Quercetin Dihydrate | CAS#6151-25-3 | ATPase/phosphodiesterase inhibitor

MedKoo Cat#: 561651 | Name: Quercetin Dihydrate

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Description:

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

Quercetin Dihydrate is a mitochondrial ATPase and phosphodiesterase inhibitor that also inhibits PI3-kinase activity and displays antiproliferative effects on cancer cell lines. It reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in the late G1 phase of the cell cycle.

Chemical Structure

Quercetin Dihydrate

CAS#6151-25-3

Theoretical Analysis

MedKoo Cat#: 561651

Name: Quercetin Dihydrate

CAS#: 6151-25-3

Chemical Formula: C15H14O9

Exact Mass: 338.0638

Molecular Weight: 338.27

Elemental Analysis: C, 53.26; H, 4.17; O, 42.57

Price and Availability

Size	Price	Availability	Quantity
5g	USD 180.00
25g	USD 300.00

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Synonym

Quercetin Dihydrate;

IUPAC/Chemical Name

2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one dihydrate

InChi Key

GMGIWEZSKCNYSW-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H10O7.2H2O/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6;;/h1-5,16-19,21H;2*1H2

SMILES Code

O=C1C(O)=C(C2=CC=C(O)C(O)=C2)OC3=C1C(O)=CC(O)=C3.[H]O[H].[H]O[H]

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 and Ethanol

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:

Quercetin Dihydrate is a mitochondrial ATPase and phosphodiesterase inhibitor that reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in the late G1 phase of the cell cycle.

In vitro activity:

Quercetin dihydrate produced a dose-dependent inhibition of proliferation on mononuclears triggered by T- and B-cell mitogens. Lymphocytes were in vivo pretreated with the examined agents followed by their explantation and in vitro activation with T- and B-cell mitogens in cell culture; modified bioflavonoid demonstrated higher antiproliferative activity. Reference: Bull Exp Biol Med. 2016 Jul;161(3):381-3. https://pubmed.ncbi.nlm.nih.gov/27496028/

In vivo activity:

In mice, quercetin dihydrate significantly reduced cardiac contractile function, fibrosis, inflammation and myocardial hypertrophy induced by Ang II. Quercetin dihydrate could inhibit the expression of Collagen I and Collagen III, which are the markers of fibroblast differentiation. It has an inhibitory effect on the proliferation and differentiation of fibroblasts induced by angiotensin II in vitro. Quercetin dihydrate plays a key role in the progression of myocardial fibrosis and it may be a promising drug for the treatment of myocardial fibrosis. Reference: Biomed Pharmacother. 2020 Jul;127:110205. https://pubmed.ncbi.nlm.nih.gov/32403046/

	Solvent	mg/mL	mM
Solubility
	DMSO	67.0	198.06
	Ethanol	17.0	50.25

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 338.27 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. Albegova DZ, Kamkina OV, Pavlova SI, Albegova ZhK, Laptev OS, Kozlov IG. Antiproliferative Effects of Modified Bioflavonoid in Ex Vivo Model. Bull Exp Biol Med. 2016 Jul;161(3):381-3. doi: 10.1007/s10517-016-3419-x. Epub 2016 Aug 6. PMID: 27496028. 2. Vandegraaff N, Kumar R, Hocking H, Burke TR Jr, Mills J, Rhodes D, Burrell CJ, Li P. Specific inhibition of human immunodeficiency virus type 1 (HIV-1) integration in cell culture: putative inhibitors of HIV-1 integrase. Antimicrob Agents Chemother. 2001 Sep;45(9):2510-6. doi: 10.1128/AAC.45.9.2510-2516.2001. PMID: 11502522; PMCID: PMC90685. 3. Wang L, Tan A, An X, Xia Y, Xie Y. Quercetin Dihydrate inhibition of cardiac fibrosis induced by angiotensin II in vivo and in vitro. Biomed Pharmacother. 2020 Jul;127:110205. doi: 10.1016/j.biopha.2020.110205. Epub 2020 May 8. PMID: 32403046. 4. Apichart V, Wong R, Rabie B, Lei S. The effect of quercetin on expression of SOX9 and subsequent release of type II collagen in spheno-occipital synchondroses of organ-cultured mice. Angle Orthod. 2012 Mar;82(2):247-53. doi: 10.2319/042111-278.1. Epub 2011 Sep 20. PMID: 21932938; PMCID: PMC8867954.

In vitro protocol:

In vivo protocol:

1. Wang L, Tan A, An X, Xia Y, Xie Y. Quercetin Dihydrate inhibition of cardiac fibrosis induced by angiotensin II in vivo and in vitro. Biomed Pharmacother. 2020 Jul;127:110205. doi: 10.1016/j.biopha.2020.110205. Epub 2020 May 8. PMID: 32403046. 2. Apichart V, Wong R, Rabie B, Lei S. The effect of quercetin on expression of SOX9 and subsequent release of type II collagen in spheno-occipital synchondroses of organ-cultured mice. Angle Orthod. 2012 Mar;82(2):247-53. doi: 10.2319/042111-278.1. Epub 2011 Sep 20. PMID: 21932938; PMCID: PMC8867954.

1: Petersen B, Egert S, Bosy-Westphal A, Müller MJ, Wolffram S, Hubbermann EM, Rimbach G, Schwarz K. Bioavailability of quercetin in humans and the influence of food matrix comparing quercetin capsules and different apple sources. Food Res Int. 2016 Oct;88(Pt A):159-165. doi: 10.1016/j.foodres.2016.02.013. Epub 2016 Feb 17. PubMed PMID: 28847395. 2: Avinash B, Venu R, Prasad TNVKV, Alpha Raj M, Srinivasa Rao K, Srilatha C. Synthesis and characterisation of neem leaf extract, 2, 3-dehydrosalanol and quercetin dihydrate mediated silver nano particles for therapeutic applications. IET Nanobiotechnol. 2017 Jun;11(4):383-389. doi: 10.1049/iet-nbt.2016.0095. PubMed PMID: 28530186. 3: Avinash B, Venu R, Alpha Raj M, Srinivasa Rao K, Srilatha C, Prasad TN. In vitro evaluation of acaricidal activity of novel green silver nanoparticles against deltamethrin resistance Rhipicephalus (Boophilus) microplus. Vet Parasitol. 2017 Apr 15;237:130-136. doi: 10.1016/j.vetpar.2017.02.017. Epub 2017 Feb 21. PubMed PMID: 28246003. 4: Trendafilova I, Szegedi A, Mihály J, Momekov G, Lihareva N, Popova M. Preparation of efficient quercetin delivery system on Zn-modified mesoporous SBA-15 silica carrier. Mater Sci Eng C Mater Biol Appl. 2017 Apr 1;73:285-292. doi: 10.1016/j.msec.2016.12.063. Epub 2016 Dec 18. PubMed PMID: 28183610. 5: Sohaib M, Anjum FM, Arshad MS, Imran M, Imran A, Hussain S. Oxidative stability and lipid oxidation flavoring volatiles in antioxidants treated chicken meat patties during storage. Lipids Health Dis. 2017 Feb 1;16(1):27. doi: 10.1186/s12944-017-0426-5. PubMed PMID: 28143531; PubMed Central PMCID: PMC5286778. 6: Albegova DZ, Kamkina OV, Pavlova SI, Albegova ZhK, Laptev OS, Kozlov IG. Antiproliferative Effects of Modified Bioflavonoid in Ex Vivo Model. Bull Exp Biol Med. 2016 Jul;161(3):381-3. doi: 10.1007/s10517-016-3419-x. Epub 2016 Aug 6. PubMed PMID: 27496028. 7: Burak C, Brüll V, Langguth P, Zimmermann BF, Stoffel-Wagner B, Sausen U, Stehle P, Wolffram S, Egert S. Higher plasma quercetin levels following oral administration of an onion skin extract compared with pure quercetin dihydrate in humans. Eur J Nutr. 2017 Feb;56(1):343-353. doi: 10.1007/s00394-015-1084-x. Epub 2015 Oct 20. PubMed PMID: 26482244. 8: Albegova DZ, Kamkina OV, Pavlova SI, Albegova ZhK, Laptev OS, Kozlov IG. Evaluation of the Effect of Modified Bioflavonoid and Quercetin Dihydrate on Cytokine Secretion by Mitogen-Activated Mononuclear Cells. Bull Exp Biol Med. 2015 Sep;159(5):626-8. doi: 10.1007/s10517-015-3031-5. Epub 2015 Oct 15. PubMed PMID: 26468028. 9: Lau AJ, Chang TK. 3-Hydroxyflavone and structural analogues differentially activate pregnane X receptor: Implication for inflammatory bowel disease. Pharmacol Res. 2015 Oct;100:64-72. doi: 10.1016/j.phrs.2015.07.031. Epub 2015 Jul 31. PubMed PMID: 26238175. 10: Cote B, Carlson LJ, Rao DA, Alani AWG. Combinatorial resveratrol and quercetin polymeric micelles mitigate doxorubicin induced cardiotoxicity in vitro and in vivo. J Control Release. 2015 Sep 10;213:128-133. doi: 10.1016/j.jconrel.2015.06.040. Epub 2015 Jul 6. PubMed PMID: 26160305. 11: Stoldt AK, Derno M, Nürnberg G, Weitzel JM, Otten W, Starke A, Wolffram S, Metges CC. Effects of a 6-wk intraduodenal supplementation with quercetin on energy metabolism and indicators of liver damage in periparturient dairy cows. J Dairy Sci. 2015 Jul;98(7):4509-20. doi: 10.3168/jds.2014-9053. Epub 2015 Apr 29. PubMed PMID: 25935242. 12: Shi Y, Williamson G. Comparison of the urinary excretion of quercetin glycosides from red onion and aglycone from dietary supplements in healthy subjects: a randomized, single-blinded, cross-over study. Food Funct. 2015 May;6(5):1443-8. doi: 10.1039/c5fo00155b. PubMed PMID: 25832541. 13: Filip X, Filip C. Can the conformation of flexible hydroxyl groups be constrained by simple NMR crystallography approaches? The case of the quercetin solid forms. Solid State Nucl Magn Reson. 2015 Feb;65:21-8. doi: 10.1016/j.ssnmr.2014.10.006. Epub 2014 Nov 4. PubMed PMID: 25465481. 14: Pimple S, Manjappa AS, Ukawala M, Murthy RS. PLGA nanoparticles loaded with etoposide and quercetin dihydrate individually: in vitro cell line study to ensure advantage of combination therapy. Cancer Nanotechnol. 2012;3(1-6):25-36. Epub 2012 May 9. PubMed PMID: 26069494; PubMed Central PMCID: PMC4451862. 15: Okoko T, Ere D. Hibiscus sabdariffa extractivities on cadmium-mediated alterations of human U937 cell viability and activation. Asian Pac J Trop Med. 2012 Jan;5(1):33-6. doi: 10.1016/S1995-7645(11)60241-1. PubMed PMID: 22182640. 16: Apichart V, Wong R, Rabie B, Lei S. The effect of quercetin on expression of SOX9 and subsequent release of type II collagen in spheno-occipital synchondroses of organ-cultured mice. Angle Orthod. 2012 Mar;82(2):247-53. doi: 10.2319/042111-278.1. Epub 2011 Sep 20. PubMed PMID: 21932938. 17: Ma C, Dastmalchi K, Whitaker BD, Kennelly EJ. Two new antioxidant malonated caffeoylquinic acid isomers in fruits of wild eggplant relatives. J Agric Food Chem. 2011 Sep 14;59(17):9645-51. doi: 10.1021/jf202028y. Epub 2011 Aug 9. PubMed PMID: 21800866. 18: Mendoza-Wilson AM, Santacruz-Ortega H, Balandrán-Quintana RR. Spectroscopic and computational study of the major oxidation products formed during the reaction of two quercetin conformers with a free radical. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Oct 15;81(1):481-8. doi: 10.1016/j.saa.2011.06.041. Epub 2011 Jun 29. PubMed PMID: 21767979. 19: Ahmad A, Khan MM, Hoda MN, Raza SS, Khan MB, Javed H, Ishrat T, Ashafaq M, Ahmad ME, Safhi MM, Islam F. Quercetin protects against oxidative stress associated damages in a rat model of transient focal cerebral ischemia and reperfusion. Neurochem Res. 2011 Aug;36(8):1360-71. doi: 10.1007/s11064-011-0458-6. Epub 2011 Apr 7. PubMed PMID: 21472457. 20: Ganesan S, Faris AN, Comstock AT, Chattoraj SS, Chattoraj A, Burgess JR, Curtis JL, Martinez FJ, Zick S, Hershenson MB, Sajjan US. Quercetin prevents progression of disease in elastase/LPS-exposed mice by negatively regulating MMP expression. Respir Res. 2010 Sep 28;11:131. doi: 10.1186/1465-9921-11-131. PubMed PMID: 20920189; PubMed Central PMCID: PMC2954923.