17-beta-Hydroxy Exemestane

Base Information

• Chemical Name: 17-beta-Hydroxy Exemestane
• CAS No.: 122370-91-6
• Deprecated CAS: 122370-91-6
• Molecular Formula: C20H26O2
• Molecular Weight: 298.425
• UNII: U35ZNO9DJH
• ChEMBL ID: CHEMBL3407538
• DSSTox Substance ID: DTXSID00464522
• Nikkaji Number: J2.768.716D
• Wikidata: Q72490426
• Mol file: 122370-91-6.mol

Synonyms:122370-91-6;17-beta-Hydroxy Exemestane;Methylene boldenone;Methylene Boldenone,;CHEMBL3407538;(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-6-methylidene-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-3-one;(1S,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-9a,11a-dimethyl-5-methylidene-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one;3347-73-7;17?-Hydroxy Exemestane;17-beta hydroxy exemestane;17.BETA.-DHE;SCHEMBL1782271;DTXSID00464522;NFDPYPMRHKQTDM-NHWXPXPKSA-N;BDBM50069753;AKOS037645547;AS-6137;PD120010;EXEMESTANE IMPURITY H [EP IMPURITY];17beta-hydroxy-6-methylenandrost-1,4-dien-3-one;17beta-hydroxy-6-methylenandrost-1,4-diene-3-one;6-methylene-17beta-hydroxyandrost-1,4-diene-3-one;17beta-hydroxy-6-methylideneandrosta-1,4-dien-3-one;Androsta-1,4-dien-3-one, 17-hydroxy-6-methylene-, (17|A)-;17.BETA.-HYDROXY-6-METHYLENE-ANDROSTA-1,4-DIENE-3-ONE;ANDROSTA-1,4-DIEN-3-ONE, 17-HYDROXY-6-METHYLENE-, (17.BETA.)-;17beta-Hydroxy-6-methylideneandrosta-1,4-dien-3-one (17beta-Hydroxyexemestane);Androsta-1,4-dien-3-one, 17-hydroxy-6-methylene-, (17?)-;(17?)-17-Hydroxy-6-methyleneandrosta-1,4-dien-3-one;17-Hydroexemestane;Hydroexemestane;17?-Hydroxyexemestane

Chemical Property of 17-beta-Hydroxy Exemestane

Chemical Property:

• Melting Point: 134-136℃
• Refractive Index: 1.581
• Boiling Point: 454.94 °C at 760 mmHg
• Flash Point: 193.73 °C
• PSA: 37.30000
• Density: 1.14g/cm³
• LogP: 3.82130
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 298.193280068
• Heavy Atom Count: 22
• Complexity: 613

Purity/Quality:

98% ^*data from raw suppliers

17β-HydroxyExemestaneSulfamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CC(=C)C4=CC(=O)C=CC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC(=C)C4=CC(=O)C=C[C@]34C
• Description: 17β-hydroxy Exemestane is the primary active metabolite of exemestane . It is formed by metabolism of exemestane by the cytochrome P450 (CYP) isoforms CYP1A and CYP4A11. 17β-hydroxy Exemestane is an aromatase inhibitor (IC50 = 69 nM using human placental microsomes) and an androgen receptor (AR) agonist (IC50 = 39.6 nM) that is selective for AR over estrogen receptor α (ERα; IC50 = 21.2 μM). It stimulates growth of AR- and ERα-positive MCF-7 (EC50 = 2.7 μM) and T47D breast cancer cells (EC50s = 0.43 and 1,500 nM for AR- and ER-mediated growth, respectively) and inhibits proliferation of testosterone-treated aromatase-overexpressing MCF-7aro cells in a concentration-dependent manner. 17β-hydroxy Exemestane (20 mg/kg) inhibits increases in serum cholesterol and LDL levels and prevents decreases in bone mineral density in the lumbar vertebrae and femur, as well as femoral bending strength and compressive strength of the fifth lumbar vertebrae, in ovariectomized rats.
• Uses: A metabolite of Exemestane; exerts biological effects as an androgen. 17β-Hydroxy Exemestane Sulfamate is a metabolite of Exemestane (E957000).

Technology Process of 17-beta-Hydroxy Exemestane

There total 5 articles about 17-beta-Hydroxy Exemestane 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: 95.0%

6-methyleneandrosta-1,4-dien-3-one 17β-acetate (1160599-91-6) → 17β-hydroxy-6-methylen- androsta-1,4-dien-3-one (122370-91-6)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.06.094

Reference yield: 68.4%

17β-hydroxy-6-methyleneandrosta-4-ene-3-one (3347-73-7) → 17β-hydroxy-6-methylen- androsta-1,4-dien-3-one (122370-91-6)

Guidance literature:

With N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil; trifluorormethanesulfonic acid; In toluene; at 108 - 110 ℃; for 4h; Product distribution / selectivity; Heating / reflux;

Reference yield: 39.0%

exemestane (107868-30-4) → 6-methylandrosta-1,4,6-trien-17β-ol + 17β-hydroxy-6-methylen- androsta-1,4-dien-3-one (122370-91-6)

Guidance literature:

With sodium tetrahydroborate; acetic acid; trifluoroacetic acid; In dichloromethane; acetonitrile; at 20 ℃; for 11h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.09.074

upstream raw materials:

formaldehyd

1-dehydrotestosterone

17β-hydroxy-6-methyleneandrosta-4-ene-3-one

6-methyleneandrosta-1,4-dien-3-one 17β-acetate

Downstream raw materials:

6α/β-hydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3,17-dione

FCE₂₇₃₅₃

6-hydroxymethylandrosta-1,4,6-triene-3,17-dione

17β-hydroxy-6α/β-spirooxiranandrosta-1,4-dien-3-one

Refernces

• 1、 -. "Process for obtaining 6-Alkylidenandrost-1,4-diene-3one". Page/Page column 9. . Retrieved 2009/07/10.
• 2、 Buzzetti,Di Salle,Longo,Briatico. "Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione)". . p. 527 - 532. Retrieved 2007/10/02.