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MedKoo Cat#: 329871 | Name: Chicoric Acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chicoric Acid is a natural compound. To date, plants from at least 63 genera and species have been found to contain chicoric acid, and while the compound is used as a processing quality indicator, it may also have useful health benefits. Chicoric acid induces apoptosis in 3T3-L1 preadipocytes through ROS-mediated PI3K/Akt and MAPK signaling pathways. Chicoric acid stimulates AMP kinase pathway in L6 myotubes and extends lifespan in Caenorhabditis elegans.

Chemical Structure

Chicoric Acid
Chicoric Acid
CAS#70831-56-0

Theoretical Analysis

MedKoo Cat#: 329871

Name: Chicoric Acid

CAS#: 70831-56-0

Chemical Formula: C22H18O12

Exact Mass: 474.0798

Molecular Weight: 474.37

Elemental Analysis: C, 55.70; H, 3.82; O, 40.47

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
10mg USD 450.00 2 Weeks
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Related CAS #
70831-56-0
Synonym
Chicoric acid; Cichoric Acid; L-Chicoric Acid; Dicaffeoyltartaric Acid; NSC 99173; NSC99173; NSC-99173
IUPAC/Chemical Name
(2R,3R)-2,3-Bis[[(E)-3-(3,4-dihydroxyphenyl)acryloyl]oxy]succinic Acid
InChi Key
YDDGKXBLOXEEMN-IABMMNSOSA-N
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
SMILES Code
O=C(O)[C@H](OC(/C=C/C1=CC=C(O)C(O)=C1)=O)[C@@H](OC(/C=C/C2=CC=C(O)C(O)=C2)=O)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Though chicoric acid was first identified in 1958, it was largely ignored until recent popular media coverage cited potential health beneficial properties from consuming food and dietary supplements containing this compound
Product Data
Product Data
Instruction
View handling instruction
Biological target:
L-Chicoric Acid ((-)-Chicoric acid) is a dicaffeoyltartaric acid and a potent, selective and reversible HIV-1 integrase inhibitor with an IC50 of ~100 nM.
In vitro activity:
Herein, the major methylated metabolites of CA (chicoric acid) were isolated from an in vitro co-incubation system, and their structures were elucidated. The antioxidant activities of the monomethylated metabolites (M1) and dimethylated metabolites (M2) of CA were evaluated against H2O2-induced oxidative stress damage in HepG2 cells and compared to CA. The results indicated that both M1 and M2 had better antioxidant capacities than CA by increasing cell viability, improving mitochondrial function, and balancing cellular redox status. Reference: J Agric Food Chem. 2021 Feb 24;69(7):2179-2189. https://pubmed.ncbi.nlm.nih.gov/33577312/
In vivo activity:
CA (chicoric acid) (15 and 30 mg/kg) administration significantly reduced body weight and white adipose weight in comparison with the HFD group (p < 0.01, p < 0.001). Compared with the ND mice, the HFD mice exhibited a significant increase in fasting blood glucose level (p < 0.001). Consequently, CA significantly reduced fasting blood level in mice fed with a high-fat diet (Figure 1(c); p < 0.001). Reference: Oxid Med Cell Longev. 2020; 2020: 9734560. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7657699/
Solvent mg/mL mM comments
Solubility
DMSO 73.3 154.58
DMF 30.0 63.24
DMF:PBS (pH 7.2) (1:3) 0.3 0.53
Ethanol 95.0 200.26
Water 8.0 16.86
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 474.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Chang X, Dong S, Bai W, Di Y, Gu R, Liu F, Zhao B, Wang Y, Liu X. Methylated Metabolites of Chicoric Acid Ameliorate Hydrogen Peroxide (H2O2)-Induced Oxidative Stress in HepG2 Cells. J Agric Food Chem. 2021 Feb 24;69(7):2179-2189. doi: 10.1021/acs.jafc.0c07521. Epub 2021 Feb 12. PMID: 33577312. 2. Ma X, Zhang J, Wu Z, Wang X. Chicoric acid attenuates hyperglycemia-induced endothelial dysfunction through AMPK-dependent inhibition of oxidative/nitrative stresses. J Recept Signal Transduct Res. 2021 Aug;41(4):378-392. doi: 10.1080/10799893.2020.1817076. Epub 2020 Sep 9. PMID: 32900249. 3. Ding X, Jian T, Li J, Lv H, Tong B, Li J, Meng X, Ren B, Chen J. Chicoric Acid Ameliorates Nonalcoholic Fatty Liver Disease via the AMPK/Nrf2/NFκB Signaling Pathway and Restores Gut Microbiota in High-Fat-Diet-Fed Mice. Oxid Med Cell Longev. 2020 Nov 3;2020:9734560. doi: 10.1155/2020/9734560. PMID: 33204402; PMCID: PMC7657699. 4. Hussein OE, Hozayen WG, Bin-Jumah MN, Germoush MO, Abd El-Twab SM, Mahmoud AM. Chicoric acid prevents methotrexate hepatotoxicity via attenuation of oxidative stress and inflammation and up-regulation of PPARγ and Nrf2/HO-1 signaling. Environ Sci Pollut Res Int. 2020 Jun;27(17):20725-20735. doi: 10.1007/s11356-020-08557-y. Epub 2020 Apr 3. PMID: 32246423.
In vitro protocol:
1. Chang X, Dong S, Bai W, Di Y, Gu R, Liu F, Zhao B, Wang Y, Liu X. Methylated Metabolites of Chicoric Acid Ameliorate Hydrogen Peroxide (H2O2)-Induced Oxidative Stress in HepG2 Cells. J Agric Food Chem. 2021 Feb 24;69(7):2179-2189. doi: 10.1021/acs.jafc.0c07521. Epub 2021 Feb 12. PMID: 33577312. 2. Ma X, Zhang J, Wu Z, Wang X. Chicoric acid attenuates hyperglycemia-induced endothelial dysfunction through AMPK-dependent inhibition of oxidative/nitrative stresses. J Recept Signal Transduct Res. 2021 Aug;41(4):378-392. doi: 10.1080/10799893.2020.1817076. Epub 2020 Sep 9. PMID: 32900249.
In vivo protocol:
1. Ding X, Jian T, Li J, Lv H, Tong B, Li J, Meng X, Ren B, Chen J. Chicoric Acid Ameliorates Nonalcoholic Fatty Liver Disease via the AMPK/Nrf2/NFκB Signaling Pathway and Restores Gut Microbiota in High-Fat-Diet-Fed Mice. Oxid Med Cell Longev. 2020 Nov 3;2020:9734560. doi: 10.1155/2020/9734560. PMID: 33204402; PMCID: PMC7657699. 2. Hussein OE, Hozayen WG, Bin-Jumah MN, Germoush MO, Abd El-Twab SM, Mahmoud AM. Chicoric acid prevents methotrexate hepatotoxicity via attenuation of oxidative stress and inflammation and up-regulation of PPARγ and Nrf2/HO-1 signaling. Environ Sci Pollut Res Int. 2020 Jun;27(17):20725-20735. doi: 10.1007/s11356-020-08557-y. Epub 2020 Apr 3. PMID: 32246423.
1: Liu Q, Wang Y, Xiao C, Wu W, Liu X. Metabolism of chicoric acid by rat liver microsomes and bioactivity comparisons of chicoric acid and its metabolites. Food Funct. 2015 Jun;6(6):1928-35. doi: 10.1039/c5fo00073d. PubMed PMID: 25968347. 2: Landmann M, Kanuri G, Spruss A, Stahl C, Bergheim I. Oral intake of chicoric acid reduces acute alcohol-induced hepatic steatosis in mice. Nutrition. 2014 Jul-Aug;30(7-8):882-9. doi: 10.1016/j.nut.2013.11.015. Epub 2013 Dec 5. PubMed PMID: 24985007. 3: Lee NY, Chung KS, Jin JS, Bang KS, Eom YJ, Hong CH, Nugroho A, Park HJ, An HJ. Effect of Chicoric Acid on Mast Cell-Mediated Allergic Inflammation in Vitro and in Vivo. J Nat Prod. 2015 Dec 24;78(12):2956-62. doi: 10.1021/acs.jnatprod.5b00668. Epub 2015 Nov 23. PubMed PMID: 26593037. 4: Lee J, Scagel CF. Chicoric acid: chemistry, distribution, and production. Front Chem. 2013 Dec 31;1:40. doi: 10.3389/fchem.2013.00040. eCollection 2013. Review. PubMed PMID: 24790967; PubMed Central PMCID: PMC3982519. 5: Xiao H, Wang J, Yuan L, Xiao C, Wang Y, Liu X. Chicoric acid induces apoptosis in 3T3-L1 preadipocytes through ROS-mediated PI3K/Akt and MAPK signaling pathways. J Agric Food Chem. 2013 Feb 20;61(7):1509-20. doi: 10.1021/jf3050268. Epub 2013 Feb 11. PubMed PMID: 23363008. 6: Casanova LM, da Silva D, Sola-Penna M, Camargo LM, Celestrini Dde M, Tinoco LW, Costa SS. Identification of chicoric acid as a hypoglycemic agent from Ocimum gratissimum leaf extract in a biomonitoring in vivo study. Fitoterapia. 2014 Mar;93:132-41. doi: 10.1016/j.fitote.2013.12.024. Epub 2014 Jan 10. PubMed PMID: 24418658. 7: Kuban-Jankowska A, Sahu KK, Gorska M, Tuszynski JA, Wozniak M. Chicoric acid binds to two sites and decreases the activity of the YopH bacterial virulence factor. Oncotarget. 2016 Jan 19;7(3):2229-38. doi: 10.18632/oncotarget.6812. PubMed PMID: 26735581; PubMed Central PMCID: PMC4823031. 8: Saad EM, Madbouly A, Ayoub N, El Nashar RM. Preparation and application of molecularly imprinted polymer for isolation of chicoric acid from Chicorium intybus L. medicinal plant. Anal Chim Acta. 2015 Jun 2;877:80-9. doi: 10.1016/j.aca.2015.03.047. Epub 2015 Mar 30. PubMed PMID: 26002213. 9: Wang Y, Xie G, Liu Q, Duan X, Liu Z, Liu X. Pharmacokinetics, tissue distribution, and plasma protein binding study of chicoric acid by HPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Sep 15;1031:139-145. doi: 10.1016/j.jchromb.2016.07.045. Epub 2016 Jul 25. PubMed PMID: 27479684. 10: Schlernitzauer A, Oiry C, Hamad R, Galas S, Cortade F, Chabi B, Casas F, Pessemesse L, Fouret G, Feillet-Coudray C, Cros G, Cabello G, Magous R, Wrutniak-Cabello C. Chicoric acid is an antioxidant molecule that stimulates AMP kinase pathway in L6 myotubes and extends lifespan in Caenorhabditis elegans. PLoS One. 2013 Nov 11;8(11):e78788. doi: 10.1371/journal.pone.0078788. eCollection 2013. PubMed PMID: 24244361; PubMed Central PMCID: PMC3823992. 11: Barnaby SN, Sarker NH, Tsiola A, Banerjee IA. Biomimetic formation of chicoric-acid-directed luminescent silver nanodendrites. Nanotechnology. 2012 Jul 27;23(29):294011. doi: 10.1088/0957-4484/23/29/294011. Epub 2012 Jun 28. PubMed PMID: 22744213. 12: Azay-Milhau J, Ferrare K, Leroy J, Aubaterre J, Tournier M, Lajoix AD, Tousch D. Antihyperglycemic effect of a natural chicoric acid extract of chicory (Cichorium intybus L.): a comparative in vitro study with the effects of caffeic and ferulic acids. J Ethnopharmacol. 2013 Nov 25;150(2):755-60. doi: 10.1016/j.jep.2013.09.046. Epub 2013 Oct 12. PubMed PMID: 24126061. 13: Park CM, Jin KS, Lee YW, Song YS. Luteolin and chicoric acid synergistically inhibited inflammatory responses via inactivation of PI3K-Akt pathway and impairment of NF-κB translocation in LPS stimulated RAW 264.7 cells. Eur J Pharmacol. 2011 Jun 25;660(2-3):454-9. doi: 10.1016/j.ejphar.2011.04.007. Epub 2011 Apr 15. PubMed PMID: 21513709. 14: Kour K, Bani S. Chicoric acid regulates behavioral and biochemical alterations induced by chronic stress in experimental Swiss albino mice. Pharmacol Biochem Behav. 2011 Sep;99(3):342-8. doi: 10.1016/j.pbb.2011.05.008. Epub 2011 May 17. PubMed PMID: 21620882. 15: Kour K, Bani S. Augmentation of immune response by chicoric acid through the modulation of CD28/CTLA-4 and Th1 pathway in chronically stressed mice. Neuropharmacology. 2011 May;60(6):852-60. doi: 10.1016/j.neuropharm.2011.01.001. Epub 2011 Jan 25. PubMed PMID: 21272592. 16: King PJ, Robinson WE Jr. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. J Virol. 1998 Oct;72(10):8420-4. PubMed PMID: 9733896; PubMed Central PMCID: PMC110234. 17: Murthy HN, Kim YS, Park SY, Paek KY. Biotechnological production of caffeic acid derivatives from cell and organ cultures of Echinacea species. Appl Microbiol Biotechnol. 2014 Sep;98(18):7707-17. doi: 10.1007/s00253-014-5962-6. Epub 2014 Jul 31. Review. PubMed PMID: 25077780. 18: Bel-Rhlid R, Pagé-Zoerkler N, Fumeaux R, Ho-Dac T, Chuat JY, Sauvageat JL, Raab T. Hydrolysis of chicoric and caftaric acids with esterases and Lactobacillus johnsonii in Vitro and in a gastrointestinal model. J Agric Food Chem. 2012 Sep 12;60(36):9236-41. doi: 10.1021/jf301317h. Epub 2012 Aug 31. PubMed PMID: 22920606. 19: Tousch D, Lajoix AD, Hosy E, Azay-Milhau J, Ferrare K, Jahannault C, Cros G, Petit P. Chicoric acid, a new compound able to enhance insulin release and glucose uptake. Biochem Biophys Res Commun. 2008 Dec 5;377(1):131-5. doi: 10.1016/j.bbrc.2008.09.088. Epub 2008 Oct 1. PubMed PMID: 18834859. 20: Lee SU, Shin CG, Lee CK, Lee YS. Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors. Eur J Med Chem. 2007 Oct;42(10):1309-15. Epub 2007 Mar 12. PubMed PMID: 17434650.