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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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B Bélanger et al.
Steroids, 58(1), 29-34 (1993-01-01)
In order to gain a better understanding of adrenal steroid production in guinea pigs, adrenocorticotropin (ACTH) was administered to castrated adult guinea pigs and a series of C-21 and C-19 steroid levels were determined in both adrenals and plasma over
J E Cavaco et al.
The American journal of physiology, 275(6 Pt 2), R1793-R1802 (1998-12-09)
The effects of sex steroids on spermatogenesis and testicular androgen secretion were studied in juvenile (spermatogonia present in testes) African catfish. Fish were implanted with Silastic pellets containing 11-ketotestosterone (KT), 11beta-hydroxyandrostenedione (OHA), androstenetrione (OA), androstenedione (A), testosterone (T), 5alpha-dihydrotestosterone (DHT)
Martín Blasco et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(14-15), 1509-1515 (2009-04-17)
A simple and novel HPLC-MS method for the simultaneous quantification of testosterone, 11-ketotestosterone, and 11beta-hydroxyandrostenedione in fish serum was developed and validated. Separation was achieved on a C-18 column using a water-acetonitrile mobile-phase with a cycle time of 12 min.
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
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
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