Pregnanolone

Base Information

• Chemical Name: Pregnanolone
• CAS No.: 128-20-1
• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.5
• European Community (EC) Number: 634-188-6
• NSC Number: 82867
• UNII: BXO86P3XXW
• DSSTox Substance ID: DTXSID1046342
• Nikkaji Number: J6.567F
• Wikipedia: Allopregnanolone,Pregnanolone
• Wikidata: Q18344323
• NCI Thesaurus Code: C81407
• Metabolomics Workbench ID: 35454
• ChEMBL ID: CHEMBL210952
• Mol file: 128-20-1.mol

Synonyms:3 alpha Hydroxy 5 alpha pregnan 20 one;3 alpha Hydroxy 5 beta pregnan 20 one;3 alpha, 5 beta Tetrahydroprogesterone;3 alpha, 5 beta-Tetrahydroprogesterone;3 alpha-Hydroxy-5 alpha-pregnan-20-one;3 alpha-Hydroxy-5 beta-pregnan-20-one;3 Hydroxypregnan 20 one;3-Hydroxypregnan-20-one;3beta Hydroxy 5alpha pregnan 20 one;3beta-Hydroxy-5alpha-pregnan-20-one;Allopregnan 3 beta ol 20 one;Allopregnan-3 beta-ol-20-one;Allopregnanolone;alpha-Hydroxy-5 alpha-pregnan-20-one, 3;alpha-Hydroxy-5 beta-pregnan-20-one, 3;alpha-pregnan-20-one, 3 alpha-Hydroxy-5;beta-ol-20-one, Allopregnan-3;beta-pregnan-20-one, 3 alpha-Hydroxy-5;Eltanolone;Epipregnanolone;Pregnan 3alpha ol 20 one;Pregnan-3alpha-ol-20-one;Pregnanolone;Pregnanolone, (3alpha)-isomer;Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer;Pregnanolone, (3alpha,5alpha)-isomer;Pregnanolone, (3alpha,5beta)-isomer;Pregnanolone, (3beta)-isomer;Pregnanolone, (3beta, 5alpha)-isomer;Pregnanolone, (3beta, 5alpha, 17alpha)-isomer;Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer;Pregnanolone, (3beta, 5beta)-isomer;Pregnanolone, (3beta, 5beta, 17alpha)-isomer;Pregnanolone, (3beta, 5beta,14beta)-isomer;Pregnanolone, (5alpha)-isomer;Sepranolone

Chemical Property of Pregnanolone

Chemical Property:

• Appearance/Colour: Solid.
• Vapor Pressure: 3.05E-09mmHg at 25°C
• Melting Point: 149 °C
• Refractive Index: 1.524
• Boiling Point: 431.2 °C at 760 mmHg
• PKA: 15.12±0.70(Predicted)
• Flash Point: 183.9 °C
• PSA: 37.30000
• Density: 1.053g/cm³
• LogP: 4.59520
• Storage Temp.: Store at RT
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: 8mg/L(room temperature)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 318.255880323
• Heavy Atom Count: 23
• Complexity: 500

Purity/Quality:

98%,99%, ^*data from raw suppliers

5β-Pregnan-3α-ol-20-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Recent ClinicalTrials: Allopregnanolone Regenerative Therapeutic for Early Alzheimer's Disease: Intramuscular Study
• Recent EU Clinical Trials: Allopregnanolone effects on short term memory
• Uses: A hyponotic-anaesthetic agent A hyponotic-anaesthetic agent.

Technology Process of Pregnanolone

There total 4 articles about Pregnanolone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

pregnanedione (128-23-4) → pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1) + PREGNANOLONE (128-20-1,128-21-2,516-54-1,516-55-2,4243-94-1,4320-08-5,4406-35-3,4406-37-5,4469-03-8,13089-85-5,13089-86-6,14615-01-1,21788-58-9,24557-99-1,25126-79-8,26961-00-2,36027-63-1,39845-99-3,40135-22-6,72691-57-7,81076-02-0,95118-68-6,110350-90-8)

Guidance literature:

With recombinant human aldo-keto reductase 1C₃; NADPH; In methanol; at 37 ℃; for 1.5h; pH=7; stereospecific reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1042/BJ20101804

Reference yield:

Progesterone (57-83-0) → pregnanedione (128-23-4) + 3β-hydroxy-5β-pregnan-20-one (128-21-2) + pregnanediol (80-92-2) + pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1) + PREGNANOLONE (128-20-1,128-21-2,516-54-1,516-55-2,4243-94-1,4320-08-5,4406-35-3,4406-37-5,4469-03-8,13089-85-5,13089-86-6,14615-01-1,21788-58-9,24557-99-1,25126-79-8,26961-00-2,36027-63-1,39845-99-3,40135-22-6,72691-57-7,81076-02-0,95118-68-6,110350-90-8) + 3α-hydroxy-5β-pregnane-20-one-3-glucuronide (31329-54-1)

Guidance literature:

With phosphate buffer; (S)-2-[3]pyridyl-pyrrolidine-1-carboxylic acid amide; α-D-glucose 6-phosphate; bovine liver tissue supernatant; NADP; UDP-glucuronic acid; at 37 ℃; for 5h; Product distribution; <14C>labeled;

DOI:10.1016/0039-128X(82)90041-1

Reference yield:

(1S,4aS,4bS,7S,8aS,10aR)-2,4b-Dimethyl-1-pent-3-ynyl-tetradecahydro-phenanthrene-2,7-diol (75517-77-0,82332-04-5) → isopregnanolone (516-55-2) + 1-((3S,5S,8R,9R,10S,13S,14S,17R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone (128-20-1,128-21-2,516-54-1,516-55-2,4243-94-1,4320-08-5,4406-35-3,4406-37-5,4469-03-8,13089-85-5,13089-86-6,14615-01-1,21788-58-9,24557-99-1,25126-79-8,26961-00-2,36027-63-1,39845-99-3,40135-22-6,72691-57-7,81076-02-0,95118-68-6,110350-90-8)

Guidance literature:

With potassium hydroxide; trifluoroacetic acid; trifluoroacetic anhydride; Yield given. Multistep reaction; 1.) -18 deg C, 2 h; 2.) EtOH, room temerature, 4 h;

DOI:10.1016/S0040-4039(00)92748-5

upstream raw materials:

Progesterone

hexane

pregnanedione

(1S,4aS,4bS,7S,8aS,10aR)-2,4b-Dimethyl-1-pent-3-ynyl-tetradecahydro-phenanthrene-2,7-diol

Downstream raw materials:

pregnanediol

C₂₈H₄₂N₂O₃S

Pregnanolone sulfate

pregnadiol

Refernces

• 1、 Jin, Yi,Mesaros, A. Clementina,Blair, Ian A.,Penning, Trevor M.. "Stereospecific reduction of 5β-reduced steroids by human ketosteroid reductases of the AKR (aldo-keto reductase) superfamily: Role of AKR1C1-AKR1C4 in the metabolism of testosterone and progesterone via the 5β-reductase pathway". experimental part. p. 53 - 61. Retrieved 2012/06/15.
• 2、 Kametani, Tetsuji,Suzuki, Koji,Nemoto, Hideo. "TOTAL SYNTHESIS OF (+)-5α-DIHYDROPREGNENOLONE VIA ACETYLENE-CATION CYCLIZATION". . p. 1469 - 1470. Retrieved 2007/10/02.