Isoacteoside

Base Information

• Chemical Name: Isoacteoside
• CAS No.: 61303-13-7
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.596
• Hs Code.: 29389090
• NSC Number: 729649
• UNII: 588LJK42AP
• DSSTox Substance ID: DTXSID501317837
• Nikkaji Number: J389.934I,J2.924.642D
• Wikidata: Q27261572
• Metabolomics Workbench ID: 140127
• ChEMBL ID: CHEMBL504873
• Mol file: 61303-13-7.mol

Synonyms:isoacetoside;isoacteoside;isoverbascoside

Chemical Property of Isoacteoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 220～230℃
• Refractive Index: 1.689
• Boiling Point: 940.2 °C at 760 mmHg
• PKA: 9.32±0.10(Predicted)
• Flash Point: 305.2 °C
• PSA: 245.29000
• Density: 1.6 g/cm³
• LogP: -1.01590
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• 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:

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

Isoacteoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)C=CC4=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]2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)O
• Description: Isoverbascoside is a phenylethanoid glycoside that has been found in C. trichotomum and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay and inhibits hydrogen peroxide-induced lipid peroxidation in V79-4 cells when used at a concentration of 10 μg/ml. Isoverbascoside (7.5-30 μM) induces apoptosis and production of reactive oxygen species (ROS) in, and reduces viability of, OVCAR-3 cells. It inhibits tumor growth in an OVCAR-3 mouse xenograft model when administered at a dose of 30 mg/kg. Isoverbascoside (2.5 and 5 mg/kg) decreases brain amyloid deposition and increases exploratory behavior in rats when infused into the cerebral ventricles with amyloid-β (1-42) (Aβ42; ). It also decreases xylene-induced ear edema in mice and increases survival in a mouse model of LPS-induced endotoxic shock.
• Uses: Isoacteoside is a possible food antioxidant.

Technology Process of Isoacteoside

There total 1 articles about Isoacteoside 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: 80.0%

Acteoside (61276-17-3,97747-56-3,138604-99-6,145306-71-4) → Isoacteoside (61303-13-7,143729-70-8)

Guidance literature:

In water; at 100 ℃; for 8h;

DOI:10.1021/jf0100604

Reference yield: 67.0%

acetic anhydride (108-24-7) + Isoacteoside (61303-13-7,143729-70-8) → isoacteoside peracetate (83529-65-1)

Guidance literature:

With pyridine; for 24h; Ambient temperature;

DOI:10.1021/np9703914

Reference yield:

Isoacteoside (61303-13-7,143729-70-8) → D-Glucose (2280-44-6) + L-rhamnose (73-34-7)

Guidance literature:

With sulfuric acid; at 95 ℃; for 1h;

DOI:10.1016/j.fitote.2011.12.025

upstream raw materials:

Acteoside

Downstream raw materials:

isoacteoside peracetate

decaffeoyl verbascoside

methyl (E)-3-(3,4-dimethoxyphenyl)acrylate

D-Glucose

Refernces

• 1、 Schilling, Gerhard,Huegel, Michael,Mayer, Walter. "Verbascoside and Isoverbascoside from Paulownia Tomentosa Steud". . p. 1633 - 1635. Retrieved 2007/10/02.