Sinapaldehyde glucoside

Base Information

• Chemical Name: Sinapaldehyde glucoside
• CAS No.: 154461-65-1
• Molecular Formula: C₁₇H₂₂O₉
• Molecular Weight: 370.356
• Mol file: 154461-65-1.mol

Synonyms:2-Propenal,3-[4-(b-D-glucopyranosyloxy)-3,5-dimethoxyphenyl]-,(E)-

Chemical Property of Sinapaldehyde glucoside

Chemical Property:

• Melting Point: 221-223 °C
• Boiling Point: 633.5±55.0 °C(Predicted)
• PKA: 12.71±0.70(Predicted)
• PSA: 134.91000
• Density: 1.409±0.06 g/cm3(Predicted)
• LogP: -0.90540
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Sinapaldehydeglucoside 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Sinapaldehyde glucoside

There total 7 articles about Sinapaldehyde 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: 79.0%

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde (203179-62-8) → sinapyl aldehyde 4-O-β-D-glucopyranoside (154461-65-1)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 20 ℃; for 4h;

DOI:10.1021/acs.jnatprod.1c00585

Reference yield:

syringic aldehyde (134-96-3) → sinapyl aldehyde 4-O-β-D-glucopyranoside (154461-65-1)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 20 °C

2: potassium carbonate; Tris(3,6-dioxaheptyl)amine / dichloromethane / 12 h / 20 °C

3: hydrogenchloride / water; dichloromethane / 12 h / 20 °C

4: potassium carbonate; water / tetrahydrofuran / 1 h / 65 °C

5: tetrabutylammomium bromide / chloroform; water; tetrahydrofuran / 2 h / 65 °C

6: sodium hydroxide; water / ethanol / 4 h / 20 °C

With pyridine; hydrogenchloride; Tris(3,6-dioxaheptyl)amine; tetrabutylammomium bromide; water; potassium carbonate; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water;

DOI:10.1021/acs.jnatprod.1c00585

Reference yield:

4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3) → sinapyl aldehyde 4-O-β-D-glucopyranoside (154461-65-1)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate; Tris(3,6-dioxaheptyl)amine / dichloromethane / 12 h / 20 °C

2: hydrogenchloride / water; dichloromethane / 12 h / 20 °C

3: potassium carbonate; water / tetrahydrofuran / 1 h / 65 °C

4: tetrabutylammomium bromide / chloroform; water; tetrahydrofuran / 2 h / 65 °C

5: sodium hydroxide; water / ethanol / 4 h / 20 °C

With hydrogenchloride; Tris(3,6-dioxaheptyl)amine; tetrabutylammomium bromide; water; potassium carbonate; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water;

DOI:10.1021/acs.jnatprod.1c00585

upstream raw materials:

(E)-sinapinaldehyde

uridine-5'-diphosphoglucose

syringic aldehyde

4-acetoxy-3,5-dimethoxybenzaldehyde

Refernces

• 1、 Steeves, Valerie,Foerster, Hartmut,Pommer, Ulrich,Savidge, Rodney. "Coniferyl alcohol metabolism in conifers - I. Glucosidic turnover of cinnamyl aldehydes by UDPG: Coniferyl alcohol glucosyltransferase from pine cambium". . p. 1085 - 1093. Retrieved 2007/10/03.