A phenolic compound with diverse biological activities
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Isomer(s)
361891-O-Caffeoylquinic Acid
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5-O-Caffeoylquinic Acid

Item No. 25054

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3R,4S,5R)-3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
CAS Number
906-33-2
Synonyms
  • 5-Caffeoylquinic Acid
  • trans-5-O-Caffeoylquinic Acid
  • 5-CQA
  • Neochlorogenic Acid
Molecular Formula
C16H18O9
Formula Weight
354.3
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, 328 nm
SMILES
OC1=CC=C(/C=C/C(O[C@@H]2C[C@](C(O)=O)(O)C[C@@H](O)[C@@H]2O)=O)C=C1O
InChi Code
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1
InChi Key
CWVRJTMFETXNAD-NXLLHMKUSA-N
Origin
Plant/Lonicera japonica
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $90

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    10 mg

    $158

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    25 mg

    $349

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    50 mg

    $609

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    5-O-Caffeoylquinic acid (5-CQA) is a phenolic compound that has been found in M. domestica and has diverse biological activities, including antioxidant, anti-inflammatory, and antidiabetic properties.1,2,3,4 5-CQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805; EC50 = 0.184 mg/ml) and 2,2ʹ-azobis(2-amidinopropane) dihydrochloride (AAPH; Item No. 82235) radicals in cell-free assays (IC50 = 0.124 mg/ml).1 It decreases IL-6 and TNF-α levels in serum and macrophage infiltration into epididymal adipose tissue in rats fed a high-fat diet when administered at a dose of 90 mg/kg per day.3 5-CQA (90 mg/kg per day) also decreases serum and liver free fatty acid (FFA) levels and lowers blood glucose level in an oral glucose tolerance test in high-fat diet-fed rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamauzu, Y., Yasui, H., Inno, T., et al. Phenolic profile, antioxidant property, and anti-influenza viral activity of Chinese quince (Pseudocydonia sinensis Schneid.), quince (Cydonia oblonga Mill.), and apple (Malus domestica Mill.) fruits. J. Agric. Food Chem. 53(4), 928-934 (2005).

    2. Iwai, K., Kishimoto, N., Kakino, Y., et al. In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans. J. Agric. Food Chem. 52(15), 4893-4898 (2004).

    3. Liu, S.L., Peng, B.J., Zhong, Y.L., et al. Effect of 5-caffeoylquinic acid on the NF-κB signaling pathway, peroxisome proliferator-activated receptor gamma 2, and macrophage infiltration in high-fat diet-fed Sprague-Dawley rat adipose tissue. Food Funct. 6(8), 2779-2786 (2015).

    4. Huang, K., Liang, X.C., Zhong, Y.L., et al. 5-Caffeoylquinic acid decreases diet-induced obesity in rats by modulating PPARα and LXRα transcription. J. Sci. Food Agric. 95(9), 1903-1910 (2015).