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:

1-((3S,10R,13S,17S)-10,13-dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone

dihydroprogesterone

5-pregnen-3β-ol

3α-hydroxy-10.13-dimethyl-17β-ethyl-gonene-(5)

Refernces

• 1、 Lin, Zongtao,Marepally, Srinivasa R.,Ma, Dejian,Kim, Tae-Kang,Oak, Allen Sw.,Myers, Linda K.,Tuckey, Robert C.,Slominski, Andrzej T.,Miller, Duane D.,Li, Wei. "Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer". . p. 5102 - 5108. Retrieved 2016.
• 2、 Szendi, Zsuzsanna,Forgo, Peter,Tasi, Gyula,Boecskei, Zsolt,Nyerges, Levente,Sweet, Frederick. "1,5-Hydride shift in Wolff-Kishner reduction of (20R)-3β,20, 26-trihydroxy-27-norcholest-5-en-22-one: Synthetic, quantum chemical, and NMR studies". . p. 31 - 38. Retrieved 2002.
• 3、 Ruzicka,Meldahl. "". . p. 364. Retrieved 1940.
• 4、 Duval,Vickery. "3-Methoxybenzidine: A potent inhibitor of cholesterol side chain cleavage cytochrome P-450". . p. 473 - 481. Retrieved 1980.
• 5、 Singh. "A new mild PTSA-catalyzed method for sulfate ester hydrolysis and acid-catalyzed rearrangement of 12-acetyl-diene-11-ol tetracyclic triterpenoids involving an angular methyl migration". . p. 6973 - 6976. Retrieved 2000.
• 6、 Perez, Marina G.,Maier, Marta S.. "Mild deprotection of steroid esters by bis(tributyltin)oxide". . p. 3311 - 3314. Retrieved 1995.
• 7、 Miescher,Kaegi. "-". . p. 184. Retrieved 1939.
• 8、 Mostinski, Yelena,Lankri, David,Konovalov, Yana,Nataf, Riva,Tsvelikhovsky, Dmitry. "Proline-promoted dehydroxylation of α-ketols". . p. 9345 - 9350. Retrieved 2019.
• 9、 Pasanen,Pelkonen. "Cholesterol side-chain cleavage activity in human placenta and bovine adrenals: An one-step method for separation of pregnenolone formed in vitro". . p. 517 - 527. Retrieved 1984.
• 10、 Bull,Tuinman. "". . p. 2151,2154. Retrieved 1975.