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ZEARALANONE

CAS No.
5975-78-0
Chemical Name:
ZEARALANONE
Synonyms
Zanone;P-1502;Ccris 9235;ZEARALANONE;(S)-Zearalanone;Zearalanone solution;Zearalanone Standard;Zearalanone in Methanol;(S)-Zearalanone, P 1502, Zanone;(S)-Zearalanone in Acetonitrile
CBNumber:
CB1769935
Molecular Formula:
C18H24O5
Molecular Weight:
320.38
MDL Number:
MFCD00135821
MOL File:
5975-78-0.mol
MSDS File:
SDS
Last updated:2023-06-08 09:02:40

ZEARALANONE Properties

Melting point 184-186°C
Boiling point 576.8±50.0 °C(Predicted)
Density 1.148±0.06 g/cm3(Predicted)
Flash point 2℃
storage temp. -20°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka 7.83±0.40(Predicted)
color White to Off-White
FDA UNII 133DU2F2VS

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H302+H312+H332-H315-H319-H335-H351
Precautionary statements  P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313
Hazard Codes  Xn,F
Risk Statements  20/21/22-36/37/38-40-36-11
Safety Statements  22-26-36-36/37-16
RIDADR  UN 1648 3 / PGII
WGK Germany  3
HS Code  29322090
NFPA 704
0
3 0

ZEARALANONE price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Z0167 Zearalanone 5975-78-0 1mg $24.28 2024-03-01 Buy
Sigma-Aldrich 32193 Zearalanone solution 10 μg/mL in acetonitrile, analytical standard 5975-78-0 1.2ml $750 2022-05-15 Buy
Cayman Chemical 19459 Zearalanone ≥98% 5975-78-0 1mg $49 2024-03-01 Buy
Cayman Chemical 19459 Zearalanone ≥98% 5975-78-0 5mg $143 2024-03-01 Buy
Sigma-Aldrich Z0167 Zearalanone 5975-78-0 5mg $210 2024-03-01 Buy
Product number Packaging Price Buy
Z0167 1mg $24.28 Buy
32193 1.2ml $750 Buy
19459 1mg $49 Buy
19459 5mg $143 Buy
Z0167 5mg $210 Buy

ZEARALANONE Chemical Properties,Uses,Production

Chemical Properties

White to Off-White Solid

Uses

A secondary metabolite of Zearalenone (ZON). The macrocyclic lactone Zearalanone used in the synthesis of d,l-Zearalanol.

Uses

Zearalanone is a minor component of the zearalenone complex produced by several species of Fusarium. Like the more abundant analogues, zearalanone causes estrogenic effects in domestic livestock. Zearalanone is a metabolite of α-zearalanol, a commercially available growth promotant in animals, and is a useful standard for detection of zearanol-contaminated products and Fusarium-contaminated grains.

Definition

ChEBI: Zearalanone is a member of resorcinols and a macrolide.

General Description

Zearalanone (ZEA) or F-2 toxin, a nonsteroidal estrogenic mycotoxin is produced by various Fusarium species. Fusarium graminearum is considered as the primary producer of zearalanone. It is usually seen in moldy hay, high-moisture corn, corn infected before harvest etc.

Biological Activity

zearalanone (zan) is an estrogen receptor agonist and also an androgen receptor antagonist [1].zearalenone (zen), a β-resorcyclic acid lactone (ral), is a non-steroidal estrogenic mycotoxin biosynthesized by several fusarium species. zearalenone (zen) is the well-known mycotoxin present in numerous agricultural products [1][2][3][4]. in the human endometrial ishikawa cell line, zearalenone (zen) exhibited strong oestrogenicity [4].when incubated fusarium semitectum on sorghum, the ratio of zan to zen remained constant after 5 days, suggesting that zan might not be suitable for use as an internal standard [5].zearalanone, a major phase i metabolite of zearalenone (zen), is an estrogen receptor agonist and also an androgen receptor antagonist. in mcf-7 cells, zearalanone strongly induced cell proliferation with ec50 value of 1.21 nm and showed significant estrogenic activity. zearalanone behaved as full herα agonist. in palm cells, zearalanone acted as a har antagonist that strongly inhibited the luciferase activity induced by 0.3 nm of r1881, the synthetic androgen [1].

Biochem/physiol Actions

Zearalanone is believed to cause vulvovaginitis and estrogenic responses in swine.

References

[1]. molina-molina jm, real m, jimenez-diaz i, et al. assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. food chem toxicol.2014 dec;74:233-9.
[2]. baldwin rs, williams rd, terry mk. zeranol: a review of the metabolism, toxicology, and analytical methods for detection of tissue residues. regul toxicol pharmacol. 1983 mar;3(1):9-25.
[3]. migdalof bh, dugger ha, heider jg, et al. biotransformation of zeranol: disposition and metabolism in the female rat, rabbit, dog, monkey and man. xenobiotica. 1983 apr;13(4):209-21.
[4]. le guevel r, pakdel f. assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. hum reprod. 2001 may;16(5):1030-6.
[5]. aoyama k, ishikuro e, noriduki h, et al. formation ratios of zearalanone, zearalenols, and zearalanols versus zearalenone during incubation of fusarium semitectum on sorghum and ratios in naturally contaminated sorghum. shokuhin eiseigaku zasshi. 2015;56(6):247-51.

17924-92-4
5975-78-0
Synthesis of ZEARALANONE from Zearalenone

ZEARALANONE Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-Zearalanone, P 1502, Zanone (S)-3,4,5,6,9,10,11,12-Octahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione (S)-Zearalanone 2-[(S)-10-Hydroxy-6-oxoundecyl]-4,6-dihydroxybenzoic acid 1,2-lactone P-1502 Zanone 1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10,11,12-octahydro-14,16-dihydroxy-3-methyl-, (S)- beta-Resorcylic acid, 6-(10-hydroxy-6-oxoundecyl)-, mu-lactone Ccris 9235 Zearalanone,2,4-Dihydroxy-6-(10-hydroxy-6-oxoundecyl)benzoic acid μ-lactone 2,4-Dihydroxy-6-(10-hydroxy-6-oxoundecyl)benzoic acid μ-lactone solution Zearalanone solution ZEARALANONE 2,4-Dihydroxy-6-(10-hydroxy-6-oxoundecyl)benzoic acid μ-lactone 2,4-DIHYDROXY-6-[10-HYDROXY-6-OXO-UNDECYL]BENZOIC ACID MICRO-LACTONE Zearalanone (Certified Reference Material) Zearalanone Standard 1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10,11,12-octahydro-14,16-dihydroxy-3-methyl-, (3S)- Zearalanone 10.0 μg/ml Acetonitrile Zearalanone in Methanol (S)-Zearalanone in Acetonitrile 5975-78-0 Chiral Reagents Heterocycles Intermediates & Fine Chemicals Metabolites & Impurities Pharmaceuticals