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BRAZILIN

CAS No.:
474-07-7
Catalog Number:
AG00DC0C
Molecular Formula:
C16H14O5
Molecular Weight:
286.2794
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Product Description
Catalog Number:
AG00DC0C
Chemical Name:
BRAZILIN
CAS Number:
474-07-7
Molecular Formula:
C16H14O5
Molecular Weight:
286.2794
MDL Number:
MFCD00210817
IUPAC Name:
(6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol
InChI:
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
InChI Key:
UWHUTZOCTZJUKC-JKSUJKDBSA-N
SMILES:
Oc1ccc2c(c1)OC[C@]1([C@@H]2c2cc(O)c(cc2C1)O)O
EC Number:
207-477-6
UNII:
FZ39SW1K10
Properties
Complexity:
416  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
286.084g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
286.283g/mol
Monoisotopic Mass:
286.084g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
90.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.5  
Literature
Title Journal
Inhibiting ROS-NF-κB-dependent autophagy enhanced brazilin-induced apoptosis in head and neck squamous cell carcinoma. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20170301
Antiallergic asthma properties of brazilin through inhibition of TH2 responses in T cells and in a murine model of asthma. Journal of agricultural and food chemistry 20120919
Separation of four homoisoflavonoids from Caesalpinia sappan by high-speed counter-current chromatography. Phytochemical analysis : PCA 20120101
Using the pER8:GUS reporter system to screen for phytoestrogens from Caesalpinia sappan. Journal of natural products 20110826
Vasorelaxant activity of Sappan Lignum constituents and extracts on rat aorta and mesenteric artery. Biological & pharmaceutical bulletin 20100101
Heme oxygenase-1 mediates the inhibitory actions of brazilin in RAW264.7 macrophages stimulated with lipopolysaccharide. Journal of ethnopharmacology 20090112
In vitro study for inhibition of NO production about constituents of Sappan Lignum. Biological & pharmaceutical bulletin 20070101
Brazilin and the extract from Caesalpinia sappan L. protect oxidative injury through the expression of heme oxygenase-1. BioFactors (Oxford, England) 20070101
Synthesis of (+/-)-brazilin using IBX. Organic letters 20051222
Effects of brazilin on the production of fructose-2,6-bisphosphate in rat hepatocytes. Journal of ethnopharmacology 20051031
Suppression of lipopolysaccharide-induced expression of inducible nitric oxide synthase by brazilin in RAW 264.7 macrophage cells. European journal of pharmacology 20050425
Antiplatelet activity of BRX-018, (6aS,cis)-malonic acid 3-acetoxy-6a9-bis-(2-methoxycarbonyl-acetoxy)-6,6a,7,11b-tetrahydro-indeno[2,1-c]chromen-10-yl ester methylester. Thrombosis research 20050101
Effects of Brx-019 (acetic acid 3,6a,9-triacetoxy-6,6a,7, 11b-tetrahydro-indeno [2,1-c] chromen-10-yl ester), a Brazilin derivative, on T cell-mediated immune responses in multiple low dose streptozotocin-induced diabetic C57BL/6 male mice. Arzneimittel-Forschung 20050101
Mechanism of action of Brazilin on gluconeogenesis in isolated rat hepatocytes. Planta medica 20040801
The antibacterial principle of Caesalpina sappan. Phytotherapy research : PTR 20040801
Induction of vasorelaxation through activation of nitric oxide synthase in endothelial cells by brazilin. European journal of pharmacology 20030502
A DNA strand-nicking principle of a higher plant, Caesalpinia sappan. Archives of pharmacal research 20030201
Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore. Antiviral chemistry & chemotherapy 19981101
Inhibition of human immunodeficiency virus integrase by bis-catechols. Antimicrobial agents and chemotherapy 19950201
Properties