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Sigma-Aldrich

Naringin

≥95% (HPLC)

Synonym(e):

4′,5,7-Trihydroxyflavanon-7-rhamnoglucosid, Naringenin-7-neohesperidosid, Naringenin-7-rhamnosidoglucosid, Naringosid

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About This Item

Empirische Formel (Hill-System):
C27H32O14
CAS-Nummer:
10236-47-2
Molekulargewicht:
580.53
Beilstein:
102012
EG-Nummer:
233-566-4
MDL-Nummer:
MFCD00148888
UNSPSC-Code:
12352201
PubChem Substanz-ID:
57652274
NACRES:
NA.47

Assay

≥95% (HPLC)

Form

powder

Optische Aktivität

[α]20/D −80±10°, c = 1% in ethanol

mp (Schmelzpunkt)

83  °C ((181 °F ))

Löslichkeit

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

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

InChIKey

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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Verwandte Kategorien

Anwendung

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. Wirkung

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.

Sonstige Hinweise

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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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