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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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E Carmina et al.
Fertility and sterility, 58(1), 148-152 (1992-07-01)
To determine if the ratio of serum androstenedione (A):11 beta-hydroxyandrostenedione (OHA) would be helpful in differentiating adrenal from ovarian hyperandrogenism. Prospective study of outpatients being evaluated for hyperandrogenism. Normal women (n = 27), those with hyperandrogenic chronic anovulation (n =
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
R Huerta et al.
Fertility and sterility, 72(6), 996-1000 (1999-12-11)
To determine the sensitivity of 11beta-hydroxyandrostenedione (11-OHA4) and delta5-androstenediol (ADIOL) as markers of excessive adrenal androgen production. Prospective study. Academic medical centers. Thirteen women with untreated 21-hydroxylase-deficient nonclassic adrenal hyperplasia (NCAH) and 18 healthy, eumenorrheic, nonhirsute controls matched for age
F Z Stanczyk et al.
American journal of obstetrics and gynecology, 165(6 Pt 1), 1837-1842 (1991-12-01)
To determine whether the adrenal androgen 11 beta-hydroxyandrostenedione is a more sensitive and specific marker than dehydroepiandrosterone sulfate, we compared these serum androgens in 81 women with anovulatory hyperandrogenism before treatment, after corticotropin and corticotropin-releasing-factor stimulation, and after short- and
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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