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P9129 Sigma-Aldrich

5-Pregnen-3β-ol-20-one

≥98%

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

  • CAS Number 145-13-1

  • Empirical Formula (Hill Notation) C21H32O2

  • Molecular Weight 316.48

  •  Beilstein/REAXYS Number 2059026

  •  EC Number 205-647-4

  •  MDL number MFCD00003628

  •  PubChem Substance ID 24899008

  •  NACRES NA.77

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Properties

Related Categories Cell Biology, Lipid, Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Metabolomics,
Quality Level   200
biological source   synthetic (organic)
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)

Description

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

Packaging

1, 5, 25, 100 g in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P9129.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TU5560700
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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739545 Pregnenolone-20,21-13C2-16,16-d2, ≥98 atom %, ≥98% (CP)
740985 Pregnenolone-20,21-13C2-16,16-d2 sulfate sodium salt, ≥98 atom %, 98% (CP)

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