Brazilein | CAS#600-76-0 | immune suppressive

MedKoo Cat#: 471177 | Name: Brazilein

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Description:

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

Brazilein is a natural small molecule isolated from dried heartwood, exhibiting multi-pharmacological activities. Brazilein is reported to have immunosuppressive effect on cardiovascular and cerebral-vascular diseases.

Chemical Structure

Brazilein

CAS#600-76-0

Theoretical Analysis

MedKoo Cat#: 471177

Name: Brazilein

CAS#: 600-76-0

Chemical Formula: C16H12O5

Exact Mass: 284.0680

Molecular Weight: 284.27

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

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Brazilein

IUPAC/Chemical Name

3,6a,10-trihydroxy-6a,7-dihydroindeno[2,1-c]chromen-9(6H)-one

InChi Key

MLWIYODOURBGPI-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H12O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,17,19-20H,6-7H2

SMILES Code

O=C1C=C2C(C=C1O)=C3C4=C(C=C(C=C4)O)OCC3(O)C2

Appearance

Solid powder

Purity

>95% (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: Ngamwonglumlert L, Devahastin S. Brazilein as an alternative pigment: Isolation, characterization, stability enhancement and food applications. Food Chem. 2023 Jan 1;398:133898. doi: 10.1016/j.foodchem.2022.133898. Epub 2022 Aug 9. PMID: 35969994. 2: Handayani S, Susidarti RA, Utomo RY, Meiyanto E, Jenie RII. Synergistic Cytotoxic and Antimigratory Effect of Brazilein and Doxorubicin on HER2-Overexpressing Cells. Asian Pac J Cancer Prev. 2022 Aug 1;23(8):2623-2632. doi: 10.31557/APJCP.2022.23.8.2623. PMID: 36037115; PMCID: PMC9741888. 3: Kim KJ, Yoon KY, Yoon HS, Oh SR, Lee BY. Brazilein Suppresses Inflammation through Inactivation of IRAK4-NF-κB Pathway in LPS-Induced Raw264.7 Macrophage Cells. Int J Mol Sci. 2015 Nov 18;16(11):27589-98. doi: 10.3390/ijms161126048. PMID: 26593910; PMCID: PMC4661906. 4: Yan XJ, Chai YS, Yuan ZY, Wang XP, Jiang JF, Lei F, Xing DM, DU LJ. Brazilein inhibits neuronal inflammation induced by cerebral ischemia and oxygen-glucose deprivation through targeting NOD2 expression. Chin J Nat Med. 2016 May;14(5):354-62. doi: 10.3724/SP.J.1009.2016.00354. PMID: 27478098. 5: Mou Z, Wang Y, Li Y. Retraction notice to "Brazilein induces apoptosis and G1/G0 phase cell cycle arrest by up-regulation of miR-133a in human vestibular schwannoma cells" [Experimental and Molecular Pathology 107 (2019) 95-101]. Exp Mol Pathol. 2022 Aug;127:104782. doi: 10.1016/j.yexmp.2022.104782. Epub 2022 Jun 27. PMID: 35773064. 6: Hsieh CY, Tsai PC, Chu CL, Chang FR, Chang LS, Wu YC, Lin SR. Brazilein suppresses migration and invasion of MDA-MB-231 breast cancer cells. Chem Biol Interact. 2013 Jul 5;204(2):105-15. doi: 10.1016/j.cbi.2013.05.005. Epub 2013 May 21. PMID: 23707804. 7: He W, Fan Q, Zhou L, Huang F, Jiang X, Na Z, Hu H, Song Q. [Preparation of brazilein from Caesalpinia sappan by high performance countercurrent chromatography]. Se Pu. 2020 Dec 8;38(12):1363-1368. Chinese. doi: 10.3724/SP.J.1123.2020.03016. PMID: 34213250. 8: Tao LY, Li JY, Zhang JY. Brazilein, a compound isolated from Caesalpinia sappan Linn., induced growth inhibition in breast cancer cells via involvement of GSK-3β/β-Catenin/cyclin D1 pathway. Chem Biol Interact. 2013 Oct 25;206(1):1-5. doi: 10.1016/j.cbi.2013.07.015. Epub 2013 Aug 13. PMID: 23948132. 9: Mou Z, Wang Y, Li Y. Brazilein induces apoptosis and G1/G0 phase cell cycle arrest by up-regulation of miR-133a in human vestibular schwannoma cells. Exp Mol Pathol. 2019 Apr;107:95-101. doi: 10.1016/j.yexmp.2018.12.010. Epub 2019 Jan 2. Retraction in: Exp Mol Pathol. 2022 Aug;127:104782. PMID: 30610843. 10: Wudtiwai B, Kodchakorn K, Shwe TH, Pothacharoen P, Phitak T, Suninthaboonrana R, Kongtawelert P. Brazilein inhibits epithelial-mesenchymal transition (EMT) and programmed death ligand 1 (PD-L1) expression in breast cancer cells. Int Immunopharmacol. 2023 May;118:109988. doi: 10.1016/j.intimp.2023.109988. Epub 2023 Mar 16. PMID: 36933493. 11: Jian C, Zhang L, Jinlong L, Bo T, Liu Z. Effects of brazilein on PSD-95 protein expression and neurological recovery in mice after sciatic nerve injury. Neurosci Lett. 2020 Jan 10;715:134547. doi: 10.1016/j.neulet.2019.134547. Epub 2019 Oct 17. PMID: 31629776. 12: Kurniawan E, Krihariyani D. Working goal of Brazilein sappan wood as a candidate for SARS-coV-2 antivirus drug against spike (S) glycoprotein, papain- like proteinase, and main protease: In silico study. J Adv Pharm Technol Res. 2021 Jul-Sep;12(3):298-304. doi: 10.4103/japtr.JAPTR_222_21. Epub 2021 Jul 16. PMID: 34345611; PMCID: PMC8300323. 13: Yuan ZY, Lei F, Chai YS, Wu H, Zhao S, Wang YG, Feng TS, Li HY, Li HY, Zhan HL, Xing DM, DU LJ. Reproductive toxicity of brazilein in ICR mice. Chin J Nat Med. 2016 Jun;14(6):441-8. doi: 10.1016/S1875-5364(16)30041-3. PMID: 27473962. 14: Shen J, Yip S, Wang Z, Wang W, Xing D, Du L. Brazilein-induced contraction of rat arterial smooth muscle involves activation of Ca2+ entry and ROK, ERK pathways. Eur J Pharmacol. 2008 Feb 12;580(3):366-71. doi: 10.1016/j.ejphar.2007.11.012. Epub 2007 Nov 17. PMID: 18177858. 15: Ye M, Xie WD, Lei F, Meng Z, Zhao YN, Su H, Du LJ. Brazilein, an important immunosuppressive component from Caesalpinia sappan L. Int Immunopharmacol. 2006 Mar;6(3):426-32. doi: 10.1016/j.intimp.2005.09.012. Epub 2005 Oct 17. PMID: 16428078. 16: Zhong X, Wu B, Pan YJ, Zheng S. Brazilein inhibits survivin protein and mRNA expression and induces apoptosis in hepatocellular carcinoma HepG2 cells. Neoplasma. 2009;56(5):387-92. doi: 10.4149/neo_2009_05_387. PMID: 19580339. 17: Shen J, Zhang H, Lin H, Su H, Xing D, Du L. Brazilein protects the brain against focal cerebral ischemia reperfusion injury correlating to inflammatory response suppression. Eur J Pharmacol. 2007 Mar 8;558(1-3):88-95. doi: 10.1016/j.ejphar.2006.11.059. Epub 2006 Dec 6. PMID: 17239368. 18: Dapson RW, Bain CL. Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing and folk medicine to biological staining and musical instruments. Biotech Histochem. 2015;90(6):401-23. doi: 10.3109/10520295.2015.1021381. Epub 2015 Apr 20. PMID: 25893688. 19: Liang CH, Chan LP, Chou TH, Chiang FY, Yen CM, Chen PJ, Ding HY, Lin RJ. Brazilein from Caesalpinia sappan L. Antioxidant Inhibits Adipocyte Differentiation and Induces Apoptosis through Caspase-3 Activity and Anthelmintic Activities against Hymenolepis nana and Anisakis simplex. Evid Based Complement Alternat Med. 2013;2013:864892. doi: 10.1155/2013/864892. Epub 2013 Mar 11. PMID: 23554834; PMCID: PMC3608347. 20: Ngamwonglumlert L, Devahastin S, Chiewchan N, Raghavan GSV. Color and molecular structure alterations of brazilein extracted from Caesalpinia sappan L. under different pH and heating conditions. Sci Rep. 2020 Jul 24;10(1):12386. doi: 10.1038/s41598-020-69189-3. PMID: 32709964; PMCID: PMC7382456.