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| CAS No.: | 145-13-1 |
|---|---|
| Name: | Pregnenolone |
| Molecular Structure: | |
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| Formula: | C21H32O2 |
| Molecular Weight: | 316.484 |
| Synonyms: | 3-beta-Hydroxypregn-5-en-20-one;3beta-Hydroxy-Delta5-pregnen-20-one;3beta-Hydroxy-5-pregnene-20-one;Delta5-Pregnen-3beta-ol-20-one;Pregn-5-ene-3beta-ol-20-one;Pregnenolone:Pregna-5-ene-3beta-ol-20-one;Arthenolone; |
| EINECS: | 205-647-4 |
| Density: | 1.09 g/cm3 |
| Melting Point: | 188-190 °C |
| Boiling Point: | 443.3 °C at 760 mmHg |
| Flash Point: | 188.9 °C |
| Solubility: | Insoluble in water |
| Appearance: | white to off-white powder |
| Safety: | 22-24/25 |
| PSA: | 37.30000 |
| LogP: | 4.51530 |
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| Conditions | Yield |
|---|---|
| With methanol; sodium In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; | 100% |
| With potassium hydroxide; water In methanol at 30℃; for 2h; | 97% |
| With potassium hydroxide In water; tert-butyl alcohol at 30℃; for 12h; | 96% |
| Conditions | Yield |
|---|---|
| With (1,1',1''-[nitrilotri(4,1-phenylene)]tri(ethan-1-one)); lithium perchlorate; silica gel; sodium hydrogencarbonate In dichloromethane; water; acetonitrile for 2h; electrolysis; | 100% |
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In 1,4-dioxane at 20℃; Hydrolysis; | 97% |
- 58701-45-4
3β-t-butyldimethylsilyloxy-pregn-5-en-20-one
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 3.3h; | 97% |
| Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2.17 h / -78 - -20 °C / Inert atmosphere 1.2: Cooling; Inert atmosphere 2.1: mercury(II) oxide; water; mercury dichloride / acetonitrile / 2.5 h / Reflux 3.1: tetrahydrofuran; diethyl ether / 1.5 h / Cooling 4.1: hydrogenchloride / dichloromethane; methanol; water / 0.25 h 5.1: human P450 11A1; yeast alcohol dehydrogenase; oxygen-18 / aq. phosphate buffer / 37 °C / Microbiological reaction View Scheme |
| Conditions | Yield |
|---|---|
| Stage #1: 16-dehydropregnenolone acetate With hydrogen at 0 - 25℃; for 1h; Stage #2: With potassium hydroxide for 2h; Reflux; | 92.8% |
| Multi-step reaction with 2 steps 1: 98 percent / H2 / Pd/C / ethyl acetate / 12 h / 30 °C / 2327.23 Torr 2: 97 percent / potassium hydroxide; H2O / methanol / 2 h / 30 °C View Scheme | |
| Multi-step reaction with 2 steps 1: 97 percent / H2 / Pd/C / 15 h / 30 °C / 2327.17 Torr 2: 96 percent / KOH / 2-methyl-propan-2-ol; H2O / 16 h / 30 °C View Scheme |
- 18843-28-2
3β-formyloxypregn-5-en-20-one
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| With lipase from Candida cylindracea; octanol In various solvent(s) at 37℃; for 144h; | 90% |
| With bis(tri-n-butyltin)oxide In benzene at 80℃; for 1.5h; | 90% |
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| With bis(tri-n-butyltin)oxide In toluene at 110℃; for 0.5h; | 90% |
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| With bis(tri-n-butyltin)oxide In toluene at 110℃; for 17h; | 85% |
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| With sodium hydroxide; dihydrogen peroxide In methanol at 5℃; for 24h; other reagent: lithium, NH3(liquid); | 78% |
- 136634-01-0
(20R)-3β,20,26-trihydroxy-27-norcholest-5-en-22-one
- 145-13-1
Pregnenolone
| Conditions | Yield |
|---|---|
| Stage #1: (20R)-3β,20,26-trihydroxy-27-norcholest-5-en-22-one With hydrazine hydrate In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 165 - 195℃; for 2.5h; Stage #2: With sodium periodate; sulfuric acid In ethanol for 0.0833333h; | 37% |
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Chemistry
Molecule structure of Pregnenolone (CAS NO.145-13-1):
IUPAC Name: 1-[(3S,8S,9S,10R,13S,14S,17S)-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
Molecular Weight: 316.47758 g/mol
Molecular Formula: C21H32O2
Density: 1.09 g/cm3
Melting Point: 188-190 °C
Boiling Point: 443.3 °C at 760 mmHg
Flash Point: 188.9 °C
Index of Refraction: 1.549
Molar Refractivity: 92.35 cm3
Molar Volume: 290 cm3
Polarizability: 36.61×10-24 cm3
Surface Tension: 42.7 dyne/cm
Enthalpy of Vaporization: 80.89 kJ/mol
Vapour Pressure: 1.02E-09 mmHg at 25 °C
XLogP3: 4.2
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Tautomer Count: 3
Exact Mass: 316.24023
MonoIsotopic Mass: 316.24023
Topological Polar Surface Area: 37.3
Heavy Atom Count: 23
Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O))C
InChI: 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
EINECS: 205-647-4
Product Categories: Steroids; Steroids & Hormones - 13C & 2H; Biochemistry; Hydroxyketosteroids; Steroids (Others)
Uses
Pregnenolone (CAS NO.145-13-1) is used for biochemical research. It is also used as steroid pharmaceutical intermediates and synthesis of steroid drugs.
Production
Pregnenolone is made by cholesterol. This conversion involves hydroxylation at the side-chain at C20 and C22 positions, with cleavage of the side-chain. The enzyme performing this task is cytochrome P450scc, located in the mitochondria, and controlled by pituitary tropic hormones, such as ACTH, FSH, LH.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD | intraperitoneal | > 200mg/kg (200mg/kg) | Journal of Medicinal Chemistry. Vol. 11, Pg. 117, 1968. |
Safety Profile
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: TU5560700
Specification
Pregnenolone (CAS NO.145-13-1) is also named as 3-beta-Hydroxypregn-5-en-20-one ; 3beta-Hydroxypregn-5-en-20-one ; 5-Pregnen-3-beta-ol-20-one ; 5-Pregnen-3beta-ol-20-one ; Arthenolone ; Bina-Skin ; Enelone ; NSC 1616 ; Natolone ; Pregn-5-en-20-one, 3-hydroxy-, (3-beta)- ; Pregnenolona ; Pregnenolona [INN-Spanish] ; Pregnenolonum ; Pregnenolonum [INN-Latin] ; Pregnetan ; Pregneton ; Pregnolon ; Prenolon ; Regnosone ; Skinostelon ; UNII-73R90F7MQ8 ; delta5-Pregnenolone . Pregnenolone (CAS NO.145-13-1) is white to off-white powder. It is insoluble in water. Its esterified version, pregnenolone sulfate, is water-soluble.