A polyphenol with diverse biological activities
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4,5-Dicaffeoylquinic Acid

Item No. 27892

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3R,4S,5R)-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid
CAS Number
57378-72-0
Synonyms
  • 4,5-DCQA
  • Isochlorogenic Acid C
Molecular Formula
C25H24O12
Formula Weight
516.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:5): 0.1 mg/mlDMSO: 5 mg/ml
λmax
219, 245, 331 nm
SMILES
O=C(/C=C/C1=CC=C(O)C(O)=C1)O[C@H]2[C@@H](OC(/C=C/C3=CC=C(O)C(O)=C3)=O)[C@H](O)C[C@@](C(O)=O)(O)C2
InChi Code
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChi Key
UFCLZKMFXSILNL-RVXRWRFUSA-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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    Product Description

    4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties.1,2,3,4,5 It inhibits HIV-1 integrase 3' end processing, 3’ end joining, and disintegration with IC50 values of 0.13, 0.24, and 0.3 μg/ml, respectively.3 It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC50 value of 2 μg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (IC50 = 19.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF; Item No. 21495) and cytochalasin B (Item No. 11328; IC50 = 1.49 μM).2 It decreases prostaglandin E2 (PGE2; Item No. 14010) production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 µg/ml but increases it when used at 200 µg/ml and increases production of TNF-α at concentrations ranging from 5 to 200 µg/ml.4 It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 µM) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bogaevskii, A.K., Dranik, L.I., and Borisov, M.I. The hydroxycinnamic acids of Galium fagetorum and G. pseudomollugo. Chem. Nat. Compd. 6(6), 761-762 (1970).

    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. Robinson, W.E., Jr., Cordeiro, M., Abdel-Malek, S., et al. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: Inhibition of the core catalytic domain of human immunodeficiency virus integrase. Mol. Pharmacol. 50(4), 846-855 (1996).

    4. dos Santos, M.D., Chen, G., Almeida, M.C., et al. Effects of caffeoylquinic acid derivatives and C-flavonoid from Lychnophora ericoides on in vitro inflammatory mediator production. Nat. Prod. Commun. 5(5), 733-740 (2010).

    5. 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).