Phloretin | NSC 407292 | RJC 02792 | CAS#60-82-2 | MCT1/MCT2 inhibitor

MedKoo Cat#: 326802 | Name: Phloretin

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Description:

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

Phloretin, also known as NSC 407292 and RJC 02792, is a dihydrochalcone flavonoid, is mainly found in fruit, leaves, and roots of apple tree. Phloretin inhibits a variety of transporters. Phloretin inhibits the monocarboxylate transporters MCT1 and MCT2 (IC50 = 28 and 14 µM, respectively). Phloretin exerts antioxidant, anti-inflammatory, and anti-tumor activities in mammalian cells).

Chemical Structure

Phloretin

CAS#60-82-2

Theoretical Analysis

MedKoo Cat#: 326802

Name: Phloretin

CAS#: 60-82-2

Chemical Formula: C15H14O5

Exact Mass: 274.0841

Molecular Weight: 274.27

Elemental Analysis: C, 65.69; H, 5.15; O, 29.17

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 150.00
500mg	USD 250.00
1g	USD 450.00

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Synonym

NSC 407292; NSC-407292; NSC407292; RJC 02792; RJC02792; RJC-02792; Phloretin

IUPAC/Chemical Name

3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone

InChi Key

VGEREEWJJVICBM-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2

SMILES Code

O=C(C1=C(O)C=C(O)C=C1O)CCC2=CC=C(O)C=C2

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

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Phloridzin is a specific, competitive and orally active inhibitor of sodium/glucose cotransporters in the intestine (SGLT1) and kidney (SGLT2). Phloretin inhibits Yeast-made GLUT1 as well as Human erythrocyte GLUT1 with IC50values of 49 μM and 61 μM.

In vitro activity:

Phloretin induced obvious cytotoxicity against BEL-7402 cells with IC50 of 89.23 microg/mL. The growth curve demonstrated decreased growth of the cells as phloretin concentration increased. Cell apoptosis occurred 24 h after treatment with 40-160 microg/mL phloretin. Morphological, the cells exposed to phloretin exhibited nuclear chromatin condensation and increased fluorescence intensity. The activity of caspase-9 reached the peak level 12 h after phloretin exposure, and leak levels of caspase-6 and caspase-3 activities occurred 18 and 24 h after the exposure, respectively. Reference: Nan Fang Yi Ke Da Xue Xue Bao. 2008 Jul;28(7):1249-51. https://pubmed.ncbi.nlm.nih.gov/18676276/

In vivo activity:

CIA (collagen-induced arthritis) mice were dosed daily with phloretin at either 50 or 100 mg/kg among two treatment groups. CIA treated mice showed mitigation of clinical symptoms of RA in addition to reduced inflammation of hind-limbs compared to mice who did not receive phloretin. Histological analysis showed that phloretin suppressed the severity of RA and effectively mitigated joint inflammation and cartilage- and bone-destruction via reducing proinflammatory cytokine productions (TNF-α, IL-6, IL-1β, and IL-17). Moreover, phloretin-treated CIA mice showed decreased oxidative stress and diminished levels of malondialdehyde (MDA) and hydrogen peroxide (H2O2) in paw tissues as well as reduced productivity of anti-collagen antibodies in serum. Reference: Evid Based Complement Alternat Med. 2016;2016:9831263. https://pubmed.ncbi.nlm.nih.gov/28044086/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	109.38
	DMSO	45.0	164.07
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.82
	Ethanol	32.5	118.50

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 274.27 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. Huang WC, Chang WT, Wu SJ, Xu PY, Ting NC, Liou CJ. Phloretin and phlorizin promote lipolysis and inhibit inflammation in mouse 3T3-L1 cells and in macrophage-adipocyte co-cultures. Mol Nutr Food Res. 2013 Oct;57(10):1803-13. doi: 10.1002/mnfr.201300001. Epub 2013 Jun 17. PMID: 23776070. 2. Luo H, Wang YJ, Chen J, Liu JQ, Zhang HT. [Phloretin induces apoptosis of BEL-7402 cells in vitro]. Nan Fang Yi Ke Da Xue Xue Bao. 2008 Jul;28(7):1249-51. Chinese. PMID: 18676276. 3. Kumar S, Chhimwal J, Kumar S, Singh R, Patial V, Purohit R, Padwad YS. Phloretin and phlorizin mitigates inflammatory stress and alleviate adipose and hepatic insulin resistance by abrogating PPARγ S273-Cdk5 interaction in type 2 diabetic mice. Life Sci. 2023 Jun 1;322:121668. doi: 10.1016/j.lfs.2023.121668. Epub 2023 Apr 5. PMID: 37023949. 4. Wang SP, Lin SC, Li S, Chao YH, Hwang GY, Lin CC. Potent Antiarthritic Properties of Phloretin in Murine Collagen-Induced Arthritis. Evid Based Complement Alternat Med. 2016;2016:9831263. doi: 10.1155/2016/9831263. Epub 2016 Dec 4. PMID: 28044086; PMCID: PMC5164908.

In vitro protocol:

In vivo protocol:

1. Kumar S, Chhimwal J, Kumar S, Singh R, Patial V, Purohit R, Padwad YS. Phloretin and phlorizin mitigates inflammatory stress and alleviate adipose and hepatic insulin resistance by abrogating PPARγ S273-Cdk5 interaction in type 2 diabetic mice. Life Sci. 2023 Jun 1;322:121668. doi: 10.1016/j.lfs.2023.121668. Epub 2023 Apr 5. PMID: 37023949. 2. Wang SP, Lin SC, Li S, Chao YH, Hwang GY, Lin CC. Potent Antiarthritic Properties of Phloretin in Murine Collagen-Induced Arthritis. Evid Based Complement Alternat Med. 2016;2016:9831263. doi: 10.1155/2016/9831263. Epub 2016 Dec 4. PMID: 28044086; PMCID: PMC5164908.

1: Li Q, Wang S, Wang J, Chen L, Liu W, Li Z, Xu J, Deng Z, Zhou Y. Mechanism of Phloretin Accumulation in Malus hupehensis Grown at High Altitudes: Evidence from Quantitative 4D Proteomics. J Agric Food Chem. 2024 Aug 21. doi: 10.1021/acs.jafc.4c04487. Epub ahead of print. PMID: 39166542. 2: Burns KS, Penner GB, Hogan NS, Mutsvangwa T. Whole-body urea kinetics and functional roles of urea transporters and aquaporins in urea secretion into the rumen in sheep fed diets varying in crude protein content and corn grain processing method. J Anim Sci. 2024 Aug 18:skae237. doi: 10.1093/jas/skae237. Epub ahead of print. PMID: 39154206. 3: Liang P, Zhu M, Sun X, Wang L, Li B, Ming S, Younis M, Yang J, Wu Y, Huang X. LncRNA-mRNA co-expression analysis reveals aquaporin-9-promoted neutrophil extracellular trap formation and inflammatory activation in sepsis. Int Immunopharmacol. 2024 Aug 11;140:112916. doi: 10.1016/j.intimp.2024.112916. Epub ahead of print. PMID: 39133961. 4: Lu Z, Yao G, Xie H, Wang D, Chen Y, Zhu W. Pharmaceutical Properties of the Phloretin-4,4'-Bipyridine Cocrystal: Structure Analysis, Drug Release Profile, and Antioxidant Activity Research. ACS Omega. 2024 Jul 8;9(29):31477-31487. doi: 10.1021/acsomega.4c01136. PMID: 39072064; PMCID: PMC11270679. 5: Đorđić M, Janošević D, Smailagić D, Banjac N, Ninković S, Stanišić M, Trajković M. Effects of Phloretin on Seedling Growth and Histochemical Distribution of Phenols, Polysaccharides and Lipids in Capsella bursa- pastoris (L.) Medik. Plants (Basel). 2024 Jul 9;13(14):1890. doi: 10.3390/plants13141890. PMID: 39065417; PMCID: PMC11280091. 6: Wu D, Hao L, Liu X, Li X, Zhao G. The Anti-Biofilm Properties of Phloretin and Its Analogs against Porphyromonas gingivalis and Its Complex Flora. Foods. 2024 Jun 24;13(13):1994. doi: 10.3390/foods13131994. PMID: 38998500; PMCID: PMC11241327. 7: Yamamoto S, Yamamoto S, Takahashi M, Mii A, Okubo A, Toriu N, Nakagawa S, Abe T, Fukuma S, Imamura H, Yamamoto M, Yanagita M. Visualization of intracellular ATP dynamics in different nephron segments under pathophysiological conditions using the kidney slice culture system. Kidney Int. 2024 Sep;106(3):470-481. doi: 10.1016/j.kint.2024.05.028. Epub 2024 Jul 9. PMID: 38996810. 8: Wang H, Jian L, Wang Z, Jiao Y, Wang Y, Ma F, Li P. Glycosylation mode of phloretin affects the morphology and stress resistance of apple plant. Plant Cell Environ. 2024 Jul 12. doi: 10.1111/pce.15031. Epub ahead of print. PMID: 38995178. 9: Mansoor R, Hasan Z, Zaidan Y. ANTICANCER ACTIVITY OF PHLORETIN COMPOUND PURIFIED FROM IRAQI MALUS DOMESTICA L. (APPLE) LEAVES. Georgian Med News. 2024 Apr;(349):126-136. PMID: 38963216. 10: Fuentes-Jorquera N, Canales RI, Pérez-Correa JR, Pérez-Jiménez J, Mariotti- Celis MS. Differential Extraction and Preliminary Identification of Polyphenols from Ugni candollei (White Murta) Berries. Antioxidants (Basel). 2024 May 21;13(6):623. doi: 10.3390/antiox13060623. PMID: 38929063; PMCID: PMC11200422. 11: Piras A, Porcedda S, Smeriglio A, Trombetta D, Nieddu M, Piras F, Sogos V, Rosa A. Chemical Composition, Nutritional, and Biological Properties of Extracts Obtained with Different Techniques from Aronia melanocarpa Berries. Molecules. 2024 May 30;29(11):2577. doi: 10.3390/molecules29112577. PMID: 38893452; PMCID: PMC11173777. 12: Ruel Y, Moawad F, Alsarraf J, Pichette A, Legault J, Brambilla D, Pouliot R. Antiproliferative and Anti-Inflammatory Effects of the Polyphenols Phloretin and Balsacone C in a Coculture of T Cells and Psoriatic Keratinocytes. Int J Mol Sci. 2024 May 22;25(11):5639. doi: 10.3390/ijms25115639. PMID: 38891824; PMCID: PMC11171971. 13: Zhou T, Xing Q, Bu J, Han W, Shen Z. Integrated metabolomic and transcriptomic analysis reveals the regulatory mechanisms of flavonoid and alkaloid biosynthesis in the new and old leaves of Murraya tetramera Huang. BMC Plant Biol. 2024 Jun 5;24(1):499. doi: 10.1186/s12870-024-05066-9. PMID: 38840069; PMCID: PMC11151518. 14: Ferreira AF, Machado-Simões J, Moniz I, Soares M, Carvalho A, Diniz P, Ramalho-Santos J, Sousa AP, Lopes-da-Costa L, Almeida-Santos T. Chemical reversion of age-related oocyte dysfunction fails to enhance embryo development in a bovine model of postovulatory aging. J Assist Reprod Genet. 2024 Aug;41(8):1997-2009. doi: 10.1007/s10815-024-03151-4. Epub 2024 Jun 1. PMID: 38822989; PMCID: PMC11339206. 15: Duan Y, Li H, Huang S, Li Y, Chen S, Xie L. Phloretin inhibits transmissible gastroenteritis virus proliferation via multiple mechanisms. J Gen Virol. 2024 May;105(5). doi: 10.1099/jgv.0.001996. PMID: 38814698. 16: Efimova SS, Ostroumova OS. Antibiotic Loaded Phytosomes as a Way to Develop Innovative Lipid Formulations of Polyene Macrolides. Pharmaceutics. 2024 May 16;16(5):665. doi: 10.3390/pharmaceutics16050665. PMID: 38794328; PMCID: PMC11124810. 17: Kassym L, Kussainova A, Semenova Y, McLoone P. Antimicrobial Effect of Honey Phenolic Compounds against E. coli-An In Vitro Study. Pharmaceuticals (Basel). 2024 Apr 27;17(5):560. doi: 10.3390/ph17050560. PMID: 38794130; PMCID: PMC11123796. 18: Goris T, Braune A. Genomics and physiology of Catenibacillus, human gut bacteria capable of polyphenol C-deglycosylation and flavonoid degradation. Microb Genom. 2024 May;10(5):001245. doi: 10.1099/mgen.0.001245. PMID: 38785231; PMCID: PMC11170127. 19: Zhang W, Sun Y, Wang H, Xu M, He C, Wang C, Yu Y, Zhang Z, Su L. Exogenous Melatonin Enhances Dihydrochalcone Accumulation in Lithocarpus litseifolius Leaves via Regulating Hormonal Crosstalk and Transcriptional Profiling. Int J Mol Sci. 2024 Apr 23;25(9):4592. doi: 10.3390/ijms25094592. PMID: 38731810; PMCID: PMC11083347. 20: Zhang Y, Wu Y, Li B, Tian J. Phloretin prolongs lifespan of Caenorhabditis elegans via inhibition of NDUFS1 and NDUFS6 at mitochondrial complex Ⅰ. Free Radic Biol Med. 2024 Aug 20;221:283-295. doi: 10.1016/j.freeradbiomed.2024.05.005. Epub 2024 May 3. PMID: 38705496.