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A7755

Sigma-Aldrich

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
EC Number:
217-447-4
MDL number:
MFCD00003676
UNSPSC Code:
51111800
PubChem Substance ID:
24278236
NACRES:
NA.77

Assay

≥98% (TLC)

Quality Level

200

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

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

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

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

Signal Word

Danger

Hazard Statements

H351,H360FD

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class Code

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

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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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.
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
R S Rittmaster et al.
The Journal of clinical endocrinology and metabolism, 76(4), 977-982 (1993-04-01)
Androstanediol glucuronide (Adiol G) has been reported to be a marker of peripheral androgen metabolism and action. It consists of two isomers, Adiol 3-G and Adiol 17-G. Adiol G is formed from unconjugated precursors by the enzyme glucuronyl transferase. To
17α-ethynyl-5α-androstane-3α, 17β-diol treatment of MNU-induced mammary cancer in rats
Ahlem, C., et al.
International Journal of Breast Cancer, doi: 10-doi: 10 (2011)
B Eckstein et al.
Biochimica et biophysica acta, 627(2), 165-171 (1980-01-17)
Serum testosterone levels are elevated prior to the lutropin surge, and decline abruptly following the release of endogenous lutropin. To investigate this phenomenon, the activity of 17 beta-hydroxysteroid dehydrogenase, the enzyme directly related to testosterone production from androstenedione, was measured.
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