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521-18-6

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  • High purity Dihydrotestosterone (commonly abbreviated to DHT), or 5α-dihydrotestosterone (5α-DHT) with high quality and best price cas:521-18-6

    Cas No: 521-18-6

  • USD $ 1.0-5.0 / Gram

  • 1 Gram

  • 99999 Kilogram/Year

  • Hangzhou Dingyan Chem Co., Ltd
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521-18-6 Usage

Description

Stanolone is well known as dihydrotestosterone (DHT), which is an endogenous androgen sex steroid and hormone. It is an agonist of the androgen receptor (AR). It plays important physiological role in sexual differentiation, maturation of the penis and scrotum, hair, sebum production and development and maintenance of the prostate gland and seminal vesicles. It is mainly used for the treatment of male hypogonadism, androgen deficiency of severe illness, androgen deficiency of ageing and microphallus in infancy.

Chemical Properties

White Crystalline Solid

Originator

Neodrol,Pfizer,US,1953

Uses

Stanolone is a potent androgenic metabolite of testosterone that It is Controlled substance. It was created for the treatment of muscle wasting disease, and osteoporosis. It is a powerful anabolic steroid, which is similar to the body's naturally produced Dihydrotestosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid.

Definition

ChEBI: Stanolone is a 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. It has a role as an androgen, a human metabolite, a Daphnia magna metabolite and a mouse metabolite. It is a 17beta-hydroxy steroid, a 17beta-hydroxyandrostan-3-one and a 3-oxo-5alpha-steroid. It derives from a hydride of a 5alpha-androstane.

Manufacturing Process

A solution of 1.0 g of 3,17-androstandione in 50 ml of methanol and containing 1 g of selenium dioxide, was allowed to remain in an ice-chest overnight. The formed 3,3-dimethoxyandrostan-17-one was not separated. 1 g of solid potassium hydroxide and 2.5 g of sodium borohydride in 2.5 ml of water were added and the mixture allowed to react at room temperature for 24 hours. The solution was then poured into a large excess of water, extracted with methylene chloride, the organic layer dried and evaporated to a residue. The residue was dissolved in ether, and a small amount of selenium removed by filtration. The ether was boiled off and the organic material dissolved in 100 ml of boiling acetone. 25 ml of diluted hydrochloric acid were added, the solution boiled for 5 minutes and then allowed to cool. Upon crystallization, 0.85 g of androstan-17β-ol-3-one was obtained, melting point 175°C to 178°C.

Therapeutic Function

Androgen

General Description

Dihydrotestosterone (Item No. 15874) is an analytical reference standard categorized as an anabolic androgenic steroid. Anabolic steroids, including dihydrotestosterone, have been used to enhance physical performance in athletes. Dihydrotestosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

References

https://en.wikipedia.org/wiki/Dihydrotestosterone#Medical_use Swerdloff, R. S., and C. Wang. "Dihydrotestosterone: a rationale for its use as a non-aromatizable androgen replacement therapeutic agent."Baillieres Clin Endocrinol Metab 12.3(1998):501.

Check Digit Verification of cas no

The CAS Registry Mumber 521-18-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 1 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 521-18:
(5*5)+(4*2)+(3*1)+(2*1)+(1*8)=46
46 % 10 = 6
So 521-18-6 is a valid CAS Registry Number.
InChI:InChI=1/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12?,14-,15-,16-,17-,18-,19-/m0/s1

521-18-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 17β-hydroxy-5α-androstan-3-one

1.2 Other means of identification

Product number -
Other names [3H]-Dihydrotestosterone

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:521-18-6 SDS

521-18-6Synthetic route

17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
58701-44-3

17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20℃; for 3h;97.5%
(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
1046-35-1

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With diiodosilane In chloroform at -42℃; for 0.166667h;95%
(5S,8R,9S,10S,13S,14S,17S)-17-(2-Methoxy-ethoxymethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
91475-95-5

(5S,8R,9S,10S,13S,14S,17S)-17-(2-Methoxy-ethoxymethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile at -20℃; for 0.75h;95%
5α-androstan-17β-ol-3-one tosylhydrazone
68199-33-7

5α-androstan-17β-ol-3-one tosylhydrazone

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 17h; Heating;95%
17β-Hydroxy-5α-androstan-3-one 1,2-Ethanediyl Dithioacetal
37770-14-2

17β-Hydroxy-5α-androstan-3-one 1,2-Ethanediyl Dithioacetal

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With tri(p-bromophenyl)amine; lithium perchlorate; silica gel; sodium hydrogencarbonate In water; acetonitrile for 2h; electrolysis; further reagent: tris(4-bromophenyl)ammoniumyl hexachloroantimonate;91%
With tri(p-bromophenyl)amine; lithium perchlorate In water; acetonitrile Kinetics; Mechanism; cyclovoltammetry;
(5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-17-triethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one
361336-13-2

(5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-17-triethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With polymer-bound NMe3(1+)*F(1-) In methanol at 20℃; for 24h;90%
C33H51NO4
75958-96-2

C33H51NO4

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In tetrahydrofuran Heating;88%
3-ethoxyandrost-3-ene-17-ol

3-ethoxyandrost-3-ene-17-ol

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 60 - 65℃; Solvent; Reagent/catalyst;78%
methyl iodide
74-88-4

methyl iodide

A

Stanolone
521-18-6

Stanolone

B

17β-Hydroxy-4α-methyl-5α-androstan-3-on

17β-Hydroxy-4α-methyl-5α-androstan-3-on

C

4α-Methyl-17β-methoxy-5α-androstan-3-on

4α-Methyl-17β-methoxy-5α-androstan-3-on

D

2,4-Dimethyl-5α-dihydrotestoteron

2,4-Dimethyl-5α-dihydrotestoteron

Conditions
ConditionsYield
With lithium; isopropyl alcohol In tetrahydrofuran; diethyl ether; ammonia at -33℃; for 1.5h;A n/a
B 73%
C n/a
D n/a
C20H32O3

C20H32O3

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;71%
3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene
112251-17-9

3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide at 60℃; for 1h;58%
testosterone
58-22-0

testosterone

A

Stanolone
521-18-6

Stanolone

B

androstanedione
846-46-8

androstanedione

Conditions
ConditionsYield
biochem. proc. with 5α-reductase of Penicillin decumbens;A 10%
B 40%
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436;A 28%
B 37%
testosterone
58-22-0

testosterone

A

Stanolone
521-18-6

Stanolone

B

5β-androstan-17β-ol-3-one
571-22-2

5β-androstan-17β-ol-3-one

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In tetrahydrofuran at 20℃; for 6h;A n/a
B 39%
With hydrogen; palladium In pyridine at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound;
With hydrogen bromide; hydrogen; palladium In tetrahydrofuran at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound;
With 2,2'-azobis(isobutyronitrile); tributylzinc hydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given;
With hydrogen; palladium on activated charcoal In methanolA 54 % Chromat.
B 42 % Chromat.
5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

A

Epiandrosterone
481-29-8

Epiandrosterone

B

Stanolone
521-18-6

Stanolone

C

androstanedione
846-46-8

androstanedione

Conditions
ConditionsYield
at 25℃; for 12h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.01M KOH/t-butanol - water (1:1);A 3%
B 28%
C 30%
testosterone
58-22-0

testosterone

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With 5α-reductase from human prostate or liver; NADPH Equilibrium constant; Kinetics; Mechanism; Vmax, Km, var. of conc. of T, NADPH;
With 1,4-dioxane; diethyl ether; lithium Reagens 4:fluess.NH3;
With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate; NADP; human prostatic 5-α-reductase at 37℃; for 0.5h; Enzyme kinetics;
testosterone
58-22-0

testosterone

A

Stanolone
521-18-6

Stanolone

B

5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With diethyl ether; palladium Hydrogenation;
androstanedione
846-46-8

androstanedione

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With methanol; selenium(IV) oxide anschliessend mit NaBH4 und KOH in H2O und Erwaermen des Reaktionsprodukts in Aceton mit wss.HCl;
Yield given. Multistep reaction;
Multi-step reaction with 3 steps
1: 83 percent / oxalic acid / Heating
2: NaBH4 / methanol / 1 h / 0 deg C to room temp.
3: 95 percent / diiodosilane / CHCl3 / 0.17 h / -42 °C
View Scheme
Multi-step reaction with 2 steps
1: benzene; ethanolic HCl / 75 °C
2: sodium; propanol-(1) / und Erwaermen des Reaktionsprodukts mit wss.-aethanol.HCl
View Scheme
With rabbit 3-hydroxyhexobarbital dehydrogenase (AKR1C29); NADPH In aq. phosphate buffer; ethyl acetate at 37℃; for 0.5h; pH=7.4; Catalytic behavior; Kinetics; Enzymatic reaction;
17β-hydroxy-5α-androstan-3-one-diethylacetal

17β-hydroxy-5α-androstan-3-one-diethylacetal

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With hydrogenchloride
3.3-diethoxy-5α-androstanone-(17)

3.3-diethoxy-5α-androstanone-(17)

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With propan-1-ol; sodium und Erwaermen des Reaktionsprodukts mit wss.-aethanol.HCl;
17β-hydroxy-5α-androstan-3-one semicarbazone
14045-84-2

17β-hydroxy-5α-androstan-3-one semicarbazone

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With sodium acetate; acetic acid; 2-oxo-propionic acid Regeneration;
5alpha-Androstane-3beta,17beta-diol-17-hexahydrobenzoate
20592-39-6

5alpha-Androstane-3beta,17beta-diol-17-hexahydrobenzoate

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
With copper at 210℃; unter vermindertem Druck; und Erwaermen des Reaktionsprodukts mit methanol.Alkalilauge;
With chromium(VI) oxide; acetic acid und Erwaermen des Reaktionsprodukts mit methanol.Alkalilauge;
With aluminum tri-tert-butoxide; toluene; p-benzoquinone und Erwaermen des Reaktionsprodukts mit methanol.Alkalilauge;
testosterone
58-22-0

testosterone

A

Epiandrosterone
481-29-8

Epiandrosterone

B

Stanolone
521-18-6

Stanolone

C

cis-androsterone
53-41-8

cis-androsterone

D

androstanedione
846-46-8

androstanedione

E

5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

F

androstanediol
1852-53-5

androstanediol

Conditions
ConditionsYield
With total testicular homogenate of adult Sprague-Dawley rats treated with 6, des-Gly-NH210>LHRH ethylamide Product distribution; metabolism, <3H>labelled study, further: equine antibovine LH serum (JOAN-5-31-67);
testosterone
58-22-0

testosterone

A

Stanolone
521-18-6

Stanolone

B

Androstenedione
63-05-8

Androstenedione

C

androstanedione
846-46-8

androstanedione

D

androstanediol
1852-53-5

androstanediol

Conditions
ConditionsYield
Product distribution; in vivo metabolism in epididymis of rats, influenced by estradiol-17β or cyproterone acetate, <3H>labeled study;
testosterone
58-22-0

testosterone

A

Stanolone
521-18-6

Stanolone

B

cis-androsterone
53-41-8

cis-androsterone

C

androstanedione
846-46-8

androstanedione

D

5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

E

androstanediol
1852-53-5

androstanediol

Conditions
ConditionsYield
With carbon dioxide; 5α-reductase in testicular cells of adult male Sprague-Dawley rats; oxygen; NADP at 37℃; for 1.5h; Product distribution; Kinetics; <3H>labelled, metabolism with or without 7α-hydroxytestosterone;
testosterone
58-22-0

testosterone

A

Stanolone
521-18-6

Stanolone

B

5β-androstan-17β-ol-3-one
571-22-2

5β-androstan-17β-ol-3-one

C

5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

D

4-androstenediol
1156-92-9

4-androstenediol

E

4-Androstene-3alpha,17beta-diol
1852-61-5

4-Androstene-3alpha,17beta-diol

Conditions
ConditionsYield
With H2SiEt2; Rh-(R,R)-(+)-DIOP for 24h; Product distribution; other reducing agents;
Conditions
ConditionsYield
With 7α-hydroxylase from microsomes of testicular tissue from Wistar rats injected or not intraperitoneally with human chorionic gonadotrophin till 24 h before kill; Krebs Ringer buffer; NADPH In ethanol at 37℃; for 0.25h; Product distribution; Kinetics; <4-14C>labeled study, Michaelis-Menton const. Km, maximal transformation rate Vm;
androstan-3-one
1224-95-9

androstan-3-one

Stanolone
521-18-6

Stanolone

Conditions
ConditionsYield
In water at 25℃; for 240h; biotransformation with cultures of Cephalosporium aphidicola (IMI 68689), other androstanones;70 mg
In ethanol; water at 25℃; for 240h; fermentation with cultures of Cephalosporium aphidicola (IMI 68689); Yield given;
Pregnenolone
145-13-1

Pregnenolone

A

testosterone
58-22-0

testosterone

B

Progesterone
57-83-0

Progesterone

C

Stanolone
521-18-6

Stanolone

D

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

E

Androstenedione
63-05-8

Androstenedione

Conditions
ConditionsYield
With human LH LER; isolated theca of LAK:LVG (SYR) hamsters at 37℃; for 2h; Product distribution; <3H>labeled, metabolism, var. of conc., time of incubation, preincubation, without LH;A 0.00094 mg
B 0.00006 mg
C 0.00017 mg
D 0.00026 mg
E 0.00030 mg
Androstenedione
63-05-8

Androstenedione

A

estradiol
50-28-2

estradiol

B

Estrone
53-16-7

Estrone

C

testosterone
58-22-0

testosterone

D

Stanolone
521-18-6

Stanolone

E

Etiocholanolone
53-42-9

Etiocholanolone

F

cis-androsterone
53-41-8

cis-androsterone

Conditions
ConditionsYield
With carcinoma; gynecomastia; mammary dysplasia at 37℃; for 1.5h; Product distribution; cofactors under 95percent O2: 5percent CO2, <3H>labeled study;
androstanedione
846-46-8

androstanedione

A

Epiandrosterone
481-29-8

Epiandrosterone

B

Stanolone
521-18-6

Stanolone

C

cis-androsterone
53-41-8

cis-androsterone

Conditions
ConditionsYield
With lithium aluminium tetrahydride; divinylbenzene template polymer In tetrahydrofuran Product distribution; Ambient temperature; other steroid ketones; molecular imprinting of solid polymer;
Stanolone
521-18-6

Stanolone

3-oxo-5α-androstan-17β-ol-3-18O
90991-89-2

3-oxo-5α-androstan-17β-ol-3-18O

Conditions
ConditionsYield
With hydrogenchloride; 18O-labeled water In 1,4-dioxane at 75℃; for 24h; sealed tube;100%
Stanolone
521-18-6

Stanolone

acryloyl chloride
814-68-6

acryloyl chloride

Acrylic acid (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester
27953-69-1

Acrylic acid (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;100%
With triethylamine In chloroform at 25℃; for 0.25h;90%
Stanolone
521-18-6

Stanolone

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

17β-Hydroxy-5α-androstan-3-one 1,2-Ethanediyl Dithioacetal
37770-14-2

17β-Hydroxy-5α-androstan-3-one 1,2-Ethanediyl Dithioacetal

Conditions
ConditionsYield
With zeolite HSZ-360 In dichloromethane for 15h; Ambient temperature;100%
Stanolone
521-18-6

Stanolone

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

stanolone 3-Z,E-methyloxime

stanolone 3-Z,E-methyloxime

Conditions
ConditionsYield
With triethylamine; sodium hydroxide In tetrahydrofuran; water at 20 - 60℃; for 5h;100%
Stanolone
521-18-6

Stanolone

androstanedione
846-46-8

androstanedione

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate In dichloromethane for 1.5h; Ambient temperature;99%
With dipyridinium dichromate In dichloromethane at 20℃; for 2h; Inert atmosphere;99%
With N-chloro-succinimide; 4 A molecular sieve; potassium carbonate; N-(phenylthio)-N-(tert-butyl)amine In dichloromethane at 20℃; for 1h;96%
Stanolone
521-18-6

Stanolone

acetic anhydride
108-24-7

acetic anhydride

stanolone acetate
1164-91-6

stanolone acetate

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 6h; Inert atmosphere;99%
With pyridine; dmap at 20℃;
Stanolone
521-18-6

Stanolone

acetyl chloride
75-36-5

acetyl chloride

stanolone acetate
1164-91-6

stanolone acetate

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h; Ambient temperature;98.3%
O-(2-hydroxyethyl)hydroxylamine
3279-95-6

O-(2-hydroxyethyl)hydroxylamine

Stanolone
521-18-6

Stanolone

(Z)-17β-hydroxy-5α-androstan-3-one O-(2-hydroxyethyl)oxime
130132-45-5, 130132-46-6

(Z)-17β-hydroxy-5α-androstan-3-one O-(2-hydroxyethyl)oxime

Conditions
ConditionsYield
With pyridine; acetic acid In ethanol for 0.5h; Heating;97%
Stanolone
521-18-6

Stanolone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
58701-44-3

17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;97%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation;91%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;91%
Stanolone
521-18-6

Stanolone

methyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate
135643-82-2

methyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate

(2α,5α,17β)-17-Hydroxy-2-<<(tetrahydro-2H-pyran-2-yl)oxy>acetyl>androstan-3-one
141507-29-1

(2α,5α,17β)-17-Hydroxy-2-<<(tetrahydro-2H-pyran-2-yl)oxy>acetyl>androstan-3-one

Conditions
ConditionsYield
With hydrogenchloride In N-methyl-acetamide; methanol96%
With sodium hydride 1) DMF, 1 h, rt, 2) DMF, 24 h; Yield given. Multistep reaction;
Stanolone
521-18-6

Stanolone

benzoyl chloride
98-88-4

benzoyl chloride

stanolone benzoate
1057-07-4

stanolone benzoate

Conditions
ConditionsYield
In pyridine at 60℃; for 2h;96%
Stanolone
521-18-6

Stanolone

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(5S,8R,9S,10S,13S,14S,17S)-17-[(tert-butyldiphenylsilyl)oxy]-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one

(5S,8R,9S,10S,13S,14S,17S)-17-[(tert-butyldiphenylsilyl)oxy]-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
With 1H-imidazole; dmap In dichloromethane at 20℃; for 5h;96%
Stanolone
521-18-6

Stanolone

ethylene glycol
107-21-1

ethylene glycol

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
1046-35-1

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 3h; Heating;95%
With toluene-4-sulfonic acid In benzene for 24h; Heating;88%
With pyridine hydrochloride In toluene for 16h; Heating;84%
Stanolone
521-18-6

Stanolone

trisylhydrazine
39085-59-1

trisylhydrazine

17β-hydroxy-5α-androstan-3-one 2,4,6-tri-isopropylbenzenesulphonyl hydrazone
64055-14-7

17β-hydroxy-5α-androstan-3-one 2,4,6-tri-isopropylbenzenesulphonyl hydrazone

Conditions
ConditionsYield
In methanol at 20℃;94%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Stanolone
521-18-6

Stanolone

17β-triflate-5α-androstan-3-one
257619-83-3

17β-triflate-5α-androstan-3-one

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.25h; Condensation;94%
Stanolone
521-18-6

Stanolone

bis-(2-methyl-1H-imidazol-1-yl)methanone
13551-83-2

bis-(2-methyl-1H-imidazol-1-yl)methanone

3-oxo-5α-androst-17β-yl-2'-methyl-1H-imidazole-1-carboxylate
1138159-97-3

3-oxo-5α-androst-17β-yl-2'-methyl-1H-imidazole-1-carboxylate

Conditions
ConditionsYield
In acetonitrile for 70h; Heating;94%
Stanolone
521-18-6

Stanolone

perfluorotoluene
434-64-0

perfluorotoluene

3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene
112251-17-9

3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide for 4h; Heating;93%
Stanolone
521-18-6

Stanolone

methyl chloroformate
79-22-1

methyl chloroformate

17β-methoxycarbonyloxy-5α-androstan-3-one
19291-29-3

17β-methoxycarbonyloxy-5α-androstan-3-one

Conditions
ConditionsYield
In pyridine at 0℃; for 24h;92%
Stanolone
521-18-6

Stanolone

2,3-Dipyridin-2-ylquinoxaline-6-carboxylic acid
17401-74-0

2,3-Dipyridin-2-ylquinoxaline-6-carboxylic acid

17β-(Ol-2,3-bipyridin-2-ylquinoxaline-6-carboxylate)-5α-androstan-3-one

17β-(Ol-2,3-bipyridin-2-ylquinoxaline-6-carboxylate)-5α-androstan-3-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;92%
Stanolone
521-18-6

Stanolone

8-(2-aminoethyl)-2,3,4,5-tetrahydro-1H,4H-11-oxa-3a-aza-benzo-[de]anthracen-10-one hydrochloride

8-(2-aminoethyl)-2,3,4,5-tetrahydro-1H,4H-11-oxa-3a-aza-benzo-[de]anthracen-10-one hydrochloride

(3R,5S,10S,13S,17S)-17-hydroxy-10,13-dimethyl-1,2,2',3',4,5,6,7,8,8',9,9',1',11,12,12',13,13',14,15,16,17-docosahydro-7'H,11'H-spiro[cyclopenta[a]phenanthrene-3,4'-pyrido[3,2,1-ij]pyrido[4',3':4,5]pyrano[2,3-f ]quinolin]-5'(1'H)-one hydrochloride

(3R,5S,10S,13S,17S)-17-hydroxy-10,13-dimethyl-1,2,2',3',4,5,6,7,8,8',9,9',1',11,12,12',13,13',14,15,16,17-docosahydro-7'H,11'H-spiro[cyclopenta[a]phenanthrene-3,4'-pyrido[3,2,1-ij]pyrido[4',3':4,5]pyrano[2,3-f ]quinolin]-5'(1'H)-one hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 48h; Pictet-Spengler Synthesis; Reflux; Sealed tube;92%
With hydrogenchloride In ethanol for 24h; Sealed tube; Reflux;
Stanolone
521-18-6

Stanolone

benzaldehyde
100-52-7

benzaldehyde

17β-hydroxy-2-benzylidene-5-androstan-3-one

17β-hydroxy-2-benzylidene-5-androstan-3-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 3h; Temperature; Claisen-Schmidt Condensation; regioselective reaction;92%
Stanolone
521-18-6

Stanolone

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride
137601-32-2

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride

Angelate Ester of 5α-androstan-17β-ol-3-one
137601-35-5

Angelate Ester of 5α-androstan-17β-ol-3-one

Conditions
ConditionsYield
In toluene at 70℃; for 23h;91%
Stanolone
521-18-6

Stanolone

(5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol
1225-43-0

(5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol

Conditions
ConditionsYield
With acetic acid; zinc In water at 20℃; for 12h;91%
With zinc In acetic acid at 15℃; for 0.25h; ultrasonic irradiation;90%
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 200 - 220℃; for 16h;86%
With acetic acid; zinc In water at 20℃; for 16h;
Stanolone
521-18-6

Stanolone

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

17β-hydroxy-2-(4-fluoro)benzylidene-5-androstan-3-one

17β-hydroxy-2-(4-fluoro)benzylidene-5-androstan-3-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 3h; Claisen-Schmidt Condensation; regioselective reaction;91%
Stanolone
521-18-6

Stanolone

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-oxo-5α-androstan-17β-yl formate
4589-90-6

3-oxo-5α-androstan-17β-yl formate

Conditions
ConditionsYield
With diphenylphosphinopolystyrene; iodine In dichloromethane at 0℃; for 1h;90%

521-18-6Relevant articles and documents

A kinetic analysis of the 5α-reductases from human prostate and liver

Houston,Chisholm,Habib

, p. 355 - 369 (1987)

A kinetic analysis of the 5α-reductases from human liver and prostate is presented. Human prostatic 5α-reductase follows an ordered sequential mechanism in which NADPh binds first followed by testosterone. The order of release of products is DHT followed by NADP+. The apparent K(m) of prostatic 5α-reductase for testosterone is 0.0339 ± 0.006μM, while the apparent K(m) for NADPh is 2.52 ± 0.65μM. Human liver 5α-reductase also follows a sequential mechanism. The apparent K(m) of the liver enzyme is 0.110 ± 0.08μM; the apparent K(m) for NADPH is 6.2 ± 0.6μM. The fact that both the liver and prostatic 5α-reductases have a sequential kinetic mechanism rules out the possibility that the reduction of testosterone to dihydrotestosterone involves an electron transport system as previously proposed.

Jones,Price

, p. 999,1003 (1966)

Significance of the delta 5 and delta 4 steroidogenic pathways in the hamster preovulatory follicle.

Makris,Olsen,Ryan

, p. 641 - 651 (1983)

Isolated hamster granulosa cells and theca from preovulatory follicles were incubated in vitro for 2 and 6 h in the absence/or presence of LH and steroid substrates. The purpose of the experiments was to determine, in theca, the relative activities of the delta 5 and delta 4 pathways under controlled conditions, and to compare the ability of granulosa cells and theca to form progesterone from exogenous pregnenolone. The results of the experiments show that the delta 5 pathway in theca predominates before and up to 2 h after LH stimulation. The delayed effect of LH after 2 h is a switch from delta 5 to delta 4 as the major metabolic pathway. Progesterone formation from exogenous pregnenolone is 7 to 10 times greater in unstimulated granulosa cells than in theca. Acute effects of LH lead to increased conversion of exogenous pregnenolone to progesterone in granulosa cells but not theca. LH does, however, acutely stimulate the thecal conversion of DHEA to androstenedione. The longer term effect of LH in both cell types is to increase pregnenolone conversion to progesterone.

On the photochemical conversion of an alpha, beta-unsaturated gamma, delta-epoxy ketone: 3-oxo-6-alpha, 7-alpha-oxide-17-beta-acetoxy-Delta-androstane

Saboz,Iizuka,Wehrli,Schaffner,Jeger

, p. 1362 - 1371 (1968)

-

Synthetic method of androstenone

-

Paragraph 0087-0089; 0097-0099; 0102-0104; 0107-0109, (2021/05/12)

The invention relates to the field of medicine preparation, in particular to a synthetic method of androstenone. The preparation method comprises the following steps: S100, catalyzing testosterone by a catalyst, and carrying out hydrogenation addition reaction to obtain a compound I; S200, converting a 17-site hydroxyl group of the compound I into a halogen group or a sulfonate group which is easy to leave, so as to obtain a compound II; and S300, subjecting the compound II and alkali to an elimination reaction under the heating condition, namely, a dehalogenation reaction or a desulphonate reaction, so as to obtain androstenone. The synthesis method of androsteneone has the following beneficial effects: the raw materials are cheap and easy to obtain; the process is simple, the route is short, and the requirement on equipment is low; dangerous reagents and operation are avoided, and large-scale industrial production is easy to realize; and isomer impurities are not generated in the synthesis process, and the yield of the target product androsteneone is high.

The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1

Barnard, Lise,Nikolaou, Nikolaos,Louw, Carla,Schiffer, Lina,Gibson, Hylton,Gilligan, Lorna C.,Gangitano, Elena,Snoep, Jacky,Arlt, Wiebke,Tomlinson, Jeremy W.,Storbeck, Karl-Heinz

, (2020/07/21)

Testosterone and its 5α-reduced form, 5α-dihydrotestosterone, were previously thought to represent the only active androgens in humans. However, recent studies have shown that the potent androgen, 11-ketotestosterone, derived from the adrenal androgen precursor, 11β-hydroxyandrostenedione, may in fact serve as the primary androgen in healthy women. Yet, despite recent renewed interest in these steroids, their downstream metabolism has remained undetermined. We therefore set out to investigate the metabolism of 11-ketotestosterone by characterising the 5α- or 5β-reduction commitment step. We show that inactivation of 11-ketotestosterone is predominantly driven by AKR1D1, which efficiently catalyses the 5β-reduction of 11-ketotestosterone, committing it to a metabolic pathway that terminates in 11-ketoetiocholanolone. We demonstrate that 5α-reduction of 11-ketotestosterone is catalysed by SRD5A2, but not SRD5A1, and terminates in 11-ketoandrosterone, but is only responsible for a minority of 11-ketotestosterone inactivation. However, as 11-ketoetiocholanolone is also generated by the metabolism of the glucocorticoid cortisone, 11-ketoandrosterone should be considered a more specific urinary marker of 11-ketotestosterone production.

Purified mCPBA, a Useful Reagent for the Oxidation of Aldehydes

Horn, Alexander,Kazmaier, Uli

, p. 2531 - 2536 (2018/03/21)

Purified mCPBA is a useful reagent for the oxidation of several classes of aldehyde. Although linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α-branched ones undergo Baeyer–Villiger oxidation to formates. α-Branched α,β-unsaturated aldehydes provide enolformates and/or epoxides, which can be saponified to α-hydroxy ketones with shortening of the carbon chain by 1 carbon. Unbranched α,β-unsaturated aldehydes undergo an interesting Baeyer–Villiger oxidation/epoxidation/formate migration/BV oxidation cascade, which results in formyl-protected hydrates with an overall loss of two carbon atoms.

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