Naringenin | CAS#480-41-1 | Bioflavonoid

MedKoo Cat#: 527706 | Name: Naringenin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Naringenin is a bioflavonoid drug potentially for the treatment of HCV infection. has antioxidant and chelating effects in the liver. Naringenin significantly suppressed UVB-induced extracellular signal-regulated kinase 2 (ERK2) activity and subsequently attenuated UVB-induced phosphorylation of p90(RSK) by competitively binding with ATP. Naringenin exerts potent anti-photoaging effects by suppressing ERK2 activity and decreasing FRA1 stability, followed by down-regulation of AP-1 transactivation and MMP-1 expression. Naringenin blocks TGF-β1 trafficking from the trans-Golgi network by suppressing PKC activity, resulting in a reduction of TGF-β1 secretion from breast cancer cells.

Chemical Structure

Naringenin

CAS#480-41-1

Theoretical Analysis

MedKoo Cat#: 527706

Name: Naringenin

CAS#: 480-41-1

Chemical Formula: C15H12O5

Exact Mass: 272.0685

Molecular Weight: 272.26

Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
2g	USD 550.00	2 Weeks
5g	USD 850.00	2 Weeks

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Related CAS #

67604-48-2 480-41-1

Synonym

Naringenin; NSC 11855; NSC-11855; NSC11855

IUPAC/Chemical Name

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

InChi Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

InChi Code

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/t13-/m0/s1

SMILES Code

O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=CC(O)=C13

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C21B09B07

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Naringenin is a bioflavonoid drug potentially for the treatment of HCV infection.

In vitro activity:

Here this study demonstrated that a natural compound, naringenin (NAR), promoted myogenic differentiation of porcine satellite cells (PSCs) in vitro and increased the content and maturity of generated myotubes, especially for PSCs that had undergone extensive expansion. Mechanistically, NAR upregulated the IGF-1/AKT/mTOR anabolic pathway during the myogenesis of PSCs by activating the estrogen receptor β. Reference: Foods. 2022 Nov 22;11(23):3755. https://pubmed.ncbi.nlm.nih.gov/36496566/

In vivo activity:

Intragastrically administered NG (naringenin) (50 mg/kg) induced a significant decrease in plasma GLU in normoglycaemic and NIDDM rat models (p < 0.05) following acute and subchronic time periods. After 5 days of administration, NG produced significant diminished blood GLU and TG levels in streptozotocin-nicotinamide-induced diabetic rats. The administration of NG to normal rats significantly increased the levels of TG, CHOL and HDL (p < 0.05). Reference: Diabetes Obes Metab. 2008 Nov;10(11):1097-104. https://pubmed.ncbi.nlm.nih.gov/18355329/

	Solvent	mg/mL	mM
Solubility
	DMSO	54.0	198.34
	Ethanol	5.0	18.37

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 272.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Yan Q, Fei Z, Li M, Zhou J, Du G, Guan X. Naringenin Promotes Myotube Formation and Maturation for Cultured Meat Production. Foods. 2022 Nov 22;11(23):3755. doi: 10.3390/foods11233755. PMID: 36496566; PMCID: PMC9738036. 2. Zhang X, Li M, Wu H, Fan W, Zhang J, Su W, Wang Y, Li P. Naringenin attenuates inflammation, apoptosis, and ferroptosis in silver nanoparticle-induced lung injury through a mechanism associated with Nrf2/HO-1 axis: In vitro and in vivo studies. Life Sci. 2022 Dec 15;311(Pt A):121127. doi: 10.1016/j.lfs.2022.121127. Epub 2022 Oct 25. PMID: 36306867. 3. Elhemiely AA, Yahia R, Gad AM. Naringenin alleviate reproductive toxicity evoked by lead acetate via attenuation of sperm profile and biochemical alterations in male Wistar rat: Involvement of TGFβ/AKT/mTOR pathway. J Biochem Mol Toxicol. 2023 Feb 20:e23335. doi: 10.1002/jbt.23335. Epub ahead of print. PMID: 36807407. 4. Ortiz-Andrade RR, Sánchez-Salgado JC, Navarrete-Vázquez G, Webster SP, Binnie M, García-Jiménez S, León-Rivera I, Cigarroa-Vázquez P, Villalobos-Molina R, Estrada-Soto S. Antidiabetic and toxicological evaluations of naringenin in normoglycaemic and NIDDM rat models and its implications on extra-pancreatic glucose regulation. Diabetes Obes Metab. 2008 Nov;10(11):1097-104. doi: 10.1111/j.1463-1326.2008.00869.x. Epub 2008 Mar 18. PMID: 18355329.

In vitro protocol:

In vivo protocol:

1. Elhemiely AA, Yahia R, Gad AM. Naringenin alleviate reproductive toxicity evoked by lead acetate via attenuation of sperm profile and biochemical alterations in male Wistar rat: Involvement of TGFβ/AKT/mTOR pathway. J Biochem Mol Toxicol. 2023 Feb 20:e23335. doi: 10.1002/jbt.23335. Epub ahead of print. PMID: 36807407. 2. Ortiz-Andrade RR, Sánchez-Salgado JC, Navarrete-Vázquez G, Webster SP, Binnie M, García-Jiménez S, León-Rivera I, Cigarroa-Vázquez P, Villalobos-Molina R, Estrada-Soto S. Antidiabetic and toxicological evaluations of naringenin in normoglycaemic and NIDDM rat models and its implications on extra-pancreatic glucose regulation. Diabetes Obes Metab. 2008 Nov;10(11):1097-104. doi: 10.1111/j.1463-1326.2008.00869.x. Epub 2008 Mar 18. PMID: 18355329.

1: Tang JY, Jin P, He Q, Lu LH, Ma JP, Gao WL, Bai HP, Yang J. Naringenin ameliorates hypoxia/reoxygenation-induced endoplasmic reticulum stress-mediated apoptosis in H9c2 myocardial cells: involvement in ATF6, IRE1α and PERK signaling activation. Mol Cell Biochem. 2017 Jan;424(1-2):111-122. doi: 10.1007/s11010-016-2848-1. PubMed PMID: 27785700. 2: Ozkaya A, Sahin Z, Dag U, Ozkaraca M. Effects of Naringenin on Oxidative Stress and Histopathological Changes in the Liver of Lead Acetate Administered Rats. J Biochem Mol Toxicol. 2016 May;30(5):243-8. doi: 10.1002/jbt.21785. PubMed PMID: 26929248. 3: Jung SK, Ha SJ, Jung CH, Kim YT, Lee HK, Kim MO, Lee MH, Mottamal M, Bode AM, Lee KW, Dong Z. Naringenin targets ERK2 and suppresses UVB-induced photoaging. J Cell Mol Med. 2016 May;20(5):909-19. doi: 10.1111/jcmm.12780. PubMed PMID: 26861188; PubMed Central PMCID: PMC4831363. 4: Chattopadhyay D, Sen S, Chatterjee R, Roy D, James J, Thirumurugan K. Context- and dose-dependent modulatory effects of naringenin on survival and development of Drosophila melanogaster. Biogerontology. 2016 Apr;17(2):383-93. doi: 10.1007/s10522-015-9624-6. PubMed PMID: 26520643. 5: Zhang F, Dong W, Zeng W, Zhang L, Zhang C, Qiu Y, Wang L, Yin X, Zhang C, Liang W. Naringenin prevents TGF-β1 secretion from breast cancer and suppresses pulmonary metastasis by inhibiting PKC activation. Breast Cancer Res. 2016 Apr 1;18(1):38. doi: 10.1186/s13058-016-0698-0. PubMed PMID: 27036297; PubMed Central PMCID: PMC4818388. 6: Wu LH, Lin C, Lin HY, Liu YS, Wu CY, Tsai CF, Chang PC, Yeh WL, Lu DY. Naringenin Suppresses Neuroinflammatory Responses Through Inducing Suppressor of Cytokine Signaling 3 Expression. Mol Neurobiol. 2016 Mar;53(2):1080-91. doi: 10.1007/s12035-014-9042-9. PubMed PMID: 25579382. 7: Ren B, Qin W, Wu F, Wang S, Pan C, Wang L, Zeng B, Ma S, Liang J. Apigenin and naringenin regulate glucose and lipid metabolism, and ameliorate vascular dysfunction in type 2 diabetic rats. Eur J Pharmacol. 2016 Feb 15;773:13-23. doi: 10.1016/j.ejphar.2016.01.002. PubMed PMID: 26801071. 8: Ke JY, Cole RM, Hamad EM, Hsiao YH, Cotten BM, Powell KA, Belury MA. Citrus flavonoid, naringenin, increases locomotor activity and reduces diacylglycerol accumulation in skeletal muscle of obese ovariectomized mice. Mol Nutr Food Res. 2016 Feb;60(2):313-24. doi: 10.1002/mnfr.201500379. PubMed PMID: 26573879; PubMed Central PMCID: PMC4789085. 9: Hashimoto T, Ide T. Activity and mRNA Levels of Enzymes Involved in Hepatic Fatty Acid Synthesis in Rats Fed Naringenin. J Agric Food Chem. 2015 Nov 4;63(43):9536-42. doi: 10.1021/acs.jafc.5b03734. PubMed PMID: 26466635. 10: Roy S, Ahmed F, Banerjee S, Saha U. Naringenin ameliorates streptozotocin-induced diabetic rat renal impairment by downregulation of TGF-β1 and IL-1 via modulation of oxidative stress correlates with decreased apoptotic events. Pharm Biol. 2016 Sep;54(9):1616-27. doi: 10.3109/13880209.2015.1110599. PubMed PMID: 26928632. 11: Orrego-Lagarón N, Martínez-Huélamo M, Vallverdú-Queralt A, Lamuela-Raventos RM, Escribano-Ferrer E. High gastrointestinal permeability and local metabolism of naringenin: influence of antibiotic treatment on absorption and metabolism. Br J Nutr. 2015 Jul;114(2):169-80. doi: 10.1017/S0007114515001671. PubMed PMID: 26083965. 12: Manchope MF, Calixto-Campos C, Coelho-Silva L, Zarpelon AC, Pinho-Ribeiro FA, Georgetti SR, Baracat MM, Casagrande R, Verri WA Jr. Naringenin Inhibits Superoxide Anion-Induced Inflammatory Pain: Role of Oxidative Stress, Cytokines, Nrf-2 and the NO-cGMP-PKG-KATP Channel Signaling Pathway. PLoS One. 2016 Apr 5;11(4):e0153015. doi: 10.1371/journal.pone.0153015. PubMed PMID: 27045367; PubMed Central PMCID: PMC4821586. 13: Kumar S, Tiku AB. Biochemical and Molecular Mechanisms of Radioprotective Effects of Naringenin, a Phytochemical from Citrus Fruits. J Agric Food Chem. 2016 Mar 2;64(8):1676-85. doi: 10.1021/acs.jafc.5b05067. PubMed PMID: 26881453. 14: Fouad AA, Albuali WH, Jresat I. Protective Effect of Naringenin against Lipopolysaccharide-Induced Acute Lung Injury in Rats. Pharmacology. 2016;97(5-6):224-32. doi: 10.1159/000444262. PubMed PMID: 26872264. 15: Demirdag R, Comakli V, Ozkaya A, Sahin Z, Dag U, Yerlikaya E, Kuzu M. Examination of changes in enzyme activities of erythrocyte glucose 6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase in rats given Naringenin and Lead acetate. J Biochem Mol Toxicol. 2015 Jan;29(1):43-7. doi: 10.1002/jbt.21606. PubMed PMID: 25228019. 16: Park HJ, Choi YJ, Lee JH, Nam MJ. Naringenin causes ASK1-induced apoptosis via reactive oxygen species in human pancreatic cancer cells. Food Chem Toxicol. 2017 Jan;99:1-8. doi: 10.1016/j.fct.2016.11.008. PubMed PMID: 27838343. 17: Shi D, Xu Y, Du X, Chen X, Zhang X, Lou J, Li M, Zhuo J. Co-treatment of THP-1 cells with naringenin and curcumin induces cell cycle arrest and apoptosis via numerous pathways. Mol Med Rep. 2015 Dec;12(6):8223-8. doi: 10.3892/mmr.2015.4480. PubMed PMID: 26496980. 18: Li YR, Chen DY, Chu CL, Li S, Chen YK, Wu CL, Lin CC. Naringenin inhibits dendritic cell maturation and has therapeutic effects in a murine model of collagen-induced arthritis. J Nutr Biochem. 2015 Dec;26(12):1467-78. doi: 10.1016/j.jnutbio.2015.07.016. PubMed PMID: 26350255. 19: Yoshida H, Tsuhako R, Atsumi T, Narumi K, Watanabe W, Sugita C, Kurokawa M. Naringenin interferes with the anti-diabetic actions of pioglitazone via pharmacodynamic interactions. J Nat Med. 2016 Dec 3. [Epub ahead of print] PubMed PMID: 27915399. 20: Álvarez-Álvarez R, Botas A, Albillos SM, Rumbero A, Martín JF, Liras P. Molecular genetics of naringenin biosynthesis, a typical plant secondary metabolite produced by Streptomyces clavuligerus. Microb Cell Fact. 2015 Nov 9;14:178. doi: 10.1186/s12934-015-0373-7. PubMed PMID: 26553209; PubMed Central PMCID: PMC4640377.

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