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71162 Sigma-Aldrich

Naringin

≥95% (HPLC)

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

  • CAS Number 10236-47-2

  • Empirical Formula (Hill Notation) C27H32O14

  • Molecular Weight 580.53

  •  Beilstein/REAXYS Number 102012

  •  EC Number 233-566-4

  •  MDL number MFCD00148888

  •  PubChem Substance ID 57652274

  •  NACRES NA.47

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Properties

Related Categories Cell Biology, Hematology and Histology, Natural Dyes, Stains and Dyes
Quality Level   200
assay   ≥95% (HPLC)
optical activity   [α]20/D −80±10°, c = 1% in ethanol
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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
QN6340000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

HPLC Analysis of Grapefruit Juice on Ascentis® Express C18 Column

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Grapefruit Juice on Ascentis® Express C18 Column
Keywords: Chromatography, High performance liquid chromatography, Mass spectrometry, Sample preparations, Solid phase extractions

Peer-Reviewed Papers
15

References

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