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T66001

Sigma-Aldrich

Naringenin

Synonym(s):

(±)-Naringenin, (±)-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:
24900390

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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Description
Pricing

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)

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Senem Kamiloglu et al.
Journal of the science of food and agriculture, 94(11), 2225-2233 (2014-01-01)
In order to investigate the effect of home processing on the bioaccessibility of health-related constituents of tomatoes, total lycopene, phenolics, flavonoids and antioxidant capacity were determined from seven different tomato products using an in vitro gastrointestinal digestion model. Additionally, the
Nada Oršolić et al.
European journal of nutrition, 53(5), 1217-1227 (2013-11-26)
Reactive oxygen species play a role in a number of degenerative conditions including osteoporosis. Flavonoids as phyto-oestrogens exert physiological effects against oxidative stress diseases. We developed a retinoic acid-induced bone loss model of rats to assess whether flavonoids and alendronate
S Bhattacharya et al.
Diabetes, obesity & metabolism, 16(7), 602-612 (2013-11-12)
Caffeic acid, naringenin and quercetin are naturally occurring phenolic compounds (PCs) present in many plants as secondary metabolites. The aim of this study was to investigate their effect on glucose-stimulated insulin secretion (GSIS) in INS-1E cells and to explore their
Philipp Zeyhle et al.
PloS one, 9(6), e99122-e99122 (2014-06-04)
Recently, novel prenylated derivatives of 1,6-dihydroxyphenazine have been isolated from the marine sponge-associated Streptomyces sp. SpC080624SC-11. Genome sequencing of this strain now revealed a gene cluster containing all genes necessary for the synthesis of the phenazine and the isoprenoid moieties.
Julia M Assini et al.
Endocrinology, 156(6), 2087-2102 (2015-03-17)
The molecular mechanisms and metabolic pathways whereby the citrus flavonoid, naringenin, reduces dyslipidemia and improves glucose tolerance were investigated in C57BL6/J wild-type mice and fibroblast growth factor 21 (FGF21) null (Fgf21(-/-)) mice. FGF21 regulates energy homeostasis and the metabolic adaptation
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