2-[3-hydroxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Base Information

• Chemical Name: 2-[3-hydroxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS No.: 30197-14-9
• Molecular Formula: C₂₁H₂₄O₈
• Molecular Weight: 404.417
• DSSTox Substance ID: DTXSID90422030
• ChEMBL ID: CHEMBL1863546
• Mol file: 30197-14-9.mol

Synonyms:30197-14-9;2-[3-hydroxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol;MLS002207168;CHEMBL1863546;DTXSID90422030;AKOS032949079;LS-14892;SMR001306745;3,5-DIHYDROXY-4-METHOXYSTILBENE3-O-BETA-D-GLUCOSIDE

Chemical Property of 2-[3-hydroxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property:

• Boiling Point: 700.5±60.0 °C(Predicted)
• PKA: 9.19±0.10(Predicted)
• PSA: 128.84000
• Density: 1.433±0.06 g/cm3(Predicted)
• LogP: 0.74990
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 404.14711772
• Heavy Atom Count: 29
• Complexity: 521

Purity/Quality:

98%,99%, ^*data from raw suppliers

Desoxyrhaponticin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• Uses: Deoxyrhaponticin is an impurity of Rhaponticin (R316000), a stilbene derivative found in Rheum. It is an inhibitor of Tyrosinase which is responsible for the molting process in insects, undesirable browning of fruits and vegetables, and coloring of skin, hair, and eyes in animals.

Technology Process of 2-[3-hydroxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

There total 10 articles about 2-[3-hydroxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 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:

desoxyrhaponticin 6''-O-gallate (94356-29-3) → 3,4,5-trihydroxybenzoic acid (149-91-7) + (E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene (30197-14-9,65830-63-9,94425-94-2)

Guidance literature:

With tannase; In water; for 1h; Ambient temperature;

Reference yield:

(E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene (197440-96-3) → (E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene (30197-14-9,65830-63-9,94425-94-2)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(97)00087-6

Reference yield:

3,5-dihydroxybenzaldehyde (26153-38-8) → (E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene (30197-14-9,65830-63-9,94425-94-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N,N-diisopropylethylamine / dimethylformamide / 0.5 h / 20 °C

2.1: butyllithium / hexane; tetrahydrofuran / 15 - 20 °C

2.2: 78 percent / hexane; tetrahydrofuran / 1 h / 20 °C

3.1: 68.3 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

4.1: 32 percent / benzyltriethylammonium bromide; NaOH / CHCl₃; H₂O / 10 h / 60 °C

5.1: sodium methoxide / methanol / 2 h / 20 °C

With sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium methylate; benzyltriethylammonium bromide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; chloroform; water; N,N-dimethyl-formamide; 1.1: silylation / 2.1: deprotonation / 2.2: Wittig reaction / 3.1: desilylation / 4.1: glucosylation / 5.1: Deacetylation;

DOI:10.1016/S0008-6215(97)00087-6

upstream raw materials:

desoxyrhaponticin 6''-O-gallate

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

3,5-dihydroxybenzaldehyde

5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol

Downstream raw materials:

polydatin

cis-3,5-dihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside

Refernces

• 1、 Orsini, Fulvia,Pelizzoni, Francesca,Bellini, Barbara,Miglierini, Giuliana. "Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)". . p. 95 - 109. Retrieved 2007/10/03.