Naringin

Naringin
Names
	IUPAC name (2S)-4′,5-Dihydroxy-7-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]flavan-4-one
	Systematic IUPAC name (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
	Other names Naringin; Naringoside; 4′,5,7-Trihydroxyflavanone-7-rhamnoglucoside; Naringenin 7-O-neohesperidoside
Identifiers
CAS Number	10236-47-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28819 ;
ChEMBL	ChEMBL451512 ;
ChemSpider	4447695 ;
ECHA InfoCard	100.030.502
IUPHAR/BPS	4738;
KEGG	C09789 ;
PubChem CID	442428;
UNII	N7TD9J649B ;
CompTox Dashboard (EPA)	DTXSID6022478 ;
	InChI InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1 Key: DFPMSGMNTNDNHN-CSIAVLANSA-N ; InChI=1/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1 Key: DFPMSGMNTNDNHN-CSIAVLANBN;
	SMILES O=C4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C)cc5O[C@H](c3ccc(O)cc3)C4;
Properties
Chemical formula	C27H32O14
Molar mass	580.54 g/mol
Melting point	166 °C (331 °F; 439 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Naringin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness (debittering) created by naringin. In humans naringin is metabolized to the aglycone naringenin (not bitter) by naringinase present in the gut.

Names


IUPAC name (2S)-4′,5-Dihydroxy-7-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]flavan-4-one
Systematic IUPAC name (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names Naringin Naringoside 4′,5,7-Trihydroxyflavanone-7-rhamnoglucoside Naringenin 7-O-neohesperidoside
Identifiers
CAS Number	10236-47-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28819^N
ChEMBL	ChEMBL451512^N
ChemSpider	4447695^Y
ECHA InfoCard	100.030.502
IUPHAR/BPS	4738
KEGG	C09789^Y
PubChem CID	442428
UNII	N7TD9J649B^Y
CompTox Dashboard (EPA)	DTXSID6022478
InChI InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1^Y Key: DFPMSGMNTNDNHN-CSIAVLANSA-N^Y InChI=1/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1 Key: DFPMSGMNTNDNHN-CSIAVLANBN
SMILES O=C4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C)cc5O[C@H](c3ccc(O)cc3)C4
Properties
Chemical formula	C₂₇H₃₂O₁₄
Molar mass	580.54 g/mol
Melting point	166 °C (331 °F; 439 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references