Pregnenolone acetate

Base Information

• Chemical Name: Pregnenolone acetate
• CAS No.: 1778-02-5
• Molecular Formula: C23H34O3
• Molecular Weight: 358.521
• Hs Code.: 29153900
• NSC Number: 64827
• DSSTox Substance ID: DTXSID20859678
• Mol file: 1778-02-5.mol

Synonyms:Pregn-5-en-20-one,3b-hydroxy-, acetate (6CI,8CI);3b-Acetoxy-5-pregnen-20-one;3b-Hydroxypregn-5-en-20-oneacetate;3b-Pregn-5-enol-20-one acetate;5-Pregnen-3b-ol-20-one acetate;5-Pregnene-3b-acetoxy-20-one;Antofin;Artivis;Enescorb;NSC 64827;

Chemical Property of Pregnenolone acetate

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 2.16E-08mmHg at 25°C
• Melting Point: 149-152 ºC
• Refractive Index: 1.533
• Boiling Point: 452.9 ºC at 760 mmHg
• Flash Point: 194.2 ºC
• PSA: 43.37000
• Density: 1.09 g/cm³
• LogP: 5.08610
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 358.25079494
• Heavy Atom Count: 26
• Complexity: 650

Purity/Quality:

99% ^*data from raw suppliers

Pregnenolone Acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C
• Uses: Pregnenolone acetate is an intermediate in the synthesis of progesterone. It is uses as a glucocorticoid and as a skin-conditioning and skin anti-aging agent. It acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. It has also been shown to stimulate locomotor activity and neuronal function in rats.

Technology Process of Pregnenolone acetate

There total 85 articles about Pregnenolone acetate 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 (145-13-1) + acetic anhydride (108-24-7) → Pregnenolone acetate (1778-02-5)

Guidance literature:

With pyridine; at 37 ℃; Inert atmosphere;

DOI:10.1021/jf506361r

Reference yield: 98.18%

16-dehydropregnenolone acetate (979-02-2) → Pregnenolone acetate (1778-02-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 30 ℃; for 16h; under 2327.2 Torr;

DOI:10.1016/S0040-4020(01)86968-4

Reference yield: 98.0%

3β-acetoxypregn-5-en-20α-ol (76984-91-3) → Pregnenolone acetate (1778-02-5)

Guidance literature:

With Me-IBX; In acetone; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.11.013

upstream raw materials:

3β-acetoxy-pregna-5,16-dien-20-one

methyl magnesium iodide

3β-acetoxy-androst-5-ene-17β-carbonitrile

3β-acetoxy-5-etienic acid chloride

Downstream raw materials:

3β,21-diacetoxypregn-5-en-20-one

Pregnenolone

Androsta-1,4-diene-3,17-dione

11α,15β-dihydroxypregn-4-ene-3,20-dione

Refernces

• 1、 Takeuchi,Fujita,Goto,Morisaki,Osone,Tobinaga. "Dictamnol, a new trinor-guaiane type sesquiterpene, from the roots of Dictamnus dasycarpus Turcz.". . p. 923 - 925. Retrieved 1993.
• 2、 Akhrem et al.. "". . . Retrieved 1974.
• 3、 Wu, Danni,Carillo, Kathleen Joyce D.,Tsai, Shen-Long,Shie, Jiun-Jie,Tzou, Der-Lii M.. "Solid-state nuclear magnetic resonance investigation of neurosteroid compounds and magnesium interactions". . p. 1318 - 1326. Retrieved 2019.
• 4、 Mauvais, Antony,Hetru, Charles,Roussel, Jean Pierre,Luu, Bang. "Inhibition of Ecdysone Biosynthesis: Preparation of Acetylenic Intermediates". . p. 8597 - 8604. Retrieved 1993.
• 5、 Sarfaty,Fales. "". . p. 288,289. Retrieved 1970.
• 6、 Zimmerman, Mary P.,Li, Hui-ting,Duax, William L.,Weeks, Charles M.,Djerassi, Carl. "Stereochemical Effects in Cyclopropane Ring Openings: Biomimetic Ring Openings of All Isomers of 22,23-Methylenecholesterol Acetate". . p. 5602 - 5612. Retrieved 1984.
• 7、 Mikle, Gábor,Zugó, Alexandra,Szatnik, Erzsébet,Maxim, Anita,Mahó, Sándor,Kollár, László. "Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation". . p. 1861 - 1867. Retrieved 2021.
• 8、 Amelichev, Stanislav A.,Shashkov, Alexander S.,Zavarzin, Igor V.,Rakitin, Oleg A.. "Synthesis of 17-(1,2,3-dithiazole) androstene derivatives". . p. 186 - 187. Retrieved 2011.
• 9、 Ehrenstein. "-". . p. 506,514. Retrieved 1939.
• 10、 Kolb,Hua,Duax. "Stereochemistry of long-lasting opiates. 2. δ-Selective opiate antagonists and their agonist analogues". . p. 3003 - 3010. Retrieved 1987.