Merck
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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
Empirical Formula (Hill Notation):
C15H12O5
CAS Number:
Molecular Weight:
272.25
EC Number:
MDL number:
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.

Packaging

1 g in poly tube
5, 25 g in poly bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N5893.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

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

Certificate of Analysis

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Certificate of Origin

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