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71162

Sigma-Aldrich

Naringin

≥95% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C27H32O14
Número de CAS:
10236-47-2
Peso molecular:
580.53
Beilstein:
102012
Número CE:
233-566-4
Número MDL:
MFCD00148888
Código UNSPSC:
12352201
ID de la sustancia en PubChem:
57652274
NACRES:
NA.47

Nivel de calidad

200

Ensayo

≥95% (HPLC)

Formulario

powder

actividad óptica

[α]20/D −80±10°, c = 1% in ethanol

mp

83  °C ((181 °F ))

solubilidad

ethanol: o.1 g/10 mL, clear to hazy, colorless to light greenish-yellow

cadena SMILES

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

Clave InChI

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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Categorías relacionadas

Aplicación

Naringin has been used:
  • as a bitter tastant to compare the behavioral response of the Drosophila larva and adult(2)
  • to study its anti-inflammatory property and to determine its effect on nucleus pulposus (NP) cells(3)
  • to determine its effect on bone metabolism like osteogenic differentiation, inhibition of osteoclast formation(4)

Acciones bioquímicas o fisiológicas

Naringin can interact with signaling molecules and modulates signaling pathways. It possesses anti-inflammatory and anti-cancer activities. It also exhibits pharmacological effects on oxidative stress, bone regeneration, genetic damage, metabolic syndrome and central nervous system (CNS) diseases.
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.

Otras notas

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCG5679
BCCF4512
BCCC2187
BCCB6611
BCCB3021

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Therapeutic potential of naringin: an overview
Chen R, et al.
Pharmaceutical biology, 54(12), 3203-3210 (2016)
Marcelo Silva et al.
Industrial & engineering chemistry research, 57(28), 9210-9221 (2018-10-03)
Liquid-liquid extraction (LLE) can be an effective strategy for the purification of polyphenols from a fermentation broth. However, solvents need to be chosen to ensure high extraction capacity and selectivity. For that purpose, a systematic study is here presented, where
Luís F Mendes et al.
Scientific reports, 9(1), 14906-14906 (2019-10-19)
The ability of flavonoids to attenuate macrophage pro-inflammatory activity and to promote macrophage-mediated resolution of inflammation is still poorly understood at the biochemical level. In this study, we have employed NMR metabolomics to assess how therapeutically promising flavonoids (quercetin, naringenin
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
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