Brazilin

• CAT Number: R051205
• CAS Number: 474-07-7
• Molecular Formula: C16H14O5
• Molecular Weight: 286.3
• Purity: ≥95%
• Storage: -20°C
• 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
• InChIKey: UWHUTZOCTZJUKC-JKSUJKDBSA-N
• SMILES: OC(C=C1)=CC2=C1[C@](C(C=C(O)C(O)=C3)=C3C4)([H])[C@]4(O)CO2

Brazilin is an isoflavonoid originally isolated from C. sappan that has diverse biological activities, including neuroprotective, anti-inflammatory, antibacterial, and antioxidant properties. It is effective against Gram-positive and Gram-negative bacteria with MICs ranging from 31.3 to 250 μg/ml. In addition, brazilin inhibits osteoclast differentiation mediated by RANKL and is protective against LPS-induced osteoporosis in mice at a dose of 100 mg/kg.

Reference

1. Biotech Histochem. 2015;90(6):401-23. doi: 10.3109/10520295.2015.1021381. Epub
2015 Apr 20.

Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing
and folk medicine to biological staining and musical instruments.

Dapson RW(1), Bain CL.

Author information:
(1)Dapson & Dapson, LLC , Richland, Michigan.

Brazilin is a nearly colorless dye precursor obtained from the heartwood of
several species of trees including brazilwood from Brazil, sappanwood from Asia
and the Pacific islands, and to a minor extent from two other species in Central
America, northern South America and the Caribbean islands. Its use as a dyeing
agent and medicinal in Asia was recorded in the 2(nd) century BC, but was little
known in Europe until the 12(th) century AD. Asian supplies were replaced in the
16(th) century AD after the Portuguese discovered vast quantities of trees in
what is now Brazil. Overexploitation decimated the brazilwood population to the
extent that it never fully recovered. Extensive environmental efforts currently
are underway to re-create a viable, sustainable population. Brazilin is
structurally similar to the better known hematoxylin, thus is readily oxidized to
a colored dye, brazilein, which behaves like hematein. Attachment of the dye to
fabric is by hydrogen bonding or in conjunction with certain metallic mordants by
coordinative bonding. For histology, most staining procedures involve aluminum
(brazalum) for staining nuclei. In addition to textile dyeing and histological
staining, brazilin and brazilein have been and still are used extensively in
Asian folk medicine to treat a wide variety of disorders. Recent pharmacological
studies for the most part have established a scientific basis for these uses and
in many cases have elucidated the biochemical pathways involved. The principal
use of brazilwood today is for the manufacture of bows for violins and other
stringed musical instruments. The dye and other physical properties of the wood
combine to produce bows of unsurpassed tonal quality.