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145-13-1

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Basic Information
CAS No.: 145-13-1
Name: Pregnenolone
Article Data: 123
Molecular Structure:
Molecular Structure of 145-13-1 (Pregnenolone)
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
Synthetic route
1778-02-5

Pregnenolone acetate

145-13-1

Pregnenolone

Conditions
ConditionsYield
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%
2722-98-7

3β-Hydroxy-5-pregnen-20-one 1,2-Ethanediyl Dithioacetal

145-13-1

Pregnenolone

Conditions
ConditionsYield
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%

(3β)-3-(sulfooxy)pregn-5-en-20-one sodium salt

145-13-1

Pregnenolone

Conditions
ConditionsYield
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
ConditionsYield
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
979-02-2

16-dehydropregnenolone acetate

145-13-1

Pregnenolone

Conditions
ConditionsYield
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
ConditionsYield
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%

Acetic acid (3S,8S,9S,10R,13S,14S,17S)-17-((R)-1-hydroxy-1,5-dimethyl-3-oxo-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

145-13-1

Pregnenolone

Conditions
ConditionsYield
With bis(tri-n-butyltin)oxide In toluene at 110℃; for 0.5h;90%

Pregnenolone hemisuccinate methyl ester

145-13-1

Pregnenolone

Conditions
ConditionsYield
With bis(tri-n-butyltin)oxide In toluene at 110℃; for 17h;85%

16α,17α-cyclobutenopregnenolone acetate

145-13-1

Pregnenolone

Conditions
ConditionsYield
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
ConditionsYield
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.