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A0887

Sigma-Aldrich

5α-Androstane

Synonym(s):

Etioallocholane

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About This Item

Empirical Formula (Hill Notation):
C19H32
CAS Number:
438-22-2
Molecular Weight:
260.46
EC Number:
207-116-2
MDL number:
MFCD00067600
UNSPSC Code:
12352211
PubChem Substance ID:
24890466
NACRES:
NA.77

Assay

≥99% (HPLC)

Quality Level

200

form

powder

solubility

chloroform: 49-51 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12CC[C@@]3([H])CCCC[C@]3(C)[C@@]1([H])CC[C@]4(C)CCC[C@@]24[H]

InChI

1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14-,15+,16+,17+,18+,19+/m1/s1

InChI key

QZLYKIGBANMMBK-UGCZWRCOSA-N

Gene Information

human ... UGT1A4(54657)

Application

5α-Androstane has been used to treat androgen-dependent and androgen-independent prostate cancer cells (LNCaP and PC-3) to investigate cell proliferation, viability, adhesion and hormone expression.

Other Notes

Serves as the parent steroid skeleton for all androgens, but the hydrocarbon itself is not naturally occurring.

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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Haodong Ji et al.
Marine pollution bulletin, 135, 427-440 (2018-10-12)
Oil degradation by surface-level atmospheric ozone has been largely ignored in the field. To address this knowledge gap, this study investigated the ozonation rate and extent of typical petroleum compounds by simulated surface-level ozone, including total petroleum hydrocarbons (TPHs), n-alkanes
Estrogen and androgen hormone levels modulate the expression of PIWI interacting RNA in prostate and breast cancer
Oner C, et al.
PLoS ONE, 11(7), e0159044-e0159044 (2016)
Kaoru Kobayashi et al.
Drug metabolism and disposition: the biological fate of chemicals, 33(7), 924-929 (2005-04-02)
Constitutive active (or androstane) receptor (CAR, NR1I3), a member of the nuclear receptor family, is a major regulator for induction of cytochrome P450 2B (CYP2B) genes by phenobarbital. Phenobarbital-like inducer, 1,4-bis[2-(3,5-dichloropyridyloxy)]benzene is a potent mouse CAR ligand that has been
Sandra Marini et al.
Life sciences, 80(10), 910-917 (2006-12-13)
Expression and monooxygenase activity of various cytochrome P450 (CYP) enzymes along with constitutive androstane (CAR) and the pregnane X (PXR) receptors were investigated in the brain of control and phenobarbital-treated rabbits (80 mg/kg for 4 days). RT-PCR analysis, using specific
D Blizard et al.
Drug metabolism and disposition: the biological fate of chemicals, 29(6), 781-785 (2001-05-17)
Methoxychlor, a structural analog of the DDT pesticide, was previously shown to induce rat hepatic CYP2B and -3A mRNAs and the corresponding proteins [J Biochem Mol Toxicol 1998;12:315-323], Additionally, methoxychlor was found to activate the constitutive androstane receptor (CAR) system
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