P9129
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:
Molecular Weight:
316.48
UNSPSC Code:
12352211
NACRES:
NA.77
PubChem Substance ID:
EC Number:
205-647-4
Beilstein/REAXYS Number:
2059026
MDL number:
biological source
synthetic (organic)
Quality Level
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)
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
涉药品监管产品
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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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| P9129-25G | 04061834402336 |
| P9129-100G | 04061835548019 |
| P9129-1G | 04061834402329 |
| P9129-5G | 04061834402343 |