9-hydroxy-4-androstene-3,17-dione ( 4-OHA)(link:https://www.bloomtechz.com/synthetic-chemical/api-researching-only/9-hydroxy-4-androstene-3-17-dione-cas-560-62.html) is a steroid compound. Because its molecular structure has various functional groups and stereoisomers, it has a wide range of biological activities and pharmacological effects. 9-hydroxy-4-androstene-3,17-dione (4-OHA) is a steroid compound, its full name is 9-hydroxy-4-androstene-3,17-dione.
9-hydroxy-4-androstene-3,17-dione structure:
1. Main skeleton structure:
9-hydroxy-4-androstene-3,17-dione belongs to androstenoid steroids and has an androstene skeleton. Its main skeleton consists of four rings, including three six-membered rings and one five-membered ring. These four rings are numbered sequentially as A ring, B ring, C ring and D ring.
2. Functional group:
In the structure of 9-hydroxy-4-androstene-3,17-dione, there are many important functional groups. Among them, the hydroxyl group (-OH) is located on the ninth carbon of the A ring, which is the source of "9-hydroxy" in the compound name. In addition, there are two keto groups (-C=O), which are respectively located on the third carbon and the seventeenth carbon of the B ring, which constitute the part of "4-androstene-3,17-dione".
3. Three-dimensional configuration:
In terms of stereo configuration, 9-hydroxy-4-androstene-3,17-dione has multiple chiral centers, so multiple isomers can exist. These chiral centers are located at the fifth carbon (C-5), sixth carbon (C-6), and seventh carbon (C-7) of the A ring, and the nineteenth carbon (C-19) of the D ring, respectively. This means that there may be 16 different isomers, whose stereoconfiguration may have an important impact on its biological activity.
4. Bond length and bond angle:
In the structure of 9-hydroxy-4-androstene-3,17-dione, the bond length and bond angle between each atom can be determined by chemical experiments and calculation methods. Among them, carbon-carbon (C-C) and carbon-hydrogen (C-H) bonds generally have average bond lengths of about 1.54 Å and about 1.09 Å. In addition, the length of carbon-oxygen (C-O) bonds is generally about 1.43 Å, and the length of oxygen-hydrogen bonds (O-H) of hydroxyl groups is usually about 0.96 Å. The carbon-keto (C=O) bond has a bond length of about 1.22 Å.
5. Resonant structure:
Due to the presence of multiple double bonds and functional groups, 9-hydroxy-4-androstene-3,17-dione has a series of resonance structures. The resonance structure can explain its properties and response behavior, and further reveal the mechanism of its action in vivo.
9-hydroxy-4-androstene-3 17-dione properties:
1. Oxidation reaction:
9-hydroxy-4-androstene-3,17-dione (9-hydroxy-4-androstene-3,17-dione) is an active steroid compound, which can undergo various oxidation reactions. It can be oxidized by oxidizing agents to its derivatives, such as ketone body 4-androstene-3,17-dione or methylated products. These reactions can be carried out by commonly used oxidizing agents (such as chromic acid, hydrogen peroxide) or other catalysts.
9-hydroxy-4-androstene-3,17-dione (9-hydroxy-4-androstene-3,17-dione) is an active steroid compound, which can undergo various oxidation reactions.
1.1. Ketone body formation reaction:
9-Hydroxy-4-androstene-3,17-dione can be oxidized to the corresponding ketone body, such as 4-androstene-3,17-dione (4-androstene-3,17-dione).
Chemical formula:
C19H26O3 → C19H26O2 + H2O
1.2. Hydroxyoxidation reaction:
9-Hydroxy-4-androstene-3,17-dione can also be oxidized by oxidizing agents to derivatives with higher oxidation states, such as 9,11α-epoxy-17α-hydroxy-4-androstene-3,20 - Dione (9,11α-epoxy-17α-hydroxy-4-androstene-3,20-dione).
Chemical formula:
C19H26O3 + oxidizing agent → 9,11α-epoxy-17α-hydroxy-4-androstene-3,20-dione + H2O
1.3. Hydroxymethylation reaction:
Under some specific conditions, 9-hydroxy-4-androstene-3,17-dione can be hydroxymethylated by oxidation reaction to form the corresponding hydroxymethyl compound, such as 9-hydroxy-11α-methyl- 4-androstene-3,17-dione (9-hydroxy-11α-methyl-4-androstene-3,17-dione).
Chemical formula:
C19H26O3 + oxidizing agent + methyl donor → 9-hydroxy-11α-methyl-4-androstene-3,17-dione + H2O
2. Reduction reaction:
9-hydroxy-4-androstene-3,17-dione can be converted into its metabolic derivatives, such as testosterone or dihydrotestosterone, through a reduction reaction. These reactions can be carried out using reducing agents (such as hydrogen, metal catalysts) or reductases.
2.1. Ketone reduction:
9-Hydroxy-4-androstene-3,17-dione can be reduced to testosterone or dihydrotestosterone by ketone reduction.
Chemical formula:
C19H26O3 + NADH + H+ → C19H28O2 + NAD+ + H2O
2.2. Hydroxyl reduction:
The hydroxyl group of 9-hydroxy-4-androstene-3,17-dione can also be reduced to methyl compounds by reduction reaction, such as 9α-methyl-4-androstene-3,17-dione (9α-methyl -4-androstene-3,17-dione).
Chemical formula:
C19H26O3 + NADPH + H+ → 9α-methyl-4-androstene-3,17-dione + NADP+ + H2O
2.3. Reduction of cycloalcohols:
The cyclic alcohols of 9-hydroxy-4-androstene-3,17-dione can also be reduced to the corresponding cyclic ether products.
Chemical formula:
C19H26O3 + NADH + H+ → cyclic ether product + NAD+ + H2O
3. Dehydration reaction:
9-hydroxy-4-androstene-3,17-dione undergoes dehydration reaction under appropriate conditions to form products with double bond structures and compounds with different structures. For example 4-androstene-3,17-dione (4-androstene-3,17-dione).
3.1. α-hydroxyl dehydration:
Under appropriate conditions, 9-hydroxy-4-androstene-3,17-dione can undergo an α-hydroxy dehydration reaction to form the corresponding estrogenic compounds, such as estrone (estrone) or 17β-estradiol (estradiol ).
Chemical formula:
C19H26O3 → estrogenic compound + H2O
3.2. Hydroxydehydration:
Another dehydration reaction is the dehydration of the hydroxyl group of 9-hydroxy-4-androstene-3,17-dione to generate the corresponding alkene compound.
Chemical formula:
C19H26O3 → olefin compound + H2O
4. Esterification reaction:
The hydroxyl group of 9-hydroxy-4-androstene-3,17-dione can react with acid to form ester compounds. This reaction usually requires an acid catalyst and is accompanied by the formation of water.
Examples of esterification reactions:
C19H26O3 + acid/anhydride → ester
Among them, the acid/anhydride can be some kind of acidic compound or anhydride, commonly used acids include benzoic acid, acetic acid and the like. The esterification reaction generally requires appropriate reaction conditions and is carried out in a suitable solvent.
5. Ketone reduction reaction:
The ketone group of 9-hydroxy-4-androstene-3,17-dione can be reduced by dehydrogenase to produce testosterone or dihydrotestosterone. These reactions occur widely in living organisms.
5.1. Reduction to generate testosterone (testosterone):
Under appropriate conditions, 9-hydroxy-4-androstene-3,17-dione can be reduced to testosterone, ie 17β-hydroxy-4-androstene-3-one.
Chemical formula:
C19H26O3 + NADH + H+ → C19H28O2 + NAD+ + H2O
5.2. Reduction to generate dihydrotestosterone (dihydrotestosterone):
In addition, 9-hydroxy-4-androstene-3,17-dione can also be reduced to dihydrotestosterone, 5α-dihydrotestosterone or 17β-hydroxy-5α-androstene-3-one.
Chemical formula:
C19H26O3 + NADPH + H+ → Dihydrotestosterone + NADP+ + H2O