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Merck
CN

91842

Naringin

analytical 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
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329770089
EC Number:
233-566-4
Beilstein/REAXYS Number:
102012
MDL number:
MFCD00148888

Key Documents

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Product Name

Naringin, analytical standard

InChI key

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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

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

grade

analytical standard

assay

≥95.0% (HPLC)

optical activity

[α]/D -80±10°, c = 1 in ethanol

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

General description

Naringin is a naturally occurring flavone glycoside, which may possess many pharmacological properties like anti-inflammatory, anti-oxidant and anti-apoptotic activity. It is widely found in fruits like grapes and oranges.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6916
BCCL5113
BCCK9219
BCCJ2905
BCCF2214

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Therapeutic effects of silymarin and naringin on methotrexate?induced nephrotoxicity in rats: Biochemical evaluation of anti?inflammatory, antiapoptotic, and antiautophagic properties
Kandemir MF, et al.
Journal of Food Biochemistry, 41 (2017)
Naringin ameliorates diabetic nephropathy by inhibiting NADPH oxidase 4
Zhang J, et al.
European Journal of Pharmacology, 804, 1-6 (2017)
Jiukai Zhang et al.
Food chemistry, 135(3), 1471-1478 (2012-09-08)
Huyou (Citrus changshanensis) is rich in naringin and neohesperidin, which are natural flavanone glycosides with a range of biological activities. Among the different fruit parts, i.e. flavedo, albedo, segment membrane (SM), and juice sacs (JS), albedo showed the highest contents
E Ramesh et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 97-105 (2012-08-01)
Cervical cancer is the second most common female cancer worldwide, and it remains a challenge to manage preinvasive and invasive lesions. Fruit-based cancer prevention entities, such as flavonoid and their derivatives, have demonstrated a marked ability to inhibit preclinical models
Ayman M Mahmoud et al.
Journal of diabetes and its complications, 26(6), 483-490 (2012-07-20)
Abnormal regulation of glucose and impaired carbohydrate utilization that result from a defective or deficient insulin are the key pathogenic events in type 2 diabetes mellitus (T2DM). The present study was hypothesized to investigate the beneficial effects of hesperidin and
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