Zearalenone

Molecular Formula

C18H22O5

M.W.

318.36

CAS number

17924-92-4

MSDS

Download

Details

Source

Giberella zeae

Fermentek product Code

ZRE-001

Brand/grade

For research

Specifications

Appearance

White to Off-White powder

Purity by HPLC

≥98% ; refer to CoA for more data

Purity By TLC

≥98% ; refer to CoA for more data

Melting point

159°C-166°C

Solubility test

Clear colourless solution at 5mg/ml of Methanol

Chemical identification

Names and identifiers

IUPAC : (3S,11E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione

RTECS: DM2550000

EU number

241-864-0

Description

Zearalenone is a natural estrogen, a mycotoxin from resorcylic acid lactone group.

Zearalenone is a non-steroidal estrogenic mycotoxin produced by
several Fusarium spp. It has been implicated in numerous
mycotoxicoses in farm animals, especially in pigs. Zearalenone is
heat-stable and is found worldwide in a number of cereal crops, such
as maize, barley, oats, wheat, rice, and sorghum (Kuiper-Goodman et
al., 1987; Tanaka et al., 1988a) and also in bread (Aziz et al.,
1997). Zearalenone was shown to be produced on corn by Fusarium
isolates from Australia, Europe, and North America (Vesonder et al.,
1991) and in New Zealand (diMenna et al., 1997), the Philippines,
Thailand, and Indonesia (Yamashita et al., 1995). The occurrence of
zearalenone in food and feed was also demonstrated in South America
(Dalcero et al., 1997; Molto et al., 1997), Africa (Doko et al.,
1996), China and the former USSR (Ueno et al., 1986). Fusarium
isolates from bananas can also produce zearalenone

InChl Key

MBMQEIFVQACCCH-QBODLPLBSA-N

Canonical SMILES

CC1CCCC(=O)CCCC=CC2=CC(=CC(=C2C(=O)O1)O)O

Isomeric SMILES

C[C@H]1CCCC(=O)CCC/C=C/C2=CC(=CC(=C2C(=O)O1)O)O

Further Information

Solubility ( literature )

Zearalenone is slightly soluble in hexane and progressively more in benzene, acetonitrile, dichloromethane, methanol, acetone. In water: 20 mg/L .

Compound Classification

Mycotoxin
A resorcylic acid lactone
Sexual reproduction in Fusarium is regulated by the fungal sex hormone zearalenone, which is known to be synthesized only by species of Gibberella zeae (Fusarium roseum)

Storage, handling

Store in a freezer upon arrival, at -10°C to -25°C

Keep the lid tightly closed.

Avoid exposing to strong direct light.

Other vendors may recommend higher temperatures for storage.

Applications

The resorcylic acid lactones have estrogenic activity. Zearalenone and its derivates were used as veterinary anabolic or estrogen substitutes.

Disclaimer

For Research use only

Not for Human or Drug use

Not extracted from humans or animals

Refer to MSDS for further safety and handling instructions

Not for veterinary use!

Warnings

Warning or harmful

Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, categories 2, 3
Eye irritation, category 2A
Skin sensitization, category 1
Specific target organ toxicity following single exposure, category 3
- Respiratory tract irritation
- Narcotic effects