A polyphenol
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1,3-Dicaffeoylquinic Acid

Item No. 25022

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3R,4S)-1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5R-dihydroxy-cyclohexanecarboxylic acid
CAS Number
30964-13-7
Synonyms
  • 1,3-DCQA
  • 1,3-Dicaffeylquinic Acid
Molecular Formula
C25H24O12
Formula Weight
516.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 5 mg/mlEthanol: 0.2 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
222, 248, 326 nm
SMILES
OC1=CC=C(/C=C/C(O[C@H]2[C@@H](O)[C@H](O)C[C@](OC(/C=C/C3=CC(O)=C(O)C=C3)=O)(C(O)=O)C2)=O)C=C1O
InChi Code
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChi Key
YDDUMTOHNYZQPO-RVXRWRFUSA-N
Origin
Plant/Tribute Chrysanthemum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $129

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    10 mg

    $183

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    25 mg

    $415

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    50 mg

    $763

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    Product Description

    1,3-Dicaffeoylquinic acid is a polyphenol that has been found in C. scolymus.1 It decreases the expression and protein levels of inducible nitric oxide synthase (iNOS) when used at a concentration of 10 µM in human coronary artery smooth muscle cells (HCASMCs) treated with a cytokine mixture.2 1,3-Dicaffeoylquinic acid decreases protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16F1 murine melanocytes.3 It inhibits melanogenesis in B16F1 cells and decreases tyrosinase activity in cell lysates when used at a concentration of 25 µM.1 1,3-Dicaffeoylquinic acid (20 and 40 µM) reduces triglyceride levels in sodium oleate-induced hyperlipidemic HepG2 cells compared to hyperlipidemic control cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, Y., Chen, X., Luo, G., et al. Discovery of potential inhibitors of squalene synthase from traditional chinese medicine based on virtual screening and in vitro evaluation of lipid-lowering effect. Molecules 23(5), E1040 (2018).

    2. Xia, N., Pautz, A., Wollscheid, U., et al. Artichoke, cynarin and cyanidin downregulate the expression of inducible nitric oxide synthase in human coronary smooth muscle cells. Molecules 19(3), 3654-3668 (2014).

    3. Ha, J.H., and Park, S.N. Mechanism underlying inhibitory effect of six dicaffeoylquinic acid isomers on melanogenesis and the computational molecular modeling studies. Bioorg. Med. Chem. 26(14), 4201-4208 (2018).