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Naringenin

Naringenin

Product ID N0068
Cas No. 67604-48-2
Purity ≥98%
Product Unit SizeCostQuantityStock
5 g $105.30 In stock
10 g $172.60 In stock
25 g $285.60 In stock
Bulk Quote

Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
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  • Downloads
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Description

Naringenin is a phytoestrogen and flavanone found in citrus fruits. Naringenin exhibits antioxidative, anti-inflammatory, hepatoprotective, neuroprotective, immunomodulatory, anti-metastatic, anti-asthma, anti-allergic, anti-fibrotic, anti-metastatic, antiviral, antidepressant, anticancer, and gastrointestinal motility modulating activities. Naringenin inhibits oxidative damage in animal models of Alzheimer’s disease and protects against 6-OHDA-induced neurodegeneration by increasing levels of Nrf2 in animal models of Parkinson’s disease. In animal models of CCl4-induced liver injury, naringenin inhibits lipid peroxidation, increases levels of glutathione, HO-1, and Nrf2, and decreases levels of TNF-α, COX-2, and iNOS. In macrophages, naringenin alters expression of toll-like receptors 2 and 4 (TLR2, TLR4) and CD86; it also inhibits Treg-induced suppression and limits metastasis in animal models. In other animal models, naringenin inhibits allergen-induced airway inflammation. Naringenin also decreases levels of α-SMA, collagen type I, fibronectin, and ERK1/2 in fibroblasts. In leukemia cells, naringenin induces apoptosis, decreases the mitochondrial membrane potential and levels of Bcl-2, and increases levels of Bax. This compound also shows benefit in the tail suspension test and inhibits hepatitis C viral assembly.

Product Info

Cas No.

67604-48-2

Purity

≥98%

Formula

C15H12O5

Formula Wt.

272.25

Chemical Name

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

IUPAC Name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

Synonym

4',5,7-Trihydroxyflavanone, naringetol, salipurpol, pelargidanon 1602

Melting Point

247-250°C

Solubility

Insoluble in water. Soluble in ethanol (50 mg/mL), DMSO, methanol.

Appearance

White to yellow powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

N0068 MSDS PDF

Info Sheet

N0068 Info Sheet PDF

References

Esmaeili MA, Alilou M. Naringenin attenuates CCl4 -induced hepatic inflammation by the activation of an Nrf2-mediated pathway in rats. Clin Exp Pharmacol Physiol. 2014 Jun;41(6):416-22. PMID: 24684352.

Chtourou Y, Fetoui H, Gdoura R. Protective effects of naringenin on iron-overload-induced cerebral cortex neurotoxicity correlated with oxidative stress. Biol Trace Elem Res. 2014 Jun;158(3):376-83. PMID: 24682942.

Lou H, Jing X, Wei X, et al. Naringenin protects against 6-OHDA-induced neurotoxicity via activation of the Nrf2/ARE signaling pathway. Neuropharmacology. 2014 Apr;79:380-8. PMID: 24333330.

Kim S, Park TI. Naringenin: a partial agonist on estrogen receptor in T47D-KBluc breast cancer cells. Int J Clin Exp Med. 2013 Oct 25;6(10):890-9. PMID: 24260594.

Yilma AN, Singh SR, Morici L, et al. Flavonoid naringenin: a potential immunomodulator for Chlamydia trachomatis inflammation. Mediators Inflamm. 2013;2013:102457. PMID: 23766556.

Jang Y, Kim SW, Oh J, et al. Ghrelin receptor is activated by naringin and naringenin, constituents of a prokinetic agent Poncirus fructus. J Ethnopharmacol. 2013 Jul 9;148(2):459-65. PMID: 23639361.

Jung JW, Park IH, Cho JS, et al. Naringenin inhibits extracellular matrix production via extracellular signal-regulated kinase pathways in nasal polyp-derived fibroblasts. Phytother Res. 2013 Mar;27(3):463-7. PMID: 22674629.

Goldwasser J, Cohen PY, Lin W, et al. Naringenin inhibits the assembly and long-term production of infectious hepatitis C virus particles through a PPAR-mediated mechanism. J Hepatol. 2011 Nov;55(5):963-71. PMID: 21354229.

Qin L, Jin L, Lu L, et al. Naringenin reduces lung metastasis in a breast cancer resection model. Protein Cell. 2011 Jun;2(6):507-16. PMID: 21748601.

Yi LT, Li CF, Zhan X, et al. Involvement of monoaminergic system in the antidepressant-like effect of the flavonoid naringenin in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2010 Oct 1;34(7):1223-8. PMID: 20603175.

Shi Y, Dai J, Liu H, et al. Naringenin inhibits allergen-induced airway inflammation and airway responsiveness and inhibits NF-kappaB activity in a murine model of asthma. Can J Physiol Pharmacol. 2009 Sep;87(9):729-35PMID: 19794524.

Park JH, Jin CY, Lee BK, et al. Naringenin induces apoptosis through downregulation of Akt and caspase-3 activation in human leukemia THP-1 cells. Food Chem Toxicol. 2008 Dec;46(12):3684-90. PMID: 18930780.

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