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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

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.

Certificates of Analysis (COA)

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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
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
Rosa Draisci et al.
Proteomics, 7(17), 3184-3193 (2007-08-07)
Surveillance of illegal use of steroids hormones in cattle breeding is a key issue to preserve human health. To this purpose, an integrated approach has been developed for the analysis of plasma and urine from calves treated orally with a
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