899-39-8

Usage

Chemical class

Steroid hormone and androgen

Precursor

Testosterone

Production sites

Adrenal glands and gonads

Role in biosynthesis

Crucial in the biosynthesis of androgens and estrogens

Conversion

Acts as an intermediate in the conversion of androstenedione to testosterone and estrone

Additional conversion

Can be converted to estrone in peripheral tissue

Properties

Has both androgenic and estrogenic properties

Factors influencing production and levels

Age, sex, and hormonal imbalances

Medical applications

Commonly measured in the diagnosis of certain medical conditions and in hormone replacement therapy

InChI:InChI=1/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h12-15,17,22H,3-10H2,1-2H3/t12-,13-,14-,15+,17-,18+,19-/m0/s1

Upstream product

• 58-22-0 testosterone 
• 1458-93-1 6β-bromotestosterone acetate 
• 96364-71-5 6β-methoxy-17β-hydroxy-4-androstene-3-one 
• 16375-05-6 3,3-Dimethoxy-5α-androstan-17β-ol-6-on-acetat 
• 63-05-8 Androstenedione 
• 16375-04-5 3-Ethoxy-2β-chlor-androsta-3,5-dien-17β-ol-acetat 
• 855-60-7 17β-acetoxy-2α-chloro-androst-4-en-3-one 
• 25469-53-8 17β-acetoxy-5α-androstan-3,6-dione 
• 745-43-7 5β-Androstan-17β-ol-3,6-dion-17-acetat 
• 62-99-7 6β-hydroxytestosterone 

Downstream Products

• 17328-37-9 3,17β-dihydroxy-5α-androstan-6-one 
• 4601-47-2 (3R,5S,8R,9S,10R,13S,14R)-3-Hydroxy-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-6,17-dione 
• 53512-53-1 3α-hydroxy-5α-androstane-6,17-dione 
• 132255-44-8 3α-(dimethylphenylsiloxy)-17β-hydroxy-5α-androstan-6-one 
• 22630-54-2 3α,6α-Dihydroxy-5α-androstan-17-on 
• 226713-94-6 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane 
• 226714-62-1 3β-((dimethylphenylsilyl)oxy)-6-methylene-5α-androstan-17-one 
• 257619-77-5 17α-bromo-3α-(triphenylsilyloxy)-5α-androstan-6-one 

Relevant academic research and scientific papers

Microbial transformation of androstenedione by Cladosporium sphaerospermum and Ulocladium chartarum

In this work, incubations of androstenedione 1 with Cladosporium sphaerospermum MRC 70266 and Ulocladium chartarum MRC 72584 have been reported. C. sphaerospermum MRC 70266 mainly hydroxylated 1 at C-6β, accompanied by a hydroxylation at C-15α, a reduction at C-17, a 5α-reduction and oxidations at C-6 and C-16 following hydroxylations. U. chartarum MRC 72584 hydroxylated 1 at C-6β, C-7α, C-7β and C-14α, accompanied by an oxidation at C-6 following its hydroxylation, a reduction at C-17 and a 5α-reduction. 6β,17β-Dihydroxyandrost-4-en-3,16-dione 8, one of the metabolites from the incubation of 1 with C. sphaerospermum MRC 70266, was determined as a new compound.

Biotransformation of testosterone by Ulocladium chartarum MRC 72584

The incubation of testosterone 1 with Ulocladium chartarum MRC 72584 has been reported. U. chartarum MRC 72584 hydroxylated testosterone 1 at C-7β, C-6β, C-14α and C-12β, accompanied by a 5α-reduction and oxidations at C-6 and at C-17.

Reactions of Enolizable Steroidal 4-En-3-ones and 17-Ones with Hypervalent Iodine

Reaction of the 3-oxo-4-androsten-derivative 1 or 4 with 1.2 eq. of o-iodosylbenzoic acid in methanolic KOH gave the methoxy products, the 4-methoxide 2 or 5 and the 6β-methoxide 3 or 6, along with dehydrated compound, the 4,6-dienone 7 or 8, respectively.Treatment of the 6-methoxide 3 or 6 with trimethylsilyl iodide yielded the 5α-androstane-3,6-dioxo derivative 11 or 12 in high yield.The same hypervalent oxidation of the 17-oxo steroid 15, 18, 21 or 24 using excess iodine and a longer reaction time produced the corresponding 16α-hydroxy-17,17-dimethylacetal 16, 19,22 or 25, which was converted into the 16α-hydroxy-17-one 17, 20, 23 or 26 by treatment with diluted HCl in every case.Keywords - hypervalent iodine oxidation; o-iodosylbenzoic acid; 4-en-3-oxo steroid; 17-oxo steroid; methoxylation; dehydration; 16α-hydroxy-17,17-dimethoxy steroid; 16α-hydroxy-17-oxo steroid; 5α-saturated 3,6-dioxo steroid

METABOLISM OF PROGESTERONE AND TESTOSTERONE BY A BACILLUS SP.

Microbial transformations by a Bacillus sp. were employed as a means of preparing potentially important derivatives of progesterone and testosterone.Each microbial metabolite was subjected to structure elucidation employing 1H and 13C nmr, mass spectral and cd analysis.HPLC was used for the determination of the percentages of the metabolites formed.The progesterone metabolites were characterised as 14-hydroxy-4-pregnene-3,20-dione (II), 14-hydroxy-5α-pregnane-3,6,20-trione (III), 11α-hydroxy-5α-pregnane-3,6,20-trione (IV) and 11α,14-dihydroxy-4-pregnene-3,20-dione (V).The testosterone analogs were identified as 4-androstene-3,17-dione (VII), 17β-hydroxy-5α-androstane-3,6-dione (VIII), 14-hydroxy-4-androstene-3,17-dione (IX) and 14,17β-dihydroxy-4-androsten-3-one (X).The availability of the metabolites enabled complete elucidation of their 13C nmr spectra.

Synthesis and some reactions of 6-bromoandrogens: Potential affinity ligand and inactivation of estrogen synthetase

The synthesis of epimeric 6-bromo-4-androstene-3,17-dione (1a and 1b), 6-bromotestosterone (2a and 2b) and its acetate (3a and 3b), and 6-bromo-16α-acetoxy-4-androstene-3,17-dione (5a and 5b), and 6β-bromo-16α-hydroxy-4-androstene-3,17-dione (4) is described. The interconversions among compounds 1, 2, and 3 are also studied. The 6β-isomer (1b, 2b, and 3b) was epimerized to the 6α-isomer (1a, 2a and 3a) in carbon tetrachloride or chloroform-methanol (9:1) and the 6α-isomer was isolated by fractional crystallization from the epimeric mixture. 6α-Bromo isomer 1a was also epimerized back to 6β-bromo isomer 1b in chloroform-methanol (9:1). Two polymorphic forms of 6β-bromotestosterone acetate (3b) were isolated (mp. 114-117° and 138-141°). The 6β-bromo isomers were found to be unstable in methanol and decomposed to give 5α-androstane-3,6-dione derivative (6). The results of irreversible inactivation of human placental androgen aromatase with some of these 6-bromoandrogens are discussed.