474-07-7

inhibits platelet aggregation, PLA2, PKC, protein phosphatase, insulin receptor kinase, nitric oxide synthase, antineoplastic

ChEBI: A organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood).

Chiefly as a dye. Has also been recommended as indicator in acid-base titrations; acids = yellow, alkalies = carmine-red.

Brazilin is an isoflavonoid originally isolated from C. sappan that has diverse biological activities, including neuroprotective, anti-inflammatory, antibacterial, and antioxidant properties. Brazilin inhibits Aβ (1-42) fibrillogenesis (IC₅₀ = 1.5 μM) more potently than (-)-epigallocatechin gallate (Item No. 70935), cucurmin (Item No. 81025), and resveratrol (Item Nos. 10004235 | 70675). It also prevents remodeling of mature Aβ (1-42) fibrils. Brazilin inhibits the production of cytokines, including PGE₂ (Item No. 14010) and TNF-α (IC₅₀s = 12.6 and 87.2 μM). 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.

Brazilin crystallises from EtOH as yellow crystals which become orange when exposed to light and air, and is yellow in dilute acid but crimson in dilute alkali. When crystallised from H2O, it has m 247-248o. It forms coloured metal salts and is oxidized in air to Brazilein the quinonoid form. The (±)-form has been resolved, and the (+)-enantiomer has [] 20 +121o (c 1, MeOH). [Craig et al. J Org Chem 30 1573 1965,Morsingh & Robinson Tetrahedron 26 281 1970, Beilstein 17 H 194, 17 II 244, 17 III/IV 2711.]