A phytochemical with diverse biological activities
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Brazilein

Item No. 36736

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6a,7-dihydro-3,6a,10-trihydroxy-benz[b]indeno[1,2-d]pyran-9(6H)-one
CAS Number
600-76-0
Molecular Formula
C16H12O5
Formula Weight
284.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 11 mg/mlDMSO: 11 mg/mlEthanol: Slightly solublePBS (pH 7.2): 0.16 mg/ml
λmax
447 nm
SMILES
O=C1C=C2C(C=C1O)=C3C4=C(OCC3(C2)O)C=C(O)C=C4
InChi Code
InChI=1S/C16H12O5/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/h1-5,17,19-20H,6-7H2
InChi Key
MLWIYODOURBGPI-UHFFFAOYSA-N
Origin
Plant/Paubrasilia echinata
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $79

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    5 mg

    $375

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    10 mg

    $672

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    Cayman Chemical
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    Product Description

    Brazilein is a phytochemical that has been found in C. sappan and has diverse biological activities.1,2,3,4 It is active against E. coli, P. aeruginosa, and methicillin-susceptible S. aureus (MSSA; MICs = 32, 512, and 512 µg/ml), as well as a panel of 10 clinical isolates of methicillin-resistant S. aureus (MRSA; MIC50s = 16-32 µg/ml).1 Brazilein (10 µM) inhibits LPS-induced nitric oxide (NO) production in J774A.1 cells.2 It is cytotoxic to HepG2, Hep3B, MDA-MB-231, MCF-7, A549, and Ca9-22 cancer cells (IC50s = 3.15, 3.42, 2.36, 3.96, 9.68, and 8.63 µg/ml, respectively).3 Brazilein (1-10 µg/ml) also inhibits the proliferation of isolated mouse spleen lymphocytes induced by concanavalin A (Item No. 14951).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zuo, G.Y., Han, Z.Q., Hao, X.Y., et al. Synergy of aminoglycoside antibiotics by 3-benzylchroman derivatives from the chinese drug Caesalpinia sappan against clinical methicillin-resistant Staphylococcus aureus (MRSA). Phytomedicine 21(7), 936-941 (2014).

    2. Sasaki, Y., Hosokawa, T., Nagai, M., et al. In vitro study for inhibition of NO production about constituents of Sappan Lignum. Biol. Pharm. Bull. 30(1), 193-196 (2007).

    3. Yen, C.-T., Nakagawa-Goto, K., Hwang, T.-L., et al. Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents. Bioorg. Med. Chem. Lett. 20(3), 1037-1039 (2010).

    4. Ye, M., Xie, W.-D., Lei, F., et al. Brazilein, an important immunosuppressive component from Caesalpinia sappan L. Int. Immunopharmacol. 6(3), 426-432 (2006).