16alpha,17beta-Estriol 17-(beta-D-glucuronide)

Base Information

• Chemical Name: 16alpha,17beta-Estriol 17-(beta-D-glucuronide)
• CAS No.: 7219-89-8
• Molecular Formula: C24H32 O9
• Molecular Weight: 464.513
• European Community (EC) Number: 635-343-0
• ChEMBL ID: CHEMBL1417173
• DSSTox Substance ID: DTXSID50992906
• Metabolomics Workbench ID: 36931
• Nikkaji Number: J745.319A
• Wikidata: Q27105356
• Mol file: 7219-89-8.mol

Synonyms:estriol 17-glucuronide

Chemical Property of 16alpha,17beta-Estriol 17-(beta-D-glucuronide)

Chemical Property:

• Vapor Pressure: 6.95E-23mmHg at 25°C
• Boiling Point: 738.3°C at 760 mmHg
• Flash Point: 253.5°C
• PSA: 156.91000
• LogP: 0.49650
• Storage Temp.: −20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 464.20463259
• Heavy Atom Count: 33
• Complexity: 747

Purity/Quality:

97% ^*data from raw suppliers

ESTRIOL 17BETA-(BETA-D-GLUCURONIDE) 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC(C2OC4C(C(C(C(O4)C(=O)O)O)O)O)O)CCC5=C3C=CC(=C5)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)CCC5=C3C=CC(=C5)O

Technology Process of 16alpha,17beta-Estriol 17-(beta-D-glucuronide)

There total 13 articles about 16alpha,17beta-Estriol 17-(beta-D-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: 65.0%

methyl 1-O-<3,16α-dihydroxy-estra-1,3,5(10)-trien-17β-yl>-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (18842-02-9) → 3,16α-dihydroxy-1,3,5(10)-estratrien-17β-yl-β-D-glucopyranosiduronic acid (7219-89-8)

Guidance literature:

With sodium hydroxide; In methanol; for 24h; Ambient temperature;

DOI:10.1016/0039-128X(93)90001-4

Reference yield: 65.0%

methyl 3-acetoxy-16α-hydroxy-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (39130-74-0) → 3,16α-dihydroxy-1,3,5(10)-estratrien-17β-yl-β-D-glucopyranosiduronic acid (7219-89-8)

Guidance literature:

With sodium hydroxide; In methanol; for 24h; Ambient temperature;

DOI:10.1016/0039-128X(93)90001-4

Reference yield:

Uridine diphospho-D-glucuronic acid triammonium salt (63700-19-6) + Estriol (50-27-1,300853-07-0) → Estriol O3-glucuronide (2479-91-6) + 3,16α-dihydroxy-1,3,5(10)-estratrien-17β-yl-β-D-glucopyranosiduronic acid (7219-89-8) + estriol-16α-D-glucoronide (1852-50-2)

Guidance literature:

With magnesium chloride; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; pH=7.4; regioselective reaction; Enzymatic reaction;

DOI:10.1124/dmd.112.049072

upstream raw materials:

methyl 1-O-<3,16α-dihydroxy-estra-1,3,5(10)-trien-17β-yl>-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate

methyl 3-acetoxy-16α-hydroxy-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate

Estriol

uridine-5'-diphospho-α-D-glucuronic acid trisodium salt

Downstream raw materials:

D-glucuronic acid

Estriol

Refernces

• 1、 Bichlmaier, Ingo,Kurkela, Mika,Siiskonen, Antti,Finel, Moshe,Yli-Kauhaluoma, Jari. "Eudismic analysis of tricyclic sesquiterpenoid alcohols: Lead structures for the design of potent inhibitors of the human UDP-glucuronosyltransferase 2B7". . p. 386 - 400. Retrieved 2008/03/27.
• 2、 Nambara,Imai. "Syntheses of estriol monoglucuronides.". . p. 1232 - 1238. Retrieved 2007/10/10.