Estradiol-17beta-glucuronide

Base Information

• Chemical Name: Estradiol-17beta-glucuronide
• CAS No.: 1806-98-0
• Deprecated CAS: 21809-63-2,125926-20-7,27851-73-6,21809-48-3,30137-07-6
• Molecular Formula: C24H32O8
• Molecular Weight: 448.513
• Hs Code.: 2938909090
• ChEMBL ID: CHEMBL1697724
• DSSTox Substance ID: DTXSID50862756
• Metabolomics Workbench ID: 36922
• Nikkaji Number: J386.923G
• Wikidata: Q26998368
• Wikipedia: Estradiol_glucuronide
• Mol file: 1806-98-0.mol

Synonyms:17 beta-estradiol glucuronide;17beta-estradiol-17-(beta-D-glucuronide);betaestradiol 17-(beta-D-glucuronide);E(2)17G cpd;E217G cpd;estradiol-17 beta-glucuronide;estradiol-17 beta-glucuronide, monosodium salt;estradiol-17beta-D-glucuronide;estradiol-17beta-glucuronide;oestradiol-17beta-glucuronide

Chemical Property of Estradiol-17beta-glucuronide

Chemical Property:

• Vapor Pressure: 2.34E-20mmHg at 25°C
• Melting Point: 198-202 °C
• Boiling Point: 696.4°Cat760mmHg
• PKA: 2.82±0.70(Predicted)
• Flash Point: 239.3°C
• PSA: 136.68000
• Density: 1.44g/cm³
• LogP: 1.52570
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 448.20971797
• Heavy Atom Count: 32
• Complexity: 716

Purity/Quality:

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

17β-Estradiol17β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2OC4C(C(C(C(O4)C(=O)O)O)O)O)CCC5=C3C=CC(=C5)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)CCC5=C3C=CC(=C5)O
• Uses: A metabolite of Estradiol (E888000).

Technology Process of Estradiol-17beta-glucuronide

There total 7 articles about Estradiol-17beta-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:

methyl 3-hydroxyestra-1,3,5(10)-trien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosuronate (14364-66-0) → estradiol-17-β-D-glucuronide (1806-98-0)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1021/ja01516a046

Reference yield:

α-D-glucuronyl fluoride (777038-38-7) + estradiol (50-28-2) → estra-1,3,5(10)-triene-3,17β-diol 3,17-O-bisglucuronide (36589-47-6) + estradiol 3-O-glucuronide (15270-30-1,17263-23-9,21343-42-0,63307-54-0) + estradiol-17-β-D-glucuronide (1806-98-0)

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:

estradiol (50-28-2) + UDP-glucuronic acid (1245697-26-0,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1) → estradiol 3-O-glucuronide (15270-30-1,17263-23-9,21343-42-0,63307-54-0) + estradiol-17-β-D-glucuronide (1806-98-0)

Guidance literature:

With β‐cyclodextrin; magnesium chloride; In methanol; at 37 ℃; aq. buffer; Enzymatic reaction;

DOI:10.1248/cpb.58.354

upstream raw materials:

methyl 3-hydroxyestra-1,3,5(10)-trien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosuronate

estradiol

uridine-diphosphate-glucuronic acid triammonium salt

UDP-glucuronic acid

Downstream raw materials:

estradiol

D-glucuronic acid

Refernces

• 1、 Kashima, Yousuke,Kitade, Takashi,Kashima, Yuuko,Okabayashi, Yoshito. "Development of an automated synthesis system for preparation of glucuronides using a solid-phase extraction column loaded with microsomes". experimental part. p. 354 - 358. Retrieved 2011/02/22.
• 2、 Nambara,Numazawa. "Studies on metabolism of 3-deoxysteroids. 8. Isolation and characterization of conjugated metabolites of 3-deoxyestrone.". . p. 990 - 994. Retrieved 2007/10/11.