Boldione

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Boldione
Boldione.png
Names
IUPAC name
(8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
Other names
1,4-Androstadiene-3,17-dione; Androsta-1,4-diene-dione, Androsta-1,4-diene,3,17-dione
Identifiers
897-06-3
ChemSpider 12893
Jmol 3D model Interactive image
PubChem 13472
Properties
C19H24O2
Molar mass 284.39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Boldione, also commonly known as androstadienedione, is an important industrial precursor for various steroid hormones.[1] In the United States the chemical is regulated as a Schedule III Controlled Substance.

Uses[edit]

Androstadienedione is an important industrial-scale precursor for a wide variety of steroid hormones within the estrane and androstane classifications.[1]

Preparation[edit]

Androstadienedione is obtained in high yield from both plant and animal sterols by biotransformation.[1] The chemical is a common byproduct derived from other processes (e.g. vegetable oil deodorization and the production of lanolin from wool processing). The product is produced in a single step via a simultaneous side-chain cleavage at the 17th position and an alcohol oxidation in the 3rd position.[2]

Regulation[edit]

United States[edit]

In 2004 the United States Congress passed the Anabolic Steroid Control Act of 2005 which placed 36 steroids and over the counter pro-hormones into schedule III of the Controlled Substances Act. In this legislation boldenone was classified as a controlled substance and boldione remained legal.[3] 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.[3] Effective January 4, 2010 these three chemicals, including boldione, were classified as Schedule III Controlled Substances and became illegal in the United States.[4]

References[edit]

  1. ^ a b c Sandow, Jürgen; Scheiffele, Ekkehard; Haring, Michael; Neef, Günter; Prezewowsky, Klaus; Stache, Ulrich (2000). "Hormones". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_089. ISBN 3527306730. 
  2. ^ Hesselink, Paul G.M.; Vliet, Steven van; Vries, Harrie de; Witholt, Bernard (1989). "Optimization of steroid side chain cleavage by Mycobacterium sp. in the presence of cyclodextrins". Enzyme and Microbial Technology 11 (7): 398–404. doi:10.1016/0141-0229(89)90133-6. 
  3. ^ a b http://www.justice.gov/dea/pubs/cngrtest/ct092909.pdf
  4. ^ http://www.deadiversion.usdoj.gov/fed_regs/rules/2009/fr1204.htm