(+)-brazilin

Names

[ CAS No. ]:
474-07-7

[ Name ]:
(+)-brazilin

[Synonym ]:
(6aS-cis)-7,11b-Dihydrobenz[b]indeno[1,2-d]pyran-3,6a,9,10(6H)-tetrol
superbresiline
pernambucoextract
(+)-brazilin
Benz[b]indeno[1,2-d]pyran-3,6a,9,10(6H)-tetrol, 7,11b-dihydro-, (6aS,11bR)-
(6aS,11bR)-7,11b-Dihydroindeno[2,1-c]chromene-3,6a,9,10(6H)-tetrol
braziletto
C.I. Natural Red 24
hypernicextract
limawoodextract
BRAZILIN
brasilin

Biological Activity

[Description]:

Brazilin is a red dye precursor obtained from the heartwood of several species of tropical hardwoods. Brazilin inhibits the cells proliferation, promotes apoptosis, and induces autophagy through the AMPK/mTOR pathway. Brazilin shows chondroprotective and anti-inflammatory activities[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

[References]

[1]. Dapson RW, et al. Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing and folk medicine to biological staining and musical instruments. Biotech Histochem. 2015;90(6):401-23.

[2]. Jia Y, et al. [Effect of brazilin on apoptosis and autophagy of tongue cancer Tca8113 cells and its molecular mechanism]. Nan Fang Yi Ke Da Xue Xue Bao. 2019 Mar 30;39(3):351-356.

[3]. Weinmann D, et al, Brazilin blocks catabolic processes in human osteoarthritic chondrocytes via inhibition of NFKB1/p50. J Orthop Res. 2018 Sep;36(9):2431-2438.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
555.8±50.0 °C at 760 mmHg

[ Melting Point ]:
156-157ºC

[ Molecular Formula ]:
C₁₆H₁₄O₅

[ Molecular Weight ]:
286.279

[ Flash Point ]:
289.9±30.1 °C

[ Exact Mass ]:
286.084137

[ PSA ]:
90.15000

[ LogP ]:
1.32

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.774

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DE3124000

CHEMICAL NAME :: Benz(b)indeno(1,2-d)pyran-3,6a,9,10(6H)-tetrol, 7,11b-dihydro-

CAS REGISTRY NUMBER :: 474-07-7

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C16-H14-O5

MOLECULAR WEIGHT :: 286.30

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),252,1982

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

Synthetic Route

Click to get detail synthetic route

Related Compounds

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