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A7755

Sigma-Aldrich

5α-Androstane-3α,17β-diol

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Synonym(s):
3α,17β-Dihydroxy-5α-androstane, Dihydroandrosterone
Empirical Formula (Hill Notation):
C19H32O2
CAS Number:
Molecular Weight:
292.46
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥98% (TLC)

Quality Level

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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1 of 4

This Item
A8380A7883H2898
vibrant-m

A7755

5α-Androstane-3α,17β-diol

vibrant-m

A8380

5α-Androstan-17β-ol-3-one

vibrant-m

A7883

5α-Androst-16-en-3α-ol

vibrant-m

H2898

6β-Hydroxytestosterone

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

assay

≥98% (TLC)

assay

≥97.5%

assay

≥98% (TLC)

assay

≥97% (HPLC)

drug control

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

drug control

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

drug control

-

drug control

-

technique(s)

toxicology assay: suitable

technique(s)

-

technique(s)

GC/MS: suitable

technique(s)

-

storage temp.

room temp

storage temp.

-

storage temp.

room temp

storage temp.

room temp

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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.
Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism--II. In the ventral prostate and in the seminal vesicles.
F Celotti et al.
Journal of steroid biochemistry, 11(1A), 221-225 (1979-07-01)
Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism. I--In the hypothalamus and in the anterior pituitary.
F Celotti et al.
Journal of steroid biochemistry, 11(1A), 215-219 (1979-07-01)

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