FComEx: Naringin (PC000735)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:18 UTC

Update date

2017-01-19 02:36:34 UTC

FoodComEx ID

PC000735

FoodDB Record

FDB011866

Chemical Information

Name

Naringin

Description

obtained from citrus fruits, Clymenia polyandra (clymenia) and Origanum vulgare (oregano) Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. It is metabolized to the flavonone naringenin in humans. Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro. Naringin is found in many foods, some of which are fruits, common sage, lime, and citrus.

CAS Number

10236-47-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4'5-DiOH-flavone-7-rhgluc	HMDB
Aurantiin	db_source
Isohesperidin	db_source
Naringenin 7-neohesperidoside	db_source
Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside]	Generator
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]	biospider
Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside]	Generator
Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucoside	Generator
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside	ChEBI
Naringenin 7-O-neohesperidoside	biospider
Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucoside	Generator
Naringin	db_source
Naringin hydrate	HMDB
Naringoside	db_source

Chemical Formula

C27H32O14

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)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

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+/m0/s1

InChI Key

DFPMSGMNTNDNHN-ZPHOTFPESA-N

Isomeric SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

Average Molecular Weight

580.5346

Monoisotopic Molecular Weight

580.179205732

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Oxane
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:28819 )
dihydroxyflavanone (CHEBI:28819 )
neohesperidoside (CHEBI:28819 )
flavanones (C09789 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-0.44	PERRISSOUD,D & TESTA,B (1986)
Experimental Water Solubility	1 mg/mL at 40 oC	MERCK INDEX (1996)
Melting Point	Mp 171° (dihydrate)	DFC

Foods of Origin