Estrone glucuronide

Base Information

• Chemical Name: Estrone glucuronide
• CAS No.: 2479-90-5
• Deprecated CAS: 26610-40-2,30137-08-7
• Molecular Formula: C24H30 O8
• Molecular Weight: 446.497
• Hs Code.: 2938909090
• UNII: 933Q277TO2
• DSSTox Substance ID: DTXSID20891497
• Nikkaji Number: J468.255F
• Wikipedia: Estrone_glucuronide
• Wikidata: Q27271553
• Metabolomics Workbench ID: 36909
• ChEMBL ID: CHEMBL1232444
• Mol file: 2479-90-5.mol

Synonyms:estrone-3-glucosiduronate;estrone-3-glucuronide

Chemical Property of Estrone glucuronide

Chemical Property:

• Vapor Pressure: 8.67E-21mmHg at 25°C
• Boiling Point: 703.8°Cat760mmHg
• PKA: 2.80±0.70(Predicted)
• Flash Point: 242.9°C
• PSA: 133.52000
• Density: 1.419g/cm³
• LogP: 1.38280
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 446.19406791
• Heavy Atom Count: 32
• Complexity: 756

Purity/Quality:

99% ^*data from raw suppliers

1,3,5(10)-ESTRATRIEN-3-OL-17-ONE GLUCOSIDURONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)OC5C(C(C(C(O5)C(=O)O)O)O)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
• Uses: A metabolite of 17 -Estradiol Estrone β-D-Glucuronide is a metabolite of 17β -Estradiol (E888000), the major estrogen (1) secreted by the premenopausal ovary (2).

Technology Process of Estrone glucuronide

There total 5 articles about Estrone glucuronide 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: 94.0%

methyl {(17-oxo-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (27537-72-0) → Estrone O3-glucuronide (2479-90-5,26610-40-2,30137-08-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃;

DOI:10.1080/07328309908544025

Reference yield:

α-D-glucuronyl fluoride (777038-38-7) + Estrone (53-16-7) → Estrone O3-glucuronide (2479-90-5,26610-40-2,30137-08-7)

Guidance literature:

With Escherichia coli β-glucuronidase E504G mutant; In aq. phosphate buffer; tert-butyl alcohol; at 37 ℃; for 48h; pH=7.5; Enzymatic reaction;

DOI:10.1039/c4ob00984c

Reference yield:

Estrone (53-16-7) → Estrone O3-glucuronide (2479-90-5,26610-40-2,30137-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 20 °C

2: 94 percent / sodium hydroxide / methanol / 20 °C

With sodium hydroxide; boron trifluoride diethyl etherate; In methanol; dichloromethane; 1: glucuronidation / 2: Hydrolysis;

DOI:10.1080/07328309908544025

upstream raw materials:

methyl {(17-oxo-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

Estrone

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

α-D-glucuronyl fluoride

Downstream raw materials:

D-glucuronic acid

Estrone