Irilone | CAS#41653-81-0 | isoflavone

MedKoo Cat#: 14637 | Name: Irilone

Description:

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

Irilone is the second most abundant isoflavone next to daidzein in human plasma after consumption of a red clover-based dietary supplement (RCDS). Irilone increases luciferase activity from a hormone responsive element in a cell line that lacked ER and PR but expressed the glucocorticoid receptor (GR). Irilone that has been isolated from red clover previously demonstrated progestogenic potentiation activity.

Chemical Structure

Irilone

CAS#41653-81-0

Theoretical Analysis

MedKoo Cat#: 14637

Name: Irilone

CAS#: 41653-81-0

Chemical Formula: C16H10O6

Exact Mass: 298.0500

Molecular Weight: 298.25

Elemental Analysis: C, 64.43; H, 3.38; O, 32.19

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

Irilone;

IUPAC/Chemical Name

9-hydroxy-7-(4-hydroxyphenyl)-8H-[1,3]dioxolo[4,5-g]chromen-8-one

InChi Key

NUGRQNBDTZWXTP-UHFFFAOYSA-N

InChi Code

1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2

SMILES Code

OC1=CC=C(C=C1)C2=COC3=C(C2=O)C(O)=C4OCOC4=C3

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 298.25 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: Austin JR, Li K, Rivera Rodríguez R, Lantvit DD, Murphy BT, Burdette JE. Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors. J Nat Prod. 2021 Dec 24;84(12):3090-3099. doi: 10.1021/acs.jnatprod.1c00835. Epub 2021 Nov 23. PMID: 34813298; PMCID: PMC9152987. 2: Lee JH, Dean M, Austin JR, Burdette JE, Murphy BT. Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling. J Nat Prod. 2018 Sep 28;81(9):1962-1967. doi: 10.1021/acs.jnatprod.8b00131. Epub 2018 Sep 10. PMID: 30199256; PMCID: PMC6432775. 3: Lutter S, Schmalbach K, Esch HL, Lehmann L. The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover. Arch Toxicol. 2014 Feb;88(2):309-21. doi: 10.1007/s00204-013-1114-5. Epub 2013 Aug 28. PMID: 23982890. 4: Wu ZY, Sang LX, Chang B. Isoflavones and inflammatory bowel disease. World J Clin Cases. 2020 Jun 6;8(11):2081-2091. doi: 10.12998/wjcc.v8.i11.2081. PMID: 32548137; PMCID: PMC7281056. 5: Braune A, Maul R, Schebb NH, Kulling SE, Blaut M. The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota. Mol Nutr Food Res. 2010 Jul;54(7):929-38. doi: 10.1002/mnfr.200900233. PMID: 19998384. 6: Scheffler A, Albrecht AE, Esch HL, Lehmann L. Mutagenic potential of the isoflavone irilone in cultured V79 cells. Toxicol Lett. 2015 Apr 16;234(2):81-91. doi: 10.1016/j.toxlet.2015.02.013. Epub 2015 Feb 19. PMID: 25703823. 7: Scheffler A, Albrecht AE, Esch HL, Lehmann L. Data in support of the mutagenic potential of the isoflavone irilone in cultured V79 cells. Data Brief. 2015 Jul 17;4:474-87. doi: 10.1016/j.dib.2015.07.010. PMID: 26306322; PMCID: PMC4534604. 8: Maul R, Siegl D, Kulling SE. Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP- glucuronosyltransferases. Drug Metab Dispos. 2011 Apr;39(4):610-6. doi: 10.1124/dmd.110.033076. Epub 2010 Dec 21. PMID: 21177485. 9: Hitzman R, Malca-Garcia GR, Howell C, Park HY, Friesen JB, Dong H, Dunlap T, McAlpine JB, Vollmer G, Bosland MC, Nikolić D, Lankin DC, Chen SN, Bolton JL, Pauli GF, Dietz BM. DESIGNER fraction concept unmasks minor bioactive constituents in red clover (Trifolium pratense L.). Phytochemistry. 2023 Oct;214:113789. doi: 10.1016/j.phytochem.2023.113789. Epub 2023 Jul 21. PMID: 37482264; PMCID: PMC10528883. 10: Zhang L, Wei K, Xu J, Yang D, Zhang C, Wang Z, Li M. Belamcanda chinensis (L.) DC-An ethnopharmacological, phytochemical and pharmacological review. J Ethnopharmacol. 2016 Jun 20;186:1-13. doi: 10.1016/j.jep.2016.03.046. Epub 2016 Mar 23. PMID: 27032710. 11: Ochensberger S, Alperth F, Mitić B, Kunert O, Mayer S, Mourão MF, Turek I, Luca SV, Skalicka-Woźniak K, Maleš Ž, Hruševar D, Duka I, Bucar F. Phenolic compounds of Iris adriatica and their antimycobacterial effects. Acta Pharm. 2019 Dec 1;69(4):673-681. doi: 10.2478/acph-2019-0037. PMID: 31639092. 12: Rigano D, Formisano C, Grassia A, Grassia G, Perrone A, Piacente S, Vuotto ML, Senatore F. Antioxidant flavonoids and isoflavonoids from rhizomes of Iris pseudopumila. Planta Med. 2007 Jan;73(1):93-6. doi: 10.1055/s-2006-957071. PMID: 17315314. 13: Messanga BB, Kimbu SF, Sondengam BL, Bodo B. Triflavonoids of Ochna calodendron. Phytochemistry. 2002 Feb;59(4):435-8. doi: 10.1016/s0031-9422(01)00414-9. PMID: 11830163. 14: Malca Garcia GR, Friesen JB, Liu Y, Nikolić D, Lankin DC, McAlpine JB, Chen SN, Pauli GF. Preparation of DESIGNER extracts of red clover (Trifolium pratense L.) by centrifugal partition chromatography. J Chromatogr A. 2019 Nov 8;1605:360277. doi: 10.1016/j.chroma.2019.05.057. Epub 2019 May 29. PMID: 31307793; PMCID: PMC6864275. 15: Ibrahim SR, Mohamed GA, Al-Musayeib NM. New constituents from the rhizomes of Egyptian Iris germanica L. Molecules. 2012 Mar 2;17(3):2587-98. doi: 10.3390/molecules17032587. PMID: 22388969; PMCID: PMC6268570. 16: Muchiri RN, van Breemen RB. Single-Laboratory Validation of UHPLC-MS/MS Assays for Red Clover Isoflavones in Human Serum and Dietary Supplements. J AOAC Int. 2020 Jul 1;103(4):1160-1166. doi: 10.1093/jaoacint/qsaa033. PMID: 33241325; PMCID: PMC7691648. 17: Singh S, Gaur S. Virtually selected phytochemicals from edible seeds as possible potential medicaments for hypercholesterolemia: an in silico approach. J Biomol Struct Dyn. 2023 Oct-Nov;41(18):8690-8700. doi: 10.1080/07391102.2022.2135604. Epub 2022 Oct 19. PMID: 36259535. 18: Zhang YY, Wang Q, Qi LW, Qin XY, Qin MJ. Characterization and determination of the major constituents in Belamcandae Rhizoma by HPLC-DAD-ESI-MS(n). J Pharm Biomed Anal. 2011 Sep 10;56(2):304-14. doi: 10.1016/j.jpba.2011.05.040. Epub 2011 Jun 6. PMID: 21715119. 19: Tsao R, Papadopoulos Y, Yang R, Young JC, McRae K. Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages. J Agric Food Chem. 2006 Aug 9;54(16):5797-805. doi: 10.1021/jf0614589. PMID: 16881680. 20: Kostić AŽ, Gašić UM, Pešić MB, Stanojević SP, Barać MB, Mačukanović-Jocić MP, Avramov SN, Tešić ŽL. Phytochemical Analysis and Total Antioxidant Capacity of Rhizome, Above-Ground Vegetative Parts and Flower of Three Iris Species. Chem Biodivers. 2019 Mar;16(3):e1800565. doi: 10.1002/cbdv.201800565. Epub 2019 Feb 28. PMID: 30609204.