Butein

Names

[ CAS No. ]:
487-52-5

[ Name ]:
Butein

[Synonym ]:
Chalcone, 2',3,4,4'-tetrahydroxy- (7CI,8CI)
MFCD00017300
(E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
(2E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one
(2E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Einecs 207-659-5
2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-, (2E)-
Butein,2',3,4,4'-Tetrahydroxychalcone
Butein
2',3,4,4'-TETRAHYDROCHALCONE
3,4,2',4'-TETRAHYDROXYCHALCONE
QR CQ DV1U1R CQ DQ &&E Form
2',3,4,4'-TETRAHYDROXYCHALCONE
(E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one
2′,3,4,4′-Tetrahydroxychalcone

Biological Activity

[Description]:

Butein, a plant polyphenol isolated from Rhus verniciflua, inhibit the activation of protein tyrosine kinase and EGFR. target: EGFR [1]In vitro: 1) Butein inhibited the activation of AKT, extracellular signal-regulated kinase (ERKs) and p38 kinases in the presence of cisplatin.[2] 2) FoxO3a and its downstream molecules play a role in the synergistic effects of butein and cisplatin.[2]3) Butein suppresses cell proliferation and enhances apoptosis in paclitaxel-resistant ovarian cancer cells.[3]4) Butein activates FOXO3a/p27kip1 pathway in ALL cell lines.[4]5) Butein inhibited not only the epidermal growth factor (EGF)-stimulated auto-phosphotyrosine level of EGF receptor in HepG2 cells but also tyrosine-specific protein kinase activities of EGF receptor (IC50= 65 μM) and p60c-src(IC50= 65 μM)In vivo: 1) Butein in combination with cisplatin suppresses tumor growth and increases FoxO3a expression.[1]

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Natural Products >> Phenols

Research Areas >> Cancer

[Target]

EGFR

[References]

[1]. Er-Bin Yang et al. Butein, a Specific Protein Tyrosine Kinase Inhibitor. Biochem Biophys Res Commun, 1998 Apr 17, 245(2):435-8.

[2]. Zhang L et al. Butein sensitizes HeLa cells to cisplatin through the AKT and ERK/p38 MAPK pathways by targeting FoxO3a. Int J Mol Med, 2015 Oct, 36(4):957-66

[3]. Hyeong Sim Choi et al. Rhus verniciflua Stokes (RVS) and butein induce apoptosis of paclitaxel-resistant SKOV-3/PAX ovarian cancer cells through inhibition of AKT phosphorylation. BMC Complement Altern Med, 2016, 16: 122.

[4]. Tang YL et al. Butein inhibits cell proliferation and induces cell cycle arrest in acute lymphoblastic leukemia via FOXO3a/p27kip1 pathway. Oncotarget, 2016 Apr 5, 7(14):18651-64.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
560.9±50.0 °C at 760 mmHg

[ Melting Point ]:
216°C

[ Molecular Formula ]:
C₁₅H₁₂O₅

[ Molecular Weight ]:
272.25

[ Flash Point ]:
307.1±26.6 °C

[ PSA ]:
17.07000

[ LogP ]:
2.66

[ Appearance of Characters ]:
solid | yellow

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.748

[ Storage condition ]:
-20°C

[ Water Solubility ]:
DMSO: >50 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Precursor & DownStream

Precursor

DownStream

Articles

Butein sensitizes HeLa cells to cisplatin through the AKT and ERK/p38 MAPK pathways by targeting FoxO3a.

Int. J. Mol. Med. 36 , 957-66, (2015)

Drug resistance remains a major challenge in cancer therapy. Butein, a polyphenolic compound, has been shown to exhibit anticancer activity through the inhibition of the activation of the protein kina...

Butein, a novel dual inhibitor of MET and EGFR, overcomes gefitinib-resistant lung cancer growth.

Mol. Carcinog. 54(4) , 322-31, (2015)

Lung cancer is a leading cause of death worldwide and MET amplification is a major therapeutic limitation in acquired-resistance lung cancer. We hypothesized that butein, a phytochemical, can overcome...

Butein induces apoptosis in human uveal melanoma cells through mitochondrial apoptosis pathway.

Curr. Eye Res. 37 , 730-739, (2012)

To study the cytotoxic effects and related signaling pathways of butein on human uveal melanoma cells in vitro.Three human uveal melanoma cell lines (M17, SP6.5, and C918), retinal pigment epithelial ...