2,4-O-Dimethylzearalenone

Base Information

• Chemical Name: 2,4-O-Dimethylzearalenone
• CAS No.: 10497-40-2
• Molecular Formula: C20H26O5
• Molecular Weight: 346.423
• UNII: 0LV1V4Z8XK
• ChEMBL ID: CHEMBL3827144
• Mol file: 10497-40-2.mol

Synonyms:2,4-O-Dimethylzearalenone;0LV1V4Z8XK;(+)-Zearalenone dimethyl ether;(S)-2,4-Di-O-methylzearalenone;UNII-0LV1V4Z8XK;10497-40-2;1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dimethoxy-3-methyl-, (3S,11E)-;(4S,12E)-16,18-dimethoxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione;CHEMBL3827144;AKOS001582843;CCG-103037;(11E)-14,16-DIMETHOXY-3-METHYL-3,4,5,6,7,8,9,10-OCTAHYDRO-1H-2-BENZOXACYCLOTETRADECINE-1,7-DIONE

Chemical Property of 2,4-O-Dimethylzearalenone

Chemical Property:

• Melting Point: 114 - 115 °C
• PSA: 61.83000
• LogP: 4.18560
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 346.17802393
• Heavy Atom Count: 25
• Complexity: 473

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC(=O)CCCC=CC2=C(C(=CC(=C2)OC)OC)C(=O)O1
• Isomeric SMILES: C[C@H]1CCCC(=O)CCC/C=C/C2=C(C(=CC(=C2)OC)OC)C(=O)O1

Technology Process of 2,4-O-Dimethylzearalenone

There total 62 articles about 2,4-O-Dimethylzearalenone 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: 98.0%

zearalenone (17924-92-4,7645-23-0) + methyl iodide (74-88-4) → 2,4-Dimethoxy-zearalenone (10497-40-2,7533-25-7)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.06.007

Reference yield: 97.0%

(S)-(-)-zearalenone dimethyl ether ethylene glycol (16320-11-9) → 2,4-Dimethoxy-zearalenone (10497-40-2,7533-25-7)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 40 ℃; for 26h;

Reference yield: 85.0%

(3S)-7-hydroxy-14,16-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one (1333419-84-3) → 2,4-Dimethoxy-zearalenone (10497-40-2,7533-25-7)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0030-1260058

upstream raw materials:

zearalenone

(2S)-6-Oxooct-7-en-2-yl 2,4-dimethoxy-6-<3-bromoprop-1-(E)-enyl>benzoate

(+)-(S)-dimethylzearalenone trimethylene dithioketal

(S)-(-)-zearalenone dimethyl ether ethylene glycol

Downstream raw materials:

2,4-Dimethoxy-6--benzoesaeure

zearalenone

2-<10-Hydroxy-6-oxo-undecen-(1)-yl>-4,6-dimethoxy-benzoesaeure

1-(3,5-dimethoxy-6-carboxyphenyl)-10-methylsulfonate-1-undecene 6-ethylene ketal

Refernces

• 1、 Baggelaar, Marc P.,Huang, Yange,Feringa, Ben L.,Dekker, Frank J.,Minnaard, Adriaan J.. "Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor". . p. 5271 - 5274. Retrieved 2013/09/02.
• 2、 Napolitano, Carmela,McArdle, Patrick,Murphy, Paul V.. "Access to resorcylic acid lactones via phosphonate based intramolecular olefination". supporting information; experimental part. p. 7404 - 7407. Retrieved 2011/02/22.