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Merck

SMB00321

Sigma-Aldrich

Narirutin

≥98% (HPLC)

Sinónimos:

Narirutin, (2S)-7-((6-O-(6-Deoxy-a-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, Isonaringenin, Isonaringin, Naringenin rutinoside

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About This Item

Fórmula empírica (notación de Hill):
C27H32O14
Número de CAS:
Peso molecular:
580.53
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98% (HPLC)

form

powder

mp

180 °C

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

OC1=CC=C([C@@H]2CC(C(C(O)=CC(O[C@@H]3O[C@H](CO[C@H]4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)[C@@H](O)[C@H](O)[C@H]3O)=C5)=C5O2)=O)C=C1

InChI

1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

InChI key

HXTFHSYLYXVTHC-AJHDJQPGSA-N

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General description

Narirutin is a flavanone that constitutes the major flavonoids found in citrus fruits like oranges, grapefruits, and tangerines. It is a multi-potent phytochemical.

Application

Narirutin has been used as a flavonoid supplement to study its effect on the prevention of depression-like behavior and modulatory effect on the inflammatory profile in rat female offspring.

Biochem/physiol Actions

Narirutin is known to possess anti-allergic, anti-inflammatory, antioxidant, and anti-proliferative properties. It inhibits allergic eosinophilic airway inflammation in the mouse model. Narirutin also inhibits lipopolysaccharide (LPS)-induced inflammatory response by inhibiting nuclear factor-κB (NF-κB) and mitogen-activated protein kinases (MAPKs). It displays antioxidant and protective effects on attenuating alcohol-induced liver damage while co-consumed with alcohol in mice model, and can be useful in Alzheimer′s disease (AD) therapeutics.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Clinical and experimental pharmacology & physiology, 34(8), 766-770 (2007-06-30)
1. Flavonoids are naturally occurring compounds that possess anti-allergic, anti-inflammatory, antiproliferative and anti-oxidant properties. In the present study, we investigated whether the flavonoid narirutin could reduce airway inflammation in ovalbumin (OVA)-sensitized/challenged NC/Nga mice, a model of allergic eosinophilic airway inflammation.
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Fructus Aurantii (FA) derived from the dried, and unripe fruit of This experiment was designed to illustrate the material basis of FAF promoting gastrointestinal motility and explore the mechanism of action from an organic and inorganic combination point of view.

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