A polyphenol with diverse biological activities
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1,4-Dicaffeoylquinic Acid

Item No. 33842

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1α,3R,4α,5R)-rel-1,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,5-dihydroxy-cyclohexanecarboxylic acid
CAS Number
1182-34-9
Synonyms
  • 1,4-DCQA
  • 1,4-Dicaffeylquinic Acid
Molecular Formula
C25H24O12
Formula Weight
516.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
220, 246, 330 nm
SMILES
OC(C=C1C=CC(O[C@]2(C[C@H]([C@H]([C@@H](C2)O)OC(C=CC3=CC(O)=C(C=C3)O)=O)O)C(O)=O)=O)=C(C=C1)O
InChi Code
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(32)36-23-19(30)11-25(24(34)35,12-20(23)31)37-22(33)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-31H,11-12H2,(H,34,35)/t19-,20-,23-,25+/m1/s1
InChi Key
IYXQRCXQQWUFQV-BBLPPJRLSA-N
Origin
Plant/Lonicera japonica Thunb.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    500 µg

    $86

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    1 mg

    $154

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    5 mg

    $470

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    10 mg

    $853

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    Product Description

    1,4-Dicaffeoylquinic acid is a polyphenol that has been found in C. coronarium and has diverse biological activities.1,2,3,4 It scavenges DPPH (Item No. 14805) radicals and inhibits xanthine oxidase (XO; IC50 = 7.36 µM).1,2 1,4-Dicaffeoylquinic acid (25 µM) decreases protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16/F1 murine melanocytes, inhibits melanogenesis in the same cells, and decreases tyrosinase activity in B16/F1 cell lysates.3 It increases biliary flow in rats in a dose-dependent manner.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alberati, D., Moreau, J.-L., Lengyel, J., et al. Glycine reuptake inhibitor RG1678: A pharmacologic characterization of an investigational agent for the treatment of schizophrenia. Neuropharmacology 62(2), 1152-1161 (2012).

    2. Cao, W., Fang, Y., Wu, T., et al. Insights from multispectral and molecular docking investigation on the xanthine oxidase inhibition by 1,4-dicaffeoylquinic acid. J. Mol. Struct. 1219, 128475 (2020).

    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).

    4. Preziosi, P., Loscalzo, B., and Marmo, E. Comparison of choleretic effects of CYN and Na-dehydrocholate. Experientia 15(4), 135-138 (1959).