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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)

Quality Level

100

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.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

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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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)
Jorge Luiz Vieira Dos Anjos et al.
International journal of pharmaceutics, 345(1-2), 81-87 (2007-06-30)
The interaction of a potent percutaneous penetration enhancer, 1,8-cineole, with the stratum corneum (SC) and DPPC membranes was investigated by electron paramagnetic resonance spectroscopy (EPR) of spin-labeled analogs of stearic acid (5-DSA) and androstanol (ASL). The EPR spectra of lipid
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
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
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.
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