delta9,11-Estradiol

Base Information

• Chemical Name: delta9,11-Estradiol
• CAS No.: 791-69-5
• Molecular Formula: C18H22O2
• Molecular Weight: 270.371
• European Community (EC) Number: 641-998-3
• UNII: 99558VD54H
• DSSTox Substance ID: DTXSID60229538
• Nikkaji Number: J112.450A
• Wikidata: Q27272170
• Mol file: 791-69-5.mol

Synonyms:delta(9(11))-dehydro-17beta-estradiol;J 1213;J-1213

Chemical Property of delta9,11-Estradiol

Chemical Property:

• Melting Point: 174-175 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 468.3±45.0 °C(Predicted)
• PKA: 10.39±0.60(Predicted)
• PSA: 40.46000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 3.51890
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 270.161979940
• Heavy Atom Count: 20
• Complexity: 429

Purity/Quality:

98%min ^*data from raw suppliers

?9(11)-Estradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CC=C3C(C1CCC2O)CCC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@]12CC=C3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O
• Uses: 9(11)-Estradiol (Estradiol EP Impurity D) is a metabolite of Estradiol (E888000).

Technology Process of delta9,11-Estradiol

There total 18 articles about delta9,11-Estradiol 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: 99.9%

3-hydroxy-estra-1,3,5(10),9(11)-tetraen-17-one (1089-80-1) → 9(11)-Dehydroestradiol (791-69-5)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2006.06.136

Reference yield: 65.0%

estra-1,3,5(10),9(11)-tetraene-3,17β-diyl diacetate (1169-54-6) → 9(11)-Dehydroestradiol (791-69-5)

Guidance literature:

With potassium hydroxide; In methanol; at 40 ℃; for 4h;

DOI:10.1016/S0039-128X(99)00020-3

Reference yield: 39.29%

estradiol (50-28-2) → 9(11)-Dehydroestradiol (791-69-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; Reflux; Inert atmosphere;

upstream raw materials:

3-hydroxy-estra-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-tetraen-17-one

3-Oxo-9α,10α-oxido-17β-acetoxy-Δ⁴-oestren

3-acetoxy-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-estratetraen-17-one

3-acetoxy-9α-hydroxy-1,3,5(10)-estratrien-17-one

Downstream raw materials:

estradiol

9beta-Estradiol

3,17β-Bis(benzyloxy)estra-1,3,5(10),9(11)-tetraene

11beta-Hydroxyestradiol

Refernces

• 1、 -. "Estra -1, 3, 5 (10) - triene compound and preparation method and medical application thereof". Paragraph 0052-0054. . Retrieved 2021/09/29.
• 2、 Lao, Kejing,Wang, Yejun,Chen, Mingqi,Zhang, Jingjing,You, Qidong,Xiang, Hua. "Design, synthesis and biological evaluation of novel 2-methoxyestradiol analogs as dual selective estrogen receptor modulators (SERMs) and antiangiogenic agents". . p. 390 - 400. Retrieved 2017/08/22.