1-O-(4-Coumaroyl)-beta-D-glucose

Base Information

• Chemical Name: 1-O-(4-Coumaroyl)-beta-D-glucose
• CAS No.: 7139-64-2
• Molecular Formula: C₁₅H₁₈O₈
• Molecular Weight: 326.303
• ChEMBL ID: CHEMBL464612
• Metabolomics Workbench ID: 65718
• Nikkaji Number: J1.678.515F,J322.812F
• Wikidata: Q27139663
• Mol file: 7139-64-2.mol

Synonyms:1-O-(4-Coumaroyl)-beta-D-glucose;7139-64-2;p-coumaroyl glucose;1-O-(4-hydroxycinnamoyl)-beta-D-glucose;p-coumaroyl-beta-D-glucose;1-O-p-Coumaroyl-|A-D-glucose;CHEBI:71498;[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate;1-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranose;(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (E)-3-(4-hydroxyphenyl)acrylate;beta-D-Glucopyranose, 1-(3-(4-hydroxyphenyl)-2-propenoate);CHEMBL464612;SCHEMBL20959521;ACon1_001353;1-O-(4-coumaroyl)-beta-glucose;1-O-(4-coumaroyl)-beta-D-glucoside;FS-8557;HY-W411439;NCGC00180595-01;trans-p-Coumaroyl beta-D-glucopyranoside;1-O-(trans-4-coumaroyl)-beta-D-glucose;CS-0523837;Q27139663;13080-39-2

Chemical Property of 1-O-(4-Coumaroyl)-beta-D-glucose

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 326.10016753
• Heavy Atom Count: 23
• Complexity: 418

Purity/Quality:

98.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)OC2C(C(C(C(O2)CO)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O

Technology Process of 1-O-(4-Coumaroyl)-beta-D-glucose

There total 2 articles about 1-O-(4-Coumaroyl)-beta-D-glucose 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:

acetyl-4-coumaroyl-2,3,4,6-tetraacetyl-β-D-glucose (18449-70-2) → 1-O-p-coumaroyl-β-D-glucopyranose (7139-64-2)

Guidance literature:

acetyl-4-coumaroyl-2,3,4,6-tetraacetyl-β-D-glucose; With sodium methylate; In methanol; for 1.25h; Ice cooling;

In methanol;

DOI:10.1021/jf901204m

Reference yield:

→ 1-O-p-coumaroyl-β-D-glucopyranose (7139-64-2)

Guidance literature:

1-(Acetyl-p-cumaroyl)-2,3,4,6-tetraacetyl-β-D-glucose, Ethanol, NH3;

Reference yield:

1-O-p-coumaroyl-β-D-glucopyranose (7139-64-2) → C15H18O8 + 6‐O‐p‐coumaroyl‐α‐D‐glucose

Guidance literature:

With silica gel; In methanol; dichloromethane;

DOI:10.1021/acs.jafc.6b04074

upstream raw materials:

acetyl-4-coumaroyl-2,3,4,6-tetraacetyl-β-D-glucose