A flavonoid with diverse bioactivites
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Brazilin

Item No. 22456

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7,11bR-dihydro-benz[b]indeno[1,2-d]pyran-3,6aS,9,10(6H)-tetrol
CAS Number
474-07-7
Synonyms
  • (+)Brazilin
  • NSC 56652
Molecular Formula
C16H14O5
Formula Weight
286.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
290 nm
SMILES
OC(C=C1)=CC2=C1[C@](C(C=C(O)C(O)=C3)=C3C4)([H])[C@]4(O)CO2
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $153

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    10 mg

    $253

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    50 mg

    $1,086

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    Cayman Chemical
    Neutrophil Biology Wall Poster

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    Product Description

    Brazilin is an isoflavonoid originally isolated from C. sappan that has diverse biological activities, including neuroprotective, anti-inflammatory, antibacterial, and antioxidant properties.1 Brazilin inhibits Aβ (1-42) fibrillogenesis (IC50 = 1.5 µM) more potently than (-)-epigallocatechin gallate (Item No. 70935), cucurmin (Item No. 81025), and resveratrol (Item Nos. 10004235 | 70675).2 It also prevents remodeling of mature Aβ (1-42) fibrils. Brazilin inhibits the production of cytokines, including PGE2 (Item No. 14010) and TNF-α (IC50s = 12.6 and 87.2 µM).3 It is effective against Gram-positive and Gram-negative bacteria with MICs ranging from 31.3 to 250 µg/ml.4 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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lee, H., Kang, S.W., Byun, H.S., et al. Brazilin limits inflammatory responses through induction of prosurvival autophagy in rheumatoid fibroblast-like synoviocytes. PloS One 10(8), e313 (2015).

    2. Du, W.-J., Guo, J.-J., Gao, M.-T., et al. Brazilin inhibits amyloid b-protein fibrillogenesis, remodels amyloid fibrils and reduces amyloid cytotoxicit. Sci. Rep. 5(7992), (2015).

    3. Tewtrakul, S., Tungcharoen, P., Sudsai, T., et al. Antiinflamatory and wound healing effects of Caesalpinia sappan L. Phytother. Res. 29(6), 850-856 (2015).

    4. Nirmal, N.P., and Panichayupakaranant, P. Antioxidant, antibacterial, and anti-inflammatory activities of standardized brazilin-rich Caesalpinia sappan extract. Pharm. Biol. 53(9), 1339-1343 (2015).

    5. Kim, J., Lee, H.K., Chang, T.-S., et al. Inhibitory effect of brazilin on osteoclast differentiation and its mechanism of action. Int. Immunopharmacol. 29(2), 628-634 (2015).