Estradiol 3-methyl ether

Base Information

• Chemical Name: Estradiol 3-methyl ether
• CAS No.: 1035-77-4
• Deprecated CAS: 30308-16-8,40135-21-5
• Molecular Formula: C19H26 O2
• Molecular Weight: 286.414
• European Community (EC) Number: 213-858-8
• NSC Number: 58851
• UNII: 0BQ383G656
• DSSTox Substance ID: DTXSID001313230
• Nikkaji Number: J79.397C
• ChEMBL ID: CHEMBL116468
• Mol file: 1035-77-4.mol

Synonyms:3-methoxy-17 beta-estradiol;E2 methyl;estradiol-17 beta-3-methyl ether;estradiol-17 beta-3-methyl ether, ((13alpha,17alpha)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((13alpha,17beta)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((14beta,17alpha)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((17alpha)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((17beta)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((8alpha,14beta,17alpha)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((8alpha,17alpha)-(+-))-isomer;estradiol-17 beta-3-methyl ether, ((8alpha,17beta)-(+-))-isomer;estradiol-17 beta-3-methyl ether, (17alpha)-isomer;estradiol-17 beta-3-methyl ether, (8alpha,17beta)-isomer;estradiol-17 beta-3-methyl ether, (8alpha,9beta,13alpha,14beta,17alpha)-isomer;estradiol-17 beta-3-methyl ether, (8xi,9xi,17beta)-isomer;estradiol-17 beta-3-methyl ether, (9beta,17beta)-isomer;estradiol-17 beta-3-methyl ether, hemihydrate, (17beta)-isomer

Chemical Property of Estradiol 3-methyl ether

Chemical Property:

• Melting Point: 120-121 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Refractive Index: 1.4709 (estimate)
• Boiling Point: 428.8 °C at 760 mmHg
• PKA: 15.07±0.40(Predicted)
• Flash Point: 187.9 °C
• PSA: 29.46000
• Density: 1.109 g/cm³
• LogP: 3.91220
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 286.193280068
• Heavy Atom Count: 21
• Complexity: 395

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-O-MethylEstradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F
• Hazard Codes: Xn,F
• Statements: 20/21/22-36-11
• Safety Statements: 22-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC
• Uses: Labelled Estradiol derivative which shows antioxidant activity.

Technology Process of Estradiol 3-methyl ether

There total 96 articles about Estradiol 3-methyl ether 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: 97.0%

estradiol (50-28-2) + methyl iodide (74-88-4) → 3-O-methyl-17β-oestradiol (1035-77-4)

Guidance literature:

With sodium carbonate; In methanol; for 64h; Reflux; Inert atmosphere;

DOI:10.1016/j.steroids.2014.04.009

Reference yield: 96.0%

estrone 3-methyl ether (1624-62-0) → 3-O-methyl-17β-oestradiol (1035-77-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1016/j.steroids.2014.04.009

Reference yield: 87.0%

(8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (4954-14-7) → 3-O-methyl-17β-oestradiol (1035-77-4)

Guidance literature:

With aluminium trichloride; sodium iodide; In dichloromethane; acetonitrile; for 5.5h; Ambient temperature;

upstream raw materials:

formaldehyd

estrone 3-methyl ether

Estrone

estradiol

Downstream raw materials:

benzoic acid-(3-methoxy-estratrien-(A)-yl-(17β)-ester)

Benzoic acid (8R,9S,13S,14S,17S)-4-benzoyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester

3-methoxy-17β-sulfooxyestra-1,3,5(10)-triene triethylammonium salt

estradiol

Refernces

• 1、 Hayashi, Yujiro,Koshino, Seitaro,Ojima, Kanna,Kwon, Eunsang. "Pot Economy in the Total Synthesis of Estradiol Methyl Ether by Using an Organocatalyst". . p. 11812 - 11815. Retrieved 2017.
• 2、 Miller, Thomas A.,Bulman, Amanda L.,Thompson, Charles D.,Garst, Michael E.,Macdonald, Timothy L.. "The synthesis and evaluation of functionalized estratropones: Potent inhibitors of tubulin polymerization". . p. 1851 - 1856. Retrieved 1997.
• 3、 Romanov-Michailidis, Fedor,Ravetz, Benjamin D.,Paley, Daniel W.,Rovis, Tomislav. "Ir(III)-Catalyzed Carbocarbation of Alkynes through Undirected Double C-H Bond Activation of Anisoles". . p. 5370 - 5374. Retrieved 2018.
• 4、 Adamecz, Dóra Izabella,Frank, éva,Kiricsi, Mónika,Krishna Gopisetty, Mohana,Molnár, Barnabás. "Multistep Synthesis and in Vitro Anticancer Evaluation of 2-Pyrazolyl-Estradiol Derivatives, Pyrazolocoumarin-Estradiol Hybrids and Analogous Compounds". . . Retrieved 2020.
• 5、 Laing,Sykes. "". . p. 2915. Retrieved 1968.
• 6、 Schmidt,Prezewowsky,Schulz,Wiechert. "15-beta, 16-beta-methylene-steroids". . p. 939 - 943. Retrieved 1968.
• 7、 Goendoes, Gyoergy,Wittman, Gyula,Bartok, Mihaly,Orr, James C.. "Chiral hydrogenation of estrone-3-methyl ether on modified Raney nickel catalysts". . p. 533 - 535. Retrieved 1993.
• 8、 Cohen,Cook,Hewett. "-". . p. 445,451. Retrieved 1935.
• 9、 Ciuffreda,Casati,Manzocchi. "Complete 1H and 13C NMR spectral assignment of 17-hydroxy epimeric sterols with planar A or A and B rings.". . p. 360 - 363. Retrieved 2004.
• 10、 Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng. "Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation". supporting information. p. 4018 - 4022. Retrieved 2021/05/26.