Boldione

Last updated
Boldione
Boldione.png
Clinical data
Other names1,4-Androstadiene-3,17-dione; 1-Dehydroandrostenedione; androsta-1,4-diene-3,17-dione; ADD
Routes of
administration 		Oral
Identifiers
  • (8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.798 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H24O2
Molar mass 284.399 g·mol−1
3D model (JSmol)
  • O=C\1\C=C/[C@]3(/C(=C/1)CC[C@H]4[C@@H]2CCC(=O)[C@]2(CC[C@H]34)C)C
  • InChI=1S/C19H24O2/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/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
  • Key:LUJVUUWNAPIQQI-QAGGRKNESA-N

Boldione, also known as androstadienedione or 1-dehydroandrostenedione, as well as 1,4-androstadiene-3,17-dione, is an important industrial precursor for various steroid hormones. [1] In the United States the chemical is regulated as a Schedule III Controlled Substance.

Contents

Uses

Androstadienedione is an important industrial-scale precursor for a wide variety of steroid hormones within the estrane and androstane classifications. [1] For example, boldione was recently used in the synthesis of estrogen. [2] [3] [4] Additionally, it has been used in the synthesis of testolactone (via a Baeyer-villiger rearrangement) [5] and of atamestane. [6] Boldione was used in a synthesis of 1-Testosterone. [7]

Preparation

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 from cholesterol by a bacteria in a single step via a simultaneous side-chain cleavage at the C17 position and an alcohol oxidation in the C3 position. [8]

Biosynthesis

The enzyme 3-oxosteroid 1-dehydrogenase produces boldione from androstenedione: [9]

Androstendion.svg
androstenedione
+ electron acceptor
 
 
 
 
Boldione
 
 
 
Boldione.png
boldione
+ reduced acceptor
 

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. [10] 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. [10] Effective January 4, 2010 these three chemicals, including boldione, were classified as Schedule III Controlled Substances and became illegal in the United States. [11]

WADA

Boldione is on the World Anti-Doping Agency's list of prohibited substances, [12] and is therefore banned from use in most major sports.

References

  1. 1 2 3 Sandow J, Scheiffele E, Haring M, Neef G, Prezewowsky K, Stache U (2000). "Hormones". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_089. ISBN   3527306730.
  2. ↑ 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).
  4. ↑ 张峥斌 & 胡明晖, CN105001293 (2017 to Inner Mongolia Junye Biological Pharmaceutical Co ltd, Jiangxi Junye Biological Pharmaceutical Co ltd, Zhejiang Xianju Junye Pharmaceutical Co ltd).
  5. ↑ Bartmanska, A; Dmochowskagladysz, J; Huszcza, E (2005). "Steroids? transformations in culture". Steroids. 70 (3): 193–198. doi:10.1016/j.steroids.2004.11.011
  6. ↑ Prous, J.; Castaer, J.; Drugs Fut 1992, 17, 10, 867.
  7. ↑ Dube Jacques, U.S. patent 3,274,176 (1966 to Sanofi Aventis France).
  8. ↑ Hesselink PG, van Vliet S, de Vries H, Witholt B (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.
  9. ↑ Levy, H. Richard; Talalay, Paul (1959). "Bacterial Oxidation of Steroids". Journal of Biological Chemistry. 234 (8): 2014–2021. doi: 10.1016/S0021-9258(18)69859-X .
  10. 1 2 "Dea Official Testifies to u.s. Senate on Steroids and Health Supplements" (PDF). Archived from the original (PDF) on 2010-10-17. Retrieved 2010-10-20.
  11. ↑ "Rules - 2009". Diversion Control Division. U.S. Department of Justice, Drug Enforcement Agency.
  12. ↑ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency . Retrieved 2019-12-28.
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