Resveratroloside

Base Information

• Chemical Name: Resveratroloside
• CAS No.: 38963-95-0
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.39
• Hs Code.: 2938909090
• UNII: 7DBS6RKM2S
• DSSTox Substance ID: DTXSID60415792
• Nikkaji Number: J1.270.496H,J958.577J,J752.926K
• Wikipedia: Resveratroloside
• Wikidata: Q17089265
• Metabolomics Workbench ID: 137785
• ChEMBL ID: CHEMBL478753
• Mol file: 38963-95-0.mol

Synonyms:3,5,4'-trihydroxystilbene-4'-O-beta-D-glucoside;3,5,4'-trihydroxystilbene-4'-O-glucoside;E.resveratroloside;resveratroloside

Chemical Property of Resveratroloside

Chemical Property:

• Melting Point: 235-238 °C
• Boiling Point: 700.3±60.0 °C(Predicted)
• PKA: 9.19±0.10(Predicted)
• PSA: 156.91000
• Density: 1.521±0.06 g/cm3(Predicted)
• LogP: 0.53920
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 390.13146766
• Heavy Atom Count: 28
• Complexity: 496

Purity/Quality:

≥98% ^*data from raw suppliers

Resveratroloside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Uses: Resveratroloside is a compound that shows cancer-chemopreventive and antioxidative activity through study. It is due to being a derivative of Resveratrol (R150000) which is a minor constituent of wine , correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been s hown to inhibit events associated with tumor initiation, promotion and progression. Resveratroloside is a compound that shows cancer-chemopreventive and antioxidative activity through study. It is due to being a derivative of Resveratrol (R150000) which is a minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion and progression.

Technology Process of Resveratroloside

There total 16 articles about Resveratroloside 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: 97.0%

(E)-1-(3,5-diacetoxy)-2-(4'-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)ethene (38968-01-3) → trans-resveratroloside (38963-95-0,50450-48-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1081/SCC-120030744

Reference yield: 95.0%

(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene (892402-78-7) → trans-resveratroloside (38963-95-0,50450-48-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 25 ℃; for 5h;

DOI:10.1055/s-2006-926394

Reference yield: 37.0%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) → trans-resveratroloside (38963-95-0,50450-48-1) + (E)-5,4'-dihydroxystilbene 3-O-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside (1065022-43-6) + trans-Resveratrol 3-O-(6-O-β-L-arabinopyranosyl)-β-D-glucopyranoside + polydatin (27208-80-6,65914-17-2,148766-36-3)

Guidance literature:

With catharanthus roseus; In methanol; at 25 ℃; for 120h; Microbiological reaction;

DOI:10.1271/bbb.120126

upstream raw materials:

resveratrol-4′-O-β-D-(2′′-O-galloyl)glucopyranoside

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

(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene

L-arabinose

Downstream raw materials:

trans-3,5-bis(triphenylmethyloxy)stilbene-4'-O-β-D-glucopyranoside

C₇₇H₆₄O₈

trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside

Refernces

• 1、 Uesugi, Daisuke,Hamada, Hiroki,Shimoda, Kei,Kubota, Naoji,Ozaki, Shin-Ichi,Nagatani, Naoki. "Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene". . p. 226 - 230. Retrieved 2017/01/24.
• 2、 Xie, Kebo,Ridao, Chen,Li, Jianhua,Wang, Ruishan,Chen, Dawei,Dou, Xiaoxiang,Dai, Jungui. "Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius". supporting information. p. 4874 - 4877. Retrieved 2015/04/27.