Narirutin

Narirutin

Names
IUPAC name (2S)-4′,5-Dihydroxy-7-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavan-4-one
Systematic IUPAC name (2^2S,4^2S,4^3R,4^4S,4^5S,4^6R,7^2R,7^3R,7^4R,7^5R,7^6S)-1^4,2^5,4^3,4^4,4^5,7^3,7^4,7^5-Octahydroxy-7^6-methyl-2^2,2^3-dihydro-2^4H-3,6-dioxa-2(2,7)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-2^4-one
Other names Naringenin-7-O-rutinoside
Identifiers
CAS Number	14259-46-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28705
ChemSpider	390871
ECHA InfoCard	100.034.655
KEGG	C09793
PubChem CID	442431
UNII	06M5EAT0YC^Y
CompTox Dashboard (EPA)	DTXSID30931535
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	580.539 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, consisting of the flavanone naringenin bonded with the disaccharide rutinose.[1]

It is found in orange juice.[1][2]

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

References

1. 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.
2. Widmer W.W and Martin S.F. (1993). "Interferences with naringin and neohesperidin analysis by high performance liquid chromatography".

External links

• Media related to Narirutin at Wikimedia Commons