A dicaffeoyl ester with diverse biological activities
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Chicoric Acid

Item No. 24960

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R)-2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-butanedioic acid
CAS Number
70831-56-0
Synonyms
  • L-Chicoric Acid
  • Dicaffeoyltartaric Acid
  • NSC 99173
Molecular Formula
C22H18O12
Formula Weight
474.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2)(1:3): 0.25 mg/mlDMSO: 25 mg/ml
λmax
220, 248, 334 nm
SMILES
OC1=CC=C(/C=C/C(O[C@@H](C(O)=O)[C@H](C(O)=O)OC(/C=C/C2=CC(O)=C(O)C=C2)=O)=O)C=C1O
InChi Code
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
InChi Key
YDDGKXBLOXEEMN-IABMMNSOSA-N
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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    25 mg

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    50 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Chicoric acid is a dicaffeoyl ester that has been found in C. intybus with diverse biological activities.1 Chicoric acid (50-200 μg/ml) dose-dependently reduces the viability of Caco-2 and HCT116 human colorectal cancer cells.2 It inhibits HIV integrase activities, including 3'-processing of a DNA oligonucleotide and integration with template DNA (IC50s = 1.1 and 0.8 μM, respectively).3 Chicoric acid (0.5-10 μM) noncompetitively inhibits integration of HIV DNA by HIV integrase and, at concentrations greater than or equal to 5 μM, inhibits HIV entry into H9 cells.4 Oral administration of chicoric acid (10 and 30 mg/kg) reduces hepatic lipid accumulation, lipid peroxidation, and fibrosis, inhibits production of pro-inflammatory cytokines and activation of NF-kB, and activates the AMPK signaling pathway in a mouse model of non-alcoholic steatohepatitis (NASH) induced by a methionine and choline-deficient diet.5 Chicoric acid (2 mg/kg) also reduces blood glucose levels by 54% in mice with streptozotocin-induced diabetes.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xiao, H., Xie, G., Wang, J., et al. Chicoric acid prevents obesity by attenuating hepatic steatosis, inflammation and oxidative stress in high-fat diet-fed mice. Food Res. Int. 54(1), 345-353 (2013).

    2. Tsai, Y.-L., Chiu, C.-C., Chen, J.Y.-F., et al. Cytotoxic effects of Echinacea purpurea flower extracts and cichoric acid on human colon cancer cells through induction of apoptosis. J. Ethnaopharmacol. 143(3), 914-919 (2012).

    3. Lin, Z., Neamati, N., Zhao, H., et al. Chicoric acid analogues as HIV-1 integrase inhibitors. J. Med. Chem. 42(8), 1401-1414 (1999).

    4. Reinke, R.A., Lee, D.J., McDougall, B.R., et al. L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology 326(2), 203-219 (2004).

    5. Kim, M., Yoo, G., Randy, A., et al. Chicoric acid attenuate a nonalcoholic steatohepatitis by inhibiting key regulators of lipid metabolism, fibrosis, oxidation, and inflammation in mice with methionine and choline deficiency. Mol. Nutr. Food Res. 61(5), (2017).

    6. Casanova, L.M., da Silva, D., Sola-Penna, M., et al. Identification of chicoric acid as a hypoglycemic agent from Ocimum gratissimum leaf extract in a biomonitoring in vivo study. Filoterapia 93, 132-141 (2014).