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N1376

Sigma-Aldrich

Naringin

≥90% (HPLC), from citrus fruit

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:
102012
EC Number:
233-566-4
MDL number:
MFCD00148888
UNSPSC Code:
12352201
PubChem Substance ID:
24897483
NACRES:
NA.25

biological source

citrus fruit

Assay

≥90% (HPLC)

form

powder

color

white to light yellow

solubility

ethanol: 50 mg/mL, slightly hazy to slightly hazy, light yellow to yellow

storage temp.

room temp

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

Naringin is a flavanone glycoside.

Application

Naringin has been used in a study to assess aldosterone production by a human adrenocortical cell line. Long-term naringin consumption reverses a glucose uptake defect and can be used to improve cognitive deficits of Alzheimer′s disease.

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.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Dongmei Wang et al.
Pharmacology, biochemistry, and behavior, 102(1), 13-20 (2012-06-29)
Naringin, a bioflavonoid, has been reported to have potent neuro-protective effects, but its preventive effects on amyloid-β (Aβ) induced, Alzheimer's disease (AD) related, cognitive impairment, and the underlying mechanisms of these effects have not been well characterised. Three-month-old APPswe/PSΔE9 transgenic
Denise C Endringer et al.
Journal of natural products, 71(6), 1082-1084 (2008-05-09)
Aromatase is a well-established target for the chemoprevention of breast cancer. The dihydroisocoumarin (3 R,4 R)-(-)-6-methoxy-1-oxo-3-pentyl-3,4-dihydro-1 H-isochromen-4-yl acetate (1) (IC 50 = 1.6 +/- 0.1 microM), isolated from aerial parts of Xyris pterygoblephara, showed aromatase inhibitory activity. The specificity of
Yi-Chu Nie et al.
Journal of medicinal food, 15(10), 894-900 (2012-09-19)
Naringin, a well-known flavanone glycoside of grapefruit and citrus fruits, was found to be as an effective anti-inflammatory compound in our previous lipopolysaccharide-induced acute lung injury mouse model via blockading activity of nuclear factor κB. The current study sought to
MinKyun Na et al.
Journal of natural products, 69(11), 1572-1576 (2006-11-28)
Inhibition of protein tyrosine phosphatase-1B (PTP1B) has been proposed as a therapy for treatment of type-2 diabetes and obesity. Bioassay-guided fractionation of an EtOAc-soluble extract of the root bark of Erythrina mildbraedii, using an in vitro PTP1B inhibitory assay, resulted
Kenji Oki et al.
Endocrinology, 153(9), 4328-4335 (2012-07-17)
Angiotensin II (A-II) regulation of aldosterone secretion is initiated by inducing cell membrane depolarization, thereby increasing intracellular calcium and activating the calcium calmodulin/calmodulin kinase cascade. Mutations in the selectivity filter of the KCNJ5 gene coding for inward rectifying potassium channel
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