A natural phenolic compound with diverse biological activities
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3,5-Dicaffeoylquinic Acid

Item No. 24964

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1α,3R,4α,5R)-3,5-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic acid
CAS Number
2450-53-5
Synonyms
  • 3,5-DCQA
  • Isochlorogenic Acid A
Molecular Formula
C25H24O12
Formula Weight
516.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 71 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 25 mg/ml
λmax
220, 246, 330 nm
SMILES
OC1=CC=C(/C=C/C(O[C@@H]2C[C@](C(O)=O)(O)C[C@@H](OC(/C=C/C3=CC=C(O)C(O)=C3)=O)[C@@H]2O)=O)C=C1O
InChi Code
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
InChi Key
KRZBCHWVBQOTNZ-PSEXTPKNSA-N
Origin
Plant/Lonicera japonica Thunb.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    25 mg

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    50 mg

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    Product Description

    3,5-Dicaffeoylquinic acid (3,5-DCQA) is a natural phenolic compound that has been found in L. japonica, I. kaushue, and other plants.1,2 It has antioxidant, anti-inflammatory, and antiviral biological activities.2,3,4 3,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (IC50 = 71.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF) and cytochalasin B (IC50 = 1.92 μM).2,3 It inhibits HIV-1 integrase 3'-end processing, strand transfer, and disintegration in a cell-free assay (IC50s = 0.33, 0.34, and 0.66 μg/ml, respectively) and inhibits HIV-1-induced cytotoxicity in MT-2 cells (ED50 = 1 μg/ml).4 In vivo, 3,5-DCQA (25 mg/kg) protects mice from acute lung injury induced by LPS and decreases neutrophil count in bronchoalveolar lavage fluid (BALF).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Peng, L.-Y., Mei, S.-X., Jiang, B., et al. Constituents from Lonicera japonica. Fitoterapia 71(6), 713-715 (2000).

    2. Chen, Y.-L., Hwang, T.-L., Yu, H.-P., et al. Ilex kaushue and its bioactive component 3,5-dicaffeoylquinic acid protected mice from lipopolysaccharide-induced acute lung injury. Sci. Rep. 6, 34243 (2016).

    3. Pantoja Pulido, K.D., Colmenares Dulcey, A.J., and Isaza Martínez, J.H. New caffeic acid derivative from Tithonia diversifolia (Hemsl.) A. Gray butanolic extract and its antioxidant activity. Food Chem. Toxicol. 109(Pt. 2), 1079-1085 (2017).

    4. Robinson, W.E., Jr., Reinecke, M.G., Abdel-Malek, S., et al. Inhibitors of HIV-1 replication that inhibit HIV integrase. Proc. Natl. Acad. Sci. USA 93(13), 6326-6331 (1996).