CAS 17924-92-4|(-)-zearalenone|(3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione|F-2 toxin|Zearalenone|Mycotoxin F2|(S,E)-14,16-dihydroxy-3-methyl-3,4,5...

Molecular Formula

C₁₈H₂₂O₅

Molecular Mass

318.36428

Exact Mass

318.1467238

InChI

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

Canonic Smiles

C[C@H]1CCCC(=O)CCC/C=C/c2c(C(=O)O1)c(O)cc(c2)O

Isomeric Smiles

C1(=O)c2c(cc(cc2O)O)/C=C/CCCC(=O)CCC[C@@H](O1)C

JChem

Acid pKa

8.5377245

H Acceptors

H Donor

LogD (pH = 5.5)

4.3737707

LogD (pH = 7.4)

4.3438344

Log P

4.3741655

Molar Refractivity

88.3395

Polarizability

33.566185

Polar Surface Area

83.83

Rotatable Bonds

Lipinski's Rule of Five

true

IUPAC name

(3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

IUPAC Traditional name

(-)-zearalenone

Synonyms

Mycotoxin F2Zearalenone(S,E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dioneF-2 toxinZenone(3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dioneZearalenone solutionFES(-)-Zearalenone玉米烯酮ZONMycotoxin F 2trans-ZearalenoneToxin F2Zearalenone玉米烯酮溶液

Beilstein Number

CAS Number

MDL Number

Wikipedia Title

Chemspider ID

PubChem SID

UN Number

3261

1648

RID/ADR

UN 3261 8/PG 2

UN 1648 3/PG 2

German water hazard class

GHS Hazard statements

H314-H361

H225-H302-H312-H319-H332

MSDS Link

Download link

GHS Precautionary statements

P280-P305+P351+P338-P310

P210-P280-P305+P351+P338

Packing Group

European Hazard Symbols

Corrosive (C)

Flammable (F)

Harmful (Xn)

Risk Statements

63-34-62

11-20/21/22-36

GHS Pictograms

Corrosive to metals, category 1

Skin corrosion, categories 1A,1B,1C

Serious eye damage, category 1

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Flammable gases, category 1

Flammable aerosols, categories 1,2

Flammable liquids, categories 1,2,3

Self-reactive substances and mixtures, Types B,C,D,E,F

Pyrophoric liquids, category 1

Pyrophoric solids, category 1

Self-heating substances and mixtures

Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3

Organic peroxides, Types B,C,D,E,F

RTECS

DM2550000

Hazard Class

GHS Signal Word

Danger

Personal Protective Equipment

Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Safety Statements

26-36/37/39-45

16-36/37

Storage Temperature

-20°C

Storage Condition

-20°C Freezer

Product Information

Purity

≥98.0% (TLC)

Empirical Formula (Hill Notation)

C18H22O5

Concentration

100 μg/mL in acetonitrile

Grade

analytical standard, for environmental analysis

Certificate of Analysis

Download link

Genuine Natural Compounds

Pharmacology Properties

Gene Information

mouse ... Esr1(13982)

Physical Property

No Data Available

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No Data Available

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Sigma Aldrich

96093

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.1

34126

General description
Certan Vial

TRC

Z270500

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

From Data Sources

• Hecht, S., et al.: Cancer Lett., 150, 49 (1988)

• Lim, H., et al.: J. Immunol., 175, 4180 (2

• Hamilton, S., et al.: Anticancer Res., 16, 3597 (1988)

• Hussein, H., et al.: Toxicology, 167, 101 (1988)

• Tanaka, T., et al.: J. Agric. Food Chem., 36, 979 (1988)