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Narirutin

Narirutin
Names
IUPAC name
(2S)-4′,5-Dihydroxy-7-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavan-4-one
Systematic IUPAC name
(22S,42S,43R,44S,45S,46R,72R,73R,74R,75R,76S)-14,25,43,44,45,73,74,75-Octahydroxy-76-methyl-22,23-dihydro-24H-3,6-dioxa-2(2,7)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-24-one
Other names
Naringenin-7-O-rutinoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.034.655
KEGG
UNII
  • 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
  • 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
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).

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. ^ a b 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".
  • Media related to Narirutin at Wikimedia Commons
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