58-22-0 Usage
Chemical Properties
White crystalline powder with no aroma. Its melting point is 155℃,
specific rotary power is [α]24D+109° (4%, ethanol), and its
ethanol solution has the greatest absorbance at a wavelength of
240nm. It is easily soluble in ethanol (1:5), soluble in ether
(1:100), and insoluble in water. LD50 (Large mice, venal
transfusion) 326mg/kg. Studies show that it has latent carcinogenic
effects on test animals.
Indications and Uses
Testosterone is the main natural male sex hormone in mammals and is
a steroid hormone with 19 carbon atoms. It is the main male sex
hormone secreted by the testes, and it is also the most active male
sex hormone. It promotes humans’ and animals’ sex organ and
secondary sex characteristic development, sperm maturation, and
protein metabolism for muscle strengthening.
Testosterone controls the growth and development of male sex organs
and male secondary sex characteristics. It is mainly used in
replacement therapy for eunuchism, treatment for male menopause
syndrome, and treatment for impotence, and it is also used in
biochemical research.
Pharmacokinetics
Testosterone can bind non-specifically with plasma albumins in
blood, and it can also bind with plasma sex hormone binding
globulins. It can be converted into estradiol and estrone in
peripheral tissue. Testosterone is mostly degraded in the liver,
where its A-ring is restored, and it is converted into 17-
ketosteroid under the effects of 17β-Hydroxysteroid dehydrogenase.
Along with androsterone, epiandrosterone, and etiocholanlone, it is
combined with glucuronic acid or sulfate and excreted in urine. Most
metabolites in urine that are excreted by binding to glucuronic acid
belong to 17-ketosteroids.
Application in Particular Diseases
In Osteoporosis:
Testosterone replacement is not FDA approved for the prevention or treatment of osteoporosis. It should not be used solely for these indications but might be beneficial to reduce bone loss in patients needing therapy for hypogonadal symptoms. In a few studies, women receiving oral methyltestosterone 1.25 or 2.5 mg daily or testosterone implants 50 mg every 3 months had increased BMD. Various salt forms of testosterone were associated with increased BMD in some studies of hypogonadal men or senior men with normal hormone levels or mild hormonal deficiency. Transdermal gel, oral, intramuscular, and pellet testosterone products are available.
Patients using them should be evaluated within 1 to 2 months of initiation and then every 3 to 6 months thereafter.
Description
Different sources of media describe the Description of 58-22-0 differently. You can refer to the following data:
1. Testosterone (Item No.15645) is an analytical reference material categorized as an anabolic androgenic steroid. Testosterone is an endogenous metabolite of androstenedione (Item Nos. ISO60161 | 15874) and estradiol (Item Nos. ISO60155 | 10006315). Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes. Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.
2. Testosterone (CRM) (Item No. ISO60154) is a certified reference material categorized as an anabolic androgenic steroid. Testosterone is an endogenous metabolite of androstenedione (Item Nos. ISO60161 | 15874) and estradiol (Item Nos. ISO60155 | 10006315). Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes. Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.
Uses
Different sources of media describe the Uses of 58-22-0 differently. You can refer to the following data:
1. 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.
2. androgen, antineoplastic
3. 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.
4. 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
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.
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.
Safety Profile
Confirmed carcinogen with experimental neoplastigenic and teratogenic data. Poison by intraperitoneal route. Human teratogenic effects by unspecified route: developmental abnormalities of the urogenital system. Experimental reproductive effects. Human mutation data reported. Workers engaged in manufacture and packagmg have shown effects from this hormone, e.g., enlargement of the breasts in male workers. A promoter. When heated to decomposition it emits acrid smoke and irritating fumes. Used as a drug for the treatment of hypogonadism and metastatic breast cancer.
Synthesis
Testosterone, 17β-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 17β-hydroxy compound. In the given example, reduction by sodium borohydride or
hydrogen over Raney nickel leads to the formation of 3β-acetoxy-5-androsten-17β-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–C6 to C4–C5 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 58-22-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 58-22:
(4*5)+(3*8)+(2*2)+(1*2)=50
50 % 10 = 0
So 58-22-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14?,15?,16?,17-,18-,19-/m0/s1
58-22-0Relevant articles and documents
A novel synthetic approach to steroids via intramolecular 1,3-dipolar cycloaddition. A highly stereocontrolled synthesis of testosterone
Ihara,Tokunaga,Fukumoto
, p. 4497 - 4498 (1990)
-
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Heyl,Herr
, p. 1918 (1953)
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STEREOSELECTIVE SYNTHESIS OF (+)-TESTOSTERONE VIA INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDE
Ihara, Masataka,Tokunaga, Yuji,Taniguchi, Nobuaki,Fukumoto, Keiichiro
, p. 6635 - 6648 (1991)
A new approach for construction of the A/B ring system of steroids was developed by way of an intramolecular 1,3-dipolar cycloaddition of a nitrile oxide 4, followed by an incorporation of a C3 unit.A highly stereocontrolled synthesis of (+)-testosterone 1 was accomplished by this strategy. Key Words: Steroids, testosterone, 1,3-dipolar cycloaddition, nitrile oxide, chiral synthesis
Influence of whole microalgal cell immobilization and organic solvent on the bioconversion of androst-4-en-3,17-dione to testosterone by Nostoc muscorum
Arabi,Yazdi, M. Tabatabaei,Faramarzi
, p. 213 - 217 (2010)
The use of free, immobilized and reused immobilized cells of the microalga Nostoc muscorum was studied for bioconversion of androst-4-en-3,17-dione (AD) to testosterone in hexadecane. Among polymers such as agar, agarose, κ-carrageenan, polyacrylamide, polyvinyl alcohol, and sodium alginate that were examined for cell entrapment, sodium alginate with a concentration of 2% (w/v) proved to be the proper matrix for N. muscorum cells immobilization. The bioconversion characteristics of immobilized whole algal cells at ranges of temperatures, substrate concentrations, and shaking speeds were studied followed by a comparison with those of free cells. The conditions were 30°C, 0.5. g/L, and 100. rpm, respectively. The immobilized N. muscorum showed higher yield (72 ± 2.3%) than the free form (24 ± 1.3%) at the mentioned conditions. The bioconversion yield did not decrease during reuse of immobilized cells and remained high even after 5 batches of bioreactions while Na-alginate 3% was used; however, reuse of alginate 2% beads did not give a satisfactory result.
SYNTHESIS OF TESTOSTERONE FROM ANDROST-4-ENE-3,17-DIONE
Andryushina, V. A.,Morozova, L. S.,Grinenko, G. S.
, p. 883 - 884 (1987)
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ANDROSTENEDIONE AND TESTOSTERONE BIOSYNTHESIS BY THE ANDRENAL CORTEX OF THE HORSE
Silberzahn, Pierre,Rashed, Fakhri,Zwain, Ismail,Leymarie, Pierre
, p. 147 - 152 (1984)
An homogenate from cortical tissue of mare adrenals was incubated in the presence of tritiated pregnenolone.The (3H) androstenedione and the (3H) testosterone synthesized during the incubation were extracted, purified, and co-crystallized to constant specific activity in the presence of unlabeled carriers.The rate of conversion of pregnenolone to androstenedione and testosterone was of the order of 5 and 0.15 per cent respectively.The high ratio of (3H) androstenedione to (3H) testosterone observed in this study suggests that androstenedione is the main androgen produced by mare adrenals.It is concluded that adrenals could contribute to the production of blood androgens in normal as well as hyperandrogenic mares.
The aging Leydig cell: 2. Two distinct populations of Leydig cells and the possible site of defective steroidogenesis
Chen,Lin,Murono,Osterman,Cole,Nankin
, p. 63 - 72 (1981)
Using metrizamide gradient centrifugation two populations of Leydig cells were found in both 60-90 day old and 24 month old rats. Cells from both Band 2 (B2) and Band 3 (B3) responded to LH stimulation with increased cyclic AMP formation; however, only B3 cells produced significant amounts of testosterone. Cells from both B2 and B3 of the old rats synthesized less cyclic AMP and testosterone than cells from their younger counterparts. In response to LH stimulation, 0.01 - 1.0 mIU/ml, no appreciable difference of cyclic AMP formation could be detected between young and old Leydig cells. Maximal testosterone production occurred when 1 mIU/ml LH was used. Only when LH concentration was increased to 10 and 100 mIU/ml, did young Leydig cells produce significantly more cyclic AMP than old Leydig cells. After addition of 5 x 10-7M of pregnenolone or progesterone to the incubation medium both young and old Leydig cells produced comparable amounts of testosterone. These results demonstrate no impairment of old rat Leydig cells to synthesize testosterone from pregnenolone and progesterone.
Synthesis method of alkyl acid testosterone
-
, (2020/12/10)
The invention discloses a synthesis method of alkyl acid testosterone, and belongs to the technical field of synthesis and processing of medicines. The method comprises the following steps of: taking4-androstenedione (4AD) as an initial raw material, firstly, carrying out enol ether protection on the keto group at the site 3, and reducing carbonyl at the site 17 into hydroxyl; or taking 4-androstenedione (4AD) as an initial raw material, firstly carrying out enol ether protection on the keto group at the site 3, then reducing carbonyl at the site 17 into hydroxyl, then carrying out hydrolysison the site 3 to obtain testosterone, and carrying out esterification and third-site hydrolysis to obtain the testosterone ester after testosterone third-site ketal protection. According to the method disclosed by the invention, the third site is protected during esterification reaction, the generation of impurities can be reduced, and an esterification reaction solvent is a water-insoluble organic solvent, so that after the reaction is completed, products can be directly extracted in a layered manner, a large amount of water does not need to be added to separate out the products, the amountof wastewater is reduced, the solvent can be recycled, and the process is more suitable for industrial production.
Regio- and stereoselective reduction of 17-oxosteroids to 17β-hydroxysteroids by a yeast strain Zygowilliopsis sp. WY7905
Liu, Yuanyuan,Wang, Yu,Chen, Xi,Wu, Qiaqing,Wang, Min,Zhu, Dunming,Ma, Yanhe
, p. 17 - 24 (2016/12/22)
The reduction of 17-oxosteroids to 17β-hydroxysteroids is one of the important transformations for the preparation of many steroidal drugs and intermediates. The strain Zygowilliopsis sp. WY7905 was found to catalyze the reduction of C-17 carbonyl group of androst-4-ene-3,17-dione (AD) to give testosterone (TS) as the sole product by the constitutive 17β-hydroxysteroid dehydrogenase (17β-HSD). The optimal conditions for the reduction were pH 8.0 and 30 °C with supplementing 10 g/l glucose and 1% Tween 80 (w/v). Under the optimized transformation conditions, 0.75 g/l AD was reduced to a single product TS with >90% yield and >99% diastereomeric excess (de) within 24 h. This strain also reduced other 17-oxosteroids such as estrone, 3β-hydroxyandrost-5-en-17-one and norandrostenedione, to give the corresponding 17β-hydroxysteroids, while the C-3 and C-20 carbonyl groups were intact. The absence of by-products in this microbial 17β-reduction would facilitate the product purification. As such, the strain might serve as a useful biocatalyst for this important transformation.
