A polyphenol with diverse biological activities
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3,4-Dicaffeoylquinic Acid

Item No. 25053

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,3R,4R,5R)-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid
CAS Number
14534-61-3
Synonyms
  • 3,4-DCQA
  • Isochlorogenic Acid B
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
218, 330 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-PSEXTPKNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $127

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    10 mg

    $203

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    25 mg

    $380

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    50 mg

    $633

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    Product Description

    3,4-Dicaffeoylquinic acid (3,4-DCQA) is a polyphenol with diverse biological activities.1,2,3,4 3,4-DCQA (1-500 μg/ml) inhibits acetylcholinesterase (ACE) and α-glucosidase in a concentration-dependent manner.1,3 It reduces mutagenicity of Trp-P-1 against S. typhimurium by 59% when used at a concentration of 0.57 mM.2 3,4-DCQA has antioxidant activity in ferric reducing, β-carotene bleaching, and DPPH scavenging assays (EC50s = 2.18, 23.85, and 68.91 μg/ml, respectively).3 It is cytotoxic to NCI-H23 lung adenocarcinoma cells (EC50 = 3.26 μg/ml). In vivo, 3,4-DCQA (50 mg/kg) increases tumor necrosis factor-related apoptosis inducing ligand (TRAIL) mRNA, reduces influenza H1N1 hemagglutinin (HA) mRNA, and increases survival in a mouse model of influenza A infection.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Oh, H., Kang, D.-G., Lee, S., et al. Angiotensin converting enzyme inhibitors from Cuscuta japonica Choisy. J. Ethnopharmacol. 83(1-2), 105-108 (2012).

    2. Yoshimoto, M., Yahara, S., Okuno, S., et al. Antimutagenicity of mono-, di-, and tricaffeoylquinic acid derivatives isolated from sweetpotato (Ipomoea batatas L.) leaf. Biosci. Biotechnol. Biochem. 66(11), 2336-2341 (2002).

    3. Ooi, K.L., Muhammad, T.S.T., Tan, M.L., et al. Cytotoxic, apoptotic and anti-α-glucosidase activities of 3,4-di-O-caffeoyl quinic acid, an antioxidant isolated from the polyphenolic-rich extract of Elephantopus mollis Kunth. J. Ethnopharmacol. 135(3), 685-695 (2011).

    4. Takemura, T., Urushisaki, T., Fukuoka, M., et al. 3,4-Dicaffeoylquinic acid, a major constituent of Brazilian propolis, increases TRAIL expression and extends the lifetimes of mice infected with the influenza A virus. Evid. Based Complement. Alternat. Med. 2012:946867, (2012).