boldione

Also known as ADD, ADT, 1-Dehydroandrostenedione, Androstadienedione, 1,4-Androstadiene-3,17-dione, ANDROSTA-1,4-DIENE-3,17-DIONE

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. In the United States the chemical is regulated as a Schedule III Controlled Substance.

Chemical data

Formula: C19H24O2
Molecular weight: 284.4 g/mol
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
SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)C=C[C@]34C
InChIKey: LUJVUUWNAPIQQI-QAGGRKNESA-N
XLogP: 3
Polar surface area: 34.1 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 284.178

Show 4 more facts

chemical formula: C₁₉H₂₄O₂
isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)C=C[C@]34C
canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=CC(=O)C=CC34C
found in taxon: Aglaia rubiginosa

Sources (3)

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Encyclopedic overview

7 sections

Contents

Uses
Preparation
Biosynthesis
Regulation
United States
WADA
References

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

Excerpted from Wikipedia’s “boldione” article, available under the CC BY-SA 4.0 licence.

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