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A7505

Sigma-Aldrich

1,4-Androstadiene-3,17-dione

Sinónimos:

1-Dehydroandrostenedione, Androstadienedione

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About This Item

Fórmula empírica (notación de Hill):
C19H24O2
Número de CAS:
897-06-3
Peso molecular:
284.39
Número CE:
212-977-2
Número MDL:
MFCD00003614
Código UNSPSC:
41116107
ID de la sustancia en PubChem:
24891245
NACRES:
NA.77

origen biológico

synthetic (organic)

Ensayo

≥85% (HPLC)

Formulario

powder

control farmacológico

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

solubilidad

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

temp. de almacenamiento

room temp

cadena 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

Clave InChI

LUJVUUWNAPIQQI-QAGGRKNESA-N

Información sobre el gen

human ... CYP19A1(1588)

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Descripción general

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

Acciones bioquímicas o fisiológicas

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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Certificados de análisis (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.
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
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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