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A2480

Sigma-Aldrich

5α-Androstan-3β-ol

powder

Synonym(s):

3β-Hydroxy-5α-androstane

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About This Item

Empirical Formula (Hill Notation):
C19H32O
CAS Number:
1224-92-6
Molecular Weight:
276.46
EC Number:
214-952-1
MDL number:
MFCD00067608
UNSPSC Code:
51111800
PubChem Substance ID:
329770786
NACRES:
NA.77

biological source

synthetic (organic)

sterility

non-sterile

form

powder

solubility

DMSO: soluble 14 mg/mL at ≤60 °C
H2O: insoluble

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12CC[C@@]3([H])[C@]4([H])CCC[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@H](O)C2

InChI

1S/C19H32O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h13-17,20H,3-12H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChI key

DJTOLSNIKJIDFF-LOVVWNRFSA-N

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Application

5α-Androstan-3β-ol has been used as a cortisone analog to test its effect on the voltage-dependent potassium channel (Kv) current.

Biochem/physiol Actions

mCAR (constitutive androstane receptor) inverse agonist; testosterone metabolite.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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D B Gower et al.
The Journal of steroid biochemistry and molecular biology, 48(4), 409-418 (1994-03-01)
The concentrations of five 16-androstene steroids were determined, by a GC-MS method, in freshly-produced apocrine sweat (adrenaline-induced), in 8 men and 2 women. The ranges of concentrations (nmol/microliter) in apocrine sweat were: 5 alpha-androst-16-en-3-one (5 alpha-A), 0.1-2.0 and 4,16-androstadien-3-one (androstadienone)
Andrea Toell et al.
Journal of cellular biochemistry, 85(1), 72-82 (2002-03-14)
Constitutive androstane receptor (CAR) and pregnane X receptor (PXR) are members of the nuclear receptor superfamily that regulate target gene transcription in a ligand-dependent manner. CAR and PXR have a rather broad, overlapping set of ligands that range from natural
Ping Li et al.
British journal of pharmacology, 158(5), 1322-1329 (2009-08-26)
Potentiating neurosteroids are some of the most efficacious modulators of the mammalian GABA(A) receptor. One of the crucial interactions may be between the C20 ketone group (D-ring substituent at C17) of the neurosteroid, and the N407 and Y410 residues in
Yan Cai et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 15(1), 89-96 (2002-01-23)
Nuclear receptors constitutive androstane receptor (CAR) and pregnane X receptor (PXR) cross talk and serve as xenobiotic sensors to form a safety net against the toxic effects of harmful substances. Retinoid x receptor alpha (RXRalpha) dimerizes with CAR and PXR.
A Kassam et al.
The Journal of biological chemistry, 275(6), 4345-4350 (2000-02-08)
The genes encoding the first two enzymes of the peroxisomal beta-oxidation pathway, acyl-CoA oxidase (AOx) and enoyl-CoA hydratase/3-hydroxyacyl-CoA dehydrogenase (HD), contain upstream cis-acting regulatory regions termed peroxisome proliferator response elements (PPRE). Transcription of these genes is mediated through the binding
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