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71162

Sigma-Aldrich

Naringin

≥95% (HPLC)

Synonim(y):

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

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About This Item

Wzór empiryczny (zapis Hilla):
C27H32O14
Numer CAS:
10236-47-2
Masa cząsteczkowa:
580.53
Beilstein:
102012
Numer WE:
233-566-4
Numer MDL:
MFCD00148888
Kod UNSPSC:
12352201
Identyfikator substancji w PubChem:
57652274
NACRES:
NA.47

Próba

≥95% (HPLC)

Postać

powder

aktywność optyczna

[α]20/D −80±10°, c = 1% in ethanol

mp

83  °C ((181 °F ))

rozpuszczalność

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

ciąg 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

Klucz InChI

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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Zastosowanie

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)

Działania biochem./fizjol.

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.

Inne uwagi

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.
This page may contain text that has been machine translated.

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 2

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

dust mask type N95 (US), Eyeshields, Gloves

Certyfikaty analizy (CoA)

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Prunin ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00076

Prunin

Hesperidin analytical standard

Supelco

50162

Hesperidin

Narirutin ≥98% (HPLC)

Sigma-Aldrich

SMB00321

Narirutin

Naringin dihydrochalcone phyproof® Reference Substance

PHL83338

Naringin dihydrochalcone

Neohesperidin ≥90% (HPLC)

Sigma-Aldrich

N1887

Neohesperidin

Neoeriocitrin ~95% (HPLC)

Sigma-Aldrich

72129

Neoeriocitrin

Naringenin-6-C-glucoside ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00137

Naringenin-6-C-glucoside

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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