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13463-28-0

13463-28-0 Structure

13463-28-0 Structure
IdentificationMore
[Name]

ERIOCITRIN
[CAS]

13463-28-0
[Synonyms]

ERIOCITRIN
ERIODICTYL-7-RUTINOSIDE
ERIODICTYOL-7-O-RUTINOSIDE
ERIODICTYOL-7-RUTINOSIDE
(S)-3',4',5,7-TETRAHYDROXYFLAVANONE-7-[6-O-(ALPHA-L-RHAMNOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE]
(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
ERIOCITRIN(SH)
ERIOCITRIN WITH HPLC
(S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2α-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one
(S)-3',4',5,7-Tetrahydroxyflavanone-7-[6-O-(alpha-L-hamnopyranosyl)-beta-D-glucopyranoside]
[EINECS(EC#)]

236-668-7
[Molecular Formula]

C27H32O15
[MDL Number]

MFCD00017472
[Molecular Weight]

596.53
[MOL File]

13463-28-0.mol
Chemical PropertiesBack Directory
[Melting point ]

161-190°C
[Boiling point ]

956.9±65.0 °C(Predicted)
[density ]

1.77
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

DMSO (Slightly), Methanol
[form ]

neat
[pka]

7.15±0.40(Predicted)
[color ]

Dark Beige to Very Dark Beige
[BRN ]

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]

1.470 (est)
[CAS DataBase Reference]

13463-28-0(CAS DataBase Reference)
Safety DataBack Directory
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

3
[F ]

10-21
[HS Code ]

29389090
Hazard InformationBack Directory
[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).
[Chemical Properties]

solid
[Uses]

Eriocitrin is one of the main flavonoids in citrus limon byproduct dried powder (CBP) that exhibits antioxidant activity.
[Definition]

ChEBI: 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
[target]

LDL | ATP synthase
[storage]

4°C, protect from light
[References]

[1] ROBERT M. HOROWITZ  Bruno G. Flavonoid Compounds of Citrus. III. Isolation and Structure of Eriodictyol Glycoside[J]. Journal of the American Chemical Society, 1960, 82 11: 2803-2806. DOI: 10.1021/ja01496a033
[2] Y. MIYAKE T O Kanefumi Yamamoto. Isolation of eriocitrin (eriodictyol 7-rutinoside) from lemon fruit (Citrus limon Burm. f.) and its antioxidative activity[J]. Food Science and Technology International, Tokyo, 1997, 1 1: 84-89. DOI: 10.3136/fsti9596t9798.3.84
[3] YOSHIAKI MIYAKE. Identification and Antioxidant Activity of Flavonoid Metabolites in Plasma and Urine of Eriocitrin-Treated Rats[J]. Journal of Agricultural and Food Chemistry, 2000, 48 8: 3217-3224. DOI: 10.1021/jf990994g
[4] KEN-ICHIRO MINATO . Lemon flavonoid, eriocitrin, suppresses exercise-induced oxidative damage in rat liver[J]. Life sciences, 2003, 72 14: Pages 1609-1616. DOI: 10.1016/s0024-3205(02)02443-8
[5] SIMONE CARRADORI*. Inhibition of Human Monoamine Oxidase: Biological and Molecular Modeling Studies on Selected Natural Flavonoids[J]. Journal of Agricultural and Food Chemistry, 2016, 64 47: 9004-9011. DOI: 10.1021/acs.jafc.6b03529
Spectrum DetailBack Directory
[Spectrum Detail]

ERIOCITRIN(13463-28-0)MS
ERIOCITRIN(13463-28-0)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

13463-28-0(sigmaaldrich)
13463-28-0 suppliers list
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