474-07-7 Usage
Description
Brazilin is an isoflavonoid originally isolated from Caesalpinia sappan, a plant commonly known as sappan wood. It is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood). Brazilin exhibits diverse biological activities, including neuroprotective, anti-inflammatory, antibacterial, and antioxidant properties. It is known for its potent inhibition of Aβ (1-42) fibrillogenesis and its ability to prevent the remodeling of mature Aβ (1-42) fibrils. Additionally, Brazilin inhibits the production of cytokines, such as PGE2 and TNF-α, and demonstrates effectiveness against both Gram-positive and Gram-negative bacteria.
Uses
1. Used in Hair Dye Industry:
Brazilin is used as a natural dye in hair dyeing compositions, providing a safe and eco-friendly alternative to synthetic dyes.
2. Used in Pharmaceutical Industry:
Brazilin is used as an inhibitor for various biological processes, including platelet aggregation, PLA2, PKC, protein phosphatase, insulin receptor kinase, and nitric oxide synthase. It also exhibits antineoplastic properties, making it a potential candidate for cancer treatment.
3. Used in Acid-Base Titrations:
Brazilin has been recommended as an indicator in acid-base titrations, where it changes color depending on the pH level. In acidic conditions, it appears yellow, and in alkaline conditions, it turns carmine-red.
4. Used in Antimicrobial Applications:
Due to its antibacterial properties, Brazilin is effective against both Gram-positive and Gram-negative bacteria, with minimum inhibitory concentrations (MICs) ranging from 31.3 to 250 μg/ml.
5. Used in Neuroprotection:
Brazilin's neuroprotective properties make it a potential candidate for the treatment of neurodegenerative diseases, as it inhibits Aβ (1-42) fibrillogenesis and prevents the remodeling of mature Aβ (1-42) fibrils.
6. Used in Anti-Inflammatory Applications:
Brazilin's anti-inflammatory properties, demonstrated by its inhibition of cytokine production, make it a potential candidate for the treatment of inflammatory conditions.
7. Used in Osteoporosis Treatment:
Brazilin inhibits osteoclast differentiation mediated by RANKL and is protective against LPS-induced osteoporosis in mice at a dose of 100 mg/kg, making it a potential candidate for osteoporosis treatment.
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.
Enantioselective syntheses of (+)- and (-)-brazilin
Javed, Umair,Karim, Moinul,Jahng, Katherine C.,Park, Jae-Gyu,Jahng, Yurngdong
, p. 1270 - 1274 (2015/02/02)
Two enantiomers of brazilin were prepared in 9 steps from 7-hydroxychroman-4-one using the AD-mix-α and AD-mix-β-directed enantioselective dihydroxylation of 3-(4-hydroxy-3-methoxyphenyl)-2H-chromen-7-ol as a key step.
