Boldione

Uses

Androstadienedione is an important industrial-scale precursor for a wide variety of steroid hormones within the estrane and androstane classifications. Additionally, it has been used in the synthesis of testolactone (via a Baeyer-villiger rearrangement) and of atamestane.

Preparation

Androstadienedione is obtained in high yield from both plant and animal sterols by biotransformation.

Biosynthesis

The enzyme 3-oxosteroid 1-dehydrogenase produces boldione from androstenedione:

Regulation

United States

In 2004 the United States Congress passed the Anabolic Steroid Control Act of 2005 which placed 36 steroids and over-the-counter prohormones into schedule III of the Controlled Substances Act. In this legislation boldenone was classified as a controlled substance and boldione remained legal. In April 2008 the United States Drug Enforcement Administration published an "Initial Notice of Proposed Rulemaking" concerning the scheduling of three anabolic substances: boldione, desoxymethyltestosterone, and dienedione. In 2008, at the time of the proposal, these three substances were listed as ingredients in more than 58 dietary supplements which were available for purchase over the counter. Effective January 4, 2010 these three chemicals, including boldione, were classified as Schedule III Controlled Substances and became illegal in the United States.

WADA

Boldione is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports.

References

References

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2. For example, boldione was recently used in the synthesis of estrogen.系祖斌, et al. CN116063366 (2023 to Hubei Tongtong Steroidal Drug Research Institute Co ltd).
3. 田伟生, 史勇 & 汪昀, CN107602650 (2018 to Shanghai Institute of Organic Chemistry of CAS).
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