[(4S)-2-Oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-6-yl]methyl acetate
Basic information
- CAS
14259-45-1- Standard SMILES
CC(=O)OCC1=C[C@@H]2OC(=O)C3=COC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C1C32- InChIKey
IBIPGYWNOBGEMH-AEFNDFPBSA-N- Molecular formula
- C18H22O11
- Average molar mass
- 414.4 g/mol
- Monoisotopic mass
- 414.11621151
Names & identifiers
- Preferred name
- [(4S)-2-Oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-6-yl]methyl acetate
- IUPAC
- [(4S)-2-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-6-yl]methyl acetate
- English name
- ASPERULOSIDE
- Molecular formula
- C18H22O11
- Molecular weight
- 414.36
Names & synonyms
SCHEMBL308265[(4S)-2-Oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-6-yl]methyl acetate[(2aS)-5-(beta-D-Glucopyranosyloxy)-1-oxo-2a,4a,5,7b-tetrahydro-1H-2,6-dioxacyclopenta[cd]inden-4-yl]methyl acetateNsc 31760AsperulosidASPERULOSIDEAsperuloside-RMEinecs 238-137-5RUBICHLORIC ACIDAsperuloside (Standard)Asperuloside >=95% (LC/MS-ELSD)(2aS)-2a,4aα,5,7bα-Tetrahydro-4-acetoxymethyl-5α-(β-D-glucopyranosyloxy)-1H-2,6-dioxacyclopent[cd]inden-1-one
Show more names
[2aS-(2aα,4aα,5α,7bα)]-5-(β-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-1-oxo-1H-2,6-dioxacyclopent[cd]inden-4-ylmethyl acetate
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 161 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 746
Physicochemical properties
- Melting point
- 131 · 131-132°
- alpha
- 25 · D25 -198.6° (c = 1.44 in water)
- Boiling point
- 704.2 · 704.2±60.0 °C(Predicted)
- Density
- 1.62 · 1.62±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in methanol and water
- form
- powder
- pka
- 12.76 · 12.76±0.70(Predicted)
- color
- White
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- IBIPGYWNOBGEMH-BWDLRQFSNA-N
- SMILES
- [C@]12([H])C(COC(=O)C)=C[C@]3([H])OC(=O)C(=COC1O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)[C@]23[H] |&1:0,9,19,20,22,23,25,30,r|
- FDA UNII
- 3 CFI02X39 · V3CFI02X39
- EPA Substance Registry System
- 1 H-2,6-Dioxacyclopent[cd]inden-1-one, · 1H-2,6-Dioxacyclopent[cd]inden-1-one, 4-[(acetyloxy)methyl]-5-(?-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-, (2aS,4aS,5S,7bS)- (14259-45-1)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312+P330-P501
Chemistry & industry
Applications
DescriptionAsperuloside 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.
UsesAsperuloside 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.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A iridoid monoterpenoid glycoside isolated from Galium verum.
Related reactions
0 records
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Compound notes
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