An HIV-1 integrase inhibitor and free radical scavenger
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1,5-Dicaffeoylquinic Acid

Item No. 25050

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,3R,4R,5R)-1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid
CAS Number
19870-46-3
Synonyms
  • 1,5-DCQA
  • 1,3-Dicaffeoylquinic Acid
Molecular Formula
C25H24O12
Formula Weight
516.5
Purity
≥98%
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, 330 nm
SMILES
OC1=CC=C(/C=C/C(O[C@H]2[C@H](O)[C@H](O)C[C@](C(O)=O)(OC(/C=C/C3=CC(O)=C(O)C=C3)=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-PSEXTPKNSA-N
Origin
Plant/Inulae Flos
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    1,5-Dicaffeoylquinic acid (1,5-DCQA) has been found in A. montana and is an HIV-1 integrase inhibitor and free radical scavenger.1,2 1,5-DCQA inhibits HIV-1 integrase 3' end processing, end joining, and disintegration with IC50 values of 0.35, 0.56, and 0.84 μg/ml, respectively.2 It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an ED50value of 2 μg/ml. 1,5-DCQA (0.25-1 μM) reduces the level of free radicals released from human polymorphonuclear (PMN) cells stimulated by N-formyl-Met-Leu-Phe (fMLP; Item No. 21495) in a dose-dependent manner.1 It also dose-dependently increases cell survival and glutathione (GSH) levels and decreases reactive oxygen species (ROS) production and lactate dehydrogenase (LDH) release in an oxygen-glucose deprivation/reperfusion assay in rat cerebral astrocytes when used at concentrations ranging from 5 to 100 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Heilmann, J., Merfort, I., and Weiss, M. Radical scavenger activity of different 3',4'-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescence. Planta Med. 61(5), 435-438 (1995).

    2. 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).

    3. Cao, X., Xiao, H., Zhang, Y., et al. 1, 5-Dicaffeoylquinic acid-mediated glutathione synthesis through activation of Nrf2 protects against OGD/reperfusion-induced oxidative stress in astrocytes. Brain Res. 1347, 142-148 (2010).