An internal standard for the quantification of curcumin
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Unlabeled Version(s)
81025Curcumin
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Curcumin-d6

Item No. 25438

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1E,4Z,6E)-5-hydroxy-1,7-bis[4-hydroxy-3-(methoxy-d3)phenyl]-1,4,6-heptatrien-3-one
CAS Number
1335198-02-1
Molecular Formula
C21H14D6O6
Formula Weight
374.4
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
0.1 M NaOH: >3 mg/mlAcetone: >20 mg/ml
SMILES
OC(/C=C/C1=CC(OC([2H])([2H])[2H])=C(O)C=C1)=C\C(/C=C/C2=CC(OC([2H])([2H])[2H])=C(O)C=C2)=O
InChi Code
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13-/i1D3,2D3
InChi Key
ZIUSSTSXXLLKKK-JGJCSXQMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $90

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    1 mg

    $168

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    5 mg

    $370

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    Product Description

    Curcumin-d6 is intended for use as an internal standard for the quantification of curcumin (Item Nos. 81025 | 81025.1) by GC- or LC-MS. Curcumin is the major yellow pigment in turmeric and curry and has antioxidant, anti-inflammatory, and antitumor activities.1,2,3,4 It inhibits nitric oxide (NO) production (IC50 = 6 μM) and reduces inducible nitric oxide synthase (iNOS) activity in LPS-stimulated RAW 264.7 cells.1 Curcumin inhibits release of histamine and the inflammatory cytokines TNF-α, IL-1β, IL-6, and IL-8 from HMC-1 mast cells.2 In vivo, curcumin decreases serum levels of histamine and TNF-α, inhibits histopathological changes of nasal mucosa, and decreases the number of sneezes and nasal rubbing in a mouse model of ovalbumin-induced rhinitis. Curcumin (100 or 200 mg/kg) prevents ovalbumin-induced accumulation of 3-nitrotyrosine (3-NT), a marker of oxidative stress, in mouse heart. Topical administration of curcumin (1-10 μmol) reduces the number of tumors induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mouse skin.3 Dietary administration of curcumin reduces the number of tongue neoplasms and preneoplastic lesions induced by 4-nitroquinoline 1-oxide (4-NQO) in rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brouet, I., and Ohshima, H. Curcumin, an anti-tumor promoter and anti-inflammatory agent, inhibits induction of nitric oxide synthase in activated macrophages. Biochem. Biophys. Res. Commun. 206, 533-540 (1995).

    2. Zhang, N., Li, H., Jia, J., et al. Anti-inflammatory effect of curcumin on mast cell-mediated allergic responses in ovalbumin-induced allergic rhinitis mouse. Cell. Immunol. 298(1-2), 88-95 (2015).

    3. Conney, A.H., Lysz, T., Ferraro, T., et al. Inhibitory effect of curcumin and some related dietary compounds on tumor promotion and arachidonic acid metabolism in mouse skin. Adv. Enzyme Regul. 31, 385-396 (1991).

    4. Tanaka, T., Makita, H., Ohnishi, M., et al. Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis by dietary curcumin and hesperidin: Comparison with the protective effect of β-carotene. Cancer Res. 54, 4653-4659 (1994).