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Merck

71162

Naringin

≥95% (HPLC)

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C27H32O14
Número CAS:
10236-47-2
Peso molecular:
580.53
UNSPSC Code:
12352201
NACRES:
NA.47
PubChem Substance ID:
57652274
EC Number:
233-566-4
Beilstein/REAXYS Number:
102012
MDL number:
MFCD00148888

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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

assay

≥95% (HPLC)

form

powder

optical activity

[α]20/D −80±10°, c = 1% in ethanol

mp

83  °C ((181 °F ))

solubility

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

Quality Level

200

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Application

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)

Biochem/physiol Actions

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.

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCN3099
BCCL8754
BCCJ7548
BCCG5679
BCCF4512

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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
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
Therapeutic potential of naringin: an overview
Chen R, et al.
Pharmaceutical biology, 54(12), 3203-3210 (2016)
Susana Ferreyra et al.
Food chemistry, 338, 128030-128030 (2020-09-16)
A liquid chromatography method coupling diode-array and fluorescence detectors (DAD and FLD, respectively) has been developed for the simultaneous quantification of 32 phenolic compounds (PCs) in winemaking products. With the combination of both detectors it was possible to determine phenolic
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
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