Vanilloside

Base Information

• Chemical Name: Vanilloside
• CAS No.: 494-08-6
• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.292
• UNII: H81U1KBS6E
• DSSTox Substance ID: DTXSID00197782
• Nikkaji Number: J676.333B
• Wikidata: Q27279742
• Mol file: 494-08-6.mol

Synonyms:glucovanillin

Chemical Property of Vanilloside

Chemical Property:

• Vapor Pressure: 4.75E-14mmHg at 25°C
• Melting Point: 189-190°
• Refractive Index: 1.628
• Boiling Point: 574.7 °C at 760 mmHg
• PKA: 12.78±0.70(Predicted)
• Flash Point: 216.6 °C
• PSA: 125.68000
• Density: 1.481g/cm³
• LogP: -1.31360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 314.10016753
• Heavy Atom Count: 22
• Complexity: 365

Purity/Quality:

98.0%min ^*data from raw suppliers

Vanillin 4-O-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=O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Vanillin 4-O-β-D-Glucoside is the glucosylated precursor of Vanillin (V097500) found in the seed pods of Vanilla planifola. During the curing process Vanillin 4-O-β-D-Glucoside is transformed into the aromatic vanillin.

Technology Process of Vanilloside

There total 16 articles about Vanilloside 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: 94.0%

4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin (51482-43-0,70631-03-7,70631-04-8,23598-07-4) → glucovanillin (494-08-6,70622-71-8,70622-72-9,83662-01-5)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; water; at 40 ℃; for 0.333333h;

DOI:10.1016/j.carres.2018.02.015

Reference yield: 86.0%

citrusin C (18604-50-7) → glucovanillin (494-08-6,70622-71-8,70622-72-9,83662-01-5)

Guidance literature:

With 1,4-bis(dimethylsilyl)benzene; iron(II) 3-oxo-1,3-diphenylprop-1-en-1-olate; In ethyl acetate; for 12h; Reflux;

Reference yield:

β-D-glucose pentaacetate (604-69-3) → glucovanillin (494-08-6,70622-71-8,70622-72-9,83662-01-5)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; hydrogen bromide; acetic anhydride / 2 h / 20 °C / Inert atmosphere

2: toluene / 3 h / Inert atmosphere; Reflux

3: boron trifluoride diethyl etherate / dichloromethane / 1 h

4: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; hydrogen bromide; sodium methylate; acetic anhydride; acetic acid; In methanol; dichloromethane; toluene;

DOI:10.1055/s-0035-1561461

upstream raw materials:

vanillin

Sucrose

D-Glucose

UDP-glucose

Downstream raw materials:

1-<4-β-Glucopyranosyl-3-methoxy>-3-<2-hydroxy-4,6-dimethoxy-phenyl>-prop-1-en-3-on

4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside

4-β-D-glucopyranosyloxy-3-methoxy-benzaldehyde thiosemicarbazone

4'-formyl-2'-methoxyphenyl 4,6-O-(α-amylcinnamylidene)-β-D-glucopyranoside

Refernces

• 1、 -. "Ice recrystallization inhibitor". Paragraph 0095-0096. . Retrieved 2021/12/07.
• 2、 -. "Method for synthesizing aromatic aldehyde through iron catalyzed oxidation allyl aromatic compound". Paragraph 0081-0083; 0150. . Retrieved 2019/06/27.