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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
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)
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
Bing Zhang et al.
Molecules (Basel, Switzerland), 24(11) (2019-05-31)
A UHPLC-QQQ-MS/MS method was developed to quantify the significant constituents in Wen-Dan Decoction (WDD), a traditional Chinese medicine. Analysis of 19 compounds was conducted on an ACQUITY UPLC® BEH C18 Column (2.1 × 50 mm, 1.7 μm) using elution with
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