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rutin

Structure via PubChem · Public domain (PubChem)

EntityQ407857· pop 31· linked from 197 articles

Also known as 3-Rhamnoglucosylquercetin, 3-Rutinosyl quercetin, 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside, Rutinoside, quercetin 3beta-, Glucopyranoside, quercetin-3 6-O-alpha-L-rhamnopyranosyl-,beta-D, Quercetin 3-O-beta-D-rutinoside, Eldrin, Tanrutin

Rutin (rutoside, quercetin-3-O-rutinoside or sophorin) is the glycoside combining the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a flavonoid glycoside found in a wide variety of plants, including citrus.

Chemical data

Formula
C27H30O16
Molecular weight
610.5 g/mol
IUPAC name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
InChIKey
IKGXIBQEEMLURG-NVPNHPEKSA-N
XLogP
-1.3
Polar surface area
266 Ų
H-bond donors
10
H-bond acceptors
16
Formal charge
0

via PubChem

Wikidata facts

Mass
610.153
Image
Rutin by Danny S. - 001.JPG
Show 5 more facts
chemical formula
C₂₇H₃₀O₁₆
Commons category
Rutin
isomeric SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
canonical SMILES
CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
World Health Organisation international non-proprietary name
rutoside
Sources (5)

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Article

7 sections
Contents
  • Occurrences
  • Metabolism
  • In food
  • Research
  • Biosynthesis
  • References
  • External links

Rutin (rutoside, quercetin-3-O-rutinoside or sophorin) is the glycoside combining the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a flavonoid glycoside found in a wide variety of plants, including citrus.

== Occurrences == Rutin is one of the phenolic compounds found in the plant species Carpobrotus edulis. Its name comes from the name of Ruta graveolens, a plant that also contains rutin. Various citrus fruit peels contain 32 to 49 mg per g of flavonoids expressed as rutin equivalents. Citrus leaves contain rutin at concentrations of 11 mg per g in orange trees and 7 mg per g in lime trees. In 2021, Samoan researchers identified rutin in the native plant matalafi (Psychotria insularum).

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