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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

Quality Level

200

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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Flavanones in oranges, tangerines (mandarins), tangors, and tangelos: a compilation and review of the data from the analytical literature
Peterson J J, et al.,
Journal of food composition and analysis, 19, S66-S73 (2006)
Xiu-Min Chen et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 105, 398-406 (2017-04-17)
Dry citrus peels, also known as "chenpi", have been traditionally used to treat and relieve intestinal inflammation. Recently we have reported that orange peel extracts (OPE) which contain relatively greater polymethoxylated flavone (PMF) content exhibit superior antioxidant and anti-inflammatory activities
Shuai Wang et al.
Pharmacognosy magazine, 13(51), 372-377 (2017-08-26)
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.
Sang Keun Ha et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(10), 3498-3504 (2012-07-21)
In this study, we examined the regulatory activity of narirutin fraction from citrus peels on the production of inflammatory mediators managing acute or chronic inflammatory diseases in macrophages. Narirutin fraction inhibited the release, by lipopolysaccharide (LPS)-stimulated macrophages, of nitric oxide
Sandipan Chakraborty et al.
International journal of biological macromolecules, 103, 733-743 (2017-05-23)
Alzheimer's disease (AD) is a complex disorder and the disease mechanism is yet to be properly characterized. Over the years, "amyloid cascade" emerges as principal pathogenic event in AD. β-Secretase 1 (BACE1) controls the rate-limiting step in amyloid beta (Aβ)
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