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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:
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

Quality Level

100

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
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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7419
BCCD8095
BCBZ4109
BCBX0396
BCBT8724

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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)
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)
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)
Hypochlorite scavenging activity of flavonoids
Firuzi O, et al.
The Journal of Pharmacy and Pharmacology, 56(6), 801-807 (2004)
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
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