Promestriene

Base Information

• Chemical Name: Promestriene
• CAS No.: 39219-28-8
• Molecular Formula: C22H32O2
• Molecular Weight: 328.495
• Hs Code.: 29093090
• European Community (EC) Number: 254-361-6
• UNII: GXM4PER6WZ
• Nikkaji Number: J15.809G
• Wikipedia: Promestriene
• Wikidata: Q76414696
• NCI Thesaurus Code: C76998
• ChEMBL ID: CHEMBL2105394
• Mol file: 39219-28-8.mol

Synonyms:3-propoxy-17 beta-methoxy-1,3,5(10)-estratriene;Colpotrofin;Colpotrophine;Delipoderm;promestriene

Chemical Property of Promestriene

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 64-66 °C
• Refractive Index: 1.546
• Boiling Point: 436.8 °C at 760 mmHg
• Flash Point: 153.3 °C
• PSA: 18.46000
• Density: 1.06 g/cm³
• LogP: 5.34650
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 328.240230259
• Heavy Atom Count: 24
• Complexity: 436

Purity/Quality:

99.5%min ^*data from raw suppliers

Promestriene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCOC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4OC)C
• Isomeric SMILES: CCCOC1=CC2=C(C=C1)[C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC)C
• Recent ClinicalTrials: LASER and Radiofrequency for Treatment of Vaginal Vulvar Atrophy (VVA) in Women Treated for Breast Cancer (EPMLARF-arm2)
• Recent EU Clinical Trials: EVALUATION OF THE ACCEPTABILITY AND EFFICACY OF 10 MICROGRAMS OF ESTRADIOL VAGINAL TABLETS VS PROMESTRIENE VAGINAL CREAM
• Indications: 1. Cold cream or cream: used for the treatment of the atrophic lesions in vulva, vestibule and vaginal ring portion. 2. Vaginal Capsules: for the treatment of vaginal atrophy due to estrogen deficiency; the persistent delayed healing, delayed crust in the mucous membrane part of cervical, vulvar and vaginal due to childbirth, local surgery or partial physical therapy (such as laser, freezing or burning, etc.).
• Uses: A synthetic diethyl-ether of Estradiol with no distal hormonal effects, in patients undergoing surgical correction for stress urinary incontinence (SUI).

Technology Process of Promestriene

There total 3 articles about Promestriene 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%

17β-methoxyestra-1,3,5(10)-trien-3-ol (100017-39-8,4954-12-5) + propyl bromide (106-94-5) → 3-propoxy-17β-methoxyestra-1,3,5(10)-triene (39219-28-8)

Guidance literature:

With potassium carbonate; potassium iodide; In methanol; at 64 ℃; for 24h;

Reference yield: 90.7%

13-methyl-3-propoxy-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol (22034-63-5) + methyl iodide (74-88-4) → 3-propoxy-17β-methoxyestra-1,3,5(10)-triene (39219-28-8)

Guidance literature:

13-methyl-3-propoxy-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol; With sodium hydroxide; In tetrahydrofuran; for 1h;

methyl iodide; In tetrahydrofuran; for 5h;

Reference yield:

estradiol (50-28-2) → 3-propoxy-17β-methoxyestra-1,3,5(10)-triene (39219-28-8)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen bromide / acetone / 24 h / 55 °C / Inert atmosphere

2: methanol / 12 h / 64 °C / Inert atmosphere

3: potassium iodide; potassium carbonate / methanol / 24 h / 64 °C

With hydrogen bromide; potassium carbonate; potassium iodide; In methanol; acetone; 3: |Williamson Ether Synthesis;

upstream raw materials:

13-methyl-3-propoxy-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

methyl iodide

estradiol

17β-methoxyestra-1,3,5(10)-trien-3-ol

Refernces

• 1、 -. "Synthetic process of prenestyene (by machine translation)". . . Retrieved 2019/10/01.