474-07-7 Usage
Description
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 , cucurmin , and resveratrol (Item Nos. 10004235 | 70675). It also prevents remodeling of mature Aβ (1-42) fibrils. Brazilin inhibits the production of cytokines, including PGE2 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.
Uses
Different sources of media describe the Uses of 474-07-7 differently. You can refer to the following data:
1. Brazilin is a hair dyeing composition that comprises a natural dye and fatty amine.
2. inhibits platelet aggregation, PLA2, PKC, protein phosphatase, insulin receptor kinase, nitric oxide synthase, antineoplastic
3. Chiefly as a dye. Has also been recommended as indicator in acid-base titrations; acids = yellow, alkalies = carmine-red.
Definition
ChEBI: A organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood).
Purification Methods
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 474-07-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 4 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 474-07:
(5*4)+(4*7)+(3*4)+(2*0)+(1*7)=67
67 % 10 = 7
So 474-07-7 is a valid CAS Registry Number.
InChI:InChI=1/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
474-07-7Relevant articles and documents
Synthetic method of brazilin natural product (+)-Brazilin
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, (2021/03/31)
The invention relates to a synthetic method of a brazilin natural product, namely (+)-Brazilin. According to the synthetic method, a compound 3,4-dimethoxybenzyl alcohol as shown in formula 1 is usedas an initial raw material and is subjected to a nucleophilic substitution reaction, a lithium aluminum hydride reduction reaction, a Lipase PS enzyme catalyzed desymmetry reaction and a Mitsunobu reaction a Dess-Martin oxidation reaction, a one-pot-process Prins/Friedel-Crafts cascade reaction under an acidic condition, and the like so as to synthesize the natural product (+)-Brazilin. Accordingto the invention, reagents used in the method are conventional chemical reagents, reaction conditions are mild, operation is easy, a rate is relatively high, reaction byproducts are few, and synthesissteps are greatly reduced, and therefore, synthesis cost is reduced to a large extent.
Total Synthesis of (±)-Brazilin Using [4 + 1] Palladium-Catalyzed Carbenylative Annulation
Arredondo, Vanessa,Roa, Daniel E.,Gutman, Eugene S.,Huynh, Nancy O.,Van Vranken, David L.
, p. 14745 - 14759 (2019/11/13)
Palladium-catalyzed carbene insertion was utilized in a formal synthesis of (±)-picropodophyllone and a total synthesis of (±)-brazilin. All prior syntheses of brazilin have involved a Friedel-Crafts alkylation in the key carbon-carbon bond forming events. The palladium-catalyzed [4 + 1] reaction generates a 1-arylindane with all of the functionalities needed for formation of the indano[2,1-c]chroman ring system of brazilin. The synthesis of (±)-brazilin was achieved in 11 steps (longest linear sequence) with an overall 11% yield.
Formal synthesis of (±)-brazilin and total synthesis of (±)-brazilane
Yadav, Jhillu Singh,Mishra, Anand Kumar,Das, Saibal
, p. 7560 - 7566 (2014/12/10)
A convergent synthesis towards (±)-brazilin and (±)-brazilane has been reported from 3,4-dimethoxy benzaldehyde in A tetracyclic substituted indane common key intermediate is employed to furnish the desired two molecules in good to excellent yield. Pd(OH)2has played a crucial role in the total synthesis of (±)-brazilane.
