61303-13-7

Basic information

• Product Name: Isoacteoside
• Synonyms: Isokusaginin;Isoacteoside, >=98%;β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-, 6-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate];ISOVERBASCOSIDE;ISOACTEOSIDE;Isoacteosid;[(2R,3R,4S,5R,6R)-5-(3,4-Dihydroxyphenyl)-6-ethoxy-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate;2-(3,4-Dihydroxyphenyl)ethyl 3-O-(α-L-rhamnopyranosyl)-6-O-[(E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-β-D-glucopyranoside
• CAS NO: 61303-13-7
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.59
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 61303-13-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 220～230℃
• Boiling Point: 940.2 °C at 760 mmHg
• Flash Point: 305.2 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.32±0.10(Predicted)
• CAS DataBase Reference: Isoacteoside(CAS DataBase Reference)
• NIST Chemistry Reference: Isoacteoside(61303-13-7)
• EPA Substance Registry System: Isoacteoside(61303-13-7)

Safety Data

• Hazardous Substances Data: 61303-13-7(Hazardous Substances Data)

Usage

Description

Isoacteoside is a phenylethanoid glycoside with diverse biological activities, including antioxidant, anti-inflammatory, and antitumor properties. It has been found in C. trichotomum and exhibits potential health benefits due to its ability to scavenge free radicals, inhibit lipid peroxidation, and induce apoptosis in cancer cells.
Used in Food Industry:
Isoacteoside is used as a food antioxidant for its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and inhibit hydrogen peroxide-induced lipid peroxidation in V79-4 cells. This makes it a promising candidate for preserving the quality and extending the shelf life of various food products.
Used in Pharmaceutical Industry:
Isoacteoside is used as an antitumor agent for its ability to induce apoptosis and production of reactive oxygen species (ROS) in OVCAR-3 cells, as well as reduce their viability. It also inhibits tumor growth in an OVCAR-3 mouse xenograft model when administered at a dose of 30 mg/kg.
Used in Neuroprotection:
Isoacteoside is used for its neuroprotective effects, as it decreases brain amyloid deposition and increases exploratory behavior in rats when infused into the cerebral ventricles with amyloid-β (1-42) (Aβ42).
Used in Anti-inflammatory Applications:
Isoacteoside is used as an anti-inflammatory agent, as it decreases xylene-induced ear edema in mice, demonstrating its potential in reducing inflammation and associated symptoms.
Used in Critical Care Medicine:
Isoacteoside is used to increase survival in a mouse model of LPS-induced endotoxic shock, highlighting its potential role in critical care medicine for the treatment of severe inflammatory conditions.

InChI:InChI=1/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1

Upstream product

• 61276-17-3 Acteoside 

Downstream Products

• 2280-44-6 D-Glucose 
• 73-34-7 L-rhamnose 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 61548-34-3 decaffeoyl verbascoside 
• 83529-65-1 isoacteoside peracetate 

Relevant articles and documents

Antioxidative activities of phenylethanoid glycosides from Ligustrum purpurascens

Tea and kudingcha (bitter tea) are the two most popular beverages consumed in China. Tea derived from the leaves of Camellia sinensis has been well studied for its various health benefits, but there are very limited data on the biological activities of bitter tea derived from the leaves of Ligustrum purpurascens (LP). The present study was carried out to characterize the antioxidants present in the bitter tea brewed from the leaves of LP. It was found that the crude glycoside fraction possessed strong protection against oxidation of human low-density lipoprotein (LDL). The column chromatographic separation led to the isolatation of five phenylethanoid glycosides, namely, acteoside, ligupurpuroside A, cis-ligupurpuroside B, trans-ligupurpuroside B, and osmanthuside B. When acteoside was heated in the boiling water, it was isomerized to form isoacteoside. Acteoside, isoacteoside, and ligupurpuroside A purified from LP were protective, whereas cis-ligupurpuroside B, trans-ligupurpuroside B, and osmanthuside B exhibited no protection to human LDL from Cu2+-medicated oxidation. Acteoside, isoacteoside, and ligupurpuroside A were also effective in preventing the peroxyl free radical-induced oxidation of α-tocopherol in human LDL. The antioxidant activities of acteoside, isoacteoside, and ligupurpuroside A were comparable to that observed for a green tea antioxidant, (-)-epicatechin gallate. The inhibitory effect of these three phenylethanoid glycosides on oxidation of human LDL and α-tocopherol was dose-dependent at concentrations of 5-40 μM. The present results suggest that the bitter tea beverage derived from LP contains effective antioxidants that may have an equal benefit as a green tea beverage.