alpha-Zearalenol

Base Information

• Chemical Name: alpha-Zearalenol
• CAS No.: 36455-72-8
• Molecular Formula: C18H24 O5
• Molecular Weight: 320.386
• Hs Code.: 29322090
• European Community (EC) Number: 828-728-1
• UNII: 59D4EVJ5KC
• DSSTox Substance ID: DTXSID8022402
• Nikkaji Number: J3.201.624C
• Wikipedia: Alpha-Zearalenol
• Wikidata: Q27890390
• Metabolomics Workbench ID: 49563
• ChEMBL ID: CHEMBL371463
• Mol file: 36455-72-8.mol

Synonyms:(-)-beta-zearalenol;(3R,7R,11E)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one;1H-2-benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7R,11E)-;3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one;alpha-zearalenol;alpha-zearalenol, (cis)-isomer;beta-trans-zearalenol;beta-zearalenol;zearalenol

Chemical Property of alpha-Zearalenol

Chemical Property:

• Vapor Pressure: 3.4E-15mmHg at 25°C
• Melting Point: 158-161°C
• Boiling Point: 599°Cat760mmHg
• PKA: 7.61±0.60(Predicted)
• Flash Point: 217.9°C
• PSA: 86.99000
• Density: 1.174g/cm³
• LogP: 3.37140
• Storage Temp.: 2-8°C
• Solubility.: ≤20mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• XLogP3: 4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 320.16237386
• Heavy Atom Count: 23
• Complexity: 408

Purity/Quality:

98%,99%, ^*data from raw suppliers

a-Zearalenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 20/21/22-40-52/53-68/20/21/22-36-11-62-48/20-63-46-45
• Safety Statements: 36/37-61-16-45-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCCC(CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1)O
• Isomeric SMILES: C[C@H]1CCC[C@@H](CCC/C=C/C2=C(C(=CC(=C2)O)O)C(=O)O1)O
• Description: α-Zearalenol is a major hepatic metabolite of zearalenone , a mycotoxin produced by fungi in food and animal feeds. It is a less potent agonist of estrogen receptors than the parent compound. However, α-zearalenol has pronounced effects on uterotropic activity, sperm motility, and preimplantation embryonic development.
• Uses: α-Zearalenol is a mycotoxin produced by several species of Fusarium. α-Zearalenol exhibits pronounced estrogenic activity, being 3-fold more active than zearalenone. Contamination of grains, notably maize, by Fusarium species gives rise to high levels of zearalenol and is regarded as an important food quality issue for both humans and animal health. α- Zearalenol may be used as an analytical reference standard for the determination of the analyte in traditional medicinal herbs, human and animal urine by various chromatography techniques. The major metabolites of Zearalenone

Technology Process of alpha-Zearalenol

There total 15 articles about alpha-Zearalenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2,4-bis[(2-methoxyethoxy)methyl]-α-zearalenol (445380-29-0) → α-zearalenol (36455-72-8,40790-12-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 40 ℃;

DOI:10.1039/b005942k

Reference yield: 58.0%

zearalenone (17924-92-4,7645-23-0) → beta-zearalenol (71030-11-0,40790-12-3) + α-zearalenol (36455-72-8,40790-12-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.06.007

Reference yield: 40.0%

zearalenone (17924-92-4,7645-23-0) → α-zearalenol (36455-72-8,40790-12-3)

Guidance literature:

With dipotassium hydrogenphosphate; sodium chloride; In N,N-dimethyl-formamide; glucose, yeast extract, neopeptone, Streptomyces griseus ATCC 13273;

DOI:10.1021/jo00238a008

upstream raw materials:

zearalenone

zearalenol 7α,β-O-chloroacetyl ester

2,4-bis[(2-methoxyethoxy)methyl]-α-zearalenol

(6E,8S,9S)-1-benzyloxy-8,9-dihydroxydec-6-en-5-one

Downstream raw materials:

4-methoxy-α-zearalenol

zeranol

Z-7α-zearalenol

Refernces

• 1、 Drzymala, Sarah S.,Herrmann, Antje J.,Maul, Ronald,Pfeifer, Dietmar,Garbe, Leif-Alexander,Koch, Matthias. "In vitro phase i metabolism of cis -zearalenone". . p. 1972 - 1978. Retrieved 2015/02/19.
• 2、 Burckhardt, Svenja,Ley, Steven V.. "The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol". . p. 874 - 882. Retrieved 2007/10/03.