Isorhamnetin
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MedKoo CAT#: 540235

CAS#: 480-19-3

Description: Isorhamnetin, also called 3-Methylquercetin, is found in Tagetes. It exhibits a variety of biological activities, including decreasing expression of COX-2 and production of ROS in edema, inducing cell cycle arrest in colon cancer cells, and suppressing activity of Src and β-catenin to prevent DSS- and azoxymethane-induced carcinogenesis.

Chemical Structure

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Isorhamnetin
CAS# 480-19-3
Instruction

Theoretical Analysis

MedKoo Cat#: 540235
Name: Isorhamnetin
CAS#: 480-19-3
Chemical Formula: C16H12O7
Exact Mass: 316.06
Molecular Weight: 316.260
Elemental Analysis: C, 60.76; H, 3.82; O, 35.41

Price and Availability

Size Price Availability Quantity
25mg USD 285 2 Weeks
100mg USD 550 2 Weeks
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Synonym: 4H-1-Benzopyran-4-one, 2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-; 3-Methylquercetin; Quercetin; Isorhamnetin; 3'-O-methyl Quercetin;

IUPAC/Chemical Name: 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

InChi Key: IZQSVPBOUDKVDZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

SMILES Code: O=C1C(O)=C(C2=CC=C(O)C(OC)=C2)OC3=CC(O)=CC(O)=C13

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 316.26 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:
In vitro protocol:
In vivo protocol:

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1: Abdal Dayem A, Choi HY, Kim YB, Cho SG. Antiviral effect of methylated flavonol isorhamnetin against influenza. PLoS One. 2015 Mar 25;10(3):e0121610. doi: 10.1371/journal.pone.0121610. eCollection 2015. PubMed PMID: 25806943; PubMed Central PMCID: PMC4373826.

2: Zhang BY, Wang YM, Gong H, Zhao H, Lv XY, Yuan GH, Han SR. Isorhamnetin flavonoid synergistically enhances the anticancer activity and apoptosis induction by cis-platin and carboplatin in non-small cell lung carcinoma (NSCLC). Int J Clin Exp Pathol. 2015 Jan 1;8(1):25-37. eCollection 2015. PubMed PMID: 25755690; PubMed Central PMCID: PMC4348816.

3: Wang X, Zhong W. Isorhamnetin attenuates collagen-induced arthritis via modulating cytokines and oxidative stress in mice. Int J Clin Exp Med. 2015 Sep 15;8(9):16536-42. eCollection 2015. PubMed PMID: 26629181; PubMed Central PMCID: PMC4659069.

4: Dou W, Zhang J, Li H, Kortagere S, Sun K, Ding L, Ren G, Wang Z, Mani S. Plant flavonol isorhamnetin attenuates chemically induced inflammatory bowel disease via a PXR-dependent pathway. J Nutr Biochem. 2014 Sep;25(9):923-33. doi: 10.1016/j.jnutbio.2014.04.006. Epub 2014 May 9. PubMed PMID: 24913217; PubMed Central PMCID: PMC4125479.

5: Duan J, Xie Y, Luo H, Li G, Wu T, Zhang T. Transport characteristics of isorhamnetin across intestinal Caco-2 cell monolayers and the effects of transporters on it. Food Chem Toxicol. 2014 Apr;66:313-20. doi: 10.1016/j.fct.2014.02.003. Epub 2014 Feb 10. PubMed PMID: 24525098.

6: Han X, Piao MJ, Kim KC, Madduma Hewage SR, Yoo ES, Koh YS, Kang HK, Shin JH, Park Y, Yoo SJ, Chae S, Hyun JW. Isorhamnetin Protects Human Keratinocytes against Ultraviolet B-Induced Cell Damage. Biomol Ther (Seoul). 2015 Jul;23(4):357-66. doi: 10.4062/biomolther.2015.005. Epub 2015 Jul 1. PubMed PMID: 26157553; PubMed Central PMCID: PMC4489831.

7: Yang JH, Shin BY, Han JY, Kim MG, Wi JE, Kim YW, Cho IJ, Kim SC, Shin SM, Ki SH. Isorhamnetin protects against oxidative stress by activating Nrf2 and inducing the expression of its target genes. Toxicol Appl Pharmacol. 2014 Jan 15;274(2):293-301. doi: 10.1016/j.taap.2013.10.026. Epub 2013 Nov 7. PubMed PMID: 24211276.

8: Li C, Yang D, Zhao Y, Qiu Y, Cao X, Yu Y, Guo H, Gu X, Yin X. Inhibitory Effects of Isorhamnetin on the Invasion of Human Breast Carcinoma Cells by Downregulating the Expression and Activity of Matrix Metalloproteinase-2/9. Nutr Cancer. 2015;67(7):1191-200. doi: 10.1080/01635581.2015.1073763. Epub 2015 Sep 11. PubMed PMID: 26359917.

9: Seo S, Seo K, Ki SH, Shin SM. Isorhamnetin Inhibits Reactive Oxygen Species-Dependent Hypoxia Inducible Factor (HIF)-1α Accumulation. Biol Pharm Bull. 2016;39(11):1830-1838. PubMed PMID: 27803454.

10: Li W, Chen Z, Yan M, He P, Chen Z, Dai H. The protective role of isorhamnetin on human brain microvascular endothelial cells from cytotoxicity induced by methylglyoxal and oxygen-glucose deprivation. J Neurochem. 2016 Feb;136(3):651-9. doi: 10.1111/jnc.13436. Epub 2015 Dec 10. PubMed PMID: 26578299.

11: Yang JH, Kim SC, Kim KM, Jang CH, Cho SS, Kim SJ, Ku SK, Cho IJ, Ki SH. Isorhamnetin attenuates liver fibrosis by inhibiting TGF-β/Smad signaling and relieving oxidative stress. Eur J Pharmacol. 2016 Jul 15;783:92-102. doi: 10.1016/j.ejphar.2016.04.042. Epub 2016 May 3. PubMed PMID: 27151496.

12: Dong GZ, Lee JH, Ki SH, Yang JH, Cho IJ, Kang SH, Zhao RJ, Kim SC, Kim YW. AMPK activation by isorhamnetin protects hepatocytes against oxidative stress and mitochondrial dysfunction. Eur J Pharmacol. 2014 Oct 5;740:634-40. doi: 10.1016/j.ejphar.2014.06.017. Epub 2014 Jun 24. PubMed PMID: 24972246.

13: Antunes-Ricardo M, Moreno-García BE, Gutiérrez-Uribe JA, Aráiz-Hernández D, Alvarez MM, Serna-Saldivar SO. Induction of apoptosis in colon cancer cells treated with isorhamnetin glycosides from Opuntia ficus-indica pads. Plant Foods Hum Nutr. 2014 Dec;69(4):331-6. doi: 10.1007/s11130-014-0438-5. PubMed PMID: 25186940.

14: Hu S, Huang L, Meng L, Sun H, Zhang W, Xu Y. Isorhamnetin inhibits cell proliferation and induces apoptosis in breast cancer via Akt and mitogen activated protein kinase kinase signaling pathways. Mol Med Rep. 2015 Nov;12(5):6745-51. PubMed PMID: 26502751; PubMed Central PMCID: PMC4626180.

15: Chen TL, Zhu GL, Wang JA, Zhang GD, Liu HF, Chen JR, Wang Y, He XL. Protective effects of isorhamnetin on apoptosis and inflammation in TNF-α-induced HUVECs injury. Int J Clin Exp Pathol. 2015 Mar 1;8(3):2311-20. eCollection 2015. PubMed PMID: 26045738; PubMed Central PMCID: PMC4440047.

16: Du LY, Zhao M, Xu J, Qian DW, Jiang S, Shang EX, Guo JM, Duan JA. Analysis of the metabolites of isorhamnetin 3-O-glucoside produced by human intestinal flora in vitro by applying ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Agric Food Chem. 2014 Mar 26;62(12):2489-95. doi: 10.1021/jf405261a. Epub 2014 Mar 17. PubMed PMID: 24601527.

17: Yang B, Li XP, Ni YF, Du HY, Wang R, Li MJ, Wang WC, Li MM, Wang XH, Li L, Zhang WD, Jiang T. Protective Effect of Isorhamnetin on Lipopolysaccharide-Induced Acute Lung Injury in Mice. Inflammation. 2016 Feb;39(1):129-137. doi: 10.1007/s10753-015-0231-0. PubMed PMID: 26276127.

18: Xie Y, Luo H, Duan J, Hong C, Ma P, Li G, Zhang T, Wu T, Ji G. Phytic acid enhances the oral absorption of isorhamnetin, quercetin, and kaempferol in total flavones of Hippophae rhamnoides L. Fitoterapia. 2014 Mar;93:216-25. doi: 10.1016/j.fitote.2014.01.013. Epub 2014 Jan 21. PubMed PMID: 24462958.

19: Zhao JJ, Song JQ, Pan SY, Wang K. Treatment with Isorhamnetin Protects the Brain Against Ischemic Injury in Mice. Neurochem Res. 2016 Aug;41(8):1939-48. doi: 10.1007/s11064-016-1904-2. Epub 2016 May 9. PubMed PMID: 27161367.

20: Li C, Yang X, Chen C, Cai S, Hu J. Isorhamnetin suppresses colon cancer cell growth through the PI3K Akt mTOR pathway. Mol Med Rep. 2014 Mar;9(3):935-40. doi: 10.3892/mmr.2014.1886. Epub 2014 Jan 7. PubMed PMID: 24398569.