Estra-1,3,5,7,9-pentaene-3,17beta-diol

Base Information

• Chemical Name: Estra-1,3,5,7,9-pentaene-3,17beta-diol
• CAS No.: 1423-97-8
• Molecular Formula: C18H20 O2
• Molecular Weight: 268.356
• European Community (EC) Number: 215-835-8
• DSSTox Substance ID: DTXSID40931405
• Nikkaji Number: J15.034G
• Wikipedia: 17%CE%B2-Dihydroequilenin
• Wikidata: Q28209318
• ChEMBL ID: CHEMBL123405
• Mol file: 1423-97-8.mol

Synonyms:17 beta-dihydroequilenin;17-dihydroequilenin;17-dihydroequilenin, (17 alpha)-isomer

Chemical Property of Estra-1,3,5,7,9-pentaene-3,17beta-diol

Chemical Property:

• Melting Point: 214-216°C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 350.53°C (rough estimate)
• Flash Point: 226.2oC
• PSA: 40.46000
• Density: 1.1199 (rough estimate)
• LogP: 3.73620
• Storage Temp.: Refrigerator
• Solubility.: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 268.146329876
• Heavy Atom Count: 20
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

17β-DihydroEquilenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3=C(C1CCC2O)C=CC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@]12CCC3=C([C@@H]1CC[C@@H]2O)C=CC4=C3C=CC(=C4)O
• Uses: The 17β-metabolite of Equilin (E592800).

Technology Process of Estra-1,3,5,7,9-pentaene-3,17beta-diol

There total 42 articles about Estra-1,3,5,7,9-pentaene-3,17beta-diol 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: 88.0%

D-3-methoxy-14α-estra-1,3,5(10),6,8-pentaen-17β-ol (15375-29-8) → 17β-dihydroequilenin (1423-97-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2016.09.062

Reference yield:

→ 17β-dihydroequilenin (1423-97-8) + 17α-dihydroequilenin (6639-99-2)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01286a060 DOI:10.1002/1520-6505(2000)9:5<201::AID-EVAN2>3.0.CO;2-Y

Reference yield:

equilenin (517-09-9) + aluminum isopropoxide (555-31-7) + isopropyl alcohol (67-63-0,8013-70-5) → 17β-dihydroequilenin (1423-97-8) + 17α-dihydroequilenin (6639-99-2)

Guidance literature:

DOI:10.1021/ja01286a060 DOI:10.1002/1520-6505(2000)9:5<201::AID-EVAN2>3.0.CO;2-Y

upstream raw materials:

(9S,13S,14S,17S)-13-Methyl-9,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

equilenin

aluminum isopropoxide

isopropyl alcohol

Downstream raw materials:

estradiol

estratriene-(B)-diol-(3α.17β)

estra-5,7,9-triene-3β,17β-diol

(+/-)-Z-Bisdehydrodoisynolic acid

Refernces

• 1、 Uskokovic,Gut. "". . p. 996. Retrieved 1957.
• 2、 Hylarides,Wilbur,Mettler Jr.. "B-ring aromatization of estrogen derivatives". . p. 657 - 662. Retrieved 2007/10/02.
• 3、 Bodenberger,Dannenberg. "Dehydrogenation of steroids. XVII. Dehydrogenation of estrogens and 3-acetaminoestra-1.3.5.(10)-triene-17 -ol with 2.3-dichloro-5.6-dicyanobenzoquinone (DDQ)". . p. 2389 - 2426. Retrieved 2007/10/06.