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MedKoo Cat#: 145647 | Name: hirsutenone

Description:

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

Hirsutenone a bioactive compound in Alnus japonica, exhibits anti-cancer effects against prostate cancer through a direct physical inhibition of Akt1/2. Hirsutenone suppressed anchorage-dependent and independent cell growth of PC3 and LNCaP human prostate cancer cells.

Chemical Structure

hirsutenone
hirsutenone
CAS#41137-87-5

Theoretical Analysis

MedKoo Cat#: 145647

Name: hirsutenone

CAS#: 41137-87-5

Chemical Formula: C19H20O5

Exact Mass: 328.1300

Molecular Weight: 328.36

Elemental Analysis: C, 69.50; H, 6.14; O, 24.36

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.
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Related CAS #
No Data
Synonym
Hirsutenone; HIRSUTANONE;
IUPAC/Chemical Name
(E)-1,7-bis(3,4-dihydroxyphenyl)hept-4-en-3-one
InChi Key
VWHYFMQKJYFLCC-DUXPYHPUSA-N
InChi Code
1S/C19H20O5/c20-15(8-5-14-7-10-17(22)19(24)12-14)4-2-1-3-13-6-9-16(21)18(23)11-13/h2,4,6-7,9-12,21-24H,1,3,5,8H2/b4-2+
SMILES Code
OC1=CC=C(CCC(=O)\C=C\CCC2=CC(O)=C(O)C=C2)C=C1O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 328.36 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
1: Kang S, Kim JE, Li Y, Jung SK, Song NR, Thimmegowda NR, Kim BY, Lee HJ, Bode AM, Dong Z, Lee KW. Hirsutenone in Alnus extract inhibits akt activity and suppresses prostate cancer cell proliferation. Mol Carcinog. 2015 Nov;54(11):1354-62. doi: 10.1002/mc.22211. Epub 2014 Sep 11. PMID: 25213146. 2: Yun J, Bae H, Choi SE, Kim JH, Choi YW, Lim I, Lee CS, Lee MW, Ko JH, Seo SJ, Bang H. Hirsutenone directly blocks human ether-a-go-go related gene K+ channels. Biol Pharm Bull. 2011;34(12):1815-22. doi: 10.1248/bpb.34.1815. PMID: 22130236. 3: Cheong LY, Suk S, Thimmegowda NR, Chung MY, Yang H, Seo SG, Shwetha B, Kim JE, Kwon JY, Kim BY, Lee KW. Hirsutenone Directly Targets PI3K and ERK to Inhibit Adipogenesis in 3T3-L1 Preadipocytes. J Cell Biochem. 2015 Jul;116(7):1361-70. doi: 10.1002/jcb.25093. PMID: 25756947. 4: Seo GS, Jiang WY, Park PH, Sohn DH, Cheon JH, Lee SH. Hirsutenone reduces deterioration of tight junction proteins through EGFR/Akt and ERK1/2 pathway both converging to HO-1 induction. Biochem Pharmacol. 2014 Jul 15;90(2):115-25. doi: 10.1016/j.bcp.2014.05.006. Epub 2014 May 20. PMID: 24853984. 5: Lee CS, Jang ER, Kim YJ, Myung SC, Kim W, Lee MW. Diarylheptanoid hirsutenone enhances apoptotic effect of TRAIL on epithelial ovarian carcinoma cell lines via activation of death receptor and mitochondrial pathway. Invest New Drugs. 2012 Apr;30(2):548-57. doi: 10.1007/s10637-010-9601-5. Epub 2010 Dec 1. PMID: 21120579. 6: Lee CS, Ko HH, Seo SJ, Choi YW, Lee MW, Myung SC, Bang H. Diarylheptanoid hirsutenone prevents tumor necrosis factor-alpha-stimulated production of inflammatory mediators in human keratinocytes through NF-kappaB inhibition. Int Immunopharmacol. 2009 Aug;9(9):1097-104. doi: 10.1016/j.intimp.2009.05.006. Epub 2009 May 20. PMID: 19464389. 7: Lee CS, Jang ER, Kim YJ, Lee MS, Seo SJ, Lee MW. Hirsutenone inhibits lipopolysaccharide-activated NF-kappaB-induced inflammatory mediator production by suppressing Toll-like receptor 4 and ERK activation. Int Immunopharmacol. 2010 Apr;10(4):520-5. doi: 10.1016/j.intimp.2010.01.015. Epub 2010 Feb 4. PMID: 20138154. 8: Lee DI, Jang SK, Park DW, Kim ST, Park JS, Jo BR, Park JY, Park HY, Joo SS. Diarylheptanoid Hirsutenone Attenuates Osteoclastogenesis by Suppressing IFNγ and NF-κB Signaling in Th1 and Preosteoclastic Cells. Biol Pharm Bull. 2017;40(5):630-637. doi: 10.1248/bpb.b16-00876. PMID: 28458348. 9: Kim JH, Lee KW, Lee MW, Lee HJ, Kim SH, Surh YJ. Hirsutenone inhibits phorbol ester-induced upregulation of COX-2 and MMP-9 in cultured human mammary epithelial cells: NF-kappaB as a potential molecular target. FEBS Lett. 2006 Jan 23;580(2):385-92. doi: 10.1016/j.febslet.2005.12.015. Epub 2005 Dec 19. PMID: 16380122. 10: Farrand L, Kim JY, Byun S, Im-aram A, Lee J, Suh JY, Lee KW, Lee HJ, Tsang BK. The diarylheptanoid hirsutenone sensitizes chemoresistant ovarian cancer cells to cisplatin via modulation of apoptosis-inducing factor and X-linked inhibitor of apoptosis. J Biol Chem. 2014 Jan 17;289(3):1723-31. doi: 10.1074/jbc.M113.513879. Epub 2013 Nov 18. PMID: 24247248; PMCID: PMC3894349. 11: Kang MJ, Eum JY, Jeong MS, Park SH, Moon KY, Kang MH, Kim MS, Choi SE, Lee MW, Lee DI, Bang H, Lee CS, Joo SS, Li K, Lee MK, Seo SJ, Choi YW. Tat peptide- admixed elastic liposomal formulation of hirsutenone for the treatment of atopic dermatitis in NC/Nga mice. Int J Nanomedicine. 2011;6:2459-67. doi: 10.2147/IJN.S24350. Epub 2011 Oct 20. PMID: 22072881; PMCID: PMC3205140. 12: Joo SS, Kim SG, Choi SE, Kim YB, Park HY, Seo SJ, Choi YW, Lee MW, Lee DI. Suppression of T cell activation by hirsutenone, isolated from the bark of Alnus japonica, and its therapeutic advantages for atopic dermatitis. Eur J Pharmacol. 2009 Jul 1;614(1-3):98-105. doi: 10.1016/j.ejphar.2009.04.047. Epub 2009 May 3. PMID: 19409888. 13: Seonu SY, Kim MJ, Yin J, Lee MW. Alnus sibirica Compounds Exhibiting Anti-Proliferative, Apoptosis-Inducing, and GSTP1 Demethylating Effects on Prostate Cancer Cells. Molecules. 2021 Jun 23;26(13):3830. doi: 10.3390/molecules26133830. PMID: 34201712; PMCID: PMC8270241. 14: Jo H, Choi SJ, Jung SH. Protective effects of a compound isolated from Alnus japonica on oxidative stress-induced death in transformed retinal ganglion cells. Food Chem Toxicol. 2013 Jun;56:425-35. doi: 10.1016/j.fct.2013.02.052. Epub 2013 Mar 14. PMID: 23500778. 15: Jeong MS, Choi SE, Kim JY, Kim JS, Kim EJ, Park KH, Lee DI, Joo SS, Lee CS, Bang H, Lee MK, Choi YW, Li KS, Moon NJ, Lee MW, Seo SJ. Atopic dermatitis-like skin lesions reduced by topical application and intraperitoneal injection of Hirsutenone in NC/Nga mice. Clin Dev Immunol. 2010;2010:618517. doi: 10.1155/2010/618517. Epub 2010 Dec 14. PMID: 21197410; PMCID: PMC3010703. 16: Yin J, Yoon SH, Ahn HS, Lee MW. Inhibitory Activity of Allergic Contact Dermatitis and Atopic Dermatitis-Like Skin in BALB/c Mouse through Oral Administration of Fermented Barks of Alnus sibirica. Molecules. 2018 Feb 18;23(2):450. doi: 10.3390/molecules23020450. PMID: 29463011; PMCID: PMC6017565. 17: Novaković M, Pešić M, Trifunović S, Vučković I, Todorović N, Podolski-Renić A, Dinić J, Stojković S, Tešević V, Vajs V, Milosavljević S. Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells. Phytochemistry. 2014 Jan;97:46-54. doi: 10.1016/j.phytochem.2013.11.001. Epub 2013 Nov 28. PMID: 24290194. 18: Adhikari B, Marasini BP, Rayamajhee B, Bhattarai BR, Lamichhane G, Khadayat K, Adhikari A, Khanal S, Parajuli N. Potential roles of medicinal plants for the treatment of viral diseases focusing on COVID-19: A review. Phytother Res. 2021 Mar;35(3):1298-1312. doi: 10.1002/ptr.6893. Epub 2020 Oct 9. PMID: 33037698; PMCID: PMC7675695. 19: Choi SE, Kim KH, Kwon JH, Kim SB, Kim HW, Lee MW. Cytotoxic activities of diarylheptanoids from Alnus japonica. Arch Pharm Res. 2008 Oct;31(10):1287-9. doi: 10.1007/s12272-001-2108-z. Epub 2008 Oct 29. PMID: 18958419. 20: da Cunha LNOL, Tizziani T, Souza GB, Moreira MA, Neto JSS, Dos Santos CVD, de Carvalho MG, Dalmarco EM, Turqueti LB, Scotti MT, Scotti L, de Assis FF, Braga AL, Sandjo LP. Natural Products with Tandem Anti-inflammatory, Immunomodulatory and Anti-SARS-CoV/2 Effects: A Drug Discovery Perspective against SARS-CoV-2. Curr Med Chem. 2022;29(14):2530-2564. doi: 10.2174/0929867328666210726094955. PMID: 34313197.

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