Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C15H12O5
CAS Number:
67604-48-2
Molecular Weight:
272.25
EC Number:
266-769-1
MDL number:
MFCD00006844
UNSPSC Code:
12352100
PubChem Substance ID:
57654457
NACRES:
NA.22

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
Hypochlorite scavenging activity of flavonoids
Firuzi O, et al.
The Journal of Pharmacy and Pharmacology, 56(6), 801-807 (2004)
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
Inhibitory effects of naringenin on tumor growth in human cancer cell lines and sarcoma S-180-implanted mice
Kanno S, et al.
Biological & Pharmaceutical Bulletin, 28(3), 527-530 (2005)
View All Related Papers

Articles

Dietary Antioxidants

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service