Eriocitrin
Basic information
- CAS
13463-28-0- Standard SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)c(O)c3)CC4=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O- InChIKey
OMQADRGFMLGFJF-MNPJBKLOSA-N- Molecular formula
- C27H32O15
- Average molar mass
- 596.5 g/mol
- Monoisotopic mass
- 596.17412031
Overview
Eriocitrin is a disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant. It is a member of 4'-hydroxyflavanones, a rutinoside, a trihydroxyflavanone, a member of 3'-hydroxyflavanones, a disaccharide derivative and a flavanone glycoside. It is functionally related to an eriodictyol.
Names & identifiers
- Preferred name
- Eriocitrin
- IUPAC
- (2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(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]oxy-2,3-dihydrochromen-4-one
- English name
- ERIOCITRIN
- Molecular formula
- C27H32O15
- Molecular weight
- 596.54
Names & synonyms
Eriocitrin13463-28-0EriodictiosideEriodictyol-7-O-rutinosideEriodictyol 7-O-rutinosideAS293HR5XQEriodictyol 7-O-beta-rutinosideCHEBI:28709DTXSID60864408(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(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]oxy-2,3-dihydrochromen-4-one(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-((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)oxy-2,3-dihydrochromen-4-one
Show more names
C09732EriosideERIOCITRIN(SH)AkErio? EriocitrinERIOCITRIN WITH HPLCEriodictyol glycosideEriocitrin (6CI, 7CI)Eriocitrin (Standard)
RefChem:137630DTXCID7015269154H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-, (2S)-236-668-7Eriocitrin (Mixture of Diastereomers)(S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one(S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-4H-benzopyran-4-one
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 245 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 6
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 924
Physicochemical properties
- Melting point
- 161 · 161-190°C
- Boiling point
- 956.9 · 956.9±65.0 °C(Predicted)
- Density
- 1.77 · 1.77
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- DMSO (Slightly), Methanol
- pka
- 7.15 · 7.15±0.40(Predicted)
- form
- Solid
- color
- Dark Beige to Very Dark Beige
- BRN
- 1304401 · 1304401
- InChIKey
- OMQADRGFMLGFJF-BRZCIWNANA-N
- SMILES
- C12=C(O)C=C(O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO[C@@H]4O[C@H]([C@H](O)[C@@H](O)[C@H]4O)C)O3)O)C=C1OC(C1=CC=C(O)C(O)=C1)CC2=O |&1:6,7,9,10,12,15,17,18,20,22,r|
- LogP
- 1.47 · 1.470 (est)
- CAS DataBase Reference
- 13463 · 13463-28-0(CAS DataBase Reference)
- FDA UNII
- 293 HR5XQ · AS293HR5XQ
- 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.
Safety data
- F
- 10-21
- wgk
- 3
- hs_code
- 29389090
- safety_code
- 22-24/25
- Storage Class
- 13 - Non Combustible Solids
Chemistry & industry
Applications
DescriptionEriocitrin is a flavonoid originally isolated from lemon peel that has antioxidant and enzyme inhibitory activity. Eriocitrin inhibits lipid peroxidation in a cell-free assay when used at a concentration of 10 μM and enhances the effect of α-tocopherol on lipid peroxidation. It also decreases thiobarbituric acid reactive substances (TBARS) in rat plasma when administered at a dose of 75 μmol/kg, indicating a reduction in lipid peroxidation. Eriocitrin prevents acute exercise-induced increases in TBARS, Nε-(hexanoyl)lysine (HEL), o,o-dityrosine (DT), and nitrotyrosine (NT; ) in rat liver when administered at a dose of 600 mg/kg prior to exercise. It is also an inhibitor of monoamine oxidase A (MAO-A) and MAO-B (IC50s = 86.5 and 164 μM, respectively, for human recombinant receptors).
UsesEriocitrin is one of the main flavonoids in citrus limon byproduct dried powder (CBP) that exhibits antioxidant activity.
Additional notes
DefinitionChEBI: A disaccharide derivative that consists of eriodictyol substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage
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