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N5893

Sigma-Aldrich

(±)-Naringenin

≥95%

Synonym(s):

(±)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 4′,5,7-Trihydroxyflavanone

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About This Item

Empirical Formula (Hill Notation):
C15H12O5
CAS Number:
Molecular Weight:
272.25
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95%

form

powder

mp

247-250 °C (lit.)

SMILES string

OC1=CC=C(C=C1)C(C2)OC3=CC(O)=CC(O)=C3C2=O

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

InChI key

FTVWIRXFELQLPI-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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Application

(±)-Naringenin, a polyphenolic material, is used to prepare nickel(II) naringenin-oxime complex, which can be used as a catalyst for Mizoroki−Heck cross-coupling reaction. It has been used as a hypochlorite scavenger to prevent the formation of chloramines from oxidation of hypochlorite in the human serum albumin. It induces apoptosis in human pancreatic cancer SNU-213 cells. It also shows cytotoxic effects on various human cancer cells such as breast, cervix, stomach, colon and liver cancer cells.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Efficient nickel (ii) naringenin-oxime complex catalyzed Mizoroki-Heck cross-coupling reaction in the presence of hydrazine hydrate
Song JY, et al.
New. J. Chem., 41(20), 12288-12292 (2017)
Naringenin causes ASK1-induced apoptosis via reactive oxygen species in human pancreatic cancer cells
Park HJ, et al.
Food And Chemical Toxicology, 99(6), 1-8 (2017)
Amy C Burke et al.
Journal of lipid research, 59(9), 1714-1728 (2018-07-17)
Obesity and its associated metabolic dysfunction and cardiovascular disease risk represent a leading cause of adult morbidity worldwide. Currently available pharmacological therapies for obesity have had limited success in reversing existing obesity and metabolic dysregulation. Previous prevention studies demonstrated that
Krista A Power et al.
Molecular nutrition & food research, 60(11), 2396-2412 (2016-06-29)
This study investigated the effects of cooked whole asparagus (ASP) versus its equivalent level of purified flavonoid glycoside, rutin (RUT), on dextran sodium sulfate (DSS)-induced colitis and subsequent colitis recovery in mice. C57BL/6 male mice were fed an AIN-93G basal
Hypochlorite scavenging activity of flavonoids
Firuzi O, et al.
The Journal of Pharmacy and Pharmacology, 56(6), 801-807 (2004)

Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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