Pregnenolone
Synonym(s):3β-Hydroxy-5-pregnen-20-one;3β-hydroxypregn-5-en-20-one;Pregnenolone
- CAS NO.:145-13-1
- Empirical Formula: C21H32O2
- Molecular Weight: 316.48
- MDL number: MFCD00003628
- EINECS: 205-647-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is Pregnenolone?
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
The Uses of Pregnenolone
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
The Uses of Pregnenolone
glucocortcoid, antiinflammatory
Background
A 21-carbon steroid, derived from cholesterol and found in steroid hormone-producing tissues. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids.
What are the applications of Application
Pregnenolone is an prohormone neurosteroid also a precursor to gonadal steroid hormones and the adrenal corticosteroids
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].
Metabolism
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.
Properties of Pregnenolone
Melting point: | 188-190 °C |
Boiling point: | 395.89°C (rough estimate) |
alpha | 28.5 º (c=1, EtOH) |
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 |
CAS DataBase Reference | 145-13-1(CAS DataBase Reference) |
NIST Chemistry Reference | Pregnenolone(145-13-1) |
Safety information for Pregnenolone
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H225:Flammable liquids H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Pregnenolone
InChIKey | ORNBQBCIOKFOEO-QGVNFLHTSA-N |
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