Echinacoside
Basic information
- CAS
82854-37-3- Standard SMILES
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2OC(=O)/C=C/c2ccc(O)c(O)c2)[C@H](O)[C@H](O)[C@H]1O- InChIKey
FSBUXLDOLNLABB-ISAKITKMSA-N- Molecular formula
- C35H46O20
- Average molar mass
- 786.7 g/mol
- Monoisotopic mass
- 786.25824385
Overview
Echinacoside is an oligosaccharide.
Names & identifiers
- Preferred name
- Echinacoside
- IUPAC
- [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
- English name
- ECHINACOSIDE
- Molecular formula
- C35H46O20
- Molecular weight
- 786.73
Names & synonyms
Echinacoside82854-37-3DTXSID0033469I04O1DT48TDTXCID8013469[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate((2R,3R,4R,5R,6R)-6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxymethyl)-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-3-yl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoateRefChem:590551beta-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-alpha-L-mannopyranosyl-(1->3)-O-(beta-D-glucopyranosyl-(1->6))-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate)MFCD00075695[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 324 Ų
- Hydrogen bond donors
- 12
- Hydrogen bond acceptors
- 20
- Rotatable bonds
- 14
- Heavy atoms
- 55
- Formal charge
- 0
- Complexity
- 1,230
Physicochemical properties
- Boiling point
- 1062.7 · 1062.7±65.0 °C(Predicted)
- Density
- 1.66 · 1.66±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 60 · DMSO:60.0(Max Conc. mg/mL);76.26(Max Conc. mM)DMSO:PBS (pH 7.2) (1:9):0.1(Max Conc. mg/mL);0.13(Max Conc. mM)DMF:30.0(Max Conc. mg/mL);38.13(Max Conc. mM)Ethanol:52.5(Max Conc. mg/mL);66.73(Max Conc. mM)Water:24.36(Max Conc. mg/mL);30.96(Max Conc. mM)
- form
- powder
- pka
- 8.43 · 8.43±0.20(Predicted)
- color
- White-beige
- BRN
- 4778612 · 4778612
- Stability
- Hygroscopic
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- FSBUXLDOLNLABB-ISAKITKMSA-N
- LogP
- 0.14 · 0.140 (est)
- FDA UNII
- 4 O1DT48T · I04O1DT48T
- UNSPSC Code
- 85151701 · 85151701
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- rtecs
- LZ5786500
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of ActionThe neuroprotective effects are thought to be mediated via effects on mitogen-activated protein kinase, nuclear factor kappa-B, caspases 3 and 8, as well as CHOP pathways.
Metabolism/Metabolites
The metabolism of echinacoside has been investigated in rats and is thought to involve catechol O-methyltransferase as well as unspecified UDP-gluc- uronosyltransferases and sulfotransferases. A study of echinacoside's metabolism by human intestinal flora identified 13 metabolites which are produced independantly of human metabolism.
Absorption, Distribution and ExcretionAnimal studies suggest an oral bioavailability of 0.83%.
Applications
DescriptionEchinacoside is a phenylethanoid glycoside that has been found in Echinacea and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals (EC50 = 6.6 μM in a cell-free assay). Echinacoside (10 μg/ml) inhibits hydrogen peroxide-induced production of reactive oxygen species (ROS) and apoptosis in PC12 cells. It reduces increases in plasma alanine aminotransferase (ALT), TNF-α, IL-1β, IL-16, and IL-10 levels and hepatocyte apoptosis induced by LPS/D-galactosamine in a mouse model of acute liver injury when administered at a dose of 60 mg/kg. Echinacoside (20 mg/kg per day for 15 days) prevents loss of dopaminergic neurons in the substantia nigra pars compacta and decreases in striatal dopamine and 3,4-dihydroxyphenylacetic acid (DOPAC) levels in a mouse model of MPTP-induced Parkinson''s disease. It also improves motor performance in the rotarod test in the same model.
UsesEchinacoside Ethanolate is a caffeic acid glycoside, known for its neuroprotective, antiinflammatory and anti-oxidative activities. Also an anti[proliferative towards hypoxia influenced pulmonary artery smooth muscle cells.
Additional notes
ChEBI: Echinacoside is an oligosaccharide.
Related reactions
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Compound notes
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