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58-22-0 Usage

Uses

Rivastigmine metabolite

Biological Activity

Endogenous androgen receptor agonist.

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.

Chemical Properties

white crystalline odourless solid

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

Hazard

A confirmed carcinogen.

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.

Definition

ChEBI: An androstanoid having 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-41C-5..

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.

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

androgen, antineoplastic

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.

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.

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.]
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

58-22-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Testosterone

1.2 Other means of identification

Product number -
Other names AndroGel

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-22-0 SDS

58-22-0Synthetic route

17β-<(t-butyldimethylsilyl)oxy>androst-4-en-3-one
57711-43-0

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

testosterone
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%
(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
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

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;100%
3,3-(ethylenedioxy)-5-androsten-17β-ol
975-57-5

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

testosterone
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
(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
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

testosterone
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%
17β-(methoxymethoxy)androst-4-en-3-one
26341-28-6

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

testosterone
58-22-0

testosterone

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

testosterone acetate

testosterone
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
17β-(2'-tetrahydropyranyloxy)androst-4-en-3-one
516-63-2

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

testosterone
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%
17β-hydroxy-4ξ,5-oxido-5ξ-androstan-3-one
51154-10-0

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

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With Amberlyst 15; sodium iodide In acetone at 20℃; for 6h; deoxygenation;95%
17β-benzyloxy-testosterone
20860-15-5

17β-benzyloxy-testosterone

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
Androstenedione
63-05-8

Androstenedione

testosterone
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%
testosterone triflate
159949-15-2

testosterone triflate

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With 18-crown-6 ether; cesium acetate In benzene for 2h; Product distribution; Heating;92%
Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium formate In butan-1-ol at 113 - 116℃; for 8h; Inert atmosphere;91.9%
17β-(3-methyl-2-butenyloxy)androst-4-en-3-one

17β-(3-methyl-2-butenyloxy)androst-4-en-3-one

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 0.75h;89%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 0.75h;89%
17β-hydroxy-4β,5-epoxy-5β-androstan-3-one
2189-83-5

17β-hydroxy-4β,5-epoxy-5β-androstan-3-one

A

testosterone
58-22-0

testosterone

B

5β,17β-dihydroxyandrostan-3-one
121145-41-3

5β,17β-dihydroxyandrostan-3-one

Conditions
ConditionsYield
With acetic acid; sodium phenylseleno(triethyl)borate In ethanol at 20℃; for 0.166667h; Reduction; dehydration;A 6%
B 88%
4-androstenediol
1156-92-9

4-androstenediol

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With 3,5-dimethyl-1H-pyrazole; pyridinium chlorochromate In dichloromethane at 2 - 3℃; for 0.5h;87%
With trimethylamine-N-oxide; CHDFe-(CO)3 In acetone at 20℃; for 10h;76%
With C10H16NO5; potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -15℃; for 4h; chemoselective reaction;85%Spectr.
testosterone 2-(prenyloxymethyl)benzoate
850848-14-5

testosterone 2-(prenyloxymethyl)benzoate

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
Stage #1: testosterone 2-(prenyloxymethyl)benzoate With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 6h;
Stage #2: With ytterbium(III) triflate In dichloromethane at 20℃; for 3h;
87%
Multi-step reaction with 2 steps
1: DDQ / CH2Cl2; H2O / 6 h / 20 °C
2: Yb(OTf)3*H2O / CH2Cl2 / 7 h / 20 °C
View Scheme
17β-methoxy-4-androsten-3-one
13990-32-4

17β-methoxy-4-androsten-3-one

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With aluminium trichloride; sodium iodide In acetonitrile for 5h; Ambient temperature;86%
(+)-(8R,9S,10R,13S,14S,17S)-17-t-Butoxy-4-androsten-3-one
1852-99-9

(+)-(8R,9S,10R,13S,14S,17S)-17-t-Butoxy-4-androsten-3-one

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With trifluoroacetic acid86%
With trifluoroacetic acid for 1.16667h; Ambient temperature;86%
17β-benzyloxy-testosterone
20860-15-5

17β-benzyloxy-testosterone

A

testosterone
58-22-0

testosterone

B

(8R,9S,10R,13S,14S,17S)-3-Ethylsulfanyl-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
77503-09-4

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; ethanethiol In dichloromethane at 30℃; for 18h;A 11.2%
B 84.5%
17β-benzyloxy-testosterone
20860-15-5

17β-benzyloxy-testosterone

ethanethiol
75-08-1

ethanethiol

A

testosterone
58-22-0

testosterone

B

(8R,9S,10R,13S,14S,17S)-3-Ethylsulfanyl-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
77503-09-4

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 30℃; for 18h;A 11.2%
B 84.5%
(8R,9S,10R,13S,14S,17S)-3-Ethylsulfanyl-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
77503-09-4

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

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With hydrogenchloride In water; acetone for 1h; Ambient temperature;83.3%
(8R,9S,10R,13S,14S)-3-Ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
26614-48-2

(8R,9S,10R,13S,14S)-3-Ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol at 40 - 45℃; Reagent/catalyst; Solvent; Green chemistry;82.8%
(8R,9S,10R,13S,14S,17R)-3-Methoxy-10,13-dimethyl-17-((E)-3-trimethylsilanyl-allyl)-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
74137-34-1

(8R,9S,10R,13S,14S,17R)-3-Methoxy-10,13-dimethyl-17-((E)-3-trimethylsilanyl-allyl)-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

A

testosterone
58-22-0

testosterone

B

17β-hydroxy-17α-(trimethylsilylprop-2-enyl)androst-4-en-3-one
74137-32-9

17β-hydroxy-17α-(trimethylsilylprop-2-enyl)androst-4-en-3-one

Conditions
ConditionsYield
With acidA 1%
B 82%
(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol
81176-75-2

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With nitrobenzene; palladium on activated charcoal In acetonitrile at 80℃; for 72h;82%
With tert.-butylhydroperoxide; Rh2(Msip)4; sodium hydrogencarbonate In dichloromethane; water at 40℃; for 24h; Sealed tube; chemoselective reaction;78%
des-A-17β-t-butyldimethylsilyloxy-10-(3',3'-dioxyethylene butyl)androstan-5-one

des-A-17β-t-butyldimethylsilyloxy-10-(3',3'-dioxyethylene butyl)androstan-5-one

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 5h; Heating;77.86%
Androstenedione
63-05-8

Androstenedione

A

testosterone
58-22-0

testosterone

B

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol
81176-75-2

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol

Conditions
ConditionsYield
With sodium tetrahydroborate In diethyl ether at 20℃; for 2h;A 70%
B 30%
(8R,9S,10R,13S,14S,17S)-6-[1,3]Dithian-2-yl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
79761-67-4

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

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With W-2 Raney nickel In acetone at 20℃; for 4h;60%
3-oxo-androst-4-en-17β-yl Se-phenyl selenocarbonate
76920-41-7

3-oxo-androst-4-en-17β-yl Se-phenyl selenocarbonate

A

testosterone
58-22-0

testosterone

B

4-androsten-3-one
2872-90-4

4-androsten-3-one

C

3-oxo-androst-4-en-17β-yl-methyl formate
3129-42-8

3-oxo-androst-4-en-17β-yl-methyl formate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃;A 29%
B 7%
C 59%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene at 144℃;A 23%
B 54%
C 21%
testosterone heptanoate
315-37-7

testosterone heptanoate

A

testosterone
58-22-0

testosterone

B

Androstenedione
63-05-8

Androstenedione

Conditions
ConditionsYield
With Fusarium fujikuroi PTCC 5144 In ethanol; water at 26℃; for 312h; Reagent/catalyst; Microbiological reaction;A 20%
B 17%
C 59%
testosterone
58-22-0

testosterone

Androstenedione
63-05-8

Androstenedione

Conditions
ConditionsYield
With Jones reagent In acetone at 0℃; Jones Oxidation;100%
With oxygen; nitrosonium tetrafluoroborate In dichloromethane at 20℃; for 4h;99%
With N-chloro-succinimide; dodecyl methyl sulfide; triethylamine In toluene at -40℃; for 16h; Corey-Kim oxidation;97%
testosterone
58-22-0

testosterone

acetic anhydride
108-24-7

acetic anhydride

testosterone acetate
1045-69-8

testosterone acetate

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 24h; Inert atmosphere;100%
With pyridine at 0 - 20℃;99%
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 3h;92%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

testosterone
58-22-0

testosterone

17β-(2'-tetrahydropyranyloxy)androst-4-en-3-one
516-63-2

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

Conditions
ConditionsYield
bis(trimethylsilyl)sulphate In dichloromethane; 1,2-dichloro-ethane at 0℃; for 0.333333h;100%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 6h; Ambient temperature;100%
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In acetonitrile at 20℃; for 24h;100%
testosterone
58-22-0

testosterone

acetic anhydride
108-24-7

acetic anhydride

(17β)-androsta-3,5-diene-3,17-diol diacetate
123880-21-7

(17β)-androsta-3,5-diene-3,17-diol diacetate

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide100%
testosterone
58-22-0

testosterone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

17β-<(t-butyldimethylsilyl)oxy>androst-4-en-3-one
57711-43-0

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

Conditions
ConditionsYield
N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Ambient temperature;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;95%
With 1H-imidazole In N,N-dimethyl-formamide for 18h; Ambient temperature;93%
monochloromethanesulfonyl chloride
3518-65-8

monochloromethanesulfonyl chloride

testosterone
58-22-0

testosterone

Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
182243-71-6

Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 0.25h;100%
With pyridine at 0℃; Substitution;
testosterone
58-22-0

testosterone

androst-4-en-17β-ol-3-one-[2,2,4,6,6-D5]
21002-80-2

androst-4-en-17β-ol-3-one-[2,2,4,6,6-D5]

Conditions
ConditionsYield
With [D]-sodium hydroxide; deuteromethanol; water-d2 at 120℃; for 0.0166667h; Inert atmosphere; Microwave irradiation;100%
testosterone
58-22-0

testosterone

trimethyl-[2-oxo-2-[[rac-(1S)-5-[(2-aminooxyacetyl)amino]-1-[(2-methyltetrazol-5-yl)methylcarbamoyl]pentyl]amino]ethyl]ammonium 2,2,2-trifluoroacetic acid salt

trimethyl-[2-oxo-2-[[rac-(1S)-5-[(2-aminooxyacetyl)amino]-1-[(2-methyltetrazol-5-yl)methylcarbamoyl]pentyl]amino]ethyl]ammonium 2,2,2-trifluoroacetic acid salt

C35H58N9O5(1+)

C35H58N9O5(1+)

Conditions
ConditionsYield
With acetic acid In methanol at 45℃; for 2h;100%
testosterone
58-22-0

testosterone

trans-4-butylcyclohexane carboxylic acid
71101-89-8

trans-4-butylcyclohexane carboxylic acid

A

testosterone ester

testosterone ester

B

testosterone trans-4-n-butylcyclohexanecarboxylate
105165-22-8

testosterone trans-4-n-butylcyclohexanecarboxylate

Conditions
ConditionsYield
With trifluoroacetic anhydride In ethanol; dichloromethane; waterA n/a
B 99.1%
testosterone
58-22-0

testosterone

2-oxocyclopentane-1-carboxylic acid
50882-16-1

2-oxocyclopentane-1-carboxylic acid

17-(5-Oxocyclopentylcarbonyloxy)-Δ4-androstene-3-one
134512-90-6

17-(5-Oxocyclopentylcarbonyloxy)-Δ4-androstene-3-one

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃;99%
testosterone
58-22-0

testosterone

O-(3-carboxy-propyl)hydroxylamine hydrochloride
3106-67-0

O-(3-carboxy-propyl)hydroxylamine hydrochloride

4-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3Z)-ylideneaminooxy]-butyric acid

4-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3Z)-ylideneaminooxy]-butyric acid

Conditions
ConditionsYield
With pyridine at 60℃; for 2.5h;99%
testosterone
58-22-0

testosterone

(2S,3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

(2S,3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

(8R,9S,10R,13S,14S,17S)-17-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

(8R,9S,10R,13S,14S,17S)-17-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
Stage #1: testosterone; (2S,3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran With 4 A molecular sieve; Selectfluor In acetonitrile at 0℃;
Stage #2: With Amberlyst A-21 In acetonitrile
Stage #3: With trimethylammoniomethyl-polymer borohydride In isopropyl alcohol at 20℃;
99%
testosterone
58-22-0

testosterone

testololactone
4416-57-3

testololactone

Conditions
ConditionsYield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 72h; Enzymatic reaction;98%
With Aspergillus tamarii MRC 72400 In N,N-dimethyl-formamide at 24℃; for 120h; Baeyer-Villiger oxidation; Microbiological reaction;58%
With Aspergillus oryzae
Multi-step reaction with 2 steps
1: Penicillium simplicissimum WY134-2; Tween 80 / aq. buffer / 24 h / 30 °C / pH 8 / Enzymatic reaction
2: aq. buffer / 24 h / 40 °C / pH 1
View Scheme
With penicillium vinaceum AM110 for 48h; Enzymatic reaction;100 %Chromat.
testosterone
58-22-0

testosterone

testolactone
968-93-4

testolactone

Conditions
ConditionsYield
With Fusarium oxysporum SC1301 In dimethyl sulfoxide at 30℃; for 15h;98%
With cultures of cylindrocarpone radicola
testosterone
58-22-0

testosterone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

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

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

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 1h;98%
With pyridine at 0℃; Substitution;
testosterone
58-22-0

testosterone

acetyl chloride
75-36-5

acetyl chloride

testosterone acetate
1045-69-8

testosterone acetate

Conditions
ConditionsYield
With potassium fluoride on basic alumina In toluene for 2.5h;98%
With pyridine; acetic anhydride for 4h; Reflux;96%
With immobilized p-toluenesulfonic acid polymer bound macroporous In neat (no solvent) at 100℃; for 0.0416667h; Microwave irradiation; Sealed tube; Green chemistry;33%
With pyridine; acetic anhydride for 4h; Reflux;
testosterone
58-22-0

testosterone

thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside
151767-37-2

thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside

Acetic acid (2R,3S,4R)-3-acetoxy-2-acetoxymethyl-6-((8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R)-3-acetoxy-2-acetoxymethyl-6-((8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yloxy)-tetrahydro-pyran-4-yl ester

Conditions
ConditionsYield
Stage #1: testosterone; thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside With 4 A molecular sieve; Selectfluor In acetonitrile at 0℃;
Stage #2: With Amberlyst A-21 In acetonitrile
Stage #3: With trimethylammoniomethyl-polymer borohydride In isopropyl alcohol at 20℃;
98%
testosterone
58-22-0

testosterone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

17β-(methoxymethoxy)androst-4-en-3-one
26341-28-6

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

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;98%
testosterone
58-22-0

testosterone

acetyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranose
381727-32-8

acetyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranose

testosteryl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranoside

testosteryl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranoside

Conditions
ConditionsYield
With polystyrene-bound silyl triflate In diethyl ether at -50℃; for 3h;97.1%
testosterone
58-22-0

testosterone

Nα-<1,2-bis(p-methoxyphenyl)butyl>-α-aminoacetohydrazide
77579-59-0

Nα-<1,2-bis(p-methoxyphenyl)butyl>-α-aminoacetohydrazide

[1,2-Bis-(4-methoxy-phenyl)-butylamino]-acetic acid [(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylidene]-hydrazide
77579-63-6

[1,2-Bis-(4-methoxy-phenyl)-butylamino]-acetic acid [(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylidene]-hydrazide

Conditions
ConditionsYield
With acetic acid In ethanol Heating;97%
trimethylsilyl formate
18243-21-5

trimethylsilyl formate

testosterone
58-22-0

testosterone

testosteroxytrimethylsilane
5055-42-5

testosteroxytrimethylsilane

Conditions
ConditionsYield
With [Ru(κ1-OAc)(κ2-OAc)(κ3-1,1,1-tris(diphenylphosphinomethyl)ethane)] In acetonitrile at 70℃; for 1h; Inert atmosphere; Schlenk technique;97%
With tris(2-diphenylphosphinoethyl)phosphine; iron(II) acetate In dichloromethane for 2h; Glovebox; Inert atmosphere; Heating;92%
succinic acid anhydride
108-30-5

succinic acid anhydride

testosterone
58-22-0

testosterone

3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid
521-15-3

3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid

Conditions
ConditionsYield
With pyridine at 230℃; for 0.333333h; Sealed tube; Microwave irradiation;96%
With dmap In tetrahydrofuran for 16h; Heating;90%
With pyridine at 125℃;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

testosterone
58-22-0

testosterone

testosteroxytrimethylsilane
5055-42-5

testosteroxytrimethylsilane

Conditions
ConditionsYield
With pyridine In benzene 1.) room temperature, 1 h, 2.) 80 deg C, 2 h;96%
With Aliquat 336; potassium carbonate In Petroleum ether at 60℃; for 4h;63%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

testosterone
58-22-0

testosterone

3-oxoandrost-4-en-17β-yl dodecanoate
59232-78-9

3-oxoandrost-4-en-17β-yl dodecanoate

Conditions
ConditionsYield
With immobilized p-toluenesulfonic acid polymer bound macroporous In neat (no solvent) at 100℃; for 0.0416667h; Microwave irradiation; Sealed tube; Green chemistry;96%
With pyridine Ambient temperature;94%
4-pentynoic acid
6089-09-4

4-pentynoic acid

testosterone
58-22-0

testosterone

Pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
220630-04-6

Pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;96%

58-22-0Upstream product

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