Estra-1,4-diene-3,17-dione, 10-hydroxy-

Base Information

• Chemical Name: Estra-1,4-diene-3,17-dione, 10-hydroxy-
• CAS No.: 549-03-1
• Molecular Formula: C18H22O3
• Molecular Weight: 286.371
• NSC Number: 700499
• DSSTox Substance ID: DTXSID10203388
• Nikkaji Number: J79.373F
• Wikidata: Q83076765
• ChEMBL ID: CHEMBL2002912
• Mol file: 549-03-1.mol

Synonyms:ESTRA-1,4-DIENE-3,17-DIONE, 10-HYDROXY-;549-03-1;10-Hydroxyestra-1,4-diene-3,17-dione;(8S,9S,10S,13S,14S)-10-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione;BRN 2004182;4-08-00-02404 (Beilstein Handbook Reference);NSC700499;SCHEMBL3890929;CHEMBL2002912;DTXSID10203388;10.beta.-Hydroxyestra-1,17-dione;NSC-700499;NCI60_036110

Chemical Property of Estra-1,4-diene-3,17-dione, 10-hydroxy-

Chemical Property:

• Vapor Pressure: 1.89E-11mmHg at 25°C
• Boiling Point: 485.2°C at 760 mmHg
• Flash Point: 261.3°C
• Density: 1.24g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 286.15689456
• Heavy Atom Count: 21
• Complexity: 587

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=CC(=O)C=CC34O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)C=C[C@]34O

Technology Process of Estra-1,4-diene-3,17-dione, 10-hydroxy-

There total 4 articles about Estra-1,4-diene-3,17-dione, 10-hydroxy- 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: 28.0%

10β-hydroperoxy-estra-1(2),4(5)-dien-3,17-dione (86846-54-0) → Estrone (53-16-7) + Estrone quinol (549-03-1) + 10β-chloro-estra-1(2),4(5)-dien-3,17-dione (91413-55-7)

Guidance literature:

With copper dichloride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(01)87222-7

Reference yield: 16.0%

Oestron-3-acetat (901-93-9,21610-87-7,34990-86-8,57605-53-5,57605-54-6,57605-55-7) → (+/-)-oestrone (19973-76-3) + hydroxy-1 estrone (58697-99-7,60966-54-3) + acetoxy-3 hydroxy-1 estrone (95717-16-1) + hydroxy-10β estradiene-1,4 dione-3,17 (549-03-1,86900-15-4,109581-81-9)

Guidance literature:

With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride; at -57 ℃; for 0.25h; Yields of byproduct given;

DOI:10.1016/S0040-4020(01)91262-1

Reference yield: 12.0%

estrone acetate (901-93-9) → Estrone (53-16-7) + Estrone quinol (549-03-1) + Acetic acid (8R,9S,13S,14S)-4-hydroxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl ester + Acetic acid (8R,9S,13S,14S)-1-hydroxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester

Guidance literature:

With hydrogen fluoride; dihydrogen peroxide; antimony(III) fluoride; at -45 ℃; for 0.0125h; Further byproducts given;

upstream raw materials:

10β-hydroperoxy-estra-1(2),4(5)-dien-3,17-dione

estrone acetate

Oestron-3-acetat

Downstream raw materials:

1,4-diacetoxyestra-1,3,5(10)-trien-17-one

10β-acetoxyestra-1,4-dien-3,17-dione

6-dehydroestrone

Estrone

Refernces

• 1、 Maumy, Michel,Capdevielle, Patrice. "Chemical evidence for peroxy radicals intermediacy in copper(II) reaction with hydroperoxides". . p. 7455 - 7462. Retrieved 2007/10/02.