[5-(hexopyranosyloxy)-1-oxo-2a,4a,5,7b-tetrahydro-1H-2,6-dioxacyclopenta[cd]inden-4-yl]methyl acetate

Base Information

• Chemical Name: [5-(hexopyranosyloxy)-1-oxo-2a,4a,5,7b-tetrahydro-1H-2,6-dioxacyclopenta[cd]inden-4-yl]methyl acetate
• CAS No.: 14259-45-1
• Molecular Formula: C18H22 O11
• Molecular Weight: 414.366
• European Community (EC) Number: 238-137-5
• NSC Number: 258322,31760
• DSSTox Substance ID: DTXSID10871960
• Metabolomics Workbench ID: 125835
• ChEMBL ID: CHEMBL1965021
• Mol file: 14259-45-1.mol

Synonyms:asperuloside

Chemical Property of [5-(hexopyranosyloxy)-1-oxo-2a,4a,5,7b-tetrahydro-1H-2,6-dioxacyclopenta[cd]inden-4-yl]methyl acetate

Chemical Property:

• Melting Point: 131-132°
• Boiling Point: 704.2°Cat760mmHg
• PKA: 12.76±0.70(Predicted)
• Flash Point: 254.1°C
• PSA: 161.21000
• Density: 1.62g/cm³
• LogP: -2.29600
• Storage Temp.: ?20°C
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 414.11621151
• Heavy Atom Count: 29
• Complexity: 746

Purity/Quality:

95%-98% ^*data from raw suppliers

Asperuloside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=CC2C3C1C(OC=C3C(=O)O2)OC4C(C(C(C(O4)CO)O)O)O
• Description: Asperuloside is an iridoid glycoside that has been found in G. tunetanum and has diverse biological activities, including anti-angiogenic, anti-inflammatory, and anti-obesity properties. It reduces microvessel formation by 67% in a chick embryo chorioallantoic membrane assay when used at a concentration of 2 μg/egg. Asperuloside (20, 40, and 80 mg/L) inhibits LPS-induced increases in TNF-α, IL-1β, and IL-6 production in RAW 264.7 macrophages in a concentration-dependent manner. It reduces lung myeloperoxidase (MPO) activity and bronchoalveolar lavage fluid (BALF) levels of TNF-α, IL-1β, and IL-6 in a mouse model of LPS-induced acute lung injury when administered at doses of 20, 40, and 80 mg/kg. Dietary administration of asperuloside decreases body weight gain, white adipose tissue (WAT) weight, and the ratio of WAT weight to body weight in a high-fat diet-induced mouse model of metabolic syndrome.
• Uses: Asperuloside is an iridoid found in Paederia foetida and is an inhibitor of xanthine oxidase and is used in the treatment of various disorders including inflammatory and cardiovascular diseases.