2208-12-0

Basic information

• Product Name: 6-DEHYDROESTRONE
• Synonyms: 3-hydroxyestra-1,3,5(10),6-tetraen-17-one;1,3,5[10],6-ESTRATETRAEN-3-OL-17-ONE;3-HYDROXY-1,3,5[10],6-ESTRATETRAEN-17-ONE;6-DEHYDROESTRONE;6-dehydroestrone crystalline;1,3,5(10),6-Estratetraen-3-ol-17-one, 3-Hydroxy-1,3,5(10),6-estratetraen-17-one;3-Hydroxy-1,3,5(10),6-estratetren-17-one;3-Hydroxyestra-1,3,5(10),6-tetren-17-one
• CAS NO: 2208-12-0
• Molecular Formula: C₁₈H₂₀O₂
• Molecular Weight: 268.35
• Mol File: 2208-12-0.mol

Chemical Properties

• Boiling Point: 454.7 °C at 760 mmHg
• Flash Point: 193.6 °C
• Appearance: /white powder
• Density: 1.19 g/cm³
• Vapor Pressure: 6.91E-09mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 6-DEHYDROESTRONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-DEHYDROESTRONE(2208-12-0)
• EPA Substance Registry System: 6-DEHYDROESTRONE(2208-12-0)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 2208-12-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Dehydroestrone is used as a precursor in the synthetic preparation of estrogens for various medical applications. These estrogens have potential inhibitory activity against lipoxygenase enzymes, which are involved in various physiological processes and diseases.
Used in Research and Development:
6-Dehydroestrone is also utilized in research and development for the study of steroid hormone synthesis, metabolism, and their effects on the human body. This knowledge can contribute to the development of new drugs and therapies targeting hormone-related conditions and diseases.

InChI:InChI=1/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,14-16,19H,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

Upstream product

• 1249-41-8 3,3:17,17-bis(ethylenedioxy)-5,10-epoxy-5β,10β-oestran-6β-ol 
• 1246-95-3 3,3:17,17-bis(ethylenedioxy)oestr-5(10)-en-6β-ol 
• 549-03-1 Estrone quinol 
• 633-35-2 1,4,6-androstatriene-3,17-dione 
• 13209-45-5 estra-4,6-diene-3,17-dione 
• 23820-90-8 17,17-ethanediyldioxy-estra-1,3,5⁽¹⁰⁾,6-tetraen-3-ol 
• 53-16-7 Estrone 
• 900-83-4 (8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 4147-12-0 10β-acetoxyestra-1,4-dien-3,17-dione 
• 27759-21-3 6β-bromo-androsta-1,4-diene-3,17-dione 
• 24130-35-6 19-acetoxy-androsta-1,4,6-trien-3,17-dione 
• 19269-79-5 6-Hydroxy-oestron 
• 116282-37-2 6-Hydroxy-oestron-3,6-dibenzoat 

Downstream Products

• 7291-41-0 6-Dehydroestradiol 
• 17253-36-0 3-O-methyl-estra-1,3,5⁽¹⁰⁾,6-tetraen-17-one 
• 53-16-7 Estrone 
• 115375-37-6 7α-bromo-1,3,5(10)-estratriene-3,6β,17β-triol 6-methyl ether 

Relevant articles and documents

New synthesis of Δ6-estrogens

An efficient approach to synthesize Δ6-estrogens is described. The key steps in the synthesis are the introduction of a hydroxyl group at the Δ6 position of a suitably protected estrogen using a superbase and subsequent dehydration with Martin sulfurane reagent or methyltriphenoxyphosphonium iodide. The two-step synthetic procedure readily gave the Δ6-estrogens in high yield.

Protecting group effect on the 1,2-dehydrogenation of 19-hydroxysteroids: a highly efficient protocol for the synthesis of estrogens

19-O-Acylation was found to be indispensable for 1,2-dehydrogenation of 19-hydroxyandrost-4-ene-3,17-dione 1a with DDQ as an oxidant after exploring a variety of C-19 substituents. 1,2-Dehydrogenation in combination with subsequent A-ring aromatization via retro-aldol reaction provided a flexible and efficient protocol for the synthesis of estrogens. To demonstrate the utility of the protocol, pharmaceutically attractive estrogens were synthesized from easily available 19-hydroxy-4-ene-3-keto steroids.

Treating cardiac disorders with Δ9(11)-dehydro-8-isoestrone

This invention relates to 8α-3-hydroxyestra- 1,3,5( 10),9( 11 )tetraen-17-one (Δ9( 11 )-dehydro-8-isoestrone) (VI), STR1 to the process for its preparation, to pharmaceutical compositions containing said 8α-3-hydroxyestra- 1,3,5(10), 9(11)tetraen-17-one (Δ9(11)-dehydro-8-isoestrone) (VI) and to the use of said 8α-3-hydroxyestra-1,3,5(10),9(11 )tetraen-17-one (A9( 11 )-dehydro-8-isoestrone) (VI) for modifying the balance between bone production and bone resorption, and as an antioxidant in a host animal, including man.

Selective Aromatization of Ring B in 19-Norsteroids and Synthesis of Equilenin-type Compounds

The preparation of 7α-acetoxy-3,3:17,17-bis(ethylenedioxy)-5,10-epoxy-5β,10β-oestran-6-one (4) is described.When heated with alkali it undergoes ring B aromatization to give 3,3:17,17-bis(ethylenedioxy)oestra-5(10),6,8-triene-6,7-diol (7), without configurational change at C(14).Bis-deacetalization of the corresponding diacetate (8), followed by lead tetra-acetate aromatization of ring A in the resulting diketone (9), produces 6,7-diacetoxyequilenin (10), which is finally converted into its 3-acetate (11).The same ester product (11) could also be obtained by conversion of the diketone (9) into its 3-enol acetate (12), followed by lead tetra-acetate dehydrogenation.