(4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one

Base Information

• Chemical Name: (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one
• CAS No.: 71030-11-0
• Molecular Formula: C18H24 O5
• Molecular Weight: 320.386
• Hs Code.: 29322090
• European Community (EC) Number: 664-283-8
• Wikipedia: Beta-Zearalenol
• Mol file: 71030-11-0.mol

Synonyms:71030-11-0;HMS2433I07;AKOS030254649

Chemical Property of (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one

Chemical Property:

• Vapor Pressure: 3.4E-15mmHg at 25°C
• Melting Point: 137-139°C
• Boiling Point: 599°C at 760 mmHg
• Flash Point: 217.9°C
• PSA: 86.99000
• Density: 1.174g/cm³
• LogP: 3.37140
• Storage Temp.: −20°C
• 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

β-Zearalenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N,F
• Statements: 20/21/22-40-52/53-68/20/21/22-50-36-22-11
• Safety Statements: 36/37-61-36-16

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](CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1)O
• Description: β-Zearalenol is a 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, β-zearalenol has pronounced effects on uterotropic activity and sperm acrosome reaction.
• Uses: Reactant involved in biological studies including:? ;Synthesis of amino glycoside nucleotides1? ;Enzymatic synthesis of glucuronides of zearalenone2? ;Derivatization of Zearalenone3,4,5 β-Zearalenol is a mycotoxin produced by several species of Fusarium. β-Zearalenol exhibits pronounced estrogenic activity, like other zearalenones. Contamination of grains by Fusarium species, notably maize, gives rise to high levels of zearalenol and is regarded as an important food quality issue for both human and animal health. The more active Zearalenone (Z270500) metabolite.

Technology Process of (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one

There total 29 articles about (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one 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]-β-zearalenol (445380-33-6) → beta-zearalenol (71030-11-0,40790-12-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 40 ℃;

DOI:10.1039/b005942k

Reference yield: 77.0%

(3S,7S,E)-14,16-dimethoxy-7-(4-methoxybenzyloxy)-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-benzo[c][1]oxacyclotetradecin-1-one → beta-zearalenol (71030-11-0,40790-12-3)

Guidance literature:

With iodine; tetra-(n-butyl)ammonium iodide; aluminium; In benzene; at 20 ℃; Inert atmosphere;

DOI:10.1080/00397911.2017.1383433

Reference yield: 60.0%

zearalenone (17924-92-4,7645-23-0) → beta-zearalenol (71030-11-0,40790-12-3)

Guidance literature:

With dipotassium hydrogenphosphate; sodium chloride; In N,N-dimethyl-formamide; glucose, yeast extract, neopeptone, Mucor bainieri NRRL 2988;

DOI:10.1021/jo00238a008

upstream raw materials:

zearalenone

Acetic acid (E)-(S)-2,4-dihydroxy-7-methyl-5-oxo-7,8,9,10,11,12,13,14-octahydro-5H-6-oxa-benzocyclotetradecen-11-yl ester

zearalenol 7α,β-O-chloroacetyl ester

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

Downstream raw materials:

4-methoxy-β-zearalenol

taleranol

7β-cis-zearalenol

Refernces

• 1、 Tadpetch, Kwanruthai,Kaewmee, Benyapa,Chantakaew, Kittisak,Kantee, Kawalee,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak. "Synthesis and cytotoxic activities of semisynthetic zearalenone analogues". supporting information. p. 3612 - 3616. Retrieved 2016/07/21.
• 2、 Stevenson, David E.,Hansen, Richard P.,Loader, Jared I.,Jensen, Dwayne J.,Cooney, Janine M.,Wilkins, Alistair L.,Miles, Christopher O.. "Preparative enzymatic synthesis of glucuronides of zearalenone and five of its metabolites". experimental part. p. 4032 - 4038. Retrieved 2010/03/31.