Prunetin | CAS#552-59-0 | isoflavone

MedKoo Cat#: 146243 | Name: Prunetin

Description:

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

Prunetin is a naturally occurring O-methylated isoflavone, first isolated from the bark of Prunus emarginata (Oregon cherry) in 1910. It has been identified as an attractant for Aphanomyces euteiches zoospores in pea roots and as an allosteric inhibitor of human liver aldehyde dehydrogenase. Additionally, prunetin has been shown to lower blood pressure in spontaneously hypertensive rats by relaxing isolated rat aortic rings through calcium channel blockade mechanisms in vascular smooth muscle .

Chemical Structure

Prunetin

CAS#552-59-0

Theoretical Analysis

MedKoo Cat#: 146243

Name: Prunetin

CAS#: 552-59-0

Chemical Formula: C16H12O5

Exact Mass: 284.0685

Molecular Weight: 284.27

Elemental Analysis: C, 67.60; H, 4.26; O, 28.14

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

Prunetin; Prunusetin;

IUPAC/Chemical Name

5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

InChi Key

KQMVAGISDHMXJJ-UHFFFAOYSA-N

InChi Code

1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

SMILES Code

COC1=CC2=C(C(=O)C(=CO2)C3=CC=C(O)C=C3)C(O)=C1

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 284.27 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: Hamed AB, El-Abhar HS, Abdallah DM, Ahmed KA, Abulfadl YS. Prunetin in a GPR30-dependent manner mitigates renal ischemia/reperfusion injury in rats via interrupting indoxyl sulfate/TLR4/TRIF, RIPK1/RIPK3/MLKL, and RIPK3/PGAM5/DRP-1 crosstalk. Saudi Pharm J. 2023 Nov;31(11):101818. doi: 10.1016/j.jsps.2023.101818. Epub 2023 Oct 5. PMID: 37868646; PMCID: PMC10587762. 2: Patel K, Patel DK. The Potential Therapeutic Properties of Prunetin against Human Health Complications: A Review of Medicinal Importance and Pharmacological Activities. Drug Metab Bioanal Lett. 2022;15(3):166-177. doi: 10.2174/2949681015666220912104743. PMID: 36098409. 3: Jeong SH, Kim HH, Park MY, Bhosale PB, Abusaliya A, Hwang KH, Moon YG, Heo JD, Seong JK, Ahn M, Park KI, Won CK, Kim GS. Potential Anticancer Effects of Isoflavone Prunetin and Prunetin Glycoside on Apoptosis Mechanisms. Int J Mol Sci. 2024 Oct 31;25(21):11713. doi: 10.3390/ijms252111713. PMID: 39519265; PMCID: PMC11545868. 4: Kim B, Jo C, Choi HY, Lee K. Prunetin Relaxed Isolated Rat Aortic Rings by Blocking Calcium Channels. Molecules. 2018 Sep 17;23(9):2372. doi: 10.3390/molecules23092372. PMID: 30227625; PMCID: PMC6225200. 5: Köksal Karayildirim Ç, Nalbantsoy A, Karabay Yavaşoğlu NÜ. Prunetin inhibits nitric oxide activity and induces apoptosis in urinary bladder cancer cells via CASP3 and TNF-α genes. Mol Biol Rep. 2021 Nov;48(11):7251-7259. doi: 10.1007/s11033-021-06719-w. Epub 2021 Oct 2. PMID: 34599704. 6: Park TJ, Hong H, Kim MS, Park JS, Chi WJ, Kim SY. Prunetin 4'-O-Phosphate, a Novel Compound, in RAW 264.7 Macrophages Exerts Anti- Inflammatory Activity via Suppression of MAP Kinases and the NFκB Pathway. Molecules. 2021 Nov 12;26(22):6841. doi: 10.3390/molecules26226841. PMID: 34833933; PMCID: PMC8622051. 7: Khan K, Pal S, Yadav M, Maurya R, Trivedi AK, Sanyal S, Chattopadhyay N. Prunetin signals via G-protein-coupled receptor, GPR30(GPER1): Stimulation of adenylyl cyclase and cAMP-mediated activation of MAPK signaling induces Runx2 expression in osteoblasts to promote bone regeneration. J Nutr Biochem. 2015 Dec;26(12):1491-501. doi: 10.1016/j.jnutbio.2015.07.021. Epub 2015 Aug 8. Erratum in: J Nutr Biochem. 2017 Sep;47:132. doi: 10.1016/j.jnutbio.2017.07.004.. For mistakes in the representative immunostaining images in Fig. 6A. PMID: 26345541. 8: Li J, Sun Y, Xiong X, Wang M, Zuo L, Wang Y, Geng Z. [Prunetin inhibits TLR4/MyD88 pathway to attenuate intestinal epithelial inflammatory response and ameliorate mouse Crohn's disease-like colitis]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2024 Mar;40(3):199-206. Chinese. PMID: 38512029. 9: Samy JVRA, Kumar N, Singaravel S, Krishnamoorthy R, Alshuniaber MA, Gatasheh MK, Venkatesan A, Natesan V, Kim SJ. Effect of Prunetin on Streptozotocin- Induced Diabetic Nephropathy in Rats - a Biochemical and Molecular Approach. Biomol Ther (Seoul). 2023 Nov 1;31(6):619-628. doi: 10.4062/biomolther.2023.068. Epub 2023 Oct 11. PMID: 37818618; PMCID: PMC10616515. 10: Han J, Zheng S, Jin J, Wu T, Shi Y, Yang K, Zhang H, Li Y, Sun Y, Lv Y, Yao C, Lin T, Zhu C, Liu H. Polydopamine-loaded prunetin nanomaterials activate DRD2 to reduce UV-induced inflammation by stabilizing and promoting Nrf2 nuclear translocation. Acta Biomater. 2023 Oct 1;169:556-565. doi: 10.1016/j.actbio.2023.07.050. Epub 2023 Jul 31. PMID: 37532131. 11: Vetrivel P, Kim SM, Ha SE, Kim HH, Bhosale PB, Senthil K, Kim GS. Compound Prunetin Induces Cell Death in Gastric Cancer Cell with Potent Anti- Proliferative Properties: In Vitro Assay, Molecular Docking, Dynamics, and ADMET Studies. Biomolecules. 2020 Jul 21;10(7):1086. doi: 10.3390/biom10071086. PMID: 32708333; PMCID: PMC7408406. 12: Hu H, Li H. Prunetin inhibits lipopolysaccharide-induced inflammatory cytokine production and MUC5AC expression by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells. Biomed Pharmacother. 2018 Oct;106:1469-1477. doi: 10.1016/j.biopha.2018.07.093. Epub 2018 Jul 24. PMID: 30119221. 13: Piegholdt S, Rimbach G, Wagner AE. The phytoestrogen prunetin affects body composition and improves fitness and lifespan in male Drosophila melanogaster. FASEB J. 2016 Feb;30(2):948-58. doi: 10.1096/fj.15-282061. Epub 2015 Nov 4. PMID: 26538555. 14: Vetrivel P, Nachimuthu S, Abuyaseer A, Bhosale PB, Ha SE, Kim HH, Park MY, Kim GS. Investigation on the cellular mechanism of Prunetin evidenced through next generation sequencing and bioinformatic approaches against gastric cancer. Sci Rep. 2022 Jul 13;12(1):11852. doi: 10.1038/s41598-022-15826-y. PMID: 35831348; PMCID: PMC9279440. 15: Yang G, Ham I, Choi HY. Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway. Food Chem Toxicol. 2013 Aug;58:124-32. doi: 10.1016/j.fct.2013.03.039. Epub 2013 Apr 15. PMID: 23597450. 16: Bithi SA, Al Hasan MS, Bhuia MS, Mia E, Yana NT, Hasan AMW, Uddin MB, Sayeed MA, Emon Y, Hasan R, Chowdhury R, Islam MT. Botanical sources, biopharmaceutical profile, anticancer effects with mechanistic insight, toxicological and clinical evidence of prunetin: a literature review. Med Oncol. 2025 Mar 3;42(4):87. doi: 10.1007/s12032-025-02646-z. PMID: 40029540. 17: Nam DC, Kim BK, Lee HJ, Shin HD, Lee CJ, Hwang SC. Effects of prunetin on the proteolytic activity, secretion and gene expression of MMP-3 in vitro and production of MMP-3 in vivo. Korean J Physiol Pharmacol. 2016 Mar;20(2):221-8. doi: 10.4196/kjpp.2016.20.2.221. Epub 2016 Feb 23. PMID: 26937219; PMCID: PMC4770113. 18: Sugai T, Hanaya K, Higashibayashi S. Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement. Biosci Biotechnol Biochem. 2021 Jan 7;85(1):143-147. doi: 10.1093/bbb/zbaa021. PMID: 33577652. 19: Beszterda M, Kasperkowiak M, Frański R. Comment on the published data concerning the identification of biochanin A and prunetin by LC/ESI-MS. Talanta. 2020 May 1;211:120733. doi: 10.1016/j.talanta.2020.120733. Epub 2020 Jan 11. PMID: 32070588. 20: Piegholdt S, Rimbach G, Wagner AE. Effects of the isoflavone prunetin on gut health and stress response in male Drosophila melanogaster. Redox Biol. 2016 Aug;8:119-26. doi: 10.1016/j.redox.2016.01.001. Epub 2016 Jan 6. PMID: 26774080; PMCID: PMC4732017.