Narirutin

Narirutin
Names

Other names Naringenin-7-O-rutinoside
Identifiers
CAS Number	14259-46-2
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28705
ChemSpider	390871
ECHA InfoCard	100.034.655
KEGG	C09793
PubChem	442431
InChI InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1 Key: HXTFHSYLYXVTHC-AJHDJQPGSA-N InChI=1/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1 Key: HXTFHSYLYXVTHC-AJHDJQPGBL
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
Properties
Chemical formula	C₂₇H₃₂O₁₄
Molar mass	580.54 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Narirutin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide rutinose.

It is found in orange juice.^[1]

Ultraviolet 280 nm chromatogram after UHPLC separation of commercial orange juice. Narirutin is peak at 14.65 min.

References

↑ Interferences with naringin and neohesperidin analysis by high performance liquid chromatography. Widmer W.W and Martin S.F., 1993

Rouseff, Russell L.; Martin, Shirley F.; Youtsey, Charles O. (1987). "Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus". Journal of Agricultural and Food Chemistry. 35 (6): 1027–1030. doi:10.1021/jf00078a040. ISSN 0021-8561.

Flavanones and their glycosides

Flavanones	Butin Eriodictyol Naringenin Pinocembrin

O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin

C-methylated flavanones	Poriol

Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin

Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G

Acetylated glycosides	Nirurin

Glycosides

Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond

Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside

Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside

Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

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