Butein
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MedKoo CAT#: 540053

CAS#: 487-52-5

Description: Butein is found in Rhuteic verniciflua and Butea monosperma. It induces cell cycle arrest and apoptosis in lung cancer cells, inhibits vessel spouting from aortic rings, and prevents hepatic stellate cell activation.


Chemical Structure

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Butein
CAS# 487-52-5

Theoretical Analysis

MedKoo Cat#: 540053
Name: Butein
CAS#: 487-52-5
Chemical Formula: C15H12O5
Exact Mass: 272.07
Molecular Weight: 272.250
Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

Price and Availability

Size Price Availability Quantity
5mg USD 230
10mg USD 300
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Synonym: AC1NQY7L; AC1N-QY7L; AC1N QY7L; CCG-208298; CCG208298; CCG 208298; CS-5675; CS5675; CS-5675; NSC-652892; NSC652892; NSC 652892

IUPAC/Chemical Name: (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

InChi Key: AYMYWHCQALZEGT-ORCRQEGFSA-N

InChi Code: InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

SMILES Code: O=C(C1=CC=C(O)C=C1O)/C=C/C2=CC=C(O)C(O)=C2

Appearance: Solid powder

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: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

Product Data:
Biological target: Butein is a cAMP-specific PDE inhibitor with an IC50 of 10.4 μM for PDE4.
In vitro activity: In the study, this study demonstrated the anti-proliferative effect of butein in human osteosarcoma U-2 OS cells. Data showed that butein significantly suppressed the viability and colony formation ability of U-2 OS cells. Further experiments revealed butein exposure resulted in a cell cycle arrest at S and G2/M phase in U-2 OS cells. Importantly, this study found that butein activated the tumor suppressor p53, and trigged a p53-dependent senescence in U-2 OS cells. Knockdown of p53 suppressed the senescence and rescued the viability in butein-treated U-2 OS cells. Furthermore, this study observed that butein exposure significantly enhanced reactive oxygen species (ROS) levels in U-2 OS cells. Reference: Environ Toxicol. 2021 May;36(5):773-781. https://pubmed.ncbi.nlm.nih.gov/33325610/
In vivo activity: A total of 42 mice were fasted 24 hours for the ulcer experiment, and 10, 20, and 40 mg/kg doses of butein were evaluated for their antiulcer activity. Butein administration exerted 50.8%, 65.9%, and 87.1% antiulcer effects at 10, 20, and 40 mg/kg, respectively. Butein administration decreased oxidative stress and inflammatory parameters in stomach tissues dose dependently. Reference: Eurasian J Med. 2020 Oct; 52(3): 265–270. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7651756/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 36.7 134.69
DMF 25.0 91.83
DMF:PBS (pH 7.2) (1:1) 0.5 1.84
Ethanol 37.5 137.74

Preparing Stock Solutions

The following data is based on the product molecular weight 272.25 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.

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
Formulation protocol: 1. Hsu YK, Chen HY, Wu CC, Huang YC, Hsieh CP, Su PF, Huang YF. Butein induces cellular senescence through reactive oxygen species-mediated p53 activation in osteosarcoma U-2 OS cells. Environ Toxicol. 2021 May;36(5):773-781. doi: 10.1002/tox.23079. Epub 2020 Dec 16. PMID: 33325610. 2. Abdallah BM, Ali EM. Butein Promotes Lineage Commitment of Bone Marrow-Derived Stem Cells into Osteoblasts via Modulating ERK1/2 Signaling Pathways. Molecules. 2020 Apr 18;25(8):1885. doi: 10.3390/molecules25081885. PMID: 32325749; PMCID: PMC7221720. 3. Ugan RA, Un H. The Protective Roles of Butein on Indomethacin Induced Gastric Ulcer in Mice. Eurasian J Med. 2020 Oct;52(3):265-270. doi: 10.5152/eurasianjmed.2020.20022. PMID: 33209079; PMCID: PMC7651756. 4. Farias-Pereira R, Zhang Z, Park CS, Kim D, Kim KH, Park Y. Butein inhibits lipogenesis in Caenorhabditis elegans. Biofactors. 2020 Sep;46(5):777-787. doi: 10.1002/biof.1667. Epub 2020 Jul 14. PMID: 32663368.
In vitro protocol: 1. Hsu YK, Chen HY, Wu CC, Huang YC, Hsieh CP, Su PF, Huang YF. Butein induces cellular senescence through reactive oxygen species-mediated p53 activation in osteosarcoma U-2 OS cells. Environ Toxicol. 2021 May;36(5):773-781. doi: 10.1002/tox.23079. Epub 2020 Dec 16. PMID: 33325610. 2. Abdallah BM, Ali EM. Butein Promotes Lineage Commitment of Bone Marrow-Derived Stem Cells into Osteoblasts via Modulating ERK1/2 Signaling Pathways. Molecules. 2020 Apr 18;25(8):1885. doi: 10.3390/molecules25081885. PMID: 32325749; PMCID: PMC7221720.
In vivo protocol: 1. Ugan RA, Un H. The Protective Roles of Butein on Indomethacin Induced Gastric Ulcer in Mice. Eurasian J Med. 2020 Oct;52(3):265-270. doi: 10.5152/eurasianjmed.2020.20022. PMID: 33209079; PMCID: PMC7651756. 2. Farias-Pereira R, Zhang Z, Park CS, Kim D, Kim KH, Park Y. Butein inhibits lipogenesis in Caenorhabditis elegans. Biofactors. 2020 Sep;46(5):777-787. doi: 10.1002/biof.1667. Epub 2020 Jul 14. PMID: 32663368.

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1: Wang Z, Ka SO, Lee Y, Park BH, Bae EJ. Butein induction of HO-1 by p38 MAPK/Nrf2 pathway in adipocytes attenuates high-fat diet induced adipose hypertrophy in mice. Eur J Pharmacol. 2017 Mar 15;799:201-210. doi: 10.1016/j.ejphar.2017.02.021. Epub 2017 Feb 14. PubMed PMID: 28213287.

2: Zheng W, Zhang H, Jin Y, Wang Q, Chen L, Feng Z, Chen H, Wu Y. Butein inhibits IL-1β-induced inflammatory response in human osteoarthritis chondrocytes and slows the progression of osteoarthritis in mice. Int Immunopharmacol. 2017 Jan;42:1-10. doi: 10.1016/j.intimp.2016.11.009. Epub 2016 Nov 15. PubMed PMID: 27863298.

3: Choi HS, Kim MK, Choi YK, Shin YC, Cho SG, Ko SG. 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 Apr 27;16:122. doi: 10.1186/s12906-016-1103-3. PubMed PMID: 27121110; PubMed Central PMCID: PMC4848824.

4: Tang YL, Huang LB, Lin WH, Wang LN, Tian Y, Shi D, Wang J, Qin G, Li A, Liang YN, Zhou HJ, Ke ZY, Huang W, Deng W, Luo XQ. 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. doi: 10.18632/oncotarget.7624. PubMed PMID: 26919107; PubMed Central PMCID: PMC4951317.

5: Padmavathi G, Rathnakaram SR, Monisha J, Bordoloi D, Roy NK, Kunnumakkara AB. Potential of butein, a tetrahydroxychalcone to obliterate cancer. Phytomedicine. 2015 Dec 1;22(13):1163-71. doi: 10.1016/j.phymed.2015.08.015. Epub 2015 Oct 13. Review. PubMed PMID: 26598915.

6: Toprak M. Fluorescence study on the interaction of human serum albumin with Butein in liposomes. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Feb 5;154:108-13. doi: 10.1016/j.saa.2015.10.023. Epub 2015 Oct 24. Review. Erratum in: Spectrochim Acta A Mol Biomol Spectrosc. 2016 Mar 15;157:271. PubMed PMID: 26519918.

7: Kojima R, Kawachi M, Ito M. Butein suppresses ICAM-1 expression through the inhibition of IκBα and c-Jun phosphorylation in TNF-α- and PMA-treated HUVECs. Int Immunopharmacol. 2015 Feb;24(2):267-75. doi: 10.1016/j.intimp.2014.12.016. Epub 2014 Dec 19. PubMed PMID: 25533502.

8: Sung J, Lee J. Anti-Inflammatory Activity of Butein and Luteolin Through Suppression of NFκB Activation and Induction of Heme Oxygenase-1. J Med Food. 2015 May;18(5):557-64. doi: 10.1089/jmf.2014.3262. Epub 2015 Feb 18. PubMed PMID: 25692285.

9: Yang PY, Hu DN, Lin IC, Liu FS. Butein Shows Cytotoxic Effects and Induces Apoptosis in Human Ovarian Cancer Cells. Am J Chin Med. 2015;43(4):769-82. doi: 10.1142/S0192415X15500482. Epub 2015 Jun 28. PubMed PMID: 26119952.

10: Lee SD, Choe JW, Lee BJ, Kang MH, Joo MK, Kim JH, Yeon JE, Park JJ, Kim JS, Bak YT. Butein effects in colitis and interleukin-6/signal transducer and activator of transcription 3 expression. World J Gastroenterol. 2015 Jan 14;21(2):465-74. doi: 10.3748/wjg.v21.i2.465. PubMed PMID: 25593461; PubMed Central PMCID: PMC4292277.

11: Lai YW, Wang SW, Chang CH, Liu SC, Chen YJ, Chi CW, Chiu LP, Chen SS, Chiu AW, Chung CH. Butein inhibits metastatic behavior in mouse melanoma cells through VEGF expression and translation-dependent signaling pathway regulation. BMC Complement Altern Med. 2015 Dec 22;15:445. doi: 10.1186/s12906-015-0970-3. PubMed PMID: 26694191; PubMed Central PMCID: PMC4687249.

12: Jung SK, Lee MH, Lim DY, Lee SY, Jeong CH, Kim JE, Lim TG, Chen H, Bode AM, Lee HJ, Lee KW, Dong Z. Butein, a novel dual inhibitor of MET and EGFR, overcomes gefitinib-resistant lung cancer growth. Mol Carcinog. 2015 Apr;54(4):322-31. doi: 10.1002/mc.22191. Epub 2014 Jun 29. PubMed PMID: 24974831.

13: Zhang L, Yang X, Li X, Li C, Zhao L, Zhou Y, Hou H. 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. doi: 10.3892/ijmm.2015.2324. Epub 2015 Aug 24. PubMed PMID: 26310353; PubMed Central PMCID: PMC4564095.

14: Liu SC, Chen C, Chung CH, Wang PC, Wu NL, Cheng JK, Lai YW, Sun HL, Peng CY, Tang CH, Wang SW. Inhibitory effects of butein on cancer metastasis and bioenergetic modulation. J Agric Food Chem. 2014 Sep 17;62(37):9109-17. doi: 10.1021/jf502370c. Epub 2014 Sep 3. PubMed PMID: 25137351.

15: Wang Z, Lee Y, Eun JS, Bae EJ. Inhibition of adipocyte inflammation and macrophage chemotaxis by butein. Eur J Pharmacol. 2014 Sep 5;738:40-8. doi: 10.1016/j.ejphar.2014.05.031. Epub 2014 May 27. PubMed PMID: 24877688.

16: Padmavathi G, Roy NK, Bordoloi D, Arfuso F, Mishra S, Sethi G, Bishayee A, Kunnumakkara AB. Butein in health and disease: A comprehensive review. Phytomedicine. 2017 Feb 15;25:118-127. doi: 10.1016/j.phymed.2016.12.002. Epub 2016 Dec 12. Review. PubMed PMID: 28190465.

17: Seo WY, Youn GS, Choi SY, Park J. Butein, a tetrahydroxychalcone, suppresses pro-inflammatory responses in HaCaT keratinocytes. BMB Rep. 2015 Sep;48(9):495-500. PubMed PMID: 25541056; PubMed Central PMCID: PMC4641232.

18: Huang YT, Lin CI, Chien PH, Tang TT, Lin J, Chao JI. The depletion of securin enhances butein-induced apoptosis and tumor inhibition in human colorectal cancer. Chem Biol Interact. 2014 Sep 5;220:41-50. doi: 10.1016/j.cbi.2014.06.006. Epub 2014 Jun 12. PubMed PMID: 24931875.

19: Bai X, Ma Y, Zhang G. Butein suppresses cervical cancer growth through the PI3K/AKT/mTOR pathway. Oncol Rep. 2015 Jun;33(6):3085-92. doi: 10.3892/or.2015.3922. Epub 2015 Apr 24. PubMed PMID: 25962638.

20: Lee DS, Jeong GS. Butein provides neuroprotective and anti-neuroinflammatory effects through Nrf2/ARE-dependent haem oxygenase 1 expression by activating the PI3K/Akt pathway. Br J Pharmacol. 2016 Oct;173(19):2894-909. doi: 10.1111/bph.13569. Epub 2016 Aug 31. PubMed PMID: 27465039; PubMed Central PMCID: PMC5055139.