Naringenin (HCID 439246)

개요

(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.

이름 및 식별자

우선 이름: Naringenin
IUPAC: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
현지명: 나린제닌
영어명: Naringenin
분자식: C15H12O5
분자량: 272.25

이름 및 동의어

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

이름 더 보기

나린제닌NARIGENIN5,7-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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 2.4
극성 표면적: 87 Å²
수소 결합 공여자 수: 3
수소 결합 수용자 수: 5
회전 가능 결합 수: 1
무거운 원자 수: 20
형식 전하: 0
복잡도: 363

실험 및 물리화학적 성질

Chemical ClassesAntioxidant

DrugsPharmaceuticals -> Listed in ZINC15

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

SpringerMaterials PropertiesCrystal structure

LogP2.52

Endocrine DisruptorsPotential endocrine disrupting compound

물리화학적 성질

녹는점: 247 · 247-250 °C(lit.)
끓는 점: 335.31 °C · 335.31°C (rough estimate)
밀도: 1.2066 · 1.2066 (rough estimate)
굴절률: 1.6 · 1.6000 (estimate)
FEMA: 4797 · 4797 | (+/-)-NARINGENIN
저장 조건: Inert atmosphere,Room Temperature
용해도: DMSO(약간 용해됨), 메탄올(약간 용해됨, 초음파처리)
물리적 상태: 가루
산도 계수 (pKa): 7.52 · 7.52±0.40(Predicted)
색상: 베이지 브라운
화장품 원료 기능: 피부 컨디셔닝
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
EPA: 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1)

화학적 성질

beige-brown powder

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesSkin Irrit. 2 (99.3%)

독성 정보

Toxicity Summary · 1건

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.

안전 데이터

wgk: 3
HS 번호: 29329990
risk_code: 36/37/38-22
hazard_code: Xi,Xn
safety_code: 26-36-37/39
위험 등급: IRRITANT

화학 및 산업

약리 정보

Mechanism of Action · 1건

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 · 2건

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

응용 분야

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