TRANS-ASTRINGIN

Base Information

• Chemical Name: TRANS-ASTRINGIN
• CAS No.: 29884-49-9
• Molecular Formula: C20H22 O9
• Molecular Weight: 406.389
• Mol file: 29884-49-9.mol

Synonyms:Astringin(8CI); b-D-Glucopyranoside,3-[2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenyl, (E)-; (E)-Astringin;3,4,3',5'-Tetrahydroxystilbene 3'-glucoside; trans-Astringin

Chemical Property of TRANS-ASTRINGIN

Chemical Property:

• Vapor Pressure: 5.06E-24mmHg at 25°C
• Melting Point: 218-220℃
• Boiling Point: 756.1°Cat760mmHg
• PKA: 9.16±0.10(Predicted)
• Flash Point: 411.1°C
• PSA: 160.07000
• Density: 1.593g/cm³
• LogP: 0.15250

Purity/Quality:

≥98% ^*data from raw suppliers

Astringin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TRANS-ASTRINGIN

There total 3 articles about TRANS-ASTRINGIN 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: 86.0%

5-acetoxy-3-(tetra-O-acetyl-β-D-glucopyranosyl)oxy-3′,4′-dihydroxystilbene → (E)-astringin (29884-49-9)

Guidance literature:

With sodium dithionite; sodium hydroxide; In methanol; water; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1080/09168451.2017.1303362

Reference yield:

polydatin (27208-80-6,65914-17-2,148766-36-3) → (E)-astringin (29884-49-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap / pyridine

2.1: Burkholderia cepacia lipase immobilized on diatomaceous earth / tetrahydrofuran; isopropyl alcohol

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / N,N-dimethyl-formamide / 19 h / -15 °C / Inert atmosphere

3.2: -15 °C / Inert atmosphere

4.1: sodium dithionite; sodium hydroxide / methanol; water / 12 h / 20 °C / Inert atmosphere

With dmap; sodium dithionite; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1080/09168451.2017.1303362

Reference yield:

(E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene (62502-04-9) → (E)-astringin (29884-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Burkholderia cepacia lipase immobilized on diatomaceous earth / tetrahydrofuran; isopropyl alcohol

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / N,N-dimethyl-formamide / 19 h / -15 °C / Inert atmosphere

2.2: -15 °C / Inert atmosphere

3.1: sodium dithionite; sodium hydroxide / methanol; water / 12 h / 20 °C / Inert atmosphere

With sodium dithionite; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1080/09168451.2017.1303362

upstream raw materials:

polydatin

(E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene

Downstream raw materials:

(E)-3,3',4'-triacetoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene

trans-piceatannol

Acetic acid (2R,3S,4R,5S,6S)-4,5-diacetoxy-2-{3-acetoxy-5-[(E)-2-(3,4-diacetoxy-phenyl)-vinyl]-phenoxy}-6-acetoxymethyl-tetrahydro-pyran-3-yl ester

3'-β-D-Glucopyranosyloxy-3,4,5'-trihydroxy-1,2-diphenylethane

Refernces