1-Salicylate glucuronide

Base Information

• Chemical Name: 1-Salicylate glucuronide
• CAS No.: 7695-70-7
• Molecular Formula: C13H14O9
• Molecular Weight: 0
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID20227737
• Nikkaji Number: J397.582G
• Wikidata: Q27144282
• Metabolomics Workbench ID: 40869
• ChEMBL ID: CHEMBL1371375
• Mol file: 7695-70-7.mol

Synonyms:1-salicylate glucuronide;phenolic SA glucuronide;salicyl phenolic glucuronide;salicylphenolic glucuronide

Chemical Property of 1-Salicylate glucuronide

Chemical Property:

• Melting Point: 131-133°C
• PSA: 153.75000
• LogP: -1.34420
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly, Heated), Water (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 314.06378202
• Heavy Atom Count: 22
• Complexity: 426

Purity/Quality:

97% ^*data from raw suppliers

Salicylic acid phenolic D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)OC2C(C(C(C(O2)C(=O)O)O)O)O
• Isomeric SMILES: C1=CC=C(C(=C1)C(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Uses: Salicylic Acid β-D-O-Glucuronide is a metabolite of Acetylsalicylic Acid (Aspirin) (A187780). A metabolite of Aspirin

Technology Process of 1-Salicylate glucuronide

There total 6 articles about 1-Salicylate 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:

D-(-)-salicin (138-52-3) → Salicylic acid phenol glucuronide (7695-70-7,31566-22-0,7696-34-6,96750-93-5)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Carbonate buffer; at 20 ℃; Yield given; electrochemical reaction: platinum foil anode and a graphite cathode, saturated calomel electrode as reference electrode (Hg/Hg₂Cl₂/saturated KCl in H₂O, +0.20 V vs. SCE), electrolysis at a potential of 0.53 V vs. SCE, charge consumption of 11.2 F/mol;

DOI:10.1055/s-1999-3464

Reference yield:

O2,O3,O4-triacetyl-O1-(2-methoxycarbonyl-phenyl)-β-D-glucopyranuronic acid methyl ester (101231-54-3) → Salicylic acid phenol glucuronide (7695-70-7,31566-22-0,7696-34-6,96750-93-5)

Guidance literature:

With barium dihydroxide; water;

DOI:10.1021/jo01111a603

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → Salicylic acid phenol glucuronide (7695-70-7,31566-22-0,7696-34-6,96750-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: silver oxide; isoquinoline

2: barium hydroxide; water

With isoquinoline; barium dihydroxide; water; silver(l) oxide;

DOI:10.1021/jo01111a603

upstream raw materials:

O²,O³,O⁴-triacetyl-O¹-(2-methoxycarbonyl-phenyl)-β-D-glucopyranuronic acid methyl ester

D-(-)-salicin

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

methyl salicylate

Refernces