Eriocitrin

Eriocitrin
Names
	IUPAC name (2S)-3′,4′,5-Trihydroxy-7-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavan-4-one
	Preferred 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
CAS Number	13463-28-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	75327;
ECHA InfoCard	100.033.321
PubChem CID	83489;
UNII	AS293HR5XQ ;
	InChI 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
Chemical formula	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

Eriocitrin (eriodictyol glycoside) is a flavanone-7-O-glycoside between the flavanone eriodictyol and the disaccharide rutinose. It is commonly found in lemons.^[1] 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.

The compound has lipid-lowering properties in liver cells.^[2] 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.

References[]

^ Miyake, Yoshiaki; Yamamoto, Kanefumi; Osawa, Toshihiko (1997). "Isolation of Eriocitrin (Eriodictyol 7-rutinoside) from Lemon Fruit (Citrus limon Burm. f.) and Its Antioxidative Activity". Food Science and Technology International, Tokyo. 3 (1): 84–89. doi:10.3136/fsti9596t9798.3.84. ISSN 1881-3976.
^ Hiramitsu, Masanori; Shimada, Yasuhito; Kuroyanagi, Junya; Inoue, Takashi; Katagiri, Takao; Zang, Liqing; Nishimura, Yuhei; Nishimura, Norihiro; Tanaka, Toshio (2014). "Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis". Scientific Reports. 4: 3708. Bibcode:2014NatSR...4E3708H. doi:10.1038/srep03708. PMC 3892443. PMID 24424211.

External links[]

Media related to Eriocitrin at Wikimedia Commons
Gel-Moreto, Nuria; Streich, René; Galensa, Rudolf (2003). "Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis". Electrophoresis. 24 (15): 2716–2722. doi:10.1002/elps.200305486. ISSN 0173-0835. PMID 12900888. S2CID 40261445.

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[MIYAKEYAMAMOTO1997-1] Miyake, Yoshiaki; Yamamoto, Kanefumi; Osawa, Toshihiko (1997). "Isolation of Eriocitrin (Eriodictyol 7-rutinoside) from Lemon Fruit (Citrus limon Burm. f.) and Its Antioxidative Activity". Food Science and Technology International, Tokyo. 3 (1): 84–89. doi:10.3136/fsti9596t9798.3.84. ISSN 1881-3976.

[2] Hiramitsu, Masanori; Shimada, Yasuhito; Kuroyanagi, Junya; Inoue, Takashi; Katagiri, Takao; Zang, Liqing; Nishimura, Yuhei; Nishimura, Norihiro; Tanaka, Toshio (2014). "Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis". Scientific Reports. 4: 3708. Bibcode:2014NatSR...4E3708H. doi:10.1038/srep03708. PMC 3892443. PMID 24424211.

[1]

[2]

v t Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin (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

v t 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

Names

IUPAC name (2S)-3′,4′,5-Trihydroxy-7-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavan-4-one
Preferred 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
CAS Number	13463-28-0^Y
3D model (JSmol)	Interactive image
ChemSpider	75327
ECHA InfoCard	100.033.321
PubChem CID	83489
UNII	AS293HR5XQ^Y
InChI 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
Chemical formula	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

Eriocitrin

See also[]

References[]

External links[]