Homobutein

Names

[ Name ]:
Homobutein

[Synonym ]:
2',4,4'-trihydroxy-3-methoxychalcone
2-Propen-1-one,1-(2,4-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)
3-O-Methylbutein
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
EINECS 251-782-7
2',4,4'-trihydroxy-3-dimethoxychalcone
4,2',4'-trihydroxy-3-methoxy-trans-chalcone
Acrylophenone,2',4'-dihydroxy-3-(p-hydroxy-m-methoxyphenyl)
4,2',4'-Trihydroxy-3-methoxy-trans-chalkon
Homobutein

Biological Activity

[Description]:

Homobutein a natural chalcones (can be found in many medicinal plants, fruits, vegetables, spices and nuts), is a potent HDACs/NF-κB dual inhibitor with IC50s of 190 and 38 μM, respectively. Homobutein also a chelator of iron (II and III) cations, shows various activities, including anticancer, anti-inflammatory, antiparasite and antioxidation[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC

Signaling Pathways >> Epigenetics >> HDAC

[In Vitro]

Homobutein (compound 15) (20, 24, 28, 32, 40 μM; 2 h) inhibits the viability of K562 cells[1]. Homobutein (2 h) inhibits TNFα-induced NF-κB activity in K562 cells[1]. Homobutein (1 μg/mL; 72 h) inhibits the growth of Toxoplasma gondii by 19.48%[2]. Homobutein (24 h) againsts W2 and D6 strains of P.falciparum with IC50s of 15.0 and 16.1 µM, respectively[3]. Cell Viability Assay[1] Cell Line: K562 cells Concentration: 20, 24, 28, 32, 40 μM Incubation Time: 2 h Result: Showed inhibition of viability in K562 cells. Cell Viability Assay[2] Cell Line: Toxoplasma gondii RH-2F strain Concentration: 1 μg/mL Incubation Time: 72 h Result: Surpressed 19.48% of the Toxoplasma gondii.

[References]

[1]. Orlikova B, et al. Natural chalcones as dual inhibitors of HDACs and NF-κB. Oncol Rep. 2012 Sep;28(3):797-805.

[2]. Adeyemi OS, et al. In Vitro Screening to Identify Anti-Toxoplasma Compounds and In Silico Modeling for Bioactivities and Toxicity. Yale J Biol Med. 2019 Sep 20;92(3):369-383.

[3]. Yenesew A, et al. Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica. Phytochemistry. 2004 Nov;65(22):3029-32.

[4]. Serobatse K, et al. Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: a DFT study in vacuo and in solution. European Food Research and Technology, 2016, 242(1): 71-90.

Chemical & Physical Properties

[ Density]:
1.369 g/cm3

[ Boiling Point ]:
523.8ºC at 760 mmHg

[ Melting Point ]:
207-212ºC

[ Molecular Formula ]:
C₁₆H₁₄O₅

[ Molecular Weight ]:
286.27900

[ Flash Point ]:
197.6ºC

[ Exact Mass ]:
286.08400

[ PSA ]:
86.99000

[ LogP ]:
2.70810

[ Index of Refraction ]:
1.684

Safety Information

[ HS Code ]:
2914509090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%