Isoquercetin | CAS#482-35-9 | Flavonoid

MedKoo Cat#: 530681 | Name: Isoquercetin

Description:

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

Isoquercetin, also known as Isoquercitrin, Quercetin 3-O-glucopyranoside, is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercetin can be isolated from various plant species including Mangifera indica (mango) and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa and Camellia sinensis (tea). Isoquercetin is presently being investigated for prevention of Thromboembolism in selected cancer patients (NCT02195232) and as an anti-fatigue agent in kidney cancer patients treated with sunitinib (NCT02446795).

Chemical Structure

Isoquercetin

CAS#482-35-9 (Isoquercetin)

Theoretical Analysis

MedKoo Cat#: 530681

Name: Isoquercetin

CAS#: 482-35-9 (Isoquercetin)

Chemical Formula: C21H20O12

Exact Mass: 464.0955

Molecular Weight: 464.38

Elemental Analysis: C, 54.32; H, 4.34; O, 41.34

Price and Availability

Size	Price	Availability
1g	USD 450.00	2 Weeks
5g	USD 950.00	2 Weeks
20g	USD 1,650.00	2 Weeks
100g	USD 2,950.00	2 Weeks
1kg	USD 4,850.00	2 Weeks
10kg	USD 14,950.00	2 Weeks

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Related CAS #

482-35-9 (EMIQ) 482-35-9 (Isoquercetin) 17-39-5 (quercetin) 21637-25-2 (Isoquercitrin)

Synonym

Isoquercetin, Quercetin 3-O-glucopyranoside, isoquercitrin; NSC 115918.

IUPAC/Chemical Name

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

InChi Key

OVSQVDMCBVZWGM-QSOFNFLRSA-N

InChi Code

InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1

SMILES Code

OC1=CC(C(OC2=C(C3=O)C(O)=CC(O)=C2)=C3O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)=CC=C1O

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

Other names: Q 5; Quercetin 3-beta-glucoside; Quercetin 3-beta-O-glucoside; Quercetin 3-D-glucoside; Quercetin 3-monoglucoside; Quercetin-3-glucoside; Quercetin-3-O-glucopyranoside; Quercetol 3-glucoside; Quercetol 3-monoglucoside.

Certificate of Analysis

View CoA: current batch, Lot#T24D02P23

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 464.38 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

1: Kim DS, Lim SB. Optimization of Subcritical Water Hydrolysis of Rutin into Isoquercetin and Quercetin. Prev Nutr Food Sci. 2017 Jun;22(2):131-137. doi: 10.3746/pnf.2017.22.2.131. Epub 2017 Jun 30. PubMed PMID: 28702430; PubMed Central PMCID: PMC5503422. 2: Chen M, Dai LH, Fei A, Pan SM, Wang HR. Isoquercetin activates the ERK1/2-Nrf2 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. Exp Ther Med. 2017 Apr;13(4):1353-1359. doi: 10.3892/etm.2017.4093. Epub 2017 Jan 31. PubMed PMID: 28413477; PubMed Central PMCID: PMC5377244. 3: Bhatia N, Kaur G, Soni V, Kataria J, Dhawan RK. Evaluation of the wound healing potential of isoquercetin-based cream on scald burn injury in rats. Burns Trauma. 2016 Mar 16;4:7. doi: 10.1186/s41038-016-0032-1. eCollection 2016. PubMed PMID: 27574677; PubMed Central PMCID: PMC4964293. 4: Kim DY, Yeom SJ, Park CS, Kim YS. Effect of high hydrostatic pressure treatment on isoquercetin production from rutin by commercial α-L-rhamnosidase. Biotechnol Lett. 2016 Oct;38(10):1775-80. doi: 10.1007/s10529-016-2157-5. Epub 2016 Jul 7. PubMed PMID: 27388916. 5: Lu T, Zhang C, Chai M, An Y. Isoquercetin ameliorates tunicamycin-induced apoptosis in rat dorsal root ganglion neurons via suppressing ROS-dependent endoplasmic reticulum stress. Biomed Pharmacother. 2016 May;80:343-51. doi: 10.1016/j.biopha.2016.03.039. Epub 2016 Apr 6. PubMed PMID: 27133075. 6: Yuan M, Shi DZ, Wang TY, Zheng SQ, Liu LJ, Sun ZX, Wang RF, Ding Y. Transformation of trollioside and isoquercetin by human intestinal flora in vitro. Chin J Nat Med. 2016 Mar;14(3):220-6. doi: 10.1016/S1875-5364(16)30019-X. PubMed PMID: 27025369. 7: Cruz-Zúñiga JM, Soto-Valdez H, Peralta E, Mendoza-Wilson AM, Robles-Burgueño MR, Auras R, Gámez-Meza N. Development of an antioxidant biomaterial by promoting the deglycosylation of rutin to isoquercetin and quercetin. Food Chem. 2016 Aug 1;204:420-6. doi: 10.1016/j.foodchem.2016.02.130. Epub 2016 Feb 23. PubMed PMID: 26988520. 8: Wang CP, Shi YW, Tang M, Zhang XC, Gu Y, Liang XM, Wang ZW, Ding F. Isoquercetin Ameliorates Cerebral Impairment in Focal Ischemia Through Anti-Oxidative, Anti-Inflammatory, and Anti-Apoptotic Effects in Primary Culture of Rat Hippocampal Neurons and Hippocampal CA1 Region of Rats. Mol Neurobiol. 2017 Apr;54(3):2126-2142. doi: 10.1007/s12035-016-9806-5. Epub 2016 Feb 29. PubMed PMID: 26924319. 9: Liu D, Mei Q, Wan X, Que H, Li L, Wan D. Determination of rutin and isoquercetin contents in Hibisci mutabilis Folium in different collection periods by HPLC. J Chromatogr Sci. 2015 Nov-Dec;53(10):1680-4. doi: 10.1093/chromsci/bmv071. Epub 2015 Jun 17. PubMed PMID: 26089170. 10: Ran J, Wang Y, Zhang W, Ma M, Zhang H. Research on the bioactivity of isoquercetin extracted from marestail on bladder cancer EJ cell and the mechanism of its occurrence. Artif Cells Nanomed Biotechnol. 2016 May;44(3):859-64. doi: 10.3109/21691401.2014.998823. Epub 2015 Feb 4. PubMed PMID: 25650648. 11: Wang CP, Li JL, Zhang LZ, Zhang XC, Yu S, Liang XM, Ding F, Wang ZW. Isoquercetin protects cortical neurons from oxygen-glucose deprivation-reperfusion induced injury via suppression of TLR4-NF-кB signal pathway. Neurochem Int. 2013 Dec;63(8):741-9. doi: 10.1016/j.neuint.2013.09.018. Epub 2013 Oct 5. PubMed PMID: 24099731. 12: Vongsak B, Sithisarn P, Gritsanapan W. Simultaneous Determination of Crypto-Chlorogenic Acid, Isoquercetin, and Astragalin Contents in Moringa oleifera Leaf Extracts by TLC-Densitometric Method. Evid Based Complement Alternat Med. 2013;2013:917609. doi: 10.1155/2013/917609. Epub 2013 Feb 25. PubMed PMID: 23533530; PubMed Central PMCID: PMC3596951. 13: Zhang R, Yao Y, Wang Y, Ren G. Antidiabetic activity of isoquercetin in diabetic KK -Ay mice. Nutr Metab (Lond). 2011 Dec 2;8:85. doi: 10.1186/1743-7075-8-85. PubMed PMID: 22133267; PubMed Central PMCID: PMC3245443. 14: Vila-Real H, Alfaia AJ, Bronze MR, Calado AR, Ribeiro MH. Enzymatic Synthesis of the Flavone Glucosides, Prunin and Isoquercetin, and the Aglycones, Naringenin and Quercetin, with Selective α-L-Rhamnosidase and β-D-Glucosidase Activities of Naringinase. Enzyme Res. 2011;2011:692618. doi: 10.4061/2011/692618. Epub 2011 Sep 15. PubMed PMID: 21941631; PubMed Central PMCID: PMC3173969. 15: Kim Y, Narayanan S, Chang KO. Inhibition of influenza virus replication by plant-derived isoquercetin. Antiviral Res. 2010 Nov;88(2):227-35. doi: 10.1016/j.antiviral.2010.08.016. Epub 2010 Sep 6. PubMed PMID: 20826184. 16: Li YQ, Zhou FC, Gao F, Bian JS, Shan F. Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase. J Agric Food Chem. 2009 Dec 23;57(24):11463-8. doi: 10.1021/jf903083h. PubMed PMID: 19938837.