Chicoric acid
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| Category | Bioactive by-products |
| Catalog number | BBF-04079 |
| CAS | 6537-80-0 |
| Molecular Weight | 474.37 |
| Molecular Formula | C22H18O12 |
| Purity | ≥95% |
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Description
Chicoric acid is an antiviral substance.
Specification
| Synonyms | Chicoric; (2R,3R)-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid; (2R,3R)-2-O,3-O-Bis[3-(3,4-dihydroxyphenyl)acryloyl]tartaric acid; [2R,3R,(-)]-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid; 2-O,3-O-Bis[3-(3,4-dihydroxyphenyl)propenoyl]-L-tartaric acid; Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*))- |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Store at -20°C |
| IUPAC Name | (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid |
| Canonical SMILES | C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O |
| InChI | 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 |
Properties
| Appearance | Powder |
| Application | antiviral |
| Antibiotic Activity Spectrum | viruses |
| Boiling Point | 785°C at 760 mmHg |
| Melting Point | >193°C (dec.) |
| Density | 1.641 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Chicoric acid binds to two sites and decreases the activity of the YopH bacterial virulence factor.
Kuban-Jankowska A1, Sahu KK2, Gorska M1, Tuszynski JA2,3, Wozniak M1. Oncotarget. 2016 Jan 19;7(3):2229-38. doi: 10.18632/oncotarget.6812.
Chicoric acid (CA) is a phenolic compound present in dietary supplements with a large spectrum of biological properties reported ranging from antioxidant, to antiviral, to immunostimulatory properties. Due to the fact that chicoric acid promotes phagocytic activity and was reported as an allosteric inhibitor of the PTP1B phosphatase, we examined the effect of CA on YopH phosphatase from pathogenic bacteria, which block phagocytic processes of a host cell. We performed computational studies of chicoric acid binding to YopH as well as validation experiments with recombinant enzymes. In addition, we performed similar studies for caffeic and chlorogenic acids to compare the results. Docking experiments demonstrated that, from the tested compounds, only CA binds to both catalytic and secondary binding sites of YopH. Our experimental results showed that CA reduces activity of recombinant YopH phosphatase from Yersinia enterocolitica and human CD45 phosphatase.
2.Effect of Chicoric Acid on Mast Cell-Mediated Allergic Inflammation in Vitro and in Vivo.
Lee NY1,2, Chung KS1, Jin JS2, Bang KS, Eom YJ3, Hong CH3, Nugroho A4, Park HJ5, An HJ1. J Nat Prod. 2015 Dec 24;78(12):2956-62. doi: 10.1021/acs.jnatprod.5b00668. Epub 2015 Nov 23.
Chicoric acid (dicaffeoyl-tartaric acid), is a natural phenolic compound found in a number of plants, such as chicory (Cichorium intybus) and Echinacea (Echinacea purpurea), which possesses antioxidant, anti-inflammatory, antiviral, and analgesic activities. Although these biological effects of chicoric acid have been investigated, there are no reports of its antiallergic-related anti-inflammatory effects in human mast cells (HMC)-1 or anaphylactic activity in a mouse model. Therefore, we investigated the antiallergic-related anti-inflammatory effect of chicoric acid and its underlying mechanisms of action using phorbol-12-myristate 13-acetate plus calcium ionophore A23187 (PMACI)-stimulated HMC-1 cells. Chicoric acid decreased the mRNA expression of pro-inflammatory cytokines, such as tumor necrosis factor (TNF)-α, interleukin (IL)-6, and IL-1β. We studied the inhibitory effects of chicoric acid on the nuclear translocation of nuclear factor kappa B (NF-κB) and activation of caspase-1.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
