Grundinformationen
- CAS
145-13-1- Standard-SMILES
CC(=O)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C- InChIKey
ORNBQBCIOKFOEO-UHFFFAOYSA-N- Summenformel
- C21H32O2
- Durchschnittliche Molmasse
- 316,5 g/mol
- Monoisotopische Masse
- 316,24023026
Namen und Bezeichner
- Bevorzugter Name
- Pregn-5-en-20-one, 3beta-hydroxy-
- IUPAC
- 1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone
- Lokaler Name
- Pregnenolon
- Englischer Name
- Pregnenolone
- Summenformel
- C21H32O2
- Molmasse
- 316.48
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
145-13-1- PubChem CID
- 1027
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,2
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 550
Physikochemische Eigenschaften
- Schmelzpunkt
- 188 · 188-190 °C
- Siedepunkt
- 395.89 °C · 395.89°C (rough estimate)
- Dichte
- 1.0382 · 1.0382 (rough estimate)
- Dampfdruck
- 0 · 0-0Pa at 20-25℃
- Brechungsindex
- 1.5344 · 1.5344 (estimate)
- Flammpunkt
- 9 ℃ · 9℃
- storage temp.
- Refrigerator
- Löslichkeit
- 10 mg/mL, · ethanol: soluble10mg/mL, clear, colorless to faintly yellow
- Aggregatzustand
- Powder
- pka
- 15 · 15.00±0.70(Predicted)
- Farbe
- White to off-white
- Wasserlöslichkeit
- 41 mg/L · 41mg/L(room temperature)
- Merck
- 7733 · 7733
- BRN
- 2059026 · 2059026
- Major Application
- clinical testingclinical testing
- 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
- InChIKey
- ORNBQBCIOKFOEO-QGVNFLHTSA-N
- SMILES
- O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)C)(CC3)C)CC=C2C1)C
- LogP
- 4.4 at · 4.4 at 20℃
- CAS Datenbank
- 145 · 145-13-1(CAS DataBase Reference)
- NIST chemische Informationen
- Pregnenolone(145-13-1)
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29372900
- RTECS-Nr.
- TU5560700
- safety_code
- 22-24/25
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Chemie und Industrie
Anwendungen
BeschreibungPregnenolone 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.
VerwendenPregnenolone 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
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Ergänzende Hinweise
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.
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