Estradiol benzoate

Base Information

• Chemical Name: Estradiol benzoate
• CAS No.: 50-50-0
• Molecular Formula: C25H28O3
• Molecular Weight: 376.496
• Hs Code.: 29372319
• European Community (EC) Number: 200-043-7
• NSC Number: 9566
• UNII: 1S4CJB5ZGN
• DSSTox Substance ID: DTXSID9022998
• Nikkaji Number: J4.439C
• Wikipedia: Estradiol_benzoate
• Wikidata: Q11450699
• NCI Thesaurus Code: C29769
• RXCUI: 60661
• Pharos Ligand ID: VTN43LPA3NMQ
• Metabolomics Workbench ID: 144487
• ChEMBL ID: CHEMBL282575
• Mol file: 50-50-0.mol

Synonyms:17beta-estradiol-3-benzoate;Eston-B;estradiol 3-benzoate;estradiol benzoate;oestradiol 3-benzoate

Chemical Property of Estradiol benzoate

Chemical Property:

• Vapor Pressure: 4.08E-12mmHg at 25°C
• Melting Point: 191-198 °C(lit.)
• Refractive Index: 1.604
• Boiling Point: 531.2 °C at 760 mmHg
• PKA: 15.06±0.40(Predicted)
• Flash Point: 212 °C
• PSA: 46.53000
• Density: 1.185 g/cm³
• LogP: 5.12280
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, sparingly soluble in acetone, slightly soluble in methanol.
• Water Solubility.: 0.4mg/L(25 oC)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 376.20384475
• Heavy Atom Count: 28
• Complexity: 582

Purity/Quality:

99.5% ^*data from raw suppliers

Estradiol benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-61-40
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5
• Uses: antiacne, antineoplastic Estradiol is the major estrogen secreted by the premenopausal ovary. Estradiol benzoate is an estradiol analog which contains a benzyl ester at the C-3 position. Estradiol benzoate is useful in the tr eatment of lesions produced by diminution of bodily production of estrogens. Estradiol is the major estrogen secreted by the premenopausal ovary. Estradiol benzoate is an estradiol analog which contains a benzyl ester at the C-3 position. Estradiol benzoate is useful in the treatment of lesions produced by diminution of bodily production of estrogens.
• Clinical Use: Estradiol is a semisynthetic estrogen compound. Its effects will mimic that of estrogen in animals. The most common use in small animals has been to terminate pregnancy. Estradiol benzoate also has been used to terminate pregnancy (5-10 mg/kg divided into two or three SQ injections). Estradiol cypionate formulation had high efficacy (95%), but it had serious adverse effects and is not recommended. Estradiol cypionate is longer acting and more potent than other estrogen formulations. Estradiol valerate injection (20 mg/mL) is also available for human medicine to treat hypoestrogenism.

Technology Process of Estradiol benzoate

There total 14 articles about Estradiol benzoate 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: 92.0%

dibenzoyl disulfide (644-32-6) + estradiol (50-28-2) → Estradiol 3-benzoate (50-50-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.6b02818

Reference yield: 91.0%

(8R,9S,13S,14S,17S)-17-[(4-methoxybenzyl)oxy]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate → Estradiol 3-benzoate (50-50-0)

Guidance literature:

(8R,9S,13S,14S,17S)-17-[(4-methoxybenzyl)oxy]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate; With sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; meso-2,5-bis(methoxycarbonyl)-2,5-dimethylpyrrolidine-1-oxyl; In dichloromethane; at 20 ℃; for 2h;

With water; In dichloromethane; chemoselective reaction;

DOI:10.1021/acs.orglett.0c01839

Reference yield: 89.0%

→ Estradiol 3-benzoate (50-50-0)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; potassium carbonate; In acetonitrile; at 20 ℃; for 3h; Irradiation;

With dmap; In acetonitrile; for 0.166667h;

upstream raw materials:

estrone 3-benzoate

estradiol

benzoyl chloride

benzoyl triflate

Downstream raw materials:

3-benzoyloxy-17β-mercaptoacetoxy-estra-1,3,5(10)-triene

3-<(phenylcarbonyl)oxy>-17β-<(3-pyridinylcarbonyl)oxy>estra-1,3,5(10)-triene

3-Benzoyloxy-17-(5-oxocyclopentylcarbonyloxy)-Δ^1,3,5-estratriene

benzoic acid methyl ester

Refernces

• 1、 -. "HYALURONAN CONJUGATES AND USES THEREOF". Paragraph 0113-0114. . Retrieved 2020/12/13.
• 2、 -. "Preparation method for synthesis of phenolic ester through thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction". Paragraph 0017; 0018; 0077; 0078. . Retrieved 2018/07/30.