Structure via PubChem · Public domain (PubChem)
verbascoside
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Verbascoside is a polyphenol glycoside in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.
Chemical data
- Formula
- C29H36O15
- Molecular weight
- 624.6 g/mol
- IUPAC name
- [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-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
- 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]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
- InChIKey
- FBSKJMQYURKNSU-ZLSOWSIRSA-N
- XLogP
- -0.5
- Polar surface area
- 245 Ų
- H-bond donors
- 9
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Research
1,606 papers- Verbascoside-Rich Plant Extracts in Animal Nutrition.Antioxidants (Basel, Switzerland) · 2023
- Verbascoside: A neuroprotective phenylethanoid glycosides with anti-depressive properties.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2023
- The Neuroprotection of Verbascoside in Alzheimer's Disease Mediated through Mitigation of Neuroinflammation via Blocking NF-κB-p65 Signaling.Nutrients · 2022
- Verbascoside: comprehensive review of a phenylethanoid macromolecule and its journey from nature to bench.Inflammopharmacology · 2024
- Co-decoction of Lilii bulbus and Radix Rehmannia Recens and its key bioactive ingredient verbascoside inhibit neuroinflammation and intestinal permeability associated with chronic stress-induced depression via the gut microbiota-brain axis.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
via PubMed
Wikidata facts
- Has part
- glucose
- Mass
- 624.205420452
Show 5 more facts
- 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]2OC(=O)/C=C/c3ccc(c(c3)O)O)CO)OCCc4ccc(c(c4)O)O)O)O)O)O
- chemical formula
- C₂₉H₃₆O₁₅
- subject has role
- immunosuppressive drug
- canonical SMILES
- O=C(OC1C(OC(OCCC2=CC=C(O)C(O)=C2)C(O)C1OC3OC(C)C(O)C(O)C3O)CO)C=CC4=CC=C(O)C(O)=C4
- alternative name
- actéoside
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Occurrences
- Natural occurrences
- Derivatives
- In ''in vitro'' cultures
- Biological activity
- See also
- References
{{chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 406122558 |Name = Verbascoside |ImageFile = Acteoside.svg |ImageName = Chemical structure of verbascoside |ImageAlt = Chemical structure of verbascoside |IUPACName = 2-(3,4-Dihydroxyphenyl)ethyl α--rhamnopyranosyl-(1→4)-{5-O-[(2E)-3-(3,4-dihydroxymethyl)prop-2-enoyl]-β--glucopyranoside} |SystematicName = (2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxymethyl)prop-2-enoate |OtherNames = ActeosideKusagininOrobanchin |Section1= |Section2= }}
Verbascoside is a polyphenol glycoside in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.
Excerpted from Wikipedia’s “verbascoside” article, available under the CC BY-SA 4.0 licence.