Naringenin (HCID 439246)

概要

(S)-naringenin is the (S)-enantiomer of naringenin. It has a role as a plant metabolite and an expectorant. It is a (2S)-flavan-4-one and a naringenin. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin.

名称と識別子

優先名称: Naringenin
IUPAC: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
現地名: (2S)-2-(4-ヒドロキシフェニル)-5,7-ジヒドロキシ-2,3-ジヒドロ-4H-1-ベンゾピラン-4-オン
英語名: Naringenin
分子式: C15H12O5
分子量: 272.25

名称と別名

naringenin480-41-1(S)-Naringeninsalipurpol(2S)-NaringeninNaringenineSalipurolnaringetolpelargidanon5,7,4'-Trihydroxyflavanone(-)-(2S)-NaringeninHN5425SBF2

名称をさらに表示

(S)-ナリンゲニン(2S)-ナリンゲニン(2S)-2-(4-ヒドロキシフェニル)-5,7-ジヒドロキシ-2,3-ジヒドロ-4H-1-ベンゾピラン-4-オン(2S)-2α-(4-ヒドロキシフェニル)-5,7-ジヒドロキシ-2,3-ジヒドロ-4H-1-ベンゾピラン-4-オン(S)-2,3-ジヒドロ-2-(4-ヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オンナリンゲトール(-)-ナリンゲニン(2S)-4',5,7-トリヒドロキシフラバノンナリンゲニン(2S)-2,3-ジヒドロ-5,7-ジヒドロキシ-2-(4-ヒドロキシフェニル)-4H-1-ベンゾピラン-4-オン5,7,4′-トリヒドロキシフラバノン(2S)-4′,5,7-トリヒドロキシフラバノン(2S)-5,7-ジヒドロキシ-2-(4-ヒドロキシフェニル)-3,4-ジヒドロ-2H-1-ベンゾピラン-4-オン(-)-5,7,4′-トリヒドロキシフラバノンNARIGENIN5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE(S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroMan-4-one5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-oneringenin(2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

(S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneDTXSID1022392CHEBI:17846(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneNSC-11855NSC-34875CHEBI:50202BE-14348A

データベース識別子

CAS: 480-41-1
PubChem CID: 439246
DTXSID: DTXSID1022392
ChEMBL: CHEMBL9352
ChEBI: CHEBI:17846
UNII: HN5425SBF2
EC Number: 207-550-2
Nikkaji: J325.849A

物性

構造計算による物性

XLogP: 2.4
極性表面積: 87 Å²
水素結合供与体数: 3
水素結合受容体数: 5
回転可能結合数: 1
重原子数: 20
形式電荷: 0
複雑度: 363

実験および物理化学的性質

Chemical ClassesAntioxidant

DrugsPharmaceuticals -> Listed in ZINC15

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

SpringerMaterials PropertiesCrystal structure

LogP2.52

Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点: 247 · 247-250 °C(lit.)
沸点: 335.31 °C · 335.31°C (rough estimate)
比重(密度): 1.2066 · 1.2066 (rough estimate)
屈折率: 1.6 · 1.6000 (estimate)
FEMA: 4797 · 4797 | (+/-)-NARINGENIN
貯蔵温度: Inert atmosphere,Room Temperature
溶解性: DMSO（わずかに）、メタノール（わずかに、超音波処理）
外見: 粉
酸解離定数(Pka): 7.52 · 7.52±0.40(Predicted)
色: ベージュブラウン
化粧品成分の機能: スキンコンディショニング
InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
SMILES: [C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C(=O)C1
LogP: 2.52 · 2.520
CAS データベース: 480 · 480-41-1(CAS DataBase Reference)
EPAの化学物質情報: 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1)

化学的性質

化学的特性beige-brown powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (99.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 305 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (99.3%)

毒性情報

Toxicity Summary · 1 件

A 2022 review notes that Naringenin has protective effects against toxicities produced by various natural toxins, pharmaceuticals, heavy metals, and environmental chemicals, and that the effects are mainly mediated via suppression of lipid peroxidation, oxidative stress (one example is lead), and inflammatory factors (one example is daunorubicin), and the activation of PI3K/Akt and MAPK survival signaling pathways.

安全データ

wgk: 3
hs_code: 29329990
risk_code: 36/37/38-22
hazard_code: Xi,Xn
safety_code: 26-36-37/39
hazard_class: IRRITANT

化学と産業

薬理情報

Mechanism of Action · 1 件

A 2021 review notes that the anti-inflammatory and antioxidant activities are via mechanisms such as enhancement of glutathione S-transferase, superoxide dismutase, glutathione peroxidase, and catalase activity, while reducing serum levels of alanine aminotransferase, aspartate aminotransferase, lactate dehydrogenase, and malondialdehyde. The review also notes that the anti-apoptotic potential was mediated by regulating B-cell leukemia/lymphoma 2 (Bcl-2), Bcl-2-associated X protein, and caspase-3/9.

MeSH Pharmacological Classification · 2 件

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.

Tissue LocationsFibroblasts

Cellular LocationsMembrane

応用分野

使用The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions

調製方法

純化方法Crystallise it from EtOH or aqueous EtOH. It has UV: at 290nm (EtOH). The S(-)-enantiomer (natural form) has m 255-256o (from EtOH) and [] D -28.0o (c 2, EtOH), [] D -35.2o (c 1, pyridine).