-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione(17924-92-4).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Zearalenone(17924-92-4)1HNMR
Zearalenone(17924-92-4)FT-IR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

17924-92-4(sigmaaldrich)
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