FComEx: Naringin (PC001099)

Record Information

Version

1.0

Creation date

2018-04-10 12:19:41 UTC

Update date

2018-04-17 12:34:18 UTC

FoodComEx ID

PC001099

FoodDB Record

FDB011866

Chemical Information

Name

Naringin

Description

Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. It is metabolized to the flavonone naringenin in humans.

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

Class

Polyphenols

Family

Flavanones

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

grapefruit

Production Data

Production Method

commercial

Production Method Reference

Not Available

Production Method Reference File

Not Available

Quantity Available

1 to 5 mg

Delivery Time