Eriocitrin - ALL Chemistry-Professional and Leading Custom Chemical Supplier

Eriocitrin

IUPAC Name
(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

Synonyms
(S)-3',4',5,7-TETRAHYDROXYFLAVANONE-7-[6-O-(ALPHA-L-RHAMNOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE]; ERIOCITRIN; ERIODICTYL-7-RUTINOSIDE; ERIODICTYOL-7-O-RUTINOSIDE; ERIODICTYOL-7-RUTINOSIDE; (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; (s)-3',4',5,7-tetrahydroxyflavanone-7-[6-o-(α-l-rhamnopyranosyl)-β-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-methyl-oxan-2-yl]oxymethyl]oxan-2-yl]oxy-chroman-4-one

Description
Eriocitrin 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 (Item No. 25985) 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; Item No. 89540) 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).

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=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O

InChI
InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

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