[(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Base Information

• Chemical Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS No.: 61276-17-3
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.596
• Hs Code.: 29389090
• European Community (EC) Number: 612-110-1
• Nikkaji Number: J389.933K
• Wikipedia: Verbascoside
• Mol file: 61276-17-3.mol

Synonyms:61276-17-3;[(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate;Acteoside;Kusaginin;TJC160;(Z)-Acetoside

Chemical Property of [(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 232℃
• Refractive Index: 1.689
• Boiling Point: 908.8 °C at 760 mmHg
• PKA: 9.31±0.10(Predicted)
• Flash Point: 294.7 °C
• PSA: 245.29000
• Density: 1.6 g/cm³
• LogP: -1.01590
• Storage Temp.: room temp
• Solubility.: DMSO (Slightly), Ethyl Acetate (Very Slightly), Methanol (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 11
• Exact Mass: 624.20542044
• Heavy Atom Count: 44
• Complexity: 936

Purity/Quality:

40%, ^*data from raw suppliers

Verbascoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C\C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• Description: Verbascoside is isolated from Lantana camara, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity.
• Uses: Verbascoside is an agent producing effects on anti-GBM nephritis in rats. Effective agent against glomerulonephritis. Phenolic anti-oxidant agent.

Technology Process of [(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

There total 21 articles about [(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate 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: 87.0%

2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2,3,4-tris-O-triethylsilyl-α-L-rhamnopyranosyl(1→3)-2,6-di-O-triethylsilyl-4-O-(E)-3,4-bis(tert-butyldimethylsilyl)-caffeoyl-β-D-glucopyranoside → Acteoside (61276-17-3,97747-56-3,138604-99-6,145306-71-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.1c03528

Reference yield: 44.0%

3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside (253790-76-0) → Acteoside (61276-17-3,97747-56-3,138604-99-6,145306-71-4)

Guidance literature:

With cyclohexa-1,4-diene; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; at 40 ℃; for 10h;

DOI:10.1021/jo9906983

Reference yield: 35.0%

Arenarioside (94130-58-2) → Acteoside (61276-17-3,97747-56-3,138604-99-6,145306-71-4)

Guidance literature:

With sulfuric acid; In ethanol; for 1h; Heating;

DOI:10.3987/COM-89-S36

upstream raw materials:

Arenarioside

Lavandulifolioside

2-(3,4-dihydroxyphenyl)ethyl-O-β-D-galactopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-(4-O-trans-caffeoyl)-β-D-glucopyranoside

3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

Downstream raw materials:

per-O-acetyl-verbascoside

hydroxytyrosol

Methyl caffeate

cis-verbascoside

Refernces

• 1、 Kyriakopoulou,Magiatis,Skaltsounis,Aligiannis,Harvala. "Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia". . p. 1095 - 1097. Retrieved 2007/10/03.
• 2、 Kawada, Toshinari,Asano, Ryuji,Hayashida, Shiho,Sakuno, Tomoyasu. "Total Synthesis of the Phenylpropanoid Glycoside, Acteoside". . p. 9268 - 9271. Retrieved 2007/10/03.