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Y0001378

Naringin

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

4′,5,7-Trihydroxyflavanone 7-rhamnoglucoside, Naringenin 7-neohesperidoside, Naringenine-7-rhamnosidoglucoside, Naringoside

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About This Item

Empirical Formula (Hill Notation):
C27H32O14
CAS Number:
10236-47-2
Molecular Weight:
580.53
Beilstein/REAXYS Number:
102012
MDL number:
MFCD00148888
UNSPSC Code:
41116107
PubChem Substance ID:
329831392
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

naringin

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc3cc(O)c4C(=O)CC(Oc4c3)c5ccc(O)cc5)[C@H](O)[C@H](O)[C@H]1O

InChI

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

InChI key

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Naringin EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Related product

Product No.
Description
Pricing

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Mustafa Ozyürek et al.
Chemico-biological interactions, 212, 40-46 (2014-02-11)
Recent interest in polyphenolic antioxidants due to their involvement in health benefits has led to the investigation of new polyphenolic compounds with enhanced antioxidant activity. Naringin (4',5,7-trihydroxyflavanone-7-β-l-rhamnoglucoside-(1,2)-α-d-glucopyranoside) is one of the major flavanones in citrus and grapefruit. The present study
Bidya Dhar Sahu et al.
Toxicology and applied pharmacology, 277(1), 8-20 (2014-03-19)
Gentamicin-induced nephrotoxicity has been well documented, although its underlying mechanisms and preventive strategies remain to be investigated. The present study was designed to investigate the protective effect of naringin, a bioflavonoid, on gentamicin-induced nephrotoxicity and to elucidate the potential mechanism.
M A Nguyen et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 68, 36-42 (2014-12-09)
Naringin is considered the major causative ingredient of the inhibition of intestinal drug uptake by grapefruit juice. Moreover, it is contained in highly dosed nutraceuticals available on the market. A controlled, open, randomized, crossover study was performed in 10 healthy
Su-Chen Ho et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 71, 176-182 (2014-06-24)
Inhibiting microglial activation-mediated neuroinflammation has become a convincing target for the development of functional foods to treat neurodegenerative diseases. Tangerine peel (Citri reticulatae pericarpium) has potent anti-inflammatory capacity; however, its anti-neuroinflammatory capacity and the corresponding active compounds remain unclear. To
Feng-Quan Tan et al.
BMC plant biology, 15, 89-89 (2015-04-08)
Polyploidy has often been considered to confer plants a better adaptation to environmental stresses. Tetraploid citrus rootstocks are expected to have stronger stress tolerance than diploid. Plenty of doubled diploid citrus plants were exploited from diploid species for citrus rootstock
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