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MedKoo Cat#: 464510 | Name: Naringenin Chalcone
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Description:

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

Naringenin chalcone is a flavonoid that has been found in the skin of red tomatoes and has diverse biological activities. It inhibits the proliferation of SENCAR mouse skin transformed (SST) cells and SENCAR mouse skin transformed tumor (SST-T) cells (IC50s = 92 and 184 µg/ml). Naringenin chalcone (50 µg/animal) reduces the number of papillomas in a mouse model of skin carcinogenesis induced by phorbol 12-myristate 13-acetate (TPA). Topical administration of naringenin chalcone reduces ear edema in a mouse model of TPA-induced inflammation. Naringenin chalcone (0.8 mg/kg) reduces airway hyperresponsiveness, bronchoalveolar lavage fluid (BALF) eosinophil infiltration, and lung mucus production in a mouse model of ovalbumin-induced allergic asthma.

Chemical Structure

Naringenin Chalcone
Naringenin Chalcone
CAS#73692-50-9

Theoretical Analysis

MedKoo Cat#: 464510

Name: Naringenin Chalcone

CAS#: 73692-50-9

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 Quantity
1mg USD 550.00 2 Weeks
5mg USD 1,250.00 2 Weeks
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Related CAS #
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Synonym
Naringenin Chalcone; 2',4,4',6'-Tetrahydroxychalcone; 2',4,4',6' Tetrahydroxychalcone;
IUPAC/Chemical Name
(E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
InChi Key
YQHMWTPYORBCMF-ZZXKWVIFSA-N
InChi Code
InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H/b6-3+
SMILES Code
O=C(/C=C/C1=CC=C(O)C=C1)C2=C(C=C(C=C2O)O)O
Appearance
Solid powder
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
Naringenin chalcone is an intermediate in flavonol biosynthesis and is spontaneously metabolized into naringenin (NAR) by chalcone isomerase.
In vitro activity:
Naringenin chalcone inhibited the production of TNF-alpha, MCP-1, and nitric oxide (NO) by LPS-stimulated RAW 264 macrophages in a dose-dependent manner. Coculture of 3T3-L1 adipocytes and RAW 264 macrophages markedly enhanced the production of TNF-alpha, MCP-1, and NO compared with the control cultures; however, treatment with naringenin chalcone dose-dependently inhibited the production of these proinflammatory mediators. Reference: Life Sci. 2007 Sep 29;81(16):1272-9. https://pubmed.ncbi.nlm.nih.gov/17915259/
In vivo activity:
Naringenin chalcone inhibited the production of TNF-alpha, MCP-1, and nitric oxide (NO) by LPS-stimulated RAW 264 macrophages in a dose-dependent manner. Coculture of 3T3-L1 adipocytes and RAW 264 macrophages markedly enhanced the production of TNF-alpha, MCP-1, and NO compared with the control cultures; however, treatment with naringenin chalcone dose-dependently inhibited the production of these proinflammatory mediators. Reference: Life Sci. 2007 Sep 29;81(16):1272-9. https://pubmed.ncbi.nlm.nih.gov/17915259/
Solvent mg/mL mM
Solubility
DMF 15.0 55.00
DMSO 10.0 36.00
Ethanol 1.0 3.60
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.

Recalculate based on batch purity %
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. Horiba T, Nishimura I, Nakai Y, Abe K, Sato R. Naringenin chalcone improves adipocyte functions by enhancing adiponectin production. Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14. doi: 10.1016/j.mce.2010.03.020. Epub 2010 Apr 2. PMID: 20363289. 2. Hirai S, Kim YI, Goto T, Kang MS, Yoshimura M, Obata A, Yu R, Kawada T. Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages. Life Sci. 2007 Sep 29;81(16):1272-9. doi: 10.1016/j.lfs.2007.09.001. Epub 2007 Sep 12. PMID: 17915259. 3. Escribano-Ferrer E, Queralt Regué J, Garcia-Sala X, Boix Montañés A, Lamuela-Raventos RM. In Vivo Anti-inflammatory and Antiallergic Activity of Pure Naringenin, Naringenin Chalcone, and Quercetin in Mice. J Nat Prod. 2019 Feb 22;82(2):177-182. doi: 10.1021/acs.jnatprod.8b00366. Epub 2019 Jan 28. PMID: 30688453. 4. Iwamura C, Shinoda K, Yoshimura M, Watanabe Y, Obata A, Nakayama T. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol Int. 2010 Mar;59(1):67-73. doi: 10.2332/allergolint.09-OA-0118. Epub 2009 Dec 25. PMID: 20035147.
In vitro protocol:
1. Horiba T, Nishimura I, Nakai Y, Abe K, Sato R. Naringenin chalcone improves adipocyte functions by enhancing adiponectin production. Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14. doi: 10.1016/j.mce.2010.03.020. Epub 2010 Apr 2. PMID: 20363289. 2. Hirai S, Kim YI, Goto T, Kang MS, Yoshimura M, Obata A, Yu R, Kawada T. Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages. Life Sci. 2007 Sep 29;81(16):1272-9. doi: 10.1016/j.lfs.2007.09.001. Epub 2007 Sep 12. PMID: 17915259.
In vivo protocol:
1. Escribano-Ferrer E, Queralt Regué J, Garcia-Sala X, Boix Montañés A, Lamuela-Raventos RM. In Vivo Anti-inflammatory and Antiallergic Activity of Pure Naringenin, Naringenin Chalcone, and Quercetin in Mice. J Nat Prod. 2019 Feb 22;82(2):177-182. doi: 10.1021/acs.jnatprod.8b00366. Epub 2019 Jan 28. PMID: 30688453. 2. Iwamura C, Shinoda K, Yoshimura M, Watanabe Y, Obata A, Nakayama T. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol Int. 2010 Mar;59(1):67-73. doi: 10.2332/allergolint.09-OA-0118. Epub 2009 Dec 25. PMID: 20035147.
1: Kong D, Li S, Smolke CD. Discovery of a previously unknown biosynthetic capacity of naringenin chalcone synthase by heterologous expression of a tomato gene cluster in yeast. Sci Adv. 2020 Oct 30;6(44):eabd1143. doi: 10.1126/sciadv.abd1143. PMID: 33127687; PMCID: PMC7608815. 2: Liu Y, Liu J, Wang R, Sun H, Li M, Strappe P, Zhou Z. Analysis of secondary metabolites induced by yellowing process for understanding rice yellowing mechanism. Food Chem. 2021 Apr 16;342:128204. doi: 10.1016/j.foodchem.2020.128204. Epub 2020 Sep 28. PMID: 33097330. 3: Zhou Z, Gao H, Ming J, Ding Z, Lin X, Zhan R. Combined Transcriptome and Metabolome analysis of Pitaya fruit unveiled the mechanisms underlying Peel and pulp color formation. BMC Genomics. 2020 Oct 22;21(1):734. doi: 10.1186/s12864-020-07133-5. PMID: 33092530; PMCID: PMC7579827. 4: Ayuso-Calles M, García-Estévez I, Jiménez-Gómez A, Flores-Félix JD, Escribano-Bailón MT, Rivas R. Rhizobium laguerreae Improves Productivity and Phenolic Compound Content of Lettuce (Lactuca sativa L.) under Saline Stress Conditions. Foods. 2020 Aug 24;9(9):1166. doi: 10.3390/foods9091166. PMID: 32847018; PMCID: PMC7555320. 5: Zhang M, Wang Z, Hao S, Hao L, Zhang X, Yu P, Sun H. Synthesis of natural 3'-Prenylchalconaringenin and biological evaluation of ameliorating non- alcoholic fatty liver disease and metabolic syndrome. Eur J Med Chem. 2020 Nov 1;205:112649. doi: 10.1016/j.ejmech.2020.112649. Epub 2020 Jul 28. PMID: 32791402. 6: Park HL, Yoo Y, Bhoo SH, Lee TH, Lee SW, Cho MH. Two Chalcone Synthase Isozymes Participate Redundantly in UV-Induced Sakuranetin Synthesis in Rice. Int J Mol Sci. 2020 May 27;21(11):3777. doi: 10.3390/ijms21113777. PMID: 32471084; PMCID: PMC7312121. 7: Kausar H, Ambrin G, Okla MK, Soufan W, Al-Ghamdi AA, Ahmad A. Metabolic Flux Analysis of Catechin Biosynthesis Pathways Using Nanosensor. Antioxidants (Basel). 2020 Mar 31;9(4):288. doi: 10.3390/antiox9040288. PMID: 32244268; PMCID: PMC7222200. 8: Gao J, Ren R, Wei Y, Jin J, Ahmad S, Lu C, Wu J, Zheng C, Yang F, Zhu G. Comparative Metabolomic Analysis Reveals Distinct Flavonoid Biosynthesis Regulation for Leaf Color Development of Cymbidium sinense 'Red Sun'. Int J Mol Sci. 2020 Mar 9;21(5):1869. doi: 10.3390/ijms21051869. PMID: 32182912; PMCID: PMC7084835. 9: Abbasi-Parizad P, De Nisi P, Adani F, Pepé Sciarria T, Squillace P, Scarafoni A, Iametti S, Scaglia B. Antioxidant and Anti-Inflammatory Activities of the Crude Extracts of Raw and Fermented Tomato Pomace and Their Correlations with Aglycate-Polyphenols. Antioxidants (Basel). 2020 Feb 21;9(2):179. doi: 10.3390/antiox9020179. PMID: 32098217; PMCID: PMC7070286. 10: Yoo HJ, Kim JH, Park KS, Son JE, Lee JM. Light-Controlled Fruit Pigmentation and Flavor Volatiles in Tomato and Bell Pepper. Antioxidants (Basel). 2019 Dec 23;9(1):14. doi: 10.3390/antiox9010014. PMID: 31877964; PMCID: PMC7023227. 11: Kolot C, Rodriguez-Mateos A, Feliciano R, Bottermann K, Stahl W. Bioavailability of naringenin chalcone in humans after ingestion of cherry tomatoes. Int J Vitam Nutr Res. 2020 Oct;90(5-6):411-416. doi: 10.1024/0300-9831/a000574. Epub 2019 Apr 8. PMID: 30961461. 12: Gurdon C, Poulev A, Armas I, Satorov S, Tsai M, Raskin I. Genetic and Phytochemical Characterization of Lettuce Flavonoid Biosynthesis Mutants. Sci Rep. 2019 Mar 1;9(1):3305. doi: 10.1038/s41598-019-39287-y. PMID: 30824720; PMCID: PMC6397293. 13: Escribano-Ferrer E, Queralt Regué J, Garcia-Sala X, Boix Montañés A, Lamuela-Raventos RM. In Vivo Anti-inflammatory and Antiallergic Activity of Pure Naringenin, Naringenin Chalcone, and Quercetin in Mice. J Nat Prod. 2019 Feb 22;82(2):177-182. doi: 10.1021/acs.jnatprod.8b00366. Epub 2019 Jan 28. PMID: 30688453.