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SMB00321

Sigma-Aldrich

Narirutin

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C27H32O14
CAS Number:
14259-46-2
Molecular Weight:
580.53
MDL number:
MFCD00017316
UNSPSC Code:
12352205
PubChem Substance ID:
329824953
NACRES:
NA.25

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Roberto Massenti et al.
Journal of the science of food and agriculture, 96(1), 73-78 (2014-12-30)
In order to evaluate the effect of citrus greening disease, or Huanglongbing (HLB), on quality components and flavonoid contents of 'Valencia' oranges, fruit from non-infected trees (control), from infected trees but symptom-less (asymptomatic) and from infected trees and showing clear
Paula de Paula Menezes Barbosa et al.
Food science and biotechnology, 27(5), 1301-1309 (2018-10-16)
Significant amounts of citrus by-products remain after juice processing, which is then used to obtain pectin. The pectin industry then generates a new waste. No study has characterized this residue or suggested applications for it. The main goal of this
Norihiko Funaguchi et al.
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.
Enzyme-assisted biotransformation increases hesperetin content in citrus juice by-products.
Amanda Roggia Ruviaro et al.
Food research international (Ottawa, Ont.), 124, 213-221 (2019-08-31)
Lara Alexander et al.
Food chemistry, 276, 626-635 (2018-11-10)
The bitter taste of Cyclopia genistoides infusions is unacceptable to consumers, who are used to the slightly sweet taste of the herbal teas produced from other Cyclopia species. Bitter taste intensities of crude phenolic fractions of a bitter hot water
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