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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN9897
MKCN9896
MKCK1109
MKCJ6032
MKCG6171

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Scott S Auerbach et al.
Drug metabolism and disposition: the biological fate of chemicals, 35(3), 428-439 (2006-12-30)
The constitutive androstane receptor (CAR; NR1I3) regulates the expression of genes involved in xenobiotic metabolism. Alternative splicing of the human CAR gene yields an array of mRNAs that encode structurally diverse proteins. One form of CAR, termed CAR2, contains an
Li-Hua Huang et al.
Steroids, 77(5), 367-374 (2011-12-21)
The preparation of novel steroidal heterocycles containing the 7-aryl-substituted 1,2,4-triazolo[1,5-a]pyrimidine moiety fused to the 16,17-positions of the steroid nucleus is described. The Aldol reaction of 4-aza-androst-3,17-dione (1a) and dehydroepiandrosterone (DHEA, 1b) with aromatic aldehydes was catalyzed by KF/Al(2)O(3) to give
Yaping Pan et al.
ACS chemical biology, 7(10), 1641-1646 (2012-07-19)
The Kv1 family voltage-dependent K(+) channels are essential for termination of action potentials in neurons and myocytes. These channels form a stable complex with their beta subunits (Kvβ), some of which inhibit channel activity. Cortisone potentiates Kv1 channel by binding
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
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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