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A7755

5α-Androstane-3α,17β-diol

Name: 5α-Androstane-3α,17β-diol
Brand: SIGMA

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

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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)

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

GHS08

signalword

Danger

hcodes

H351,H360FD

pcodes

P201 - P308 + P313

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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The identification and simultaneous quantification of neuroactive androstane steroids and their polar conjugates in the serum of adult men, using gas chromatography-mass spectrometry.

L Kancheva et al.

Steroids, 72(11-12), 792-801 (2007-08-25)

Certain androstane steroids (AS) modulate ionotropic receptors, as do the pregnane steroids. Whereas women produce significant amounts of neuroactive progesterone metabolites, the steroid neuromodulators in men originate mainly from the 3-oxo-4-ene C(19)-steroids, which are converted to their 3alpha- and 3beta-hydroxy-5alpha/5beta-reduced

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)

Androstanediol glucuronide production in human liver, prostate, and skin. Evidence for the importance of the liver in 5 alpha-reduced androgen metabolism.

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

Regulation of ovarian 17 beta-hydroxysteroid dehydrogenase activity by gonadotropin.

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)

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Global Trade Item Number

SKU	GTIN
A7755-1G	04061826688427
A7755-100MG	04061832866475

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