846-48-0 Usage
Description
Boldenone is an anabolic androgenic steroid that serves as the chemical precursor to its prodrug, boldenone undecylenate. It is primarily used as a steroid for animals, particularly horses and cattle, to improve their weight, hair coat, appetite, and general physical condition. Additionally, it is utilized as an illegal doping agent for human athletes and is regulated as a Schedule III compound in the United States.
Used in Veterinary Medicine:
Boldenone is used as a performance-enhancing steroid for horses and cattle under brand names such as Equipoise. It is injected to improve the weight, hair coat, appetite, and general physical condition of animals affected by disease, anorexia, or overwork.
Used in Human Athletics:
Boldenone is used as an illegal doping agent by human athletes seeking to enhance their physical performance. As a derivative of testosterone, it retains its anabolic strength while exhibiting reduced androgenic effects.
Used in Research and Forensic Applications:
Boldenone is also utilized as an analytical reference standard for research purposes, particularly in the development of detection methods and forensic analysis related to its use as a controlled substance and anabolic steroid.
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
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
846-48-0Relevant 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
experimental part, 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.