Irisolidone | CAS#2345-17-7 | biochemical

MedKoo Cat#: 146096 | Name: Irisolidone

Description:

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

Irisolidone is a natural compound primarily derived from plants like Iris germanica and exhibits notable anti-inflammatory, antioxidant, and antimicrobial properties. It has shown promise in pharmaceutical and cosmetic applications, particularly in the treatment of skin conditions and as a potential therapeutic for inflammatory diseases. The mechanism of action of irisolidone involves the modulation of key inflammatory pathways, such as the inhibition of NF-κB signaling, which helps reduce inflammation and oxidative stress.

Chemical Structure

Irisolidone

CAS#2345-17-7

Theoretical Analysis

MedKoo Cat#: 146096

Name: Irisolidone

CAS#: 2345-17-7

Chemical Formula: C17H14O6

Exact Mass: 314.0790

Molecular Weight: 314.29

Elemental Analysis: C, 64.97; H, 4.49; O, 30.54

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Irisolidone;

IUPAC/Chemical Name

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

InChi Key

VOOFPOMXNLNEOF-UHFFFAOYSA-N

InChi Code

1S/C17H14O6/c1-21-10-5-3-9(4-6-10)11-8-23-13-7-12(18)17(22-2)16(20)14(13)15(11)19/h3-8,18,20H,1-2H3

SMILES Code

COC1=CC=C(C=C1)C2=COC3=CC(O)=C(OC)C(O)=C3C2=O

Appearance

To be determined

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

Preparing Stock Solutions

The following data is based on the product molecular weight 314.29 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: Patel DK. Herbal Phytomedicine 'Irisolidone' in Chronic Diseases: Biological Efficacy and Pharmacological Activity. Recent Adv Antiinfect Drug Discov. 2022;17(1):13-22. doi: 10.2174/1574891X16666220304231934. PMID: 35249525. 2: Kang GD, Lee SY, Jang SE, Han MJ, Kim DH. Irisolidone attenuates ethanol- induced gastric injury in mice by inhibiting the infiltration of neutrophils. Mol Nutr Food Res. 2017 Feb;61(2). doi: 10.1002/mnfr.201600517. Epub 2016 Oct 5. PMID: 27546737. 3: Jang HM, Park KT, Noh HD, Lee SH, Kim DH. Kakkalide and irisolidone alleviate 2,4,6-trinitrobenzenesulfonic acid-induced colitis in mice by inhibiting lipopolysaccharide binding to toll-like receptor-4 and proteobacteria population. Int Immunopharmacol. 2019 Aug;73:246-253. doi: 10.1016/j.intimp.2019.05.008. Epub 2019 May 18. PMID: 31112869. 4: Kim SY, Kim DH, Hyun JW, Henson JW, Kim HS. Irisolidone, an isoflavone metabolite, represses JC virus gene expression via inhibition of Sp1 binding in human glial cells. Biochem Biophys Res Commun. 2006 May 26;344(1):3-8. doi: 10.1016/j.bbrc.2006.03.165. PMID: 16630573. 5: Zhang G, Qi W, Xu L, Kano Y, Yuan D. Pharmacokinetics of irisolidone and its main metabolites in rat plasma determined by ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Nov 15;1005:23-9. doi: 10.1016/j.jchromb.2015.09.040. Epub 2015 Oct 9. PMID: 26465087. 6: Zhang G, Sun J, Kano Y, Yuan D. Metabolic profile of irisolidone in rats obtained by ultra-high performance liquid chromatography/quadrupole time-of- flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Dec 15;941:1-9. doi: 10.1016/j.jchromb.2013.09.033. Epub 2013 Oct 7. PMID: 24184829. 7: Min SW, Park YJ, Kim DH. Kakkalide and its metabolite irisolidone ameliorate carrageenan-induced inflammation in mice by inhibiting NF-κB pathway. Inflammation. 2011 Oct;34(5):344-51. doi: 10.1007/s10753-010-9240-1. PMID: 20686830. 8: Lee HU, Bae EA, Kim DH. Hepatoprotective effects of irisolidone on tert-butyl hyperoxide-induced liver injury. Biol Pharm Bull. 2005 Mar;28(3):531-3. doi: 10.1248/bpb.28.531. PMID: 15744084. 9: Min SW, Kim DH. Kakkalide and irisolidone: HMG-CoA reductase inhibitors isolated from the flower of Pueraria thunbergiana. Biol Pharm Bull. 2007 Oct;30(10):1965-8. doi: 10.1248/bpb.30.1965. PMID: 17917273. 10: Kang KA, Zhang R, Piao MJ, Ko DO, Wang ZH, Kim BJ, Park JW, Kim HS, Kim DH, Hyun JW. Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect. Bioorg Med Chem. 2008 Feb 1;16(3):1133-41. doi: 10.1016/j.bmc.2007.10.085. Epub 2007 Oct 30. PMID: 17996449. 11: Kim SY, Lee EJ, Woo MS, Jung JS, Hyun JW, Min SW, Kim DH, Kim HS. Inhibition of matrix metalloproteinase-9 gene expression by an isoflavone metabolite, irisolidone in U87MG human astroglioma cells. Biochem Biophys Res Commun. 2008 Feb 8;366(2):493-9. doi: 10.1016/j.bbrc.2007.11.178. Epub 2007 Dec 10. PMID: 18070596. 12: Zhang G, Gong T, Kano Y, Yuan D. Screening for in vitro metabolites of kakkalide and irisolidone in human and rat intestinal bacteria by ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Feb 1;947-948:117-24. doi: 10.1016/j.jchromb.2013.12.017. Epub 2013 Dec 25. PMID: 24412694. 13: Wang H, Bai X, Sun J, Kano Y, Makino T, Yuan D. Metabolism and excretion of kakkalide and its metabolites in rat urine, bile, and feces as determined by HPLC/UV and LC/MS/MS. Planta Med. 2013 Nov;79(16):1552-7. doi: 10.1055/s-0033-1350832. Epub 2013 Oct 9. PMID: 24108437. 14: Han YO, Han MJ, Park SH, Kim DH. Protective effects of kakkalide from Flos puerariae on ethanol-induced lethality and hepatic injury are dependent on its biotransformation by human intestinal microflora. J Pharmacol Sci. 2003 Nov;93(3):331-6. doi: 10.1254/jphs.93.331. PMID: 14646251. 15: Mu YL, Xie YY, Zhou L, Zhong Y, Liu L, Bai H, Wang YS, Zhang XM. Cardioprotective effect of 'methylamine irisolidone', a new compound, in hypoxia/reoxygenation injury in cultured rat cardiac myocytes. Chem Biodivers. 2009 Aug;6(8):1170-7. doi: 10.1002/cbdv.200800314. PMID: 19697334. 16: Bae EA, Han MJ, Kim DH. In vitro anti-Helicobacter pylori activity of irisolidone isolated from the flowers and rhizomes of Pueraria thunbergiana. Planta Med. 2001 Mar;67(2):161-3. doi: 10.1055/s-2001-11499. PMID: 11301866. 17: Chen C, Li X, Kano Y, Yuan D, Qu J. Oriental traditional herbal Medicine-- Puerariae Flos: A systematic review. J Ethnopharmacol. 2023 Apr 24;306:116089. doi: 10.1016/j.jep.2022.116089. Epub 2023 Jan 5. PMID: 36621660. 18: Park JS, Woo MS, Kim DH, Hyun JW, Kim WK, Lee JC, Kim HS. Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide-stimulated microglial cells. J Pharmacol Exp Ther. 2007 Mar;320(3):1237-45. doi: 10.1124/jpet.106.114322. Epub 2006 Dec 28. PMID: 17194798. 19: Mykhailenko O, Hsieh CF, El-Shazly M, Nikishin A, Kovalyov V, Shynkarenko P, Ivanauskas L, Chen BH, Horng JT, Hwang TL, Georgiyants V, Korinek M. Anti-viral and Anti-inflammatory Isoflavonoids from Ukrainian Iris aphylla Rhizomes: Structure-Activity Relationship Coupled with ChemGPS-NP Analysis. Planta Med. 2023 Sep;89(11):1063-1073. doi: 10.1055/a-2063-5265. Epub 2023 Mar 28. PMID: 36977489. 20: Bharti R, Chopra BS, Raut S, Khatri N. Pueraria tuberosa: A Review on Traditional Uses, Pharmacology, and Phytochemistry. Front Pharmacol. 2021 Jan 27;11:582506. doi: 10.3389/fphar.2020.582506. PMID: 33708108; PMCID: PMC7941752.