BRAZILIN CAS 474-07-7

Introduction：Basic information about BRAZILIN CAS 474-07-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

BRAZILIN Basic information

• Product Name: BRAZILIN
• Synonyms: 2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno(;6a,9,10(6h)-tetrol,7,11b-dihydro-2-d]pyran-(6as-cis)-benz[b]indeno[;7,11b-dihydrobenz(b)indeno(1,2-d)pyran-3,6a,9,10(6h)-tetrol;brasilin;braziletto;hypernicextract;limawoodextract;pernambucoextract
• CAS: 474-07-7
• MF: C16H14O5
• MW: 286.28
• EINECS: 207-477-6
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 474-07-7.mol

BRAZILIN Chemical Properties

• Melting point: 156-157℃
• Boiling point: 348.65°C (rough estimate)
• density: 1.1924 (rough estimate)
• refractive index: 1.6200 (estimate)
• storage temp.: 2-8°C
• solubility: DMSO:43.5(Max Conc. mg/mL);151.95(Max Conc. mM) DMF:30.0(Max Conc. mg/mL);104.79(Max Conc. mM) Ethanol:30.0(Max Conc. mg/mL);104.79(Max Conc. mM) PBS (pH 7.2):10.0(Max Conc. mg/mL);34.93(Max Conc. mM)
• form: A crystalline solid
• Colour Index: 75280
• color: Yellow to brown
• Optical Rotation: [α]/D 108.0 to 133.0°, c =0.5 in methanol
• 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
• InChIKey: UWHUTZOCTZJUKC-UHFFFAOYSA-N
• SMILES: C12C3C=CC(O)=CC=3OCC1(O)CC1=CC(O)=C(O)C=C21
• EPA Substance Registry System: Brazilin (474-07-7)

Safety Information

• Safety Statements: 24/25
• WGK Germany: WGK 3
• TSCA: TSCA listed
• HS Code: 29329990
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

BRAZILIN Usage And Synthesis

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.

Chemical Properties

Sourced from Sumac, family Sumacaceae.

Uses

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

Uses

Brazilin is a hair dyeing composition that comprises a natural dye and fatty amine.

Uses

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.]

References

[1] HYUNJI LEE. Brazilin Limits Inflammatory Responses through Induction of Prosurvival Autophagy in Rheumatoid Fibroblast-Like Synoviocytes.[J]. PLoS ONE, 2015: e0136122. DOI: 10.1371/journal.pone.0136122
[2] WEN-JIE DU. Brazilin inhibits amyloid β-protein fibrillogenesis, remodels amyloid fibrils and reduces amyloid cytotoxicity.[J]. Scientific Reports, 2015: 7992. DOI: 10.1038/srep07992
[3] SUPINYA TEWTRAKUL. Antiinflammatory and Wound Healing Effects of Caesalpinia sappan L.[J]. Phytotherapy Research, 2015, 29 6: 850-856. DOI: 10.1002/ptr.5321
[4] NILESH PRAKASH NIRMAL  Pharkphoom P. Antioxidant, antibacterial, and anti-inflammatory activities of standardized brazilin-rich Caesalpinia sappan extract.[J]. Pharmaceutical Biology, 2015, 53 9: 1339-1343. DOI: 10.3109/13880209.2014.982295
[5] JINHEE KIM . Inhibitory effect of brazilin on osteoclast differentiation and its mechanism of action[J]. International immunopharmacology, 2015, 29 2: Pages 628-634. DOI: 10.1016/j.intimp.2015.09.018