Naringin dihydrochalcone | CAS# 18916-17-1 | Flavonoid

MedKoo Cat#: 574020 | Name: Naringin dihydrochalcone

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Description:

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

Naringin dihydrochalcone is an artificial sweetener and flavonoid that has antioxidant activity. It scavenges ABTS, oxygen, and 2,2-diphenyl-1-picrylhydrazyl (DPPH).

Chemical Structure

Naringin dihydrochalcone

CAS#18916-17-1

Theoretical Analysis

MedKoo Cat#: 574020

Name: Naringin dihydrochalcone

CAS#: 18916-17-1

Chemical Formula: C27H34O14

Exact Mass: 582.1949

Molecular Weight: 582.56

Elemental Analysis: C, 55.67; H, 5.88; O, 38.45

Price and Availability

Size	Price	Availability
5g	USD 250.00	2 Weeks
10g	USD 350.00	2 Weeks
25g	USD 550.00	2 Weeks

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Synonym

Naringin dihydrochalcone; Naringin DC;

IUPAC/Chemical Name

1-(4-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

InChi Key

CWBZAESOUBENAP-QVNVHUMTSA-N

InChi Code

InChI=1S/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

SMILES Code

OC1=C(C(CCC2=CC=C(O)C=C2)=O)C(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@]4([H])[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)=C1

Appearance

Solid powder

Purity

>97% (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

>3 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

Instruction

View handling instruction

Biological target:

Naringin Dihydrochalcone is an artificial sweetener derived from naringin.

In vitro activity:

This study investigated the inhibitory effect of Naringin on human AGS cancer cells. AGS cell proliferation was inhibited by Naringin in a dose- and time-dependent manner. Growth inhibitory role of Naringin was observed by western blot analysis demonstrating downregulation of PI3K/Akt/mTOR cascade with an upregulated p21CIPI/WAFI. Formation of cytoplasmic vacuoles and autophagosomes were observed in Naringin-treated AGS cells, further confirmed by the activation of autophagic proteins Beclin 1 and LC3B with a significant phosphorylation of mitogen activated protein kinases (MAPKs). Collectively, these observed results determined that anti-proliferative activity of Naringin in AGS cancer cells is due to suppression of PI3K/Akt/mTOR cascade via induction of autophagy with activated MAPKs. Reference: Int J Oncol. 2015 Sep;47(3):1061-9. https://pubmed.ncbi.nlm.nih.gov/26201693/

In vivo activity:

These results showed that oral administration of naringin significantly improved the learning and memory abilities as evidenced by increasing recognition index by 52.5% in the novel object recognition test and inducing a 1.05-fold increase in the crossing-target number in the probe test, and ameliorated mitochondrial dysfunction in mice caused by HFD consumption. Moreover, naringin significantly enhanced insulin signaling pathway as indicated by a 34.5% increase in the expression levels of IRS-1, a 47.8% decrease in the p-IRS-1, a 1.43-fold increase in the p-Akt, and a 1.89-fold increase in the p-GSK-3β in the hippocampus of the HFDN mice versus HFD mice. Reference: Cell Mol Neurobiol. 2015 Oct;35(7):1061-71. https://pubmed.ncbi.nlm.nih.gov/25939427/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	51.50
	DMSO	76.7	131.60
	Ethanol	65.0	111.58

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 582.56 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. Kulasekaran G, Ganapasam S. Neuroprotective efficacy of naringin on 3-nitropropionic acid-induced mitochondrial dysfunction through the modulation of Nrf2 signaling pathway in PC12 cells. Mol Cell Biochem. 2015 Nov;409(1-2):199-211. doi: 10.1007/s11010-015-2525-9. Epub 2015 Aug 18. PMID: 26280522. 2. Raha S, Yumnam S, Hong GE, Lee HJ, Saralamma VV, Park HS, Heo JD, Lee SJ, Kim EH, Kim JA, Kim GS. Naringin induces autophagy-mediated growth inhibition by downregulating the PI3K/Akt/mTOR cascade via activation of MAPK pathways in AGS cancer cells. Int J Oncol. 2015 Sep;47(3):1061-9. doi: 10.3892/ijo.2015.3095. Epub 2015 Jul 20. PMID: 26201693. 3. Wei Y, Sun L, Liu C, Li L. Naringin regulates endoplasmic reticulum stress and mitophagy through the ATF3/PINK1 signaling axis to alleviate pulmonary fibrosis. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 23. doi: 10.1007/s00210-023-02390-z. Epub ahead of print. PMID: 36688958. 4. Wang D, Yan J, Chen J, Wu W, Zhu X, Wang Y. Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice. Cell Mol Neurobiol. 2015 Oct;35(7):1061-71. doi: 10.1007/s10571-015-0201-y. Epub 2015 May 5. PMID: 25939427.

In vitro protocol:

In vivo protocol:

1. Wei Y, Sun L, Liu C, Li L. Naringin regulates endoplasmic reticulum stress and mitophagy through the ATF3/PINK1 signaling axis to alleviate pulmonary fibrosis. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 23. doi: 10.1007/s00210-023-02390-z. Epub ahead of print. PMID: 36688958. 2. Wang D, Yan J, Chen J, Wu W, Zhu X, Wang Y. Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice. Cell Mol Neurobiol. 2015 Oct;35(7):1061-71. doi: 10.1007/s10571-015-0201-y. Epub 2015 May 5. PMID: 25939427.

1. Gentili, B., and Horowtiz, R.M. Chromatography of dihydrochalcone sweeteners and related compounds: A reagent for detecting dihydrochalcones. J. Chromatogr. 63(5730), 467-469 (1971). 2. Li, X., Chen, B., Xie, H., et al. Antioxidant structure-activity relationship analysis of five dihydrochalcones. Molecules 23(5), E1162 (2018).