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846-48-0

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846-48-0 Usage

Description

Different sources of media describe the Description of 846-48-0 differently. You can refer to the following data:
1. Boldenone is the chemical precursor of its endecylenate ester prodrug boldenone undecylenate – which is used extensively as a steroid for animals, mainly horses and cattle, under the brand name Equipoise, among others. For this application, it is injected to improve the weight, hair coat, appetite, and general physical condition of horses affected by disease, anorexia, or overwork. It is also used as an illegal doping agent for human athletes. As a derivative of testosterone, it retains its anabolic strength, but exhibits reduced androgenic effects.
2. Boldenone (Item No. 15432) is an analytical reference standard categorized as an anabolic androgenic steroid. Anabolic steroids, including boldenone, have been used to enhance physical performance in athletes. Boldenone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Sources

https://en.wikipedia.org/wiki/Boldenone_undecylenate https://en.wikipedia.org/wiki/Boldenone https://www.drugs.com/vet/equipoise.html https://www.steroidal.com/steroid-profiles/equipoise/ https://www.evolutionary.org/equipoise-boldenone-undecylenate

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 846-48-0 differently. You can refer to the following data:
1. Boldenone is an anabolic steroid. Controlled substance.
2. Controlled substance. Anabolic steroid

Definition

ChEBI: An 3-oxo-Delta1,Delta4-steroid substituted by an oxo group at position 3 and a beta-hydroxy group at position 17. It is an anabolic androgenic steroid that has been eveloped for veterinary use.

Synthesis

Boldenone is obtained by reacting Testosterone with tert-butyldimethylsilyl chloride in the presence of DDQ. Experimental Procedure: 29.0 g Testosterone was dissolved in 220 ml dioxan/THF 8:2 and cooled to 0°C on ice. After cooling down a solution of tert-butyldimethylsilyl chloride (46.0 g in 100 ml dioxan/THF 8:2) was added dropwise and stirred for 90 min at 0°C. Then a suspension of 32.0 g of DDQ in 200 ml dioxan/THF 8:2 was added in 4 equal portions over a period of 4 h. The reaction mixture was stirred for additional 12 h within coming from 0°C to room temperature. The resulting suspension was then filtered over Celite and rinsed with 300 ml THF. The filtrate was evaporated and brown oil was obtained. The oil was diluted in 1500 ml DCM and washed with 500 ml of 5% aqueous sodium hydroxide. The yellow organic phase was washed with 400 ml water and 400 ml saturated sodium chloride solution, before drying over magnesium sulfate. After evaporation, the crude product was chromatographed on silica gel by using hexane-ethyl acetate (3:7), followed by a recrystallization in ethyl acetate. 16.50 g of Boldenone was obtained as an amber solid (58%).

Check Digit Verification of cas no

The CAS Registry Mumber 846-48-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,4 and 6 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 846-48:
(5*8)+(4*4)+(3*6)+(2*4)+(1*8)=90
90 % 10 = 0
So 846-48-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H26O2/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/h7,9,11,14-17,21H,3-6,8,10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

846-48-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name boldenone

1.2 Other means of identification

Product number -
Other names 1,2-didehydrotestosterone

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:846-48-0 SDS

846-48-0Synthetic route

testosterone
58-22-0

testosterone

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 20℃; for 40h;74%
With selenium(IV) oxide
With selenious acid
With old yellow enzyme from Geobacillus kaustophilus at 70℃; for 48h; pH=7; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;
mit Hilfe von Corynebacterium simplex;
Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
for 336h; Rhodotorula mucilaginosa;64%
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436;3%
cholesterol
57-88-5

cholesterol

A

testosterone
58-22-0

testosterone

B

Androstenedione
63-05-8

Androstenedione

C

Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

D

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

E

2-[(8S,9S,10R,13S,14S)-10,13-Dimethyl-3-oxo-3,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-(17Z)-ylidene]-propionic acid methyl ester
79694-52-3

2-[(8S,9S,10R,13S,14S)-10,13-Dimethyl-3-oxo-3,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-(17Z)-ylidene]-propionic acid methyl ester

F

22-hydroxy-23,24-bisnor-1,4-choladien-3-one
71658-22-5

22-hydroxy-23,24-bisnor-1,4-choladien-3-one

Conditions
ConditionsYield
With Mycobacterium sp. CCM 3529 Product distribution;A 0.01 g
B 0.03 g
C 51%
D 0.06 g
E n/a
F 0.38 g
Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

A

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

B

11α,17β-dihydroxyandrosta-1,4-dien-3-one
30915-20-9

11α,17β-dihydroxyandrosta-1,4-dien-3-one

Conditions
ConditionsYield
With phosphate buffer; Beauveria sp. culture at 28℃; for 24h;A 38%
B 46%
With phosphate buffer; Beauveria sp. culture at 28℃; for 24h; Yield given. Yields of byproduct given;
Epiandrosterone
481-29-8

Epiandrosterone

A

testosterone
58-22-0

testosterone

B

3β,11α-dihydroxy-5α-androstan-17-one
25848-75-3

3β,11α-dihydroxy-5α-androstan-17-one

C

3beta-7alpha-Dihydroxy-5alpha-androstane-17-one
25848-68-4

3beta-7alpha-Dihydroxy-5alpha-androstane-17-one

D

3beta-7beta-Dihydroxy-5alpha-androstane-17-one
25848-69-5

3beta-7beta-Dihydroxy-5alpha-androstane-17-one

E

1α,3β-dihydroxy-5α-androstan-17-one
2260-01-7

1α,3β-dihydroxy-5α-androstan-17-one

F

Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

G

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

I

5α-androst-1-ene-3,17-dione
571-40-4

5α-androst-1-ene-3,17-dione

J

6β-hydroxy-4-androstene-3,17-dione
63-00-3

6β-hydroxy-4-androstene-3,17-dione

Conditions
ConditionsYield
With malt extract; disodium hydrogenphosphate; calcium(II) chloride dihydrate; magnesium(II) chloride hexahydrate; strontium (III) chloride hexahydrate; potassium chloride; boric acid; sodium hydrogencarbonate; sodium sulfate; sodium chloride; potassium bromide; potassium hydroxide In water; N,N-dimethyl-formamide at 32℃; for 168h; pH=8; Enzymatic reaction;A 2%
B 2%
C 2%
D 3%
E 5%
F 5%
G 3%
H 2%
I 2%
J 32%
2,4,6-trimethyl-pyridine
108-75-8

2,4,6-trimethyl-pyridine

2α,4α-dibromo-17β-hydroxy-5α-androstan-3-one
119369-73-2

2α,4α-dibromo-17β-hydroxy-5α-androstan-3-one

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

A

testosterone
58-22-0

testosterone

B

Androstenedione
63-05-8

Androstenedione

C

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
at 25℃; for 72h; stereoselective reduction in the biotransformation by cell suspension cultures of Marchantia Polymorpha, other androsterone derivative;
With Mycobacterium sp. No. 22 for 24h; Microbiological reaction;A n/a
B n/a
C 0.5 g
With unidentified fungal species isolated from grinded corn In water at 37℃; for 1h; pH=7; aq. phosphate buffer; Microbiological reaction; Enzymatic reaction;
Progesterone
57-83-0

Progesterone

A

testosterone
58-22-0

testosterone

B

pregna-1,4-diene-3,20-dione
1162-54-5

pregna-1,4-diene-3,20-dione

C

Androstenedione
63-05-8

Androstenedione

D

testosterone acetate
1045-69-8

testosterone acetate

E

11-alpha-hydroxyprogesterone
80-75-1

11-alpha-hydroxyprogesterone

F

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
With immobilized spores of Aspergillus ochraceus; Tris-maleate buffer at 30℃; for 48h; Product distribution; Mechanism; various water activity of the biocatalysts;
17β-acetoxy-androstadien-(1.4)-one-(3)

17β-acetoxy-androstadien-(1.4)-one-(3)

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
With potassium hydroxide
2α.4α-dibromo-17β-hydroxy-androstanone-(3)

2α.4α-dibromo-17β-hydroxy-androstanone-(3)

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
With 2,3,5-trimethyl-pyridine
With Potassium benzoate; toluene; butan-1-ol Erhitzen des Reaktionsprodukts unter 6 Torr auf 220-230grad;
Androstenedione
63-05-8

Androstenedione

A

testosterone
58-22-0

testosterone

B

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction
2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction
View Scheme
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
With zinc In tetrahydrofuran Heating;96%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

testolactone
968-93-4

testolactone

Conditions
ConditionsYield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 96h; Enzymatic reaction;90%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

17β-O-tert-butyldimethylsilylandrosta-1,4-dien-3-one
102054-23-9

17β-O-tert-butyldimethylsilylandrosta-1,4-dien-3-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;89%
With 1H-imidazole In N,N-dimethyl-formamide for 4.5h; Ambient temperature;83%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

acetic acid
64-19-7

acetic acid

17a-acetoxy-androst-1,4-dien-3-one

17a-acetoxy-androst-1,4-dien-3-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 40℃; for 0.5h;83%
formic acid
64-18-6

formic acid

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 40℃; for 0.5h;82%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester
21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

methyl (androsta-1,4-dien-17β-ol-3-one)-17-O-2,3,4-tri-O-acetyl-β-D-glucuronate
1177368-54-5

methyl (androsta-1,4-dien-17β-ol-3-one)-17-O-2,3,4-tri-O-acetyl-β-D-glucuronate

Conditions
ConditionsYield
With cadmium(II) carbonate In toluene for 6h; Koenigs-Knorr synthesis; Heating;80%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

benzoic acid
65-85-0

benzoic acid

3-oxoandrosta-1,4-dien-17α-yl benzoate
150054-81-2

3-oxoandrosta-1,4-dien-17α-yl benzoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 40℃; for 0.5h;80%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

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

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

3-oxoandrosta-1,4-dien-17β-yl-2'-methyl-1H-imidazole-1-carboxylate
1138159-98-4

3-oxoandrosta-1,4-dien-17β-yl-2'-methyl-1H-imidazole-1-carboxylate

Conditions
ConditionsYield
In dichloromethane for 28h; Heating;73%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

2-(1,1-Dimethyl-prop-2-ynylperoxy)-2-methyl-pentane
98406-40-7

2-(1,1-Dimethyl-prop-2-ynylperoxy)-2-methyl-pentane

Methacryloyl chloride
920-46-7

Methacryloyl chloride

3,17β-dimethacryloyloxy-3-(3-methyl-3-tert-pentylperoxybut-1-ynyl)-androsta-1,4-diene

3,17β-dimethacryloyloxy-3-(3-methyl-3-tert-pentylperoxybut-1-ynyl)-androsta-1,4-diene

Conditions
ConditionsYield
Stage #1: 2-(1,1-Dimethyl-prop-2-ynylperoxy)-2-methyl-pentane With n-butyllithium In hexane at -40 - -20℃; for 1h;
Stage #2: 1-dehydrotestosterone In diethyl ether; hexane at 15 - 20℃; for 18h;
Stage #3: Methacryloyl chloride In diethyl ether; hexane at 0 - 20℃; for 19h;
66%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

Conditions
ConditionsYield
for 336h; Rhodotorula mucilaginosa;54%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

A

14α,17β-dihydroxyandrosta-1,4-dien-3-one
58105-34-3

14α,17β-dihydroxyandrosta-1,4-dien-3-one

B

6β,17β-dihydroxyandrosta-1,4-dien-3-one

6β,17β-dihydroxyandrosta-1,4-dien-3-one

Conditions
ConditionsYield
With fungus Cephalosporium aphidicola In ethanol for 120h; hydroxylation;A 2%
B 48%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

thioacetic acid
507-09-5

thioacetic acid

A

1α-acetylthio-17β-hydroxy-4-androsten-3-one
99371-90-1

1α-acetylthio-17β-hydroxy-4-androsten-3-one

B

1α-acetylthio-17β-hydroxy-4-androsten-3-one 17-acetat
116104-58-6

1α-acetylthio-17β-hydroxy-4-androsten-3-one 17-acetat

Conditions
ConditionsYield
In chloroform at 40℃; for 24h;A 47%
B 16%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

A

[1-2H]4-methylestra-1,3,5(10)-trien-17β-ol

[1-2H]4-methylestra-1,3,5(10)-trien-17β-ol

B

[1α-2H]testosterone

[1α-2H]testosterone

C

[1α,3ξ-2H2]androst-4-ene-3ξ,17β-diol
898529-69-6

[1α,3ξ-2H2]androst-4-ene-3ξ,17β-diol

Conditions
ConditionsYield
With lithium aluminium deuteride In tetrahydrofuran for 0.25h; Heating;A 31%
B 18%
C 28%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

A

[1α-2H]testosterone

[1α-2H]testosterone

B

[1α,3ξ-2H2]androst-4-ene-3ξ,17β-diol
898529-69-6

[1α,3ξ-2H2]androst-4-ene-3ξ,17β-diol

Conditions
ConditionsYield
With sodium borodeuteride In tetrahydrofuran for 0.25h; Heating;A 15%
B 30%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

thiophenol
108-98-5

thiophenol

1α-phenylthio-17β-hydroxyandrost-4-ene-3-one

1α-phenylthio-17β-hydroxyandrost-4-ene-3-one

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 3h; Heating;20%
1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

11α,17β-dihydroxyandrosta-1,4-dien-3-one
30915-20-9

11α,17β-dihydroxyandrosta-1,4-dien-3-one

Conditions
ConditionsYield
for 72h; Rhizopus arrhizus ATCC 11145;13%
quinoline
91-22-5

quinoline

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
at 370 - 390℃;
at 370 - 390℃;
butanoic acid anhydride
106-31-0

butanoic acid anhydride

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

17β-butyryloxy-androsta-1,4-dien-3-one

17β-butyryloxy-androsta-1,4-dien-3-one

Conditions
ConditionsYield
With pyridine
tetralin
119-64-2

tetralin

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
at 370 - 390℃;
at 370 - 390℃;
thioacetic acid
507-09-5

thioacetic acid

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

1α-acetylthio-17β-hydroxy-4-androsten-3-one
99371-90-1

1α-acetylthio-17β-hydroxy-4-androsten-3-one

pentanoic anhydride
2082-59-9

pentanoic anhydride

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

17β-valeryloxy-androsta-1,4-dien-3-one

17β-valeryloxy-androsta-1,4-dien-3-one

Conditions
ConditionsYield
at 130℃;
1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
at 370 - 390℃;
at 370 - 390℃;
9,10-dihydrophenanthrene
776-35-2

9,10-dihydrophenanthrene

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

A

estradiol
50-28-2

estradiol

B

4-methyl-estratriene-(1.3.5(10))-diol-(1.17β)
3597-39-5

4-methyl-estratriene-(1.3.5(10))-diol-(1.17β)

Conditions
ConditionsYield
at 390℃;

846-48-0Relevant articles and documents

Microbial transformation of epiandrosterone by Aspergillus sydowii

Yildirim, Kudret,Kuru, Ali

, p. 718 - 721 (2016/12/30)

Incubation of epiandrosterone with Aspergillus sydowii MRC 200653 afforded ten metabolites. The fungal dehydrogenation of epiandrosterone is reported for the first time. The formation of the major metabolite, 6?-hydroxyandrost-4-ene-3,17-dione, involved first dehydrogenation to give a 4-ene and then hydroxylation at C-6?. Small amounts of the substrate were hydroxylated at C-1α, C-7α, C-7β and C-11α.

Endogenous boldenone-formation in cattle: Alternative invertebrate organisms to elucidate the enzymatic pathway and the potential role of edible fungi on cattle's feed

Verheyden,Noppe,Zorn,Van Immerseel,Bussche, J. Vanden,Wille,Bekaert,Janssen,De Brabander,Vanhaecke

, p. 161 - 170 (2011/03/19)

Although β-boldenone (bBol) used to be a marker of illegal steroid administration in calves, its endogenous formation has recently been demonstrated in these vertebrates. However, research on the pathway leading to bBol remains scarce. This study shows the usefulness of in vivo invertebrate models as alternatives to vertebrate animal experiments, using Neomysis integer and Lucilia sericata. In accordance with vertebrates, androstenedione (AED) was the main metabolite of β-testosterone (bT) produced by these invertebrates, and bBol was also frequently detected. Moreover, in vitro experiments using feed-borne fungi and microsomes were useful to perform the pathway from bT to bBol. Even the conversion of phytosterols into steroids was shown in vitro. Both in vivo and in vitro, the conversion of bT into bBol could be demonstrated in this study. Metabolism of phytosterols by feed-borne fungi may be of particular importance to explain the endogenous bBol-formation by cattle. To the best of our knowledge, it is the first time the latter pathway is described in literature.

Reduction of steroidal ketones with amine - Boranes

Leontjev,Vasiljeva,Pivnitsky

, p. 703 - 708 (2007/10/03)

Complexes of secondary amines with borane, R2NH·BH 3, surpass sodium borohydride as reducing agents for saturated and unsaturated steroidal 3-, 12-, 17-, and 20-ketones as regards chemo- and regioselectivity and mildness of the reaction conditions. In the case of 12-ketones, stereoselectivity is also improved.

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