5-Pregnen-3beta-ol-20-one

Base Information

• Chemical Name: 5-Pregnen-3beta-ol-20-one
• CAS No.: 145-13-1
• Molecular Formula: C21H32O2
• Molecular Weight: 316.484
• Hs Code.: 29372900
• NSC Number: 18158,1616
• Wikidata: Q105198056
• Mol file: 145-13-1.mol

Synonyms:566-63-2;(17alpha)-3beta-Hydroxypregn-5-en-20-one;5-pregnene-3alpha-ol-20-one;1-{7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl}ethan-1-one;.DELTA.5-Pregnenolone;PREGNENOLONE-17ALPHA,21,21,21-D4;5-Pregnene-3-ol-20-one;5-Pregnen-3.beta.-ol-20-one;delta-5-pregnen-3beta-ol-20-one;NSC-1616;Pregn-5-en-20-one, 3-hydroxy-;delta-5-pregnen-3-beta-ol-20-one;NSC-18158;(3-beta)-3-Hydroxypregn-5-en-20-one;Pregn-5-en-20-one, 3.beta.-hydroxy-;1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone;D08VVZ;SCHEMBL9926759;NSC1616;1-[(3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-hydroxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone;NSC18158;BBL010646;MFCD00003628;STK801672;AKOS001642232;AKOS021994764;1-[(3S,8S,9S,10R,13S,14S,17R)-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;AS-13783;SY038298;EU-0007813;FT-0631840;FT-0674021;VU0059710-5;EN300-18277057;Z57387832;F3161-0035

Chemical Property of 5-Pregnen-3beta-ol-20-one

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.02E-09mmHg at 25°C
• Melting Point: 188-190 °C
• Refractive Index: 1.549
• Boiling Point: 443.3 °C at 760 mmHg
• PKA: 15.00±0.70(Predicted)
• Flash Point: 188.9 °C
• PSA: 37.30000
• Density: 1.09 g/cm³
• LogP: 4.51530
• Storage Temp.: Refrigerator
• Solubility.: ethanol: soluble10mg/mL, clear, colorless to faintly yellow
• Water Solubility.: 41mg/L(room temperature)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 550

Purity/Quality:

99% ^*data from raw suppliers

Pregnenolone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Description: Pregnenolone 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. Pregnenolone is a natural steroid hormone that serves as a precursor for a wide range of steroids, including mineralocorticoids, glucocorticoids, androgens, and estrogens. Pregnenolone sulfate modulates NMDA receptor responses to exogenously applied glutamate and stimulates transient receptor potential melastatin 3 (TRPM3).
• Uses: glucocortcoid, antiinflammatory Pregnenolone 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

Technology Process of 5-Pregnen-3beta-ol-20-one

There total 115 articles about 5-Pregnen-3beta-ol-20-one 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: 100.0%

Pregnenolone acetate (1778-02-5) → Pregnenolone (145-13-1)

Guidance literature:

With methanol; sodium; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b02021

Reference yield: 100.0%

3β-Hydroxy-5-pregnen-20-one 1,2-Ethanediyl Dithioacetal (2722-98-7) → Pregnenolone (145-13-1)

Guidance literature:

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;

Reference yield: 97.0%

3β-t-butyldimethylsilyloxy-pregn-5-en-20-one (58701-45-4) → Pregnenolone (145-13-1)

Guidance literature:

With chloro-methylsulfanyl-methane; water; potassium iodide; In 1,4-dioxane; at 50 ℃; for 3.3h;

DOI:10.3184/174751917X14955339414758

upstream raw materials:

16-dehydropregnenolone

methyl magnesium iodide

3β-hydroxy-androstene-(5)-carboxylic acid-(17β)-nitrile

sodium diethylmalonate

Downstream raw materials:

Progesterone

6-dehydroprogesterone

3β-(2-acetoxy-benzoyloxy)-pregn-5-en-20-one

pregnenolone 2,5-diiodobenzoat

Refernces

Synthesis and evaluation of novel D-ring substituted steroidal pyrazolines as potential anti-inflammatory agents

10.1016/j.steroids.2019.03.012

The study focuses on the synthesis and evaluation of novel D-ring substituted steroidal pyrazolines as potential anti-inflammatory agents. A series of steroidal derivatives with nitrogen heterocyclic side chains, specifically 4a-4l, were synthesized and tested for their anti-inflammatory effects in activated RAW 264.7 macrophage cells. The synthesis process involved two steps: Claisen-Schmidt condensation with pregnenolone and aromatic aldehydes, followed by nucleophilic addition of thiosemicarbazide to an α, β-unsaturated carbonyl. The synthesized compounds were confirmed by 1H-NMR, 13C-NMR, HRMS, and IR analyses. The purpose of these chemicals was to identify new potential anti-inflammatory agents that could be considered for further research and development in designing anti-inflammatory drugs. Among the synthesized compounds, 4g showed the most potent anti-inflammatory activity with an IC50 value of 0.86 μM on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells, comparable to dexamethasone, and low cytotoxicity, making it a promising therapeutic anti-inflammatory drug candidate.

Synthesis of brassinosteroids of varying acyl side chains and evaluation of their brassinolide-like activity

10.1271/bbb.68.1097

The research details a study on the synthesis and evaluation of brassinosteroids, plant hormones known for their role in cell elongation and division, which are crucial for plant growth and stress resistance. The purpose of the study was to synthesize various brassinosteroids with different acyl side chains and assess their brassinolide-like activity, using the rice lamina inclination assay with synergist indole-3-acetic acid (IAA). The researchers concluded that the introduction of a hydroxyl group in the α-position to the carbonyl group of the ester structure significantly enhanced the activity, with 2β,3β-dihydroxy-17β-[(2R,3S)-2hydroxy-3-methylpentanoyl]oxy-B-homo-7-oxa-5β-androstan-6-one showing the highest activity. The study also found that the R-form of the acyl moiety was more potent than the S-form and that modifying the terminal structure did not increase activity. Chemicals used in the synthesis process included various steroidal compounds like pregnenolone and stigmasterol, as well as a range of reagents such as dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP), and protective groups like tert-butyldiphenylsilyl (TBDPS).