Natural curcuminoid with roles in Alzheimer’s, cancer, and inflammation
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Bisdemethoxycurcumin

Item No. 10960

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,7-bis(4-hydroxyphenyl)-1E,6E-heptadiene-3,5-dione
CAS Number
33171-05-0
Synonyms
  • BDMC
Molecular Formula
C19H16O4
Formula Weight
308.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 10 mg/mlEthanol: 5 mg/ml
λmax
419 nm
SMILES
OC1=CC=C(/C=C/C(CC(/C=C/C2=CC=C(O)C=C2)=O)=O)C=C1
InChi Code
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
InChi Key
PREBVFJICNPEKM-YDWXAUTNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $63

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    10 mg

    $118

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    25 mg

    $168

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    50 mg

    $303

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    Product Description

    Bisdemethoxycurcumin (BDMC) is a natural demethoxy derivative of curcumin. It is a potent activator of macrophage phagocytosis, interacting with 1α,25-dihydroxy vitamin D3 to stimulate amyloid-β clearance by macrophages (optimal stimulation at 100 nM BDMC).1,2,3 More stable than curcumin in physiological media, BDMC suppresses proliferation in cancer cells.4,5 It down-regulates the transcriptional coactivator p300, suppressing the Wnt/β-catenin pathway, and inhibits LPS induction of iNOS expression.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiala, M., Liu, P.T., Espinosa-Jeffrey, A., et al. Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer’s disease patients are improved by bisdemethoxycurcumin. Proc. Natl. Acad. Sci. USA 104(31), 12849-12854 (2007).

    2. Masoumi, A., Goldenson, B., Ghirmai, S., et al. 1α,25-dihydroxyvitamin D3 interacts with curcuminoids to stimulate amyloid-β clearance by macrophages of Alzheimer’s disease patients. J. Alzheimers Dis. 17(3), 703-717 (2009).

    3. Cashman, J.R., Fhirmai, S., Abel, K.J., et al. Immune defects in Alzheimer’s disease: New medications development. BMC Neurosci. 9(Suppl2), S13 (2008).

    4. Sandur, S.K., Pandley, M.K., Ahn, K.S., et al. Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. Carcinogenesis 28(8), 1765-1773 (2007).

    5. Basile, V., Ferrari, E., Lazzari, S., et al. Curcumin derivatives: Molecular basis of their anti-cancer activity. Biochem. Pharmacol. 78(10), 1305-1315 (2009).

    6. Ryu, M.J., Cho, M., Song, J.Y., et al. Natural derivatives of curcumin attenuate the Wnt/β-catenin pathway through down-regulation of the transcriptional coactivator p300. Biochem. Biophys. Res. Commun. 377(4), 1304-1308 (2008).

    7. Mahattanadul, S., Nakamura, T., Panichayupakaranant, P., et al. Comparative antiulcer effect of bisdemethoxycurcumin and curcumin in a gastric ulcer model system. Phytomedicine 16(4), 342-351 (2009).