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Merck
CN

A9755

Androsterone

≥99%

Synonym(s):

3α-Hydroxy-5α-androstan-17-one, 5α-Androstan-3α-ol-17-one

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About This Item

Empirical Formula (Hill Notation):
C19H30O2
CAS Number:
53-41-8
Molecular Weight:
290.44
UNSPSC Code:
51111800
Beilstein/REAXYS Number:
2217626
MDL number:
MFCD00003618

Key Documents

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InChI

1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1

SMILES string

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

InChI key

QGXBDMJGAMFCBF-HLUDHZFRSA-N

assay

≥99%

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

mp

181-184 °C (lit.)

Biochem/physiol Actions

Anabolic steroid

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
018F0992
120F0437
116H0593
084H0121
075H1217

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X Chai et al.
The Journal of biological chemistry, 272(52), 33125-33131 (1998-01-31)
We report a mouse cDNA that encodes a 317-amino acid short-chain dehydrogenase which recognizes as substrates 9-cis-retinol, 11-cis-retinol, 5alpha-androstan-3alpha,17beta-diol, and 5alpha-androstan-3alpha-ol-17-one. This cis-retinol/androgen dehydrogenase (CRAD) shares closest amino acid similarity with mouse retinol dehydrogenase isozymes types 1 and 2 (86
J Su et al.
Endocrinology, 140(11), 5275-5284 (1999-10-28)
17Beta-hydroxysteroid dehydrogenases (17betaHSDs) convert androgens and estrogens between their active and inactive forms, whereas retinol dehydrogenases catalyze the conversion between retinol and retinal. Retinol dehydrogenases function in the visual cycle, in the generation of the hormone retinoic acid, and some
S H Doss et al.
Archives of pharmacal research, 22(5), 496-501 (1999-11-05)
The reaction of epi-androsterone with cyanoacetyl hydrazine (2) gave the hydrazone derivative 3. The reactivity of 3 towards chemical reagents was studied to give pyridine, thiazole and thiophene derivatives.
N Duijvesteijn et al.
Journal of animal science, 90(8), 2465-2475 (2012-03-01)
In the pig industry, male piglets are surgically castrated early in life to prevent boar taint. Boar taint is mainly caused by androstenone and skatole. Androstenone is a pheromone that can be released from the salivary glands when the boar
Malgorzata Elzbieta Zajda et al.
Acta neurobiologiae experimentalis, 72(1), 65-79 (2012-04-18)
The neurosteroids, dehydroepiandrosterone sulfate (DHEAS) and androsterone, are implicated in drug addictions. We examined their influence on locomotor activity and reward in male Wistar rats, and on steroid and monoamine metabolism in the hippocampus and striatum. In the open field
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