3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside

Base Information

• Chemical Name: 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside
• CAS No.: 113349-27-2
• Molecular Formula: C16H22 O8
• Molecular Weight: 342.346
• Mol file: 113349-27-2.mol

Synonyms:b-D-Glucopyranoside,(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenyl (9CI); b-D-Glucopyranoside,3-(4-hydroxy-3-methoxyphenyl)-2-propenyl, (E)-; (E)-Isoconiferin; Citrusin D;trans-Isoconiferin

Chemical Property of 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside

Chemical Property:

• Boiling Point: 606.9±55.0 °C(Predicted)
• PKA: 10.02±0.31(Predicted)
• PSA: 128.84000
• Density: 1.44±0.1 g/cm3(Predicted)
• LogP: -0.76950

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Citrusin D is isolated from Citrus unshiu and may have potential as an antihypertensive agent.

Technology Process of 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside

There total 17 articles about 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside 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: 99.0%

4-hydroxy-3-methoxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (869728-94-9) → 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside (113349-27-2)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1016/j.tet.2005.08.043

Reference yield: 90.0%

C22H32O12 → 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside (113349-27-2)

Guidance literature:

With α-L-rhamnosidasefrom aspergillus terreus; In aq. phosphate buffer; at 35 ℃; for 3h; pH=5; Enzymatic reaction;

DOI:10.1002/cssc.201700136

Reference yield: 88.0%

4-acetoxy-3-methoxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside → 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside (113349-27-2)

Guidance literature:

With sodium methylate; In methanol; at 4 ℃;

DOI:10.3762/bjoc.12.51

upstream raw materials:

4-hydroxy-3-methoxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-(4-bromo-2-methoxyphenoxy)tetrahydropyran

allyl β-D-glucopyranoside

D-glucose

Downstream raw materials:

(2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate

coniferal alcohol

Refernces

• 1、 Mastihubová, Mária,Poláková, Monika. "A selective and mild glycosylation method of natural phenolic alcohols". . p. 524 - 530. Retrieved 2016/04/08.
• 2、 Matsushita, Yoh-Ichi,Sugamoto, Kazuhiro,Kita, Yoshio,Matsui, Takanao. "Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose". . p. 8709 - 8712. Retrieved 2007/10/03.