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A3009

Sigma-Aldrich

4-Androsten-11β-ol-3,17-dione

Synonym(s):

11β-Hydroxy-4-androstene-3,17-dione

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About This Item

Empirical Formula (Hill Notation):
C19H26O3
CAS Number:
382-44-5
Molecular Weight:
302.41
MDL number:
MFCD00051131
UNSPSC Code:
51111800
PubChem Substance ID:
24890715
NACRES:
NA.77

Assay

≥98.00% (TLC)

Quality Level

200

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

chloroform: 49-51 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

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

InChI

1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1

InChI key

WSCUHXPGYUMQEX-KCZNZURUSA-N

Biochem/physiol Actions

11β-Hydroxy-4-androstene-3,17-dione is a naturally occurring steroid that is primarily, if not strictly, produced in adrenal tissue. In diseases such as Cushing′s syndrome, adrenal-originated hyperandrogenism, and congenital adrenal hyperplasia, plasma 11β levels are very high. Plasma 11β concentration is very low in congenital 11-hydroxylase deficiency and adrenal insufficiency.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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P Liakos et al.
The Journal of endocrinology, 176(1), 69-82 (2003-01-15)
Transforming growth factor beta1 (TGFbeta1) has been shown to exert strong inhibitory effects on adrenocortical cell steroidogenesis. However, the molecular targets of TGFbeta1 in adrenocortical cells appear to differ between species. Here, we report the first characterization of the regulatory
O Chabre et al.
Endocrinology, 132(1), 255-260 (1993-01-01)
Molecular oxygen is an obligatory substrate of all cytochrome P-450 (cyt P-450) hydroxylases involved in the steroid biosynthetic pathways. However, oxygen-derived free radicals are highly destructive species resulting from cyt P-450-catalyzed steroid hydroxylation reactions. Cells in culture are usually exposed
Fidaa Ibrahim et al.
The Journal of steroid biochemistry and molecular biology, 84(5), 563-568 (2003-05-28)
The plasma concentration of 11beta-hydroxy-4-androstene-3,17-dione (11beta) is very high in 21-hydroxylase deficiency, Cushing's syndrome, and hyperandrogenism of adrenal origin, and very low in congenital 11-hydroxylase deficiency and adrenal insufficiency. Thus, when plasma 4-androstenedione is elevated, it is useful to measure
P Holownia et al.
The Journal of steroid biochemistry and molecular biology, 41(3-8), 875-880 (1992-03-01)
In a longitudinal study of 82 children we found a gradual rise in median plasma concentrations of 11 beta-hydroxyandrostenedione (11 beta-OH-A4) from 2.5 to 6.4 nmol/l during childhood which was similar in both sexes. This could reflect changes in adrenal
E Carmina et al.
Obstetrics and gynecology, 85(6), 971-976 (1995-06-01)
To reevaluate the clinical significance of elevations of adrenal androgens in polycystic ovary syndrome (PCOS). Thirty women with PCOS and ten ovulatory controls were evaluated. Serum dehydroepiandrosterone (DHEA) sulfate and 11 beta-hydroxyandrostenedione were measured before and after 3 and 6
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