1-O-Feruloylglucose

Base Information

• Chemical Name: 1-O-Feruloylglucose
• CAS No.: 7196-71-6
• Molecular Formula: C16H20O9
• Molecular Weight: 356.329
• Mol file: 7196-71-6.mol

Synonyms:1-O-Feruloylglucose;[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate;Feruloyl Hexoside (isomer of 847);SCHEMBL15711514;CHEBI:168886

Chemical Property of 1-O-Feruloylglucose

Chemical Property:

• PSA: 145.91000
• LogP: -1.24290
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 356.11073221
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

97% ^*data from raw suppliers

FerulicAcidAcyl-β-D-glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(C(O2)CO)O)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)OC2C(C(C(C(O2)CO)O)O)O)O
• Uses: Ferulic Acid Acyl-β-D-glucoside is a metabolite of Ferulic Acid (F308900).

Technology Process of 1-O-Feruloylglucose

There total 7 articles about 1-O-Feruloylglucose 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: 78.0%

1-O-β-(4-O-chloroacetylferuloyl)-2,3,4,6-tetra-O-chloroacetylglucose → 4'-hydroxy-3'-methoxycinnamoyl-β-D-glucopyranose (7196-71-6)

Guidance literature:

With pyridine; water; at 20 ℃; for 36h;

DOI:10.1016/j.tetlet.2011.05.038

Reference yield:

UDP-glucose (133-89-1) + 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → 4'-hydroxy-3'-methoxycinnamoyl-β-D-glucopyranose (7196-71-6)

Guidance literature:

With recombinant Quercus robur UGT₈₄A₁₃; In glycerol; at 30 ℃; pH=6; Enzymatic reaction;

DOI:10.1016/j.phytochem.2013.11.023

Reference yield:

C25H28O14 → 4'-hydroxy-3'-methoxycinnamoyl-β-D-glucopyranose (7196-71-6)

Guidance literature:

C₂₅H₂₈O₁₄; With sodium methylate; In methanol; Ice cooling;

In methanol;

DOI:10.1021/jf901204m

upstream raw materials:

2,3,4,6-tetra-O-chloroacetylglucosyl trichloroacetimidate

2,3,4,6-tetra-O-chloroacetyl-D-glucopyranose

1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose

UDP-glucose

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