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chicoric acid
dicaffeoyl-D-tartaric acid

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Name:(2S,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
CAS Number: 70831-56-0Picture of molecule3D/inchi
FDA UNII: S4YY3V8YHD
Nikkaji Web:J503.502C
MDL:MFCD22683653
XlogP3-AA:2.00 (est)
Molecular Weight:474.37586000
Formula:C22 H18 O12
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
Soluble in:
 water, 25.62 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
L-Chicoric acid >98%
Odor: characteristic
Use: Cichoric acid, that can be isolated from the herbs of Echinacea purpurea, has been shown to inhibit hyaluronidase and HIV-1 integrase, and to possess phagoeytosis stimulatory activity in vitro and in vivo and antiviral acitivy. Chicoric acid may reduce a Anti-inflammatory
ExtraSynthese
For experimental / research use only.
Chicoric Acid (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Chicoric Acid
Sigma-Aldrich
For experimental / research use only.
(-)-Chicoric Acid
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for chicoric acid usage levels up to:
 not for fragrance use.
 
Recommendation for chicoric acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5470299
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Chemidplus:0052248483
 
References:
 (2S,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5470299
Pubchem (sid):135240645
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):C10437
HMDB (The Human Metabolome Database):HMDB02375
FooDB:FDB012145
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 chicory leaf
Search Trop Picture
 chicory plant
Search Trop Picture
 chicory shoot
Search Trop Picture
 endive
Search Trop Picture
 
Synonyms:
 butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (2S,3S)-
D-chicoric acid
dextro-chicoric acid
 dicaffeoyl-D-tartaric acid
(2S,3S)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}succinic acid
(2S,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
(1S,2S)-1,2-bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid
 

Articles:

PubMed:A Novel in Vitro Whole Plant System for Analysis of Polyphenolics and Their Antioxidant Potential in Cultivars of Ocimum basilicum.
PubMed:Phytochemical screening, anticancer and antioxidant activities of Origanum vulgare L. ssp. viride (Boiss.) Hayek, a plant of traditional usage.
PubMed:The effects of plant growth regulators and L-phenylalanine on phenolic compounds of sweet basil.
PubMed:Oral intake of chicoric acid reduces acute alcohol-induced hepatic steatosis in mice.
PubMed:Structural insight into exosite binding and discovery of novel exosite inhibitors of botulinum neurotoxin serotype A through in silico screening.
PubMed:Bioavailability of hydroxycinnamic acids from Crepidiastrum denticulatum using simulated digestion and Caco-2 intestinal cells.
PubMed:Echinacea purpurea (L.) Moench modulates human T-cell cytokine response.
PubMed:Hydroxycinnamic acids in Crepidiastrum denticulatum protect oxidative stress-induced retinal damage.
PubMed:[Simultaneous determination of five organic acids in Kudiezi injection by HPLC].
PubMed:Identification of chicoric acid as a hypoglycemic agent from Ocimum gratissimum leaf extract in a biomonitoring in vivo study.
PubMed:Induction of hepatocyte growth factor production in human dermal fibroblasts by caffeic acid derivatives.
PubMed:Chicoric acid is an antioxidant molecule that stimulates AMP kinase pathway in L6 myotubes and extends lifespan in Caenorhabditis elegans.
PubMed: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.
PubMed:Reversed-phase ultra-high-performance liquid chromatography coupled to electrospray ionization-quadrupole-time-of-flight mass spectrometry as a powerful tool for metabolic profiling of vegetables: Lactuca sativa as an example of its application.
PubMed:A liquid chromatography-tandem mass spectrometric method for the simultaneous quantitation of five components of Ixeris sonchifoliain (Bge.) Hance in rat plasma and its application to a pharmacokinetic study.
PubMed:Temporary reduction of radiation does not permanently reduce flavonoid glycosides and phenolic acids in red lettuce.
PubMed:[Induction of adventitious roots of Echinacea pallida and accumulation of caffeic acid derivatives].
PubMed:Amelioration by chicory seed extract of diabetes- and oleic acid-induced non-alcoholic fatty liver disease (NAFLD)/non-alcoholic steatohepatitis (NASH) via modulation of PPARα and SREBP-1.
PubMed:Isolation of phenolic compounds from iceberg lettuce and impact on enzymatic browning.
PubMed:Chicoric acid induces apoptosis in 3T3-L1 preadipocytes through ROS-mediated PI3K/Akt and MAPK signaling pathways.
PubMed:Application of an online post-column derivatization HPLC-DPPH assay to detect compounds responsible for antioxidant activity in Sonchus oleraceus L. leaf extracts.
PubMed:Chicoric acid: chemistry, distribution, and production.
PubMed:Seasonal variations in the concentrations of lipophilic compounds and phenolic acids in the roots of Echinacea purpurea and Echinacea pallida.
PubMed:Quantification of phenylpropanoids in commercial Echinacea products using TLC with video densitometry as detection technique and ANN for data modelling.
PubMed:Cytotoxic effects of Echinacea purpurea flower extracts and cichoric acid on human colon cancer cells through induction of apoptosis.
PubMed:Hydrolysis of chicoric and caftaric acids with esterases and Lactobacillus johnsonii in Vitro and in a gastrointestinal model.
PubMed:Molecular dynamics approach to probe the allosteric inhibition of PTP1B by chlorogenic and cichoric acid.
PubMed:Biomimetic formation of chicoric-acid-directed luminescent silver nanodendrites.
PubMed:Determination of major phenolic compounds in Echinacea spp. raw materials and finished products by high-performance liquid chromatography with ultraviolet detection: single-laboratory validation matrix extension.
PubMed:Computational fluid dynamics modeling of mass-transfer behavior in a bioreactor for hairy root culture. II. Analysis of ultrasound-intensified process.
PubMed:Chicoric acid regulates behavioral and biochemical alterations induced by chronic stress in experimental Swiss albino mice.
PubMed:Effect of high pressure pasteurization on bacterial load and bioactivity of Echinacea purpurea.
PubMed: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.
PubMed:Analysis of eleven phenolic compounds including novel p-coumaroyl derivatives in lettuce (Lactuca sativa L.) by ultra-high-performance liquid chromatography with photodiode array and mass spectrometry detection.
PubMed:Inhibition of stromelysin-1 by caffeic acid derivatives from a propolis sample from Algeria.
PubMed:Augmentation of immune response by chicoric acid through the modulation of CD28/CTLA-4 and Th1 pathway in chronically stressed mice.
PubMed:A cross-over inhibitor of the botulinum neurotoxin light chain B: a natural product implicating an exosite mechanism of action.
PubMed:Effect of the dietary polyphenolic fraction of chicory root, peel, seed and leaf extracts on caecal fermentation and blood parameters in rats fed diets containing prebiotic fructans.
PubMed:Taraxacum officinale Weber extracts inhibit LPS-induced oxidative stress and nitric oxide production via the NF-κB modulation in RAW 264.7 cells.
PubMed:Design, synthesis, and biological evaluation of novel hybrid dicaffeoyltartaric/diketo acid and tetrazole-substituted L-chicoric acid analogue inhibitors of human immunodeficiency virus type 1 integrase.
PubMed:Identification of a Natural Product Antagonist against the Botulinum Neurotoxin Light Chain Protease.
PubMed:Botulinum neurotoxin A protease: discovery of natural product exosite inhibitors.
PubMed:An allosteric mechanism for inhibiting HIV-1 integrase with a small molecule.
PubMed:Environmental stresses induce health-promoting phytochemicals in lettuce.
PubMed:A docking study of L-chicoric acid with HIV-1 integrase.
PubMed:Genomics and proteomics of immune modulatory effects of a butanol fraction of echinacea purpurea in human dendritic cells.
PubMed:Chicoric acid, a new compound able to enhance insulin release and glucose uptake.
PubMed:Echinacea alkylamides modulate induced immune responses in T-cells.
PubMed:Large-scale cultivation of adventitious roots of Echinacea purpurea in airlift bioreactors for the production of chichoric acid, chlorogenic acid and caftaric acid.
PubMed:Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors.
PubMed:Proliferative activity of Echinacea angustifolia root extracts on cancer cells: Interference with doxorubicin cytotoxicity.
PubMed:Ring substituent effects on biological activity of vinyl sulfones as inhibitors of HIV-1.
PubMed:Development and validation of a high-throughput based on liquid chromatography with ultraviolet absorption and mass spectrometry detection method for quantitation of cichoric acid in Echinacea purpurea aerial-based dietary supplements.
PubMed:Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves.
PubMed:Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase.
PubMed:Genetic diversity in seed populations of Echinacea purpurea controls the capacity for regeneration, route of morphogenesis and phytochemical composition.
PubMed:Preliminary mapping of a putative inhibitor-binding pocket for human immunodeficiency virus type 1 integrase inhibitors.
PubMed:Preparative separation of cichoric acid from Echinacea purpurea by pH-zone-refining counter-current chromatography.
PubMed:Synergistic antioxidative effects of alkamides, caffeic acid derivatives, and polysaccharide fractions from Echinacea purpurea on in vitro oxidation of human low-density lipoproteins.
PubMed:Human gene expression as a tool to determine horticultural maturity in a bioactive plant (Echinacea purpurea L. Moench).
PubMed:[Technology of extract improving the immune system].
PubMed:Evaluation of the phenolic content in the aerial parts of different varieties of Cichorium intybus L.
PubMed:Synthesis and biological evaluation of geminal disulfones as HIV-1 integrase inhibitors.
PubMed:Optimization of "Askoeziuofito" tablets.
PubMed:Cluster analysis and three-dimensional QSAR studies of HIV-1 integrase inhibitors.
PubMed:Characterization of phenolic acids and flavonoids in dandelion (Taraxacum officinale WEB. ex WIGG.) root and herb by high-performance liquid chromatography/electrospray ionization mass spectrometry.
PubMed:Effect of different washing procedures on phenolic metabolism of shredded, packaged iceberg lettuce during storage.
PubMed:Profile of resistance of human immunodeficiency virus to mannose-specific plant lectins.
PubMed: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.
PubMed:HIV-1 integrase inhibitors: a decade of research and two drugs in clinical trial.
PubMed:Human immunodeficiency virus type 1 (HIV-1) integrase: resistance to diketo acid integrase inhibitors impairs HIV-1 replication and integration and confers cross-resistance to L-chicoric acid.
PubMed:Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors.
PubMed:HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products.
PubMed:Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors.
PubMed:[Vasorelaxant activity of caffeic acid derivatives from Cichorium intybus and Equisetum arvense].
PubMed:Structure-activity relationships of HIV-1 integrase inhibitors--enzyme-ligand interactions.
PubMed:[Determination of cichoric acid in Echinacea purpuea].
PubMed:Human immunodeficiency virus type-1 integrase containing a glycine to serine mutation at position 140 is attenuated for catalysis and resistant to integrase inhibitors.
PubMed:Effect of drying temperature on alkylamide and cichoric acid concentrations of Echinacea purpurea.
PubMed:Antiviral activity of characterized extracts from echinacea spp. (Heliantheae: Asteraceae) against herpes simplex virus (HSV-I).
PubMed:In search of authentic inhibitors of HIV-1 integration.
PubMed:Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations.
PubMed:Simultaneous analysis of alkamides and caffeic acid derivatives for the identification of Echinacea purpurea, Echinacea angustifolia, Echinacea pallida and Parthenium integrifolium roots.
PubMed:New developments in anti-HIV chemotherapy.
PubMed:Stabilization of caffeic acid derivatives in Echinacea purpurea L. glycerin extract.
PubMed:Phytochemical variation in echinacea from roots and flowerheads of wild and cultivated populations.
PubMed:Effect of temperature on stability of marker constituents in Echinacea purpurea root formulations.
PubMed:New developments in anti-HIV chemotherapy.
PubMed:Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors.
PubMed:Natural selection results in conservation of HIV-1 integrase activity despite sequence variability.
PubMed:Drug watch.
PubMed:[Chicoric and chlorogenic acids in various plants growing in Georgia].
PubMed:Echinacea standardization: analytical methods for phenolic compounds and typical levels in medicinal species.
PubMed:Predicting quantitative phytochemical markers in single Echinacea plants or clones from their DNA fingerprints.
PubMed:Enzymatic degradation of cichoric acid in Echinacea purpurea preparations.
PubMed:Active site binding modes of HIV-1 integrase inhibitors.
PubMed:Retention of caffeic acid derivatives in dried Echinacea purpurea.
PubMed:Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides.
PubMed:Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters.
PubMed:Current lead natural products for the chemotherapy of human immunodeficiency virus (HIV) infection.
PubMed:Novel compounds in preclinical/early clinical development for the treatment of HIV infections.
PubMed:Combinations of reverse transcriptase, protease, and integrase inhibitors can be synergistic in vitro against drug-sensitive and RT inhibitor-resistant molecular clones of HIV-1.
PubMed:Chicoric acid analogues as HIV-1 integrase inhibitors.
PubMed:Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.
PubMed:[The anti-HIV action of chicoric acid].
PubMed:L-chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of Zidovudine plus a protease inhibitor (AG1350).
PubMed:Green coffee beans may yield new class of anti-HIV-1 agents.
PubMed:Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase.
PubMed:Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.
PubMed:Potent inhibitors of human immunodeficiency virus type 1 integrase: identification of a novel four-point pharmacophore and tetracyclines as novel inhibitors.
PubMed:Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.
PubMed:Flavonoids, cinnamic acids and coumarins from the different tissues and medicinal preparations of Taraxacum officinale.
PubMed:Echinacoside and caffeoyl conjugates protect collagen from free radical-induced degradation: a potential use of Echinacea extracts in the prevention of skin photodamage.
PubMed:Direct characterization of caffeoyl esters with antihyaluronidase activity in crude extracts from Echinacea angustifolia roots by fast atom bombardment tandem mass spectrometry.
 
Notes:
Isol. from chicory (Cichorium intybus) and Cichorium endivia (endive)
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