6-Dehydroestrone

Base Information

• Chemical Name: 6-Dehydroestrone
• CAS No.: 2208-12-0
• Molecular Formula: C18H20O2
• Molecular Weight: 268.356
• European Community (EC) Number: 636-647-6
• NSC Number: 48999
• DSSTox Substance ID: DTXSID401043221
• Nikkaji Number: J142.419J
• Wikidata: Q27115999
• ChEMBL ID: CHEMBL418970
• Mol file: 2208-12-0.mol

Synonyms:3-HETO;3-hydroxyestra-1,3,5(10),6-tetraen-17-one

Chemical Property of 6-Dehydroestrone

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.91E-09mmHg at 25°C
• Refractive Index: 1.605
• Boiling Point: 454.7 °C at 760 mmHg
• Flash Point: 193.6 °C
• PSA: 37.30000
• Density: 1.19 g/cm³
• LogP: 3.89800
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 268.146329876
• Heavy Atom Count: 20
• Complexity: 454

Purity/Quality:

99% ^*data from raw suppliers

6-Dehydroestrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)C=CC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)C=CC4=C3C=CC(=C4)O
• Uses: 6-Dehydroestrone is used in the synthetic preparation of estrogens with potential inhibitory activity against lipoxygenase enzymes.

Technology Process of 6-Dehydroestrone

There total 25 articles about 6-Dehydroestrone 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%

17,17-ethanediyldioxy-estra-1,3,5(10),6-tetraen-3-ol (23820-90-8) → 6-dehydroestrone (2208-12-0)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00019-6

Reference yield: 74.0%

estra-4,6-diene-3,17-dione (13209-45-5) → 6-dehydroestrone (2208-12-0)

Guidance literature:

In N,N-dimethyl-formamide; at 30 ℃; for 46h; Corynebacterium simplex (ATCC 6946);

DOI:10.1021/jo00277a045

Reference yield: 35.0%

3,3:17,17-bis(ethylenedioxy)-5,10-epoxy-5β,10β-oestran-6β-ol (1249-41-8,81969-02-0) → 6-dehydro-oestrone (2208-12-0)

Guidance literature:

With hydrogen bromide; acetic acid; for 0.25h; Heating;

upstream raw materials:

3,3:17,17-bis(ethylenedioxy)-5,10-epoxy-5β,10β-oestran-6β-ol

3,3:17,17-bis(ethylenedioxy)oestr-5(10)-en-6β-ol

Estrone quinol

1,4,6-androstatriene-3,17-dione

Downstream raw materials:

7α-bromo-1,3,5(10)-estratriene-3,6β,17β-triol 6-methyl ether

Estrone

3-O-methyl-estra-1,3,5⁽¹⁰⁾,6-tetraen-17-one

6-Dehydroestradiol

Refernces

• 1、 Rao, Pemmaraju N.,Wang, Zhiqiang. "New synthesis of Δ6-estrogens". . p. 487 - 490. Retrieved 1997.
• 2、 Jing, Yu,Xu, Cheng-Gong,Ding, Kai,Lin, Jing-Rong,Jin, Rong-Hua,Tian, Wei-Sheng. "Protecting group effect on the 1,2-dehydrogenation of 19-hydroxysteroids: a highly efficient protocol for the synthesis of estrogens". scheme or table. p. 3242 - 3245. Retrieved 2010/08/19.
• 3、 Brosa,Ferrer,Malet,Amezaga. "Synthesis of 3-methoxyestra-1,3,5(10),6-tetraen-17-one". . p. 3984 - 3985. Retrieved 2007/10/02.