Estradiol

Base Information

• Chemical Name: Estradiol
• CAS No.: 17916-67-5
• Deprecated CAS: 873662-39-6,1050677-52-5,1206475-11-7,1050677-52-5,1206475-11-7
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.387
• European Community (EC) Number: 200-023-8
• NSC Number: 9895
• UNII: 4TI98Z838E
• DSSTox Substance ID: DTXSID0020573
• Nikkaji Number: J4.100I
• Wikipedia: Estradiol
• Wikidata: Q422416
• NCI Thesaurus Code: C478,C2295
• RXCUI: 4083
• Pharos Ligand ID: M3TNLZD5Z8Y9
• Metabolomics Workbench ID: 35273
• ChEMBL ID: CHEMBL135
• Mol file: 17916-67-5.mol

Synonyms:17 beta Estradiol;17 beta Oestradiol;17 beta-Estradiol;17 beta-Oestradiol;Aerodiol;Delestrogen;Estrace;Estraderm TTS;Estradiol;Estradiol 17 alpha;Estradiol 17 beta;Estradiol 17beta;Estradiol Anhydrous;Estradiol Hemihydrate;Estradiol Hemihydrate, (17 alpha)-Isomer;Estradiol Monohydrate;estradiol valerate;estradiol valeriante;Estradiol, (+-)-Isomer;Estradiol, (-)-Isomer;Estradiol, (16 alpha,17 alpha)-Isomer;Estradiol, (16 alpha,17 beta)-Isomer;Estradiol, (17-alpha)-Isomer;Estradiol, (8 alpha,17 beta)-(+-)-Isomer;Estradiol, (8 alpha,17 beta)-Isomer;Estradiol, (9 beta,17 alpha)-Isomer;Estradiol, (9 beta,17 beta)-Isomer;Estradiol, Monosodium Salt;Estradiol, Sodium Salt;Estradiol-17 alpha;Estradiol-17 beta;Estradiol-17beta;Oestradiol;Ovocyclin;Progynon Depot;Progynon-Depot;Progynova;Vivelle

Chemical Property of 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
• Recent ClinicalTrials: Treating Postmenopausal Dyspareunia Where it Hurts
• Recent EU Clinical Trials: The effect of low-dose rhythmic 17-β-estradiol administration on bone turnover in postmenopausal women
• Recent NIPH Clinical Trials: Clinical trial of the Estrogen replacement effect on Physical Performance to muscle resistance exercise for elderly with Osteoarthritis of Knee joint.

Technology Process of Estradiol

There total 25 articles about 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

2-chloro-17β-oestradiol

2-bromo-17β-oestradiol

2-iodo-17β-oestradiol

Refernces

• 1、 Quinkert,Weber,Schwartz,et al.. "Highly selective total synthesis of 19-nor-steroids via a photochemical key reaction: Racemic target compounds". . p. 2335 - 2371. Retrieved 2007/10/02.
• 2、 Kametani,Matsumoto,Nemoto,Fukumoto. "Asymmetric total synthesis of estradiol by an intramolecular cycloaddition of benzocyclobutene derivative". . p. 6218 - 6220. Retrieved 2007/10/06.