Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

A7505

Sigma-Aldrich

1,4-Androstadiene-3,17-dione

Synonym(s):

1-Dehydroandrostenedione, Androstadienedione

Sign Into View Organizational & Contract Pricing
All Photos(3)

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

biological source

synthetic (organic)

Quality Level

200

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)

Looking for similar products? Visit Product Comparison Guide

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.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Wei Wei et al.
Applied and environmental microbiology, 76(13), 4578-4582 (2010-05-11)
3-Ketosteroid-Delta(1)-dehydrogenase, KsdD(M), was identified by targeted gene disruption and augmentation from Mycobacterium neoaurum NwIB-01, a newly isolated strain. The difficulty of separating 4-androstene-3,17-dione (AD) from 1,4-androstadiene-3,17-dione (ADD) is a key bottleneck to the microbial transformation of phytosterols in industry. This
Rituraj Batth et al.
Plants (Basel, Switzerland), 9(9) (2020-09-10)
Steroids are a group of organic compounds that include sex hormones, adrenal cortical hormones, sterols, and phytosterols. In mammals, steroid biosynthesis starts from cholesterol via multiple steps to the final steroid and occurs in the gonads, adrenal glands, and placenta.
M V Donova et al.
Microbiology (Reading, England), 153(Pt 6), 1981-1992 (2007-05-29)
Modified beta-cyclodextrins have been shown previously to enhance sterol conversion to 4-androstene-3,17-dione (AD) and 1,4-androstadiene-3,17-dione (ADD) by growing Mycobacterium spp. The enhancement effect was mainly attributed to steroid solubilization by the formation of inclusion complexes with modified cyclodextrins. In this
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service