71162

Naringin

≥95% (HPLC)

• Synonym(s): 4′,5,7-Trihydroxyflavanone 7-rhamnoglucoside, Naringenin 7-neohesperidoside, Naringenine-7-rhamnosidoglucoside, Naringoside
• Empirical Formula (Hill Notation): C₂₇H₃₂O₁₄
• CAS Number: 10236-47-2
• Molecular Weight: 580.53
• Beilstein/REAXYS Number: 102012
• EC Number: 233-566-4
• MDL number: MFCD00148888
• UNSPSC Code: 12352201
• PubChem Substance ID: 57652274
• NACRES: NA.47

Properties

• 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
• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves