Chemical structure:

The C3 position is a β - configured hydroxyl group (- OH), and this hydroxyl group is acetylated (acetated to form an - OCOCH ∝ group).

The C20 position is a ketone carbonyl group (=O).

Belonging to steroid compounds (with a cyclopentane dihydrophenanthrene core).

There are two important double bonds in the molecule: one at positions 5 and 6 of the A ring (Δ ⁵), and one at positions 16 and 17 of the D ring (Δ ¹⁶).

Has two important oxygen-containing functional groups:

Molecular formula: C ₂∝ H ∝₀ O ∝

Structural formula: often written as Δ ⁵, ¹⁶ - pregnediene-3 β - ol-20-one-3-acetate.

Source and Production:

It is mainly prepared from natural steroidal saponins (such as diosgenin, which exists in plants such as Dioscorea nipponica and Dioscorea nipponica) through chemical degradation (ring opening) and oxidation reaction steps. Diosgenin is the most important starting material for this industrial route.

It is the core intermediate in the classic steroid drug semi synthetic route of "Diosgenin dienone acetate". This route is the foundation of the global steroid drug industry today.

China is the world's largest producer of diketone acetate, with major manufacturers including Tianjin Tianyao Pharmaceutical Co., Ltd. (formerly Tianjin Pharmaceutical Factory), Saito Biotech, and Xianju Pharmaceutical.

Importance (main purpose):

Adrenal cortex hormones: almost all glucocorticoids and mineralocorticoids such as cortisone, hydrocortisone, prednisone, prednisolone, dexamethasone, betamethasone, etc.

Sex hormones:

Other steroid drugs, such as spironolactone (diuretics), etc.

Progesterone: such as progesterone, medroxyprogesterone, medroxyprogesterone, norgestrel, etc.

Estrogen: such as estradiol, ethinylestradiol, etc. (usually requiring aromatization of the A ring).

Androgens/protein assimilation hormones: such as testosterone, methyltestosterone, methylprednisolone, etc.

The intermediate of steroid hormone drug synthesis: this is its most important value. Due to its unique structure (Δ ⁵ double bond, Δ ¹⁶ double bond, C3 acetate, C20 ketone group), dienone acetate can undergo a series of efficient chemical transformations (such as epoxidation, addition, hydrolysis, oxidation, reduction, microbial transformation, etc.) to introduce various key functional groups required for steroid drug molecules (such as C11-OH, C17-OH, C21-OH, etc.).

Starting materials for synthesizing various steroid drugs:

nature:

Usually white or off white crystalline powder.

There is a specific melting point range.

Insoluble in water, soluble in organic solvents such as ethanol, acetone, chloroform, etc.

There are unsaturated bonds and ester groups in the structure, and storage conditions should be taken into account (avoid light, dry, cool place).

Dienolone acetate (3 β - hydroxypregnest-5,16-dien-20-one acetate) is a core steroid intermediate obtained from the industrial preparation of plant steroidal saponins (mainly diosgenin). It is named after the presence of two double bonds (Δ ⁵ and Δ ¹⁶), one acetate group (at the C3 position), and one ketone group (at the C20 position) in its molecule. These functional groups make it a key starting material for the synthesis of almost all important adrenal cortex hormones (such as cortisone, dexamethasone) and sex hormones (such as progesterone, norgestrel, testosterone, estradiol, etc.). It is one of the most fundamental and important cornerstones of the modern steroid drug industry.