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A7505

Sigma-Aldrich

1,4-Androstadiene-3,17-dione

Synonyme(s) :

1-Dehydroandrostenedione, Androstadienedione

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About This Item

Formule empirique (notation de Hill):
C19H24O2
Numéro CAS:
897-06-3
Poids moléculaire :
284.39
Numéro CE :
212-977-2
Numéro MDL:
MFCD00003614
Code UNSPSC :
41116107
ID de substance PubChem :
24891245
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

200

Essai

≥85% (HPLC)

Forme

powder

Contrôle du médicament

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

Solubilité

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

Température de stockage

room temp

Chaîne SMILES 

[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

Clé InChI

LUJVUUWNAPIQQI-QAGGRKNESA-N

Informations sur le gène

human ... CYP19A1(1588)

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Description générale

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

Actions biochimiques/physiologiques

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.

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Certificats d'analyse (COA)

Lot/Batch Number
SLBS8888
SLBQ9122V
SLBP1673V
SLBL9752V
SLBL5442V

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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
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
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
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