66212-25-7

Basic information

• Product Name: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one
• Synonyms: 17-Hydroxypregna-1,4,6-triene-3,20-dione; pregna-1,4,6-triene-3,20-dione, 17-hydroxy-
• CAS NO: 66212-25-7
• Molecular Formula: C₂₁H₂₆O₃
• Molecular Weight: 326.43
• EINECS: 613-906-1
• Mol File: 66212-25-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 502.9°C at 760 mmHg
• Flash Point: 272.1°C
• Density: 1.19g/cm³
• Vapor Pressure: 3.2E-12mmHg at 25°C
• Refractive Index: 1.592
• Water Solubility: 20mg/L at 25℃
• CAS DataBase Reference: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one(66212-25-7)
• EPA Substance Registry System: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one(66212-25-7)

Safety Data

• Hazardous Substances Data: 66212-25-7(Hazardous Substances Data)

Usage

Description

(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one is a complex organic compound with a specific stereochemistry and molecular structure. It is characterized by its unique arrangement of atoms and functional groups, which may have potential applications in various fields due to its specific properties.

Uses

Used in Pharmaceutical Industry:
(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one is used as an intermediate in the synthesis of 6-Deschloro Cyproterone Acetate (Cyproterone Acetate EP Impurity A) (D288520). (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one is an impurity of Cyproterone acetate (C989100), which is a medication used for treating androgen-dependent conditions such as prostate cancer and hirsutism.
(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one's specific stereochemistry and molecular structure make it a valuable component in the synthesis of pharmaceuticals, particularly those targeting androgen-dependent conditions. Its use in the pharmaceutical industry highlights the importance of understanding and manipulating molecular structures to create effective treatments for various medical conditions.

Flammability and Explosibility

Notclassified

Upstream product

• 2477-60-3 17α-hydroxypregna-4,6-diene-3,20-dione 
• 676-58-4 methylmagnesium chloride 
• 917-64-6 methyl magnesium iodide 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 
• 633-35-2 1,4,6-androstatriene-3,17-dione 
• 74-83-9 methyl bromide 
• 74-87-3 methylene chloride 
• 68-96-2 17-hydroxyprogesterone 

Downstream Products

• 15262-77-8 delmadinone 
• 13698-49-2 6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione 
• 15423-97-9 1,2α-methylene-6,7α-oxido-Δ4-pregnen-17α-ol-3,20-dione-17-acetate 
• 2701-50-0 1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate 
• 2098-65-9 17α-hydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione 
• 427-51-0 cyproterone acetate 
• 17183-98-1 6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate 

Relevant articles and documents

Preparation method of 1,6-didehydrogenation-17a-hydroxyl progesterone product

The invention provides a preparation method of a 1,6-didehydrogenation-17a-hydroxyl progesterone product. The preparation method includes the steps that 1,4-androstenedione (IDD) is adopted as a raw material, firstly, IDD molecules and acetone cyanohydrin

Method for preparing delmadinone acetate product

The invention provides a method for preparing a delmadinone acetate product. The method comprises the following steps: by taking IDD (1,4-Androstadienedione) as a raw material, firstly, enabling 17-site ketone in IDD molecules to react with acetone cyanohydrins in a first organic solvent under catalysis of an alkali, and introducing beta-hydroxyl and alpha-cyan into the 17-site so as to obtain hydroxyl cyanogens; preparing 1,6-bidehydrogenation-17a-hydroxyl progesterone from the hydroxyl cyanogens in the presence of methyl magnesium halide, a second organic solvent and an acid; further synthesizing a 6-site epoxy substance, further synthesizing 6-site chloride so as to obtain delmadinone, and finally carrying out 17-site esterification so as to obtain delmadinone acetate; and further carrying out heating backflow decoloring and recrystalization on the obtained delmadinone acetate with activated carbon in lower-carbon alcohol with the carbon number of smaller than 4, thereby obtaining the delmadinone acetate product. Compared with a conventional synthesis method, the method provided by the invention has multiple advantages of being simple and convenient in process operation, economic and environmental-friendly in production, high in total synthesis yield, high in product quality, low in production cost, and the like.

Method for preparing 1,6-bi-dehydrogenized-17a-hydroxy progesterone

The invention provides a method for preparing 1,6-bi-dehydrogenized-17a-hydroxy progesterone. The method comprises the following steps: firstly, adopting a nutrient medium and one or more microbial strain for performing microbial fermentation on phytosterol, thereby acquiring 1,4-androstenedione, namely, IDD; taking IDD as a raw material and reacting with acetone cyanohydrins in a first organic solvent under the condition of base catalysis, thereby acquiring hydroxyl cyanide; preparing the 1,6-bi-dehydrogenized-17a-hydroxy progesterone by using the hydroxyl cyanide under the existence of methyl magnesium halide, second organic solvent and acid. Compared with the traditional production method which uses diosgenin as the raw material, the method using IDD as the raw material according to theinvention has the advantages of extensive source of raw material, economical and environment-friendly process, greatly reduced production cost, and the like; in the invention, high-cost and toxic DDQand chloranil dehydrogenating agent are no longer used; solvents used in the process are recyclable, economical, environment-friendly and beneficial to industrial production.