Description
Testosterone (CRM) (Item No. ISO60154) is a certified reference material categorized as an anabolic androgenic steroid.
1 Testosterone is an endogenous metabolite of androstenedione (Item Nos.
ISO60161 |
15874) and estradiol (Item Nos.
ISO60155 |
10006315).
2 Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes.
1 Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.
Description
Testosterone (Item No.15645) is an analytical reference material categorized as an anabolic androgenic steroid.
1 Testosterone is an endogenous metabolite of androstenedione (Item Nos.
ISO60161 |
15874) and estradiol (Item Nos.
ISO60155 |
10006315).
2 Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes.
1 Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.
Uses
androgen, antineoplastic
Uses
Rivastigmine metabolite
Uses
Secreted by the testis and is converted to dihydrotestosterone in the target tissue where is appears to mediate many of the biological actions of testosterone.
CONTROLLED SUBSTANC
Uses
Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.
Uses
Testosterone, Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5α-reductase in androgen-dependent target tissues to 5α-dehydrotestosterone
which is required for normal male sexual differentiation. Also converted by aromatization to Estradiol.
Testerone is a controlled substance (anabolic steroid). Androgen.
Definition
ChEBI: An androstanoid having 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-41C-5..
General Description
Testosterone, 17β-hydroxyandrost-4-en-3-one, is a naturally occurring androgen in men. Inwomen, it mainly serves as a biosynthetic precursor to estradiolbut also has other hormonal effects. It is rapidly metabolizedto relatively inactive 17-ones, however,preventing significant oral activity. Testosterone is availablein a transdermal delivery system (patch), a gel formulation, abuccal system, and as implantable pellets.
Hazard
A confirmed carcinogen.
Health Hazard
Controls secondary male sex characteristics Maintains functional competence of male reproductive ducts and glands
Increases protein anabolism; maintains spermatogenesis; inhibits follotropin
Increases male sex behavior; increases closure of epiphyseal plates
Biological Activity
Endogenous androgen receptor agonist.
Biochem/physiol Actions
Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.
Synthesis
Testosterone, 17|?-hydroxyandrost-4-ene-3-one (29.1.5), is made in a number of ways from different substances, including cholesterol, although it is most often
made from androstenolone acetate. In order to do this, the keto-group at C17 of the steroid
system of androstenolone acetate is reduced to a hydroxyl group by either sodium borohydride, lithium aluminum hydride, or hydrogen over Raney nickel, all of which result in
a 17|?-hydroxy compound. In the given example, reduction by sodium borohydride or
hydrogen over Raney nickel leads to the formation of 3|?-acetoxy-5-androsten-17|?-ol
(29.1.1). The hydroxyl group resulting from reduction then undergoes acylation by benzoyl chloride in pyridine, which forms a diester (29.1.2). After that, taking into consideration the differences in the acidic region of the two ester groups present in the molecule as
well as the long-known fact that 17-hydroxy-group ester derivatives are harder to
hydrolyze than 3-hydroxy-group ester derivatives, the acetyl protection of the hydroxyl
group at C3 is removed by selective hydrolysis using potassium hydroxide in ethanol, and
the resulting alcohol (29.1.3) is oxidized to a ketone (29.1.4) by aluminum isopropylate in
the presence of cyclohexanone as a hydrogen acceptor, during which isomerization of the
double bond from position C5¨CC6 to C4¨CC5 simultaneously takes place. Subsequent hydrolysis of the remaining ester region of the molecule using an alkali gives the desired testosterone (29.1.5) . When necessary to convert this into the corresponding ester
(propionate, enantate, cypionate, and a few other testosterone esters), the necessary acylation can be accomplished.
Purification Methods
Crystallise testosterone from aqueous acetone, hexane or isoPrOH. The long needles that separated from EtOH/AcOH were used for X-ray crystallography [Roberts et al. J Chem Soc Perkin Trans II 1978 1973.] The acetate [1045-69-8] crystallises from MeOH or aqueous Me2CO, with m 140-141o and [] D 20 +87.8o (c 1, EtOH). [Ruzicka et al. Helv Chim Acta 18 1478 1935 and 19 99, 842 1936, Beilstein 8 IV 974.]
