Brazilin | CAS#474-07-7 | histone deacetylase inactivator

MedKoo Cat#: 525409 | Name: Brazilin

Description:

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

Brazilin is an inducer of apoptosis and G2/M arrest via inactivation of histone deacetylase, inhibiting prostatic acidic phosphatase fibrillogenesis and reducing its cytotoxicity.

Chemical Structure

Brazilin

CAS#474-07-7

Theoretical Analysis

MedKoo Cat#: 525409

Name: Brazilin

CAS#: 474-07-7

Chemical Formula: C16H14O5

Exact Mass: 286.0841

Molecular Weight: 286.28

Elemental Analysis: C, 67.13; H, 4.93; O, 27.94

Price and Availability

Size	Price	Availability
200mg	USD 1,650.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,650.00	2 Weeks
2g	USD 5,950.00	2 Weeks
5g	USD 9,650.00	2 Weeks

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Related CAS #

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Synonym

Brazilin

IUPAC/Chemical Name

(6aS,11bR)-7,11b-Dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol

InChi Key

UWHUTZOCTZJUKC-JKSUJKDBSA-N

InChi Code

InChI=1S/C16H14O5/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/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1

SMILES Code

OC1=CC2=C(C=C1)[C@]3([H])[C@](CC4=C3C=C(O)C(O)=C4)(O)CO2

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

Product Data

Instruction

View handling instruction

Biological target:

Brazilin inhibits the cells proliferation, promotes apoptosis, and induces autophagy through the AMPK/mTOR pathway.

In vitro activity:

Brazilin treatment prevented the induction of ThT positive aggregates. Control brain homogenates from control corticobasal degeneration (CBD) patients did not induce ThT fluorescence. Imaging by TEM confirmed that Brazilin treatment prevented the formation of fibrillar α-syn aggregates in RT-QuIC (Figure 7b). Reference: J Mol Biol. 2021 Apr 16; 433(8): 166878. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7610480/

In vivo activity:

In OFT, CMS mice spent less time in the central zone (F1,19 = 13.296, p < 0.005, Fig. 4B) compared with naïve mice. The brazilin (3 mg/kg) treatment increased the time spent in the central zone in the OFT (F3,35 = 2.052, p < 0.05, Fig. 4B) compared to the mice in CMS + VEH group. Reference: Biol Pharm Bull. 2019;42(8):1268-1274. https://www.jstage.jst.go.jp/article/bpb/42/8/42_b18-00882/_article

	Solvent	mg/mL	mM
Solubility
	DMSO	43.5	151.95
	DMF	30.0	104.79
	Ethanol	30.0	104.79
	PBS (pH 7.2)	10.0	34.93

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 286.28 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

Formulation protocol:

1. Hermawan A, Putri H. Integrative Bioinformatics Analysis Reveals Potential Target Genes and TNFα Signaling Inhibition by Brazilin in Metastatic Breast Cancer Cells. Asian Pac J Cancer Prev. 2020 Sep 1;21(9):2751-2762. doi: 10.31557/APJCP.2020.21.9.2751. PMID: 32986377; PMCID: PMC7779440. 2. Qi B, Zhang X, Yu H, Bao Y, Wu N, Jia D. Brazilin prevents against myocardial ischemia-reperfusion injury through the modulation of Nrf2 via the PKC signaling pathway. Ann Transl Med. 2021 Feb;9(4):312. doi: 10.21037/atm-20-4414. PMID: 33708939; PMCID: PMC7944319. 3. Wang X, Xiu Z, Du Y, Li Y, Yang J, Gao Y, Li F, Yin X, Shi H. Brazilin Treatment Produces Antidepressant- and Anxiolytic-Like Effects in Mice. Biol Pharm Bull. 2019;42(8):1268-1274. doi: 10.1248/bpb.b18-00882. PMID: 31366864. 4. Li ZY, Zheng Y, Chen Y, Pan M, Zheng SB, Huang W, Zhou ZH, Ye HY. Brazilin Ameliorates Diabetic Nephropathy and Inflammation in db/db Mice. Inflammation. 2017 Aug;40(4):1365-1374. doi: 10.1007/s10753-017-0579-4. PMID: 28497277.

In vitro protocol:

In vivo protocol:

1. Wang X, Xiu Z, Du Y, Li Y, Yang J, Gao Y, Li F, Yin X, Shi H. Brazilin Treatment Produces Antidepressant- and Anxiolytic-Like Effects in Mice. Biol Pharm Bull. 2019;42(8):1268-1274. doi: 10.1248/bpb.b18-00882. PMID: 31366864. 2. Li ZY, Zheng Y, Chen Y, Pan M, Zheng SB, Huang W, Zhou ZH, Ye HY. Brazilin Ameliorates Diabetic Nephropathy and Inflammation in db/db Mice. Inflammation. 2017 Aug;40(4):1365-1374. doi: 10.1007/s10753-017-0579-4. PMID: 28497277.

1: Li ZY, Zheng Y, Chen Y, Pan M, Zheng SB, Huang W, Zhou ZH, Ye HY. Brazilin Ameliorates Diabetic Nephropathy and Inflammation in db/db Mice. Inflammation. 2017 May 11. doi: 10.1007/s10753-017-0579-4. [Epub ahead of print] PubMed PMID: 28497277. 2: Li M, Dong X, Liu Y, Sun Y. Brazilin Inhibits Prostatic Acidic Phosphatase Fibrillogenesis and Decreases its Cytotoxicity. Chem Asian J. 2017 Mar 16. doi: 10.1002/asia.201700058. [Epub ahead of print] PubMed PMID: 28303660. 3: Gogoi D, Devi R, Pahari P, Sarma B, Das SK. cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin. Beilstein J Org Chem. 2016 Dec 21;12:2816-2822. doi: 10.3762/bjoc.12.280. eCollection 2016. PubMed PMID: 28144354; PubMed Central PMCID: PMC5238543. 4: He ZJ, Zhu FY, Li SS, Zhong L, Tan HY, Wang K. Inhibiting ROS-NF-κB-dependent autophagy enhanced brazilin-induced apoptosis in head and neck squamous cell carcinoma. Food Chem Toxicol. 2017 Mar;101:55-66. doi: 10.1016/j.fct.2017.01.002. Epub 2017 Jan 4. PubMed PMID: 28063998. 5: Kang K, Won M, Yuk JM, Park CY, Byun HS, Park KA, Lee SR, Kang YG, Shen HM, Lee IY, Hur GM. IinQ attenuates systemic inflammatory responses via selectively impairing the Myddosome complex formation upon TLR4 ligation. Biochem Pharmacol. 2016 Dec 1;121:52-66. doi: 10.1016/j.bcp.2016.09.017. Epub 2016 Sep 21. PubMed PMID: 27664853. 6: García-Heredia A, García S, Merino-Mascorro JÁ, Feng P, Heredia N. Natural plant products inhibits growth and alters the swarming motility, biofilm formation, and expression of virulence genes in enteroaggregative and enterohemorrhagic Escherichia coli. Food Microbiol. 2016 Oct;59:124-32. doi: 10.1016/j.fm.2016.06.001. Epub 2016 Jun 4. PubMed PMID: 27375253. 7: Jia Y, Zhao J, Liu M, Li B, Song Y, Li Y, Wen A, Shi L. Brazilin exerts protective effects against renal ischemia-reperfusion injury by inhibiting the NF-κB signaling pathway. Int J Mol Med. 2016 Jul;38(1):210-6. doi: 10.3892/ijmm.2016.2616. Epub 2016 May 31. PubMed PMID: 27247107; PubMed Central PMCID: PMC4899020. 8: Siriangkhawut W, Khanhuathon Y, Chantiratikul P, Ponhong K, Grudpan K. A Green Sequential Injection Spectrophotometric Approach Using Natural Reagent Extracts from Heartwood of Ceasalpinia sappan Linn. for Determination of Aluminium. Anal Sci. 2016;32(3):329-36. doi: 10.2116/analsci.32.329. PubMed PMID: 26960614. 9: Mueller M, Weinmann D, Toegel S, Holzer W, Unger FM, Viernstein H. Compounds from Caesalpinia sappan with anti-inflammatory properties in macrophages and chondrocytes. Food Funct. 2016 Mar;7(3):1671-9. doi: 10.1039/c5fo01256b. PubMed PMID: 26951869. 10: Yan Y, Chen YC, Lin YH, Guo J, Niu ZR, Li L, Wang SB, Fang LH, Du GH. Brazilin isolated from the heartwood of Caesalpinia sappan L induces endothelium-dependent and -independent relaxation of rat aortic rings. Acta Pharmacol Sin. 2015 Nov;36(11):1318-26. doi: 10.1038/aps.2015.113. Epub 2015 Oct 12. PubMed PMID: 26564314; PubMed Central PMCID: PMC4644902. 11: Kim J, Lee HK, Chang TS, Kang KS, Hwang GS. Inhibitory effect of brazilin on osteoclast differentiation and its mechanism of action. Int Immunopharmacol. 2015 Dec;29(2):628-34. doi: 10.1016/j.intimp.2015.09.018. Epub 2015 Oct 1. PubMed PMID: 26428849. 12: Lee H, Kang SW, Byun HS, Jeon J, Park KA, Kang K, Seo W, Won M, Seok JH, Han MD, Shen HM, Hur GM. Brazilin Limits Inflammatory Responses through Induction of Prosurvival Autophagy in Rheumatoid Fibroblast-Like Synoviocytes. PLoS One. 2015 Aug 21;10(8):e0136122. doi: 10.1371/journal.pone.0136122. eCollection 2015. PubMed PMID: 26295477; PubMed Central PMCID: PMC4546660. 13: Nirmal NP, Rajput MS, Prasad RG, Ahmad M. Brazilin from Caesalpinia sappan heartwood and its pharmacological activities: A review. Asian Pac J Trop Med. 2015 Jun;8(6):421-30. doi: 10.1016/j.apjtm.2015.05.014. Epub 2015 Jun 25. PubMed PMID: 26194825. 14: Xu YY, Yin J. Contact dermatitis caused by brazilin in Caesalpinia sappan. Contact Dermatitis. 2015 Sep;73(3):189-90. doi: 10.1111/cod.12412. Epub 2015 May 11. PubMed PMID: 25960163. 15: Gao XJ, Wang TC, Zhang ZC, Cao YG, Zhang NS, Guo MY. Brazilin plays an anti-inflammatory role with regulating Toll-like receptor 2 and TLR 2 downstream pathways in Staphylococcus aureus-induced mastitis in mice. Int Immunopharmacol. 2015 Jul;27(1):130-7. doi: 10.1016/j.intimp.2015.04.043. Epub 2015 May 2. PubMed PMID: 25939535. 16: Jung EG, Han KI, Hwang SG, Kwon HJ, Patnaik BB, Kim YH, Han MD. Brazilin isolated from Caesalpinia sappan L. inhibits rheumatoid arthritis activity in a type-II collagen induced arthritis mouse model. BMC Complement Altern Med. 2015 Apr 22;15:124. doi: 10.1186/s12906-015-0648-x. PubMed PMID: 25896410; PubMed Central PMCID: PMC4410491. 17: 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. Review. PubMed PMID: 25893688. 18: Zhang T, Fan X, Song L, Ren L, Ma E, Zhang S, Ren L, Zheng Y, Zhang J. c-Fos is involved in inhibition of human bladder carcinoma T24 cells by brazilin. IUBMB Life. 2015 Mar;67(3):175-81. doi: 10.1002/iub.1357. Epub 2015 Apr 11. PubMed PMID: 25865820. 19: Nirmal NP, Panichayupakaranant P. Antioxidant, antibacterial, and anti-inflammatory activities of standardized brazilin-rich Caesalpinia sappan extract. Pharm Biol. 2015;53(9):1339-43. doi: 10.3109/13880209.2014.982295. Epub 2015 Apr 13. PubMed PMID: 25864864. 20: Subba Reddy BV, Prudhvi Raju N, Someswarao B, Mohan Reddy BJ, Sridhar B, Marumudi K, Kunwar AC. A novel domino cyclization for the stereoselective synthesis of indeno[2,1-c]pyran and cyclopenta[c]pyran derivatives. Org Biomol Chem. 2015 Apr 28;13(16):4733-6. doi: 10.1039/c5ob00376h. PubMed PMID: 25804904.