17ALPHA-HYDROXYPREGNENOLONE Chemical Properties

Melting point:

273℃

Flash point:

9℃

storage temp. 

-20°C

solubility 

Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated)

form 

Solid

Boiling point:

478.4±45.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

pka

13.02±0.70(Predicted)

color 

White to Off-White

InChI

InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1

InChIKey

JERGUCIJOXJXHF-TVWVXWENSA-N

SMILES

C[C@]12CC[C@]3([H])[C@]4(CC[C@@H](CC4=CC[C@@]3([H])[C@]1([H])CC[C@]2(O)C(=O)C)O)C

CAS DataBase Reference

387-79-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,T

Risk Statements 

11-23/24/25-39/23/24/25

Safety Statements 

7-16-36/37-45

RIDADR 

UN1230 - class 3 - PG 2 - Methanol

WGK Germany 

3

RTECS 

TU5548000

MSDS

• Language:English Provider:SigmaAldrich

17ALPHA-HYDROXYPREGNENOLONE Usage And Synthesis

Description

17α-hydroxy Pregnenolone is a metabolite of pregnenolone and a precursor in the biosynthesis of dehydroepiandrosterone (DHEA; ). It is formed from pregnenolone by cytochrome P450 (CYP) isoform CYP17A1 hydroxylase activity and then converted to dehydroepiandrosterone by CYP17A1-mediated 17,20-lyase activity. Plasma levels of 17α-hydroxy pregnenolone are elevated in patients with type II 3β-hydroxysteroid dehydrogenase deficiency, a form of congenital adrenal hyperplasia.

Uses

17α-hydroxypregnenolone has been used as a substrate for the enzyme 3β‐hydroxysteroid dehydrogenase (3β‐HSD) expressed in COS1 cells.

General Description

17α-hydroxypregnenolone is a derived from pregnenolone.

Biochem/physiol Actions

17α-hydroxypregnenolone acts as a precursor for cortisol and sex steroids.

IC 50

Human Endogenous Metabolite

References

[1] ELYSE M PETRUNAK. Structures of human steroidogenic cytochrome P450 17A1 with substrates.[J]. The Journal of Biological Chemistry, 2014, 289 47: 32952-32964. DOI: 10.1074/jbc.m114.610998
[2] JEAN FIET . Plasma 17-OH pregnenolone: comparison of a time-resolved fluoroimmunoassay using a new tracer 17-OH pregnenolone-3-oxyacetyl-biotine with a radioimmunoassay using 125I 17-OH pregnenolone-3-hemisuccinate-histamine[J]. Steroids, 2001, 66 2: Pages 81-86. DOI: 10.1016/s0039-128x(00)00207-5

17ALPHA-HYDROXYPREGNENOLONE(387-79-1)Related Product Information

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