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P9129

Sigma-Aldrich

5-Pregnen-3β-ol-20-one

≥98%

Synonym(s):

3β-Hydroxy-5-pregnen-20-one, Pregnenolone

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About This Item

Empirical Formula (Hill Notation):
C21H32O2
CAS Number:
145-13-1
Molecular Weight:
316.48
Beilstein/REAXYS Number:
2059026
EC Number:
205-647-4
MDL number:
MFCD00003628
UNSPSC Code:
12352211
PubChem Substance ID:
24899008
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

assay

≥98%

form

powder

solubility

ethanol: soluble 10 mg/mL, clear, colorless to faintly yellow

functional group

ketone

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])C(C)=O

InChI

1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

InChI key

ORNBQBCIOKFOEO-QGVNFLHTSA-N

Gene Information

human ... SERPINA6(866)
rat ... Ar(24208)

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Application

5-Pregnen-3β-ol-20-one is suitable for use:
  • as a substrate for 3β-HSD at a concentration of 1 μg/mL to study the time-dependent effect of reduced oxygen tension on 3β-hydroxysteroid dehydrogenase (3β-HSD) activity
  • as a progestin precursor to study the effects of splenic macrophages on progestin secretion of luteal cells
  • in the testicular interstitial cell culture medium at a concentration of 15mg/mL

Biochem/physiol Actions

One of a small number of "neurosteroids," steroids synthesized in the brain rather than peripheral sources. Decreased levels of these neurosteroids has been implicated in rodent cognitive decline with age, but studies in humans have been contradictory.
Testosterone production in rats occurs in Leydig cells of the testis via the Δ4 pathway. Cholesterol is first converted to pregnenolone, then to progesterone, and finally to testosterone. Pregnenolone is the key neurosteroid synthesized in steroidogenic glands. It is also present as a sulfate ester that serves as an antagonist of GABAergic neurons by interacting with γ-aminobutyric acid (GABA) receptor.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nalaka S Rannulu et al.
Journal of the American Society for Mass Spectrometry, 23(9), 1558-1568 (2012-06-27)
The analysis of several bifunctional neutral steroids, 5-α-pregnane diol (5-α-pregnane-3α-20βdiol), estradiol (3,17α-dihydroxy-1,3,5(10)-estratriene), progesterone (4-pregnene-3,20-dione), lupeol (3β-hydroxy-20(29)-lupene), pregnenolone (5-pregnen-3β-ol-20-one), and pregnenolone acetate (5-pregnen-3β-ol-20-one acetate) was accomplished by negative ion electrospray mass spectrometry (ESI-MS) employing adduct formation with various anions: fluoride, bicarbonate
Z Y Hu et al.
Proceedings of the National Academy of Sciences of the United States of America, 84(23), 8215-8219 (1987-12-01)
Oligodendrocyte mitochondria from 21-day-old Sprague-Dawley male rats were incubated with 100 nM [3H]cholesterol. It yielded [3H]pregnenolone at a rate of 2.5 +/- 0.7 and 5-[3H]pregnene-3 beta, 20 alpha-diol at a rate of 2.5 +/- 1.1 pmol per mg of protein
Jui-Hsia Weng et al.
Nature chemical biology, 9(10), 636-642 (2013-08-21)
Pregnenolone (P5) is a neurosteroid that improves memory and neurological recovery. It is also required for zebrafish embryonic development. However, its mode of action is unclear. Here we show that P5 promotes cell migration and microtubule polymerization by binding a
S Matsuyama et al.
Endocrinologia japonica, 39(1), 51-57 (1992-02-01)
We have reported that splenic macrophages play a role in the regulation of progestin secretion in rats. In this study, splenic macrophages were obtained from cycling rats at different estrous cycle stages and co-cultured with luteal cells from mid-pseudopregnant rats
S Onami et al.
Endocrine journal, 43(5), 477-485 (1996-10-01)
A large amount of LH/hCG treatment given to male rats is known to suppress the enzyme activity of cytochrome P450c17 in Leydig cells for 48 h. A high dose LH/hCG injection is also known to allow immunocytes, such as macrophages
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