Narirutin

Last updated
Narirutin
Narirutin.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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. Orange juice UHPLC UV chromatogram.png
Ultraviolet 280 nm chromatogram after UHPLC separation of commercial orange juice. Narirutin is peak at 14.65 min.

References

  1. 1 2 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".
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