Irigenin | CAS#548-76-5 | Isoflavonoid

MedKoo Cat#: 112083 | Name: Irigenin

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Description:

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

Irigenin is a polyketide synthase-derived isoflavonoid that increases survival and reduces cardiac apoptosis, fibrosis, and levels of TNF-α, IL-6, IL-18, and IL-1β in vivo.

Chemical Structure

Irigenin

CAS#548-76-5

Theoretical Analysis

MedKoo Cat#: 112083

Name: Irigenin

CAS#: 548-76-5

Chemical Formula: C18H16O8

Exact Mass: 360.0845

Molecular Weight: 360.32

Elemental Analysis: C, 60.00; H, 4.48; O, 35.52

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 300.00	2 Weeks
10mg	USD 550.00	2 Weeks

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Related CAS #

No Data

Synonym

Irigenin

IUPAC/Chemical Name

5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

InChi Key

TUGWPJJTQNLKCL-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3

SMILES Code

O=C1C(C2=CC(OC)=C(C(O)=C2)OC)=COC3=CC(O)=C(OC)C(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

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	27.75
	DMSO	10.0	27.75

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 360.32 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: Guo F, Wang X, Liu X. Protective effects of irigenin against 1-methyl-4-phenylpyridinium-induced neurotoxicity through regulating the Keap1/Nrf2 pathway. Phytother Res. 2021 Mar;35(3):1585-1596. doi: 10.1002/ptr.6926. Epub 2020 Oct 29. PMID: 33118665. 2: Zhang G, Liao Y, Yang H, Tao J, Ma L, Zuo X. Irigenin reduces the expression of caspase-3 and matrix metalloproteinases, thus suppressing apoptosis and extracellular matrix degradation in TNF-α-stimulated nucleus pulposus cells. Chem Biol Interact. 2021 Nov 1;349:109681. doi: 10.1016/j.cbi.2021.109681. Epub 2021 Oct 1. PMID: 34600870. 3: Zhang Q, Xue T, Guan J, Wang W, Shi J, Lu J, Jiang X. Irigenin alleviates angiotensin II-induced oxidative stress and apoptosis in HUVEC cells by activating Nrf2 pathway. Drug Dev Res. 2021 Nov;82(7):999-1007. doi: 10.1002/ddr.21802. Epub 2021 Feb 26. PMID: 33634899. 4: Hu T, Ge X, Wang J, Zhang N, Diao X, Hu L, Wang X. Metabolite identification of iridin in rats by using UHPLC-MS/MS and pharmacokinetic study of its metabolite irigenin. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Sep 1;1181:122914. doi: 10.1016/j.jchromb.2021.122914. Epub 2021 Aug 28. PMID: 34492510. 5: Xu Y, Gao CC, Pan ZG, Zhou CW. Irigenin sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells. Biochem Biophys Res Commun. 2018 Feb 12;496(3):998-1005. doi: 10.1016/j.bbrc.2018.01.003. Epub 2018 Jan 2. PMID: 29305260. 6: Guo L, Zheng X, Wang E, Jia X, Wang G, Wen J. Irigenin treatment alleviates doxorubicin (DOX)-induced cardiotoxicity by suppressing apoptosis, inflammation and oxidative stress via the increase of miR-425. Biomed Pharmacother. 2020 May;125:109784. doi: 10.1016/j.biopha.2019.109784. Epub 2020 Feb 25. PMID: 32092815. 7: Amin A, Chikan NA, Mokhdomi TA, Bukhari S, Koul AM, Shah BA, Gharemirshamlu FR, Wafai AH, Qadri A, Qadri RA. Irigenin, a novel lead from Western Himalayan chemiome inhibits Fibronectin-Extra Domain A induced metastasis in Lung cancer cells. Sci Rep. 2016 Nov 16;6:37151. doi: 10.1038/srep37151. PMID: 27849000; PMCID: PMC5111083. 8: Zhang WD, Yang WJ, Wang XJ, Gu Y, Wang R. Simultaneous determination of tectorigenin, irigenin and irisflorentin in rat plasma and urine by UHPLC-MS/MS: application to pharmacokinetics. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Dec 1;879(31):3735-41. doi: 10.1016/j.jchromb.2011.10.022. Epub 2011 Oct 25. PMID: 22071270. 9: Mao H, Ye X, Chen W, Geng W, Chen G. Fabrication of carbon nanotube- polylactic acid composite electrode by melt compounding for capillary electrophoretic determination of tectoridin and irigenin in Belamcandae Rhizoma. J Pharm Biomed Anal. 2019 Oct 25;175:112769. doi: 10.1016/j.jpba.2019.07.017. Epub 2019 Jul 10. PMID: 31398628. 10: Ahn KS, Noh EJ, Cha KH, Kim YS, Lim SS, Shin KH, Jung SH. Inhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E(2) production in murine macrophage RAW 264.7 cells. Life Sci. 2006 Apr 11;78(20):2336-42. doi: 10.1016/j.lfs.2005.09.041. Epub 2005 Nov 22. PMID: 16307761. 11: Baker W, Downing DF, Floyd AJ, Gilbert B, Ollis WD. Synthesis of isoflavones. V. Irigenin and tectorigenin. J Chem Soc Perkin 1. 1970;9:1219-23. doi: 10.1039/j39700001219. PMID: 5463830.