ent-Estradiol

Base Information

• Chemical Name: ent-Estradiol
• CAS No.: 3736-22-9
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.387
• UNII: VW299DJ6U7
• DSSTox Substance ID: DTXSID60912332
• Nikkaji Number: J39.482C
• Wikipedia: Ent-Estradiol
• Wikidata: Q81988384
• Mol file: 3736-22-9.mol

Synonyms:ent-Estradiol;1-Estradiol;ent-E2;Estradiol, (-)-;(-)-ESTRADIOL;VW299DJ6U7;ent-17beta-Estradiol;3736-22-9;UNII-VW299DJ6U7;1-E2;J-855;SCHEMBL7260525;ENT-17.BETA.-ESTRADIOL;DTXSID60912332;8alpha,9beta,13alpha,14beta-Estra-1,3,5(10)-triene-3,17alpha-diol;(8alpha,9beta,13alpha,14beta,17alpha)-Estra-1,3,5(10)-triene-3,17-diol;8.ALPHA.,9.BETA.,13.ALPHA.,14.BETA.-ESTRA-1,3,5(10)-TRIENE-3,17.ALPHA.-DIOL;Estra-1,3,5(10)-triene-3,17-diol, (8alpha,9beta,13alpha,14beta,17alpha)-;(8.ALPHA.,9.BETA.,13.ALPHA.,14.BETA.,17.ALPHA.)-ESTRA-1,3,5(10)-TRIENE-3,17-DIOL;ESTRA-1,3,5(10)-TRIENE-3,17-DIOL, (8.ALPHA.,9.BETA.,13.ALPHA.,14.BETA.,17.ALPHA.)-

Chemical Property of ent-Estradiol

Chemical Property:

• PSA: 40.46000
• LogP: 3.60920
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 272.177630004
• Heavy Atom Count: 20
• Complexity: 382

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@@H]([C@H]1CC[C@H]2O)CCC4=C3C=CC(=C4)O

Technology Process of ent-Estradiol

There total 35 articles about ent-Estradiol 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: 83.0%

2,2-Dimethyl-propionic acid (8R,9S,13S,14S,17S)-3-acetoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester → (+/-)-estradiol (50-28-2,57-91-0,517-04-4,3736-22-9,5864-38-0,15426-99-0,15427-00-6,17916-67-5,19669-82-0,53177-70-1,66514-24-7,70285-89-1,83198-25-8,95463-67-5,98920-17-3,145164-84-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/0040-4039(95)00754-Z

Reference yield:

→ D,L-8-Isooestradiol (50-28-2,57-91-0,517-04-4,3736-22-9,5864-38-0,15426-99-0,15427-00-6,17916-67-5,19669-82-0,53177-70-1,66514-24-7,70285-89-1,83198-25-8,95463-67-5,98920-17-3,145164-84-7)

Guidance literature:

With sodium hydroxide; nickel; at 85 ℃; Hydrogenation_.unter Druck;

DOI:10.1021/ja01536a040

Reference yield:

4-methoxysalicylaldehyde (52289-54-0) → (+/-)-estradiol (50-28-2,57-91-0,517-04-4,3736-22-9,5864-38-0,15426-99-0,15427-00-6,17916-67-5,19669-82-0,53177-70-1,66514-24-7,70285-89-1,83198-25-8,95463-67-5,98920-17-3,145164-84-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Mg / 1) THF; 2) ether, 12 h at room temp.

2: 75 percent / Mn(IV) oxide / petroleum ether / 2 h

With manganese(IV) oxide; magnesium; In Petroleum ether;

DOI:10.1002/jlac.198119811220

upstream raw materials:

(+/-)-oestrone

rac-3-Methoxy-6,7:8,9-diseco-1,3,5⁽¹⁰⁾,7-oestratetraen-9,17-dion

4-methoxysalicylaldehyde

4-bromo-3-methylanisole

Downstream raw materials:

17β-oestradiol diacetate

17-β-estradiol 17-acetate

2-iodo-17β-oestradiol

2-bromo-17β-oestradiol