Eriocitrin

Eriocitrin (eriodictyol glycoside) is a flavanone-7-O-glycoside between the flavanone eriodictyol and the disaccharide rutinose. It is commonly found in lemons and other citrus fruits. It is colloquially called lemon flavonoid or a citrus flavonoid, one of the plant pigments that bring color to fruit and flowers. This antioxidant also predominates (38% in 1 study) in Peppermint infusions.

Eriocitrin
Names
IUPAC name
(2S)-3′,4′,5-Trihydroxy-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)-13,14,25,43,44,45,73,74,75-Nonahydroxy-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
Eriodictyol glycoside
Eriodictyol-7-O-rutinoside
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.033.321
KEGG
PubChem CID
UNII
  • InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
    Key: OMQADRGFMLGFJF-MNPJBKLOSA-N
  • InChI=1/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
    Key: OMQADRGFMLGFJF-MNPJBKLOBI
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)Oc3cc(c4c(c3)O[C@@H](CC4=O)c5ccc(c(c5)O)O)O)O)O)O)O)O)O
Properties
C27H32O15
Molar mass 596.538 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

The compound has lipid-lowering properties in liver cells. It is marketed as a dietary supplement, usually in conjunction with B and C vitamins and other substances, but there is no established medical use or FDA approved application of the compound.

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