16-Glucuronide-estriol

Base Information

• Chemical Name: 16-Glucuronide-estriol
• CAS No.: 1852-50-2
• Molecular Formula: C24H32 O9
• Molecular Weight: 464.513
• European Community (EC) Number: 633-751-3
• DSSTox Substance ID: DTXSID30939935
• Nikkaji Number: J459.851B
• Wikipedia: Estriol_glucuronide
• Wikidata: Q27105354
• Metabolomics Workbench ID: 36906
• ChEMBL ID: CHEMBL2074802
• Mol file: 1852-50-2.mol

Synonyms:3,17 beta-dihydroxy-1,3,5(10)-estratrien-16 alpha-yl-beta-D-glucopyranosiduronic acid;estriol-16 alpha-(beta-D-glucuronide);estriol-16 alpha-(beta-D-glucuronide), sodium salt;estriol-16 alpha-glucosiduronate;estriol-16 alpha-glucuronide;estriol-16-(beta-D-glucuronide), (16beta,17beta)-isomer;estriol-16-glucosiduronate;estriol-16alpha-(beta-D-glucuronide);estriol-16alpha-glucuronide;oestriol-16alpha-glucuronide

Chemical Property of 16-Glucuronide-estriol

Chemical Property:

• Vapor Pressure: 6.95E-23mmHg at 25°C
• Boiling Point: 738.3°Cat760mmHg
• PKA: 2.82±0.70(Predicted)
• Flash Point: 253.5°C
• PSA: 156.91000
• Density: 1.51g/cm³
• 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:

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

Estriol 16α-(β-D-glucuronide) ≥97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CC(C2O)OC4C(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]1C[C@H]([C@@H]2O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)CCC5=C3C=CC(=C5)O

Technology Process of 16-Glucuronide-estriol

There total 11 articles about 16-Glucuronide-estriol 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 3,17β-diacetoxy-1,3,5(10)-estratrien-16α-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (153003-10-2) → estriol-16α-D-glucoronide (1852-50-2)

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-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

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

Estriol

16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-3,17β-diol

3,17β-diacetoxy-1,3,5(10)-estratrien-16α-ol

Downstream raw materials:

N-(6-benzyloxycarbonylaminohexyl)-(3,17β-dihydroxy-1,3,5(10)-estratrien-16α-yl-β-D-glucopyranosid)uronamide

estriol-16α-glucuronide aminobutyl ethyl isoluminol conjugate

D-glucuronic acid

Estriol

Refernces

• 1、 Sneitz, Nina,Vahermo, Mikko,Mosorin, Johanna,Laakkonen, Liisa,Poirier, Donald,Finel, Moshe. "Regiospecificity and stereospecificity of human udpglucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiols". . p. 582 - 591. Retrieved 2013.