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SML2132

Sigma-Aldrich

Brazilin

Synonym(s):

Brasilin, (+)-Brazilin, (6aS,11bR)-7,11b-Dihydro-benz[b]indeno[1,2-d]pyran-3,6a,9,10(6H)-tetrol, 7, 11b-dihydrobenz[b]indeno[1,2-d]pyran-3,6a,9,10 (6H)-tetrol, NSC 56652, 6,6a,7,11b-Tetrahydro-3,6a,9,10-tetrahydroxyindeno[2,1-c]chromene, Natural Red 24

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About This Item

Empirical Formula (Hill Notation):
C16H14O5
CAS Number:
474-07-7
Molecular Weight:
286.28
Colour Index Number:
75280
EC Number:
207-477-6
MDL number:
MFCD00210817
UNSPSC Code:
12352200
NACRES:
NA.77

optical activity

[α]/D 108.0 to 133.0°, c = 0.5 in methanol

color

white to very dark brown

solubility

DMSO: 2 mg/mL

storage temp.

2-8°C

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/t15-,16+/m0/s1

InChI key

UWHUTZOCTZJUKC-JKSUJKDBSA-N

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Biochem/physiol Actions

Brazilin is a natural isoflavonoid red pigment with many biologic activities including neuroprotective, anti-inflammatory, antibacterial, antiproliferative, and antioxidant properties. Some of its activity is thought to be due to its regulation of the transcription factor NF-ΚB.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yanyan Jia et al.
International journal of molecular medicine, 38(1), 210-216 (2016-06-02)
Renal ischemia-reperfusion (I/R) injury is associated with high morbidity and mortality as there is currently no available effective therapeutic strategy with which to treat this injury. Thus, the aim of this study was to investigate the potential protective effects of
Zhan-Yuan Li et al.
Inflammation, 40(4), 1365-1374 (2017-05-13)
Hyperglycemia and inflammation play important roles in the pathogenesis of diabetic nephropathy (DN). Brazilin might be an effective pharmacological agent against hyperglycemia and inflammation. In our present study, we explored whether brazilin mitigated pathological progression, inflammation, and extracellular matrix (ECM)
Eun Byeol Lee et al.
Archives of pharmacal research, 40(7), 825-835 (2017-07-02)
This study contributes to the continual discovery of lifespan-extending compounds from plants, using the Caenorhabditis elegans model system. An ethyl acetate soluble fraction of methanol extract from the heartwood of Caesalpinia sappan showed a significant lifespan-extending activity. Subsequent activity-guided chromatography

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