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Pregnenolone

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Pregnenolone Basic information

Product Name:
Pregnenolone
Synonyms:
  • DELTA5-PREGNEN-3BETA-OL-20-ONE
  • DELTA5-PREGNEN-3B-OL-20-ONE
  • DELTA-5-PREGNENE-3B-OL-20-ONE
  • DELTA5-PREGNENOLONE
  • 3BETA-HYDROXY-5-PREGNEN-20-ONE
  • 3BETA-HYDROXYPREGN-5-EN-20-ONE
  • 3b-hydroxy-5-pregnen-20-one
  • 5-pregnenolone
CAS:
145-13-1
MF:
C21H32O2
MW:
316.48
EINECS:
205-647-4
Product Categories:
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroid and Hormone
  • API
  • chemical reagent
  • pharmaceutical intermediate
  • Steroids
  • Steroids & Hormones - 13C & 2H
  • Biochemistry
  • Hydroxyketosteroids
  • Steroids (Others)
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • 145-13-1
Mol File:
145-13-1.mol
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Pregnenolone Chemical Properties

Melting point:
188-190 °C
alpha 
28.5 º (c=1, EtOH)
Boiling point:
395.89°C (rough estimate)
Density 
1.0382 (rough estimate)
vapor pressure 
0-0Pa at 20-25℃
refractive index 
1.5344 (estimate)
Flash point:
9℃
storage temp. 
Refrigerator
solubility 
ethanol: soluble10mg/mL, clear, colorless to faintly yellow
form 
Powder
pka
15.00±0.70(Predicted)
color 
White to off-white
Water Solubility 
41mg/L(room temperature)
Merck 
7733
BRN 
2059026
InChIKey
ORNBQBCIOKFOEO-QGVNFLHTSA-N
LogP
4.4 at 20℃
CAS DataBase Reference
145-13-1(CAS DataBase Reference)
NIST Chemistry Reference
Pregnenolone(145-13-1)
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Safety Information

Safety Statements 
22-24/25
RIDADR 
UN 1648 3 / PGII
WGK Germany 
3
RTECS 
TU5560700
HS Code 
29372900

MSDS

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Pregnenolone Usage And Synthesis

Description

Pregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a number of physiologically active C21 steroids, including the female sex hormone progesterone and the adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19 steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18 female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens.

Description

Pregnenolone is a natural steroid hormone that serves as a precursor for a wide range of steroids, including mineralocorticoids, glucocorticoids, androgens, and estrogens. Pregnenolone sulfate modulates NMDA receptor responses to exogenously applied glutamate and stimulates transient receptor potential melastatin 3 (TRPM3).

Chemical Properties

white to off-white powder

Uses

glucocortcoid, antiinflammatory

Uses

Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA an tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A

Definition

ChEBI: A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20.

General Description

Pregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution? is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards.

in vitro

pregnenolone is the precursor from which almost all of the other steroid hormones are made, including dhea, testosterone, progesterone, the estrogens and cortisol. pregnenolone also operates as a powerful neurosteroid in the brain, which modulates the transmission of messages from neuron to neuron and strongly influencing learning and memory processes [1].

in vivo

the ability of pregnenolone sulfate derivatives (pregs) to modulate the age-induced learning impairment was tested in 16- month-old mice using the step-down type of passive avoidance. decreased step-down latency was observed in the passive avoidance task in 16-month-old mice compared to 3-month-old mice, revealing retention deficits in old mice. pretraining injections of pregs dose-dependently improved the 24 h delay retention performances in this task in old mice [1].

References

[1] vallée m, mayo w, le moal m. role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging. brain res brain res rev. 2001 nov;37(1-3):301-12.

Pregnenolone Preparation Products And Raw materials

Raw materials

Preparation Products

PregnenoloneSupplier

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