Orcinol glucoside

Base Information

• Chemical Name: Orcinol glucoside
• CAS No.: 21082-33-7
• Molecular Formula: C13H18O7
• Molecular Weight: 286.27800
• European Community (EC) Number: 803-274-7
• ChEMBL ID: CHEMBL2425246
• Metabolomics Workbench ID: 129162
• Nikkaji Number: J2.167.220C
• Wikidata: Q104399438
• Mol file: 21082-33-7.mol

Synonyms:Orcinol glucoside;Sakakin;21082-33-7;ORCINOLGLUCOSIDE;beta-D-Glucopyranoside, 3-hydroxy-5-methylphenyl;SCHEMBL2997824;CHEMBL2425246;orcinol-O-beta-d-glucopyranoside;CHEBI:182737;HY-N0008;MFCD06794970;AKOS037514763;Sakakin, >=95% (LC/MS-ELSD);NCGC00384645-01;CS-0007089;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(3-hydroxy-5-methylphenoxy)oxane-3,4,5-triol;NCGC00384645-01_C13H18O7_3-Hydroxy-5-methylphenyl beta-D-glucopyranoside

Chemical Property of Orcinol glucoside

Chemical Property:

• Melting Point: 138 °C(Solv: methanol (67-56-1); ethanol (64-17-5))
• Boiling Point: 570.6±50.0 °C(Predicted)
• PKA: 9.55±0.10(Predicted)
• PSA: 119.61000
• Density: 1.497
• LogP: -1.12070
• Storage Temp.: ?20°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 286.10525291
• Heavy Atom Count: 20
• Complexity: 313

Purity/Quality:

99.5% ^*data from raw suppliers

Orcinolglucoside ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)OC2C(C(C(C(O2)CO)O)O)O)O
• Isomeric SMILES: CC1=CC(=CC(=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• Uses: Orcinol Glucoside produces antidepressant effects blocking behavioural and neuronal deficits.

Technology Process of Orcinol glucoside

There total 4 articles about Orcinol glucoside 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:

3-hydroxy-5-methylphenyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside) → 3-hydroxy-5-methylphenyl (β-D-glucopyranoside) (21082-33-7)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 24h;

Reference yield:

orcinol (504-15-4) + β-D-glucose pentaacetate (604-69-3) → 3-hydroxy-5-methylphenyl (β-D-glucopyranoside) (21082-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate; triethylamine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2: methanol; sodium methylate / 24 h / 20 °C

With methanol; boron trifluoride diethyl etherate; sodium methylate; triethylamine; In dichloromethane;

Reference yield:

orcinol (504-15-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3-hydroxy-5-methylphenyl (β-D-glucopyranoside) (21082-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / water / 0.5 h

1.2: 3.5 h / 20 °C

2.1: methanol; sodium methylate / 24 h / 20 °C

With methanol; sodium methylate; sodium hydroxide; In water;

upstream raw materials:

orcinol

β-D-glucose pentaacetate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

orcinol

Refernces

• 1、 -. "PHENOL GLYCOSIDES AND THEIR USE IN THE TREATMENT OF UROLITHIASIS". Page/Page column 26; 27; 28. . Retrieved 2017/01/26.