Pregnenolone

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
Pregnenolone Structure
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)
Fp 9℃
storage temp. Refrigerator
solubility ethanol: soluble10mg/mL, clear, colorless to faintly yellow
pka15.00±0.70(Predicted)
form Powder
color White to off-white
Water Solubility 41mg/L(room temperature)
Merck 7733
BRN 2059026
InChIKeyORNBQBCIOKFOEO-QGVNFLHTSA-N
LogP4.4 at 20℃
CAS DataBase Reference145-13-1(CAS DataBase Reference)
NIST Chemistry ReferencePregnenolone(145-13-1)
Safety Information
Safety Statements 22-24/25
RIDADR UN 1648 3 / PGII
WGK Germany 3
RTECS TU5560700
HS Code 29372900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Pregnenolone Usage And Synthesis
DescriptionPregnenolone 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.
DescriptionPregnenolone 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 Propertieswhite to off-white powder
Usesglucocortcoid, antiinflammatory
UsesPregnenolone 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
DefinitionChEBI: 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 DescriptionPregnenolone 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 vitropregnenolone 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 vivothe 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 ACETATE 6-METHYLPREGNENOLONE 16ALPHA-METHYLPREGNENOLONE ACETATE 5-PREGNEN-3-BETA, 11-BETA, 17,21-TETROL-20-ONE Pregnenolone 16-ALPHA-METHYLPREGNENOLONE 17-Hydrody pregnenolone 3β,21-Dihydroxy-5-pregnen-20-one 21-acetate, 5-Pregnene-3β,21-diol-20-one 21-acetate, Pregnenolone 21-acetate,PREGNENOLONE 21-ACETATE 17ALPHA-HYDROXYPREGNENOLONE-3,17-DIACETATE 3-BETA-HYDROXY-6,16-ALPHA-DIMETHYL-5-PREGNEN-20-ONE 16,17-Epoxypregnenolone acetate PREGNENOLONE-16ALPHA-CARBONITRILE 16beta-Methyl-16alpha,17alpha-epoxypregnenolone 16-METHYLENE-17ALPHA-HYDROXYPREGNENOLONE 3-ACETATE 16,17-EPOXY-21-ACETOXYPREGNENOLONE 6-METHYL-17ALPHA-HYDROXYPREGNENOLONE PREGNENOLONE METHYL ETHER 17-ACETOXYPREGNENOLONE

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