Naringin

HCID 442428CAS 10236-47-2

基本情報

標準SMILES: C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChIKey: DFPMSGMNTNDNHN-ZPHOTFPESA-N
分子式: C27H32O14
平均分子量: 580.5 g/mol
単同位体質量: 580.1792057

概要

Naringin is a disaccharide derivative that is (S)-naringenin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a metabolite, an antineoplastic agent and an anti-inflammatory agent. It is a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one, a neohesperidoside, a dihydroxyflavanone and a disaccharide derivative. It is functionally related to a (S)-naringenin.

名称と識別子

優先名称: Naringin
IUPAC: (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]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

名称と別名

naringin10236-47-2aurantiinNaringosideNaringenin 7-O-neohesperidosideN7TD9J649BNaringenin-7-beta-neohesperidoside(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]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneDTXSID6022478CHEBI:28819(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-one5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon

名称をさらに表示

Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]4',5,7-trihydroxyflavanone 7-rhamnoglucosideNaringenin 7-O-(alpha-L-rhamnosyl-(1->2)-beta-D-glucoside)Citrus naringinine(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(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)oxyoxan-2-yl)oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one(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)oxyoxan-2-yl)oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one(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]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

データベース識別子

CAS: 10236-47-2
PubChem CID: 442428
DTXSID: DTXSID6022478
ChEMBL: CHEMBL451532
ChEBI: CHEBI:28819
UNII: N7TD9J649B
EC Number: 233-566-4
Nikkaji: J10.482E

物性

構造計算による物性

XLogP: -0.5
極性表面積: 225 Å²
水素結合供与体数: 8
水素結合受容体数: 14
回転可能結合数: 6
重原子数: 41
形式電荷: 0
複雑度: 884

実験および物理化学的性質

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]

LogP · 2 件

-0.44

Flavoring AgentsEU Flavoring substances

Solubility1 mg/mL at 40 °C

Boiling Point922.00 to 926.00 °C. @ 760.00 mm Hg

Melting Point83 °C

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 76.1% (143 of 188) of all reports.

Warning

H315 (23.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 188 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (S)-

Regulation (EC) No 1831/2003 (amended)

Status: Active Update: 11-10-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20764

Naringin: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

Hazard Classes and CategoriesSkin Irrit. 2 (23.9%)

化学と産業

薬理情報

Tissue LocationsEpidermis

Cellular LocationsCytoplasm

用途と製造

General Manufacturing Information4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-: ACTIVE