(S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron

Naringenin

HCID 439246

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Grundinformationen

CAS: 480-41-1
Standard-SMILES: O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
Summenformel: C15H12O5
Durchschnittliche Molmasse: 272,25 g/mol
Monoisotopische Masse: 272,06847348

Überblick

(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.

Namen und Bezeichner

Bevorzugter Name: Naringenin
IUPAC: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Lokaler Name: (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron
Englischer Name: Naringenin
Summenformel: C15H12O5
Molmasse: 272.25

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,4
Polarare Oberfläche (TPSA): 87 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 1
Schwere Atome: 20
Formalladung: 0
Komplexität: 363

Experimentelle und physikochemische Eigenschaften

Chemical ClassesAntioxidant

DrugsPharmaceuticals -> Listed in ZINC15

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

SpringerMaterials PropertiesCrystal structure

LogP2.52

Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt: 247 · 247-250 °C(lit.)
Siedepunkt: 335.31 °C · 335.31°C (rough estimate)
Dichte: 1.2066 · 1.2066 (rough estimate)
Brechungsindex: 1.6 · 1.6000 (estimate)
FEMA: 4797 · 4797 | (+/-)-NARINGENIN
storage temp.: Inert atmosphere,Room Temperature
Löslichkeit: DMSO (Slightly), Methanol (Slightly, Sonicated)
Aggregatzustand: Powder
pka: 7.52 · 7.52±0.40(Predicted)
Farbe: Beige-brown
Kosmetik-Inhaltsstoffe Funktionen: SKIN CONDITIONING
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 Datenbank: 480 · 480-41-1(CAS DataBase Reference)
EPA chemische Informationen: 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (99.3%)

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

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.

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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 Einträge

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

Anwendungen

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