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Merck
CN

A7505

Sigma-Aldrich

1,4-Androstadiene-3,17-dione

Synonym(s):

1-Dehydroandrostenedione, Androstadienedione

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About This Item

Empirical Formula (Hill Notation):
C19H24O2
CAS Number:
897-06-3
Molecular Weight:
284.39
EC Number:
212-977-2
MDL number:
MFCD00003614
UNSPSC Code:
41116107
PubChem Substance ID:
24891245
NACRES:
NA.77

Key Documents

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biological source

synthetic (organic)

Assay

≥85% (HPLC)

form

powder

drug control

USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

chloroform: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

room temp

SMILES string

[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]4(C)C(=O)CC[C@@]24[H]

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

InChI key

LUJVUUWNAPIQQI-QAGGRKNESA-N

Gene Information

human ... CYP19A1(1588)

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General description

1,4-Androstadiene-3,17-dione is a 17-keto anabolic steroid.

Biochem/physiol Actions

1,4-Androstadiene-3,17-dione is a prohormone that converts to an active steroid through the 17bHSD enzyme. 1,4-Androstadiene-3,17-dione is a metabolite of progesterone.
1,4-Androstadiene-3,17-dione is useful in forming pharmaceutically important steroids. Regio- and stereospecific hydroxylation of 1,4-androstadiene-3,17-dione increases its biological activity. Its derivative is also used to produce high-value bile acids. 1,4-Androstadiene-3,17-dione serves as a precursor for the synthesis of progesterone, testosterone, cortisol, estradiol, cortisone, prednisolone, and prednisone.

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBS8888
SLBQ9122V
SLBP1673V
SLBL9752V
SLBL5442V

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G Gallina et al.
Journal of agricultural and food chemistry, 55(20), 8275-8283 (2007-09-12)
Twenty-six veal calves were split into two groups and fed two milk replacers with a different content of phytosterols for 26 days; then, 14 calves (7 animals from each diet) were kept as controls and 12 calves (6 per diet)
Luca Chiesa et al.
Food chemistry, 188, 473-480 (2015-06-05)
The administration of boldenone and androstadienedione to cattle is forbidden in the European Union, while prednisolone is permitted for therapeutic purposes. They are pseudoendogenous substances (endogenously produced under certain circumstances). The commonly used matrices in control analyses are urine or
K Verheyden et al.
Analytica chimica acta, 586(1-2), 163-170 (2007-03-28)
Current evidence suggests that neo formation of the anabolic steroid boldenone (androsta-1,4-diene-17-ol-3-one) occurs in calves' faecal material, making it difficult to distinguish between illegally administered boldenone and its potential endogenous presence. This strengthens the urgent need to elucidate the pathway
Victoria Giorgi et al.
World journal of microbiology & biotechnology, 35(1), 12-12 (2019-01-04)
Microorganisms were isolated from industrial wool scouring effluents and from the soil adjacent to the wastewater treatment lagoon, both sterols-rich environments, in order to search for novel biocatalysts able to transform cholesterol. The isolates were identified on the basis of
Natasha M Nesbitt et al.
Infection and immunity, 78(1), 275-282 (2009-10-14)
Mycobacterium tuberculosis, the causative agent of tuberculosis, is an intracellular pathogen that shifts to a lipid-based metabolism in the host. Moreover, metabolism of the host lipid cholesterol plays an important role in M. tuberculosis infection. We used transcriptional profiling to
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