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58-22-0

Basic Information
CAS No.: 58-22-0
Name: Testosterone
Article Data: 195
Molecular Structure:
Molecular Structure of 58-22-0 (Testosterone)
Formula: C19H28O2
Molecular Weight: 288.43
Synonyms: Testosterone(7CI,8CI);(+)-Testosterone;17b-Hydroxy-D4-androsten-3-one;4-Androsten-3-one-17b-ol;Andro 100;Androderm;Andronaq;Androst-4-en-17b-ol-3-one;Androst-4-ene-17b-ol-3-one;Andrusol;COL 1621;Cristerona T;Geno-cristaux Gremy;Homosterone;Intrinsa;Mertestate;Neotestis;Opterone;Orquisteron;Percutacrineandrogenique;Primoteston;Relibra;Striant;Sustanone;Synandrol F;Testandrone;Testim;Testobase;Testogel;Testolin;Testosteron;Testro AQ;Testryl;Tostrex;Virormone;D4-Androsten-17b-ol-3-one;Nandrolone Phenylpropionate;Androst-4-en-3-one,17-hydroxy-, (17b)-;
EINECS: 200-370-5
Density: 1.12 g/cm3
Melting Point: 152-156 °C
Boiling Point: 432.9 °C at 760 mmHg
Flash Point: 184.7 °C
Solubility: 22.79mg/L(20 oC)
Appearance: white crystalline odourless solid
Hazard Symbols: ToxicT,HarmfulXn
Risk Codes: 60-61-11-19-20-40-63-45
Safety: 53-45-24/25-36/37
PSA: 37.30000
LogP: 3.87920
Synthetic route
57711-43-0

17β-<(t-butyldimethylsilyl)oxy>androst-4-en-3-one

58-22-0

testosterone

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In methanol at 20℃; for 32h;100%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In methanol at 20℃; for 32h;100%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 7h; Ambient temperature;92%
With lithium tetrafluoroborate In dichloromethane; acetonitrile78%
4126-29-8

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((tetrahydrofuran-2-yl)oxy)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

58-22-0

testosterone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;100%
975-57-5

3,3-(ethylenedioxy)-5-androsten-17β-ol

58-22-0

testosterone

Conditions
ConditionsYield
With sulfuric acid; water; silica gel In toluene for 0.5h;98%
With hydrogenchloride In methanol at 20℃; for 1h;94%
With silica gel; copper(II) sulfate In chloroform for 3h; Heating;82%
Edukt 1: aus Androst-4-en-3,17-dion;
Multi-step reaction with 5 steps
1: 90 percent / CrO3*(pyridine)2 / CH2Cl2 / 12 h / Ambient temperature
2: 1.) diisopropylamine, n-BuLi / 1.) THF, -78 deg C, 15 min
3: LiAlH4 / diethyl ether / 2 h / -15 °C
4: p-toluenesulfonic acid / acetone / 2 h / Heating
5: 39 percent / triphenyltin hydride / toluene / 2 h / Heating
View Scheme
61014-73-1

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((triethylsilyl)oxy)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

58-22-0

testosterone

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In methanol at 20℃; for 0.25h;98%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 1h; Ambient temperature;95%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In methanol at 20℃; for 0.25h;90%
26341-28-6

17β-(methoxymethoxy)androst-4-en-3-one

58-22-0

testosterone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; ethanethiol In dichloromethane for 0.5h; Ambient temperature;96%
1045-69-8

testosterone acetate

58-22-0

testosterone

Conditions
ConditionsYield
With copper dichloride In methanol; water for 20h; Heating;95%
With bis(tri-n-butyltin)oxide In toluene at 110℃; for 27h;59%
With potassium hydroxide
516-63-2

17β-(2'-tetrahydropyranyloxy)androst-4-en-3-one

58-22-0

testosterone

Conditions
ConditionsYield
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane for 1h; Ambient temperature;95%
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In methanol at 20℃; for 8h;92%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In methanol at 20℃; for 3h;90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; water for 7h; Ambient temperature;87%
51154-10-0

17β-hydroxy-4ξ,5-oxido-5ξ-androstan-3-one

58-22-0

testosterone

Conditions
ConditionsYield
With Amberlyst 15; sodium iodide In acetone at 20℃; for 6h; deoxygenation;95%
20860-15-5

17β-benzyloxy-testosterone

58-22-0

testosterone

Conditions
ConditionsYield
With dimethylsulfide; boron trifluoride diethyl etherate In dichloromethane at 30℃; for 19h;94.4%
Multi-step reaction with 2 steps
1: 84.5 percent / EtSH, boron trifluoride etherate / CH2Cl2 / 18 h / 30 °C
2: 83.3 percent / 5percent HCl / H2O; acetone / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 84.5 percent / boron trifluoride etherate / CH2Cl2 / 18 h / 30 °C
2: 83.3 percent / 5percent HCl / H2O; acetone / 1 h / Ambient temperature
View Scheme
63-05-8

Androstenedione

58-22-0

testosterone

Conditions
ConditionsYield
With zygowilliopsis sp. WY7905 In aq. phosphate buffer at 30℃; for 24h; pH=8; Enzymatic reaction; stereoselective reaction;93%
With potassium borohydride In tetrahydrofuran; dichloromethane; water at -10 - -5℃; Temperature;93%
With Trichoderma virens In ethanol at 24℃; for 96h; Microbiological reaction;60%
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Consensus Reports

IARC Cancer Review: Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 ,1974,p. 209.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) , IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 519.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 519.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

1. Introduction of Testosterone

The Testosterone is a steroid hormone from the androgen group and is found in mammals, reptiles, birds, and other vertebrates. The IUPAC name of this chemical is (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one. With the CAS registry number 58-22-0, it is also named as 17-Hydroxy-(17-beta)-androst-4-en-3-one. The product's categories are MI; TPI; steroids; intermediates & fine chemicals; pharmaceuticals; intracellular receptor. It is white crystalline odourless solid which is soluble in ethanol (1:5) and chloroform (1:2), dissolved in ether (1:100), and insoluble in water. When heated to decomposition it emits acrid smoke and irritating fumes.

2. Properties of Testosterone

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.48; (4)ACD/LogD (pH 7.4): 3.48; (5)ACD/BCF (pH 5.5): 257.74; (6)ACD/BCF (pH 7.4): 257.74; (7)ACD/KOC (pH 5.5): 1851.51; (8)ACD/KOC (pH 7.4): 1851.51; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.56; (13)Molar Refractivity: 83.11 cm3; (14)Molar Volume: 256.9 cm3; (15)Polarizability: 32.94×10-24 cm3; (16)Surface Tension: 44.4 dyne/cm; (17)Enthalpy of Vaporization: 79.52 kJ/mol; (18)Vapour Pressure: 2.6E-09 mmHg at 25°C; (19)Tautomer Count: 5; (20)Exact Mass: 288.20893; (21)MonoIsotopic Mass: 288.20893; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 21.

3. Structure Descriptors of Testosterone

You could convert the following datas into the molecular structure:
1). SMILES:O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
2). 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.

4. Toxicity of Testosterone

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral > 5gm/kg (5000mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 6, 1996.
rat LDLo intraperitoneal 326mg/kg (326mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Proceedings of the Society for Experimental Biology and Medicine. Vol. 46, Pg. 116, 1941.

5. Safety Information of Testosterone

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and harmful by inhalation. It is also may form explosive peroxides and has limited evidence of a carcinogenic effect. Additionally, Testosterone may impair fertility and cause harm to the unborn child, so people should avoid contact with skin and eyes. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid exposure - obtain special instructions before use. 

6. Use and Preparation of Testosterone

Uses of Testosterone: In mammals, it is primarily secreted in the testes of males and the ovaries of females, although small amounts are also secreted by the adrenal glands. It is the principal male sex hormone and an anabolic steroid. Testosterone is used for the treatment of eunuchism, male menopause syndrome, impotence and other diseases.

Preparation of Testosterone: The Androst-4-enedione is restored by lithium aluminum hydride, and oxidated by manganese dioxide. Then we can get the product.

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