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Merck
CN

A7755

5α-Androstane-3α,17β-diol

Synonym(s):

3α,17β-Dihydroxy-5α-androstane, Dihydroandrosterone

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About This Item

Empirical Formula (Hill Notation):
C19H32O2
CAS Number:
1852-53-5
Molecular Weight:
292.46
NACRES:
NA.77
PubChem Substance ID:
24278236
UNSPSC Code:
51111800
EC Number:
217-447-4
MDL number:
MFCD00003676
Assay:
≥98% (TLC)
Form:
powder
Quality level:
200

Key Documents

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InChI

1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1

InChI key

CBMYJHIOYJEBSB-KHOSGYARSA-N

SMILES string

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

assay

≥98% (TLC)

form

powder

drug control

USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

technique(s)

toxicology assay: suitable

solubility

methanol: 19.60-20.40 mg/mL, clear, colorless

storage temp.

room temp

Quality Level

200

Gene Information

rat ... Ar(24208)

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Application

5α-Androstane-3α,17β-diol (dihydroandrosterone) is a testosterone metabolite. Dihyroandrosterone inhibited the cell growth of seven cancer cell lines while showing weak toxicity on normal cell lines.

Biochem/physiol Actions

Dihydroandrosterone is a testosterone metabolite; affects sperm maturation and survival.

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLCR4586
SLCR4586
0000235325
0000235324
0000225017

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D H Garnier et al.
General and comparative endocrinology, 116(2), 281-290 (1999-11-24)
Concentrations of testosterone, progesterone, Delta4-androstenedione, dihydrotestosterone, 11-ketotestosterone, estrone, estradiol-17beta, 5alpha-androstane, 3alpha, 17beta-diol, and 17alpha-hydroxy, 20beta-dihydroprogesterone were determined by radioimmunoassays in the blood plasma and testicular homogenates of Scyliorhinus canicula. Samples were collected almost every month for 27 months. The weights
Cheryl A Frye
Pharmacology, biochemistry, and behavior, 86(2), 354-367 (2006-11-23)
The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. Research findings regarding androgen abuse in people and hedonic effects of androgens in laboratory rats are reviewed.
J P Deslypere et al.
The Journal of clinical endocrinology and metabolism, 53(2), 430-434 (1981-08-01)
Testosterone, 5 alpha-androstane-17 beta-ol-3-one (DHT) and 5 alpha-androstane-3 alpha,17 beta-diol (Adiol) concentrations were measured in postmortem tissues (pubic skin, scrotal skin, thigh skin, and striated muscle) from 24 males, aged 20-82 yr. Androgen concentrations were highest in scrotal skin, followed
Wei Liu et al.
Journal of chromatography. A, 1233, 1-7 (2012-03-06)
In this paper, a convenient and self-assembled hollow fiber solvent-stir bar microextraction (HF-SSBME) device was developed, which could stir by itself. In the extraction process, the proposed device made the solvent "bar" not floating at the sample solution and exposing
Hajer Jegham et al.
Anti-cancer drugs, 23(8), 803-814 (2012-03-01)
This study investigated the antineoplasic potential of a new family of aminosteroids. The antiproliferative activity of seven 5α-androstane-3α,17β-diol derivatives selected from a screening study was measured on nine cancerous cell lines (HL-60, K-562, LNCaP, PC-3, Shionogi, MCF-7, MDA-MB-231, BT-20, and
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